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Title: Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 3-butyl-2,6-bis(4-fluorophenyl)piperidin-4-one
Authors: K. Anitha
S. Sivakumar
R. Arulraj 
K. Rajkumar
Manpreet Kaur
Jerry P. Jasinski
Keywords: Piperidin-4-one
Crystal structure
Hirshfeld surface
Issue Date: 2-Apr-2020
Publisher: International Union of Crystallography
Citation: K. Anitha, S. Sivakumar, R. Arulraj, K. Rajkumar, Manpreet Kaur, Jerry P. Jasinski (2020-04-02). Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 3-butyl-2,6-bis(4-fluorophenyl)piperidin-4-one. Acta Crystallographica Section E: Crystallographic Communications 76 (5) : 651-655. ScholarBank@NUS Repository.
Rights: CC0 1.0 Universal
Abstract: 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.
Source Title: Acta Crystallographica Section E: Crystallographic Communications
ISSN: 20569890
DOI: 10.1107/S2056989020004636
Rights: CC0 1.0 Universal
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