Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)-imino]methyl}-4-methylphenol
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.76, pp.1320-1328, 2020 (ESCI, Scopus)
- Publication Type: Article / Article
- Volume: 76
- Publication Date: 2020
- Doi Number: 10.1107/s2056989020009421
- Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
- Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
- Page Numbers: pp.1320-1328
- Keywords: crystal structure, 3-chloro-4-methyl-aniline, 2-hydroxy-5-methylbenzaldehyde, Schiff base, SCHIFF, COMPLEXES, IMINES
- Open Archive Collection: AVESIS Open Access Collection
- Ondokuz Mayıs University Affiliated: Yes
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.