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 R22(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].

Keywords

• arylboronic acid
• hydrogen-bonding interactions
• halogen-bonding interactions
• biphenyl
• THF solvate
• crystal structure