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Volume 68 
Part 1 
Page o231  
January 2012  

Received 4 November 2011
Accepted 18 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.069
wR = 0.128
Data-to-parameter ratio = 14.0
Details
Open access

3-Cyclopropyl-1-(4-methylphenylsulfonyl)piperidine-3,5-diol

aCollege of Chemistry and Engineering, Yunnan Normal University, Kunming, People's Republic of China
Correspondence e-mail: sslwangyi@yahoo.cn

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-H...O hydrogen bond occurs. In the crystal, molecules form inversion dimers via pairs of O-H...O hydrogen bonds, generating cyclic R44(8) motifs, as noted previously in related diols.

Related literature

Azacyclohexanediol (piperidinediol) derivatives are widely found in natural products and are often incorporated into drugs, see: Nagahama et al. (2003[Nagahama, K., Yamato, M., Kato, S. & Takeuchi, K. (2003). J. Pharm. Sci. 93, 55-61.]); Fukushima et al. (2001[Fukushima, Y., Otsuka, H. & Ishikawa, M. (2001). Digestion, 64, 155-160.]). For related structures, see: Hidekazu et al. (2005[Hidekazu, O., Yukiko, M. & Hiroki, T. (2005). J. Org. Chem. 70, 5207-5214.]); Karin et al. (2006[Karin, L., Ann-Britt, L. F. & Jan-E, B. (2006). J. Org. Chem. 71, 8622-8625.]). Similar hydrogen bonding has been seen in related diols, see: Ferguson et al. (1993[Ferguson, G., Gallagher, J. F., Glidewell, C. & Zakaria, C. M. (1993). Acta Cryst. C49, 967-971.]).

[Scheme 1]

Experimental

Crystal data
  • C15H21NO4S

  • Mr = 311.39

  • Monoclinic, P 21 /n

  • a = 11.583 (5) Å

  • b = 5.598 (2) Å

  • c = 24.009 (9) Å

  • [beta] = 102.905 (7)°

  • V = 1517.5 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 173 K

  • 0.24 × 0.11 × 0.06 mm

Data collection
  • Rigaku MM007-HF CCD (Saturn 724+) diffractometer

  • Absorption correction: numerical (CrystalClear; Rigaku, 2002[Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.947, Tmax = 0.986

  • 9795 measured reflections

  • 2676 independent reflections

  • 2431 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.128

  • S = 1.23

  • 2676 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3B...O4 0.84 2.08 2.804 (3) 145
O4-H4...O3i 0.84 2.01 2.837 (3) 167
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2064 ).


Acknowledgements

The authors thank the China Postdoctoral Science Foundation (grant No. 20090460146) and Yunnan Normal University for financial support.

References

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.  [CrossRef] [details]
Fukushima, Y., Otsuka, H. & Ishikawa, M. (2001). Digestion, 64, 155-160.  [PubMed] [ChemPort]
Hidekazu, O., Yukiko, M. & Hiroki, T. (2005). J. Org. Chem. 70, 5207-5214.  [PubMed]
Karin, L., Ann-Britt, L. F. & Jan-E, B. (2006). J. Org. Chem. 71, 8622-8625.  [PubMed]
Nagahama, K., Yamato, M., Kato, S. & Takeuchi, K. (2003). J. Pharm. Sci. 93, 55-61.  [ChemPort]
Rigaku (2002). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o231  [ doi:10.1107/S1600536811054420 ]

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