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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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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. |
format | Online Article Text |
id | pubmed-3790413 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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
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title_full | 2-(2-Methylbenzoyl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
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title_fullStr | 2-(2-Methylbenzoyl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
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title_full_unstemmed | 2-(2-Methylbenzoyl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
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title_short | 2-(2-Methylbenzoyl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid
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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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