Abstract
This work presents the synthesis and structural characterization of [4-(1H-benzo[d]imidazol-2-yl)phen-oxy]phthalo-nitrile, a phthalo-nitrile 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 mol-ecules are connected by pairs of weak inter-molecular C-H⋯N hydrogen bonds into inversion dimers. N-H⋯O and C-H⋯O hydrogen bonds with R 2 1(7) graph-set motifs are also formed between the organic mol-ecule 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 inter-molecular inter-actions in the crystalline state.
Highlights
Sibel Demir Kanmazalp,a* Pınar Sen,b Necmi Dege,c* Salih Zeki Yildiz,d Namık Ozdemire and Irina A
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
Adjacent molecules are connected by pairs of weak intermolecular C—HÁ Á ÁN hydrogen bonds into inversion dimers
Summary
Benzimidazole and its derivatives are some of the oldest and chemically most-studied nitrogen-containing aromatic heterocyclic compounds (Srestha et al, 2014) They have a wide range of applications in medicinal chemistry and in biological processes including as anticancer, antiulcer, antifungal and anti-inflammatory agents, and exhibit antimycobacterial and antioxidant activities (El Rashedy & Aboul-Enein, 2013; Gaba et al, 2014; Kathiravan et al, 2012). E75, 780–784 research communications al., 2004; Martınez-Dıaz et al, 2011) In this context, we have recently described a model study, i.e. the synthesis, characterization and Hirshfeld surface analysis of zinc phthalocyanines carrying benzimidazole groups through oxygen bridges to a Zn–Pc core (Sen et al, 2018b). There are weak intermolecular N2—H2Á Á ÁS1A interactions between the the N—H group of the imidazole ring and the disordered dimethyl sulfate solvent, and a C23—H23DÁ Á ÁN4 interaction between one of the methyl groups of the dimethyl sulfoxide solvent and
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