Crystal structure of (2',3,6'-trichlorobiphenyl-2-yl)boronic acid tetrahydrofuran monosolvate

Abstract

The title compound, C12H8BCl3O2·C4H8O, 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].