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2-Chloro-N-(4-methoxyphenyl)benzamide
In the title compound, C(14)H(12)ClNO(2), the chloro- and methoxy-substituted benzene rings are close to orthogonal [dihedral angle = 79.20 (3)°]. These rings also make angles of 45.9 (3) and 33.5 (3)° with the amide –CONH– unit. The methoxy substituent lies close to the methoxybenzene ring plan...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009019/ https://www.ncbi.nlm.nih.gov/pubmed/21589131 http://dx.doi.org/10.1107/S1600536810043035 |
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author | Saeed, Aamer Simpson, Jim |
author_facet | Saeed, Aamer Simpson, Jim |
author_sort | Saeed, Aamer |
collection | PubMed |
description | In the title compound, C(14)H(12)ClNO(2), the chloro- and methoxy-substituted benzene rings are close to orthogonal [dihedral angle = 79.20 (3)°]. These rings also make angles of 45.9 (3) and 33.5 (3)° with the amide –CONH– unit. The methoxy substituent lies close to the methoxybenzene ring plane, with a maximum deviation of 0.142 (3) Å for the methyl C atom. The N—H bond is anti to the 2-chloro substituent of the aniline ring. In the crystal structure, intermolecular N—H⋯O hydrogen bonds form C(4) chains augmented by a weak C—H⋯O interaction involving an ortho H atom of the methoxy benzene ring that generates an R (2) (1)(6) motif. The chains stack the molecules into columns down the b axis. Adjacent columns are linked by additional C—H⋯O and C—H⋯π contacts, generating a three-dimensional network. |
format | Text |
id | pubmed-3009019 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30090192010-12-30 2-Chloro-N-(4-methoxyphenyl)benzamide Saeed, Aamer Simpson, Jim Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(14)H(12)ClNO(2), the chloro- and methoxy-substituted benzene rings are close to orthogonal [dihedral angle = 79.20 (3)°]. These rings also make angles of 45.9 (3) and 33.5 (3)° with the amide –CONH– unit. The methoxy substituent lies close to the methoxybenzene ring plane, with a maximum deviation of 0.142 (3) Å for the methyl C atom. The N—H bond is anti to the 2-chloro substituent of the aniline ring. In the crystal structure, intermolecular N—H⋯O hydrogen bonds form C(4) chains augmented by a weak C—H⋯O interaction involving an ortho H atom of the methoxy benzene ring that generates an R (2) (1)(6) motif. The chains stack the molecules into columns down the b axis. Adjacent columns are linked by additional C—H⋯O and C—H⋯π contacts, generating a three-dimensional network. International Union of Crystallography 2010-10-30 /pmc/articles/PMC3009019/ /pubmed/21589131 http://dx.doi.org/10.1107/S1600536810043035 Text en © Saeed and Simpson 2010 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 Saeed, Aamer Simpson, Jim 2-Chloro-N-(4-methoxyphenyl)benzamide |
title | 2-Chloro-N-(4-methoxyphenyl)benzamide |
title_full | 2-Chloro-N-(4-methoxyphenyl)benzamide |
title_fullStr | 2-Chloro-N-(4-methoxyphenyl)benzamide |
title_full_unstemmed | 2-Chloro-N-(4-methoxyphenyl)benzamide |
title_short | 2-Chloro-N-(4-methoxyphenyl)benzamide |
title_sort | 2-chloro-n-(4-methoxyphenyl)benzamide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009019/ https://www.ncbi.nlm.nih.gov/pubmed/21589131 http://dx.doi.org/10.1107/S1600536810043035 |
work_keys_str_mv | AT saeedaamer 2chloron4methoxyphenylbenzamide AT simpsonjim 2chloron4methoxyphenylbenzamide |