Crystal Structure, Hirshfeld Surface Analysis and DFT Studies of 2-[(2

Abstract

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)degrees. The configuration about the C=N bond is E, stabilized by a strong intramolecular O-H center dot center dot center dot N hydrogen bond that forms an S(6) ring motif. In the crystal, C-H center dot center dot center dot O and C-H center dot center dot center dot N interactions lead to the formation of sheets perpendicular to the a axis. C-H center dot center dot center dot pi interactions, forming polymeric chains along the a-axis direction, connect these sheets into a threedimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H center dot center dot center dot H and C center dot center dot center dot H/H center dot center dot center dot 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.