Crystal structure and Hirshfeld surface analysis of methyl 4-[(E)-2-(5-bromo-2-methoxybenzylidene)hydrazinyl]-3-nitrobenzoate

The title compound, C16H14BrN3O5, is a novel halogen (Br) substituted hydrazine derivative. The hydrazine derivatives were the group of compounds with the general structure, R1R2C=NNH2 (Uppal et al., 2011), with the central RC=NNH2 moiety bridging two different groups on both sides. An all-trans configuration of the backbone (RC=NNH2) results in an extended mol­ecular conformation. The dihedral angle between the 5-bromo-2-meth­oxy­phenyl ring and the nitrophenyl ring is 4.4 (3)°. Intra­molecular N—H⋯O inter­actions form S(6) graph-set motifs, while C—H⋯O and C—H⋯N inter­actions form S(5) graph-set motifs. Symmetry-related mol­ecules are linked by C—H⋯O inter­molecular inter­actions forming an R21(10) graph-set motif. There are nearly face-to-face directional specific π–π stacking inter­actions between the centroids of the nitrophenyl ring and the benzene ring of the 5-bromo-2-meth­oxy group [centroid–centroid distance = 3.6121 (5) A and slippage = 1.115 A], which also contributes to the mol­ecular packing. The Hirshfeld surface analysis was performed in order to visualize, explore and qu­antify the inter­molecular inter­actions in the crystal lattice of the title compound.