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

Dabeen Hong; Kyounghoon Lee

doi:10.1107/S2056989023003961

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

Acta Crystallogr E Crystallogr Commun. 2023 May 12;79(Pt 6):534-537. doi: 10.1107/S2056989023003961. eCollection 2023 May 1.

Authors

Dabeen Hong¹, Kyounghoon Lee¹

Affiliation

¹ Department of Chemical Education and Research Institute of Natural Sciences, Gyeongsang National University, Gyeongsangnam-do 52828, Republic of Korea.

Abstract

The polymorphic structures (I and II) of 3-phenyl-1H-1,3-benzo-diazol-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 inter-action than in I, as confirmed by the shorter inter-centroid distance [3.3257 (8) Å in II in comparison to 3.6862 (7) Å in I]. Overall, the supra-molecular inter-actions of I and II are distinct, presumably originating from the variation in the dihedral angle.

Keywords: benzimidazolone; crystal structure; hydrogen bond.

Grants and funding

Funding for this research was provided by: National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (2021R1G1A1093332 and 2022R1F1A1064158).