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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...

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Autores principales: Shuai, Ying, Wang, Xiang-Yang, Dai, Jing-Wei, Wu, Jian-Zhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
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.
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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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