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2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid
In the title compound, C(20)H(13)N(5)O(2), the two pyrazine rings are nearly coplanar with the central pyridine ring, forming dihedral angles of 2.21 (9) and 4.57 (9)°. In contrast, the strong steric hindrance caused by the ortho-carboxyl group on the phenyl ring makes this ring rotate out of the at...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011275/ https://www.ncbi.nlm.nih.gov/pubmed/24860380 http://dx.doi.org/10.1107/S1600536814008496 |
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author | Shuai, Ying Wang, Xiang-Yang Dai, Jing-Wei Wu, Jian-Zhong |
author_facet | Shuai, Ying Wang, Xiang-Yang Dai, Jing-Wei Wu, Jian-Zhong |
author_sort | Shuai, Ying |
collection | PubMed |
description | In the title compound, C(20)H(13)N(5)O(2), the two pyrazine rings are nearly coplanar with the central pyridine ring, forming dihedral angles of 2.21 (9) and 4.57 (9)°. In contrast, the strong steric hindrance caused by the ortho-carboxyl group on the phenyl ring makes this ring rotate out of the attached pyridine ring plane by 52.60 (9)°. The carboxyl group is twisted from the phenyl ring by 22.6 (1)°. In the crystal, aromatic π–π stacking interactions [centroid–centroid distances = 3.9186 (4) and 3.9794 (5) Å] occur between the antiparallel molecules, generating infinite chains along [100]. O—H⋯O hydrogen bonds connect the chains, leading to the formation of a two-dimensional supramolecular network parallel to (010). Intermolecular C—H⋯N hydrogen bonds are also observed. |
format | Online Article Text |
id | pubmed-4011275 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-40112752014-05-23 2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid Shuai, Ying Wang, Xiang-Yang Dai, Jing-Wei Wu, Jian-Zhong Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(20)H(13)N(5)O(2), the two pyrazine rings are nearly coplanar with the central pyridine ring, forming dihedral angles of 2.21 (9) and 4.57 (9)°. In contrast, the strong steric hindrance caused by the ortho-carboxyl group on the phenyl ring makes this ring rotate out of the attached pyridine ring plane by 52.60 (9)°. The carboxyl group is twisted from the phenyl ring by 22.6 (1)°. In the crystal, aromatic π–π stacking interactions [centroid–centroid distances = 3.9186 (4) and 3.9794 (5) Å] occur between the antiparallel molecules, generating infinite chains along [100]. O—H⋯O hydrogen bonds connect the chains, leading to the formation of a two-dimensional supramolecular network parallel to (010). Intermolecular C—H⋯N hydrogen bonds are also observed. International Union of Crystallography 2014-04-18 /pmc/articles/PMC4011275/ /pubmed/24860380 http://dx.doi.org/10.1107/S1600536814008496 Text en © Shuai et al. 2014 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 Shuai, Ying Wang, Xiang-Yang Dai, Jing-Wei Wu, Jian-Zhong 2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid |
title | 2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid |
title_full | 2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid |
title_fullStr | 2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid |
title_full_unstemmed | 2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid |
title_short | 2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid |
title_sort | 2-[2,6-bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4011275/ https://www.ncbi.nlm.nih.gov/pubmed/24860380 http://dx.doi.org/10.1107/S1600536814008496 |
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