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

The title compound, C21H23F2NO, consists of two fluorophenyl 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 interactions, which form R22[14] motifs, link the molecules into infinite C(6) chains propagating along [001]. A weak C—H...π interaction 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.

Abstract licence: CC BY

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