Received 4 November 2011
The crystal of the title compound, C21H23NO2, was chosen from a conglomerate formed by a racemic mixture. An intramolecular hydrogen bond is formed between hydroxy group and heterocyclic N atom of the azabicyclo[3.2.1]octan-3-one system. The crystal structure is stabilized by C-HO interactions between aliphatic C-H groups and the carbonyl O atom. For the title chiral crystal, the highly redundant and accurate diffraction data set collected with low energy copper radiation gave a Flack parameter of 0.12 (18) for anomalous scattering effects originating from O atoms.
For recent background literature on the chemistry of related tropane-derived aldols and their applications, including stereoselective syntheses of bioactive alkaloids, see: Lazny et al. (2011); Sienkiewicz et al. (2009) and references cited therein. For stereoselective syntheses of related nortropinone aldols, see: Lazny et al. (2001); Lazny & Nodzewska (2003). For a representative review of the biological activity of tropane derivatives, see: Singh (2000).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2429 ).
This work was supported in part by the University of Bialystok (BST-125), the Polish Ministry of Science and Higher Education (grant No. N N204 546939), the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research, and with Federal funds from the National Cancer Institute, National Institutes of Health, under contract HHSN2612008000001E.
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
DeLano, W. L. (2002). The pyMOL Molecular Graphics System. DeLano Scientific, San Carlos, CA, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Lazny, R. & Nodzewska, A. (2003). Tetrahedron Lett. 44, 2441-2444.
Lazny, R., Nodzewska, A. & Tomczuk, I. (2011). Tetrahedron Lett. 52, 5680-5683.
Lazny, R., Sienkiewicz, M. & Bräse, S. (2001). Tetrahedron, 57, 5825-5832.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sienkiewicz, M., Wilkaniec, U. & Lazny, R. (2009). Tetrahedron Lett. 50, 7196-7198.
Singh, S. (2000). Chem. Rev. 100, 925-1024.