Crystal structure of methyl 2-[2,4-bis(4-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-ylidene]hydrazinecarboxylate

Abstract

In the title compound, C22H23F2N3O2, the bicyclic ring system exists in a twin-chair conformation with an equatorial disposition of the 4-fluorophenyl groups on the heterocycle. These aromatic rings are inclined to one another by 19.4 (1)°. In the crystal, molecules are linked by pairs of N—H...O and C—H...O hydrogen bonds into inversion dimers, incorporating R12(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.

Keywords

• crystal structure
• 3-azabicyclo[3.3.1]nonane
• hydrazinecarboxylate
• twin-chair conformation