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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...

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Autores principales: Aznan, Aina Mardia Akhmad, Abdullah, Zanariah, Ng, Seik Weng, Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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].
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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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