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⋯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.
Highlights
Piperidin-4-one compounds have various biological properties and have applications as anti-viral, antitumor, and antihistaminic agents (El-Subbagh et al, 2000; Mobio et al, 1989; Katritzky & Fan, 1990; Arulraj et al, 2020). 2,6-Disubstituted piperidine-4-ones commonly adopt a chair conformation for the heterocyclic ring
As part of our studies in this area, we describe the synthesis and structure of the title compound, C21H23F2NO, (I), in order to establish the structural effects of the butyl and fluoro groups on the conformation
Supramolecular features N1—H1Á Á ÁO1 and weak C7—H7Á Á ÁF1 interactions are observed in the crystal of (I) (Table 1, Fig. 2), which form R22[14] graph-set ring motifs and infinite C(6) chains along [001]
Summary
Piperidin-4-one compounds have various biological properties and have applications as anti-viral, antitumor, and antihistaminic agents (El-Subbagh et al, 2000; Mobio et al, 1989; Katritzky & Fan, 1990; Arulraj et al, 2020). 2,6-Disubstituted piperidine-4-ones commonly adopt a chair conformation for the heterocyclic ring (see, for example, Rajkumar et al, 2018). Piperidin-4-one compounds have various biological properties and have applications as anti-viral, antitumor, and antihistaminic agents (El-Subbagh et al, 2000; Mobio et al, 1989; Katritzky & Fan, 1990; Arulraj et al, 2020). 2,6-Disubstituted piperidine-4-ones commonly adopt a chair conformation for the heterocyclic ring (see, for example, Rajkumar et al, 2018). On varying the substituents attached to the phenyl ring, the conformation of the ring may change (e.g. Ramachandran et al, 2007; Arulraj et al, 2020). The attached functional group on the crystalline compound is important to determine the activity of the compound in the area of drug discovery. As part of our studies in this area, we describe the synthesis and structure of the title compound, C21H23F2NO, (I), in order to establish the structural effects of the butyl and fluoro groups on the conformation. Symmetry codes: (i) x; Ày þ 12; z þ 12; (ii) x; Ày þ 12; z À 12; (iii) x À 1; Ày þ 12; z þ 12; (iv) Àx þ 1; y þ 12; Àz þ 32; (v) Àx þ 2; Ày þ 1; Àz þ 1
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