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In the title compound, C(38)H(28)F(2)N(2)O(2), the piperidine ring adopts a chair conformation and the pyrrolidine ring adopts an envelope conformation with the spiro C atom as the flap atom. The naphthalene ring system makes dihedral angles of 39.89 (8), 35.33 (8) and 46.45 (8)° with the two fluoro-substituted benzene rings and the phenyl ring, respectively, while the dihedral angle between the two fluoro-substituted benzene rings is 75.21 (10)°. An intra-molecular O-H⋯N hydrogen bond generates an S(5) ring. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming supra-molecular chains propagating along the c-axis direction. Weak C-H⋯π inter-actions further consolidate the structure.

acta crystallographica. section e

5-[(E)-4-Fluorobenzylidene]-8-(4-fluorophenyl)-2-hydroxy-9-phenyl-3,10-diazahexacyclo[10.7.1.13,7.02,11.07,11.016,20]henicosa-1(20),12,14,16,18-pentaen-6-one