Polymorphic structures of 3-phenyl-1H-1,3-benzodiazol-2(3H)-one

Abstract

The polymorphic structures (I and II) of 3-phenyl-1H-1,3-benzodiazol-2(3H)-one, C13H10N2O, acquired from pentane diffusion into the solution in THF, are reported. The structures show negligible differences in bond distances and angles, but the C—N—C—C torsion angles between the backbone and the phenyl substituent, 123.02 (15)° for I and 137.18 (11)° for II, are different. Compound I features a stronger C=O...H—N hydrogen bond than that in II, while the structure of II exhibits a stronger π–π interaction than in I, as confirmed by the shorter intercentroid distance [3.3257 (8) Å in II in comparison to 3.6862 (7) Å in I]. Overall, the supramolecular interactions of I and II are distinct, presumably originating from the variation in the dihedral angle.