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4-Chloro-N-(2,6-dichlorophenyl)benzamide
The title compound, C(13)H(8)Cl(3)NO, crystallizes with four molecules in the asymmetric unit. In the molecular structure, the conformations of the central amide –CONH group show a wide range of dihedral angles with respect to the attached aromatic rings (benzoyl and anilino). The dihedral angles...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969447/ https://www.ncbi.nlm.nih.gov/pubmed/21582902 http://dx.doi.org/10.1107/S160053680902265X |
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author | Tokarčík, Miroslav Gowda, B. Thimme Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut |
author_facet | Tokarčík, Miroslav Gowda, B. Thimme Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut |
author_sort | Tokarčík, Miroslav |
collection | PubMed |
description | The title compound, C(13)H(8)Cl(3)NO, crystallizes with four molecules in the asymmetric unit. In the molecular structure, the conformations of the central amide –CONH group show a wide range of dihedral angles with respect to the attached aromatic rings (benzoyl and anilino). The dihedral angles between the amide group and the benzoyl ring are 8.1 (3), 4.3 (3), 27.8 (1) and 32.7 (2)° in the four molecules. The amide group is twisted out of the plane of the anilino ring, as shown by the dihedral angles of 85.4 (1), 74.3 (1), 88.1 (1) and 77.6 (1)° in the four molecules. The aromatic rings are oriented at dihedral angles of 86.6 (1), 78.0 (1), 60.3 (1) and 69.8 (1)° in the four molecules. The crystal structure is stabilized via intermolecular N—H⋯O hydrogen bonds, aromatic aromatic interactions, short Cl⋯Cl contacts and C—H⋯Cl hydrogen bonds. Intermolecular hydrogen bonds connect the molecules into two distinct chains running along the c axis of the crystal. One molecule forms an inversion dimer in which the main interactions are π–π stacking [centroid–centroid distances = 3.749 (1) and 3.760 (1) Å] and a short Cl⋯Cl contact of 3.408 (1) Å. |
format | Text |
id | pubmed-2969447 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29694472010-12-30 4-Chloro-N-(2,6-dichlorophenyl)benzamide Tokarčík, Miroslav Gowda, B. Thimme Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(8)Cl(3)NO, crystallizes with four molecules in the asymmetric unit. In the molecular structure, the conformations of the central amide –CONH group show a wide range of dihedral angles with respect to the attached aromatic rings (benzoyl and anilino). The dihedral angles between the amide group and the benzoyl ring are 8.1 (3), 4.3 (3), 27.8 (1) and 32.7 (2)° in the four molecules. The amide group is twisted out of the plane of the anilino ring, as shown by the dihedral angles of 85.4 (1), 74.3 (1), 88.1 (1) and 77.6 (1)° in the four molecules. The aromatic rings are oriented at dihedral angles of 86.6 (1), 78.0 (1), 60.3 (1) and 69.8 (1)° in the four molecules. The crystal structure is stabilized via intermolecular N—H⋯O hydrogen bonds, aromatic aromatic interactions, short Cl⋯Cl contacts and C—H⋯Cl hydrogen bonds. Intermolecular hydrogen bonds connect the molecules into two distinct chains running along the c axis of the crystal. One molecule forms an inversion dimer in which the main interactions are π–π stacking [centroid–centroid distances = 3.749 (1) and 3.760 (1) Å] and a short Cl⋯Cl contact of 3.408 (1) Å. International Union of Crystallography 2009-06-20 /pmc/articles/PMC2969447/ /pubmed/21582902 http://dx.doi.org/10.1107/S160053680902265X Text en © Tokarčík 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 Tokarčík, Miroslav Gowda, B. Thimme Kožíšek, Jozef Sowmya, B. P. Fuess, Hartmut 4-Chloro-N-(2,6-dichlorophenyl)benzamide |
title | 4-Chloro-N-(2,6-dichlorophenyl)benzamide |
title_full | 4-Chloro-N-(2,6-dichlorophenyl)benzamide |
title_fullStr | 4-Chloro-N-(2,6-dichlorophenyl)benzamide |
title_full_unstemmed | 4-Chloro-N-(2,6-dichlorophenyl)benzamide |
title_short | 4-Chloro-N-(2,6-dichlorophenyl)benzamide |
title_sort | 4-chloro-n-(2,6-dichlorophenyl)benzamide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969447/ https://www.ncbi.nlm.nih.gov/pubmed/21582902 http://dx.doi.org/10.1107/S160053680902265X |
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