Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 3-butyl-2,6-bis(4-fluorophenyl)piperidin-4-one

Abstract

The title compound, C₂₁H₂₃F₂NO, consists of two fluoro-phenyl groups and one butyl group equatorially oriented on a piperidine ring, which adopts a chair conformation. The dihedral angle between the mean planes of the phenyl rings is 72.1 (1)°. In the crystal, N-H⋯O and weak C-H⋯F inter-actions, which form <i>R</i> ² ₂[14] motifs, link the mol-ecules into infinite <i>C</i>(6) chains propagating along [001]. A weak C-H⋯π inter-action is also observed. A Hirshfeld surface analysis of the crystal structure indicates that the most significant contributions to the crystal packing are from H⋯H (53.3%), H⋯C/C⋯H (19.1%), H⋯F/F⋯H (15.7%) and H⋯O/O⋯H (7.7%) contacts. Density functional theory geometry-optimized calculations were compared to the experimentally determined structure in the solid state and used to determine the HOMO-LUMO energy gap and compare it to the UV-vis experimental spectrum.