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2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone

The mol­ecule in the structure of the title compound, C(15)H(11)ClN(2)OS, displays two planar residues [r.m.s. deviation = 0.014 Å for the benzimidazole residue, and the ketone group is co-planar with the benzene ring to which it is attached forming a O—C—C—C torsion angle of −173.18 (14) °] linked...

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Autores principales: Abdel-Aziz, Hatem A., Ng, Seik Weng, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201531/
https://www.ncbi.nlm.nih.gov/pubmed/22064924
http://dx.doi.org/10.1107/S160053681103666X
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author Abdel-Aziz, Hatem A.
Ng, Seik Weng
Tiekink, Edward R. T.
author_facet Abdel-Aziz, Hatem A.
Ng, Seik Weng
Tiekink, Edward R. T.
author_sort Abdel-Aziz, Hatem A.
collection PubMed
description The mol­ecule in the structure of the title compound, C(15)H(11)ClN(2)OS, displays two planar residues [r.m.s. deviation = 0.014 Å for the benzimidazole residue, and the ketone group is co-planar with the benzene ring to which it is attached forming a O—C—C—C torsion angle of −173.18 (14) °] linked at the S atom. The overall shape is based on a twisted V, the dihedral angle formed between the two planes being 82.4 (2) °. The amine-H atom is bifurcated, forming N—H⋯O and N—H⋯S hydrogen bonds leading to dimeric aggregates. These are linked into a supra­molecular chain along the c axis via C—H⋯π hydrogen bonds. Chains form layers in the ab plane being connected along the c axis via weak π–π inter­actions [3.9578 (8) Å] formed between centrosymmetrically related chloro-substituted benzene rings.
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spelling pubmed-32015312011-11-06 2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone Abdel-Aziz, Hatem A. Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers The mol­ecule in the structure of the title compound, C(15)H(11)ClN(2)OS, displays two planar residues [r.m.s. deviation = 0.014 Å for the benzimidazole residue, and the ketone group is co-planar with the benzene ring to which it is attached forming a O—C—C—C torsion angle of −173.18 (14) °] linked at the S atom. The overall shape is based on a twisted V, the dihedral angle formed between the two planes being 82.4 (2) °. The amine-H atom is bifurcated, forming N—H⋯O and N—H⋯S hydrogen bonds leading to dimeric aggregates. These are linked into a supra­molecular chain along the c axis via C—H⋯π hydrogen bonds. Chains form layers in the ab plane being connected along the c axis via weak π–π inter­actions [3.9578 (8) Å] formed between centrosymmetrically related chloro-substituted benzene rings. International Union of Crystallography 2011-09-14 /pmc/articles/PMC3201531/ /pubmed/22064924 http://dx.doi.org/10.1107/S160053681103666X Text en © Abdel-Aziz et al. 2011 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
Abdel-Aziz, Hatem A.
Ng, Seik Weng
Tiekink, Edward R. T.
2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone
title 2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone
title_full 2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone
title_fullStr 2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone
title_full_unstemmed 2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone
title_short 2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone
title_sort 2-(1h-1,3-benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201531/
https://www.ncbi.nlm.nih.gov/pubmed/22064924
http://dx.doi.org/10.1107/S160053681103666X
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