(E)-1-(2,6-Di­chloro­phen­yl)-2-(3-nitro­benzyl­idene)hydrazine: crystal structure and Hirshfeld surface analysis

The stabilized conformation of the title compound, C(13)H(9)Cl(2)N(3)O(2), is similar to that of the isomeric compound (E)-1-(2,6-di­chloro­phen­yl)-2-(2-nitro­benzyl­idene)hydrazine. The 2,6-di­chloro­phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 26.25 (16)°. In the crystal, face-to-face π-π stacking inter­actions along the a-axis direction occur between the centroids of the 2,6-di­chloro­phenyl ring and the nitro-substituted benzene ring. The mol­ecules are further linked by C—H⋯O contacts and N—H⋯O and C—H⋯Cl hydrogen bonds, forming pairs of hydrogen-bonded mol­ecular layers parallel to (100). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (22.1%), Cl⋯H/H⋯Cl (20.5%), O⋯H/H⋯O (19.7%), C⋯C (11.1%) and C⋯H/H⋯C (8.3%) inter­actions.