Acta Crystallographica Section E: Crystallographic Communications (Jun 2019)
Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-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, C21H12N4O·(CH3)2SO. 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 R21(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.
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