Crystal structure, Hirshfeld surface analysis and DFT study of (5E,5′E,6Z,6′Z)-6,6′-[ethane-1,2-diylbis(azanylylidene)]bis{5-[2-(4-fluorophenyl)hydrazono]-3,3-dimethylcyclohexanone} 2.5-hydrate

Abstract

The title compound, C30H34F2N6O2·2.5H2O, was obtained by condensation of 2-[2-(4-fluorophenyl)hydrazono]-5,5-dimethylcyclohexan-1,3-dione with ethylenediamine in ethanol and crystallized as a 1:2.5 hydrate in space group C2/c. The two independent molecules, with approximate crystallographic C2 symmetries, have different conformations and packing environments, are stabilized by intramolecular N—H...N hydrogen bonds and linked by O—H...O hydrogen bonds involving the water molecules. A Hirshfeld surface analysis showed that H...H contacts make by far the largest (48–50%) contribution to the crystal packing. From DFT calculations, the LUMO–HOMO energy gap of the molecule is 0.827 eV.

Keywords

• crystal structure
• condensation
• crystal packing
• density functional theory
• hirshfeld surface analysis
• hydrogen bonding