Crystal structure and Hirshfeld surface analysis of 4-[4-(1H-benzo[d]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate

Acta Crystallographica Section E: Crystallographic Communications

Pınar Şen¹  Namık Ozdemir²  Sibel Demir Kanmazalp³  Necmi Dege⁴  Salih Zeki Yildiz⁵  Irina A. Golenya⁶ 

[1] Centre for Nanotechnology Innovation, Department of Chemistry, Rhodes University, Grahamstown, South Africa;Department of Mathematics and Science Education, Faculty of Education, Ondokuz Mayıs University, Samsun, Turkey;Gaziantep University, Technical Sciences, 27310, Gaziantep, Turkey;Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139 Samsun, Turkey;Sakarya University, Faculty of Arts and Sciences, Department of Chemistry, 54187, Sakarya, Turkey;Taras Shevchenko National University of Kyiv, Department of Chemistry, 64, Vladimirska Str., Kiev 01601, Ukraine;

关键词: crystal structure;    phthalonitrile;    imidazole;    Hirshfeld analysis;    hydrogen bonds;   

DOI  :  10.1107/S2056989019006510

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown