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N-(2-Fluorophenyl)cinnamamide
The title compound, C(15)H(12)FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoroaniline and crystallizes with two molecules A and B in the asymmetric unit. The two unique molecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluorobenzene and phen...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983731/ https://www.ncbi.nlm.nih.gov/pubmed/21580305 http://dx.doi.org/10.1107/S1600536810003867 |
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author | Saeed, Aamer Khera, Rasheed Ahmad Simpson, Jim |
author_facet | Saeed, Aamer Khera, Rasheed Ahmad Simpson, Jim |
author_sort | Saeed, Aamer |
collection | PubMed |
description | The title compound, C(15)H(12)FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoroaniline and crystallizes with two molecules A and B in the asymmetric unit. The two unique molecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluorobenzene and phenyl rings are inclined to one another at 73.89 (7) and 79.46 (7)°, respectively, in molecules A and B. The amide C—N—C(O)—C portions of the molecules are planar (r.m.s. deviations = 0.035 and 0.028 Å) and are inclined at 45.51 (9) and 47.71 (9), respectively, to the fluorobenzene rings in molecules A and B. The 2-fluoroacetamide units and the benzene rings each adopt E configurations with respect to the C=C bonds. In the crystal structure, intermolecular N—H⋯O hydrogen bonds augmented by weak C—H⋯π interactions link molecules into rows in a head-to-tail fashion along a. Additional weak C—H⋯O contacts further stabilize the packing, forming a three-dimensional network stacked down a. |
format | Text |
id | pubmed-2983731 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29837312010-12-30 N-(2-Fluorophenyl)cinnamamide Saeed, Aamer Khera, Rasheed Ahmad Simpson, Jim Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(15)H(12)FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoroaniline and crystallizes with two molecules A and B in the asymmetric unit. The two unique molecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluorobenzene and phenyl rings are inclined to one another at 73.89 (7) and 79.46 (7)°, respectively, in molecules A and B. The amide C—N—C(O)—C portions of the molecules are planar (r.m.s. deviations = 0.035 and 0.028 Å) and are inclined at 45.51 (9) and 47.71 (9), respectively, to the fluorobenzene rings in molecules A and B. The 2-fluoroacetamide units and the benzene rings each adopt E configurations with respect to the C=C bonds. In the crystal structure, intermolecular N—H⋯O hydrogen bonds augmented by weak C—H⋯π interactions link molecules into rows in a head-to-tail fashion along a. Additional weak C—H⋯O contacts further stabilize the packing, forming a three-dimensional network stacked down a. International Union of Crystallography 2010-02-06 /pmc/articles/PMC2983731/ /pubmed/21580305 http://dx.doi.org/10.1107/S1600536810003867 Text en © Saeed et al. 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 Khera, Rasheed Ahmad Simpson, Jim N-(2-Fluorophenyl)cinnamamide |
title |
N-(2-Fluorophenyl)cinnamamide |
title_full |
N-(2-Fluorophenyl)cinnamamide |
title_fullStr |
N-(2-Fluorophenyl)cinnamamide |
title_full_unstemmed |
N-(2-Fluorophenyl)cinnamamide |
title_short |
N-(2-Fluorophenyl)cinnamamide |
title_sort | n-(2-fluorophenyl)cinnamamide |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983731/ https://www.ncbi.nlm.nih.gov/pubmed/21580305 http://dx.doi.org/10.1107/S1600536810003867 |
work_keys_str_mv | AT saeedaamer n2fluorophenylcinnamamide AT kherarasheedahmad n2fluorophenylcinnamamide AT simpsonjim n2fluorophenylcinnamamide |