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

Abstract

The reaction between 5-nitroisatin and phenylhydrazine in acidic ethanol yields the title compound, C14H10N4O3, whose molecular structure deviates slightly from a planar geometry (r.m.s. deviation = 0.065Å 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 R2 2(8), R2 2(26) and R4 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.