Crystal structure of (3E)-5-nitro-3-(2-phenyl­hydrazinyl­idene)-1H-indol-2(3H)-one

The reaction between 5-nitro­isatin and phenyl­hydrazine in acidic ethanol yields the title compound, C(14)H(10)N(4)O(3), whose mol­ecular structure deviates slightly from a planar geometry (r.m.s. deviation = 0.065 Å for the mean plane through all non-H atoms). An intra­molecular N—H⋯O hydrogen bond is present, forming a ring of graph-set motif S(6). In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen-bonding inter­actions into a two-dimensional network along (120), and rings of graph-set motif R (2) (2)(8), R (2) (2)(26) and R (4) (4)(32) are observed. Additionally, a Hirshfeld surface analysis suggests that the mol­ecules are stacked along [100] through C=O⋯Cg inter­actions and indicates that the most important contributions for the crystal structure are O⋯H (28.5%) and H⋯H (26.7%) inter­actions. An in silico evaluation of the title compound with the DHFR enzyme (di­hydro­folate reductase) was performed. The isatin–hydrazone derivative and the active site of the selected enzyme show N—H⋯O(ASP29), N—H⋯O(ILE96) and Cg⋯Cg(PHE33) inter­actions.