Bis{2-[1-(8-hydroxy-2-quinolylmethyl)-1H-benzimidazol-2-yl]quinolin-8-ol} toluene solvate

Abstract

Crystals of the title compound, 2C26H18N4O2·C7H8, were obtained from the reaction of 8-hydroxyquinoline with 1,2-phenylenediamine in methanol and recrystallized from toluene. The compound contains three essentially planar ring systems: the benzimidazole ring (r.m.s. deviation = 0.039 Å) and two 8-hydroxyquinoline rings (r.m.s. deviations of 0.0056 Å in both rings). The benzimidazole ring and one 8-hydroxyquinoline ring are almost co-planar, forming a dihdral angle of 3.1 (2)°. The other 8-hydroxyquinoline ring is almost perpendicular to the benzimidazole plane with a dihedral angle of 86.2 (2)°. Intramolecular O—H...N contacts are present. The crystal structure is stabilized by intermolecular O—H...N interactions. The complete toluene molecule is generated by crystallographic inversion symmetry; therefore its methyl group is disordered over two sites of equal occupancy.