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In this manuscript the mol­ecular and supra­molecular structure of 2′,3,6′-tri­chloro­biphenyl-2-ylboronic acid tetra­hydro­furan monosolvate is presented, 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].

In the title biphenyl derivative, the dihedral angle between the benzene rings is 52.84 (10)°. In the crystal, mol­ecules are linked by two pairs of N—H⋯O hydrogen bonds, forming chains propagating along [101]., In the title biphenyl derivative, C12H9N3O4, the dihedral angle between the benzene rings is 52.84 (10)°. The nitro group attached to the benzene ring is inclined to the ring by 4.03 (2)°, while the nitro group attached to the amino-substituted benzene ring is inclined to the ring by 8.84 (2)°. In the crystal, mol­ecules are linked by two pairs of N—H⋯O hydrogen bonds, forming chains propagating along [101]. Within the chains, these N—H⋯O hydrogen bonds result in the formation of R 2 2(20) and R 2 2(14) ring motifs. The latter ring motif is reinforced by a pair of C—H⋯O hydrogen bonds, enclosing R 2 1(6) ring motifs. The chains are linked by a second C—H⋯O hydrogen bond, forming a three-dimensional supra­molecular structure.

The whole molecule of the title compound, C22H28Br2O2, is generated by twofold rotation symmetry. The dihedral angle of the biphenyl moiety is 85.05 (11)°. The hydroxy groups show intramolecular O—H...π interactions without any other hydrogen-bond acceptors. In the crystal, there are no other significant intermolecular interactions present.

The title compound, C13H4BrF4N, synthesized from 1,4′-bromoiodobenzene and 4-bromo-2,3,5,6-tetrafluorobenzonitrile in a coupling reaction was found to crystallize in the orthorhombic space groupP212121. The two phenyl rings are rotated with respect to each other by 40.6 (6)°. The molecules interactviaaryl–perfluoroaryl stacking [3.796 (2) and 3.773 (2) Å], resulting in intermolecular chains along thea-axis direction. C—H...F contacts of about 2.45 Å connect these chains. In contrast to the structure of the parent compound 4′-bromobiphenyl-4-carbonitrile, CN...Br contacts that could have given rise to a linear arrangement of the biphenyl molecules desirable for non-linear optical (NLO) materials are not observed in the packing. Instead, several Br...F [3.2405 (17) and 3.2777 (18) Å] and F...F [2.894 (2) Å] contacts of side-on type II form an intermolecular network of zigzag chains. The crystal studied was refined as an inversion twin.

The complete molecule of the title compound, C14H8N2, is generated by a twofold rotation axis located at the midpoint of the biphenyl C—C bond. The dihedral angle between the symmetry-related phenyl rings is 46.16 (3)°. In the crystal, molecules are linked by slipped parallel π–π interactions [centroid–centroid distance = 3.9451 (7) Å, normal distance = 3.6293 (5) Å, slippage 1.547 Å], forming columns along theb-axis direction.