Crystal structure and DFT study of (E)-2,6-di-tert-butyl-4-{[2-(pyridin-2-yl)hydrazin-1-ylidene)methyl}phenol

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Faizi M. S. H., Haque A., Dege M., DEGE N., Malysheva M. L.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.73, pp.1449-1457, 2017 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 73
  • Publication Date: 2017
  • Doi Number: 10.1107/s2056989017011707
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.1449-1457
  • Keywords: crystal structure, hydrazine, 2-hydrazinopyridine, 3,5-di-tert-butyl-4-hydroxybenzaldehyde, hydrogen bonding, Schiff base, BIOLOGICAL-ACTIVITY
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The title compound, C20H27N3O, was synthesized by condensation reaction of 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 2-hydrazinylpyridine, and crystallizes in the centrosymmetric monoclinic space group C2/c. The conformation about the C=N bond is E. The dihedral angle between the rings is 18.1 (3)degrees. An intermolecular N-H center dot center dot center dot N hydrogen bond generates an R-2(2)(8) ring motif. In the crystal, N-H center dot center dot center dot N hydrogen bonds connect pairs of molecules, forming dimers. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state.