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

Wang, Y.; Lin, Y.-Y.

doi:10.1107/S1600536811054420

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 (C-C) = 0.005 Å
R = 0.069
wR = 0.128
Data-to-parameter ratio = 14.0
Details

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

Yi Wang ^a ^* and Yong-Yue Lin ^a

^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-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.

Related literature

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).

Experimental

Crystal data

C₁₅H₂₁NO₄S
M_r = 311.39
Monoclinic, P 2₁ /n
a = 11.583 (5) Å
b = 5.598 (2) Å
c = 24.009 (9) Å
= 102.905 (7)°
V = 1517.5 (10) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.947, T_max = 0.986
9795 measured reflections
2676 independent reflections
2431 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.128
S = 1.23
2676 reflections
191 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3BO4	0.84	2.08	2.804 (3)	145
O4-H4O3ⁱ	0.84	2.01	2.837 (3)	167
Symmetry code: (i) -x+1, -y+1, -z.

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 ).

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.
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.

organic compounds