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N-(4-Chloro-2-methyl­phen­yl)maleamic acid

In the mol­ecular structure of the title compound, C(11)H(10)ClNO(3), the conformation of the N—H bond in the amide segment is syn to the ortho-methyl group in the phenyl ring. The C=O and O—H bonds of the acid group are in the relatively rare anti position with respect to each other. This is an obv...

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Autores principales: Shakuntala, K., Vrábel, Viktor, Gowda, B. Thimme, Kožíšek, Jozef
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238967/
https://www.ncbi.nlm.nih.gov/pubmed/22199816
http://dx.doi.org/10.1107/S1600536811047817
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author Shakuntala, K.
Vrábel, Viktor
Gowda, B. Thimme
Kožíšek, Jozef
author_facet Shakuntala, K.
Vrábel, Viktor
Gowda, B. Thimme
Kožíšek, Jozef
author_sort Shakuntala, K.
collection PubMed
description In the mol­ecular structure of the title compound, C(11)H(10)ClNO(3), the conformation of the N—H bond in the amide segment is syn to the ortho-methyl group in the phenyl ring. The C=O and O—H bonds of the acid group are in the relatively rare anti position with respect to each other. This is an obvious consequence of the hydrogen bond donated to the amide carbonyl group. The central oxobutenoic acid core C(=O)—C=C—C—OH is twisted by 31.65 (6)° out of the plane of the 4-chloro-2-methyl­phenyl ring. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the a axis.
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spelling pubmed-32389672011-12-23 N-(4-Chloro-2-methyl­phen­yl)maleamic acid Shakuntala, K. Vrábel, Viktor Gowda, B. Thimme Kožíšek, Jozef Acta Crystallogr Sect E Struct Rep Online Organic Papers In the mol­ecular structure of the title compound, C(11)H(10)ClNO(3), the conformation of the N—H bond in the amide segment is syn to the ortho-methyl group in the phenyl ring. The C=O and O—H bonds of the acid group are in the relatively rare anti position with respect to each other. This is an obvious consequence of the hydrogen bond donated to the amide carbonyl group. The central oxobutenoic acid core C(=O)—C=C—C—OH is twisted by 31.65 (6)° out of the plane of the 4-chloro-2-methyl­phenyl ring. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the a axis. International Union of Crystallography 2011-11-16 /pmc/articles/PMC3238967/ /pubmed/22199816 http://dx.doi.org/10.1107/S1600536811047817 Text en © Shakuntala et al. 2011 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
Shakuntala, K.
Vrábel, Viktor
Gowda, B. Thimme
Kožíšek, Jozef
N-(4-Chloro-2-methyl­phen­yl)maleamic acid
title N-(4-Chloro-2-methyl­phen­yl)maleamic acid
title_full N-(4-Chloro-2-methyl­phen­yl)maleamic acid
title_fullStr N-(4-Chloro-2-methyl­phen­yl)maleamic acid
title_full_unstemmed N-(4-Chloro-2-methyl­phen­yl)maleamic acid
title_short N-(4-Chloro-2-methyl­phen­yl)maleamic acid
title_sort n-(4-chloro-2-methyl­phen­yl)maleamic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3238967/
https://www.ncbi.nlm.nih.gov/pubmed/22199816
http://dx.doi.org/10.1107/S1600536811047817
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