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N-(2-Nitrophenyl)benzamide
In the title compound, C(13)H(10)N(2)O(3), the central C–C(=O)–N–C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitrobenzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plan...
Autores principales: | , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977104/ https://www.ncbi.nlm.nih.gov/pubmed/21583545 http://dx.doi.org/10.1107/S1600536809024271 |
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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(13)H(10)N(2)O(3), the central C–C(=O)–N–C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitrobenzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55 (8)°. An intramolecular N—H⋯O interaction to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C—H⋯O contacts generate two centrosymmetric ring systems with R (2) (2)(14) and R (2) (2)(20) graph-set motifs, forming zigzag chains down the a axis. π–π interactions between adjacent phenyl and nitrobenzene rings [centroid–centroid distance = 3.6849 (6) Å] also form centrosymmetric dimers. These and an additional C—H⋯O hydrogen bond generate an extensive three-dimensional network structure. |
format | Text |
id | pubmed-2977104 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29771042010-12-30 N-(2-Nitrophenyl)benzamide Saeed, Aamer Simpson, Jim Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(13)H(10)N(2)O(3), the central C–C(=O)–N–C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitrobenzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55 (8)°. An intramolecular N—H⋯O interaction to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C—H⋯O contacts generate two centrosymmetric ring systems with R (2) (2)(14) and R (2) (2)(20) graph-set motifs, forming zigzag chains down the a axis. π–π interactions between adjacent phenyl and nitrobenzene rings [centroid–centroid distance = 3.6849 (6) Å] also form centrosymmetric dimers. These and an additional C—H⋯O hydrogen bond generate an extensive three-dimensional network structure. International Union of Crystallography 2009-07-11 /pmc/articles/PMC2977104/ /pubmed/21583545 http://dx.doi.org/10.1107/S1600536809024271 Text en © Saeed and Simpson 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 Saeed, Aamer Simpson, Jim N-(2-Nitrophenyl)benzamide |
title |
N-(2-Nitrophenyl)benzamide |
title_full |
N-(2-Nitrophenyl)benzamide |
title_fullStr |
N-(2-Nitrophenyl)benzamide |
title_full_unstemmed |
N-(2-Nitrophenyl)benzamide |
title_short |
N-(2-Nitrophenyl)benzamide |
title_sort | n-(2-nitrophenyl)benzamide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977104/ https://www.ncbi.nlm.nih.gov/pubmed/21583545 http://dx.doi.org/10.1107/S1600536809024271 |
work_keys_str_mv | AT saeedaamer n2nitrophenylbenzamide AT simpsonjim n2nitrophenylbenzamide |