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Syntheses and crystal structure of 4-[(pyridin-3-yl)diazen­yl]morpholine and 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline

Syntheses and crystal structure of 4-[(pyridin-3-yl)diazen­yl]morpholine and 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline
Syntheses and crystal structure of 4-[(pyridin-3-yl)diazen­yl]morpholine and 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline
Two new heterocyclic 1,2,3-triazenes were synthesized by diazo­tation of 3-amino­pyridine following respectively by coupling with morpholine or 1,2,3,4-tetra­hydro­quinoline. 4-[(Pyridin-3-yl)diazen­yl]morpholine (I), C9H12N4O, has monoclinic P21/c symmetry at 100 K, while 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline (II), C14H14N4, has monoclinic P21/n symmetry at 100 K. These 1,2,3-triazene derivatives were synthesized by the organic medium method by coupling reactions of 3-amino­pyridine with morpholine and 1,2,3,4-tetra­hydro­quinoline, respectively, and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The mol­ecule of compound I consists of pyridine and morpholine rings connected by an azo moiety (–N=N–). In the mol­ecule of II, the pyridine ring and the 1,2,3,4-tetra­hydro­quinoline unit are also connected by an azo moiety. The double- and single-bond distances in the triazene chain are comparable for the two compounds. In both crystal structures, the mol­ecules are connected by C—H⋯N inter­actions, forming infinite chains for I and layers parallel to the bc plane for II.
1,2,3,4-Tetrahydroquinolein, 1,2,3-Triazenes, crystal structure, morpholine, pyridine
2056-9890
74-78
Sokhna, Seynabou
a96ee661-f145-463f-950e-c2235d277253
Seck, Insa
e2f6caa4-ddc4-480c-8103-65b76c2cd848
Thiam, Ibrahima El Hadj
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Presset, Marc
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Ndoye, Samba Fama
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Ba, Lalla Aïcha
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Samb, Issa
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Coles, Simon J.
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Orton, James
4e2a471f-9e11-4cb4-abb6-d0398047939f
Seck, Matar
bc1f804c-cc84-4920-a7fa-5495a25cc227
Le Gall, Erwan
5ac500ed-b205-43b6-b528-cb87065a3afe
Gaye, Mohamed
e5a7f444-74c9-43ed-9323-69c883018ed6
Sokhna, Seynabou
a96ee661-f145-463f-950e-c2235d277253
Seck, Insa
e2f6caa4-ddc4-480c-8103-65b76c2cd848
Thiam, Ibrahima El Hadj
6acaca31-33fd-478a-adc1-99cdc35d938a
Presset, Marc
8bc986c2-7cca-4f26-83cb-85d48dbf56a4
Ndoye, Samba Fama
fb24c250-ca52-4cc0-b81c-809121b84ba0
Ba, Lalla Aïcha
0fc15d79-a461-458c-a53c-f0ef9acd5ac8
Samb, Issa
c5eebfb1-f7f5-43df-b676-d59b0a12f82f
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Orton, James
4e2a471f-9e11-4cb4-abb6-d0398047939f
Seck, Matar
bc1f804c-cc84-4920-a7fa-5495a25cc227
Le Gall, Erwan
5ac500ed-b205-43b6-b528-cb87065a3afe
Gaye, Mohamed
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Sokhna, Seynabou, Seck, Insa, Thiam, Ibrahima El Hadj, Presset, Marc, Ndoye, Samba Fama, Ba, Lalla Aïcha, Samb, Issa, Coles, Simon J., Orton, James, Seck, Matar, Le Gall, Erwan and Gaye, Mohamed (2023) Syntheses and crystal structure of 4-[(pyridin-3-yl)diazen­yl]morpholine and 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline. Acta Crystallographica Section E: Crystallographic Communications, E79, 74-78. (doi:10.1107/S2056989023000129).

Record type: Article

Abstract

Two new heterocyclic 1,2,3-triazenes were synthesized by diazo­tation of 3-amino­pyridine following respectively by coupling with morpholine or 1,2,3,4-tetra­hydro­quinoline. 4-[(Pyridin-3-yl)diazen­yl]morpholine (I), C9H12N4O, has monoclinic P21/c symmetry at 100 K, while 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline (II), C14H14N4, has monoclinic P21/n symmetry at 100 K. These 1,2,3-triazene derivatives were synthesized by the organic medium method by coupling reactions of 3-amino­pyridine with morpholine and 1,2,3,4-tetra­hydro­quinoline, respectively, and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The mol­ecule of compound I consists of pyridine and morpholine rings connected by an azo moiety (–N=N–). In the mol­ecule of II, the pyridine ring and the 1,2,3,4-tetra­hydro­quinoline unit are also connected by an azo moiety. The double- and single-bond distances in the triazene chain are comparable for the two compounds. In both crystal structures, the mol­ecules are connected by C—H⋯N inter­actions, forming infinite chains for I and layers parallel to the bc plane for II.

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Accepted/In Press date: 4 January 2023
e-pub ahead of print date: 4 January 2023
Published date: February 2023
Additional Information: Publisher Copyright: © 2023 International Union of Crystallography. All rights reserved.
Keywords: 1,2,3,4-Tetrahydroquinolein, 1,2,3-Triazenes, crystal structure, morpholine, pyridine

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Local EPrints ID: 475724
URI: http://eprints.soton.ac.uk/id/eprint/475724
ISSN: 2056-9890
PURE UUID: 98202a9e-7176-4305-ae30-ddbe68b1dc0b
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 27 Mar 2023 16:33
Last modified: 06 Jun 2024 01:37

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Contributors

Author: Seynabou Sokhna
Author: Insa Seck
Author: Ibrahima El Hadj Thiam
Author: Marc Presset
Author: Samba Fama Ndoye
Author: Lalla Aïcha Ba
Author: Issa Samb
Author: Simon J. Coles ORCID iD
Author: James Orton
Author: Matar Seck
Author: Erwan Le Gall
Author: Mohamed Gaye

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