Crystal structure and Hirshfeld surface analysis of 2,4,6,11-tetrakis(4-fluoropnenyl)-9-oxa-1,5-diazatricyclo[5.3.1.0(3.8)]undecane

The title compound, C32H26F4N2O, crystallizes in the monoclinic space group P2(1)/n with four molecules in the unit cell. The compound was prepared by the NaBH4 reduction of 4,8,9,10-tetrakis(4-fluorophenyl)-1,3-diazaadamantan-6-one in chloroform and ethanol as solvent. The piperidine rings exhibit chair and boat conformations, and all four fluorophenyl groups are oriented in the equatorial direction. The crystal structure features C-H center dot center dot center dot F hydrogen bonds, C-H center dot center dot center dot pi, N-H center dot center dot center dot pi and pi-pi interactions. Hirshfeld surface and two-dimensional fingerprint analysis show that van der Waals interactions constitute a major contribution to the intermolecular interactions, with H center dot center dot center dot H contacts accounting for 37.9% of the surface.