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

Abstract

The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 3-chloro-4-methylaniline, and crystallizes in the monoclinic space group P2(1)/c. The 3-chlorobenzene ring is inclined to the phenol ring by 9.38 (11)degrees. The configuration about the C = N bond is E and an intramolecular O-H center dot center dot center dot N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H center dot center dot center dot H (43.8%) and C center dot center dot center dot H/H center dot center dot center dot C (26.7%) 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 provided.