Crystal structure, Hirshfeld surface analysis and DFT studies of 4-methyl-2-({[4-(trifluoromethyl)-phenyl]imino}methyl)phenol

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Faizi M. S. H., Cinar E. B., Doğan O. E., Aydin A. S., Ağar E., DEGE N., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.76, pp.1325-1335, 2020 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 76
  • Publication Date: 2020
  • Doi Number: 10.1107/s2056989020009615
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.1325-1335
  • Keywords: crystal structure, 2-hydroxy-5-methyl-benzaldehyde, 4-trifluoromethyl-phenylamine., SCHIFF-BASES, DNA-BINDING, COMPLEXES, POLYMERIZATION
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The title compound, C15H12F3NO, crystallizes with one molecule in the asymmetric unit. The configuration of the C = N bond is E and there is an intramolecular O-H center dot center dot center dot N hydrogen bond present, forming an S(6) ring motif. The dihedral angle between the mean planes of the phenol and the 4-trifluoromethylphenyl rings is 44.77 (3)degrees. In the crystal, molecules are linked by C-H center dot center dot center dot O interactions, forming polymeric chains extending along the a-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C center dot center dot center dot H/H center dot center dot center dot C (29.2%), H center dot center dot center dot H (28.6%), F center dot center dot center dot H/H center dot center dot center dot F (25.6%), O center dot center dot center dot H/H center dot center dot center dot O (5.7%) and F center dot center dot center dot F (4.6%) 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 in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The crystal studied was refined as an inversion twin.