Abstract
In the title compound, C22H23F2N3O2, the bicyclic ring system exists in a twin-chair conformation with an equatorial disposition of the 4-fluoro-phenyl groups on the heterocycle. These aromatic rings are inclined to one another by 19.4 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O and C-H⋯O hydrogen bonds into inversion dimers, incorporating R 1 (2)(7) and R 2 (2)(8) ring motifs; the same O atom accepts both hydrogen bonds. These dimers are further linked by a pair of C-H⋯F hydrogen bonds, enclosing R 2 (2)(28) ring motifs, forming supra-molecular chains along [010]. The NH group of the pyridine ring is not involved in hydrogen bonding, probably due to the steric hindrance of the fluoro-phenyl groups.
Highlights
C22H23F2N3O2, the bicyclic ring system exists in a twinchair conformation with an equatorial disposition of the 4-fluorophenyl groups on the heterocycle
Hydrogen bonds into inversion dimers, incorporating R21(7) and R22(8) ring motifs; the same O atom accepts both hydrogen bonds. These dimers are further linked by a pair of C—H F hydrogen bonds, enclosing R22(28) ring motifs, forming supramolecular chains along [010]
The NH group of the pyridine ring is not involved in hydrogen bonding, probably due to the steric hindrance of the fluorophenyl groups
Summary
Molecules containing the 3-azabicyclo[3.3.1]nonane nucleus are of great interest due to their presence in a wide range of naturally occurring diterpenoid/norditerpenoid alkaloids and their broad-spectrum biological activities, such as antimicrobial, analgesic, antagonistic, anti-inflammatory and local anesthetic hypotensive activity (Parthiban et al, 2009; Hardick et al, 1996; Jeyaraman & Avila, 1981). The synthesis of new molecules with the 3-azabicyclo[3.3.1]nonane nucleus and their stereochemical investigation are of interest in the field of medicinal chemistry. The stereochemistry of such molecules is a major criterium for their biological response. The present study was undertaken to examine the configuration and conformation of the synthesized title compound. Symmetry codes: (i) x þ 12; y þ 52; z; (ii) x þ 12; y þ 32; z
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