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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...

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Autores principales: Bakhouch, Mohamed, Mahfoud, Asmae, El Yazidi, Mohamed, Saadi, Mohamed, El Ammari, Lahcen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
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.
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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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