Crystal structure and Hirshfeld surface analysis of 1-[(E)-2-(3-nitro­phen­yl)diazen-1-yl]naphthalen-2-ol

The title compound, C(16)H(11)N(3)O(3), belongs to the family of azo dyes. In the light of a single-crystal X-ray study, it is evident that of the tautomeric forms (azo–hydrazone), the hydrazone form is the predominant form in the solid state, namely, (1E)-1-[2-(3-nitro­phen­yl)hydrazin-1-yl­idene]-1,2-di­hydro­naphthalen-2-one. The naphthol and benzene fragments attached to the –N=N– moiety adopt the s-trans conformation. Furthermore, the mol­ecules are nearly coplanar, subtending a dihedral angle of 2.63 (5)°. An intra­molecular N—H⋯O hydrogen bond occurs. There are only two types of inter­molecular inter­actions in the crystal structure: strong hydrogen-bonding C—H⋯O inter­actions and π–π stacking inter­actions. The importance of C—H⋯O inter­actions in the mol­ecular packing is reflected by the relatively high contributions (28.5%) made by O⋯H/H⋯O contacts to the Hirshfeld surface.