Title of article :
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
Author/Authors :
Gomes, Ligia R. REQUIMTE, Departamento de Química e Bioquímica - Faculdade de Ciências da Universidade do Porto, Portugal , Low, John Nicolson Department of Chemistry - University of Aberdeen , Scotland , Wardell , James L. Department of Chemistry - University of Aberdeen , Scotland , de Souza, Marcus V. N. Instituto de Tecnologia em Fármacos–Farmanguinhos - Fundaçâo Oswaldo Cruz, Brazil , da Costa, Cristiane F. Instituto de Tecnologia em Fármacos–Farmanguinhos - Fundaçâo Oswaldo Cruz, Brazil
Abstract :
A 1:1 epimeric mixture of 3-[(4-nitrobenzylidene)amino]-2(R,S)-(4-nitrophenyl)-5(S)-(propan-2-yl)imidazolidin-4-one, C19H19N5O5, 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.
Keywords :
crystal structure , Hirshfeld surface analysis , PIXEL calculations , epimeric mixture
Journal title :
Acta Crystallographica Section E: Crystallographic Communications