# Supporting Info (ESI) - part 1 data_global _publ_contact_author_name 'Gale, Philip' _publ_contact_author_email philip.gale@soton.ac.uk _publ_section_title ; Towards Predictable Transmembrane Transport: QSAR Analysis of Anion Binding and Anion Transport Properties of Thioureas ; loop_ _publ_author_name 'Nathalie Busschaert' 'Samuel J. Bradberry' 'Marco Wenzel' 'Cally J. E. Haynes' 'Jennifer R. Hiscock' 'Isabelle L. Kirby' 'Louise Karagiannidis' 'Stephen J. Morre' 'Neil J. Wells' 'Julie Herniman' 'G. John Langley' 'Peter N. Horton' 'Mark E. Light' 'Igor Marques' 'Paulo J. Costa' 'Vítor Félix' 'Jeremy G. Frey' 'Philip A. Gale' data_p-Br _chemical_compound_source 'Nathalie Busschaert' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H19 Br N2 S' _chemical_formula_sum 'C13 H19 Br N2 S' _chemical_formula_weight 315.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.3563(8) _cell_length_b 7.8428(3) _cell_length_c 21.0265(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.599(7) _cell_angle_gamma 90.00 _cell_volume 2837.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 20191 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 3.026 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.5067 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Left)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26506 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6491 _reflns_number_gt 4955 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0253P)^2^+0.3437P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6491 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.44792(16) 0.7550(3) 0.47632(11) 0.0335(6) Uani 1 1 d . . . H1A H -0.5019 0.7879 0.4620 0.050 Uiso 1 1 calc R . . H1B H -0.4249 0.8349 0.5093 0.050 Uiso 1 1 calc R . . H1C H -0.4467 0.6395 0.4942 0.050 Uiso 1 1 calc R . . C2 C -0.40162(13) 0.7591(3) 0.41939(10) 0.0225(5) Uani 1 1 d . . . H2A H -0.4255 0.6790 0.3861 0.027 Uiso 1 1 calc R . . H2B H -0.4046 0.8751 0.4006 0.027 Uiso 1 1 calc R . . C3 C -0.31692(13) 0.7113(3) 0.43798(10) 0.0181(5) Uani 1 1 d . . . H3A H -0.3144 0.5944 0.4559 0.022 Uiso 1 1 calc R . . H3B H -0.2938 0.7894 0.4723 0.022 Uiso 1 1 calc R . . C4 C -0.26785(13) 0.7181(3) 0.38281(10) 0.0169(5) Uani 1 1 d . . . H4A H -0.2927 0.6471 0.3469 0.020 Uiso 1 1 calc R . . H4B H -0.2660 0.8370 0.3673 0.020 Uiso 1 1 calc R . . C5 C -0.18576(13) 0.6552(3) 0.40296(9) 0.0154(5) Uani 1 1 d . . . H5A H -0.1878 0.5343 0.4162 0.019 Uiso 1 1 calc R . . H5B H -0.1624 0.7215 0.4407 0.019 Uiso 1 1 calc R . . C6 C -0.13370(13) 0.6699(3) 0.35048(9) 0.0169(5) Uani 1 1 d . . . H6A H -0.1589 0.6137 0.3110 0.020 Uiso 1 1 calc R . . H6B H -0.1258 0.7916 0.3406 0.020 Uiso 1 1 calc R . . C7 C 0.00668(13) 0.6130(3) 0.34602(9) 0.0143(5) Uani 1 1 d . . . C8 C 0.14757(13) 0.5365(3) 0.36480(9) 0.0153(5) Uani 1 1 d . . . C9 C 0.20539(13) 0.5823(3) 0.41382(10) 0.0184(5) Uani 1 1 d . . . H9 H 0.1915 0.6168 0.4541 0.022 Uiso 1 1 calc R . . C10 C 0.28308(14) 0.5786(3) 0.40495(11) 0.0222(5) Uani 1 1 d . . . H10 H 0.3225 0.6097 0.4387 0.027 Uiso 1 1 calc R . . C11 C 0.30214(13) 0.5285(3) 0.34554(11) 0.0199(5) Uani 1 1 d . . . C12 C 0.24482(14) 0.4803(3) 0.29639(10) 0.0191(5) Uani 1 1 d . . . H12 H 0.2587 0.4460 0.2561 0.023 Uiso 1 1 calc R . . C13 C 0.16760(14) 0.4823(3) 0.30601(9) 0.0167(5) Uani 1 1 d . . . H13 H 0.1284 0.4469 0.2728 0.020 Uiso 1 1 calc R . . C14 C 0.54360(15) 0.5091(3) 0.21589(11) 0.0307(6) Uani 1 1 d . . . H14A H 0.4880 0.5175 0.2001 0.046 Uiso 1 1 calc R . . H14B H 0.5581 0.5997 0.2473 0.046 Uiso 1 1 calc R . . H14C H 0.5546 0.3978 0.2363 0.046 Uiso 1 1 calc R . . C15 C 0.59068(13) 0.5284(3) 0.15974(10) 0.0217(5) Uani 1 1 d . . . H15A H 0.5751 0.4377 0.1279 0.026 Uiso 1 1 calc R . . H15B H 0.5781 0.6397 0.1386 0.026 Uiso 1 1 calc R . . C16 C 0.67829(14) 0.5179(3) 0.18019(10) 0.0194(5) Uani 1 1 d . . . H16A H 0.6911 0.4027 0.1977 0.023 Uiso 1 1 calc R . . H16B H 0.6928 0.6011 0.2151 0.023 Uiso 1 1 calc R . . C17 C 0.72726(14) 0.5528(3) 0.12627(9) 0.0174(5) Uani 1 1 d . . . H17A H 0.7128 0.4707 0.0910 0.021 Uiso 1 1 calc R . . H17B H 0.7158 0.6690 0.1092 0.021 Uiso 1 1 calc R . . C18 C 0.81345(13) 0.5380(3) 0.14891(9) 0.0167(5) Uani 1 1 d . . . H18A H 0.8249 0.4207 0.1649 0.020 Uiso 1 1 calc R . . H18B H 0.8273 0.6173 0.1853 0.020 Uiso 1 1 calc R . . C19 C 0.86373(13) 0.5774(3) 0.09686(9) 0.0189(5) Uani 1 1 d . . . H19A H 0.8541 0.4919 0.0621 0.023 Uiso 1 1 calc R . . H19B H 0.8501 0.6912 0.0783 0.023 Uiso 1 1 calc R . . C20 C 1.00439(13) 0.6471(3) 0.09938(9) 0.0140(5) Uani 1 1 d . . . C21 C 1.14848(13) 0.6731(3) 0.12631(9) 0.0132(4) Uani 1 1 d . . . C22 C 1.20228(14) 0.7470(3) 0.17278(9) 0.0165(5) Uani 1 1 d . . . H22 H 1.1868 0.7807 0.2126 0.020 Uiso 1 1 calc R . . C23 C 1.27859(14) 0.7724(3) 0.16176(10) 0.0187(5) Uani 1 1 d . . . H23 H 1.3154 0.8214 0.1941 0.022 Uiso 1 1 calc R . . C24 C 1.30065(13) 0.7257(3) 0.10301(10) 0.0181(5) Uani 1 1 d . . . C25 C 1.24765(14) 0.6508(3) 0.05657(9) 0.0179(5) Uani 1 1 d . . . H25 H 1.2632 0.6188 0.0166 0.021 Uiso 1 1 calc R . . C26 C 1.17213(13) 0.6222(3) 0.06804(9) 0.0164(5) Uani 1 1 d . . . H26 H 1.1362 0.5679 0.0364 0.020 Uiso 1 1 calc R . . N1 N -0.05894(11) 0.5897(2) 0.37123(8) 0.0165(4) Uani 1 1 d . . . H1 H -0.0569 0.5185 0.4038 0.020 Uiso 1 1 calc R . . N2 N 0.06957(11) 0.5341(2) 0.37826(8) 0.0172(4) Uani 1 1 d . . . H2 H 0.0609 0.4736 0.4118 0.021 Uiso 1 1 calc R . . N3 N 0.94540(11) 0.5746(2) 0.12361(8) 0.0169(4) Uani 1 1 d . . . H3 H 0.9571 0.5186 0.1599 0.020 Uiso 1 1 calc R . . N4 N 1.07260(11) 0.6428(2) 0.14013(7) 0.0143(4) Uani 1 1 d . . . H4 H 1.0685 0.6176 0.1803 0.017 Uiso 1 1 calc R . . S1 S 0.01011(3) 0.73606(7) 0.27974(2) 0.01545(12) Uani 1 1 d . . . S2 S 0.99385(3) 0.74430(7) 0.02648(2) 0.01585(12) Uani 1 1 d . . . Br1 Br 0.407632(15) 0.52571(3) 0.331258(13) 0.03549(8) Uani 1 1 d . . . Br2 Br 1.404166(14) 0.76440(3) 0.086548(11) 0.02553(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0206(15) 0.0507(17) 0.0311(13) 0.0044(12) 0.0102(11) 0.0104(13) C2 0.0164(13) 0.0287(13) 0.0229(11) 0.0025(10) 0.0049(10) 0.0012(11) C3 0.0144(12) 0.0210(11) 0.0196(10) 0.0012(9) 0.0046(9) -0.0029(10) C4 0.0144(12) 0.0191(11) 0.0173(10) -0.0009(9) 0.0018(9) -0.0004(10) C5 0.0131(12) 0.0190(11) 0.0143(10) -0.0023(9) 0.0021(8) -0.0004(10) C6 0.0116(12) 0.0203(11) 0.0188(10) 0.0023(9) 0.0017(9) -0.0005(10) C7 0.0181(13) 0.0125(10) 0.0120(10) -0.0046(8) 0.0011(8) -0.0028(10) C8 0.0132(12) 0.0136(10) 0.0195(11) 0.0055(9) 0.0038(9) 0.0005(9) C9 0.0182(13) 0.0183(11) 0.0182(11) -0.0017(9) 0.0007(9) 0.0003(10) C10 0.0176(13) 0.0208(12) 0.0266(12) -0.0015(10) -0.0029(10) -0.0023(11) C11 0.0126(13) 0.0149(11) 0.0339(13) 0.0079(10) 0.0088(10) 0.0006(10) C12 0.0220(14) 0.0176(11) 0.0190(11) 0.0046(9) 0.0070(9) 0.0026(11) C13 0.0181(13) 0.0155(11) 0.0159(10) 0.0021(9) -0.0001(9) -0.0002(10) C14 0.0194(14) 0.0442(16) 0.0300(13) 0.0032(12) 0.0090(10) 0.0028(13) C15 0.0157(13) 0.0289(13) 0.0205(11) 0.0008(10) 0.0031(10) -0.0010(11) C16 0.0184(13) 0.0235(12) 0.0162(10) 0.0014(9) 0.0024(9) 0.0009(11) C17 0.0201(13) 0.0183(11) 0.0140(10) -0.0010(9) 0.0028(9) 0.0008(10) C18 0.0170(13) 0.0181(11) 0.0151(10) -0.0006(9) 0.0030(9) -0.0005(10) C19 0.0144(12) 0.0272(12) 0.0151(10) -0.0003(9) 0.0014(9) -0.0033(10) C20 0.0168(12) 0.0132(10) 0.0123(10) -0.0034(8) 0.0034(8) 0.0025(9) C21 0.0119(12) 0.0137(10) 0.0146(10) 0.0040(8) 0.0037(8) 0.0032(9) C22 0.0199(13) 0.0187(11) 0.0107(9) 0.0011(9) 0.0020(8) 0.0013(10) C23 0.0199(13) 0.0166(11) 0.0185(10) -0.0008(9) -0.0019(9) -0.0017(10) C24 0.0131(12) 0.0180(11) 0.0239(11) 0.0054(9) 0.0049(9) 0.0044(10) C25 0.0196(13) 0.0206(11) 0.0138(10) 0.0006(9) 0.0033(9) 0.0045(10) C26 0.0167(13) 0.0180(11) 0.0143(10) -0.0012(9) 0.0012(9) 0.0021(10) N1 0.0161(11) 0.0177(9) 0.0164(9) 0.0052(7) 0.0041(7) 0.0015(8) N2 0.0141(10) 0.0228(10) 0.0158(8) 0.0084(8) 0.0055(7) 0.0004(9) N3 0.0163(11) 0.0235(10) 0.0105(8) 0.0038(7) 0.0005(7) -0.0012(9) N4 0.0140(10) 0.0216(10) 0.0079(8) 0.0020(7) 0.0034(7) -0.0002(8) S1 0.0177(3) 0.0173(3) 0.0117(2) 0.0014(2) 0.0034(2) 0.0015(2) S2 0.0180(3) 0.0188(3) 0.0108(2) 0.0018(2) 0.0019(2) 0.0021(2) Br1 0.01498(14) 0.03531(15) 0.05844(18) 0.00535(13) 0.01328(12) 0.00076(12) Br2 0.01454(13) 0.02815(14) 0.03506(14) 0.00689(11) 0.00759(10) 0.00214(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.528(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.517(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.514(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.520(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.456(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N1 1.331(3) . ? C7 N2 1.356(3) . ? C7 S1 1.703(2) . ? C8 C9 1.387(3) . ? C8 C13 1.394(3) . ? C8 N2 1.419(3) . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.391(3) . ? C10 H10 0.9500 . ? C11 C12 1.389(3) . ? C11 Br1 1.894(2) . ? C12 C13 1.382(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.529(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.527(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.529(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.513(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.519(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N3 1.454(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N3 1.330(3) . ? C20 N4 1.367(3) . ? C20 S2 1.700(2) . ? C21 C22 1.386(3) . ? C21 C26 1.401(3) . ? C21 N4 1.406(3) . ? C22 C23 1.389(3) . ? C22 H22 0.9500 . ? C23 C24 1.390(3) . ? C23 H23 0.9500 . ? C24 C25 1.381(3) . ? C24 Br2 1.899(2) . ? C25 C26 1.382(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? N3 H3 0.8800 . ? N4 H4 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 112.65(19) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 114.47(18) . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C5 C4 C3 112.00(17) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 113.57(17) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N1 C6 C5 109.96(16) . . ? N1 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? N1 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? N1 C7 N2 114.38(17) . . ? N1 C7 S1 121.90(17) . . ? N2 C7 S1 123.71(17) . . ? C9 C8 C13 119.8(2) . . ? C9 C8 N2 118.07(18) . . ? C13 C8 N2 121.9(2) . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 118.6(2) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C12 C11 C10 120.9(2) . . ? C12 C11 Br1 119.42(16) . . ? C10 C11 Br1 119.70(18) . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 119.6(2) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C14 113.03(18) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 114.35(18) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C16 112.11(17) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C19 113.33(17) . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? N3 C19 C18 109.98(17) . . ? N3 C19 H19A 109.7 . . ? C18 C19 H19A 109.7 . . ? N3 C19 H19B 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? N3 C20 N4 113.32(17) . . ? N3 C20 S2 122.73(17) . . ? N4 C20 S2 123.88(16) . . ? C22 C21 C26 119.2(2) . . ? C22 C21 N4 119.16(18) . . ? C26 C21 N4 121.55(19) . . ? C21 C22 C23 120.72(19) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C24 119.4(2) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 120.3(2) . . ? C25 C24 Br2 119.81(16) . . ? C23 C24 Br2 119.89(17) . . ? C24 C25 C26 120.27(19) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 120.0(2) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C7 N1 C6 126.64(17) . . ? C7 N1 H1 116.7 . . ? C6 N1 H1 116.7 . . ? C7 N2 C8 128.34(17) . . ? C7 N2 H2 115.8 . . ? C8 N2 H2 115.8 . . ? C20 N3 C19 127.26(18) . . ? C20 N3 H3 116.4 . . ? C19 N3 H3 116.4 . . ? C20 N4 C21 128.57(17) . . ? C20 N4 H4 115.7 . . ? C21 N4 H4 115.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 S2 0.88 2.48 3.3124(17) 158.3 2_645 N3 H3 S1 0.88 2.58 3.3703(18) 150.0 2_645 N4 H4 S1 0.88 2.61 3.3423(16) 141.1 1_655 N1 H1 S2 0.88 2.75 3.5491(18) 152.0 2_645 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.397 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.091 #===END data_p-CF3 _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Stephen Moore ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H19 F3 N2 S' _chemical_formula_sum 'C14 H19 F3 N2 S' _chemical_formula_weight 304.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.298(8) _cell_length_b 13.278(6) _cell_length_c 8.673(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.912(18) _cell_angle_gamma 90.00 _cell_volume 1530.5(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1707 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9140 _exptl_absorpt_correction_T_max 0.9930 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8095 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.1028 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3436 _reflns_number_gt 2288 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3436 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2932(2) 0.0921(2) -0.8674(3) 0.0388(8) Uani 1 1 d . . . H1A H -0.3036 0.1165 -0.9733 0.058 Uiso 1 1 calc R . . H1B H -0.3514 0.1101 -0.8067 0.058 Uiso 1 1 calc R . . H1C H -0.2855 0.0187 -0.8683 0.058 Uiso 1 1 calc R . . C2 C -0.1983(2) 0.1402(2) -0.7953(3) 0.0284(6) Uani 1 1 d . . . H2A H -0.1399 0.1228 -0.8581 0.034 Uiso 1 1 calc R . . H2B H -0.2059 0.2144 -0.7964 0.034 Uiso 1 1 calc R . . C3 C -0.17815(18) 0.10495(19) -0.6301(3) 0.0220(6) Uani 1 1 d . . . H3A H -0.1716 0.0307 -0.6296 0.026 Uiso 1 1 calc R . . H3B H -0.2367 0.1226 -0.5679 0.026 Uiso 1 1 calc R . . C4 C -0.08349(18) 0.15063(19) -0.5540(3) 0.0202(6) Uani 1 1 d . . . H4A H -0.0913 0.2246 -0.5477 0.024 Uiso 1 1 calc R . . H4B H -0.0251 0.1363 -0.6183 0.024 Uiso 1 1 calc R . . C5 C -0.06354(18) 0.10799(19) -0.3916(3) 0.0194(5) Uani 1 1 d . . . H5A H -0.1222 0.1218 -0.3275 0.023 Uiso 1 1 calc R . . H5B H -0.0549 0.0341 -0.3979 0.023 Uiso 1 1 calc R . . C6 C 0.03044(18) 0.15466(19) -0.3157(3) 0.0196(6) Uani 1 1 d . . . H6A H 0.0897 0.1397 -0.3780 0.024 Uiso 1 1 calc R . . H6B H 0.0226 0.2287 -0.3101 0.024 Uiso 1 1 calc R . . C7 C 0.11906(17) 0.13852(17) -0.0583(3) 0.0178(5) Uani 1 1 d . . . C8 C 0.27215(17) 0.24700(19) -0.0192(3) 0.0184(5) Uani 1 1 d . . . C9 C 0.33771(17) 0.1802(2) 0.0581(3) 0.0218(6) Uani 1 1 d . . . H9 H 0.3249 0.1099 0.0563 0.026 Uiso 1 1 calc R . . C10 C 0.42191(17) 0.21824(19) 0.1376(3) 0.0234(6) Uani 1 1 d . . . H10 H 0.4665 0.1736 0.1914 0.028 Uiso 1 1 calc R . . C11 C 0.44152(18) 0.3215(2) 0.1390(3) 0.0226(6) Uani 1 1 d . . . C12 C 0.37770(19) 0.3882(2) 0.0584(3) 0.0243(6) Uani 1 1 d . . . H12 H 0.3922 0.4583 0.0571 0.029 Uiso 1 1 calc R . . C13 C 0.29251(18) 0.35080(19) -0.0199(3) 0.0216(6) Uani 1 1 d . . . H13 H 0.2481 0.3955 -0.0739 0.026 Uiso 1 1 calc R . . C14 C 0.53431(19) 0.3618(2) 0.2208(3) 0.0294(7) Uani 1 1 d . . . N1 N 0.04591(14) 0.11325(15) -0.1595(2) 0.0188(5) Uani 1 1 d . . . H1 H 0.0027 0.0674 -0.1301 0.023 Uiso 1 1 calc R . . N2 N 0.18481(14) 0.21176(15) -0.1031(2) 0.0199(5) Uani 1 1 d . . . H2 H 0.1717 0.2401 -0.1933 0.024 Uiso 1 1 calc R . . F1 F 0.57094(12) 0.29787(13) 0.3287(2) 0.0446(5) Uani 1 1 d . . . F2 F 0.61049(12) 0.37713(15) 0.1242(2) 0.0529(6) Uani 1 1 d . . . F3 F 0.51906(13) 0.45066(14) 0.2909(3) 0.0634(7) Uani 1 1 d . . . S1 S 0.12384(5) 0.08229(5) 0.11945(7) 0.01920(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0317(16) 0.0474(19) 0.0362(17) -0.0035(15) -0.0158(13) 0.0008(13) C2 0.0267(14) 0.0342(16) 0.0236(14) 0.0014(12) -0.0083(11) 0.0002(12) C3 0.0197(13) 0.0257(14) 0.0204(12) 0.0010(11) -0.0023(10) -0.0017(10) C4 0.0201(13) 0.0245(14) 0.0159(12) 0.0007(10) -0.0009(10) -0.0018(10) C5 0.0181(12) 0.0237(14) 0.0162(11) 0.0013(10) -0.0006(10) -0.0031(10) C6 0.0205(13) 0.0228(14) 0.0155(12) 0.0035(11) -0.0016(10) -0.0024(10) C7 0.0159(12) 0.0195(13) 0.0181(12) -0.0041(10) 0.0007(10) 0.0021(10) C8 0.0146(12) 0.0273(14) 0.0135(11) -0.0010(11) 0.0022(9) -0.0029(10) C9 0.0191(13) 0.0210(14) 0.0253(13) -0.0019(11) 0.0011(11) -0.0008(10) C10 0.0158(13) 0.0279(15) 0.0262(14) 0.0021(11) -0.0017(11) 0.0018(10) C11 0.0173(12) 0.0293(15) 0.0213(13) -0.0055(11) 0.0006(10) -0.0024(11) C12 0.0245(13) 0.0264(14) 0.0222(13) -0.0015(11) 0.0022(11) -0.0057(11) C13 0.0215(13) 0.0267(15) 0.0167(12) 0.0024(11) 0.0002(10) -0.0011(11) C14 0.0210(14) 0.0356(17) 0.0316(15) -0.0048(13) -0.0005(12) -0.0056(12) N1 0.0184(11) 0.0244(11) 0.0133(10) 0.0015(8) -0.0020(8) -0.0059(9) N2 0.0181(10) 0.0260(12) 0.0154(10) 0.0022(9) -0.0034(9) -0.0034(9) F1 0.0370(10) 0.0541(11) 0.0413(10) 0.0075(8) -0.0209(8) -0.0129(8) F2 0.0217(9) 0.0862(15) 0.0505(12) 0.0091(10) -0.0018(8) -0.0198(9) F3 0.0360(11) 0.0490(12) 0.1031(18) -0.0401(12) -0.0302(11) 0.0028(8) S1 0.0196(3) 0.0240(4) 0.0138(3) 0.0024(3) -0.0024(2) -0.0026(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.530(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.522(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.527(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.533(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.525(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.470(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N1 1.331(3) . ? C7 N2 1.373(3) . ? C7 S1 1.712(3) . ? C8 C9 1.399(3) . ? C8 C13 1.405(3) . ? C8 N2 1.429(3) . ? C9 C10 1.390(3) . ? C9 H9 0.9500 . ? C10 C11 1.396(4) . ? C10 H10 0.9500 . ? C11 C12 1.398(3) . ? C11 C14 1.501(3) . ? C12 C13 1.393(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 F1 1.343(3) . ? C14 F3 1.346(3) . ? C14 F2 1.351(3) . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 111.9(2) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 113.6(2) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 111.4(2) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 111.2(2) . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N1 C6 C5 109.5(2) . . ? N1 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N1 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? N1 C7 N2 116.8(2) . . ? N1 C7 S1 119.21(19) . . ? N2 C7 S1 123.99(16) . . ? C9 C8 C13 120.5(2) . . ? C9 C8 N2 121.3(2) . . ? C13 C8 N2 118.2(2) . . ? C10 C9 C8 119.1(2) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 120.5(2) . . ? C10 C11 C14 120.3(2) . . ? C12 C11 C14 119.1(2) . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C8 120.1(2) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? F1 C14 F3 107.2(2) . . ? F1 C14 F2 105.4(2) . . ? F3 C14 F2 106.0(2) . . ? F1 C14 C11 112.2(2) . . ? F3 C14 C11 113.1(2) . . ? F2 C14 C11 112.5(2) . . ? C7 N1 C6 126.2(2) . . ? C7 N1 H1 116.9 . . ? C6 N1 H1 116.9 . . ? C7 N2 C8 127.1(2) . . ? C7 N2 H2 116.5 . . ? C8 N2 H2 116.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.61 3.465(2) 164.8 3 N2 H2 S1 0.88 2.92 3.714(2) 150.7 4_565 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.590 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.079 #===END data_p-Cl _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H19 Cl N2 S' _chemical_formula_sum 'C13 H19 Cl N2 S' _chemical_formula_weight 270.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.987(7) _cell_length_b 8.170(4) _cell_length_c 24.959(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2852(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7860 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 33.9 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7692 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13636 _diffrn_reflns_av_R_equivalents 0.0758 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2526 _reflns_number_gt 2278 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+5.3737P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2526 _refine_ls_number_parameters 176 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1033 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.1342 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.324 _refine_ls_restrained_S_all 1.323 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.10725(9) 0.19900(13) 0.00544(4) 0.0326(3) Uani 1 1 d . . . C1 C 0.2158(3) 0.1836(5) 0.12300(16) 0.0318(11) Uani 1 1 d . . . H1A H 0.1501 0.2048 0.1162 0.038 Uiso 1 1 calc R . . C2 C 0.2426(3) 0.0887(5) 0.16674(16) 0.0312(10) Uani 1 1 d . . . H2A H 0.1951 0.0426 0.1894 0.037 Uiso 1 1 calc R . . C3 C 0.3384(3) 0.0617(5) 0.17719(16) 0.0298(10) Uani 1 1 d . . . C4 C 0.4085(3) 0.1268(5) 0.14449(17) 0.0356(11) Uani 1 1 d . . . H4 H 0.4741 0.1085 0.1522 0.043 Uiso 1 1 calc R . . C5 C 0.3817(3) 0.2194(5) 0.10030(17) 0.0346(11) Uani 1 1 d . . . H5 H 0.4294 0.2639 0.0774 0.042 Uiso 1 1 calc R . . C6 C 0.2855(3) 0.2473(5) 0.08930(16) 0.0266(10) Uani 1 1 d . . . C7 C 0.1882(3) 0.3529(5) 0.01158(16) 0.0303(10) Uani 1 1 d . A . C8A C 0.1161(3) 0.5201(5) -0.06190(17) 0.0341(11) Uani 0.607(6) 1 d PD A 1 H8A1 H 0.0504 0.5028 -0.0484 0.041 Uiso 0.607(6) 1 calc PR A 1 H8A2 H 0.1273 0.4412 -0.0914 0.041 Uiso 0.607(6) 1 calc PR A 1 C9A C 0.125(2) 0.695(2) -0.0838(11) 0.035(3) Uani 0.607(6) 1 d PD A 1 H9A1 H 0.1092 0.7736 -0.0550 0.042 Uiso 0.607(6) 1 calc PR A 1 H9A2 H 0.1917 0.7147 -0.0951 0.042 Uiso 0.607(6) 1 calc PR A 1 C10A C 0.0590(9) 0.7236(16) -0.1309(7) 0.037(3) Uani 0.607(6) 1 d PD A 1 H10A H -0.0065 0.6889 -0.1211 0.045 Uiso 0.607(6) 1 calc PR A 1 H10B H 0.0803 0.6552 -0.1614 0.045 Uiso 0.607(6) 1 calc PR A 1 C11A C 0.0568(6) 0.9038(9) -0.1486(3) 0.0379(18) Uani 0.607(6) 1 d PD A 1 H11A H 0.0062 0.9173 -0.1760 0.045 Uiso 0.607(6) 1 calc PR A 1 H11B H 0.0391 0.9721 -0.1174 0.045 Uiso 0.607(6) 1 calc PR A 1 C12A C 0.1495(6) 0.9664(10) -0.1713(4) 0.0437(19) Uani 0.607(6) 1 d PD A 1 H12A H 0.1688 0.8967 -0.2018 0.052 Uiso 0.607(6) 1 calc PR A 1 H12B H 0.1999 0.9586 -0.1435 0.052 Uiso 0.607(6) 1 calc PR A 1 C13A C 0.1411(8) 1.1447(11) -0.1902(4) 0.050(3) Uani 0.607(6) 1 d PD A 1 H13A H 0.2027 1.1811 -0.2046 0.075 Uiso 0.607(6) 1 calc PR A 1 H13B H 0.1231 1.2144 -0.1598 0.075 Uiso 0.607(6) 1 calc PR A 1 H13C H 0.0922 1.1525 -0.2181 0.075 Uiso 0.607(6) 1 calc PR A 1 C8B C 0.1161(3) 0.5201(5) -0.06190(17) 0.0341(11) Uani 0.393(6) 1 d PD A 2 H8B1 H 0.0496 0.5189 -0.0484 0.041 Uiso 0.393(6) 1 calc PR A 2 H8B2 H 0.1225 0.4383 -0.0909 0.041 Uiso 0.393(6) 1 calc PR A 2 C9B C 0.145(3) 0.692(3) -0.0815(17) 0.035(3) Uani 0.393(6) 1 d PD A 2 H9B1 H 0.1348 0.7700 -0.0517 0.042 Uiso 0.393(6) 1 calc PR A 2 H9B2 H 0.2136 0.6909 -0.0901 0.042 Uiso 0.393(6) 1 calc PR A 2 C10B C 0.0906(16) 0.753(3) -0.1298(12) 0.037(3) Uani 0.393(6) 1 d PD A 2 H10C H 0.0216 0.7567 -0.1210 0.045 Uiso 0.393(6) 1 calc PR A 2 H10D H 0.0989 0.6731 -0.1594 0.045 Uiso 0.393(6) 1 calc PR A 2 C11B C 0.1226(11) 0.9235(16) -0.1494(5) 0.0379(18) Uani 0.393(6) 1 d PD A 2 H11C H 0.1167 1.0016 -0.1192 0.045 Uiso 0.393(6) 1 calc PR A 2 H11D H 0.1911 0.9179 -0.1593 0.045 Uiso 0.393(6) 1 calc PR A 2 C12B C 0.0672(9) 0.9898(14) -0.1965(4) 0.0437(19) Uani 0.393(6) 1 d PD A 2 H12C H -0.0010 1.0004 -0.1863 0.052 Uiso 0.393(6) 1 calc PR A 2 H12D H 0.0713 0.9110 -0.2265 0.052 Uiso 0.393(6) 1 calc PR A 2 C13B C 0.1042(12) 1.1556(16) -0.2151(6) 0.044(4) Uani 0.393(6) 1 d PD A 2 H13D H 0.0652 1.1944 -0.2452 0.066 Uiso 0.393(6) 1 calc PR A 2 H13E H 0.1709 1.1448 -0.2266 0.066 Uiso 0.393(6) 1 calc PR A 2 H13F H 0.1002 1.2341 -0.1855 0.066 Uiso 0.393(6) 1 calc PR A 2 N1 N 0.2643(3) 0.3526(4) 0.04569(13) 0.0303(9) Uani 1 1 d . . . H1 H 0.3069 0.4297 0.0397 0.036 Uiso 1 1 calc R . . N2 N 0.1841(3) 0.4880(4) -0.01877(13) 0.0330(9) Uani 1 1 d . . . H2 H 0.2266 0.5649 -0.0121 0.040 Uiso 1 1 calc R A 1 Cl2 Cl 0.37183(9) -0.05714(15) 0.23245(5) 0.0435(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0292(6) 0.0313(6) 0.0374(6) 0.0002(5) -0.0052(5) -0.0006(5) C1 0.026(3) 0.037(3) 0.033(2) -0.004(2) 0.001(2) 0.006(2) C2 0.030(3) 0.035(3) 0.028(2) -0.0061(19) 0.001(2) -0.001(2) C3 0.035(3) 0.028(2) 0.026(2) -0.0006(19) -0.004(2) 0.000(2) C4 0.018(2) 0.046(3) 0.043(3) 0.001(2) -0.006(2) -0.001(2) C5 0.026(3) 0.039(3) 0.040(3) 0.001(2) 0.001(2) -0.007(2) C6 0.028(3) 0.020(2) 0.031(2) -0.0046(18) -0.005(2) 0.0020(19) C7 0.037(3) 0.025(2) 0.028(2) -0.0013(18) 0.003(2) 0.004(2) C8A 0.031(3) 0.036(3) 0.035(2) 0.002(2) -0.004(2) 0.003(2) C9A 0.039(11) 0.032(3) 0.035(3) 0.002(2) -0.001(5) 0.011(4) C10A 0.030(9) 0.047(6) 0.035(3) -0.001(4) -0.001(6) 0.007(5) C11A 0.035(5) 0.044(4) 0.034(3) 0.004(3) -0.001(4) 0.015(5) C12A 0.043(5) 0.044(4) 0.044(5) -0.001(3) 0.004(4) 0.003(4) C13A 0.048(7) 0.039(5) 0.062(7) 0.009(5) 0.005(5) 0.011(5) C8B 0.031(3) 0.036(3) 0.035(2) 0.002(2) -0.004(2) 0.003(2) C9B 0.039(11) 0.032(3) 0.035(3) 0.002(2) -0.001(5) 0.011(4) C10B 0.030(9) 0.047(6) 0.035(3) -0.001(4) -0.001(6) 0.007(5) C11B 0.035(5) 0.044(4) 0.034(3) 0.004(3) -0.001(4) 0.015(5) C12B 0.043(5) 0.044(4) 0.044(5) -0.001(3) 0.004(4) 0.003(4) C13B 0.049(11) 0.039(8) 0.044(9) 0.009(7) 0.006(7) 0.001(7) N1 0.030(2) 0.0222(19) 0.038(2) 0.0034(16) -0.0047(18) -0.0038(17) N2 0.039(3) 0.027(2) 0.033(2) 0.0004(16) -0.0090(18) -0.0031(18) Cl2 0.0406(8) 0.0524(7) 0.0377(6) 0.0085(6) -0.0109(6) -0.0008(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.699(5) . ? C1 C6 1.389(6) . ? C1 C2 1.390(6) . ? C1 H1A 0.9500 . ? C2 C3 1.383(6) . ? C2 H2A 0.9500 . ? C3 C4 1.382(6) . ? C3 Cl2 1.750(4) . ? C4 C5 1.389(6) . ? C4 H4 0.9500 . ? C5 C6 1.392(6) . ? C5 H5 0.9500 . ? C6 N1 1.419(5) . ? C7 N2 1.340(5) . ? C7 N1 1.363(5) . ? C8A N2 1.460(5) . ? C8A C9A 1.533(9) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A C10A 1.512(10) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A C11A 1.537(11) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C11A C12A 1.504(10) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A C13A 1.536(10) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C9B C10B 1.508(14) . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10B C11B 1.547(14) . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11B C12B 1.509(13) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B C13B 1.523(13) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.7(4) . . ? C6 C1 H1A 120.1 . . ? C2 C1 H1A 120.1 . . ? C3 C2 C1 119.9(4) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C4 C3 C2 121.0(4) . . ? C4 C3 Cl2 119.3(4) . . ? C2 C3 Cl2 119.8(3) . . ? C3 C4 C5 119.2(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.8(4) . . ? C1 C6 N1 123.0(4) . . ? C5 C6 N1 117.0(4) . . ? N2 C7 N1 112.8(4) . . ? N2 C7 S1 122.1(3) . . ? N1 C7 S1 125.1(3) . . ? N2 C8A C9A 112.2(6) . . ? N2 C8A H8A1 109.2 . . ? C9A C8A H8A1 109.2 . . ? N2 C8A H8A2 109.2 . . ? C9A C8A H8A2 109.2 . . ? H8A1 C8A H8A2 107.9 . . ? C10A C9A C8A 112.0(9) . . ? C10A C9A H9A1 109.2 . . ? C8A C9A H9A1 109.2 . . ? C10A C9A H9A2 109.2 . . ? C8A C9A H9A2 109.2 . . ? H9A1 C9A H9A2 107.9 . . ? C9A C10A C11A 112.7(10) . . ? C9A C10A H10A 109.1 . . ? C11A C10A H10A 109.1 . . ? C9A C10A H10B 109.1 . . ? C11A C10A H10B 109.1 . . ? H10A C10A H10B 107.8 . . ? C12A C11A C10A 114.6(8) . . ? C12A C11A H11A 108.6 . . ? C10A C11A H11A 108.6 . . ? C12A C11A H11B 108.6 . . ? C10A C11A H11B 108.6 . . ? H11A C11A H11B 107.6 . . ? C11A C12A C13A 111.9(7) . . ? C11A C12A H12A 109.2 . . ? C13A C12A H12A 109.2 . . ? C11A C12A H12B 109.2 . . ? C13A C12A H12B 109.2 . . ? H12A C12A H12B 107.9 . . ? C12A C13A H13A 109.5 . . ? C12A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C12A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C10B C9B H9B1 108.5 . . ? C10B C9B H9B2 108.5 . . ? H9B1 C9B H9B2 107.5 . . ? C9B C10B C11B 113.9(12) . . ? C9B C10B H10C 108.8 . . ? C11B C10B H10C 108.8 . . ? C9B C10B H10D 108.8 . . ? C11B C10B H10D 108.8 . . ? H10C C10B H10D 107.7 . . ? C12B C11B C10B 114.9(12) . . ? C12B C11B H11C 108.5 . . ? C10B C11B H11C 108.5 . . ? C12B C11B H11D 108.5 . . ? C10B C11B H11D 108.5 . . ? H11C C11B H11D 107.5 . . ? C11B C12B C13B 112.5(11) . . ? C11B C12B H12C 109.1 . . ? C13B C12B H12C 109.1 . . ? C11B C12B H12D 109.1 . . ? C13B C12B H12D 109.1 . . ? H12C C12B H12D 107.8 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C7 N1 C6 130.1(4) . . ? C7 N1 H1 115.0 . . ? C6 N1 H1 115.0 . . ? C7 N2 C8A 126.3(4) . . ? C7 N2 H2 116.9 . . ? C8A N2 H2 116.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.65 3.500(4) 163.1 8_665 N2 H2 S1 0.88 2.61 3.442(4) 158.9 8_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.271 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.058 #===END data_p-CN _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Marco Wenzel ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H19 N3 S' _chemical_formula_sum 'C14 H19 N3 S' _chemical_formula_weight 261.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.466(3) _cell_length_b 8.049(3) _cell_length_c 13.472(5) _cell_angle_alpha 82.276(9) _cell_angle_beta 82.154(10) _cell_angle_gamma 63.734(8) _cell_volume 716.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3323 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.7 _exptl_crystal_description 'platelet' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9626 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6649 _diffrn_reflns_av_R_equivalents 0.0820 _diffrn_reflns_av_sigmaI/netI 0.1232 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3271 _reflns_number_gt 2464 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1923P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3271 _refine_ls_number_parameters 179 _refine_ls_number_restraints 195 _refine_ls_R_factor_all 0.1143 _refine_ls_R_factor_gt 0.1018 _refine_ls_wR_factor_ref 0.2781 _refine_ls_wR_factor_gt 0.2625 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.97250(10) 0.00943(9) 0.66121(6) 0.0359(3) Uani 1 1 d . . . N1 N 0.5759(3) 0.1883(3) 0.70112(19) 0.0290(6) Uani 1 1 d . . . H1 H 0.4550 0.2499 0.6803 0.035 Uiso 1 1 calc R A 1 N2 N 0.6965(3) 0.1689(3) 0.53224(19) 0.0289(6) Uani 1 1 d . . . H2 H 0.8049 0.1424 0.4904 0.035 Uiso 1 1 calc R B . N3 N -0.1410(4) 0.5288(4) 0.2807(2) 0.0384(6) Uani 1 1 d . . . C6A C 0.5936(4) 0.1577(4) 0.8096(2) 0.0339(7) Uani 0.369(4) 1 d PDU B 1 H6A1 H 0.5971 0.2673 0.8334 0.041 Uiso 0.369(4) 1 calc PR B 1 H6A2 H 0.7213 0.0485 0.8236 0.041 Uiso 0.369(4) 1 calc PR B 1 C5A C 0.4087(11) 0.1233(9) 0.8710(6) 0.0321(9) Uani 0.369(4) 1 d PDU B 1 H5A1 H 0.4089 0.1297 0.9438 0.039 Uiso 0.369(4) 1 calc PR B 1 H5A2 H 0.2797 0.2204 0.8484 0.039 Uiso 0.369(4) 1 calc PR B 1 C4A C 0.433(3) -0.069(3) 0.851(2) 0.0370(19) Uani 0.369(4) 1 d PDU B 1 H4A1 H 0.4303 -0.0734 0.7785 0.044 Uiso 0.369(4) 1 calc PR B 1 H4A2 H 0.5645 -0.1646 0.8716 0.044 Uiso 0.369(4) 1 calc PR B 1 C3A C 0.2684(14) -0.1159(11) 0.9084(7) 0.0383(10) Uani 0.369(4) 1 d PDU B 1 H3A1 H 0.2695 -0.1081 0.9811 0.046 Uiso 0.369(4) 1 calc PR B 1 H3A2 H 0.1374 -0.0205 0.8873 0.046 Uiso 0.369(4) 1 calc PR B 1 C2A C 0.285(2) -0.3039(17) 0.8940(12) 0.078(2) Uani 0.369(4) 1 d PDU B 1 H2A1 H 0.4167 -0.4001 0.9136 0.094 Uiso 0.369(4) 1 calc PR B 1 H2A2 H 0.2785 -0.3112 0.8219 0.094 Uiso 0.369(4) 1 calc PR B 1 C1A C 0.117(4) -0.346(4) 0.956(2) 0.060(3) Uani 0.369(4) 1 d PDU B 1 H1A1 H 0.1259 -0.4635 0.9382 0.091 Uiso 0.369(4) 1 calc PR B 1 H1A2 H -0.0136 -0.2454 0.9419 0.091 Uiso 0.369(4) 1 calc PR B 1 H1A3 H 0.1342 -0.3565 1.0280 0.091 Uiso 0.369(4) 1 calc PR B 1 C6B C 0.5936(4) 0.1577(4) 0.8096(2) 0.0339(7) Uani 0.631(4) 1 d PDU B 2 H6B1 H 0.4779 0.2573 0.8439 0.041 Uiso 0.631(4) 1 calc PR B 2 H6B2 H 0.7173 0.1633 0.8238 0.041 Uiso 0.631(4) 1 calc PR B 2 C5B C 0.6000(7) -0.0315(5) 0.8505(4) 0.0321(9) Uani 0.631(4) 1 d PDU B 2 H5B1 H 0.6362 -0.0588 0.9208 0.039 Uiso 0.631(4) 1 calc PR B 2 H5B2 H 0.7049 -0.1293 0.8103 0.039 Uiso 0.631(4) 1 calc PR B 2 C4B C 0.3978(16) -0.0363(13) 0.8472(10) 0.0370(19) Uani 0.631(4) 1 d PDU B 2 H4B1 H 0.2894 0.0778 0.8740 0.044 Uiso 0.631(4) 1 calc PR B 2 H4B2 H 0.3761 -0.0363 0.7763 0.044 Uiso 0.631(4) 1 calc PR B 2 C3B C 0.3842(8) -0.2056(7) 0.9074(4) 0.0383(10) Uani 0.631(4) 1 d PDU B 2 H3B1 H 0.4926 -0.3197 0.8806 0.046 Uiso 0.631(4) 1 calc PR B 2 H3B2 H 0.4062 -0.2057 0.9783 0.046 Uiso 0.631(4) 1 calc PR B 2 C2B C 0.1887(13) -0.2104(12) 0.9043(7) 0.078(2) Uani 0.631(4) 1 d PDU B 2 H2B1 H 0.1755 -0.2272 0.8347 0.094 Uiso 0.631(4) 1 calc PR B 2 H2B2 H 0.0799 -0.0888 0.9220 0.094 Uiso 0.631(4) 1 calc PR B 2 C1B C 0.159(2) -0.366(2) 0.9760(11) 0.060(3) Uani 0.631(4) 1 d PDU B 2 H1B1 H 0.0261 -0.3587 0.9706 0.091 Uiso 0.631(4) 1 calc PR B 2 H1B2 H 0.1706 -0.3506 1.0454 0.091 Uiso 0.631(4) 1 calc PR B 2 H1B3 H 0.2622 -0.4879 0.9573 0.091 Uiso 0.631(4) 1 calc PR B 2 C7 C 0.7310(4) 0.1290(3) 0.6317(2) 0.0284(6) Uani 1 1 d . B . C8 C 0.5145(4) 0.2459(3) 0.4857(2) 0.0285(6) Uani 1 1 d . B . C9 C 0.5130(4) 0.3473(3) 0.3926(2) 0.0297(6) Uani 1 1 d . . . H9 H 0.6272 0.3677 0.3667 0.036 Uiso 1 1 calc R B . C10 C 0.3466(4) 0.4184(4) 0.3378(2) 0.0319(7) Uani 1 1 d . B . H10 H 0.3463 0.4869 0.2746 0.038 Uiso 1 1 calc R . . C11 C 0.1790(4) 0.3878(3) 0.3770(2) 0.0301(6) Uani 1 1 d . . . C12 C 0.1801(4) 0.2871(3) 0.4692(2) 0.0302(6) Uani 1 1 d . B . H12 H 0.0655 0.2674 0.4952 0.036 Uiso 1 1 calc R . . C13 C 0.3472(4) 0.2148(3) 0.5238(2) 0.0286(6) Uani 1 1 d . . . H13 H 0.3478 0.1448 0.5865 0.034 Uiso 1 1 calc R B . C14 C 0.0012(4) 0.4654(4) 0.3218(2) 0.0330(7) Uani 1 1 d . B . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0199(4) 0.0200(4) 0.0608(6) -0.0135(3) -0.0118(3) 0.0029(3) N1 0.0206(11) 0.0126(9) 0.0491(16) -0.0053(8) -0.0103(9) -0.0001(8) N2 0.0186(11) 0.0141(10) 0.0501(16) -0.0122(9) -0.0042(9) -0.0005(8) N3 0.0238(13) 0.0327(13) 0.0548(18) -0.0171(11) -0.0066(10) -0.0039(11) C6A 0.0324(15) 0.0211(12) 0.0477(19) -0.0039(11) -0.0116(12) -0.0086(11) C5A 0.033(2) 0.0130(15) 0.041(2) -0.0051(13) -0.0086(15) 0.0000(15) C4A 0.038(4) 0.020(4) 0.052(2) 0.001(3) -0.019(3) -0.008(4) C3A 0.050(3) 0.022(2) 0.044(3) -0.0030(18) -0.018(2) -0.0128(17) C2A 0.091(5) 0.063(4) 0.111(5) 0.041(4) -0.059(4) -0.059(4) C1A 0.070(6) 0.034(4) 0.084(7) 0.016(3) -0.025(4) -0.030(5) C6B 0.0324(15) 0.0211(12) 0.0477(19) -0.0039(11) -0.0116(12) -0.0086(11) C5B 0.033(2) 0.0130(15) 0.041(2) -0.0051(13) -0.0086(15) 0.0000(15) C4B 0.038(4) 0.020(4) 0.052(2) 0.001(3) -0.019(3) -0.008(4) C3B 0.050(3) 0.022(2) 0.044(3) -0.0030(18) -0.018(2) -0.0128(17) C2B 0.091(5) 0.063(4) 0.111(5) 0.041(4) -0.059(4) -0.059(4) C1B 0.070(6) 0.034(4) 0.084(7) 0.016(3) -0.025(4) -0.030(5) C7 0.0218(13) 0.0088(10) 0.0518(19) -0.0091(9) -0.0081(11) -0.0010(9) C8 0.0197(13) 0.0101(10) 0.0512(18) -0.0132(10) -0.0053(10) 0.0012(10) C9 0.0208(13) 0.0153(11) 0.0513(18) -0.0122(10) -0.0046(11) -0.0033(10) C10 0.0266(14) 0.0175(11) 0.0493(19) -0.0101(10) -0.0075(11) -0.0042(11) C11 0.0204(13) 0.0152(11) 0.0517(19) -0.0151(10) -0.0068(11) -0.0005(10) C12 0.0188(12) 0.0160(11) 0.0536(19) -0.0152(10) -0.0043(11) -0.0019(10) C13 0.0213(13) 0.0134(10) 0.0491(18) -0.0137(10) -0.0052(11) -0.0023(10) C14 0.0255(14) 0.0216(12) 0.0480(18) -0.0159(11) -0.0031(11) -0.0029(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.700(3) . ? N1 C7 1.334(4) . ? N1 C6A 1.463(4) . ? N1 H1 0.8800 . ? N2 C7 1.368(4) . ? N2 C8 1.416(3) . ? N2 H2 0.8800 . ? N3 C14 1.139(4) . ? C6A C5A 1.622(8) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C5A C4A 1.535(16) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C4A C3A 1.519(15) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C3A C2A 1.501(12) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C2A C1A 1.546(16) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C5B C4B 1.534(10) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C4B C3B 1.526(9) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C3B C2B 1.484(8) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C2B C1B 1.554(9) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C1B H1B1 0.9800 . ? C1B H1B2 0.9800 . ? C1B H1B3 0.9800 . ? C8 C13 1.397(4) . ? C8 C9 1.400(4) . ? C9 C10 1.387(4) . ? C9 H9 0.9500 . ? C10 C11 1.402(4) . ? C10 H10 0.9500 . ? C11 C12 1.388(4) . ? C11 C14 1.455(4) . ? C12 C13 1.389(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C6A 124.3(2) . . ? C7 N1 H1 117.9 . . ? C6A N1 H1 117.9 . . ? C7 N2 C8 130.5(2) . . ? C7 N2 H2 114.7 . . ? C8 N2 H2 114.7 . . ? N1 C6A C5A 111.9(3) . . ? N1 C6A H6A1 109.2 . . ? C5A C6A H6A1 109.2 . . ? N1 C6A H6A2 109.2 . . ? C5A C6A H6A2 109.2 . . ? H6A1 C6A H6A2 107.9 . . ? C4A C5A C6A 108.7(8) . . ? C4A C5A H5A1 110.0 . . ? C6A C5A H5A1 110.0 . . ? C4A C5A H5A2 110.0 . . ? C6A C5A H5A2 110.0 . . ? H5A1 C5A H5A2 108.3 . . ? C3A C4A C5A 112.4(15) . . ? C3A C4A H4A1 109.1 . . ? C5A C4A H4A1 109.1 . . ? C3A C4A H4A2 109.1 . . ? C5A C4A H4A2 109.1 . . ? H4A1 C4A H4A2 107.9 . . ? C2A C3A C4A 115.1(11) . . ? C2A C3A H3A1 108.5 . . ? C4A C3A H3A1 108.5 . . ? C2A C3A H3A2 108.5 . . ? C4A C3A H3A2 108.5 . . ? H3A1 C3A H3A2 107.5 . . ? C3A C2A C1A 112.9(17) . . ? C3A C2A H2A1 109.0 . . ? C1A C2A H2A1 109.0 . . ? C3A C2A H2A2 109.0 . . ? C1A C2A H2A2 109.0 . . ? H2A1 C2A H2A2 107.8 . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C4B C5B H5B1 109.3 . . ? C4B C5B H5B2 109.3 . . ? H5B1 C5B H5B2 107.9 . . ? C3B C4B C5B 113.1(8) . . ? C3B C4B H4B1 109.0 . . ? C5B C4B H4B1 109.0 . . ? C3B C4B H4B2 109.0 . . ? C5B C4B H4B2 109.0 . . ? H4B1 C4B H4B2 107.8 . . ? C2B C3B C4B 113.2(6) . . ? C2B C3B H3B1 108.9 . . ? C4B C3B H3B1 108.9 . . ? C2B C3B H3B2 108.9 . . ? C4B C3B H3B2 108.9 . . ? H3B1 C3B H3B2 107.8 . . ? C3B C2B C1B 114.5(6) . . ? C3B C2B H2B1 108.6 . . ? C1B C2B H2B1 108.6 . . ? C3B C2B H2B2 108.6 . . ? C1B C2B H2B2 108.6 . . ? H2B1 C2B H2B2 107.6 . . ? C2B C1B H1B1 109.5 . . ? C2B C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C2B C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? N1 C7 N2 119.1(2) . . ? N1 C7 S1 122.8(2) . . ? N2 C7 S1 118.1(2) . . ? C13 C8 C9 119.8(2) . . ? C13 C8 N2 123.9(3) . . ? C9 C8 N2 116.2(2) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.0(3) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 C14 119.8(2) . . ? C10 C11 C14 119.8(3) . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 119.5(3) . . ? C12 C13 H13 120.3 . . ? C8 C13 H13 120.3 . . ? N3 C14 C11 178.1(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C6A C5A -144.3(3) . . . . ? N1 C6A C5A C4A 71.6(12) . . . . ? C6A C5A C4A C3A 178.4(13) . . . . ? C5A C4A C3A C2A -179.0(13) . . . . ? C4A C3A C2A C1A 178.3(16) . . . . ? C5B C4B C3B C2B 179.9(8) . . . . ? C4B C3B C2B C1B -172.3(11) . . . . ? C6A N1 C7 N2 -178.8(2) . . . . ? C6A N1 C7 S1 -0.3(3) . . . . ? C8 N2 C7 N1 -9.5(4) . . . . ? C8 N2 C7 S1 171.9(2) . . . . ? C7 N2 C8 C13 -33.3(4) . . . . ? C7 N2 C8 C9 151.4(3) . . . . ? C13 C8 C9 C10 0.3(4) . . . . ? N2 C8 C9 C10 175.9(2) . . . . ? C8 C9 C10 C11 0.2(4) . . . . ? C9 C10 C11 C12 -0.3(4) . . . . ? C9 C10 C11 C14 178.4(2) . . . . ? C10 C11 C12 C13 -0.2(4) . . . . ? C14 C11 C12 C13 -178.8(2) . . . . ? C11 C12 C13 C8 0.7(4) . . . . ? C9 C8 C13 C12 -0.8(4) . . . . ? N2 C8 C13 C12 -175.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.88 2.27 3.029(3) 144.0 2_566 N2 H2 S1 0.88 2.52 3.327(3) 152.0 2_756 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.929 _refine_diff_density_min -1.303 _refine_diff_density_rms 0.134 #===END data_p-COCF3 _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Jennifer R. Hiscock ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H19 F3 N2 O S' _chemical_formula_sum 'C15 H19 F3 N2 O S' _chemical_formula_weight 332.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2392(4) _cell_length_b 11.0200(9) _cell_length_c 14.5788(11) _cell_angle_alpha 75.946(5) _cell_angle_beta 79.884(6) _cell_angle_gamma 79.501(6) _cell_volume 795.20(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7183 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9388 _exptl_absorpt_correction_T_max 0.9953 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7651 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3632 _reflns_number_gt 3230 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.3403P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3632 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0952 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.03970(6) 0.05271(3) 0.13070(2) 0.01717(10) Uani 1 1 d . . . C1 C -1.1141(3) 0.45002(14) -0.29474(10) 0.0203(3) Uani 1 1 d . . . C2 C -1.0393(3) 0.48475(13) -0.20741(9) 0.0177(3) Uani 1 1 d . . . C3 C -0.8567(3) 0.39218(12) -0.15046(9) 0.0155(3) Uani 1 1 d . . . C4 C -0.7812(3) 0.26669(12) -0.15929(9) 0.0161(3) Uani 1 1 d . . . H4 H -0.8506 0.2365 -0.2041 0.019 Uiso 1 1 calc R . . C5 C -0.6066(3) 0.18646(12) -0.10329(9) 0.0158(3) Uani 1 1 d . . . H5 H -0.5593 0.1009 -0.1089 0.019 Uiso 1 1 calc R . . C6 C -0.4985(2) 0.22987(12) -0.03828(9) 0.0144(3) Uani 1 1 d . . . C7 C -0.5706(3) 0.35575(13) -0.02995(9) 0.0180(3) Uani 1 1 d . . . H7 H -0.4968 0.3866 0.0134 0.022 Uiso 1 1 calc R . . C8 C -0.7491(3) 0.43505(13) -0.08488(10) 0.0185(3) Uani 1 1 d . . . H8 H -0.7998 0.5200 -0.0781 0.022 Uiso 1 1 calc R . . C9 C -0.2431(3) 0.14221(12) 0.09921(9) 0.0153(3) Uani 1 1 d . . . C10 C -0.3712(3) 0.21616(14) 0.25149(10) 0.0218(3) Uani 1 1 d . . . H10A H -0.4012 0.3059 0.2563 0.026 Uiso 1 1 calc R . . H10B H -0.1885 0.1807 0.2623 0.026 Uiso 1 1 calc R . . C11 C -0.5594(3) 0.14359(14) 0.32795(10) 0.0232(3) Uani 1 1 d . . . H11A H -0.5558 0.1651 0.3898 0.028 Uiso 1 1 calc R . . H11B H -0.7396 0.1713 0.3115 0.028 Uiso 1 1 calc R . . C12 C -0.4953(3) 0.00121(14) 0.33937(10) 0.0223(3) Uani 1 1 d . . . H12A H -0.3163 -0.0268 0.3569 0.027 Uiso 1 1 calc R . . H12B H -0.4962 -0.0202 0.2773 0.027 Uiso 1 1 calc R . . C13 C -0.6865(3) -0.07076(15) 0.41475(10) 0.0251(3) Uani 1 1 d . . . H13A H -0.7003 -0.0426 0.4752 0.030 Uiso 1 1 calc R . . H13B H -0.8621 -0.0502 0.3938 0.030 Uiso 1 1 calc R . . C14 C -0.6032(3) -0.21257(16) 0.43270(11) 0.0299(3) Uani 1 1 d . . . H14A H -0.4297 -0.2328 0.4553 0.036 Uiso 1 1 calc R . . H14B H -0.5833 -0.2398 0.3716 0.036 Uiso 1 1 calc R . . C15 C -0.7945(4) -0.28763(19) 0.50555(14) 0.0404(4) Uani 1 1 d . . . H15A H -0.7292 -0.3782 0.5134 0.061 Uiso 1 1 calc R . . H15B H -0.9662 -0.2696 0.4832 0.061 Uiso 1 1 calc R . . H15C H -0.8113 -0.2634 0.5669 0.061 Uiso 1 1 calc R . . N1 N -0.3092(2) 0.14563(10) 0.01188(8) 0.0153(2) Uani 1 1 d . . . H1 H -0.2203 0.0864 -0.0171 0.018 Uiso 1 1 calc R . . N2 N -0.4078(2) 0.20854(11) 0.15570(8) 0.0198(3) Uani 1 1 d . . . H2 H -0.5513 0.2516 0.1337 0.024 Uiso 1 1 calc R . . O1 O -1.1326(2) 0.58772(10) -0.19152(8) 0.0257(2) Uani 1 1 d . . . F1 F -1.2616(2) 0.54608(9) -0.34398(7) 0.0338(2) Uani 1 1 d . . . F2 F -0.90236(17) 0.41751(9) -0.35379(6) 0.0273(2) Uani 1 1 d . . . F3 F -1.24867(18) 0.35233(9) -0.26731(7) 0.0303(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01466(16) 0.01846(17) 0.01810(17) -0.00578(12) -0.00435(12) 0.00277(12) C1 0.0195(7) 0.0215(7) 0.0191(6) -0.0042(5) -0.0052(5) 0.0014(5) C2 0.0161(6) 0.0179(6) 0.0188(6) -0.0040(5) -0.0031(5) -0.0011(5) C3 0.0148(6) 0.0146(6) 0.0163(6) -0.0027(5) -0.0025(5) -0.0010(5) C4 0.0163(6) 0.0166(6) 0.0164(6) -0.0048(5) -0.0028(5) -0.0032(5) C5 0.0172(6) 0.0122(6) 0.0176(6) -0.0037(5) -0.0014(5) -0.0017(5) C6 0.0136(6) 0.0139(6) 0.0140(6) -0.0012(4) -0.0012(5) -0.0011(5) C7 0.0216(7) 0.0156(6) 0.0186(6) -0.0056(5) -0.0072(5) -0.0009(5) C8 0.0216(7) 0.0129(6) 0.0219(6) -0.0058(5) -0.0058(5) 0.0006(5) C9 0.0156(6) 0.0131(6) 0.0171(6) -0.0028(5) -0.0026(5) -0.0020(5) C10 0.0236(7) 0.0222(7) 0.0204(7) -0.0096(5) -0.0068(5) 0.0046(6) C11 0.0222(7) 0.0283(8) 0.0182(6) -0.0085(5) -0.0041(5) 0.0043(6) C12 0.0194(7) 0.0274(8) 0.0201(7) -0.0079(6) -0.0024(5) -0.0003(6) C13 0.0194(7) 0.0358(9) 0.0206(7) -0.0080(6) -0.0020(5) -0.0036(6) C14 0.0328(8) 0.0329(9) 0.0271(8) -0.0112(6) -0.0009(6) -0.0093(7) C15 0.0408(10) 0.0459(11) 0.0375(10) -0.0079(8) -0.0014(8) -0.0196(8) N1 0.0165(5) 0.0134(5) 0.0155(5) -0.0045(4) -0.0037(4) 0.0022(4) N2 0.0182(6) 0.0230(6) 0.0168(5) -0.0063(4) -0.0059(4) 0.0062(5) O1 0.0287(6) 0.0198(5) 0.0291(5) -0.0086(4) -0.0127(4) 0.0075(4) F1 0.0397(5) 0.0331(5) 0.0276(5) -0.0088(4) -0.0196(4) 0.0153(4) F2 0.0273(5) 0.0320(5) 0.0197(4) -0.0078(3) 0.0002(3) 0.0023(4) F3 0.0292(5) 0.0370(5) 0.0302(5) -0.0071(4) -0.0093(4) -0.0142(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C9 1.6928(13) . ? C1 F1 1.3269(16) . ? C1 F2 1.3302(16) . ? C1 F3 1.3358(17) . ? C1 C2 1.5452(19) . ? C2 O1 1.2108(17) . ? C2 C3 1.4688(18) . ? C3 C4 1.3982(18) . ? C3 C8 1.4001(19) . ? C4 C5 1.3793(19) . ? C4 H4 0.9500 . ? C5 C6 1.3985(19) . ? C5 H5 0.9500 . ? C6 C7 1.3987(18) . ? C6 N1 1.4032(16) . ? C7 C8 1.3802(19) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N2 1.3305(17) . ? C9 N1 1.3672(17) . ? C10 N2 1.4666(17) . ? C10 C11 1.524(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.523(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.515(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.523(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C1 F2 107.68(11) . . ? F1 C1 F3 107.77(12) . . ? F2 C1 F3 107.61(12) . . ? F1 C1 C2 111.50(12) . . ? F2 C1 C2 111.36(11) . . ? F3 C1 C2 110.75(11) . . ? O1 C2 C3 124.42(13) . . ? O1 C2 C1 117.49(12) . . ? C3 C2 C1 118.08(11) . . ? C4 C3 C8 118.83(12) . . ? C4 C3 C2 124.27(12) . . ? C8 C3 C2 116.89(12) . . ? C5 C4 C3 120.35(12) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.62(12) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C7 119.30(12) . . ? C5 C6 N1 117.63(11) . . ? C7 C6 N1 122.95(12) . . ? C8 C7 C6 119.86(12) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C3 121.02(12) . . ? C7 C8 H8 119.5 . . ? C3 C8 H8 119.5 . . ? N2 C9 N1 117.85(12) . . ? N2 C9 S1 123.41(10) . . ? N1 C9 S1 118.73(10) . . ? N2 C10 C11 111.09(12) . . ? N2 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? N2 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 113.49(11) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 113.28(12) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 112.51(12) . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 113.85(14) . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 N1 C6 129.35(11) . . ? C9 N1 H1 115.3 . . ? C6 N1 H1 115.3 . . ? C9 N2 C10 125.72(12) . . ? C9 N2 H2 117.1 . . ? C10 N2 H2 117.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 O1 4.25(18) . . . . ? F2 C1 C2 O1 124.55(13) . . . . ? F3 C1 C2 O1 -115.75(14) . . . . ? F1 C1 C2 C3 -174.62(11) . . . . ? F2 C1 C2 C3 -54.32(16) . . . . ? F3 C1 C2 C3 65.38(15) . . . . ? O1 C2 C3 C4 169.51(13) . . . . ? C1 C2 C3 C4 -11.70(19) . . . . ? O1 C2 C3 C8 -11.9(2) . . . . ? C1 C2 C3 C8 166.89(12) . . . . ? C8 C3 C4 C5 0.87(19) . . . . ? C2 C3 C4 C5 179.44(12) . . . . ? C3 C4 C5 C6 -1.26(19) . . . . ? C4 C5 C6 C7 0.44(19) . . . . ? C4 C5 C6 N1 -175.91(11) . . . . ? C5 C6 C7 C8 0.76(19) . . . . ? N1 C6 C7 C8 176.90(12) . . . . ? C6 C7 C8 C3 -1.2(2) . . . . ? C4 C3 C8 C7 0.3(2) . . . . ? C2 C3 C8 C7 -178.34(12) . . . . ? N2 C10 C11 C12 70.22(15) . . . . ? C10 C11 C12 C13 -179.08(12) . . . . ? C11 C12 C13 C14 -173.82(13) . . . . ? C12 C13 C14 C15 -178.23(14) . . . . ? N2 C9 N1 C6 15.5(2) . . . . ? S1 C9 N1 C6 -165.47(10) . . . . ? C5 C6 N1 C9 -153.53(13) . . . . ? C7 C6 N1 C9 30.3(2) . . . . ? N1 C9 N2 C10 179.79(12) . . . . ? S1 C9 N2 C10 0.8(2) . . . . ? C11 C10 N2 C9 -108.18(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.48 3.3380(11) 165.4 2 N2 H2 O1 0.88 2.40 3.0444(15) 130.4 2_365 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.387 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.056 #===END data_p-COMe _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Jennifer R. Hiscock ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 N2 O S' _chemical_formula_sum 'C15 H22 N2 O S' _chemical_formula_weight 278.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.756(6) _cell_length_b 10.120(7) _cell_length_c 37.38(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2934(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5101 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 31.1 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9664 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Left)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12353 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.1033 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2507 _reflns_number_gt 2098 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Data completeness only 89.8%, but this is sufficient for proof of structure and hydrogen bonding network ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1002P)^2^+6.6631P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2507 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.2504 _refine_ls_wR_factor_gt 0.2373 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7688(8) -0.0203(6) -0.05283(12) 0.0435(14) Uani 1 1 d . . . H1A H 0.7708 0.0112 -0.0776 0.065 Uiso 1 1 calc R . . H1B H 0.6724 -0.0818 -0.0496 0.065 Uiso 1 1 calc R . . H1C H 0.8774 -0.0657 -0.0474 0.065 Uiso 1 1 calc R . . C2 C 0.7470(7) 0.0963(5) -0.02772(11) 0.0382(12) Uani 1 1 d . . . H2A H 0.6388 0.1431 -0.0338 0.046 Uiso 1 1 calc R . . H2B H 0.8437 0.1587 -0.0314 0.046 Uiso 1 1 calc R . . C3 C 0.7418(7) 0.0553(5) 0.01192(10) 0.0318(11) Uani 1 1 d . . . H3A H 0.6436 -0.0056 0.0157 0.038 Uiso 1 1 calc R . . H3B H 0.8489 0.0067 0.0178 0.038 Uiso 1 1 calc R . . C4 C 0.7240(7) 0.1720(5) 0.03737(11) 0.0367(12) Uani 1 1 d . . . H4A H 0.6195 0.2228 0.0309 0.044 Uiso 1 1 calc R . . H4B H 0.8248 0.2309 0.0344 0.044 Uiso 1 1 calc R . . C5 C 0.7112(6) 0.1300(5) 0.07685(11) 0.0322(11) Uani 1 1 d . . . H5A H 0.6176 0.0642 0.0795 0.039 Uiso 1 1 calc R . . H5B H 0.8206 0.0872 0.0841 0.039 Uiso 1 1 calc R . . C6 C 0.6758(6) 0.2463(5) 0.10156(10) 0.0328(11) Uani 1 1 d . . . H6A H 0.7689 0.3126 0.0994 0.039 Uiso 1 1 calc R . . H6B H 0.5653 0.2889 0.0950 0.039 Uiso 1 1 calc R . . C7 C 0.6416(6) 0.2714(5) 0.16748(10) 0.0271(11) Uani 1 1 d . . . C8 C 0.6389(6) 0.2394(5) 0.23489(10) 0.0251(10) Uani 1 1 d . . . C9 C 0.7128(6) 0.1515(5) 0.26007(10) 0.0267(10) Uani 1 1 d . . . H9 H 0.7712 0.0744 0.2521 0.032 Uiso 1 1 calc R . . C10 C 0.7000(6) 0.1779(5) 0.29648(11) 0.0306(11) Uani 1 1 d . . . H10 H 0.7500 0.1185 0.3132 0.037 Uiso 1 1 calc R . . C11 C 0.6150(6) 0.2902(5) 0.30869(11) 0.0271(10) Uani 1 1 d . . . C12 C 0.5376(6) 0.3738(5) 0.28334(11) 0.0290(10) Uani 1 1 d . . . H12 H 0.4782 0.4504 0.2914 0.035 Uiso 1 1 calc R . . C13 C 0.5456(6) 0.3478(5) 0.24683(11) 0.0274(10) Uani 1 1 d . . . H13 H 0.4878 0.4035 0.2303 0.033 Uiso 1 1 calc R . . C14 C 0.6048(6) 0.3286(5) 0.34745(12) 0.0315(11) Uani 1 1 d . . . C15 C 0.6691(6) 0.2293(5) 0.37476(11) 0.0331(11) Uani 1 1 d . . . H15A H 0.6553 0.2658 0.3989 0.050 Uiso 1 1 calc R . . H15B H 0.7912 0.2105 0.3704 0.050 Uiso 1 1 calc R . . H15C H 0.6023 0.1474 0.3727 0.050 Uiso 1 1 calc R . . N1 N 0.6671(5) 0.1969(4) 0.13849(9) 0.0330(10) Uani 1 1 d . . . H1 H 0.6796 0.1113 0.1418 0.040 Uiso 1 1 calc R . . N2 N 0.6626(5) 0.2027(4) 0.19874(8) 0.0268(9) Uani 1 1 d . . . H2 H 0.6972 0.1206 0.1958 0.032 Uiso 1 1 calc R . . S1 S 0.58922(15) 0.43388(13) 0.16402(3) 0.0303(4) Uani 1 1 d . . . O1 O 0.5448(5) 0.4348(4) 0.35694(8) 0.0381(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.051(3) 0.042(3) 0.037(2) -0.007(2) -0.002(2) 0.009(3) C2 0.039(3) 0.037(3) 0.039(2) -0.001(2) 0.0045(19) -0.002(3) C3 0.031(3) 0.031(3) 0.034(2) -0.0032(18) -0.0010(18) -0.002(2) C4 0.039(3) 0.038(3) 0.033(2) -0.0002(19) 0.0011(19) -0.001(3) C5 0.033(3) 0.032(3) 0.031(2) -0.0001(17) 0.0010(18) 0.001(2) C6 0.035(3) 0.035(3) 0.028(2) 0.0041(17) 0.0025(18) -0.002(2) C7 0.024(3) 0.029(3) 0.028(2) 0.0020(16) 0.0015(15) -0.001(2) C8 0.018(2) 0.030(3) 0.028(2) -0.0002(16) -0.0003(15) -0.002(2) C9 0.027(3) 0.019(2) 0.034(2) -0.0011(15) 0.0007(16) 0.000(2) C10 0.023(3) 0.038(3) 0.032(2) 0.0026(18) -0.0007(17) -0.003(2) C11 0.024(2) 0.026(3) 0.032(2) -0.0004(17) -0.0002(16) -0.004(2) C12 0.021(2) 0.031(3) 0.035(2) -0.0048(17) 0.0008(17) -0.002(2) C13 0.020(2) 0.028(3) 0.034(2) 0.0037(18) -0.0005(17) 0.000(2) C14 0.023(3) 0.036(3) 0.035(2) -0.0023(19) 0.0005(17) -0.008(2) C15 0.033(3) 0.039(3) 0.028(2) 0.0015(17) -0.0013(17) -0.005(3) N1 0.045(3) 0.024(2) 0.0301(19) 0.0034(15) 0.0019(16) 0.005(2) N2 0.031(2) 0.019(2) 0.0301(18) -0.0004(13) 0.0026(14) -0.0021(19) S1 0.0326(8) 0.0265(7) 0.0318(6) 0.0015(4) -0.0006(4) -0.0005(6) O1 0.045(2) 0.038(2) 0.0315(17) -0.0046(13) 0.0002(14) 0.0070(18) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.518(7) . ? C2 C3 1.540(6) . ? C3 C4 1.522(6) . ? C4 C5 1.539(6) . ? C5 C6 1.521(6) . ? C6 N1 1.470(5) . ? C7 N1 1.335(5) . ? C7 N2 1.370(5) . ? C7 S1 1.698(5) . ? C8 C13 1.388(6) . ? C8 N2 1.413(5) . ? C8 C9 1.417(6) . ? C9 C10 1.390(6) . ? C10 C11 1.391(7) . ? C11 C12 1.405(6) . ? C11 C14 1.502(6) . ? C12 C13 1.391(6) . ? C14 O1 1.223(6) . ? C14 C15 1.517(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 112.9(4) . . ? C4 C3 C2 113.3(4) . . ? C3 C4 C5 113.0(4) . . ? C6 C5 C4 112.4(4) . . ? N1 C6 C5 108.4(4) . . ? N1 C7 N2 112.8(4) . . ? N1 C7 S1 121.4(3) . . ? N2 C7 S1 125.8(3) . . ? C13 C8 N2 125.7(4) . . ? C13 C8 C9 119.6(4) . . ? N2 C8 C9 114.7(4) . . ? C10 C9 C8 120.1(4) . . ? C9 C10 C11 120.8(4) . . ? C10 C11 C12 118.3(4) . . ? C10 C11 C14 123.6(4) . . ? C12 C11 C14 118.2(4) . . ? C13 C12 C11 121.9(4) . . ? C8 C13 C12 119.3(4) . . ? O1 C14 C11 121.8(4) . . ? O1 C14 C15 120.8(4) . . ? C11 C14 C15 117.4(4) . . ? C7 N1 C6 125.3(4) . . ? C7 N2 C8 131.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C2 C3 C4 178.7(4) . . . . ? C2 C3 C4 C5 177.6(4) . . . . ? C3 C4 C5 C6 -174.3(4) . . . . ? C4 C5 C6 N1 -179.6(4) . . . . ? C13 C8 C9 C10 -3.6(7) . . . . ? N2 C8 C9 C10 179.2(4) . . . . ? C8 C9 C10 C11 0.1(7) . . . . ? C9 C10 C11 C12 2.0(7) . . . . ? C9 C10 C11 C14 -176.5(4) . . . . ? C10 C11 C12 C13 -0.6(7) . . . . ? C14 C11 C12 C13 178.0(4) . . . . ? N2 C8 C13 C12 -178.1(4) . . . . ? C9 C8 C13 C12 5.0(7) . . . . ? C11 C12 C13 C8 -3.0(7) . . . . ? C10 C11 C14 O1 172.2(5) . . . . ? C12 C11 C14 O1 -6.3(7) . . . . ? C10 C11 C14 C15 -8.9(7) . . . . ? C12 C11 C14 C15 172.6(4) . . . . ? N2 C7 N1 C6 -171.6(4) . . . . ? S1 C7 N1 C6 8.3(7) . . . . ? C5 C6 N1 C7 178.4(4) . . . . ? N1 C7 N2 C8 -175.8(4) . . . . ? S1 C7 N2 C8 4.3(7) . . . . ? C13 C8 N2 C7 17.5(8) . . . . ? C9 C8 N2 C7 -165.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 2.50 3.125(6) 129.1 3_645 N1 H1 S1 0.88 2.67 3.401(4) 141.2 8_755 N2 H2 S1 0.88 2.78 3.576(4) 151.3 8_755 _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.897 _refine_diff_density_max 0.384 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.080 #===END data_p-COOMe _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 N2 O2 S' _chemical_formula_sum 'C15 H22 N2 O2 S' _chemical_formula_weight 294.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0875(8) _cell_length_b 7.4703(6) _cell_length_c 37.579(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.356(7) _cell_angle_gamma 90.00 _cell_volume 3061.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7813 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9915 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Left)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10229 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.1302 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5045 _reflns_number_gt 2789 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Data completeness only 93.5%, but this is sufficient for proof of structure and hydrogen bonding network ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1156P)^2^+3.3397P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5045 _refine_ls_number_parameters 365 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1527 _refine_ls_R_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.2537 _refine_ls_wR_factor_gt 0.2149 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.69171(13) 0.37202(18) 0.25588(4) 0.0215(4) Uani 1 1 d . . . O1 O 0.6407(3) 0.2784(6) 0.06658(11) 0.0270(10) Uani 1 1 d . . . O2 O 0.4370(4) 0.2997(6) 0.05060(13) 0.0393(12) Uani 1 1 d . . . N1 N 0.4967(4) 0.1795(6) 0.22122(14) 0.0227(12) Uani 1 1 d . . . H1 H 0.4324 0.1147 0.2236 0.027 Uiso 1 1 calc R . . N2 N 0.5271(4) 0.1753(6) 0.28238(14) 0.0218(11) Uani 1 1 d . . . H2 H 0.4680 0.0951 0.2785 0.026 Uiso 1 1 calc R . . C1 C 0.6488(6) 0.2933(9) 0.02799(18) 0.0313(16) Uani 1 1 d . . . H1A H 0.6041 0.1940 0.0146 0.047 Uiso 1 1 calc R . . H1B H 0.7350 0.2888 0.0253 0.047 Uiso 1 1 calc R . . H1C H 0.6127 0.4072 0.0184 0.047 Uiso 1 1 calc R . . C2 C 0.5276(5) 0.2810(8) 0.07404(18) 0.0240(14) Uani 1 1 d . . . C3 C 0.5248(5) 0.2562(7) 0.11253(17) 0.0201(14) Uani 1 1 d . . . C4 C 0.4110(5) 0.2623(7) 0.12384(17) 0.0225(14) Uani 1 1 d . . . H4 H 0.3381 0.2822 0.1067 0.027 Uiso 1 1 calc R . . C5 C 0.4055(5) 0.2391(7) 0.16022(17) 0.0233(14) Uani 1 1 d . . . H5 H 0.3283 0.2426 0.1678 0.028 Uiso 1 1 calc R . . C6 C 0.5118(5) 0.2109(7) 0.18563(16) 0.0192(13) Uani 1 1 d . . . C7 C 0.6252(5) 0.2022(7) 0.17438(17) 0.0210(13) Uani 1 1 d . . . H7 H 0.6981 0.1808 0.1914 0.025 Uiso 1 1 calc R . . C8 C 0.6296(5) 0.2252(7) 0.13813(17) 0.0210(14) Uani 1 1 d . . . H8 H 0.7067 0.2195 0.1305 0.025 Uiso 1 1 calc R . . C9 C 0.5677(5) 0.2352(7) 0.25276(17) 0.0206(14) Uani 1 1 d . . . C10 C 0.5685(5) 0.2261(8) 0.31977(17) 0.0241(14) Uani 1 1 d . . . H10A H 0.6025 0.3489 0.3209 0.029 Uiso 1 1 calc R . . H10B H 0.6341 0.1437 0.3312 0.029 Uiso 1 1 calc R . . C11 C 0.4616(5) 0.2186(8) 0.34006(16) 0.0206(13) Uani 1 1 d . . . H11A H 0.3989 0.3067 0.3293 0.025 Uiso 1 1 calc R . . H11B H 0.4240 0.0982 0.3369 0.025 Uiso 1 1 calc R . . C12 C 0.4982(5) 0.2572(8) 0.38020(17) 0.0246(15) Uani 1 1 d . . . H12A H 0.5570 0.1648 0.3914 0.029 Uiso 1 1 calc R . . H12B H 0.5401 0.3747 0.3835 0.029 Uiso 1 1 calc R . . C13 C 0.3893(5) 0.2596(8) 0.39932(17) 0.0249(14) Uani 1 1 d . . . H13A H 0.3450 0.1445 0.3947 0.030 Uiso 1 1 calc R . . H13B H 0.3327 0.3559 0.3887 0.030 Uiso 1 1 calc R . . C14 C 0.4210(6) 0.2884(8) 0.43994(18) 0.0284(15) Uani 1 1 d . . . H14A H 0.4693 0.3999 0.4448 0.034 Uiso 1 1 calc R . . H14B H 0.4730 0.1880 0.4510 0.034 Uiso 1 1 calc R . . C15 C 0.3068(6) 0.3013(10) 0.4579(2) 0.0376(17) Uani 1 1 d . . . H15A H 0.2554 0.4013 0.4473 0.056 Uiso 1 1 calc R . . H15B H 0.3325 0.3211 0.4840 0.056 Uiso 1 1 calc R . . H15C H 0.2600 0.1896 0.4539 0.056 Uiso 1 1 calc R . . S2 S -0.19216(13) 0.84466(18) 0.24338(4) 0.0221(4) Uani 1 1 d . . . O3 O -0.1430(3) 0.9400(6) 0.43269(11) 0.0265(10) Uani 1 1 d . . . O4 O 0.0608(4) 0.9124(6) 0.44847(12) 0.0331(11) Uani 1 1 d . . . N3 N 0.0025(4) 1.0317(6) 0.27768(13) 0.0209(12) Uani 1 1 d . . . H3 H 0.0685 1.0925 0.2753 0.025 Uiso 1 1 calc R . . N4 N -0.0257(4) 1.0381(6) 0.21720(14) 0.0227(12) Uani 1 1 d . . . H4A H 0.0345 1.1164 0.2212 0.027 Uiso 1 1 calc R . . C16 C -0.1509(5) 0.9267(9) 0.47041(16) 0.0307(16) Uani 1 1 d U . . H16A H -0.1130 0.8144 0.4803 0.046 Uiso 1 1 calc R . . H16B H -0.2372 0.9285 0.4731 0.046 Uiso 1 1 calc R . . H16C H -0.1078 1.0280 0.4836 0.046 Uiso 1 1 calc R . . C17 C -0.0297(5) 0.9355(8) 0.42527(17) 0.0237(14) Uani 1 1 d . . . C18 C -0.0255(5) 0.9574(7) 0.38626(17) 0.0213(14) Uani 1 1 d . . . C19 C 0.0869(5) 0.9524(7) 0.37528(17) 0.0230(14) Uani 1 1 d . . . H19 H 0.1597 0.9342 0.3925 0.028 Uiso 1 1 calc R . . C20 C 0.0933(5) 0.9740(7) 0.33918(17) 0.0223(14) Uani 1 1 d . . . H20 H 0.1708 0.9684 0.3318 0.027 Uiso 1 1 calc R . . C21 C -0.0123(5) 1.0039(7) 0.31332(16) 0.0193(13) Uani 1 1 d . . . C22 C -0.1260(5) 1.0123(7) 0.32452(17) 0.0241(14) Uani 1 1 d . . . H22 H -0.1990 1.0321 0.3074 0.029 Uiso 1 1 calc R . . C23 C -0.1307(5) 0.9914(7) 0.36095(16) 0.0210(13) Uani 1 1 d . . . H23 H -0.2074 1.0006 0.3687 0.025 Uiso 1 1 calc R . . C24 C -0.0685(5) 0.9800(7) 0.24603(16) 0.0196(13) Uani 1 1 d . . . C25 C -0.0681(5) 0.9855(8) 0.17935(16) 0.0239(14) Uani 1 1 d . . . H25A H -0.1352 1.0659 0.1681 0.029 Uiso 1 1 calc R . . H25B H -0.1005 0.8617 0.1784 0.029 Uiso 1 1 calc R . . C26 C 0.0373(5) 0.9961(8) 0.15862(16) 0.0236(14) Uani 1 1 d . . . H26A H 0.1012 0.9088 0.1690 0.028 Uiso 1 1 calc R . . H26B H 0.0739 1.1172 0.1617 0.028 Uiso 1 1 calc R . . C27 C -0.0023(5) 0.9580(8) 0.11849(17) 0.0252(14) Uani 1 1 d . . . H27A H -0.0626 1.0493 0.1077 0.030 Uiso 1 1 calc R . . H27B H -0.0427 0.8395 0.1153 0.030 Uiso 1 1 calc R . . C28 C 0.1068(5) 0.9599(8) 0.09874(17) 0.0266(15) Uani 1 1 d . . . H28A H 0.1488 1.0770 0.1029 0.032 Uiso 1 1 calc R . . H28B H 0.1658 0.8663 0.1093 0.032 Uiso 1 1 calc R . . C29 C 0.0729(6) 0.9286(9) 0.05847(17) 0.0319(16) Uani 1 1 d . . . H29A H 0.0187 1.0269 0.0476 0.038 Uiso 1 1 calc R . . H29B H 0.0261 0.8155 0.0542 0.038 Uiso 1 1 calc R . . C30 C 0.1825(6) 0.9184(9) 0.03976(19) 0.0364(17) Uani 1 1 d . . . H30A H 0.2349 1.0233 0.0463 0.055 Uiso 1 1 calc R . . H30B H 0.1545 0.9159 0.0135 0.055 Uiso 1 1 calc R . . H30C H 0.2292 0.8094 0.0474 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0213(8) 0.0218(8) 0.0216(10) -0.0003(7) 0.0042(7) -0.0003(6) O1 0.025(2) 0.042(3) 0.013(2) 0.002(2) 0.0014(19) -0.0014(19) O2 0.031(3) 0.063(3) 0.024(3) 0.006(2) 0.005(2) 0.010(2) N1 0.021(3) 0.032(3) 0.016(3) 0.003(2) 0.004(2) -0.002(2) N2 0.022(3) 0.026(3) 0.017(3) 0.001(2) 0.004(2) -0.005(2) C1 0.035(4) 0.040(4) 0.021(4) -0.005(3) 0.012(3) -0.004(3) C2 0.023(3) 0.024(3) 0.026(4) -0.001(3) 0.005(3) -0.003(3) C3 0.025(3) 0.017(3) 0.020(4) -0.004(3) 0.008(3) 0.002(2) C4 0.023(3) 0.021(3) 0.024(4) -0.001(3) 0.002(3) 0.003(2) C5 0.019(3) 0.029(3) 0.024(4) -0.005(3) 0.011(3) -0.005(2) C6 0.020(3) 0.021(3) 0.018(4) 0.001(3) 0.007(3) 0.001(2) C7 0.024(3) 0.021(3) 0.018(4) -0.005(3) 0.003(3) -0.002(2) C8 0.017(3) 0.023(3) 0.024(4) 0.000(3) 0.007(3) -0.002(2) C9 0.024(3) 0.016(3) 0.022(4) -0.001(3) 0.003(3) 0.006(2) C10 0.025(3) 0.024(3) 0.022(4) 0.001(3) 0.002(3) -0.001(3) C11 0.025(3) 0.026(3) 0.012(3) -0.001(3) 0.006(3) 0.002(2) C12 0.027(3) 0.026(3) 0.023(4) -0.002(3) 0.011(3) 0.000(3) C13 0.034(3) 0.023(3) 0.019(4) 0.000(3) 0.008(3) -0.002(3) C14 0.034(4) 0.028(3) 0.025(4) -0.003(3) 0.012(3) 0.004(3) C15 0.035(4) 0.050(4) 0.029(4) 0.005(3) 0.011(3) -0.006(3) S2 0.0210(8) 0.0249(8) 0.0215(9) 0.0003(7) 0.0067(7) -0.0019(6) O3 0.022(2) 0.043(3) 0.015(2) -0.002(2) 0.0066(19) -0.0049(19) O4 0.031(2) 0.053(3) 0.015(3) -0.001(2) 0.003(2) 0.001(2) N3 0.021(3) 0.028(3) 0.015(3) 0.002(2) 0.008(2) -0.010(2) N4 0.030(3) 0.022(3) 0.017(3) 0.000(2) 0.005(2) -0.006(2) C16 0.027(3) 0.059(4) 0.009(3) 0.004(3) 0.010(3) -0.005(3) C17 0.029(3) 0.024(3) 0.017(4) -0.002(3) 0.002(3) 0.007(3) C18 0.019(3) 0.022(3) 0.022(4) 0.000(3) 0.004(3) -0.004(2) C19 0.025(3) 0.025(3) 0.018(4) -0.001(3) 0.002(3) 0.001(2) C20 0.015(3) 0.021(3) 0.031(4) -0.001(3) 0.005(3) 0.003(2) C21 0.026(3) 0.017(3) 0.015(3) -0.003(3) 0.005(3) -0.005(2) C22 0.021(3) 0.028(3) 0.022(4) -0.002(3) 0.001(3) 0.004(3) C23 0.022(3) 0.022(3) 0.019(4) -0.004(3) 0.005(3) 0.001(2) C24 0.022(3) 0.021(3) 0.014(3) -0.001(3) 0.002(3) 0.005(2) C25 0.032(3) 0.030(3) 0.010(3) 0.000(3) 0.006(3) 0.001(3) C26 0.028(3) 0.020(3) 0.024(4) -0.005(3) 0.006(3) -0.006(3) C27 0.025(3) 0.025(3) 0.025(4) 0.001(3) 0.003(3) -0.003(3) C28 0.030(3) 0.024(3) 0.028(4) 0.003(3) 0.011(3) -0.002(3) C29 0.040(4) 0.043(4) 0.014(4) 0.002(3) 0.008(3) -0.004(3) C30 0.048(4) 0.042(4) 0.024(4) 0.003(3) 0.020(3) 0.010(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C9 1.700(6) . ? O1 C2 1.333(7) . ? O1 C1 1.473(7) . ? O2 C2 1.219(7) . ? N1 C9 1.365(7) . ? N1 C6 1.397(7) . ? N1 H1 0.8800 . ? N2 C9 1.350(7) . ? N2 C10 1.448(8) . ? N2 H2 0.8800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.464(9) . ? C3 C8 1.389(8) . ? C3 C4 1.402(8) . ? C4 C5 1.390(8) . ? C4 H4 0.9500 . ? C5 C6 1.393(8) . ? C5 H5 0.9500 . ? C6 C7 1.398(8) . ? C7 C8 1.383(8) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C10 C11 1.521(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.518(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.512(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.519(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.542(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? S2 C24 1.692(6) . ? O3 C17 1.335(7) . ? O3 C16 1.439(7) . ? O4 C17 1.218(7) . ? N3 C24 1.359(7) . ? N3 C21 1.394(7) . ? N3 H3 0.8800 . ? N4 C24 1.331(7) . ? N4 C25 1.469(7) . ? N4 H4A 0.8800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.484(8) . ? C18 C19 1.382(8) . ? C18 C23 1.390(8) . ? C19 C20 1.381(8) . ? C19 H19 0.9500 . ? C20 C21 1.399(8) . ? C20 H20 0.9500 . ? C21 C22 1.401(8) . ? C22 C23 1.388(8) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C25 C26 1.519(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.519(8) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.529(8) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.511(8) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.511(8) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C1 115.6(5) . . ? C9 N1 C6 129.1(5) . . ? C9 N1 H1 115.5 . . ? C6 N1 H1 115.5 . . ? C9 N2 C10 128.2(5) . . ? C9 N2 H2 115.9 . . ? C10 N2 H2 115.9 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 122.2(6) . . ? O2 C2 C3 124.6(5) . . ? O1 C2 C3 113.2(5) . . ? C8 C3 C4 118.8(6) . . ? C8 C3 C2 122.8(5) . . ? C4 C3 C2 118.4(5) . . ? C5 C4 C3 119.7(6) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.7(5) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 N1 116.7(5) . . ? C5 C6 C7 119.8(6) . . ? N1 C6 C7 123.4(5) . . ? C8 C7 C6 119.0(5) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C7 C8 C3 122.0(5) . . ? C7 C8 H8 119.0 . . ? C3 C8 H8 119.0 . . ? N2 C9 N1 112.9(5) . . ? N2 C9 S1 121.9(5) . . ? N1 C9 S1 125.2(5) . . ? N2 C10 C11 109.7(5) . . ? N2 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? N2 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C10 113.5(5) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 112.4(5) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 114.7(5) . . ? C12 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? C13 C14 C15 112.9(5) . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 O3 C16 115.5(5) . . ? C24 N3 C21 130.5(5) . . ? C24 N3 H3 114.8 . . ? C21 N3 H3 114.8 . . ? C24 N4 C25 127.0(5) . . ? C24 N4 H4A 116.5 . . ? C25 N4 H4A 116.5 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 O3 122.6(6) . . ? O4 C17 C18 123.7(5) . . ? O3 C17 C18 113.7(5) . . ? C19 C18 C23 119.4(6) . . ? C19 C18 C17 118.9(5) . . ? C23 C18 C17 121.6(5) . . ? C20 C19 C18 119.9(6) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 121.1(5) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? N3 C21 C20 117.6(5) . . ? N3 C21 C22 123.4(5) . . ? C20 C21 C22 119.0(6) . . ? C23 C22 C21 119.1(6) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C18 121.3(5) . . ? C22 C23 H23 119.3 . . ? C18 C23 H23 119.3 . . ? N4 C24 N3 112.6(5) . . ? N4 C24 S2 123.4(5) . . ? N3 C24 S2 123.8(4) . . ? N4 C25 C26 109.9(5) . . ? N4 C25 H25A 109.7 . . ? C26 C25 H25A 109.7 . . ? N4 C25 H25B 109.7 . . ? C26 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? C25 C26 C27 112.8(5) . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C26 C27 C28 111.6(5) . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? C29 C28 C27 114.1(5) . . ? C29 C28 H28A 108.7 . . ? C27 C28 H28A 108.7 . . ? C29 C28 H28B 108.7 . . ? C27 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C28 C29 C30 113.4(5) . . ? C28 C29 H29A 108.9 . . ? C30 C29 H29A 108.9 . . ? C28 C29 H29B 108.9 . . ? C30 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O1 C2 O2 -2.1(8) . . . . ? C1 O1 C2 C3 177.0(5) . . . . ? O2 C2 C3 C8 176.2(6) . . . . ? O1 C2 C3 C8 -2.8(8) . . . . ? O2 C2 C3 C4 -3.1(9) . . . . ? O1 C2 C3 C4 177.9(5) . . . . ? C8 C3 C4 C5 0.6(8) . . . . ? C2 C3 C4 C5 180.0(5) . . . . ? C3 C4 C5 C6 0.4(8) . . . . ? C4 C5 C6 N1 -176.7(5) . . . . ? C4 C5 C6 C7 -1.3(8) . . . . ? C9 N1 C6 C5 -142.6(6) . . . . ? C9 N1 C6 C7 42.2(9) . . . . ? C5 C6 C7 C8 1.2(8) . . . . ? N1 C6 C7 C8 176.2(5) . . . . ? C6 C7 C8 C3 -0.1(8) . . . . ? C4 C3 C8 C7 -0.8(8) . . . . ? C2 C3 C8 C7 179.9(5) . . . . ? C10 N2 C9 N1 -170.9(5) . . . . ? C10 N2 C9 S1 7.0(8) . . . . ? C6 N1 C9 N2 -178.3(5) . . . . ? C6 N1 C9 S1 4.0(8) . . . . ? C9 N2 C10 C11 147.3(5) . . . . ? N2 C10 C11 C12 175.9(5) . . . . ? C10 C11 C12 C13 176.6(5) . . . . ? C11 C12 C13 C14 177.1(5) . . . . ? C12 C13 C14 C15 176.5(5) . . . . ? C16 O3 C17 O4 3.7(8) . . . . ? C16 O3 C17 C18 -177.5(5) . . . . ? O4 C17 C18 C19 -0.3(9) . . . . ? O3 C17 C18 C19 -179.1(5) . . . . ? O4 C17 C18 C23 -177.1(6) . . . . ? O3 C17 C18 C23 4.2(8) . . . . ? C23 C18 C19 C20 -2.6(8) . . . . ? C17 C18 C19 C20 -179.4(5) . . . . ? C18 C19 C20 C21 1.1(9) . . . . ? C24 N3 C21 C20 143.6(6) . . . . ? C24 N3 C21 C22 -39.2(9) . . . . ? C19 C20 C21 N3 177.4(5) . . . . ? C19 C20 C21 C22 0.1(8) . . . . ? N3 C21 C22 C23 -176.9(5) . . . . ? C20 C21 C22 C23 0.2(8) . . . . ? C21 C22 C23 C18 -1.9(9) . . . . ? C19 C18 C23 C22 3.1(9) . . . . ? C17 C18 C23 C22 179.8(5) . . . . ? C25 N4 C24 N3 170.1(5) . . . . ? C25 N4 C24 S2 -5.9(8) . . . . ? C21 N3 C24 N4 177.7(5) . . . . ? C21 N3 C24 S2 -6.3(8) . . . . ? C24 N4 C25 C26 -149.9(5) . . . . ? N4 C25 C26 C27 -175.3(5) . . . . ? C25 C26 C27 C28 -177.0(5) . . . . ? C26 C27 C28 C29 -178.2(5) . . . . ? C27 C28 C29 C30 -176.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.48 3.321(5) 159.9 2_645 N2 H2 S1 0.88 2.60 3.440(5) 159.9 2_645 N3 H3 S2 0.88 2.50 3.334(5) 157.7 2 N4 H4A S2 0.88 2.63 3.462(5) 159.1 2 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.821 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.110 #===END data_p-F _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Samuel J. Bradberry ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H19 F N2 S' _chemical_formula_sum 'C13 H19 F N2 S' _chemical_formula_weight 254.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 17.405(12) _cell_length_b 8.732(6) _cell_length_c 17.612(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2677(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6838 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 31.4 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8819 _exptl_absorpt_correction_T_max 0.9977 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Left)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19097 _diffrn_reflns_av_R_equivalents 0.1075 _diffrn_reflns_av_sigmaI/netI 0.1049 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4720 _reflns_number_gt 4121 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.4468P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.24(12) _refine_ls_number_reflns 4720 _refine_ls_number_parameters 307 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0974(3) 0.3992(6) 1.0273(3) 0.0278(13) Uani 1 1 d . . . C2 C 1.0374(3) 0.4877(6) 1.0539(3) 0.0232(12) Uani 1 1 d . . . H2A H 1.0349 0.5179 1.1057 0.028 Uiso 1 1 calc R . . C3 C 0.9809(3) 0.5311(5) 1.0027(3) 0.0212(11) Uani 1 1 d . . . H3A H 0.9381 0.5892 1.0197 0.025 Uiso 1 1 calc R . . C4 C 0.9866(3) 0.4897(5) 0.9256(3) 0.0178(10) Uani 1 1 d . . . C5 C 1.0504(3) 0.4076(5) 0.9000(3) 0.0224(12) Uani 1 1 d . . . H5 H 1.0559 0.3844 0.8476 0.027 Uiso 1 1 calc R . . C6 C 1.1060(3) 0.3598(5) 0.9521(3) 0.0237(12) Uani 1 1 d . . . H6 H 1.1490 0.3012 0.9359 0.028 Uiso 1 1 calc R . . C7 C 0.8944(3) 0.4828(5) 0.8147(3) 0.0162(10) Uani 1 1 d . . . C8 C 0.7791(3) 0.5122(5) 0.7310(3) 0.0190(11) Uani 1 1 d . . . H8A H 0.8068 0.4464 0.6943 0.023 Uiso 1 1 calc R . . H8B H 0.7600 0.6032 0.7033 0.023 Uiso 1 1 calc R . . C9 C 0.7111(3) 0.4241(5) 0.7635(3) 0.0215(11) Uani 1 1 d . . . H9A H 0.7305 0.3362 0.7934 0.026 Uiso 1 1 calc R . . H9B H 0.6822 0.4918 0.7983 0.026 Uiso 1 1 calc R . . C10 C 0.6576(3) 0.3660(6) 0.7025(3) 0.0285(13) Uani 1 1 d . . . H10A H 0.6862 0.2947 0.6691 0.034 Uiso 1 1 calc R . . H10B H 0.6405 0.4536 0.6711 0.034 Uiso 1 1 calc R . . C11 C 0.5860(3) 0.2826(6) 0.7346(3) 0.0318(13) Uani 1 1 d . . . H11A H 0.6025 0.2117 0.7753 0.038 Uiso 1 1 calc R . . H11B H 0.5510 0.3591 0.7574 0.038 Uiso 1 1 calc R . . C12 C 0.5435(3) 0.1941(6) 0.6752(3) 0.0312(13) Uani 1 1 d . . . H12A H 0.5781 0.1159 0.6532 0.037 Uiso 1 1 calc R . . H12B H 0.5279 0.2645 0.6339 0.037 Uiso 1 1 calc R . . C13 C 0.4708(3) 0.1137(7) 0.7077(4) 0.0428(16) Uani 1 1 d . . . H13A H 0.4446 0.0579 0.6670 0.064 Uiso 1 1 calc R . . H13B H 0.4360 0.1908 0.7290 0.064 Uiso 1 1 calc R . . H13C H 0.4861 0.0417 0.7477 0.064 Uiso 1 1 calc R . . C14 C 0.6466(3) 0.8395(5) 0.6748(3) 0.0224(11) Uani 1 1 d . . . C15 C 0.7127(3) 0.8961(6) 0.6439(3) 0.0261(12) Uani 1 1 d . . . H15 H 0.7218 0.8920 0.5908 0.031 Uiso 1 1 calc R . . C16 C 0.7658(3) 0.9597(6) 0.6930(3) 0.0243(12) Uani 1 1 d . . . H16 H 0.8119 1.0016 0.6729 0.029 Uiso 1 1 calc R . . C17 C 0.7538(3) 0.9641(5) 0.7710(3) 0.0177(10) Uani 1 1 d . . . C18 C 0.6852(3) 0.9069(5) 0.8001(3) 0.0182(11) Uani 1 1 d . . . H18 H 0.6753 0.9118 0.8530 0.022 Uiso 1 1 calc R . . C19 C 0.6311(3) 0.8422(5) 0.7511(3) 0.0238(12) Uani 1 1 d . . . H19 H 0.5845 0.8009 0.7703 0.029 Uiso 1 1 calc R . . C20 C 0.8429(3) 0.9826(5) 0.8836(2) 0.0145(10) Uani 1 1 d . . . C21 C 0.9555(3) 1.0237(5) 0.9680(3) 0.0190(11) Uani 1 1 d . . . H21A H 0.9282 0.9607 1.0062 0.023 Uiso 1 1 calc R . . H21B H 0.9741 1.1176 0.9936 0.023 Uiso 1 1 calc R . . C22 C 1.0236(3) 0.9345(5) 0.9374(3) 0.0187(10) Uani 1 1 d . . . H22A H 1.0468 0.9934 0.8952 0.022 Uiso 1 1 calc R . . H22B H 1.0048 0.8364 0.9163 0.022 Uiso 1 1 calc R . . C23 C 1.0866(3) 0.8997(5) 0.9964(3) 0.0226(11) Uani 1 1 d . . . H23A H 1.1103 0.9969 1.0134 0.027 Uiso 1 1 calc R . . H23B H 1.0631 0.8497 1.0412 0.027 Uiso 1 1 calc R . . C24 C 1.1481(3) 0.7964(5) 0.9637(3) 0.0227(11) Uani 1 1 d . . . H24A H 1.1712 0.8477 0.9191 0.027 Uiso 1 1 calc R . . H24B H 1.1236 0.7007 0.9457 0.027 Uiso 1 1 calc R . . C25 C 1.2127(3) 0.7547(6) 1.0202(3) 0.0292(13) Uani 1 1 d . . . H25A H 1.2386 0.8499 1.0369 0.035 Uiso 1 1 calc R . . H25B H 1.1897 0.7059 1.0655 0.035 Uiso 1 1 calc R . . C26 C 1.2722(3) 0.6471(6) 0.9864(3) 0.0299(13) Uani 1 1 d . . . H26A H 1.3115 0.6242 1.0245 0.045 Uiso 1 1 calc R . . H26B H 1.2963 0.6959 0.9423 0.045 Uiso 1 1 calc R . . H26C H 1.2471 0.5519 0.9705 0.045 Uiso 1 1 calc R . . F1 F 1.15257(18) 0.3519(3) 1.07763(16) 0.0389(8) Uani 1 1 d . . . F2 F 0.59216(16) 0.7751(3) 0.62796(15) 0.0320(7) Uani 1 1 d . . . N1 N 0.9268(2) 0.5452(5) 0.8779(2) 0.0205(10) Uani 1 1 d . . . H2 H 0.9066 0.6302 0.8924 0.025 Uiso 1 1 d R . . N2 N 0.8324(2) 0.5615(4) 0.7906(2) 0.0202(9) Uani 1 1 d . . . H3 H 0.8226 0.6461 0.8136 0.024 Uiso 1 1 d R . . N3 N 0.8102(2) 1.0348(5) 0.8175(2) 0.0191(9) Uani 1 1 d . . . H3B H 0.8265 1.1247 0.8018 0.023 Uiso 1 1 calc R . . N4 N 0.9020(2) 1.0661(4) 0.9070(2) 0.0196(9) Uani 1 1 d . . . H4 H 0.9099 1.1542 0.8841 0.023 Uiso 1 1 calc R . . S1 S 0.92774(7) 0.32669(13) 0.76799(7) 0.0194(3) Uani 1 1 d . . . S2 S 0.80980(7) 0.82662(13) 0.93026(7) 0.0188(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.029(3) 0.025(3) 0.029(3) 0.007(2) -0.013(2) -0.005(2) C2 0.027(3) 0.028(3) 0.015(2) -0.003(2) -0.003(2) -0.001(2) C3 0.019(3) 0.025(3) 0.019(3) -0.006(2) 0.003(2) -0.006(2) C4 0.014(3) 0.015(2) 0.024(2) -0.001(2) -0.002(2) -0.0043(19) C5 0.014(3) 0.030(3) 0.023(3) -0.003(2) 0.001(2) -0.006(2) C6 0.018(3) 0.020(2) 0.033(3) -0.003(2) -0.010(2) -0.001(2) C7 0.016(3) 0.015(2) 0.017(2) 0.002(2) 0.007(2) -0.004(2) C8 0.019(3) 0.017(3) 0.021(3) 0.001(2) -0.001(2) 0.001(2) C9 0.016(3) 0.020(3) 0.029(3) 0.000(2) -0.001(2) 0.001(2) C10 0.024(3) 0.030(3) 0.032(3) -0.002(2) 0.001(2) 0.006(2) C11 0.032(3) 0.030(3) 0.033(3) 0.002(3) -0.002(3) -0.001(3) C12 0.027(3) 0.029(3) 0.038(3) -0.006(3) -0.009(3) 0.004(2) C13 0.019(3) 0.048(4) 0.062(4) -0.010(3) -0.005(3) -0.009(3) C14 0.017(3) 0.021(3) 0.029(3) 0.000(2) -0.015(2) 0.001(2) C15 0.025(3) 0.029(3) 0.024(3) 0.008(2) 0.003(2) 0.002(2) C16 0.014(3) 0.031(3) 0.028(3) 0.010(2) 0.005(2) 0.004(2) C17 0.016(2) 0.020(2) 0.018(2) 0.001(2) 0.000(2) 0.002(2) C18 0.018(3) 0.018(3) 0.019(2) 0.002(2) -0.001(2) 0.003(2) C19 0.025(3) 0.018(2) 0.028(3) 0.005(2) -0.004(2) -0.002(2) C20 0.014(3) 0.013(2) 0.017(2) 0.0008(19) 0.002(2) -0.002(2) C21 0.015(3) 0.026(3) 0.016(2) -0.002(2) -0.009(2) -0.006(2) C22 0.019(3) 0.016(2) 0.021(2) -0.002(2) 0.000(2) -0.003(2) C23 0.021(3) 0.024(3) 0.024(2) -0.001(2) -0.009(2) -0.001(2) C24 0.020(3) 0.025(3) 0.022(2) 0.004(2) -0.002(2) 0.004(2) C25 0.024(3) 0.025(3) 0.039(3) 0.000(3) -0.010(2) 0.000(2) C26 0.025(3) 0.029(3) 0.035(3) 0.002(3) 0.001(2) 0.004(2) F1 0.041(2) 0.0363(18) 0.0394(19) 0.0022(15) -0.0208(15) 0.0071(15) F2 0.0305(17) 0.0374(18) 0.0281(16) 0.0039(14) -0.0152(13) -0.0113(14) N1 0.019(2) 0.018(2) 0.025(2) -0.0038(19) -0.0024(18) 0.0009(17) N2 0.018(2) 0.018(2) 0.024(2) -0.0080(18) -0.0041(18) 0.0003(18) N3 0.020(2) 0.016(2) 0.022(2) 0.0030(18) -0.0037(18) -0.0084(17) N4 0.017(2) 0.014(2) 0.028(2) 0.0048(18) -0.0048(18) 0.0014(18) S1 0.0177(7) 0.0185(6) 0.0220(6) -0.0018(5) -0.0009(5) 0.0012(5) S2 0.0176(7) 0.0189(6) 0.0198(6) 0.0003(5) 0.0008(5) 0.0001(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 F1 1.371(5) . ? C1 C6 1.376(7) . ? C1 C2 1.381(7) . ? C2 C3 1.387(6) . ? C2 H2A 0.9500 . ? C3 C4 1.407(7) . ? C3 H3A 0.9500 . ? C4 C5 1.396(6) . ? C4 N1 1.423(6) . ? C5 C6 1.398(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.348(6) . ? C7 N1 1.361(6) . ? C7 S1 1.695(5) . ? C8 N2 1.466(6) . ? C8 C9 1.523(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.510(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.550(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.496(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.555(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.365(7) . ? C14 C19 1.371(7) . ? C14 F2 1.377(5) . ? C15 C16 1.383(7) . ? C15 H15 0.9500 . ? C16 C17 1.389(6) . ? C16 H16 0.9500 . ? C17 C18 1.392(6) . ? C17 N3 1.420(5) . ? C18 C19 1.396(6) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 N4 1.327(6) . ? C20 N3 1.373(6) . ? C20 S2 1.692(4) . ? C21 N4 1.469(5) . ? C21 C22 1.517(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.539(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.513(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.546(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.520(6) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 H2 0.8595 . ? N2 H3 0.8596 . ? N3 H3B 0.8800 . ? N4 H4 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 C1 C6 118.1(5) . . ? F1 C1 C2 118.6(4) . . ? C6 C1 C2 123.3(5) . . ? C1 C2 C3 117.9(4) . . ? C1 C2 H2A 121.1 . . ? C3 C2 H2A 121.1 . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C5 C4 C3 119.9(5) . . ? C5 C4 N1 124.5(5) . . ? C3 C4 N1 115.5(4) . . ? C4 C5 C6 119.5(5) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 118.8(5) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? N2 C7 N1 112.6(4) . . ? N2 C7 S1 122.1(4) . . ? N1 C7 S1 125.3(4) . . ? N2 C8 C9 111.8(4) . . ? N2 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N2 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 112.4(4) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C9 C10 C11 113.2(4) . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C10 112.7(5) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 112.3(5) . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 123.4(5) . . ? C15 C14 F2 119.2(5) . . ? C19 C14 F2 117.4(5) . . ? C14 C15 C16 117.3(5) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? C15 C16 C17 121.9(5) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C16 C17 C18 118.9(4) . . ? C16 C17 N3 118.6(4) . . ? C18 C17 N3 122.4(4) . . ? C17 C18 C19 119.8(5) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 118.7(5) . . ? C14 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? N4 C20 N3 113.8(4) . . ? N4 C20 S2 123.7(3) . . ? N3 C20 S2 122.5(3) . . ? N4 C21 C22 111.4(4) . . ? N4 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? N4 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C21 C22 C23 114.7(4) . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C22 111.4(4) . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C25 114.2(4) . . ? C23 C24 H24A 108.7 . . ? C25 C24 H24A 108.7 . . ? C23 C24 H24B 108.7 . . ? C25 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C26 C25 C24 112.9(4) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C7 N1 C4 130.5(4) . . ? C7 N1 H2 114.8 . . ? C4 N1 H2 114.7 . . ? C7 N2 C8 125.6(4) . . ? C7 N2 H3 116.7 . . ? C8 N2 H3 117.6 . . ? C20 N3 C17 129.1(4) . . ? C20 N3 H3B 115.4 . . ? C17 N3 H3B 115.4 . . ? C20 N4 C21 125.5(4) . . ? C20 N4 H4 117.3 . . ? C21 N4 H4 117.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1 C1 C2 C3 -178.3(4) . . . . ? C6 C1 C2 C3 3.8(8) . . . . ? C1 C2 C3 C4 -2.0(7) . . . . ? C2 C3 C4 C5 -1.6(7) . . . . ? C2 C3 C4 N1 -177.9(4) . . . . ? C3 C4 C5 C6 3.6(7) . . . . ? N1 C4 C5 C6 179.5(4) . . . . ? F1 C1 C6 C5 -179.8(4) . . . . ? C2 C1 C6 C5 -1.9(8) . . . . ? C4 C5 C6 C1 -1.9(7) . . . . ? N2 C8 C9 C10 -177.3(4) . . . . ? C8 C9 C10 C11 -177.3(4) . . . . ? C9 C10 C11 C12 -166.4(4) . . . . ? C10 C11 C12 C13 -178.8(4) . . . . ? C19 C14 C15 C16 -0.4(7) . . . . ? F2 C14 C15 C16 -180.0(4) . . . . ? C14 C15 C16 C17 1.1(7) . . . . ? C15 C16 C17 C18 -2.0(7) . . . . ? C15 C16 C17 N3 -178.4(4) . . . . ? C16 C17 C18 C19 2.0(7) . . . . ? N3 C17 C18 C19 178.3(4) . . . . ? C15 C14 C19 C18 0.4(7) . . . . ? F2 C14 C19 C18 -180.0(4) . . . . ? C17 C18 C19 C14 -1.3(7) . . . . ? N4 C21 C22 C23 174.1(4) . . . . ? C21 C22 C23 C24 173.9(4) . . . . ? C22 C23 C24 C25 -179.2(4) . . . . ? C23 C24 C25 C26 178.3(4) . . . . ? N2 C7 N1 C4 172.2(4) . . . . ? S1 C7 N1 C4 -9.4(7) . . . . ? C5 C4 N1 C7 35.8(7) . . . . ? C3 C4 N1 C7 -148.1(5) . . . . ? N1 C7 N2 C8 -171.0(4) . . . . ? S1 C7 N2 C8 10.6(6) . . . . ? C9 C8 N2 C7 92.3(5) . . . . ? N4 C20 N3 C17 170.6(4) . . . . ? S2 C20 N3 C17 -9.8(7) . . . . ? C16 C17 N3 C20 -132.9(5) . . . . ? C18 C17 N3 C20 50.7(7) . . . . ? N3 C20 N4 C21 -169.3(4) . . . . ? S2 C20 N4 C21 11.0(7) . . . . ? C22 C21 N4 C20 90.1(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H2 S2 0.86 2.49 3.321(4) 161.5 . N1 H2 S2 0.86 2.49 3.321(4) 161.5 . N3 H3B S1 0.88 2.56 3.383(4) 155.4 1_565 N4 H4 S1 0.88 2.56 3.373(4) 154.3 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.416 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.065 #===END data_p-I _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Jennifer R. Hiscock ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H19 I N2 S' _chemical_formula_sum 'C13 H19 I N2 S' _chemical_formula_weight 362.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.4798(8) _cell_length_b 8.4051(6) _cell_length_c 15.6294(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.550(7) _cell_angle_gamma 90.00 _cell_volume 1472.03(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11974 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.300 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8026 _exptl_absorpt_correction_T_max 0.9774 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13677 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3362 _reflns_number_gt 2859 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0233P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3362 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0562 _refine_ls_wR_factor_gt 0.0541 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C10 C 1.1498(2) 0.1464(3) 0.38682(16) 0.0211(5) Uani 1 1 d . . . H10A H 1.1946 0.2480 0.3940 0.025 Uiso 1 1 calc R . . H10B H 1.1725 0.0870 0.3382 0.025 Uiso 1 1 calc R . . C11 C 1.1862(2) 0.0498(3) 0.47074(17) 0.0255(6) Uani 1 1 d . . . H11A H 1.1628 0.1088 0.5192 0.031 Uiso 1 1 calc R . . H11B H 1.1420 -0.0521 0.4634 0.031 Uiso 1 1 calc R . . C12 C 1.3189(3) 0.0148(3) 0.49595(19) 0.0336(7) Uani 1 1 d . . . H12A H 1.3633 0.1165 0.5066 0.040 Uiso 1 1 calc R . . H12B H 1.3435 -0.0396 0.4465 0.040 Uiso 1 1 calc R . . C13 C 1.3519(3) -0.0886(4) 0.5774(2) 0.0472(9) Uani 1 1 d . . . H13A H 1.4382 -0.1076 0.5911 0.071 Uiso 1 1 calc R . . H13B H 1.3098 -0.1905 0.5667 0.071 Uiso 1 1 calc R . . H13C H 1.3291 -0.0345 0.6268 0.071 Uiso 1 1 calc R . . S1 S 0.78913(5) 0.08362(7) 0.14125(4) 0.01672(12) Uani 1 1 d . . . C1 C 0.3043(2) 0.1358(3) 0.12685(15) 0.0165(5) Uani 1 1 d . . . C2 C 0.3406(2) 0.2202(3) 0.20452(15) 0.0199(5) Uani 1 1 d . . . H2A H 0.2854 0.2447 0.2400 0.024 Uiso 1 1 calc R . . C3 C 0.4575(2) 0.2675(3) 0.22915(15) 0.0192(5) Uani 1 1 d . . . H3 H 0.4825 0.3255 0.2821 0.023 Uiso 1 1 calc R . . C4 C 0.5402(2) 0.2330(3) 0.17907(15) 0.0161(5) Uani 1 1 d . . . C5 C 0.5027(2) 0.1517(3) 0.10036(15) 0.0173(5) Uani 1 1 d . . . H5 H 0.5576 0.1297 0.0643 0.021 Uiso 1 1 calc R . . C6 C 0.3848(2) 0.1027(3) 0.07477(16) 0.0183(5) Uani 1 1 d . . . H6 H 0.3592 0.0463 0.0213 0.022 Uiso 1 1 calc R . . C7 C 0.7658(2) 0.2349(3) 0.20692(14) 0.0159(5) Uani 1 1 d . . . C8 C 0.9805(2) 0.2721(3) 0.27635(15) 0.0189(5) Uani 1 1 d . . . H8A H 1.0286 0.3704 0.2789 0.023 Uiso 1 1 calc R . . H8B H 0.9962 0.2053 0.2279 0.023 Uiso 1 1 calc R . . C9 C 1.0173(2) 0.1823(3) 0.36246(16) 0.0212(5) Uani 1 1 d . . . H9A H 0.9953 0.2462 0.4098 0.025 Uiso 1 1 calc R . . H9B H 0.9724 0.0809 0.3581 0.025 Uiso 1 1 calc R . . N1 N 0.65624(16) 0.2928(2) 0.21098(12) 0.0171(4) Uani 1 1 d . . . H1 H 0.6583 0.3844 0.2386 0.021 Uiso 1 1 calc R . . N2 N 0.85459(16) 0.3129(2) 0.25939(12) 0.0184(4) Uani 1 1 d . . . H2 H 0.8350 0.3975 0.2864 0.022 Uiso 1 1 calc R . . I1 I 0.126313(14) 0.063211(19) 0.088060(10) 0.02108(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C10 0.0203(13) 0.0164(13) 0.0247(13) -0.0003(9) 0.0011(10) -0.0012(9) C11 0.0285(15) 0.0212(14) 0.0238(14) -0.0041(10) -0.0008(11) 0.0041(10) C12 0.0326(17) 0.0267(15) 0.0343(17) -0.0033(11) -0.0083(13) 0.0066(12) C13 0.058(2) 0.042(2) 0.0318(18) -0.0099(13) -0.0110(16) 0.0220(15) S1 0.0164(3) 0.0169(3) 0.0167(3) -0.0014(2) 0.0033(2) 0.0011(2) C1 0.0109(12) 0.0197(12) 0.0175(12) 0.0015(8) -0.0002(9) -0.0013(9) C2 0.0195(13) 0.0235(13) 0.0185(12) -0.0014(9) 0.0078(10) 0.0011(10) C3 0.0210(13) 0.0212(13) 0.0149(12) -0.0050(9) 0.0028(10) -0.0007(9) C4 0.0160(12) 0.0125(11) 0.0193(12) 0.0020(8) 0.0029(9) 0.0004(8) C5 0.0148(12) 0.0197(13) 0.0176(12) -0.0001(9) 0.0040(9) 0.0025(9) C6 0.0175(13) 0.0179(12) 0.0177(12) -0.0006(9) 0.0001(10) 0.0009(9) C7 0.0163(12) 0.0164(12) 0.0147(12) 0.0035(8) 0.0025(9) 0.0006(9) C8 0.0156(12) 0.0209(13) 0.0197(13) -0.0031(9) 0.0030(10) -0.0015(9) C9 0.0196(13) 0.0217(13) 0.0221(13) -0.0032(10) 0.0041(10) -0.0015(10) N1 0.0144(10) 0.0155(10) 0.0205(11) -0.0045(7) 0.0018(8) -0.0005(8) N2 0.0146(10) 0.0193(10) 0.0207(11) -0.0049(8) 0.0028(8) 0.0025(8) I1 0.01548(9) 0.02584(10) 0.02169(10) -0.00083(6) 0.00352(6) -0.00358(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C10 C9 1.517(3) . ? C10 C11 1.522(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.516(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.520(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? S1 C7 1.692(2) . ? C1 C6 1.386(3) . ? C1 C2 1.389(3) . ? C1 I1 2.092(2) . ? C2 C3 1.372(3) . ? C2 H2A 0.9500 . ? C3 C4 1.386(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(3) . ? C4 N1 1.410(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.334(3) . ? C7 N1 1.362(3) . ? C8 N2 1.453(3) . ? C8 C9 1.521(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C10 C11 113.3(2) . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C10 113.6(2) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 112.5(3) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 C1 C2 120.3(2) . . ? C6 C1 I1 120.34(17) . . ? C2 C1 I1 119.39(17) . . ? C3 C2 C1 118.8(2) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 122.0(2) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 119.0(2) . . ? C3 C4 N1 115.9(2) . . ? C5 C4 N1 125.1(2) . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C1 C6 C5 120.3(2) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N2 C7 N1 112.7(2) . . ? N2 C7 S1 122.80(18) . . ? N1 C7 S1 124.48(17) . . ? N2 C8 C9 110.68(19) . . ? N2 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 113.1(2) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C7 N1 C4 131.8(2) . . ? C7 N1 H1 114.1 . . ? C4 N1 H1 114.1 . . ? C7 N2 C8 126.4(2) . . ? C7 N2 H2 116.8 . . ? C8 N2 H2 116.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C10 C11 C12 -179.5(2) . . . . ? C10 C11 C12 C13 -177.1(2) . . . . ? C6 C1 C2 C3 -1.1(4) . . . . ? I1 C1 C2 C3 -179.87(18) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 1.7(4) . . . . ? C2 C3 C4 N1 178.2(2) . . . . ? C3 C4 C5 C6 -1.8(3) . . . . ? N1 C4 C5 C6 -178.0(2) . . . . ? C2 C1 C6 C5 0.9(4) . . . . ? I1 C1 C6 C5 179.68(17) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C11 C10 C9 C8 -177.3(2) . . . . ? N2 C8 C9 C10 -176.0(2) . . . . ? N2 C7 N1 C4 -168.2(2) . . . . ? S1 C7 N1 C4 13.2(4) . . . . ? C3 C4 N1 C7 147.0(2) . . . . ? C5 C4 N1 C7 -36.7(4) . . . . ? N1 C7 N2 C8 174.0(2) . . . . ? S1 C7 N2 C8 -7.4(3) . . . . ? C9 C8 N2 C7 -99.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.49 3.328(2) 159.1 2_655 N2 H2 S1 0.88 2.54 3.380(2) 159.5 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.488 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.093 #===END data_p-NO2 _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Marco Wenzel ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H19 N3 O2 S' _chemical_formula_sum 'C13 H19 N3 O2 S' _chemical_formula_weight 281.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2833(5) _cell_length_b 14.9019(15) _cell_length_c 18.0119(18) _cell_angle_alpha 91.957(7) _cell_angle_beta 95.987(7) _cell_angle_gamma 92.116(7) _cell_volume 1408.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8919 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9551 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11029 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4960 _reflns_number_gt 4467 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.6313P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4960 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.7700(3) 0.04702(12) 0.43195(9) 0.0290(4) Uani 1 1 d . . . H1A H 1.7193 0.0306 0.4807 0.043 Uiso 1 1 calc R . . H1B H 1.9478 0.0696 0.4379 0.043 Uiso 1 1 calc R . . H1C H 1.7523 -0.0060 0.3978 0.043 Uiso 1 1 calc R . . C2 C 1.6007(3) 0.11944(12) 0.40015(9) 0.0254(4) Uani 1 1 d . . . H2A H 1.6162 0.1722 0.4355 0.030 Uiso 1 1 calc R . . H2B H 1.4212 0.0966 0.3953 0.030 Uiso 1 1 calc R . . C3 C 1.6668(3) 0.14911(10) 0.32435(8) 0.0195(3) Uani 1 1 d . . . H3A H 1.8427 0.1755 0.3300 0.023 Uiso 1 1 calc R . . H3B H 1.6627 0.0956 0.2901 0.023 Uiso 1 1 calc R . . C4 C 1.4886(3) 0.21724(10) 0.28931(8) 0.0193(3) Uani 1 1 d . . . H4A H 1.5009 0.2722 0.3221 0.023 Uiso 1 1 calc R . . H4B H 1.3115 0.1923 0.2867 0.023 Uiso 1 1 calc R . . C5 C 1.5438(3) 0.24296(10) 0.21119(8) 0.0185(3) Uani 1 1 d . . . H5A H 1.7140 0.2737 0.2139 0.022 Uiso 1 1 calc R . . H5B H 1.5453 0.1880 0.1788 0.022 Uiso 1 1 calc R . . C6 C 1.3439(3) 0.30441(11) 0.17769(8) 0.0190(3) Uani 1 1 d . . . H6A H 1.1731 0.2749 0.1779 0.023 Uiso 1 1 calc R . . H6B H 1.3490 0.3607 0.2088 0.023 Uiso 1 1 calc R . . C7 C 1.2252(3) 0.37580(10) 0.05952(8) 0.0149(3) Uani 1 1 d . . . C8 C 1.4484(3) 0.36260(10) -0.05787(8) 0.0147(3) Uani 1 1 d . . . C9 C 1.4845(3) 0.41251(10) -0.12069(8) 0.0169(3) Uani 1 1 d . . . H9 H 1.3912 0.4651 -0.1294 0.020 Uiso 1 1 calc R . . C10 C 1.6529(3) 0.38659(10) -0.17005(8) 0.0172(3) Uani 1 1 d . . . H10 H 1.6752 0.4203 -0.2129 0.021 Uiso 1 1 calc R . . C11 C 1.7892(3) 0.31014(10) -0.15570(8) 0.0155(3) Uani 1 1 d . . . C12 C 1.7541(3) 0.25833(10) -0.09487(8) 0.0163(3) Uani 1 1 d . . . H12 H 1.8490 0.2061 -0.0863 0.020 Uiso 1 1 calc R . . C13 C 1.5796(3) 0.28349(10) -0.04678(8) 0.0168(3) Uani 1 1 d . . . H13 H 1.5487 0.2470 -0.0062 0.020 Uiso 1 1 calc R . . N1 N 1.3849(2) 0.32603(8) 0.10117(7) 0.0166(3) Uani 1 1 d . . . H1 H 1.5191 0.3056 0.0820 0.020 Uiso 1 1 calc R . . N2 N 1.2737(2) 0.39551(8) -0.01123(7) 0.0165(3) Uani 1 1 d . . . H2 H 1.1766 0.4368 -0.0314 0.020 Uiso 1 1 calc R . . N3 N 1.9764(2) 0.28432(8) -0.20525(7) 0.0172(3) Uani 1 1 d . . . O1 O 2.1030(2) 0.21816(7) -0.18961(6) 0.0231(2) Uani 1 1 d . . . O2 O 2.0033(2) 0.32876(7) -0.26043(6) 0.0235(3) Uani 1 1 d . . . S1 S 0.96466(7) 0.41808(2) 0.09283(2) 0.01693(10) Uani 1 1 d . . . C14 C 1.2031(4) 0.52855(13) 0.68299(10) 0.0354(4) Uani 1 1 d . . . H14A H 1.1703 0.4857 0.7213 0.053 Uiso 1 1 calc R . . H14B H 1.2715 0.5856 0.7071 0.053 Uiso 1 1 calc R . . H14C H 1.3268 0.5042 0.6515 0.053 Uiso 1 1 calc R . . C15 C 0.9572(3) 0.54428(12) 0.63522(10) 0.0309(4) Uani 1 1 d . . . H15A H 0.8871 0.4859 0.6126 0.037 Uiso 1 1 calc R . . H15B H 0.8328 0.5676 0.6678 0.037 Uiso 1 1 calc R . . C16 C 0.9840(3) 0.60907(12) 0.57359(9) 0.0275(4) Uani 1 1 d . . . H16A H 1.1103 0.5860 0.5415 0.033 Uiso 1 1 calc R . . H16B H 1.0529 0.6675 0.5964 0.033 Uiso 1 1 calc R . . C17 C 0.7404(3) 0.62496(11) 0.52467(9) 0.0243(4) Uani 1 1 d . . . H17A H 0.6144 0.6489 0.5564 0.029 Uiso 1 1 calc R . . H17B H 0.6702 0.5667 0.5020 0.029 Uiso 1 1 calc R . . C18 C 0.7745(3) 0.68968(11) 0.46276(9) 0.0253(4) Uani 1 1 d . . . H18A H 0.8460 0.7479 0.4852 0.030 Uiso 1 1 calc R . . H18B H 0.8984 0.6655 0.4305 0.030 Uiso 1 1 calc R . . C19 C 0.5299(3) 0.70521(13) 0.41552(10) 0.0298(4) Uani 1 1 d . . . H19A H 0.4523 0.6467 0.3955 0.036 Uiso 1 1 calc R . . H19B H 0.4095 0.7333 0.4470 0.036 Uiso 1 1 calc R . . C20 C 0.4210(3) 0.82950(10) 0.33129(8) 0.0173(3) Uani 1 1 d . . . C21 C 0.3881(3) 0.93262(10) 0.22220(8) 0.0162(3) Uani 1 1 d . . . C22 C 0.4956(3) 0.94216(10) 0.15468(8) 0.0194(3) Uani 1 1 d . . . H22 H 0.6395 0.9087 0.1455 0.023 Uiso 1 1 calc R . . C23 C 0.3968(3) 0.99885(11) 0.10189(9) 0.0208(3) Uani 1 1 d . . . H23 H 0.4710 1.0046 0.0564 0.025 Uiso 1 1 calc R . . C24 C 0.1873(3) 1.04772(10) 0.11559(8) 0.0183(3) Uani 1 1 d . . . C25 C 0.0836(3) 1.04213(10) 0.18283(9) 0.0199(3) Uani 1 1 d . . . H25 H -0.0565 1.0775 0.1922 0.024 Uiso 1 1 calc R . . C26 C 0.1831(3) 0.98539(10) 0.23631(9) 0.0200(3) Uani 1 1 d . . . H26 H 0.1128 0.9821 0.2826 0.024 Uiso 1 1 calc R . . N4 N 0.5695(2) 0.76279(10) 0.35375(8) 0.0248(3) Uani 1 1 d . . . H4 H 0.7020 0.7529 0.3292 0.030 Uiso 1 1 calc R . . N5 N 0.5011(2) 0.87021(9) 0.26960(7) 0.0186(3) Uani 1 1 d . . . H5 H 0.6509 0.8537 0.2582 0.022 Uiso 1 1 calc R . . N6 N 0.0734(2) 1.10438(9) 0.05815(7) 0.0219(3) Uani 1 1 d . . . O3 O 0.1646(2) 1.10578(8) -0.00222(6) 0.0311(3) Uani 1 1 d . . . O4 O -0.1107(2) 1.14819(8) 0.07160(7) 0.0319(3) Uani 1 1 d . . . S2 S 0.16881(7) 0.85807(3) 0.37390(2) 0.02368(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0334(9) 0.0320(9) 0.0228(8) 0.0072(7) 0.0040(7) 0.0106(8) C2 0.0290(9) 0.0298(9) 0.0192(8) 0.0044(7) 0.0064(7) 0.0104(7) C3 0.0185(7) 0.0222(8) 0.0184(8) 0.0020(6) 0.0034(6) 0.0031(6) C4 0.0187(7) 0.0221(8) 0.0177(7) 0.0019(6) 0.0037(6) 0.0040(6) C5 0.0159(7) 0.0224(8) 0.0177(7) 0.0018(6) 0.0031(6) 0.0025(6) C6 0.0166(7) 0.0263(8) 0.0148(7) 0.0030(6) 0.0031(6) 0.0039(6) C7 0.0130(7) 0.0148(7) 0.0164(7) -0.0010(6) 0.0010(6) -0.0018(6) C8 0.0119(7) 0.0174(7) 0.0141(7) -0.0022(6) 0.0003(6) -0.0009(5) C9 0.0176(7) 0.0161(7) 0.0175(7) 0.0021(6) 0.0016(6) 0.0057(6) C10 0.0199(7) 0.0177(7) 0.0145(7) 0.0020(6) 0.0030(6) 0.0018(6) C11 0.0137(7) 0.0175(7) 0.0152(7) -0.0036(6) 0.0017(6) 0.0009(6) C12 0.0164(7) 0.0153(7) 0.0168(7) -0.0006(6) -0.0012(6) 0.0041(6) C13 0.0186(7) 0.0167(7) 0.0154(7) 0.0018(6) 0.0023(6) 0.0023(6) N1 0.0129(6) 0.0237(7) 0.0139(6) 0.0020(5) 0.0040(5) 0.0044(5) N2 0.0162(6) 0.0187(6) 0.0155(6) 0.0033(5) 0.0021(5) 0.0068(5) N3 0.0158(6) 0.0180(7) 0.0174(6) -0.0031(5) 0.0016(5) 0.0008(5) O1 0.0224(6) 0.0246(6) 0.0235(6) -0.0005(5) 0.0049(5) 0.0110(5) O2 0.0275(6) 0.0244(6) 0.0208(6) 0.0031(5) 0.0114(5) 0.0025(5) S1 0.01337(18) 0.0196(2) 0.01880(19) 0.00160(14) 0.00497(14) 0.00409(14) C14 0.0395(11) 0.0309(10) 0.0336(10) 0.0117(8) -0.0069(8) -0.0058(8) C15 0.0293(9) 0.0321(10) 0.0323(9) 0.0115(8) 0.0049(8) 0.0015(7) C16 0.0274(9) 0.0270(9) 0.0274(9) 0.0073(7) -0.0004(7) -0.0049(7) C17 0.0226(8) 0.0260(9) 0.0260(8) 0.0071(7) 0.0072(7) 0.0039(7) C18 0.0245(8) 0.0263(9) 0.0255(8) 0.0071(7) 0.0037(7) -0.0004(7) C19 0.0234(8) 0.0367(10) 0.0318(9) 0.0166(8) 0.0085(7) 0.0058(7) C20 0.0167(7) 0.0194(8) 0.0155(7) -0.0011(6) 0.0005(6) 0.0002(6) C21 0.0155(7) 0.0167(7) 0.0157(7) -0.0009(6) 0.0002(6) -0.0008(6) C22 0.0183(7) 0.0207(8) 0.0200(8) -0.0006(6) 0.0050(6) 0.0045(6) C23 0.0236(8) 0.0224(8) 0.0174(7) 0.0019(6) 0.0065(6) 0.0032(6) C24 0.0192(7) 0.0163(7) 0.0192(7) 0.0021(6) 0.0008(6) 0.0006(6) C25 0.0178(7) 0.0189(8) 0.0237(8) -0.0004(6) 0.0042(6) 0.0038(6) C26 0.0208(8) 0.0208(8) 0.0193(8) 0.0000(6) 0.0060(6) 0.0029(6) N4 0.0188(7) 0.0326(8) 0.0260(7) 0.0117(6) 0.0105(6) 0.0091(6) N5 0.0159(6) 0.0244(7) 0.0171(6) 0.0035(5) 0.0063(5) 0.0071(5) N6 0.0234(7) 0.0199(7) 0.0227(7) 0.0037(5) 0.0023(6) 0.0019(5) O3 0.0358(7) 0.0367(7) 0.0232(6) 0.0111(5) 0.0082(5) 0.0097(5) O4 0.0301(7) 0.0335(7) 0.0349(7) 0.0110(5) 0.0076(5) 0.0169(5) S2 0.0225(2) 0.0275(2) 0.0234(2) 0.00459(16) 0.01033(16) 0.00598(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.516(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.520(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.525(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.515(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.4620(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N1 1.3329(19) . ? C7 N2 1.3652(19) . ? C7 S1 1.6919(14) . ? C8 C13 1.399(2) . ? C8 C9 1.400(2) . ? C8 N2 1.4020(18) . ? C9 C10 1.378(2) . ? C9 H9 0.9500 . ? C10 C11 1.387(2) . ? C10 H10 0.9500 . ? C11 C12 1.386(2) . ? C11 N3 1.4533(18) . ? C12 C13 1.382(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? N3 O2 1.2304(17) . ? N3 O1 1.2357(17) . ? C14 C15 1.512(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.510(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.513(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.519(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.501(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N4 1.456(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 N4 1.337(2) . ? C20 N5 1.3809(19) . ? C20 S2 1.6668(15) . ? C21 N5 1.393(2) . ? C21 C26 1.401(2) . ? C21 C22 1.404(2) . ? C22 C23 1.369(2) . ? C22 H22 0.9500 . ? C23 C24 1.386(2) . ? C23 H23 0.9500 . ? C24 C25 1.384(2) . ? C24 N6 1.453(2) . ? C25 C26 1.379(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? N4 H4 0.8800 . ? N5 H5 0.8800 . ? N6 O4 1.2315(17) . ? N6 O3 1.2349(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 112.98(13) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 113.76(13) . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? C2 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 114.03(12) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 110.58(12) . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C5 111.58(12) . . ? N1 C6 H6A 109.3 . . ? C5 C6 H6A 109.3 . . ? N1 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? N1 C7 N2 119.92(13) . . ? N1 C7 S1 121.60(11) . . ? N2 C7 S1 118.46(11) . . ? C13 C8 C9 119.15(13) . . ? C13 C8 N2 124.60(13) . . ? C9 C8 N2 116.22(13) . . ? C10 C9 C8 121.09(14) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 118.43(14) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 C10 121.84(13) . . ? C12 C11 N3 119.06(13) . . ? C10 C11 N3 119.10(13) . . ? C13 C12 C11 119.31(14) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C8 120.06(14) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C7 N1 C6 122.02(12) . . ? C7 N1 H1 119.0 . . ? C6 N1 H1 119.0 . . ? C7 N2 C8 132.37(13) . . ? C7 N2 H2 113.8 . . ? C8 N2 H2 113.8 . . ? O2 N3 O1 122.81(12) . . ? O2 N3 C11 119.23(12) . . ? O1 N3 C11 117.96(12) . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C14 114.38(14) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 115.16(14) . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C16 C17 C18 113.84(13) . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C19 C18 C17 112.88(13) . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? N4 C19 C18 111.93(13) . . ? N4 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? N4 C19 H19B 109.2 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? N4 C20 N5 112.13(13) . . ? N4 C20 S2 122.77(12) . . ? N5 C20 S2 125.10(12) . . ? N5 C21 C26 126.11(13) . . ? N5 C21 C22 115.19(13) . . ? C26 C21 C22 118.70(14) . . ? C23 C22 C21 121.16(14) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 119.26(14) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C25 C24 C23 120.73(14) . . ? C25 C24 N6 119.80(14) . . ? C23 C24 N6 119.47(13) . . ? C26 C25 C24 120.19(14) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 119.87(14) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? C20 N4 C19 125.26(13) . . ? C20 N4 H4 117.4 . . ? C19 N4 H4 117.4 . . ? C20 N5 C21 131.75(13) . . ? C20 N5 H5 114.1 . . ? C21 N5 H5 114.1 . . ? O4 N6 O3 122.97(13) . . ? O4 N6 C24 118.61(13) . . ? O3 N6 C24 118.42(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.83 3.3296(13) 117.9 1_655 N2 H2 S1 0.88 2.56 3.4079(13) 161.4 2_765 N4 H4 O2 0.88 2.42 3.2625(17) 159.2 2_865 N4 H4 S2 0.88 2.90 3.4009(14) 117.9 1_655 N5 H5 O1 0.88 2.17 2.9811(16) 153.0 2_865 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.313 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.044 #===END data_p-OCOMe _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Jennifer R. Hiscock ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 N2 O2 S' _chemical_formula_sum 'C15 H22 N2 O2 S' _chemical_formula_weight 294.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.553(4) _cell_length_b 9.157(8) _cell_length_c 30.91(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.215(8) _cell_angle_gamma 90.00 _cell_volume 1569(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3306 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 30.7 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24561 _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3586 _reflns_number_gt 3121 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0722P)^2^+0.9038P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3586 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0724 _refine_ls_wR_factor_ref 0.1805 _refine_ls_wR_factor_gt 0.1729 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.5198(5) 0.6290(3) 0.35550(9) 0.0395(7) Uani 1 1 d . . . H1A H -0.6175 0.7126 0.3454 0.059 Uiso 1 1 calc R . . H1B H -0.4586 0.6460 0.3854 0.059 Uiso 1 1 calc R . . H1C H -0.6192 0.5405 0.3542 0.059 Uiso 1 1 calc R . . O2 O -0.1590(4) 0.5161(2) 0.33099(6) 0.0425(5) Uani 1 1 d . . . C2 C -0.3120(5) 0.6103(3) 0.32714(8) 0.0310(6) Uani 1 1 d . . . C3 C -0.1371(4) 0.7098(3) 0.26480(8) 0.0296(5) Uani 1 1 d . . . C4 C -0.1759(5) 0.6270(3) 0.22772(8) 0.0331(6) Uani 1 1 d . . . H4 H -0.3113 0.5637 0.2247 0.040 Uiso 1 1 calc R . . C5 C -0.0154(5) 0.6368(3) 0.19462(8) 0.0330(6) Uani 1 1 d . . . H5 H -0.0401 0.5793 0.1692 0.040 Uiso 1 1 calc R . . C6 C 0.1809(5) 0.7311(3) 0.19913(8) 0.0296(5) Uani 1 1 d . . . C7 C 0.2176(5) 0.8128(3) 0.23727(8) 0.0306(6) Uani 1 1 d . . . H7 H 0.3529 0.8761 0.2406 0.037 Uiso 1 1 calc R . . C8 C 0.0590(5) 0.8027(3) 0.27036(8) 0.0307(6) Uani 1 1 d . . . H8 H 0.0845 0.8581 0.2962 0.037 Uiso 1 1 calc R . . C9 C 0.4261(5) 0.6717(3) 0.13442(8) 0.0320(6) Uani 1 1 d . . . C10 C 0.7211(5) 0.6656(3) 0.07692(8) 0.0359(6) Uani 1 1 d . . . H10A H 0.6033 0.6304 0.0540 0.043 Uiso 1 1 calc R . . H10B H 0.8095 0.5800 0.0893 0.043 Uiso 1 1 calc R . . C11 C 0.8981(5) 0.7702(3) 0.05725(9) 0.0361(6) Uani 1 1 d . . . H11A H 1.0169 0.8041 0.0802 0.043 Uiso 1 1 calc R . . H11B H 0.8095 0.8567 0.0455 0.043 Uiso 1 1 calc R . . C12 C 1.0312(5) 0.6974(3) 0.02092(8) 0.0355(6) Uani 1 1 d . . . H12A H 0.9114 0.6611 -0.0015 0.043 Uiso 1 1 calc R . . H12B H 1.1220 0.6121 0.0329 0.043 Uiso 1 1 calc R . . C13 C 1.2067(5) 0.8007(3) -0.00040(9) 0.0354(6) Uani 1 1 d . . . H13A H 1.1160 0.8863 -0.0122 0.043 Uiso 1 1 calc R . . H13B H 1.3270 0.8365 0.0220 0.043 Uiso 1 1 calc R . . C14 C 1.3393(5) 0.7290(3) -0.03692(9) 0.0384(7) Uani 1 1 d . . . H14A H 1.2191 0.6928 -0.0593 0.046 Uiso 1 1 calc R . . H14B H 1.4309 0.6438 -0.0251 0.046 Uiso 1 1 calc R . . C15 C 1.5133(6) 0.8331(3) -0.05823(9) 0.0438(7) Uani 1 1 d . . . H15A H 1.5943 0.7811 -0.0810 0.066 Uiso 1 1 calc R . . H15B H 1.6339 0.8686 -0.0364 0.066 Uiso 1 1 calc R . . H15C H 1.4230 0.9160 -0.0709 0.066 Uiso 1 1 calc R . . N1 N 0.3453(4) 0.7589(2) 0.16672(7) 0.0338(5) Uani 1 1 d . . . H1 H 0.4063 0.8476 0.1674 0.041 Uiso 1 1 calc R . . N2 N 0.5931(4) 0.7386(3) 0.11099(7) 0.0361(5) Uani 1 1 d . . . H2 H 0.6265 0.8309 0.1165 0.043 Uiso 1 1 calc R . . O1 O -0.3153(3) 0.7128(2) 0.29603(6) 0.0348(5) Uani 1 1 d . . . S1 S 0.33601(14) 0.49998(7) 0.12358(2) 0.0383(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0358(15) 0.0457(16) 0.0382(13) 0.0088(12) 0.0142(12) 0.0104(13) O2 0.0452(12) 0.0418(11) 0.0423(10) 0.0124(8) 0.0175(9) 0.0191(9) C2 0.0310(14) 0.0310(13) 0.0314(12) 0.0028(10) 0.0063(10) 0.0036(11) C3 0.0269(13) 0.0286(13) 0.0341(12) 0.0052(10) 0.0086(10) 0.0066(10) C4 0.0305(14) 0.0270(13) 0.0425(14) 0.0036(11) 0.0075(11) -0.0050(11) C5 0.0376(15) 0.0282(13) 0.0336(12) -0.0008(10) 0.0057(11) -0.0058(11) C6 0.0297(13) 0.0283(13) 0.0313(12) 0.0029(10) 0.0073(10) -0.0010(10) C7 0.0273(13) 0.0280(13) 0.0369(13) -0.0026(10) 0.0039(10) 0.0006(10) C8 0.0312(13) 0.0292(13) 0.0319(12) -0.0018(10) 0.0025(10) 0.0073(11) C9 0.0351(14) 0.0301(13) 0.0318(12) 0.0036(10) 0.0103(11) -0.0019(11) C10 0.0434(16) 0.0308(13) 0.0349(13) -0.0007(10) 0.0140(11) -0.0036(12) C11 0.0397(15) 0.0313(14) 0.0385(13) -0.0018(11) 0.0137(12) -0.0063(12) C12 0.0419(16) 0.0303(13) 0.0358(13) -0.0022(11) 0.0145(11) -0.0046(12) C13 0.0391(15) 0.0293(13) 0.0391(13) -0.0029(11) 0.0127(11) -0.0033(11) C14 0.0469(17) 0.0318(14) 0.0381(14) -0.0052(11) 0.0168(12) -0.0058(12) C15 0.0532(18) 0.0364(15) 0.0440(15) -0.0028(12) 0.0225(14) -0.0061(13) N1 0.0366(12) 0.0280(11) 0.0381(11) -0.0026(9) 0.0138(10) -0.0087(9) N2 0.0412(13) 0.0293(11) 0.0395(12) -0.0015(9) 0.0169(10) -0.0056(10) O1 0.0340(10) 0.0340(10) 0.0376(9) 0.0086(8) 0.0138(8) 0.0103(8) S1 0.0517(5) 0.0250(4) 0.0397(4) -0.0001(2) 0.0167(3) -0.0066(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.497(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O2 C2 1.212(3) . ? C2 O1 1.343(3) . ? C3 C4 1.381(4) . ? C3 C8 1.385(4) . ? C3 O1 1.421(3) . ? C4 C5 1.397(4) . ? C4 H4 0.9500 . ? C5 C6 1.392(4) . ? C5 H5 0.9500 . ? C6 C7 1.401(4) . ? C6 N1 1.416(3) . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N2 1.355(3) . ? C9 N1 1.373(3) . ? C9 S1 1.678(3) . ? C10 N2 1.465(3) . ? C10 C11 1.523(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.532(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.533(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.530(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.532(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 123.3(2) . . ? O2 C2 C1 125.7(2) . . ? O1 C2 C1 111.1(2) . . ? C4 C3 C8 121.7(2) . . ? C4 C3 O1 119.5(2) . . ? C8 C3 O1 118.5(2) . . ? C3 C4 C5 119.8(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 119.6(2) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 119.5(2) . . ? C5 C6 N1 125.0(2) . . ? C7 C6 N1 115.5(2) . . ? C8 C7 C6 121.0(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C3 C8 C7 118.4(2) . . ? C3 C8 H8 120.8 . . ? C7 C8 H8 120.8 . . ? N2 C9 N1 112.8(2) . . ? N2 C9 S1 121.50(19) . . ? N1 C9 S1 125.74(18) . . ? N2 C10 C11 110.5(2) . . ? N2 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N2 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 C11 C12 111.6(2) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 113.0(2) . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 113.3(2) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 113.1(2) . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 N1 C6 131.3(2) . . ? C9 N1 H1 114.4 . . ? C6 N1 H1 114.4 . . ? C9 N2 C10 123.5(2) . . ? C9 N2 H2 118.3 . . ? C10 N2 H2 118.3 . . ? C2 O1 C3 119.42(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.88 2.08 2.928(3) 160.4 2 N2 H2 O2 0.88 2.35 3.120(4) 146.7 2 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.449 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.058 #===END data_p-OEt _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert Jennifer R. Hiscock ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H24 N2 O S' _chemical_formula_sum 'C15 H24 N2 O S' _chemical_formula_weight 280.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.390(10) _cell_length_b 9.689(11) _cell_length_c 19.62(2) _cell_angle_alpha 93.19(2) _cell_angle_beta 101.167(18) _cell_angle_gamma 90.09(3) _cell_volume 1562(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3738 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 31.2 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9473 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, VHF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12058 _diffrn_reflns_av_R_equivalents 0.0876 _diffrn_reflns_av_sigmaI/netI 0.1410 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5451 _reflns_number_gt 3650 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+2.2437P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5451 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1467 _refine_ls_R_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.2111 _refine_ls_wR_factor_gt 0.1868 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1923(8) 0.3324(6) -0.2096(3) 0.0388(15) Uani 1 1 d . . . H1A H -0.2157 0.3770 -0.2540 0.058 Uiso 1 1 calc R . . H1B H -0.2840 0.3452 -0.1857 0.058 Uiso 1 1 calc R . . H1C H -0.1756 0.2333 -0.2183 0.058 Uiso 1 1 calc R . . C3 C 0.0074(7) 0.3324(6) -0.0941(3) 0.0296(13) Uani 1 1 d . . . H3A H 0.0295 0.2332 -0.1025 0.035 Uiso 1 1 calc R . . H3B H -0.0868 0.3384 -0.0705 0.035 Uiso 1 1 calc R . . C4 C 0.1544(7) 0.3988(6) -0.0456(3) 0.0300(13) Uani 1 1 d . . . H4A H 0.1341 0.4984 -0.0374 0.036 Uiso 1 1 calc R . . H4B H 0.2502 0.3905 -0.0681 0.036 Uiso 1 1 calc R . . C5 C 0.1913(7) 0.3312(6) 0.0243(3) 0.0296(13) Uani 1 1 d . . . H5A H 0.2117 0.2316 0.0159 0.035 Uiso 1 1 calc R . . H5B H 0.0948 0.3388 0.0463 0.035 Uiso 1 1 calc R . . C6 C 0.3388(7) 0.3964(6) 0.0748(2) 0.0283(13) Uani 1 1 d . . . H6A H 0.4376 0.3856 0.0545 0.034 Uiso 1 1 calc R . . H6B H 0.3210 0.4964 0.0833 0.034 Uiso 1 1 calc R . . C7 C 0.4791(6) 0.3512(5) 0.1958(3) 0.0243(12) Uani 1 1 d . . . C8 C 0.5739(7) 0.2659(6) 0.3167(3) 0.0268(13) Uani 1 1 d . . . C9 C 0.6743(7) 0.3727(6) 0.3515(3) 0.0296(13) Uani 1 1 d . . . H9 H 0.6757 0.4593 0.3311 0.036 Uiso 1 1 calc R . . C10 C 0.7730(7) 0.3529(5) 0.4162(3) 0.0278(13) Uani 1 1 d . . . H10 H 0.8437 0.4252 0.4388 0.033 Uiso 1 1 calc R . . C11 C 0.7685(7) 0.2293(5) 0.4473(3) 0.0265(13) Uani 1 1 d . . . C12 C 0.6649(7) 0.1221(6) 0.4134(3) 0.0296(13) Uani 1 1 d . . . H12 H 0.6606 0.0370 0.4349 0.035 Uiso 1 1 calc R . . C13 C 0.5691(7) 0.1401(5) 0.3487(3) 0.0267(12) Uani 1 1 d . . . H13 H 0.4998 0.0671 0.3258 0.032 Uiso 1 1 calc R . . C14 C 0.9607(7) 0.3065(5) 0.5495(3) 0.0293(13) Uani 1 1 d . . . H14A H 0.8958 0.3883 0.5587 0.035 Uiso 1 1 calc R . . H14B H 1.0421 0.3345 0.5224 0.035 Uiso 1 1 calc R . . C15 C 1.0444(7) 0.2492(6) 0.6175(3) 0.0369(15) Uani 1 1 d . . . H15A H 1.1160 0.3204 0.6451 0.055 Uiso 1 1 calc R . . H15B H 1.1089 0.1688 0.6078 0.055 Uiso 1 1 calc R . . H15C H 0.9625 0.2212 0.6437 0.055 Uiso 1 1 calc R . . C16 C 0.2981(7) 0.1169(6) -0.2167(3) 0.0349(14) Uani 1 1 d . . . H16A H 0.2798 0.0627 -0.2613 0.052 Uiso 1 1 calc R . . H16B H 0.3121 0.2147 -0.2248 0.052 Uiso 1 1 calc R . . H16C H 0.2043 0.1059 -0.1944 0.052 Uiso 1 1 calc R . . C17 C 0.4488(7) 0.0667(6) -0.1701(3) 0.0300(13) Uani 1 1 d . . . H17A H 0.5412 0.0726 -0.1945 0.036 Uiso 1 1 calc R . . H17B H 0.4327 -0.0318 -0.1619 0.036 Uiso 1 1 calc R . . C18 C 0.4927(7) 0.1482(6) -0.0997(3) 0.0287(13) Uani 1 1 d . . . H18A H 0.5095 0.2465 -0.1080 0.034 Uiso 1 1 calc R . . H18B H 0.3994 0.1432 -0.0757 0.034 Uiso 1 1 calc R . . C19 C 0.6432(7) 0.0981(6) -0.0517(3) 0.0289(13) Uani 1 1 d . . . H19A H 0.7376 0.1058 -0.0748 0.035 Uiso 1 1 calc R . . H19B H 0.6280 -0.0008 -0.0440 0.035 Uiso 1 1 calc R . . C20 C 0.6806(6) 0.1789(6) 0.0187(2) 0.0266(13) Uani 1 1 d . . . H20A H 0.6964 0.2778 0.0111 0.032 Uiso 1 1 calc R . . H20B H 0.5864 0.1714 0.0418 0.032 Uiso 1 1 calc R . . C21 C 0.8308(7) 0.1278(5) 0.0662(3) 0.0276(13) Uani 1 1 d . . . H21A H 0.8172 0.0286 0.0736 0.033 Uiso 1 1 calc R . . H21B H 0.9268 0.1384 0.0444 0.033 Uiso 1 1 calc R . . C22 C 0.9751(6) 0.1879(5) 0.1886(2) 0.0242(12) Uani 1 1 d . . . C23 C 1.0707(7) 0.2494(5) 0.3135(3) 0.0258(12) Uani 1 1 d . . . C24 C 1.0662(7) 0.1277(6) 0.3480(3) 0.0297(13) Uani 1 1 d . . . H24 H 0.9971 0.0535 0.3263 0.036 Uiso 1 1 calc R . . C25 C 1.1595(7) 0.1137(5) 0.4122(3) 0.0301(13) Uani 1 1 d . . . H25 H 1.1557 0.0299 0.4348 0.036 Uiso 1 1 calc R . . C26 C 1.2611(7) 0.2225(6) 0.4451(3) 0.0276(13) Uani 1 1 d . . . C27 C 1.2669(7) 0.3460(5) 0.4119(3) 0.0272(13) Uani 1 1 d . . . H27 H 1.3351 0.4204 0.4338 0.033 Uiso 1 1 calc R . . C28 C 1.1703(7) 0.3580(5) 0.3457(3) 0.0294(13) Uani 1 1 d . . . H28 H 1.1732 0.4415 0.3227 0.035 Uiso 1 1 calc R . . C29 C 1.4533(7) 0.3057(6) 0.5455(3) 0.0354(14) Uani 1 1 d . . . H29A H 1.3887 0.3879 0.5544 0.042 Uiso 1 1 calc R . . H29B H 1.5331 0.3325 0.5173 0.042 Uiso 1 1 calc R . . C30 C 1.5398(8) 0.2505(7) 0.6136(3) 0.0478(18) Uani 1 1 d . . . H30A H 1.6112 0.3227 0.6404 0.072 Uiso 1 1 calc R . . H30B H 1.6046 0.1703 0.6040 0.072 Uiso 1 1 calc R . . H30C H 1.4593 0.2228 0.6406 0.072 Uiso 1 1 calc R . . C47 C -0.0379(7) 0.3975(6) -0.1638(3) 0.0292(13) Uani 1 1 d . . . H47A H 0.0534 0.3868 -0.1889 0.035 Uiso 1 1 calc R . . H47B H -0.0551 0.4976 -0.1557 0.035 Uiso 1 1 calc R . . N1 N 0.3595(5) 0.3264(5) 0.1404(2) 0.0281(11) Uani 1 1 d . . . H1 H 0.2874 0.2633 0.1439 0.034 Uiso 1 1 d R . . N2 N 0.4675(5) 0.2780(4) 0.2517(2) 0.0242(10) Uani 1 1 d . . . H2 H 0.3777 0.2286 0.2470 0.029 Uiso 1 1 d R . . N3 N 0.8558(6) 0.2088(4) 0.1337(2) 0.0283(11) Uani 1 1 d . . . H3 H 0.7871 0.2756 0.1379 0.034 Uiso 1 1 d R . . N4 N 0.9672(5) 0.2650(4) 0.24666(19) 0.0265(11) Uani 1 1 d . . . H4 H 0.8936 0.3301 0.2439 0.032 Uiso 1 1 d R . . O1 O 0.8578(5) 0.1995(4) 0.51200(17) 0.0313(9) Uani 1 1 d . . . O2 O 1.3499(5) 0.1973(4) 0.50991(18) 0.0329(10) Uani 1 1 d . . . S1 S 0.63145(17) 0.46497(14) 0.19180(7) 0.0272(4) Uani 1 1 d . . . S2 S 1.12539(17) 0.07127(14) 0.18254(7) 0.0277(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.049(4) 0.032(4) 0.031(3) 0.001(3) 0.000(3) -0.007(3) C3 0.029(3) 0.031(3) 0.028(3) -0.001(2) 0.004(2) 0.001(3) C4 0.027(3) 0.033(3) 0.029(3) 0.008(2) 0.002(2) 0.000(3) C5 0.033(3) 0.022(3) 0.032(3) -0.001(2) 0.001(3) -0.003(2) C6 0.029(3) 0.030(3) 0.023(3) 0.008(2) -0.003(2) -0.001(3) C7 0.025(3) 0.019(3) 0.028(3) 0.006(2) 0.001(2) 0.001(2) C8 0.030(3) 0.029(3) 0.023(3) 0.002(2) 0.008(2) 0.000(3) C9 0.033(3) 0.023(3) 0.033(3) 0.004(2) 0.006(3) -0.006(3) C10 0.032(3) 0.020(3) 0.029(3) 0.000(2) -0.001(2) -0.007(2) C11 0.029(3) 0.027(3) 0.024(3) 0.001(2) 0.007(2) 0.006(3) C12 0.043(4) 0.022(3) 0.027(3) 0.002(2) 0.011(3) -0.002(3) C13 0.028(3) 0.024(3) 0.028(3) 0.000(2) 0.007(2) -0.005(2) C14 0.028(3) 0.025(3) 0.034(3) -0.004(2) 0.006(3) -0.007(2) C15 0.040(4) 0.034(4) 0.032(3) 0.003(3) -0.004(3) -0.003(3) C16 0.038(4) 0.036(4) 0.026(3) -0.002(3) -0.002(3) -0.001(3) C17 0.031(3) 0.028(3) 0.030(3) -0.001(2) 0.002(3) 0.000(3) C18 0.027(3) 0.023(3) 0.034(3) 0.004(2) 0.003(2) -0.008(2) C19 0.027(3) 0.026(3) 0.032(3) 0.001(2) 0.003(2) -0.001(2) C20 0.024(3) 0.028(3) 0.027(3) 0.001(2) 0.002(2) -0.003(2) C21 0.031(3) 0.023(3) 0.030(3) -0.001(2) 0.008(2) -0.004(2) C22 0.022(3) 0.024(3) 0.025(3) 0.000(2) 0.002(2) -0.009(2) C23 0.029(3) 0.021(3) 0.025(3) -0.001(2) 0.002(2) 0.004(2) C24 0.031(3) 0.024(3) 0.032(3) 0.003(2) 0.000(3) -0.001(3) C25 0.041(4) 0.018(3) 0.031(3) 0.003(2) 0.005(3) -0.003(3) C26 0.032(3) 0.027(3) 0.024(3) 0.003(2) 0.007(2) 0.002(3) C27 0.029(3) 0.024(3) 0.028(3) -0.004(2) 0.006(2) -0.006(2) C28 0.041(4) 0.018(3) 0.030(3) 0.004(2) 0.007(3) 0.003(3) C29 0.036(4) 0.029(3) 0.038(3) -0.001(3) 0.003(3) -0.001(3) C30 0.046(4) 0.054(4) 0.037(3) 0.001(3) -0.009(3) -0.012(3) C47 0.035(4) 0.024(3) 0.030(3) 0.007(2) 0.007(3) -0.005(3) N1 0.026(3) 0.030(3) 0.028(2) 0.010(2) 0.004(2) -0.003(2) N2 0.022(3) 0.023(2) 0.026(2) 0.0017(19) 0.001(2) -0.006(2) N3 0.032(3) 0.024(3) 0.025(2) -0.0022(19) -0.003(2) 0.001(2) N4 0.032(3) 0.024(3) 0.020(2) 0.0028(19) -0.003(2) 0.007(2) O1 0.037(2) 0.026(2) 0.028(2) 0.0025(16) -0.0012(18) -0.0050(18) O2 0.037(3) 0.029(2) 0.029(2) 0.0019(17) -0.0027(18) -0.0036(18) S1 0.0275(8) 0.0239(8) 0.0295(7) 0.0065(6) 0.0026(6) -0.0024(6) S2 0.0274(8) 0.0220(8) 0.0324(7) -0.0012(6) 0.0031(6) 0.0002(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C47 1.538(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C47 1.519(7) . ? C3 C4 1.522(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.530(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.538(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.470(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N1 1.339(6) . ? C7 N2 1.357(6) . ? C7 S1 1.703(5) . ? C8 C9 1.393(7) . ? C8 C13 1.405(7) . ? C8 N2 1.419(6) . ? C9 C10 1.398(7) . ? C9 H9 0.9500 . ? C10 C11 1.379(7) . ? C10 H10 0.9500 . ? C11 O1 1.389(6) . ? C11 C12 1.404(7) . ? C12 C13 1.385(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.424(6) . ? C14 C15 1.518(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.508(7) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.533(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.520(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.525(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.516(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 N3 1.480(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 N4 1.340(6) . ? C22 N3 1.346(6) . ? C22 S2 1.711(6) . ? C23 C28 1.387(7) . ? C23 C24 1.396(7) . ? C23 N4 1.442(6) . ? C24 C25 1.363(7) . ? C24 H24 0.9500 . ? C25 C26 1.401(7) . ? C25 H25 0.9500 . ? C26 O2 1.378(6) . ? C26 C27 1.399(7) . ? C27 C28 1.402(7) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 O2 1.423(6) . ? C29 C30 1.518(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? N1 H1 0.8740 . ? N2 H2 0.8788 . ? N3 H3 0.8783 . ? N4 H4 0.8795 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C47 C1 H1A 109.5 . . ? C47 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C47 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C47 C3 C4 114.4(4) . . ? C47 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C47 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 111.8(4) . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C6 113.2(4) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? N1 C6 C5 108.4(4) . . ? N1 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? N1 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? N1 C7 N2 114.7(5) . . ? N1 C7 S1 120.0(4) . . ? N2 C7 S1 125.3(4) . . ? C9 C8 C13 119.1(5) . . ? C9 C8 N2 123.9(5) . . ? C13 C8 N2 116.8(5) . . ? C8 C9 C10 120.2(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 120.5(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 O1 125.4(5) . . ? C10 C11 C12 119.6(5) . . ? O1 C11 C12 114.9(5) . . ? C13 C12 C11 120.1(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 120.3(5) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? O1 C14 C15 107.1(4) . . ? O1 C14 H14A 110.3 . . ? C15 C14 H14A 110.3 . . ? O1 C14 H14B 110.3 . . ? C15 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C16 C17 C18 114.0(5) . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C19 C18 C17 114.7(5) . . ? C19 C18 H18A 108.6 . . ? C17 C18 H18A 108.6 . . ? C19 C18 H18B 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C18 C19 C20 113.3(5) . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19B 108.9 . . ? C20 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C21 C20 C19 112.8(4) . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20B 109.0 . . ? C19 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? N3 C21 C20 109.4(4) . . ? N3 C21 H21A 109.8 . . ? C20 C21 H21A 109.8 . . ? N3 C21 H21B 109.8 . . ? C20 C21 H21B 109.8 . . ? H21A C21 H21B 108.2 . . ? N4 C22 N3 115.3(5) . . ? N4 C22 S2 123.5(4) . . ? N3 C22 S2 121.2(4) . . ? C28 C23 C24 119.3(5) . . ? C28 C23 N4 120.2(5) . . ? C24 C23 N4 120.5(5) . . ? C25 C24 C23 120.9(5) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C24 C25 C26 120.3(5) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? O2 C26 C27 124.7(5) . . ? O2 C26 C25 115.4(5) . . ? C27 C26 C25 119.9(5) . . ? C26 C27 C28 119.0(5) . . ? C26 C27 H27 120.5 . . ? C28 C27 H27 120.5 . . ? C23 C28 C27 120.7(5) . . ? C23 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? O2 C29 C30 106.7(5) . . ? O2 C29 H29A 110.4 . . ? C30 C29 H29A 110.4 . . ? O2 C29 H29B 110.4 . . ? C30 C29 H29B 110.4 . . ? H29A C29 H29B 108.6 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C3 C47 C1 112.6(4) . . ? C3 C47 H47A 109.1 . . ? C1 C47 H47A 109.1 . . ? C3 C47 H47B 109.1 . . ? C1 C47 H47B 109.1 . . ? H47A C47 H47B 107.8 . . ? C7 N1 C6 125.7(4) . . ? C7 N1 H1 116.8 . . ? C6 N1 H1 117.4 . . ? C7 N2 C8 131.9(5) . . ? C7 N2 H2 114.4 . . ? C8 N2 H2 113.6 . . ? C22 N3 C21 125.1(5) . . ? C22 N3 H3 118.0 . . ? C21 N3 H3 117.0 . . ? C22 N4 C23 124.8(5) . . ? C22 N4 H4 117.8 . . ? C23 N4 H4 117.4 . . ? C11 O1 C14 117.1(4) . . ? C26 O2 C29 117.2(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C47 C3 C4 C5 178.6(5) . . . . ? C3 C4 C5 C6 -179.7(5) . . . . ? C4 C5 C6 N1 178.3(5) . . . . ? C13 C8 C9 C10 2.2(8) . . . . ? N2 C8 C9 C10 178.6(5) . . . . ? C8 C9 C10 C11 -2.0(9) . . . . ? C9 C10 C11 O1 -178.3(5) . . . . ? C9 C10 C11 C12 0.6(8) . . . . ? C10 C11 C12 C13 0.7(8) . . . . ? O1 C11 C12 C13 179.7(5) . . . . ? C11 C12 C13 C8 -0.5(8) . . . . ? C9 C8 C13 C12 -1.0(8) . . . . ? N2 C8 C13 C12 -177.6(5) . . . . ? C16 C17 C18 C19 179.4(5) . . . . ? C17 C18 C19 C20 -178.4(5) . . . . ? C18 C19 C20 C21 179.9(4) . . . . ? C19 C20 C21 N3 -178.4(4) . . . . ? C28 C23 C24 C25 -0.8(8) . . . . ? N4 C23 C24 C25 -177.8(5) . . . . ? C23 C24 C25 C26 0.5(9) . . . . ? C24 C25 C26 O2 180.0(5) . . . . ? C24 C25 C26 C27 0.0(8) . . . . ? O2 C26 C27 C28 179.8(5) . . . . ? C25 C26 C27 C28 -0.2(8) . . . . ? C24 C23 C28 C27 0.6(8) . . . . ? N4 C23 C28 C27 177.5(5) . . . . ? C26 C27 C28 C23 -0.1(8) . . . . ? C4 C3 C47 C1 -177.0(5) . . . . ? N2 C7 N1 C6 176.9(5) . . . . ? S1 C7 N1 C6 -4.2(8) . . . . ? C5 C6 N1 C7 177.1(5) . . . . ? N1 C7 N2 C8 174.0(5) . . . . ? S1 C7 N2 C8 -4.9(8) . . . . ? C9 C8 N2 C7 33.2(9) . . . . ? C13 C8 N2 C7 -150.3(5) . . . . ? N4 C22 N3 C21 -174.5(5) . . . . ? S2 C22 N3 C21 6.1(7) . . . . ? C20 C21 N3 C22 177.9(5) . . . . ? N3 C22 N4 C23 172.8(5) . . . . ? S2 C22 N4 C23 -7.7(8) . . . . ? C28 C23 N4 C22 119.4(6) . . . . ? C24 C23 N4 C22 -63.7(8) . . . . ? C10 C11 O1 C14 1.0(8) . . . . ? C12 C11 O1 C14 -178.0(5) . . . . ? C15 C14 O1 C11 -179.8(5) . . . . ? C27 C26 O2 C29 0.7(8) . . . . ? C25 C26 O2 C29 -179.3(5) . . . . ? C30 C29 O2 C26 -178.4(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S2 0.87 2.54 3.390(5) 165.7 1_455 N2 H2 S2 0.88 2.67 3.502(5) 157.9 1_455 N3 H3 S1 0.88 2.55 3.397(5) 161.2 . N4 H4 S1 0.88 2.62 3.453(5) 157.7 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.375 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.073 #===END data_p-OMe _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H22 N2 O S' _chemical_formula_sum 'C14 H22 N2 O S' _chemical_formula_weight 266.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 36.040(5) _cell_length_b 4.347(5) _cell_length_c 9.590(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 95.300(5) _cell_angle_gamma 90.000(5) _cell_volume 1496.0(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2378 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 26.6 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_type 'DLS beamline I19' _diffrn_source synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_collimation 'Confocal mirrors' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku Saturn724 (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'CrystalLogic' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen micromount' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8777 _diffrn_reflns_av_R_equivalents 0.1318 _diffrn_reflns_av_sigmaI/netI 0.1148 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 24.21 _reflns_number_total 2402 _reflns_number_gt 1218 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Data completeness only 90.8%, but this is sufficient for proof of structure and hydrogen bonding network ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1863P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2402 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1509 _refine_ls_R_factor_gt 0.0993 _refine_ls_wR_factor_ref 0.2973 _refine_ls_wR_factor_gt 0.2443 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.46481(15) 0.7234(17) 1.1180(7) 0.0593(17) Uani 1 1 d . . . H1A H 0.4871 0.7653 1.0696 0.089 Uiso 1 1 calc R . . H1B H 0.4704 0.5630 1.1886 0.089 Uiso 1 1 calc R . . H1C H 0.4571 0.9116 1.1638 0.089 Uiso 1 1 calc R . . C2 C 0.43352(13) 0.6154(15) 1.0128(7) 0.0551(17) Uani 1 1 d . . . H2A H 0.4416 0.4269 0.9661 0.066 Uiso 1 1 calc R . . H2B H 0.4286 0.7757 0.9401 0.066 Uiso 1 1 calc R . . C3 C 0.39687(13) 0.5463(15) 1.0805(6) 0.0491(15) Uani 1 1 d . . . H3A H 0.4021 0.3911 1.1553 0.059 Uiso 1 1 calc R . . H3B H 0.3886 0.7366 1.1250 0.059 Uiso 1 1 calc R . . C4 C 0.36491(12) 0.4272(15) 0.9767(6) 0.0491(16) Uani 1 1 d . . . H4A H 0.3730 0.2344 0.9335 0.059 Uiso 1 1 calc R . . H4B H 0.3599 0.5805 0.9010 0.059 Uiso 1 1 calc R . . C5 C 0.32838(13) 0.3649(14) 1.0453(6) 0.0462(15) Uani 1 1 d . . . H5A H 0.3332 0.2134 1.1219 0.055 Uiso 1 1 calc R . . H5B H 0.3197 0.5580 1.0864 0.055 Uiso 1 1 calc R . . C6 C 0.29788(12) 0.2411(14) 0.9375(6) 0.0460(15) Uani 1 1 d . . . H6A H 0.2939 0.3860 0.8579 0.055 Uiso 1 1 calc R . . H6B H 0.3056 0.0403 0.9010 0.055 Uiso 1 1 calc R . . C7 C 0.23104(12) 0.0853(12) 0.9406(6) 0.0364(13) Uani 1 1 d . . . C8 C 0.16203(11) 0.0539(13) 0.9601(5) 0.0371(13) Uani 1 1 d . . . C9 C 0.14116(12) -0.1500(12) 1.0347(6) 0.0374(13) Uani 1 1 d . . . H9 H 0.1526 -0.2560 1.1140 0.045 Uiso 1 1 calc R . . C10 C 0.10321(12) -0.1971(13) 0.9919(6) 0.0404(13) Uani 1 1 d . . . H10 H 0.0888 -0.3304 1.0442 0.048 Uiso 1 1 calc R . . C11 C 0.08667(11) -0.0504(13) 0.8739(6) 0.0371(13) Uani 1 1 d . . . C12 C 0.10794(13) 0.1526(12) 0.7990(6) 0.0414(13) Uani 1 1 d . . . H12 H 0.0968 0.2543 0.7180 0.050 Uiso 1 1 calc R . . C13 C 0.14548(12) 0.2043(13) 0.8443(6) 0.0393(13) Uani 1 1 d . . . H13 H 0.1596 0.3443 0.7946 0.047 Uiso 1 1 calc R . . C14 C 0.02692(13) -0.2947(14) 0.8944(6) 0.0467(14) Uani 1 1 d . . . H14A H 0.0016 -0.3022 0.8479 0.070 Uiso 1 1 calc R . . H14B H 0.0261 -0.2225 0.9909 0.070 Uiso 1 1 calc R . . H14C H 0.0379 -0.5008 0.8952 0.070 Uiso 1 1 calc R . . N1 N 0.26293(10) 0.2043(11) 1.0052(5) 0.0421(12) Uani 1 1 d . . . H1 H 0.2628 0.2632 1.0930 0.051 Uiso 1 1 calc R . . N2 N 0.20046(10) 0.1167(10) 1.0137(5) 0.0408(12) Uani 1 1 d . . . H2 H 0.2043 0.1806 1.1009 0.049 Uiso 1 1 calc R . . O1 O 0.04925(8) -0.0860(8) 0.8197(4) 0.0434(10) Uani 1 1 d . . . S1 S 0.22995(3) -0.1058(3) 0.78263(15) 0.0425(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.043(3) 0.083(5) 0.052(4) -0.005(4) 0.009(3) -0.011(3) C2 0.034(3) 0.078(5) 0.055(4) -0.010(3) 0.018(3) -0.006(2) C3 0.036(3) 0.072(4) 0.041(4) -0.004(3) 0.010(2) -0.009(2) C4 0.031(2) 0.084(5) 0.035(4) -0.003(3) 0.013(2) -0.002(2) C5 0.033(3) 0.072(4) 0.034(3) -0.002(3) 0.008(2) -0.009(2) C6 0.032(2) 0.068(4) 0.041(3) -0.007(3) 0.017(2) -0.007(2) C7 0.037(3) 0.048(3) 0.025(3) 0.007(2) 0.011(2) -0.0008(19) C8 0.028(2) 0.060(4) 0.024(3) -0.013(3) 0.0090(19) 0.004(2) C9 0.034(2) 0.052(3) 0.028(3) 0.001(3) 0.010(2) -0.0004(19) C10 0.037(3) 0.060(4) 0.027(3) -0.002(3) 0.013(2) -0.002(2) C11 0.027(2) 0.052(3) 0.033(3) -0.007(3) 0.007(2) 0.0022(19) C12 0.038(3) 0.052(3) 0.036(3) 0.004(3) 0.010(2) 0.005(2) C13 0.035(2) 0.052(3) 0.032(3) 0.005(3) 0.012(2) -0.002(2) C14 0.036(3) 0.057(4) 0.048(4) -0.002(3) 0.012(2) 0.000(2) N1 0.030(2) 0.075(3) 0.023(2) 0.001(2) 0.0118(16) -0.0063(18) N2 0.033(2) 0.062(3) 0.030(3) -0.008(2) 0.0113(17) -0.0043(17) O1 0.0295(17) 0.061(3) 0.041(3) 0.0032(18) 0.0085(15) -0.0024(14) S1 0.0369(8) 0.0614(10) 0.0304(9) -0.0032(6) 0.0102(5) 0.0008(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.516(8) . ? C2 C3 1.554(7) . ? C3 C4 1.541(7) . ? C4 C5 1.549(6) . ? C5 C6 1.535(7) . ? C6 N1 1.478(6) . ? C7 N1 1.357(6) . ? C7 N2 1.366(6) . ? C7 S1 1.725(6) . ? C8 C13 1.376(7) . ? C8 C9 1.401(7) . ? C8 N2 1.458(6) . ? C9 C10 1.406(6) . ? C10 C11 1.385(8) . ? C11 C12 1.408(8) . ? C11 O1 1.408(5) . ? C12 C13 1.401(6) . ? C14 O1 1.446(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 113.0(5) . . ? C4 C3 C2 114.1(5) . . ? C3 C4 C5 113.5(5) . . ? C6 C5 C4 111.0(5) . . ? N1 C6 C5 109.2(5) . . ? N1 C7 N2 114.7(5) . . ? N1 C7 S1 122.3(4) . . ? N2 C7 S1 123.0(4) . . ? C13 C8 C9 120.0(4) . . ? C13 C8 N2 121.5(5) . . ? C9 C8 N2 118.4(5) . . ? C8 C9 C10 119.8(5) . . ? C11 C10 C9 120.3(5) . . ? C10 C11 C12 119.5(4) . . ? C10 C11 O1 125.2(5) . . ? C12 C11 O1 115.4(4) . . ? C13 C12 C11 119.9(5) . . ? C8 C13 C12 120.5(5) . . ? C7 N1 C6 124.1(5) . . ? C7 N2 C8 125.8(5) . . ? C11 O1 C14 116.4(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.88 2.71 3.482(5) 147.6 4_566 N2 H2 S1 0.88 2.65 3.434(5) 149.4 4_566 _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 24.21 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 1.085 _refine_diff_density_min -0.782 _refine_diff_density_rms 0.100