Crystal Structure, Hirshfeld Surface Analysis and DFT Studies of 2-[(2-hy-droxy-5-methyl-benzyl-idene)amino]-benzo-nitrile

The title compound, CHNO, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 2-amino-benzo-nitrile, and crystallizes in the ortho-rhom-bic space group . The phenol ring is inclined to the benzo-nitrile ring by 25.65 (3)°. The configuration about the C=N bond is , stabilized by a strong intra-molecular O-H⋯N hydrogen bond that forms an (6) ring motif. In the crystal, C-H⋯O and C-H⋯N inter-actions lead to the formation of sheets perpendicular to the axis. C-H⋯π inter-actions, forming polymeric chains along the axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H⋯H and C⋯H/H⋯C 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 given.