Author/Authors :
Velasques, Jecika Maciel Universidade Federal do Rio Grande (FURG) - Escola de Química e Alimentos, Rio Grande, Brazil , Carratu Gervini, Vanessa Universidade Federal do Rio Grande (FURG) - Escola de Química e Alimentos, Rio Grande, Brazil , Bortoluzzi, Adaílton João Universidade Federal de Santa Catarina (UFSC) - Departamento de Química, Florianópolis, Brazil , Farias, Renan Lira de Universidade Estadual Paulista (UNESP) - Instituto de Química, Araraquara, Brazil , Oliveira, Adriano Bof de Universidade Federal de Sergipe (UFS) - Departamento de Química, São Cristóvão, Brazil
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 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 R22(8), R22(26) and R44(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.
Keywords :
crystal structure , in silico evaluation , two-dimensional hydrogen-bonded network , Hirshfeld surface calculation
