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Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate
The title compound, C(20)H(16)ClNO(3)S, is built up from three fused rings, one five- and two six-membered rings, linked to a 3-ethoxycarbonyl group and to a 4-chlorophenyl ring. The hydropyran ring has a flattened envelope conformation, with the C atom substituted by the 4-chlorophenyl ring as...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571428/ https://www.ncbi.nlm.nih.gov/pubmed/26396828 http://dx.doi.org/10.1107/S2056989015014085 |
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author | Bakhouch, Mohamed Mahfoud, Asmae El Yazidi, Mohamed Saadi, Mohamed El Ammari, Lahcen |
author_facet | Bakhouch, Mohamed Mahfoud, Asmae El Yazidi, Mohamed Saadi, Mohamed El Ammari, Lahcen |
author_sort | Bakhouch, Mohamed |
collection | PubMed |
description | The title compound, C(20)H(16)ClNO(3)S, is built up from three fused rings, one five- and two six-membered rings, linked to a 3-ethoxycarbonyl group and to a 4-chlorophenyl ring. The hydropyran ring has a flattened envelope conformation, with the C atom substituted by the 4-chlorophenyl ring as the flap (displaced by 0.077 (2) Å from the plane through the other atoms). The fused three-ring system is quasi-planar (r.m.s. deviation = 0.057 Å), with the largest deviation from the mean plane being 0.106 (1) Å for the C atom substituted by the 4-chlorophenyl ring. The 4-chlorophenyl ring is approximately perpendicular to the mean plane of the fused ring system, as indicated by the dihedral angle of 77.32 (6)° between their mean planes. There is an intramolecular N—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R (2) (2)(12) ring motif. There are also short intermolecular Cl⋯O interactions present [3.1226 (12) Å] between neighbouring molecules. |
format | Online Article Text |
id | pubmed-4571428 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-45714282015-09-22 Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate Bakhouch, Mohamed Mahfoud, Asmae El Yazidi, Mohamed Saadi, Mohamed El Ammari, Lahcen Acta Crystallogr E Crystallogr Commun Data Reports The title compound, C(20)H(16)ClNO(3)S, is built up from three fused rings, one five- and two six-membered rings, linked to a 3-ethoxycarbonyl group and to a 4-chlorophenyl ring. The hydropyran ring has a flattened envelope conformation, with the C atom substituted by the 4-chlorophenyl ring as the flap (displaced by 0.077 (2) Å from the plane through the other atoms). The fused three-ring system is quasi-planar (r.m.s. deviation = 0.057 Å), with the largest deviation from the mean plane being 0.106 (1) Å for the C atom substituted by the 4-chlorophenyl ring. The 4-chlorophenyl ring is approximately perpendicular to the mean plane of the fused ring system, as indicated by the dihedral angle of 77.32 (6)° between their mean planes. There is an intramolecular N—H⋯O hydrogen bond forming an S(6) ring motif. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R (2) (2)(12) ring motif. There are also short intermolecular Cl⋯O interactions present [3.1226 (12) Å] between neighbouring molecules. International Union of Crystallography 2015-07-31 /pmc/articles/PMC4571428/ /pubmed/26396828 http://dx.doi.org/10.1107/S2056989015014085 Text en © Bakhouch et al. 2015 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 | Data Reports Bakhouch, Mohamed Mahfoud, Asmae El Yazidi, Mohamed Saadi, Mohamed El Ammari, Lahcen Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate |
title | Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate |
title_full | Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate |
title_fullStr | Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate |
title_full_unstemmed | Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate |
title_short | Crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4H-1-benzothieno[3,2-b]pyran-3-carboxylate |
title_sort | crystal structure of ethyl 2-amino-4-(4-chlorophenyl)-4h-1-benzothieno[3,2-b]pyran-3-carboxylate |
topic | Data Reports |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4571428/ https://www.ncbi.nlm.nih.gov/pubmed/26396828 http://dx.doi.org/10.1107/S2056989015014085 |
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