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

Autor(es)

Velasques, Jecika Maciel ; Gervini, Vanessa Carratu ; Bortoluzzi, Adailton Joao ; de Farias, Renan Lira ; de Oliveira, Adriano Bof

• Tipo de documento: Artigo Científico
• Fonte: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS; v. 73, p. 10-pg., 2017-02-01.

Resumo

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 angstrom for the mean plane through all non-H atoms). An intramolecular N-H center dot center dot center dot O hydrogen bond is present, forming a ring of graph-set motif S(6). In the crystal, molecules are linked by N-H center dot center dot center dot O and C-H center dot center dot center dot 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 center dot center dot center dot Cg interactions and indicates that the most important contributions for the crystal structure are O center dot center dot center dot H (28.5%) and H center dot center dot center dot 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 center dot center dot center dot O(ASP29), N-H center dot center dot center dot O(ILE96) and Cg center dot center dot center dot Cg(PHE33) interactions. (AU)

• Processo FAPESP: 15/12098-0 - Dinitrosilos de ferro contendo tióis e/ou tiossemicarbazonas: síntese, caracterização e avaliação de atividade contra câncer.
• Beneficiário: José Clayston Melo Pereira
• Modalidade de apoio: Auxílio à Pesquisa - Regular