Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-di­hydro-1H-perimidin-2-yl)phenol

The asymmetric unit of the title compound, C17H14N2O, contains two independent mol­ecules each consisting of perimidine and phenol units. The tricyclic perimidine units contain naphthalene ring systems and non-planar C4N2 rings adopting envelope conformations with the C atoms of the NCN groups hinged by 44.11 (7) and 48.50 (6)° with respect to the best planes of the other five atoms. Intra­molecular O—H⋯N hydrogen bonds may help to consolidate the mol­ecular conformations. The two independent mol­ecules are linked through an N—H⋯O hydrogen bond. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (52.9%) and H⋯C/C⋯H (39.5%) inter­actions. Hydrogen bonding and van der Waals inter­actions are the dominant inter­actions in the crystal packing. 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.