Received 13 August 2012
In the title compound, C25H26N2O3, the double bond connecting the aza-bicyclic and indole units has Z geometry. The compound was obtained as a racemate, and since the crystal is centrosymmetric it contains equal amounts of the S and R enantiomers. However, the structure is disordered such that the asymmetric unit contains both enantiomers in unequal amounts [refined occupancies 0.904 (2) and 0.096 (2)]. The dihedral angle between the benzene ring of the benzyl group and the mean plane of the indole ring is 76.07 (3) °. In the crystal, molecules are linked by O-HOcarbonyl hydrogen bonds into chains propagating in .
For background literature, see: Sekhar et al., (2003), Amudhan et al., (2010). For the biological activity of N-benzyl indole quinuclidinone, see: Sonar et al. (2007). For a similar crystal structure, see: Sonar et al., (2004).
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and local procedures.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5242 ).
This investigation was supported by NIH/National Cancer Institute grant PO1 CA140409.
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