Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hy­dr­oxy-5-methyl­benzyl­­idene)amino]­benzo­nitrile

The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hy­droxy-5-methyl­benzaldehyde and 2-amino­benzo­nitrile, and crystallizes in the ortho­rhom­bic space group Pbca. The phenol ring is inclined to the benzo­nitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intra­molecular O—H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, C—H⋯O and C—H⋯N inter­actions lead to the formation of sheets perpendicular to the a axis. C—H⋯π inter­actions, forming polymeric chains along the a-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 inter­actions. The density functional theory (DFT) optimized structure at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined mol­ecular structure and the HOMO–LUMO energy gap is given.