Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate
2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C15H10BrClO3, 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 l...
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doaj-35e0a30f88284b0b87599b1915ef1f502020-11-25T02:15:33ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682014-11-01701130130410.1107/S1600536814021643hg5410Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoateImtiaz Khan0Aliya Ibrar1Shahid Hameed2Jonathan M. White3Jim Simpson4Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanSchool of Chemistry and Bio-21 Institute, University of Melbourne, Parkville, Victoria 3052, AustraliaDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C15H10BrClO3, 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.http://scripts.iucr.org/cgi-bin/paper?S1600536814021643crystal structure2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoatesynthesisπ–π interactionsinversion dimers |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Imtiaz Khan Aliya Ibrar Shahid Hameed Jonathan M. White Jim Simpson |
spellingShingle |
Imtiaz Khan Aliya Ibrar Shahid Hameed Jonathan M. White Jim Simpson Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate Acta Crystallographica Section E crystal structure 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate synthesis π–π interactions inversion dimers |
author_facet |
Imtiaz Khan Aliya Ibrar Shahid Hameed Jonathan M. White Jim Simpson |
author_sort |
Imtiaz Khan |
title |
Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
title_short |
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_sort |
crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E |
issn |
1600-5368 |
publishDate |
2014-11-01 |
description |
2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C15H10BrClO3, 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. |
topic |
crystal structure 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate synthesis π–π interactions inversion dimers |
url |
http://scripts.iucr.org/cgi-bin/paper?S1600536814021643 |
work_keys_str_mv |
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