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

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.

Source: Acta Crystallographica Section E - May 12, 2023 Category: Chemistry Authors: Hong, D. Lee, K. Tags: crystal structure benzimidazolone hydrogen bond research communications Source Type: research