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2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid

The crystal structure of the title compound, C(15)H(12)O(3), displays catemeric aggregation involving O—H⋯O hydrogen bonds progressing from the carboxyl group of one mol­ecule to the ketone O atom of another glide-related neighbor. The mol­ecule is twisted, with the toluene 80.61 (3)° out of plane w...

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Autores principales: Platosz, Natalia A., Lalancette, Roger A., Thompson, Hugh W., Newman, Jacob M., Schachter, Ari
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3790413/
https://www.ncbi.nlm.nih.gov/pubmed/24098232
http://dx.doi.org/10.1107/S1600536813025099
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author Platosz, Natalia A.
Lalancette, Roger A.
Thompson, Hugh W.
Newman, Jacob M.
Schachter, Ari
author_facet Platosz, Natalia A.
Lalancette, Roger A.
Thompson, Hugh W.
Newman, Jacob M.
Schachter, Ari
author_sort Platosz, Natalia A.
collection PubMed
description The crystal structure of the title compound, C(15)H(12)O(3), displays catemeric aggregation involving O—H⋯O hydrogen bonds progressing from the carboxyl group of one mol­ecule to the ketone O atom of another glide-related neighbor. The mol­ecule is twisted, with the toluene 80.61 (3)° out of plane with respect to the phenyl group of the benzoic acid. The acid group makes a dihedral angle of 13.79 (14)° with the attached phenyl ring. The mol­ecules are achiral, but the space group glide planes create alternating conformational chirality in the chain units. The four hydrogen-bonding chains progress along [001] in an A—A—B—B pattern (right-to-left versus left-to-right), and are related to each other by the center of symmetry at (0.5, 0.5, 0.5) in the chosen cell. There is one close contact (2.54 Å) between a phenyl H atom and the acid carbonyl from a symmetry-related mol­ecule.
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spelling pubmed-37904132013-10-04 2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid Platosz, Natalia A. Lalancette, Roger A. Thompson, Hugh W. Newman, Jacob M. Schachter, Ari Acta Crystallogr Sect E Struct Rep Online Organic Papers The crystal structure of the title compound, C(15)H(12)O(3), displays catemeric aggregation involving O—H⋯O hydrogen bonds progressing from the carboxyl group of one mol­ecule to the ketone O atom of another glide-related neighbor. The mol­ecule is twisted, with the toluene 80.61 (3)° out of plane with respect to the phenyl group of the benzoic acid. The acid group makes a dihedral angle of 13.79 (14)° with the attached phenyl ring. The mol­ecules are achiral, but the space group glide planes create alternating conformational chirality in the chain units. The four hydrogen-bonding chains progress along [001] in an A—A—B—B pattern (right-to-left versus left-to-right), and are related to each other by the center of symmetry at (0.5, 0.5, 0.5) in the chosen cell. There is one close contact (2.54 Å) between a phenyl H atom and the acid carbonyl from a symmetry-related mol­ecule. International Union of Crystallography 2013-09-18 /pmc/articles/PMC3790413/ /pubmed/24098232 http://dx.doi.org/10.1107/S1600536813025099 Text en © Platosz et al. 2013 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
Platosz, Natalia A.
Lalancette, Roger A.
Thompson, Hugh W.
Newman, Jacob M.
Schachter, Ari
2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
title 2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
title_full 2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
title_fullStr 2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
title_full_unstemmed 2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
title_short 2-(2-Methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
title_sort 2-(2-methyl­benzo­yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3790413/
https://www.ncbi.nlm.nih.gov/pubmed/24098232
http://dx.doi.org/10.1107/S1600536813025099
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