Crystal Structure and Hirshfeld Surface Analysis of 1,4-Pentadien-3-one, (1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone

The compound 1,4-pentadien-3-one,(1E,4E)-1,5-diphenyl-2-(2,4-dinitrophenyl)hydrazone presents the molecular formula C23H18N4O4 and was prepared in an undergraduate laboratory. The hydrazone was synthesized from the condensation between dibenzalacetone and 2,4-dinitrophenylhydrazine (DNPH) and crystallized employing water/acetone liquid-liquid diffusion. The structure presents three aromatic rings connected by an unsaturated Y-shaped system. Dinitro substituted and one of the other aromatic rings are 15 º out of a coplanarity, while the other phenyl group is almost orthogonal to the first (89º). The only observed classical hydrogen bonding is an intramolecular N-H···O. The supramolecular structure was analyzed employing the Hirshfeld surface and that is organized through C-H···O hydrogen bo nd and C-H··· π , polar- π , and π -stacking. An interaction involving NO2 ···NO2 was also observed.
Source: Journal of the Brazilian Chemical Society - Category: Chemistry Source Type: research