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N-(3-Nitro­phen­yl)maleamic acid

In the title compound, C(10)H(8)N(2)O(5), the mol­ecule is slightly distorted from planarity. The mol­ecular structure is stabilized by two intra­molecular hydrogen bonds. The first is a short O—H⋯O hydrogen bond (H⋯O distance = 1.57 Å) within the maleamic acid unit and the second is a C—H⋯O hydroge...

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Autores principales: Gowda, B. Thimme, Tokarčík, Miroslav, Shakuntala, K., Kožíšek, Jozef, Fuess, Hartmut
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007040/
https://www.ncbi.nlm.nih.gov/pubmed/21587897
http://dx.doi.org/10.1107/S1600536810022245
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author Gowda, B. Thimme
Tokarčík, Miroslav
Shakuntala, K.
Kožíšek, Jozef
Fuess, Hartmut
author_facet Gowda, B. Thimme
Tokarčík, Miroslav
Shakuntala, K.
Kožíšek, Jozef
Fuess, Hartmut
author_sort Gowda, B. Thimme
collection PubMed
description In the title compound, C(10)H(8)N(2)O(5), the mol­ecule is slightly distorted from planarity. The mol­ecular structure is stabilized by two intra­molecular hydrogen bonds. The first is a short O—H⋯O hydrogen bond (H⋯O distance = 1.57 Å) within the maleamic acid unit and the second is a C—H⋯O hydrogen bond (H⋯O distance = 2.24 Å) which connects the amide group with the benzene ring. The nitro group is twisted by 6.2 (2)° out of the plane of the benzene ring. The crystal structure manifests a variety of hydrogen bonding. The packing is dominated by a strong inter­molecular N—H⋯O inter­action which links the mol­ecules into chains running along the b axis. The chains within a plane are further assembled by three additional types of inter­molecular C—H⋯O hydrogen bonds to form a sheet parallel to the ([Image: see text]01) plane.
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spelling pubmed-30070402010-12-30 N-(3-Nitro­phen­yl)maleamic acid Gowda, B. Thimme Tokarčík, Miroslav Shakuntala, K. Kožíšek, Jozef Fuess, Hartmut Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(10)H(8)N(2)O(5), the mol­ecule is slightly distorted from planarity. The mol­ecular structure is stabilized by two intra­molecular hydrogen bonds. The first is a short O—H⋯O hydrogen bond (H⋯O distance = 1.57 Å) within the maleamic acid unit and the second is a C—H⋯O hydrogen bond (H⋯O distance = 2.24 Å) which connects the amide group with the benzene ring. The nitro group is twisted by 6.2 (2)° out of the plane of the benzene ring. The crystal structure manifests a variety of hydrogen bonding. The packing is dominated by a strong inter­molecular N—H⋯O inter­action which links the mol­ecules into chains running along the b axis. The chains within a plane are further assembled by three additional types of inter­molecular C—H⋯O hydrogen bonds to form a sheet parallel to the ([Image: see text]01) plane. International Union of Crystallography 2010-06-16 /pmc/articles/PMC3007040/ /pubmed/21587897 http://dx.doi.org/10.1107/S1600536810022245 Text en © Gowda 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
Gowda, B. Thimme
Tokarčík, Miroslav
Shakuntala, K.
Kožíšek, Jozef
Fuess, Hartmut
N-(3-Nitro­phen­yl)maleamic acid
title N-(3-Nitro­phen­yl)maleamic acid
title_full N-(3-Nitro­phen­yl)maleamic acid
title_fullStr N-(3-Nitro­phen­yl)maleamic acid
title_full_unstemmed N-(3-Nitro­phen­yl)maleamic acid
title_short N-(3-Nitro­phen­yl)maleamic acid
title_sort n-(3-nitro­phen­yl)maleamic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007040/
https://www.ncbi.nlm.nih.gov/pubmed/21587897
http://dx.doi.org/10.1107/S1600536810022245
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