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

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 P21/c. The 3-chlorobenzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intramolecular O—H...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...H (43.8%) and C...H/H...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.

Keywords

• crystal structure
• 3-chloro-4-methylaniline
• 2-hydroxy-5-methylbenzaldehyde
• schiff base