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

• Autor(a) principal: Ligiéro,Carolina B. P.
• Data de Publicação: 2021
• Outros Autores: Monte,Pamella M., Silva,Tiago L. da, Barros,José C.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000200429
• topic: crystal structure; 2,4-dinitrophenylhydrazine; 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 15º 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 bond and C-H···π, polar-π, and π-stacking. An interaction involving NO2···NO2 was also observed.