Crystal structure and DFT study of (E)-4-[({4[(pyridin-2-ylmethylidene)amino]phenyl}amino)-methyl] phenol

Abstract

In the title Schiff base compound, C19H17N3O, the configuration about the C=N bond is E. The molecule is non-planar, with the phenolic and pyridine rings being inclined to the central benzene ring by 56.59 (4) and 15.13 (14)degrees, respectively. In the crystal, molecules are linked by pairs of O-H center dot center dot center dot N hydrogen bonds, forming inversion dimers. The dimers are connected to neighbouring dimers by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi interactions, forming layers parallel to the bc plane. The layers are linked by offset pi-pi interactions [intercentroid distance = 3.779 (2) angstrom], forming a three-dimensional supramolecular structure. Quantum chemical calculations of the molecule are in good agreement with the solid-state structure.