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 = 0.065 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 motifS(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 motifR22(8),R22(26) andR44(32) are observed. Additionally, a Hirshfeld surface analysis suggests that the molecules are stacked along [100] through C=O...Cginteractions and indicates that the most important contributions for the crystal structure are O...H (28.5%) and H...H (26.7%) interactions. Anin silicoevaluation 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) andCg...Cg(PHE33) interactions.