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Crystal structure, Hirshfeld surface analysis and PIXEL calculations of a 1:1 epimeric mixture of 3-[(4-nitro­benzyl­idene)amino]-2(R,S)-(4-nitro­phenyl)-5(S)-(propan-2-yl)imidazolidin-4-one

A 1:1 epimeric mixture of 3-[(4-nitro­benzyl­idene)amino]-2(R,S)-(4-nitro­phen­yl)-5(S)-(propan-2-yl)imidazolidin-4-one, C(19)H(19)N(5)O(5), was isolated from a reaction mixture of 2(S)-amino-3-methyl-1-oxo­butane­hydrazine and 4-nitro­benz­alde­hyde in ethanol. The product was derived from an initi...

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Detalles Bibliográficos
Autores principales: Gomes, Ligia R., Low, John Nicolson, Wardell, James L., de Souza, Marcus V. N., da Costa, Cristiane F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829720/
https://www.ncbi.nlm.nih.gov/pubmed/31709107
http://dx.doi.org/10.1107/S2056989019013938
Descripción
Sumario:A 1:1 epimeric mixture of 3-[(4-nitro­benzyl­idene)amino]-2(R,S)-(4-nitro­phen­yl)-5(S)-(propan-2-yl)imidazolidin-4-one, C(19)H(19)N(5)O(5), was isolated from a reaction mixture of 2(S)-amino-3-methyl-1-oxo­butane­hydrazine and 4-nitro­benz­alde­hyde in ethanol. The product was derived from an initial reaction of 2(S)-amino-3-methyl-1-oxo­butane­hydrazine at its hydrazine group to provide a 4-nitro­benzyl­idene derivative, followed by a cyclization reaction with another mol­ecule of 4-nitro­benzaldehyde to form the chiral five-membered imidazolidin-4-one ring. The formation of the five-membered imidazolidin-4-one ring occurred with retention of the configuration at the 5-position, but with racemization at the 2-position. In the crystal, N—H⋯O(nitro) hydrogen bonds, weak C—H⋯O(carbon­yl) and C—H⋯O(nitro) hydrogen bonds, as well as C—H⋯π, N—H⋯π and π–π inter­actions, are present. These combine to generate a three-dimensional array. Hirshfeld surface analysis and PIXEL calculations are also reported.