Crystal Structure and Hirshfeld Surface Analysis of 4-[4-(1 H -Benzo[ d ]imidazol-2-yl)phenoxy]phthalonitrile Dimethyl Sulfoxide Monosolvate

Abstract

This work presents the synthesis and structural characterization of [4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile, a phthalonitrile derivative carrying a benzimidazole moiety. The compound crystallizes as its dimethyl sulfoxide monosolvate, C 21 H<inf>12</inf>N<inf>4</inf> O·(CH 3)<inf>2</inf> SO. The dihedral angle between the two fused rings in the heterocyclic ring system is 2.11 (1)°, while the phenyl ring attached to the imidazole moiety is inclined by 20.7 (1)° to the latter. In the crystal structure, adjacent molecules are connected by pairs of weak intermolecular C - H...N hydrogen bonds into inversion dimers. N - H...O and C - H...O hydrogen bonds with R<inf>2</inf>1 (7) graph-set motifs are also formed between the organic molecule and the disordered dimethyl sulfoxide solvent [occupancy ratio of 0.623 (5):0.377 (5) for the two sites of the sulfur atom]. Hirshfeld surface analysis and fingerprint plots were used to investigate the intermolecular interactions in the crystalline state. © 2019 Demir Kanmazalp et al.