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4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid
In the title compound, C(13)H(13)NO(4), the N—C(=O) bond length of 1.354 (2) Å is indicative of amide-type resonance. The dihedral angle between the mean planes of the benzene ring and oxoamine group is 36.4 (3)°, while the mean plane of the 2-methylidene group is inclined by 84.2 (01)° from that...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120591/ https://www.ncbi.nlm.nih.gov/pubmed/25161547 http://dx.doi.org/10.1107/S1600536814012562 |
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author | Narayana, B. Nayak, Prakash S. Sarojini, Balladka K. Jasinski, Jerry P. |
author_facet | Narayana, B. Nayak, Prakash S. Sarojini, Balladka K. Jasinski, Jerry P. |
author_sort | Narayana, B. |
collection | PubMed |
description | In the title compound, C(13)H(13)NO(4), the N—C(=O) bond length of 1.354 (2) Å is indicative of amide-type resonance. The dihedral angle between the mean planes of the benzene ring and oxoamine group is 36.4 (3)°, while the mean plane of the 2-methylidene group is inclined by 84.2 (01)° from that of the oxoamine group. In the crystal, classical O—H⋯O hydrogen bonds formed by the carboxylic acid groups and weak N—H⋯O weak interactions formed by the amide groups and supported by weak C—H⋯O interactions between the 2-methylidene, phenyl and acetyl groups with the carboxylic acid, oxoamine and acetyl O atoms, together link the molecules into dimeric chains along [010]. The O—H⋯O hydrogen bonds form R (2) (2)(8) graph-set motifs. |
format | Online Article Text |
id | pubmed-4120591 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-41205912014-08-26 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid Narayana, B. Nayak, Prakash S. Sarojini, Balladka K. Jasinski, Jerry P. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(13)H(13)NO(4), the N—C(=O) bond length of 1.354 (2) Å is indicative of amide-type resonance. The dihedral angle between the mean planes of the benzene ring and oxoamine group is 36.4 (3)°, while the mean plane of the 2-methylidene group is inclined by 84.2 (01)° from that of the oxoamine group. In the crystal, classical O—H⋯O hydrogen bonds formed by the carboxylic acid groups and weak N—H⋯O weak interactions formed by the amide groups and supported by weak C—H⋯O interactions between the 2-methylidene, phenyl and acetyl groups with the carboxylic acid, oxoamine and acetyl O atoms, together link the molecules into dimeric chains along [010]. The O—H⋯O hydrogen bonds form R (2) (2)(8) graph-set motifs. International Union of Crystallography 2014-06-07 /pmc/articles/PMC4120591/ /pubmed/25161547 http://dx.doi.org/10.1107/S1600536814012562 Text en © Narayana et al. 2014 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 Narayana, B. Nayak, Prakash S. Sarojini, Balladka K. Jasinski, Jerry P. 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid |
title | 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid |
title_full | 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid |
title_fullStr | 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid |
title_full_unstemmed | 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid |
title_short | 4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid |
title_sort | 4-[(4-acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4120591/ https://www.ncbi.nlm.nih.gov/pubmed/25161547 http://dx.doi.org/10.1107/S1600536814012562 |
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