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Volume 69 
Part 5 
Page o731  
May 2013  

Received 28 February 2013
Accepted 3 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.031
wR = 0.078
Data-to-parameter ratio = 11.3
Details
Open access

(1R,2S,5R)-(-)-Menthyl (S)-2-(methoxycarbonyl)benzenesulfinate

aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy,bICS, Université de Strasbourg, France, and cDipartimento di Ingegneria Industriale, University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
Correspondence e-mail: paolapaoli@unifi.it

In the title chiral sulfinic acid ester, C18H26O4S, the cyclohexane ring of the menthyl fragment adopts a chair conformation. The molecular shape is defined by the dihedral angle of 47.87 (8)° between the mean planes of the cyclohexane and benzene rings. In the crystal, molecules related by the screw axis are connected into chains along [010] by weak Car-H...O=S contacts.

Related literature

For the synthesis of the title compound, see: Klunder & Sharpless (1987[Klunder, J. M. & Sharpless, K. B. (1987). J. Org. Chem. 52, 2598-2602.]) and of chiral sulfoxides, see: Drabowicz et al. (1982[Drabowicz, J., Bujnicki, B. & Mikolajczyk, M. (1982). J. Org. Chem. 47, 3325-3327.]); Solladié et al. (1987[Solladié, G., Hutt, J. & Girardin, A. (1987). Synthesis, pp. 173-173.]). For applications of menthol in synthetic chemistry, see Oertling et al. (2007[Oertling, H., Reckziegel, A., Surburg, H. & Bertram, H.-J. (2007). Chem. Rev. 107, 2136-2164.]). For structural studies of analogous chiral sulfinic acid esters, see: Mariz et al. (2010[Mariz, R., Poater, A., Gatti, M., Drinkel, E., Bürgi, J. J., Luan, X., Blumentritt, S., Linden, A., Cavallo, L. & Dorta, R. (2010). Chem. Eur. J. 16, 14335-14347.]); Heinemann et al. (2007[Heinemann, F. W., Weber, I. & Zenneck, U. (2007). J. Chem. Crystallogr. 37, 165-170.]); Cherkaoui & Nicoud (1995[Cherkaoui, M. Z. & Nicoud, J.-F. (1995). New J. Chem. 19, 851-861.]).

[Scheme 1]

Experimental

Crystal data
  • C18H26O4S

  • Mr = 338.45

  • Monoclinic, P 21

  • a = 9.7918 (2) Å

  • b = 9.3938 (2) Å

  • c = 10.6998 (2) Å

  • [beta] = 112.176 (2)°

  • V = 911.39 (3) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.72 mm-1

  • T = 150 K

  • 0.26 × 0.22 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur PX diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.660, Tmax = 0.872

  • 4681 measured reflections

  • 2354 independent reflections

  • 2115 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.078

  • S = 1.07

  • 2354 reflections

  • 209 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 767 Friedel pairs

  • Flack parameter: 0.038 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O4i 0.95 2.42 3.337 (3) 161
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2089 ).


Acknowledgements

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze), where the data collection was performed.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Cherkaoui, M. Z. & Nicoud, J.-F. (1995). New J. Chem. 19, 851-861.  [ChemPort]
Drabowicz, J., Bujnicki, B. & Mikolajczyk, M. (1982). J. Org. Chem. 47, 3325-3327.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Heinemann, F. W., Weber, I. & Zenneck, U. (2007). J. Chem. Crystallogr. 37, 165-170.  [ISI] [CSD] [CrossRef] [ChemPort]
Klunder, J. M. & Sharpless, K. B. (1987). J. Org. Chem. 52, 2598-2602.  [CrossRef] [ChemPort]
Mariz, R., Poater, A., Gatti, M., Drinkel, E., Bürgi, J. J., Luan, X., Blumentritt, S., Linden, A., Cavallo, L. & Dorta, R. (2010). Chem. Eur. J. 16, 14335-14347.  [CSD] [CrossRef] [ChemPort] [PubMed]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oertling, H., Reckziegel, A., Surburg, H. & Bertram, H.-J. (2007). Chem. Rev. 107, 2136-2164.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Solladié, G., Hutt, J. & Girardin, A. (1987). Synthesis, pp. 173-173.


Acta Cryst (2013). E69, o731  [ doi:10.1107/S1600536813009112 ]

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