Abstract
In the title mol-ecule, C11H10N2O, the di-hydro-benzimidazol-2-one moiety is essentially planar, with the prop-2-yn-1-yl substituent rotated well out of this plane. In the crystal, C-HMthy⋯π(ring) inter-actions and C-HProp⋯ODhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = di-hydro) hydrogen bonds form corrugated layers parallel to (10), which are associated through additional C-HBnz⋯ODhyr (Bnz = benzene) hydrogen bonds and head-to-tail, slipped, π-stacking [centroid-to-centroid distance = 3.7712 (7) Å] inter-actions between di-hydro-benzimidazol-2-one moieties. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (44.1%), H⋯C/C⋯H (33.5%) and O⋯H/H⋯O (13.4%) inter-actions. Hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry calculations indicate that in the crystal, C-H⋯O hydrogen-bond energies are 46.8 and 32.5 (for C-HProp⋯ODhyr) and 20.2 (for C-HBnz⋯ODhyr) kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
Highlights
Chemical contextBenzimidazole is an aromatic heterocyclic organic compound that plays an important role in medicinal chemistry and pharmacology
Asmaa Saber,a Mohamed Srhir,a* Tuncer Hokelek,b Joel T
C—HMthyÁ Á Á(ring) interactions and C—HPropÁ Á ÁODhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = dihydro) hydrogen bonds form corrugated layers parallel to (101), which are associated through additional C—HBnzÁ Á ÁODhyr (Bnz = benzene) hydrogen bonds and head-to-tail, slipped, stacking [centroid-to-centroid distance = 3.7712 (7) A ] interactions between dihydrobenzimidazol-2-one moieties
Summary
Benzimidazole is an aromatic heterocyclic organic compound that plays an important role in medicinal chemistry and pharmacology. Benzimidazole derivatives possess many biological activities such as anti-microbial, anti-fungal, anti-histaminic, anti-inflammatory, anti-viral, anti-oxidant, anti-cancer and anti-ulcerative (Farukh & Mubashira, 2009; Ayhan-Kılcıgil et al, 2007; Soderlind et al, 1999; Luo et al, 2011; NavarreteVazquez et al, 2011). They are considered to be an important moiety for the development of molecules of pharmaceutical interest (Mondieig et al, 2013; Lakhrissi et al, 2008). As a continuation of our research on the development of Nsubstituted benzimidazole derivatives and the evaluation of their potential pharmacological activities (Saber et al, 2018a,b, 2020; Ouzidan et al, 2011), we have studied the. Symmetry codes: (v) Àx; Ày þ 1; Àz þ 1; (vi) Àx þ 12; y À 12; Àz þ 32; (vii) Àx þ 32; y À 12; Àz þ 32; (ix) x; y À 1; z
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