Received 4 November 2011
In the title compound, C15H21NO4S, both hydroxy groups on the piperidine ring are located in axial positions, whereas the tosyl group and the cyclopropane ring are in equatorial positions. An intramolecular O-HO hydrogen bond occurs. In the crystal, molecules form inversion dimers via pairs of O-HO hydrogen bonds, generating cyclic R44(8) motifs, as noted previously in related diols.
Azacyclohexanediol (piperidinediol) derivatives are widely found in natural products and are often incorporated into drugs, see: Nagahama et al. (2003); Fukushima et al. (2001). For related structures, see: Hidekazu et al. (2005); Karin et al. (2006). Similar hydrogen bonding has been seen in related diols, see: Ferguson et al. (1993).
Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2064 ).
The authors thank the China Postdoctoral Science Foundation (grant No. 20090460146) and Yunnan Normal University for financial support.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Ferguson, G., Gallagher, J. F., Glidewell, C. & Zakaria, C. M. (1993). Acta Cryst. C49, 967-971.
Fukushima, Y., Otsuka, H. & Ishikawa, M. (2001). Digestion, 64, 155-160.
Hidekazu, O., Yukiko, M. & Hiroki, T. (2005). J. Org. Chem. 70, 5207-5214.
Karin, L., Ann-Britt, L. F. & Jan-E, B. (2006). J. Org. Chem. 71, 8622-8625.
Nagahama, K., Yamato, M., Kato, S. & Takeuchi, K. (2003). J. Pharm. Sci. 93, 55-61.
Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.