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 isE. 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)°, respectively. In the crystal, molecules are linked by pairs of O—H...N hydrogen bonds, forming inversion dimers. The dimers are connected to neighbouring dimers by N—H...O hydrogen bonds and C—H...π interactions, forming layers parallel to thebcplane. The layers are linked by offset π–π interactions [intercentroid distance = 3.779 (2) Å], forming a three-dimensional supramolecular structure. Quantum chemical calculations of the molecule are in good agreement with the solid-state structure.