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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...

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Autores principales: Narayana, B., Nayak, Prakash S., Sarojini, Balladka K., Jasinski, Jerry P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
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.
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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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