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

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Faizi M. S. H., Cinar E. B., Aydin A. S., Ağar E., DEGE N., Mashrai A.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.76, pp.1320-1328, 2020 (ESCI) identifier identifier identifier

  • 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
  • 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.