Crystal structure of (3E)-5-nitro-3-(2-phenylhydrazinylidene)-1H-indol-2(3H)-one
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 presen...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2017 |
| País: | Brasil |
| Institución: | Universidade Estadual Paulista (UNESP) |
| Repositorio: | Repositório Institucional da UNESP |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.unesp.br:11449/169428 |
| Acceso en línea: | http://dx.doi.org/10.1107/S2056989016020375 http://hdl.handle.net/11449/169428 |
| Access Level: | acceso abierto |
| Palabra clave: | crystal structure Hirshfeld surface calculation in silico evaluation isatin-hydrazone derivative two-dimensional hydrogen-bonded network |
| Sumario: | 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. |
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