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Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate
The title compound, C(12)H(8)BCl(3)O(2)·C(4)H(8)O, crystallizes as a tetrahydrofuran monosolvate. The boronic acid group adopts a syn–anti conformation and is significantly twisted along the carbon–boron bond by 69.2 (1)°, due to considerable steric hindrance from the 2′,6′-dichlorophenyl group...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4719816/ https://www.ncbi.nlm.nih.gov/pubmed/26870407 http://dx.doi.org/10.1107/S205698901502054X |
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author | Durka, Krzysztof Kliś, Tomasz Serwatowski, Janusz |
author_facet | Durka, Krzysztof Kliś, Tomasz Serwatowski, Janusz |
author_sort | Durka, Krzysztof |
collection | PubMed |
description | The title compound, C(12)H(8)BCl(3)O(2)·C(4)H(8)O, crystallizes as a tetrahydrofuran monosolvate. The boronic acid group adopts a syn–anti conformation and is significantly twisted along the carbon–boron bond by 69.2 (1)°, due to considerable steric hindrance from the 2′,6′-dichlorophenyl group that is located ortho to the boronic acid substituent. The phenyl rings of the biphenyl are almost perpendicular to one another, with a dihedral angle of 87.9 (1)° between them. In the crystal, adjacent molecules are linked via O—H⋯O interactions to form centrosymmetric dimers with R (2) (2)(8) motifs, which have recently been shown to be energetically very favourable. The hydroxy groups are in an anti conformation and are also engaged in hydrogen-bonding interactions with the O atom of the tetrahydrofuran solvent molecule. Cl⋯Cl halogen-bonding interactions [Cl⋯Cl = 3.464 (1) Å] link neigbouring dimers into chains running along [010]. Further aggregation occurs due to an additional Cl⋯Cl halogen bond [Cl⋯Cl = 3.387 (1) Å]. |
format | Online Article Text |
id | pubmed-4719816 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-47198162016-02-11 Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate Durka, Krzysztof Kliś, Tomasz Serwatowski, Janusz Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(12)H(8)BCl(3)O(2)·C(4)H(8)O, crystallizes as a tetrahydrofuran monosolvate. The boronic acid group adopts a syn–anti conformation and is significantly twisted along the carbon–boron bond by 69.2 (1)°, due to considerable steric hindrance from the 2′,6′-dichlorophenyl group that is located ortho to the boronic acid substituent. The phenyl rings of the biphenyl are almost perpendicular to one another, with a dihedral angle of 87.9 (1)° between them. In the crystal, adjacent molecules are linked via O—H⋯O interactions to form centrosymmetric dimers with R (2) (2)(8) motifs, which have recently been shown to be energetically very favourable. The hydroxy groups are in an anti conformation and are also engaged in hydrogen-bonding interactions with the O atom of the tetrahydrofuran solvent molecule. Cl⋯Cl halogen-bonding interactions [Cl⋯Cl = 3.464 (1) Å] link neigbouring dimers into chains running along [010]. Further aggregation occurs due to an additional Cl⋯Cl halogen bond [Cl⋯Cl = 3.387 (1) Å]. International Union of Crystallography 2015-11-07 /pmc/articles/PMC4719816/ /pubmed/26870407 http://dx.doi.org/10.1107/S205698901502054X Text en © Durka et al. 2015 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 | Research Communications Durka, Krzysztof Kliś, Tomasz Serwatowski, Janusz Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate |
title | Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate |
title_full | Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate |
title_fullStr | Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate |
title_full_unstemmed | Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate |
title_short | Crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate |
title_sort | crystal structure of (2′,3,6′-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4719816/ https://www.ncbi.nlm.nih.gov/pubmed/26870407 http://dx.doi.org/10.1107/S205698901502054X |
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