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

  • Sibel Demir Kanmazalp,
  • Pınar Şen,
  • Necmi Dege,
  • Salih Zeki Yildiz,
  • Namık Ozdemir,
  • Irina A. Golenya

DOI
https://doi.org/10.1107/S2056989019006510
Journal volume & issue
Vol. 75, no. 6
pp. 780 – 784

Abstract

Read online

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.

Keywords