Abstract

The title compound, C32H26F4N2O, crystallizes in the monoclinic space group P21/n with four mol-ecules in the unit cell. The compound was prepared by the NaBH4 reduction of 4,8,9,10-tetra-kis-(4-fluoro-phen-yl)-1,3-di-aza-adamantan-6-one in chloro-form and ethanol as solvent. The piperidine rings exhibit chair and boat conformations, and all four fluoro-phenyl groups are oriented in the equatorial direction. The crystal structure features C-H⋯F hydrogen bonds, C-H⋯π, N-H⋯π and π-π inter-actions. Hirshfeld surface and two-dimensional fingerprint analysis show that van der Waals inter-actions constitute a major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 37.9% of the surface.

Highlights

  • The title compound, C32H26F4N2O, crystallizes in the monoclinic space group P21/n with four molecules in the unit cell

  • Hirshfeld surface and twodimensional fingerprint analysis show that van der Waals interactions constitute a major contribution to the intermolecular interactions, with HÁ Á ÁH contacts accounting for 37.9% of the surface

  • The title compound contains four fluorophenyl groups and the investigation looked for any weak interactions involving fluorine which are of current interest (Hathwar et al, 2014)

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Summary

Chemical context

Molecules containing a bispidine nucleus are of great interest due to their presence in a wide variety of naturally occurring alkaloids and various biologically active molecules (Jeyaraman & Avila, 1981). The biological activities of the molecule depend crucially on the stereochemistry and conformation of the compound, and studies on the stereochemistry of the molecules are interesting. The title compound contains four fluorophenyl groups and the investigation looked for any weak interactions involving fluorine which are of current interest (Hathwar et al, 2014). Das et al (2017) have recently discussed the role of halogens in stabilizing stacking patterns.

Structural commentary
Supramolecular features
Hirshfeld surface analysis
Database survey
Findings
Synthesis and crystallization
Full Text
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