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

Abstract

<jats:p>The title compound, C<jats:sub>15</jats:sub>H<jats:sub>12</jats:sub>N<jats:sub>2</jats:sub>O, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 2-aminobenzonitrile, and crystallizes in the orthorhombic space group <jats:italic>Pbca</jats:italic>. The phenol ring is inclined to the benzonitrile ring by 25.65 (3)°. The configuration about the C=N bond is <jats:italic>E</jats:italic>, stabilized by a strong intramolecular O—H...N hydrogen bond that forms an <jats:italic>S</jats:italic>(6) ring motif. In the crystal, C—H...O and C—H...N interactions lead to the formation of sheets perpendicular to the <jats:italic>a</jats:italic> axis. C—H...π interactions, forming polymeric chains along the <jats:italic>a-</jats:italic>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.</jats:p>