5-[(E)-2-Bromobenzylidene]-8-(2-bromophenyl)-2-hydroxy-10-methyl-3,10-diazahexacyclo[10.7.1.13,7.02,11.07,11.016,20]henicosa-1(20),12,14,16,18-pentaen-6-one

In the title compound, C33H26Br2N2O2, the piperidine group adopts an envelope conformation while the two pyrrolidine groups adopt half-chair and envelope conformations. The dihydroacenaphthylene group is almost planar, with a maximum deviation of 0.105 (1) Å. The dihedral angle between the two bromophenyl rings is 60.19 (8)°. An intramolecular O—H⋯N interaction is observed, generating an S(5) ring motif. The crystal structure is stabilized by intermolecular C—H⋯O interactions. Short Br⋯Br [3.461 (1) Å] and Br⋯C [3.322 (2) Å] intermolecular contacts are observed, as well as π–π interactions [centroid–centroid distance = 3.793 (1) Å].

In the title compound, C 33 H 26 Br 2 N 2 O 2 , the piperidine group adopts an envelope conformation while the two pyrrolidine groups adopt half-chair and envelope conformations. The dihydroacenaphthylene group is almost planar, with a maximum deviation of 0.105 (1) Å . The dihedral angle between the two bromophenyl rings is 60.19 (8) . An intramolecular O-HÁ Á ÁN interaction is observed, generating an S(5) ring motif. The crystal structure is stabilized by intermolecular C-HÁ Á ÁO interactions. Short BrÁ Á ÁBr

Refinement
The H atom attached to O2 was located in a difference map and refined isotropically [O-H = 0.75 (3) Å]. The remaining H atoms were positioned geometrically and refined using a riding model [C-H = 0.93 Å for Csp 2 , 0.96 Å for methyl C, supplementary materials sup-2 0.97 Å for methylene C and 0.98 Å for methine C]; U iso (H) = xU eq (C), where x = 1.5 for methyl H and 1.2 for all other H atoms. A rotating model was used for the methyl group. Fig. 1. The molecular structure, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 > 2sigma(F 2 ) is used only for calculating R-factors(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.