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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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Detalles Bibliográficos
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
Descripción
Sumario: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].