Crystal structure of 2-{[(E)-(4-anilinophenyl)iminiumyl]methyl}-5-(diethylamino)phenolate

Abstract

The title compound, C23H25N3O, crystallized with one single molecule in the asymmetric unit and is present in the zwitterionic form. There is an intramolecular N—H...O hydrogen bond in the molecule with the phenol ring being inclined to the central benzene ring by 20.67 (14)°. The terminal aminophenyl ring forms a dihedral angle of 54.21 (14)° with the central benzene ring. The two outer aromatic rings are inclined to one another by 74.54 (14)°. In the crystal, the molecules are connected by N—H...O hydrogen bonds, with adjacent molecules related by a 21 screw axis, generating –A–B–A–B– zigzag chains extending along [010]. The chains are linked via C—H...π and π–π interactions [with a centroid–centroid distance of 3.444 (3) Å] between the benzene ring and the imino group of symmetry-related molecules, forming slabs lying parallel to (100).

Keywords

• crystal structure
• zwitterion
• N-phenyl-p-phenylenediamine
• DPIM
• Schiff base
• hydrogen bonding