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N-(3-Chlorophenyl)-3-nitropyridin-2-amine
The dihedral angle between the benzene and pyridyl rings in the title compound, C(11)H(8)ClN(3)O(2), is 22.65 (10)°, indicating a twisted molecule. The amine H and nitro O atoms form a donor–acceptor pair for an intramolecular N—H⋯O hydrogen bond so that the nitro group is almost coplanar with the...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247465/ https://www.ncbi.nlm.nih.gov/pubmed/22220083 http://dx.doi.org/10.1107/S1600536811044011 |
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author | Aznan, Aina Mardia Akhmad Abdullah, Zanariah Ng, Seik Weng Tiekink, Edward R. T. |
author_facet | Aznan, Aina Mardia Akhmad Abdullah, Zanariah Ng, Seik Weng Tiekink, Edward R. T. |
author_sort | Aznan, Aina Mardia Akhmad |
collection | PubMed |
description | The dihedral angle between the benzene and pyridyl rings in the title compound, C(11)H(8)ClN(3)O(2), is 22.65 (10)°, indicating a twisted molecule. The amine H and nitro O atoms form a donor–acceptor pair for an intramolecular N—H⋯O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O—N—C—C torsion angle = 7.4 (3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C—H⋯Cl interactions that lead to undulating supramolecular chains along [101]. These are connected into sheets by π–π interactions occurring between the benzene rings and between the pyridine rings of translationally related molecules along the b axis [centroid–centroid distances = length of b axis = 3.7157 (2) Å]. |
format | Online Article Text |
id | pubmed-3247465 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32474652012-01-04 N-(3-Chlorophenyl)-3-nitropyridin-2-amine Aznan, Aina Mardia Akhmad Abdullah, Zanariah Ng, Seik Weng Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers The dihedral angle between the benzene and pyridyl rings in the title compound, C(11)H(8)ClN(3)O(2), is 22.65 (10)°, indicating a twisted molecule. The amine H and nitro O atoms form a donor–acceptor pair for an intramolecular N—H⋯O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O—N—C—C torsion angle = 7.4 (3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C—H⋯Cl interactions that lead to undulating supramolecular chains along [101]. These are connected into sheets by π–π interactions occurring between the benzene rings and between the pyridine rings of translationally related molecules along the b axis [centroid–centroid distances = length of b axis = 3.7157 (2) Å]. International Union of Crystallography 2011-10-29 /pmc/articles/PMC3247465/ /pubmed/22220083 http://dx.doi.org/10.1107/S1600536811044011 Text en © Aznan et al. 2011 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 Aznan, Aina Mardia Akhmad Abdullah, Zanariah Ng, Seik Weng Tiekink, Edward R. T. N-(3-Chlorophenyl)-3-nitropyridin-2-amine |
title |
N-(3-Chlorophenyl)-3-nitropyridin-2-amine |
title_full |
N-(3-Chlorophenyl)-3-nitropyridin-2-amine |
title_fullStr |
N-(3-Chlorophenyl)-3-nitropyridin-2-amine |
title_full_unstemmed |
N-(3-Chlorophenyl)-3-nitropyridin-2-amine |
title_short |
N-(3-Chlorophenyl)-3-nitropyridin-2-amine |
title_sort | n-(3-chlorophenyl)-3-nitropyridin-2-amine |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247465/ https://www.ncbi.nlm.nih.gov/pubmed/22220083 http://dx.doi.org/10.1107/S1600536811044011 |
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