Crystal structure, Hirshfeld surface analysis and DFT studies of ()-2-{[(3-chloro-4-methyl-phen-yl)imino]-meth-yl}-4-methyl-phenol.

The title compound, CHClNO, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 3-chloro-4-methyl-aniline, and crystallizes in the monoclinic space group 2/c. The 3-chloro-benzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is and an intra-molecular O-H⋯N hydrogen bond forms an (6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H⋯H (43.8%) and C⋯H/H⋯C (26.7%) inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure and the HOMO-LUMO energy gap is provided.