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Isonicotinamide–2-naphthoic acid (1/1)
In the title 1:1 adduct, C(6)H(6)N(2)O·C(11)H(8)O(2), the amide group is slightly twisted out of the plane of the aromatic ring, with a C—C—C—N torsion angle of 25.11 (19)°, whereas the carboxylic acid group is approximately coplanar with the bicylic ring system, with a C—C—C—O torsion angle of 10...
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/PMC3239073/ https://www.ncbi.nlm.nih.gov/pubmed/22199921 http://dx.doi.org/10.1107/S1600536811050057 |
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author | Madeley, Lee G. Levendis, Demetrius C. Lemmerer, Andreas |
author_facet | Madeley, Lee G. Levendis, Demetrius C. Lemmerer, Andreas |
author_sort | Madeley, Lee G. |
collection | PubMed |
description | In the title 1:1 adduct, C(6)H(6)N(2)O·C(11)H(8)O(2), the amide group is slightly twisted out of the plane of the aromatic ring, with a C—C—C—N torsion angle of 25.11 (19)°, whereas the carboxylic acid group is approximately coplanar with the bicylic ring system, with a C—C—C—O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide molecules form a dimer via N—H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid molecule is hydrogen bonded to the pyridine unit of an isonicotinamide molecule via an O—H⋯N hydrogen bond. This gives rise to a centrosymmetric four-molecule chain, which is cross-linked by further N—H⋯O hydrogen bonds from the amide group. |
format | Online Article Text |
id | pubmed-3239073 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-32390732011-12-23 Isonicotinamide–2-naphthoic acid (1/1) Madeley, Lee G. Levendis, Demetrius C. Lemmerer, Andreas Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title 1:1 adduct, C(6)H(6)N(2)O·C(11)H(8)O(2), the amide group is slightly twisted out of the plane of the aromatic ring, with a C—C—C—N torsion angle of 25.11 (19)°, whereas the carboxylic acid group is approximately coplanar with the bicylic ring system, with a C—C—C—O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide molecules form a dimer via N—H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid molecule is hydrogen bonded to the pyridine unit of an isonicotinamide molecule via an O—H⋯N hydrogen bond. This gives rise to a centrosymmetric four-molecule chain, which is cross-linked by further N—H⋯O hydrogen bonds from the amide group. International Union of Crystallography 2011-11-25 /pmc/articles/PMC3239073/ /pubmed/22199921 http://dx.doi.org/10.1107/S1600536811050057 Text en © Madeley 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 Madeley, Lee G. Levendis, Demetrius C. Lemmerer, Andreas Isonicotinamide–2-naphthoic acid (1/1) |
title | Isonicotinamide–2-naphthoic acid (1/1) |
title_full | Isonicotinamide–2-naphthoic acid (1/1) |
title_fullStr | Isonicotinamide–2-naphthoic acid (1/1) |
title_full_unstemmed | Isonicotinamide–2-naphthoic acid (1/1) |
title_short | Isonicotinamide–2-naphthoic acid (1/1) |
title_sort | isonicotinamide–2-naphthoic acid (1/1) |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3239073/ https://www.ncbi.nlm.nih.gov/pubmed/22199921 http://dx.doi.org/10.1107/S1600536811050057 |
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