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N-(2,3-Dimethylphenyl)benzamide
The conformation of the N—H bond in the structure of the title compound, C(15)H(15)NO, is anti to the ortho and meta-methyl substituents in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho and meta-chloro substituents in N-(2,3-dichlorophenyl)benzami...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977665/ https://www.ncbi.nlm.nih.gov/pubmed/21584008 http://dx.doi.org/10.1107/S1600536809012112 |
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author | Gowda, B. Thimme Tokarčík, Miroslav Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut |
author_facet | Gowda, B. Thimme Tokarčík, Miroslav Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut |
author_sort | Gowda, B. Thimme |
collection | PubMed |
description | The conformation of the N—H bond in the structure of the title compound, C(15)H(15)NO, is anti to the ortho and meta-methyl substituents in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho and meta-chloro substituents in N-(2,3-dichlorophenyl)benzamide. Furthermore, the conformations of N—H and C=O bonds in the amide group are anti to each other, similar to those observed in other benzanilides. The dihedral angle between the benzoyl and aniline rings is 84.1 (2)°. The amide group is twisted by 23.0 (3)° out of the plane of the benzoyl ring. The structure exhibits positional disorder over the aniline ring, with site occupancies of 0.80 (1) and 0.20 (1) for the major and minor components, respectively. In the crystal, molecules are connected through N—H⋯O hydrogen bonds into chains running along the b axis. An intramolecular C—H⋯O close contact occurs. |
format | Text |
id | pubmed-2977665 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29776652010-12-30 N-(2,3-Dimethylphenyl)benzamide Gowda, B. Thimme Tokarčík, Miroslav Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut Acta Crystallogr Sect E Struct Rep Online Organic Papers The conformation of the N—H bond in the structure of the title compound, C(15)H(15)NO, is anti to the ortho and meta-methyl substituents in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho and meta-chloro substituents in N-(2,3-dichlorophenyl)benzamide. Furthermore, the conformations of N—H and C=O bonds in the amide group are anti to each other, similar to those observed in other benzanilides. The dihedral angle between the benzoyl and aniline rings is 84.1 (2)°. The amide group is twisted by 23.0 (3)° out of the plane of the benzoyl ring. The structure exhibits positional disorder over the aniline ring, with site occupancies of 0.80 (1) and 0.20 (1) for the major and minor components, respectively. In the crystal, molecules are connected through N—H⋯O hydrogen bonds into chains running along the b axis. An intramolecular C—H⋯O close contact occurs. International Union of Crystallography 2009-04-08 /pmc/articles/PMC2977665/ /pubmed/21584008 http://dx.doi.org/10.1107/S1600536809012112 Text en © Gowda et al. 2009 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 Gowda, B. Thimme Tokarčík, Miroslav Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut N-(2,3-Dimethylphenyl)benzamide |
title |
N-(2,3-Dimethylphenyl)benzamide |
title_full |
N-(2,3-Dimethylphenyl)benzamide |
title_fullStr |
N-(2,3-Dimethylphenyl)benzamide |
title_full_unstemmed |
N-(2,3-Dimethylphenyl)benzamide |
title_short |
N-(2,3-Dimethylphenyl)benzamide |
title_sort | n-(2,3-dimethylphenyl)benzamide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977665/ https://www.ncbi.nlm.nih.gov/pubmed/21584008 http://dx.doi.org/10.1107/S1600536809012112 |
work_keys_str_mv | AT gowdabthimme n23dimethylphenylbenzamide AT tokarcikmiroslav n23dimethylphenylbenzamide AT kozisekjozef n23dimethylphenylbenzamide AT sowmyabp n23dimethylphenylbenzamide AT fuesshartmut n23dimethylphenylbenzamide |