11-[(E)-4-Bromobenzylidene]-8-(4-bromophenyl)-14-hydroxy-3,13-diazaheptacyclo[13.7.1.19,13.02,9.02,14.03,7.019,23]tetracosa-1(22),15,17,19(23),20-pentaen-10-one

In the title compound, C35H28Br2N2O2, the piperidone ring adopts a chair conformation and the five-membered ring of the pyrrolidine ring adopts an envelope conformation. The naphthalene ring system makes dihedral angles of 37.12 (8) and 50.62 (9)° with the terminal bromo-substituted benzene rings. The dihedral angle between the two bromo-substituted benzene rings is 72.54 (10)°. In the crystal, adjacent molecules are connected by a pair of intermolecular C—H⋯O hydrogen bonds, forming an inversion dimer. An intramolecular O—H⋯N hydrogen bond is also present.

In the title compound, C 35 H 28 Br 2 N 2 O 2 , the piperidone ring adopts a chair conformation and the five-membered ring of the pyrrolidine ring adopts an envelope conformation. The naphthalene ring system makes dihedral angles of 37.12 (8) and 50.62 (9) with the terminal bromo-substituted benzene rings. The dihedral angle between the two bromo-substituted benzene rings is 72.54 (10) . In the crystal, adjacent molecules are connected by a pair of intermolecular C-HÁ Á ÁO hydrogen bonds, forming an inversion dimer. An intramolecular O-HÁ Á ÁN hydrogen bond is also present.
The molecular structure of the title compound is shown in Fig rings. The dihedral angle between the two bromo-substituted benzene (C1-C6) and (C13-C18) rings is 72.54 (10)°.
In the crystal packing (Fig. 2), adjacent molecules are connected by intermolecular C20-H20A···O2 hydrogen bonds, forming dimers arranged in sheets parallel to the bc-plane. An intramolecular O-H···N hydrogen bond is also present.

Refinement
The hydroxyl H atom H1O2 was located from a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically [C-H = 0.93 or 0.97 Å] and were refined using a riding model, with U iso (H) = 1.2U eq (C). Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme (H atoms are omitted for clarity).

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.