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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...

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Autores principales: Tokarčík, Miroslav, Gowda, B. Thimme, Kožíšek, Jozef, Sowmya, B. P., Fuess, Hartmut
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
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.
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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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