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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...

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Autores principales: Durka, Krzysztof, Kliś, Tomasz, Serwatowski, Janusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
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].
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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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