Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)-6-methoxyphenol

The title compound, C₁₈H₁₆N₂O₂, consists of perimidine and methoxyphenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C₄N₂ ring adopting an envelope conformation with the NCN group hinged by 47.44 14;(7)° with respect to the best plane of the other five atoms. In the crystal, O-HPhnl..NPrmdn and N-HPrmdn..OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Weak C-H..p interactions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H..H (49.0%), H..C/C..H (35.8%) and H..O/O..H (12.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the O-HPhnl..NPrmdn and N-HPrmdn..OPhnl hydrogen-bond energies are 58.4 and 38.0 14;kJ 14;mol^-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311 14;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.