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Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate
2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C(15)H(10)BrClO(3), was synthesized in a single-step reaction by condensation of 3-bromobenzoic acid with 2-bromo-1-(4-chlorophenyl)ethanone in dimethylformamide in the presence of triethylamine as a catalyst. The structure consists of an aryl...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257351/ https://www.ncbi.nlm.nih.gov/pubmed/25484728 http://dx.doi.org/10.1107/S1600536814021643 |
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author | Khan, Imtiaz Ibrar, Aliya Hameed, Shahid White, Jonathan M. Simpson, Jim |
author_facet | Khan, Imtiaz Ibrar, Aliya Hameed, Shahid White, Jonathan M. Simpson, Jim |
author_sort | Khan, Imtiaz |
collection | PubMed |
description | 2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C(15)H(10)BrClO(3), was synthesized in a single-step reaction by condensation of 3-bromobenzoic acid with 2-bromo-1-(4-chlorophenyl)ethanone in dimethylformamide in the presence of triethylamine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methylene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, molecules form five separate sets of inversion dimers. Three of these are generated by two C—H⋯O interactions and a C—H⋯Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π–π stacking interactions between like aryl rings again form chains of molecules but in this instance along the bc diagonal. These contacts generate infinite layers of molecules parallel to (011) and stack the molecules along the a-axis direction. |
format | Online Article Text |
id | pubmed-4257351 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-42573512014-12-05 Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate Khan, Imtiaz Ibrar, Aliya Hameed, Shahid White, Jonathan M. Simpson, Jim Acta Crystallogr Sect E Struct Rep Online Research Communications 2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C(15)H(10)BrClO(3), was synthesized in a single-step reaction by condensation of 3-bromobenzoic acid with 2-bromo-1-(4-chlorophenyl)ethanone in dimethylformamide in the presence of triethylamine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methylene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, molecules form five separate sets of inversion dimers. Three of these are generated by two C—H⋯O interactions and a C—H⋯Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π–π stacking interactions between like aryl rings again form chains of molecules but in this instance along the bc diagonal. These contacts generate infinite layers of molecules parallel to (011) and stack the molecules along the a-axis direction. International Union of Crystallography 2014-10-08 /pmc/articles/PMC4257351/ /pubmed/25484728 http://dx.doi.org/10.1107/S1600536814021643 Text en © Khan et al. 2014 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 | Research Communications Khan, Imtiaz Ibrar, Aliya Hameed, Shahid White, Jonathan M. Simpson, Jim Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
title | Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
title_full | Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
title_fullStr | Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
title_full_unstemmed | Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
title_short | Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
title_sort | crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4257351/ https://www.ncbi.nlm.nih.gov/pubmed/25484728 http://dx.doi.org/10.1107/S1600536814021643 |
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