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

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 75; no. Pt 11; pp. 1774 - 1782
• Main Authors: Gomes, Ligia R, Low, John Nicolson, Wardell, James L, de Souza, Marcus V N, da Costa, Cristiane F
• Format: Journal Article
• Language: English
• Published: England International Union of Crystallography 01-11-2019
• Subjects: crystal structure; epimeric mixture; hirshfeld surface analysis; pixel calculations; Research Communications; crystal structure; Hirshfeld surface analysis; PIXEL calculations; epimeric mixture
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989019013938

A 1:1 epimeric mixture of 3-[(4-nitro-benzyl-idene)amino]-2(
)-(4-nitro-phen-yl)-5(
)-(propan-2-yl)imidazolidin-4-one, C
H
N
O
, was isolated from a reaction mixture of 2(
)-amino-3-methyl-1-oxo-butane-hydrazine and 4-nitro-benz-alde-hyde in ethanol. The product was derived from an initial reaction of 2(
)-amino-3-methyl-1-oxo-butane-hydrazine at its hydrazine group to provide a 4-nitro-benzyl-idene derivative, followed by a cyclization reaction with another mol-ecule of 4-nitro-benzaldehyde 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(carbon-yl) and C-H⋯O(nitro) hydrogen bonds, as well as C-H⋯π, N-H⋯π and π-π inter-actions, are present. These combine to generate a three-dimensional array. Hirshfeld surface analysis and PIXEL calculations are also reported.