title: Crystal structure of (3E)-5-nitro-3-(2-phenyl-hydrazinyl-idene)-1H-indol-2(3H)-one.
abstract: The reaction between 5-nitro-isatin and phenyl-hydrazine in acidic ethanol yields the title compound, C14H10N4O3, whose mol-ecular structure deviates slightly from a planar geometry (r.m.s. deviation = 0.065 Å for the mean plane through all non-H atoms). An intra-molecular N-H⋯O hydrogen bond is present, forming a ring of graph-set motifS(6). In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen-bonding inter-actions 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 mol-ecules are stacked along [100] through C=O⋯Cginter-actions and indicates that the most important contributions for the crystal structure are O⋯H (28.5%) and H⋯H (26.7%) inter-actions. Anin silicoevaluation of the title compound with the DHFR enzyme (di-hydro-folate 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) inter-actions.
authors.affiliation: Universidade Federal do Rio Grande (FURG), Escola de Química e Alimentos, Rio Grande, Brazil.
authors.forename: Jecika Maciel
authors.initials: JM
authors.lastname: Velasques
authors.affiliation: Universidade Federal do Rio Grande (FURG), Escola de Química e Alimentos, Rio Grande, Brazil.
authors.forename: Vanessa Carratu
authors.initials: VC
authors.lastname: Gervini
authors.affiliation: Universidade Federal de Santa Catarina (UFSC), Departamento de Química, Florianópolis, Brazil.
authors.forename: Adaílton João
authors.initials: AJ
authors.lastname: Bortoluzzi
authors.affiliation: Universidade Estadual Paulista (UNESP), Instituto de Química, Araraquara, Brazil.
authors.forename: Renan Lira
authors.initials: RL
authors.lastname: de Farias
authors.affiliation: Universidade Federal de Sergipe (UFS), Departamento de Química, São Cristóvão, Brazil.
authors.forename: Adriano Bof
authors.initials: AB
authors.lastname: de Oliveira
keywords: Hirshfeld surface calculation; crystal structure; in silico evaluation; isatin–hydrazone derivative; two-dimensional hydrogen-bonded network