Synthesis, molecular and electronic properties, and crystal structure of two novel potent perfluorophenylhydrazone derivatives, 1-((5-nitrothiophen-2-yl)methylene)-2-(perfluorophenyl) hydrazine, and 1-((5-nitrofuran-2-yl)methylene)-2-(perfluorophenyl) hydrazine

Two novel potent perfluorophenylhydrazone derivatives, 1-((5-nitrothiophen-2-yl)methylene)-2-(per- fluorophenyl)hydrazine, (I), and 1-((5-nitrofuran-2-yl)methylene)-2-(perfluorophenyl) hydrazine, (II), are introduced, with suggested improvement by further design. Their multitarget structures and features have been combined to create potential AD therapeutics. Crystals (I) and (II) are molecules with two rings and a hydrazone part at the centre of the molecule. They were synthesised and characterised using elemental and spectroscopic (¹H-NMR) analyses and their crystal structures were determined using the single-crystal X-ray diffraction method. The structures crystallise in the monoclinic space group with Z = 2 and Z = 4 molecules per unit cell. Compound (I) crystallises as a dimer in the non-centrosymmetric space group, while compound (II) crystallises as a racemate in the centrosymmetric space group. The “absolute configuration and conformation for bond values” were not derived from anomalous dispersion (rmad). The crystal structures reveal diverse non-covalent interactions such as intra- and inter-hydrogen bonding, π-ring — π-ring, C—H — π-ring interactions. The expected stereochemistry of hydrazone atoms C7, N2, and N1 was confirmed for compounds (I) and (II). Both molecules possess a “boat conformation” resembling a 6-membered ring. Results of the single crystal studies were reproduced using the Hirshfeld surface analysis, Gaussian software, and QTAIM contour mapping.