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

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YAĞCI N. K., Faizi M. S. H., Aydin A. S., DEGE N., Doğan O. E., Ağar E., ...Daha Fazla

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.76, ss.1075-1083, 2020 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1107/s2056989020007847
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.1075-1083
  • Anahtar Kelimeler: crystal structure, Schiff base, intramolecular hydrogen bonding, 2-hydroxy-5-methylbenzaldehyde, p-tolylamine, INTERMOLECULAR INTERACTIONS, QUANTITATIVE-ANALYSIS, PROTON-TRANSFER, STATE
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

In the title compound, C15H15NO, the configuration of the C=N bond of the Schiff base is E, and an intramolecular O-H center dot center dot center dot N hydrogen bond is observed, forming an intramolecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)degrees from the plane of the aniline ring. In the crystal, molecules are linked along the b axis by O-H center dot center dot center dot N and C-H center dot center dot center dot O hydrogen bonds, forming polymeric chains. 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 (56.9%) and H center dot center dot center dot C/C center dot center dot center dot H (31.2%) 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. The crystal studied was refined as an inversion twin.