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 degrees out of a coplanarity, while the other phenyl group is almost orthogonal to the first (89 degrees). The only observed classical hydrogen bonding is an intramolecular N-H center dot center dot center dot O. The supramolecular structure was analyzed employing the Hirshfeld surface and that is organized through C-H center dot center dot center dot O hydrogen bond and C-H center dot center dot center dot pi, polar-pi, and pi-stacking. An interaction involving NO2 center dot center dot center dot NO2 was also observed.