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N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine
In the title compound, C(16)H(13)ClN(4)S, the thienopyridine fused-ring system is nearly planar (r.m.s. deviation = 0.0333 Å) and forms a dihedral angle of 4.4 (3)° with the attached dihydroimidazole ring (r.m.s. deviation = 0.0429 Å) allowing for the formation of an intramolecular (exocyclic amin...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393946/ https://www.ncbi.nlm.nih.gov/pubmed/22798811 http://dx.doi.org/10.1107/S160053681202658X |
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author | Bernardino, Alice M. R. Pinheiro, Luiz C. S. Tiekink, Edward R. T. Wardell, James L. Wardell, Solange M. S. V. |
author_facet | Bernardino, Alice M. R. Pinheiro, Luiz C. S. Tiekink, Edward R. T. Wardell, James L. Wardell, Solange M. S. V. |
author_sort | Bernardino, Alice M. R. |
collection | PubMed |
description | In the title compound, C(16)H(13)ClN(4)S, the thienopyridine fused-ring system is nearly planar (r.m.s. deviation = 0.0333 Å) and forms a dihedral angle of 4.4 (3)° with the attached dihydroimidazole ring (r.m.s. deviation = 0.0429 Å) allowing for the formation of an intramolecular (exocyclic amine)N—H⋯N(imine) hydrogen bond. The benzene rings of the disordered (50:50) –N(H)—C(6)H(4)Cl residue form dihedral angles of 59.1 (3) and 50.59 (15)° with the fused ring system. In the crystal, (imidazole amine)N—H⋯N(pyridine) hydrogen bonds lead to a supramolecular helical chain along the b axis. The chains assemble into layers (ab plane) with inter-digitation of the chlorobenzene rings which results in weak C—H⋯Cl interactions in the c-axis direction. |
format | Online Article Text |
id | pubmed-3393946 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33939462012-07-13 N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine Bernardino, Alice M. R. Pinheiro, Luiz C. S. Tiekink, Edward R. T. Wardell, James L. Wardell, Solange M. S. V. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(16)H(13)ClN(4)S, the thienopyridine fused-ring system is nearly planar (r.m.s. deviation = 0.0333 Å) and forms a dihedral angle of 4.4 (3)° with the attached dihydroimidazole ring (r.m.s. deviation = 0.0429 Å) allowing for the formation of an intramolecular (exocyclic amine)N—H⋯N(imine) hydrogen bond. The benzene rings of the disordered (50:50) –N(H)—C(6)H(4)Cl residue form dihedral angles of 59.1 (3) and 50.59 (15)° with the fused ring system. In the crystal, (imidazole amine)N—H⋯N(pyridine) hydrogen bonds lead to a supramolecular helical chain along the b axis. The chains assemble into layers (ab plane) with inter-digitation of the chlorobenzene rings which results in weak C—H⋯Cl interactions in the c-axis direction. International Union of Crystallography 2012-06-20 /pmc/articles/PMC3393946/ /pubmed/22798811 http://dx.doi.org/10.1107/S160053681202658X Text en © Bernardino et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Bernardino, Alice M. R. Pinheiro, Luiz C. S. Tiekink, Edward R. T. Wardell, James L. Wardell, Solange M. S. V. N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine |
title |
N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine |
title_full |
N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine |
title_fullStr |
N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine |
title_full_unstemmed |
N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine |
title_short |
N-(4-Chlorophenyl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine |
title_sort | n-(4-chlorophenyl)-5-(4,5-dihydro-1h-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3393946/ https://www.ncbi.nlm.nih.gov/pubmed/22798811 http://dx.doi.org/10.1107/S160053681202658X |
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