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

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.