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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...

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Autores principales: Khan, Imtiaz, Ibrar, Aliya, Hameed, Shahid, White, Jonathan M., Simpson, Jim
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
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.
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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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