Zwitterionic (E)-1-[(4-nitrophenyl)iminiomethyl]naphthalen-2-olate

Abstract

The title compound, C17H12N2O3, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-nitrobenzenamine. These condense to form the Schiff base, which crystallizes in the zwitterionic form. In the structure, the keto–amino tautomer has a fairly short intramolecular N—H...O hydrogen bond between the 2-naphthalenone and amino groups, with electron delocalization. The molecule is essentially planar, with a dihedral angle of 1.96 (3)° between the ring systems. In the crystal, the molecules are linked via intermolecular C—H...O hydrogen bonds, forming a layer parallel to (101).