Crystal structure and Hirshfeld surface analysis of (E)-2-[1-hydroxy-2-(pyridin-2-yl)ethyl]-4-[2-(4-methoxyphenyl)diazen-1-yl]phenol

Abstract

In the title compound, C20H19N3O3, the configuration about the azo N=N bond is E, and the central benzene ring is inclined to the pyridine ring by 31.43 (8)° and to the 4-methoxyphenyl ring by 4.73 (8)°. In the crystal, molecules are linked by pairs of O—H...N hydrogen bonds, forming inversion dimers with an R22(12) ring motif. The dimers are linked by O—H...O and C—H...O hydrogen bonds, forming layers parallel to the ac plane. There are C—H...π interactions present within the layers and between the layers, leading to the formation of a supramolecular framework. The layers are also linked by offset π–π interactions, with an interplanar distance of 3.416 (2) Å.

Keywords

• crystal structure
• azo compounds
• diazenyl
• pyridine
• hydrogen bonding
• C—H...π interactions
• offset π–π interactions
• supramolecular framework
• Hirshfeld surface analysis