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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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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. |
format | Online Article Text |
id | pubmed-3238967 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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