(E)-1-[(2-Amino-5-nitrophenyl)iminiomethyl]naphthalen-2-olate

Abstract

The title Schiff base compound, C17H13N3O3, crystallizes in a zwitterionic form and exists in a trans configuration about the C=N bond. The mol­ecule is slightly twisted, the dihedral angle between the benzene ring and naphthalene ring system being 10.80 (9)°. The nitro group is twisted relative to the plane of the benzene ring [dihedral angle = 8.88 (12)°]. Bifurcated intra­molecular N—H⋯N and N—H⋯O hydrogen bonds formed between iminium groups and amine N atoms and naphthalen-2-olate O atoms generate S(5) and S(6) ring motifs, respectively. In the crystal, neighbouring zwitterions are linked through weak C—H⋯O inter­actions, giving rise to screw chains along [010]. Mol­ecules in these chains are linked to those of an adjacent chains through N—H⋯O hydrogen bonds and weak C—H⋯O inter­actions, forming sheets parallel to the ac plane. O⋯C [2.895 (3) Å] short contacts and π–π inter­actions [centroid–centroid distance = 3.8249 (19) Å] are also observed.