5-(4-Fluorobenzylidene)-4′-(4-fluorophenyl)-1,1′-dimethyldispiro[piperidine-3,3′-pyrrolidine-2′,3′′-indoline]-4,2′′-dione

The asymmetric unit of the title compound, C30H27F2N3O2, contains two independent molecules. The pyrrolidine five-membered ring assumes an envelope conformation (with the CH2 atom at the flap) in one molecule and a twisted conformation in the other one. In both independent molecules, the 4-piperidinone rings adopt a similar twisted chair conformation. In the crystal, the two independent molecules form an R 2 2(8) dimer through a pair of N—H⋯O hydrogen bonds; the R 2 2(8) dimers are connected via weak C—H⋯O hydrogen bonds, leading to a chain extending along the c axis.

The asymmetric unit of the title compound, C 30 H 27 F 2 N 3 O 2 , contains two independent molecules. The pyrrolidine fivemembered ring assumes an envelope conformation (with the CH 2 atom at the flap) in one molecule and a twisted conformation in the other one. In both independent molecules, the 4-piperidinone rings adopt a similar twisted chair conformation. In the crystal, the two independent molecules form an R 2 2 (8) dimer through a pair of N-HÁ Á ÁO hydrogen bonds; the R 2 2 (8) dimers are connected via weak C-HÁ Á ÁO hydrogen bonds, leading to a chain extending along the c axis.
Piperidin-4-ones are reported to possess analgesic, anti-inflammatory, anti-cancer, anti-microbial activities and herbicidal properties (Mobio et al., 1989;Dimmock et al., 2001;Perumal et al., 2001) and act as potential inhibitors of human placental aromatase in vitro (Baroudi et al., 1996). Similarly, the pyrrolidine compounds have been reported to be potential inhibitors of diabetes, cancer and infection causing pathogens (Watson et al., 2001). The present structural characterization using single-crystal X-ray intensity data was carried out with a view to understand drug design mechanisms and explore the possibility of discovery of a 'unidrug′ with 'multiactivity′ properties.
The title compound, C 33 H 27 N 3 O 2 F 2 (I), crystallizes in the space group Cc with two molecules in the asymmetric unit.

Figure 1
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.  Overlay diagram of the two molecules A and B in the asymmetric unit showing differences in their conformation.   The packing of (I), viewed down the c axis. Non-participating rings, methyl groups and F atoms are omitted for clarity.

Data collection
Bruker Kappa APEXII diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω and φ scan Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T min = 0.98, T max = 0.99 32062 measured reflections 7610 independent reflections 5922 reflections with I > 2σ(I) Special details 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.

sup-5
Acta Cryst. (2012). E68, o2839-o2840 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 > σ(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.