# Supporting Info (ESI) 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' 'Vitor Felix' 'Jeremy G. Frey' 'Philip A. Gale' data_p-Methyl _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 S' _chemical_formula_sum 'C14 H22 N2 S' _chemical_formula_weight 250.40 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' '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 10.731(3) _cell_length_b 8.475(2) _cell_length_c 16.092(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.010(7) _cell_angle_gamma 90.00 _cell_volume 1431.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3122 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9363 _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 5504 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0677 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2520 _reflns_number_gt 2051 _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^)+(0.0851P)^2^+16.4959P] 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 2520 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1123 _refine_ls_R_factor_gt 0.0980 _refine_ls_wR_factor_ref 0.3108 _refine_ls_wR_factor_gt 0.3033 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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 0.1423(7) 0.5725(9) 0.0772(5) 0.0312(17) Uani 1 1 d . . . H1A H 0.0883 0.6028 0.1168 0.047 Uiso 1 1 calc R . . H1B H 0.1424 0.4574 0.0715 0.047 Uiso 1 1 calc R . . H1C H 0.1092 0.6204 0.0216 0.047 Uiso 1 1 calc R . . C2 C 0.2770(6) 0.6298(8) 0.1110(4) 0.0234(15) Uani 1 1 d . . . C3 C 0.3722(6) 0.6021(8) 0.0659(4) 0.0231(15) Uani 1 1 d . . . H3 H 0.3519 0.5461 0.0137 0.028 Uiso 1 1 calc R . . C4 C 0.4963(6) 0.6542(8) 0.0953(4) 0.0218(14) Uani 1 1 d . . . H4 H 0.5593 0.6367 0.0627 0.026 Uiso 1 1 calc R . . C5 C 0.5274(6) 0.7326(8) 0.1730(4) 0.0196(14) Uani 1 1 d . . . C6 C 0.4331(7) 0.7613(8) 0.2181(4) 0.0249(15) Uani 1 1 d . . . H6 H 0.4539 0.8150 0.2710 0.030 Uiso 1 1 calc R . . C7 C 0.3097(7) 0.7129(9) 0.1874(4) 0.0274(16) Uani 1 1 d . . . H7 H 0.2459 0.7364 0.2185 0.033 Uiso 1 1 calc R . . C8 C 0.7688(6) 0.7394(7) 0.2086(4) 0.0188(14) Uani 1 1 d . . . C9 C 0.9951(6) 0.7762(8) 0.2822(4) 0.0230(15) Uani 1 1 d . . . H9A H 1.0483 0.8726 0.2871 0.028 Uiso 1 1 calc R . . H9B H 1.0163 0.7097 0.2366 0.028 Uiso 1 1 calc R . . C10 C 1.0241(6) 0.6856(8) 0.3665(4) 0.0226(15) Uani 1 1 d . . . H10A H 0.9959 0.7495 0.4107 0.027 Uiso 1 1 calc R . . H10B H 0.9745 0.5862 0.3599 0.027 Uiso 1 1 calc R . . C11 C 1.1652(6) 0.6463(8) 0.3965(4) 0.0248(15) Uani 1 1 d . . . H11A H 1.2145 0.7456 0.4070 0.030 Uiso 1 1 calc R . . H11B H 1.1951 0.5882 0.3509 0.030 Uiso 1 1 calc R . . C12 C 1.1911(7) 0.5467(9) 0.4774(4) 0.0265(16) Uani 1 1 d . . . H12A H 1.1610 0.6050 0.5228 0.032 Uiso 1 1 calc R . . H12B H 1.1415 0.4477 0.4667 0.032 Uiso 1 1 calc R . . C13 C 1.3306(7) 0.5063(9) 0.5081(5) 0.0343(18) Uani 1 1 d . . . H13A H 1.3794 0.6051 0.5228 0.041 Uiso 1 1 calc R . . H13B H 1.3623 0.4551 0.4612 0.041 Uiso 1 1 calc R . . C14 C 1.3558(9) 0.3972(11) 0.5851(5) 0.043(2) Uani 1 1 d . . . H14A H 1.4473 0.3755 0.6018 0.064 Uiso 1 1 calc R . . H14B H 1.3094 0.2979 0.5708 0.064 Uiso 1 1 calc R . . H14C H 1.3267 0.4480 0.6324 0.064 Uiso 1 1 calc R . . N1 N 0.6507(5) 0.7937(7) 0.2089(4) 0.0215(12) Uani 1 1 d . . . H1 H 0.6495 0.8834 0.2363 0.026 Uiso 1 1 calc R . . N2 N 0.8610(5) 0.8197(7) 0.2606(4) 0.0224(13) Uani 1 1 d . . . H2 H 0.8385 0.9064 0.2837 0.027 Uiso 1 1 calc R . . S1 S 0.80203(15) 0.58515(19) 0.14796(10) 0.0204(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 0.027(4) 0.035(4) 0.031(4) 0.002(3) 0.003(3) 0.000(3) C2 0.026(3) 0.021(3) 0.022(3) 0.005(3) 0.004(3) 0.000(3) C3 0.028(4) 0.019(3) 0.019(3) -0.002(3) 0.000(3) 0.002(3) C4 0.023(3) 0.023(3) 0.019(3) 0.003(3) 0.005(3) 0.003(3) C5 0.021(3) 0.018(3) 0.019(3) 0.005(3) 0.001(3) 0.000(3) C6 0.028(4) 0.023(4) 0.024(3) -0.003(3) 0.004(3) -0.001(3) C7 0.026(4) 0.037(4) 0.021(3) 0.005(3) 0.010(3) 0.004(3) C8 0.021(3) 0.016(3) 0.020(3) 0.003(3) 0.006(3) -0.001(3) C9 0.020(3) 0.027(4) 0.022(3) -0.001(3) 0.005(3) 0.000(3) C10 0.025(3) 0.019(3) 0.024(3) -0.003(3) 0.006(3) -0.002(3) C11 0.027(4) 0.021(3) 0.026(4) 0.002(3) 0.004(3) -0.002(3) C12 0.034(4) 0.025(4) 0.020(3) -0.003(3) 0.004(3) 0.001(3) C13 0.028(4) 0.028(4) 0.042(4) 0.002(3) -0.003(3) 0.002(3) C14 0.056(5) 0.043(5) 0.025(4) 0.002(4) -0.002(4) 0.012(4) N1 0.022(3) 0.019(3) 0.022(3) -0.004(2) 0.002(2) 0.000(2) N2 0.023(3) 0.018(3) 0.026(3) -0.004(2) 0.003(2) 0.001(2) S1 0.0218(8) 0.0199(9) 0.0192(8) -0.0012(6) 0.0037(6) 0.0018(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 C2 1.514(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.390(10) . ? C2 C7 1.397(10) . ? C3 C4 1.389(9) . ? C3 H3 0.9500 . ? C4 C5 1.394(9) . ? C4 H4 0.9500 . ? C5 C6 1.383(10) . ? C5 N1 1.426(8) . ? C6 C7 1.376(10) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N2 1.341(8) . ? C8 N1 1.349(8) . ? C8 S1 1.713(7) . ? C9 N2 1.455(8) . ? C9 C10 1.533(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.527(9) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.528(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.515(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.525(11) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 . . ? C3 C2 C7 117.8(6) . . ? C3 C2 C1 120.6(6) . . ? C7 C2 C1 121.6(6) . . ? C4 C3 C2 121.7(6) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.4(6) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.3(6) . . ? C6 C5 N1 116.2(6) . . ? C4 C5 N1 124.4(6) . . ? C7 C6 C5 120.9(6) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C2 120.9(7) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? N2 C8 N1 113.4(6) . . ? N2 C8 S1 121.9(5) . . ? N1 C8 S1 124.7(5) . . ? N2 C9 C10 110.3(5) . . ? N2 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? N2 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 113.2(5) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 112.4(6) . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 113.3(6) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C14 113.5(7) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 N1 C5 131.9(6) . . ? C8 N1 H1 114.1 . . ? C5 N1 H1 114.1 . . ? C8 N2 C9 125.9(6) . . ? C8 N2 H2 117.1 . . ? C9 N2 H2 117.1 . . ? 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 2.50 3.344(6) 160.2 2_655 N2 H2 S1 0.88 2.54 3.371(6) 156.9 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.904 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.125 #===END data_p-Propyl _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 'C16 H26 N2 S' _chemical_formula_sum 'C16 H26 N2 S' _chemical_formula_weight 278.45 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' _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 22.536(5) _cell_length_b 7.7393(16) _cell_length_c 9.223(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.488(7) _cell_angle_gamma 90.00 _cell_volume 1591.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6425 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.8 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9405 _exptl_absorpt_correction_T_max 0.9981 _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 11058 _diffrn_reflns_av_R_equivalents 0.1524 _diffrn_reflns_av_sigmaI/netI 0.1956 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2808 _reflns_number_gt 1216 _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^)+(0.0544P)^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 2808 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1934 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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 0.0378(2) 0.9442(6) 0.8369(5) 0.0424(13) Uani 1 1 d . . . H1A H 0.0122 0.8558 0.8720 0.064 Uiso 1 1 calc R . . H1B H 0.0160 1.0540 0.8247 0.064 Uiso 1 1 calc R . . H1C H 0.0742 0.9588 0.9084 0.064 Uiso 1 1 calc R . . C2 C 0.0548(2) 0.8888(5) 0.6916(5) 0.0360(13) Uani 1 1 d . . . H2A H 0.0177 0.8636 0.6230 0.043 Uiso 1 1 calc R . . H2B H 0.0783 0.7805 0.7060 0.043 Uiso 1 1 calc R . . C3 C 0.0910(2) 1.0221(5) 0.6227(5) 0.0359(13) Uani 1 1 d . . . H3A H 0.1283 1.0460 0.6909 0.043 Uiso 1 1 calc R . . H3B H 0.0677 1.1309 0.6098 0.043 Uiso 1 1 calc R . . C4 C 0.1077(2) 0.9687(6) 0.4754(5) 0.0369(12) Uani 1 1 d . . . H4A H 0.1338 0.8653 0.4893 0.044 Uiso 1 1 calc R . . H4B H 0.0707 0.9361 0.4092 0.044 Uiso 1 1 calc R . . C5 C 0.1398(2) 1.1094(5) 0.4030(5) 0.0403(13) Uani 1 1 d . . . H5A H 0.1133 1.2120 0.3889 0.048 Uiso 1 1 calc R . . H5B H 0.1762 1.1429 0.4706 0.048 Uiso 1 1 calc R . . C6 C 0.1579(2) 1.0623(6) 0.2579(5) 0.0428(13) Uani 1 1 d . . . H6A H 0.1218 1.0300 0.1884 0.051 Uiso 1 1 calc R . . H6B H 0.1766 1.1635 0.2172 0.051 Uiso 1 1 calc R . . C7 C 0.2305(2) 0.8656(6) 0.1715(5) 0.0359(13) Uani 1 1 d . . . C8 C 0.3021(2) 0.6399(6) 0.1188(5) 0.0324(12) Uani 1 1 d . . . C9 C 0.2936(2) 0.4631(6) 0.0990(5) 0.0370(12) Uani 1 1 d . . . H9 H 0.2645 0.4043 0.1453 0.044 Uiso 1 1 calc R . . C10 C 0.3276(2) 0.3739(6) 0.0122(5) 0.0427(14) Uani 1 1 d . . . H10 H 0.3209 0.2535 -0.0018 0.051 Uiso 1 1 calc R . . C11 C 0.3703(2) 0.4516(7) -0.0543(5) 0.0417(13) Uani 1 1 d . . . C12 C 0.3797(2) 0.6291(6) -0.0306(5) 0.0429(14) Uani 1 1 d . . . H12 H 0.4096 0.6871 -0.0744 0.051 Uiso 1 1 calc R . . C13 C 0.3455(2) 0.7202(6) 0.0560(5) 0.0381(13) Uani 1 1 d . . . H13 H 0.3525 0.8403 0.0719 0.046 Uiso 1 1 calc R . . C14 C 0.4080(3) 0.3551(6) -0.1496(6) 0.0635(17) Uani 1 1 d . . . H14A H 0.3837 0.3374 -0.2470 0.076 Uiso 1 1 calc R . . H14B H 0.4426 0.4289 -0.1639 0.076 Uiso 1 1 calc R . . C15 C 0.4306(3) 0.1901(9) -0.0952(7) 0.101(3) Uani 1 1 d . . . H15A H 0.3961 0.1133 -0.0880 0.121 Uiso 1 1 calc R . . H15B H 0.4524 0.2064 0.0053 0.121 Uiso 1 1 calc R . . C16 C 0.4718(2) 0.1004(7) -0.1851(5) 0.0658(18) Uani 1 1 d . . . H16A H 0.4853 -0.0092 -0.1381 0.099 Uiso 1 1 calc R . . H16B H 0.5066 0.1741 -0.1922 0.099 Uiso 1 1 calc R . . H16C H 0.4503 0.0776 -0.2835 0.099 Uiso 1 1 calc R . . N1 N 0.19978(17) 0.9195(4) 0.2734(4) 0.0354(10) Uani 1 1 d . . . H1 H 0.2053 0.8648 0.3579 0.042 Uiso 1 1 d R . . N2 N 0.26612(17) 0.7278(5) 0.2088(4) 0.0374(11) Uani 1 1 d . . . H2 H 0.2673 0.6885 0.2987 0.045 Uiso 1 1 d R . . S1 S 0.22188(6) 0.95749(14) 0.00275(13) 0.0401(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(3) 0.032(2) 0.047(3) 0.003(2) 0.011(3) 0.001(3) C2 0.039(3) 0.027(2) 0.044(3) 0.001(2) 0.010(2) 0.003(2) C3 0.040(3) 0.027(2) 0.041(3) 0.003(2) 0.004(2) 0.004(2) C4 0.042(3) 0.029(2) 0.040(3) -0.001(2) 0.005(2) 0.004(2) C5 0.054(4) 0.027(2) 0.043(3) 0.002(2) 0.017(3) 0.003(2) C6 0.057(4) 0.032(3) 0.041(3) 0.005(2) 0.011(3) 0.010(3) C7 0.044(3) 0.029(2) 0.034(3) 0.000(2) 0.005(3) -0.001(3) C8 0.026(3) 0.041(3) 0.030(3) 0.004(2) 0.005(2) 0.003(3) C9 0.041(3) 0.037(2) 0.035(3) 0.003(3) 0.011(2) -0.007(3) C10 0.039(4) 0.040(3) 0.051(4) -0.005(3) 0.012(3) 0.003(3) C11 0.041(4) 0.041(3) 0.046(3) 0.000(3) 0.017(3) 0.008(3) C12 0.048(4) 0.042(3) 0.042(3) 0.008(3) 0.017(3) 0.001(3) C13 0.032(3) 0.036(3) 0.046(3) -0.001(2) 0.005(3) 0.001(3) C14 0.076(5) 0.043(3) 0.078(4) -0.001(3) 0.035(4) 0.011(3) C15 0.120(6) 0.129(6) 0.059(5) 0.024(4) 0.028(4) 0.091(5) C16 0.076(5) 0.074(4) 0.045(4) -0.001(3) 0.002(3) 0.036(3) N1 0.047(3) 0.035(2) 0.026(2) 0.0047(17) 0.010(2) 0.0102(19) N2 0.046(3) 0.041(2) 0.027(2) 0.0081(18) 0.012(2) 0.009(2) S1 0.0553(9) 0.0315(6) 0.0343(8) 0.0028(6) 0.0092(6) 0.0034(7) _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 1.509(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.513(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.516(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.500(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.447(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N1 1.314(5) . ? C7 N2 1.349(5) . ? C7 S1 1.696(5) . ? C8 C13 1.359(6) . ? C8 C9 1.390(6) . ? C8 N2 1.418(6) . ? C9 C10 1.372(6) . ? C9 H9 0.9500 . ? C10 C11 1.357(6) . ? C10 H10 0.9500 . ? C11 C12 1.402(6) . ? C11 C14 1.507(7) . ? C12 C13 1.381(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.438(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.502(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 H1 0.8799 . ? N2 H2 0.8799 . ? 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 113.8(4) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 114.2(4) . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C5 C4 C3 113.3(4) . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 115.4(4) . . ? C6 C5 H5A 108.4 . . ? C4 C5 H5A 108.4 . . ? C6 C5 H5B 108.4 . . ? C4 C5 H5B 108.4 . . ? H5A C5 H5B 107.5 . . ? N1 C6 C5 110.9(4) . . ? N1 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? N1 C7 N2 115.1(4) . . ? N1 C7 S1 121.5(4) . . ? N2 C7 S1 123.3(4) . . ? C13 C8 C9 119.2(5) . . ? C13 C8 N2 122.7(4) . . ? C9 C8 N2 118.0(5) . . ? C10 C9 C8 119.6(5) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C11 C10 C9 122.4(5) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C10 C11 C12 117.6(5) . . ? C10 C11 C14 122.9(5) . . ? C12 C11 C14 119.5(5) . . ? C13 C12 C11 120.5(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C8 C13 C12 120.7(4) . . ? C8 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C11 115.9(5) . . ? C15 C14 H14A 108.3 . . ? C11 C14 H14A 108.3 . . ? C15 C14 H14B 108.3 . . ? C11 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 115.7(6) . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15B 108.4 . . ? C16 C15 H15B 108.4 . . ? H15A C15 H15B 107.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C7 N1 C6 125.2(4) . . ? C7 N1 H1 117.4 . . ? C6 N1 H1 117.4 . . ? C7 N2 C8 126.9(4) . . ? C7 N2 H2 116.6 . . ? C8 N2 H2 116.5 . . ? 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 C2 C3 C4 -179.2(4) . . . . ? C2 C3 C4 C5 175.6(4) . . . . ? C3 C4 C5 C6 179.3(4) . . . . ? C4 C5 C6 N1 -61.9(5) . . . . ? C13 C8 C9 C10 -2.4(6) . . . . ? N2 C8 C9 C10 179.8(4) . . . . ? C8 C9 C10 C11 1.0(7) . . . . ? C9 C10 C11 C12 0.6(7) . . . . ? C9 C10 C11 C14 179.9(4) . . . . ? C10 C11 C12 C13 -0.9(7) . . . . ? C14 C11 C12 C13 179.8(4) . . . . ? C9 C8 C13 C12 2.2(7) . . . . ? N2 C8 C13 C12 179.8(4) . . . . ? C11 C12 C13 C8 -0.5(7) . . . . ? C10 C11 C14 C15 -43.2(8) . . . . ? C12 C11 C14 C15 136.0(6) . . . . ? C11 C14 C15 C16 -175.8(5) . . . . ? N2 C7 N1 C6 -178.7(4) . . . . ? S1 C7 N1 C6 -2.2(6) . . . . ? C5 C6 N1 C7 -169.3(4) . . . . ? N1 C7 N2 C8 177.5(4) . . . . ? S1 C7 N2 C8 1.0(6) . . . . ? C13 C8 N2 C7 58.1(6) . . . . ? C9 C8 N2 C7 -124.3(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 2.83 3.595(4) 146.6 4_576 N2 H2 S1 0.88 2.54 3.346(4) 153.4 4_576 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.264 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.059 data_p-Ethyl _audit_creation_method SHELXL-97 _chemical_compound_source ; Nathalie Busschaert ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H24 N2 S' _chemical_formula_sum 'C15 H24 N2 S' _chemical_formula_weight 264.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0032 0.0015 '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' 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1181 0.1169 '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 13.07(2) _cell_length_b 13.28(3) _cell_length_c 8.885(18) _cell_angle_alpha 90.00 _cell_angle_beta 93.56(2) _cell_angle_gamma 90.00 _cell_volume 1539(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2681 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 26.6 _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9941 _exptl_absorpt_correction_T_max 0.9980 _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 10433 _diffrn_reflns_av_R_equivalents 0.2114 _diffrn_reflns_av_sigmaI/netI 0.1373 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 24.20 _reflns_number_total 2637 _reflns_number_gt 1418 _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^)+(0.1728P)^2^+0.2975P] 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 SHELXL _refine_ls_extinction_coef 0.016(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2637 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1794 _refine_ls_R_factor_gt 0.1039 _refine_ls_wR_factor_ref 0.3229 _refine_ls_wR_factor_gt 0.2559 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.6158(6) 0.6004(7) 0.2027(8) 0.090(3) Uani 1 1 d . . . H1A H 0.6694 0.5708 0.2710 0.135 Uiso 1 1 calc R . . H1B H 0.6410 0.6632 0.1607 0.135 Uiso 1 1 calc R . . H1C H 0.5978 0.5531 0.1206 0.135 Uiso 1 1 calc R . . C2 C 0.5253(5) 0.6212(7) 0.2858(8) 0.081(2) Uani 1 1 d . . . H2A H 0.5447 0.6676 0.3701 0.097 Uiso 1 1 calc R . . H2B H 0.5015 0.5576 0.3299 0.097 Uiso 1 1 calc R . . C3 C 0.4364(5) 0.6681(6) 0.1884(7) 0.0638(19) Uani 1 1 d . . . C4 C 0.3696(4) 0.6065(5) 0.1009(7) 0.0610(18) Uani 1 1 d . . . H4 H 0.3783 0.5355 0.1037 0.073 Uiso 1 1 calc R . . C5 C 0.2899(4) 0.6487(5) 0.0090(7) 0.0572(17) Uani 1 1 d . . . H5 H 0.2459 0.6063 -0.0520 0.069 Uiso 1 1 calc R . . C6 C 0.2748(4) 0.7521(5) 0.0065(6) 0.0509(16) Uani 1 1 d . . . C7 C 0.3432(4) 0.8143(5) 0.0916(6) 0.0546(16) Uani 1 1 d . . . H7 H 0.3358 0.8854 0.0871 0.066 Uiso 1 1 calc R . . C8 C 0.4218(5) 0.7710(6) 0.1826(7) 0.0654(19) Uani 1 1 d . . . H8 H 0.4666 0.8134 0.2422 0.078 Uiso 1 1 calc R . . C9 C 0.1231(4) 0.8649(5) -0.0461(6) 0.0498(15) Uani 1 1 d . . . C10 C 0.0361(4) 0.8463(4) -0.3055(6) 0.0492(15) Uani 1 1 d . . . H10A H 0.0269 0.7726 -0.2971 0.059 Uiso 1 1 calc R . . H10B H 0.0977 0.8590 -0.3622 0.059 Uiso 1 1 calc R . . C11 C -0.0581(5) 0.8925(5) -0.3902(6) 0.0514(16) Uani 1 1 d . . . H11A H -0.1189 0.8814 -0.3312 0.062 Uiso 1 1 calc R . . H11B H -0.0479 0.9660 -0.3995 0.062 Uiso 1 1 calc R . . C12 C -0.0779(4) 0.8476(4) -0.5461(6) 0.0492(15) Uani 1 1 d . . . H12A H -0.0876 0.7740 -0.5366 0.059 Uiso 1 1 calc R . . H12B H -0.0170 0.8589 -0.6049 0.059 Uiso 1 1 calc R . . C13 C -0.1727(5) 0.8927(5) -0.6330(6) 0.0518(16) Uani 1 1 d . . . H13A H -0.2341 0.8778 -0.5771 0.062 Uiso 1 1 calc R . . H13B H -0.1649 0.9668 -0.6368 0.062 Uiso 1 1 calc R . . C14 C -0.1898(5) 0.8531(6) -0.7924(7) 0.0654(19) Uani 1 1 d . . . H14A H -0.1956 0.7788 -0.7893 0.079 Uiso 1 1 calc R . . H14B H -0.1296 0.8701 -0.8499 0.079 Uiso 1 1 calc R . . C15 C -0.2871(5) 0.8969(6) -0.8749(7) 0.075(2) Uani 1 1 d . . . H15A H -0.2948 0.8692 -0.9772 0.113 Uiso 1 1 calc R . . H15B H -0.2812 0.9704 -0.8802 0.113 Uiso 1 1 calc R . . H15C H -0.3471 0.8790 -0.8198 0.113 Uiso 1 1 calc R . . N1 N 0.1910(3) 0.7924(4) -0.0865(5) 0.0510(13) Uani 1 1 d . . . H1 H 0.1822 0.7682 -0.1786 0.061 Uiso 1 1 calc R . . N2 N 0.0505(4) 0.8909(4) -0.1536(5) 0.0494(13) Uani 1 1 d . . . H2 H 0.0077 0.9389 -0.1310 0.059 Uiso 1 1 calc R . . S001 S 0.12585(11) 0.91904(11) 0.12579(16) 0.0521(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 C1 0.070(5) 0.137(8) 0.062(5) 0.004(4) -0.007(4) 0.049(5) C2 0.045(4) 0.137(7) 0.058(4) 0.009(4) -0.020(3) 0.008(4) C3 0.046(3) 0.100(6) 0.043(4) 0.011(3) -0.018(3) -0.003(3) C4 0.041(3) 0.085(5) 0.055(4) 0.010(3) -0.012(3) 0.006(3) C5 0.048(3) 0.077(5) 0.045(4) 0.005(3) -0.012(3) -0.001(3) C6 0.042(3) 0.076(5) 0.033(3) 0.006(3) -0.011(3) -0.001(3) C7 0.036(3) 0.079(5) 0.048(3) -0.004(3) -0.007(3) 0.000(3) C8 0.049(4) 0.090(6) 0.054(4) -0.005(4) -0.018(3) -0.008(3) C9 0.041(3) 0.070(4) 0.036(3) 0.004(3) -0.014(3) -0.006(3) C10 0.054(3) 0.060(4) 0.032(3) -0.001(2) -0.008(3) 0.000(3) C11 0.049(3) 0.058(4) 0.046(4) 0.001(3) -0.015(3) 0.000(3) C12 0.052(3) 0.059(4) 0.034(3) -0.002(3) -0.013(3) 0.004(3) C13 0.048(3) 0.074(4) 0.032(3) -0.002(3) -0.009(3) 0.002(3) C14 0.058(4) 0.088(5) 0.047(4) -0.006(3) -0.021(3) 0.003(3) C15 0.058(4) 0.117(6) 0.049(4) 0.000(4) -0.021(3) 0.000(4) N1 0.047(3) 0.071(4) 0.034(2) 0.000(2) -0.008(2) 0.005(2) N2 0.052(3) 0.058(3) 0.036(2) -0.001(2) -0.015(2) 0.003(2) S001 0.0498(10) 0.0675(12) 0.0367(9) -0.0036(7) -0.0159(7) -0.0007(7) _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 1.460(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.537(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.381(10) . ? C3 C4 1.397(9) . ? C4 C5 1.400(8) . ? C4 H4 0.9500 . ? C5 C6 1.387(9) . ? C5 H5 0.9500 . ? C6 C7 1.403(8) . ? C6 N1 1.435(7) . ? C7 C8 1.391(8) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N2 1.349(7) . ? C9 N1 1.372(8) . ? C9 S001 1.686(7) . ? C10 N2 1.475(7) . ? C10 C11 1.530(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.515(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.539(8) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.515(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.542(9) . ? 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 . . ? C1 C2 C3 113.6(6) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C8 C3 C4 118.6(6) . . ? C8 C3 C2 121.3(6) . . ? C4 C3 C2 120.1(7) . . ? C3 C4 C5 120.5(7) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.3(6) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 119.3(5) . . ? C5 C6 N1 118.8(5) . . ? C7 C6 N1 121.9(6) . . ? C8 C7 C6 119.5(6) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C3 C8 C7 121.8(6) . . ? C3 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? N2 C9 N1 115.6(5) . . ? N2 C9 S001 120.4(5) . . ? N1 C9 S001 123.9(4) . . ? N2 C10 C11 110.0(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 112.3(5) . . ? C12 C11 H11A 109.1 . . ? C10 C11 H11A 109.1 . . ? C12 C11 H11B 109.1 . . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? C11 C12 C13 113.1(5) . . ? 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 113.6(5) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 112.5(6) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? 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 126.5(5) . . ? C9 N1 H1 116.8 . . ? C6 N1 H1 116.8 . . ? C9 N2 C10 126.1(5) . . ? C9 N2 H2 116.9 . . ? C10 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 N2 H2 S001 0.88 2.57 3.437(7) 167.8 3_575 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 24.20 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.432 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.087 #===END