Crystal structure, Hirshfeld surface analysis, calculations of intermolecular interaction energies and energy frameworks and the DFT-optimized molecular structure of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

Abstract

The benzimidazole entity of the title molecule, C17H21N5O, is almost planar (r.m.s. deviation = 0.0262 Å). In the crystal, bifurcated C—H...O hydrogen bonds link individual molecules into layers extending parallel to the ac plane. Two weak C—H...π(ring) interactions may also be effective in the stabilization of the crystal structure. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H...H (57.9%), H...C/C...H (18.1%) and H...O/O...H (14.9%) interactions. Hydrogen bonding and van der Waals interactions are the most dominant forces in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization of the title compound is dominated via dispersion energy contributions. The molecular structure optimized by density functional theory (DFT) at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state.

Keywords

• benzimidazol-2-one
• crystal structure
• triazole
• c—h...π(ring) interaction
• hydrogen bond