(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

Abstract

The title zwitterion, C18H16N2O, features an intramolecular N—H...O hydrogen bond. The dimethylbenzene ring is rotationally disordered about the N—C bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalene ring system is 6.06 (2)°. In the crystal, aromatic π–π stacking occurs [shortest centroid–centroid distance = 3.574 (3) Å] and C—H...O interactions are also observed.

Keywords

• crystal structure
• zwitterion
• azo dyes
• hydrogen bonding
• π–π stacking