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

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(ring) interactions and C—HPropODhyr (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—HBnzODhyr (Bnz = benzene) hydrogen bonds and head-to-tail, slipped, - stacking [centroid-to-centroid distance = 3.7712 (7) A˚ ] 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 HH (44.1%), HC/CH (33.5%) and OH/HO (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—HO hydrogen-bond energies are 46.8 and 32.5 (for C—HPropODhyr) and 20.2 (for C—HBnzODhyr) kJ mol1 . 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.