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

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

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.76, pp.1551-1561, 2020 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 76
  • Publication Date: 2020
  • Doi Number: 10.1107/s2056989020011652
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.1551-1561
  • Keywords: crystal structure, 2-hydroxy-5-methyl-benzaldehyde, 2-methyl-3-nitro-phenylamine, Schiff base, INTERMOLECULAR INTERACTIONS, QUANTITATIVE-ANALYSIS
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The title compound, C15H14N2O3, was prepared by condensation of 2-hydroxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenylamine in ethanol. The configuration of the C=N bond is E. An intramolecular O-H center dot center dot center dot N hydrogen bond is present, forming an S(6) ring motif and inducing the phenol ring and the Schiff base to be nearly coplanar [C- C-N-C torsion angle of 178.53 (13)degrees]. In the crystal, molecules are linked by C-H center dot center dot center dot O interactions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H center dot center dot center dot H (37.2%), C center dot center dot center dot H (30.7%) and O center dot center dot center dot H (24.9%) interactions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6-311 G(d,p) level is compared to the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.