Crystal Structure, Hirshfeld Surface Analysis And InterAction Energy And Dft Studies Of 1-Methyl-3-(Prop-2-Yn-1-Yl)-2,3-DiHydro-1H-1,3-BenzoDiazol-2-One
Mague, Joel T.
Hamou Ahabchane, Noureddine
Sebbar, Nada Kheira
Essassi, El Mokhtar
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The dihydrobenzimidazol-2-one moiety is essentially planar with the prop-2-yn- 1-yl substituent rotated well out of this plane. In the crystal, C—H⋯π(ring) interactions and C—H⋯O hydrogen bonds form corrugated layers parallel to (10), which are associated through additional C—H⋯O hydrogen bonds and head-to-tail, slipped, π-stacking interactions between dihydrobenzimidazol-2-one moieties, In the title molecule, C11H10N2O, the dihydrobenzimidazol-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) interactions and C—HProp⋯ODhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = dihydro) 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] interactions between dihydrobenzimidazol-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%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions 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 molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.