Abstract
•X-RAY cystal structure of methyl (Z)-4-((4-((4-bromobenzyl)selanyl)phenyl)amino)-4-oxobut-2-enoate (4).•DFT calculations of (4).•Hirshfeld surface analysis of (4).
The titled organoselenium compound, C18H16BrNO3Se methyl (Z)-4-((4-((4-bromobenzyl)selanyl)phenyl)amino)-4-oxobut-2-enoate (4), was prepared in a three-step synthetic procedure starting from 4,4′-diselanediyldianiline (1). The cytotoxic, antioxidant, and anti-apoptotic properties of the synthesized compounds were evaluated in oligodendrocytes. The crystal structure of 4 shows an orthorhombic system Pbca space group. The two phenyl rings are twisted to each other by 66.70 (15)⁰. The crystal cohesion is established by strong N-H…O hydrogen bonds, N…Br, N….O interactions, and by week aromatic π-π stacking interactions. Hirshfeld surface and the corresponding fingerprint plots of 4 quantify the interactions within the structure. The highest value of the enrichment ratio was calculated, and the Br…N (5.17%) followed by N…O (4%) have a high tendency to form contacts in the crystal. Density functional theory (DFT) optimized structure in the gaseous phase at B3LYP/6-311++G(d,p) level has been compared with the experimentally defined molecular structure. Furthermore, frontier molecular orbital and molecular electrostatic Potential mapping studies have been carried out.