Crystal Structure and DFT Study of (E)-4-[({4-[(pyri-din-2-yl-methyl-idene)amino]-phen-yl}amino)-meth-yl]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)°, 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 the bc plane. The layers are linked by offset π-π interactions [intercentroid distance = 3.779 (2) A], forming a three-dimensional supramolecular structure. Quantum chemical calculations of the molecule are in good agreement with the solid-state structure. © 2018 International Union of Crystallography. All rights reserved.