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Synthesis, crystal structure, DFT calculations and Hirshfeld surface analysis of 3-butyl-2,6-bis-(4-fluoro-phen-yl)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 R 2 2[14] motifs, link the mol-ecules into infinite C(6) chains propagating along [001]. A weak C-H?? 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.

SUBMITTER: Anitha K 

PROVIDER: S-EPMC7199252 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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

Anitha K K   Sivakumar S S   Arulraj R R   Rajkumar K K   Kaur Manpreet M   Jasinski Jerry P JP  

Acta crystallographica. Section E, Crystallographic communications 20200409 Pt 5

The title compound, C<sub>21</sub>H<sub>23</sub>F<sub>2</sub>NO, 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> <sup>2</sup> <sub>2</sub>[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  ...[more]

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