• 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

  • Pages
    19
  • From page
    1
  • To page
    19
  • 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
  • Serial Year
    2019
  • Record number

    2625225