Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(2-methyl-3-nitro­phen­yl)imino]­meth­yl}phenol

The title compound, C(15)H(14)N(2)O(3), was prepared by condensation of 2-hy­droxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenyl­amine in ethanol. The configuration of the C=N bond is E. An intra­molecular O—H⋯N hydrogen bond is present, forming an S(6) ring motif and inducing the phenol ring and the Schiff base to be nearly coplanar [C—C—N—C torsion angle of 178.53 (13)°]. In the crystal, mol­ecules are linked by C—H⋯O inter­actions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (37.2%), C⋯H (30.7%) and O⋯H (24.9%) inter­actions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared to the experimentally determined mol­ecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.