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Volume 69 
Part 2 
Page o265  
February 2013  

Received 5 December 2012
Accepted 16 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.148
Data-to-parameter ratio = 16.7
Details
Open access

(6R*,10R*)-Dimethyl 1,4-dioxaspiro[4.5]decane-6,10-dicarboxylate

aCentre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, 221 00 Lund, Sweden, and bCentre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 123, 221 00 Lund, Sweden
Correspondence e-mail: daniel.strand@chem.lu.se

The title compound, C12H18O6, is in the usual chair conformation with the two ester functions in a 1,3-trans orientation. With a value of 1.439 (2) Å, the pseudo-axial C-O bond of the 1,3-dioxolane ring is slightly longer than the corresponding equatorial C-O bond of 1.424 (3) Å. The O-C-O angle of the dioxolane ring is 106.25 (17)°.

Related literature

The starting material (1R,3S)-dimethyl 2-oxocyclohexane-1,3-dicarboxylate was prepared following a known procedure (Blicke & McCarty, 1959[Blicke, F. F. & McCarty, F. J. (1959). J. Org. Chem. 24, 1069-1076.]). Alternative methods for the synthesis of this coumpound include alkylation of cyclohexanone (Balasubrahmanyam & Balasubramanian, 1969[Balasubrahmanyam, S. N. & Balasubramanian, M. (1969). Org. Synth. 49, 56-61.]; Beckman & Munshi, 2011[Beckman, E. J. & Munshi, P. (2011). Green Chem. 13, 376-383.]). Synthesis and characterization of a related 1,3-trans-dicarboxylate cyclohexanone has been reported (Scaric & Turjak-Cebic, 1982[Scaric, V. & Turjak-Cebic, V. (1982). Croat. Chem. Acta, 55, 457-65.]). The acetal formation follows standard procedures (Wuts & Greene, 2007[Wuts, P. G. M. & Greene, T. W. (2007). In Greene's Protective Groups in Organic Synthesis. Hoboken, NJ: Wiley Interscience.]).

[Scheme 1]

Experimental

Crystal data
  • C12H18O6

  • Mr = 258.26

  • Monoclinic, P c

  • a = 8.6243 (9) Å

  • b = 7.3203 (6) Å

  • c = 10.1704 (9) Å

  • [beta] = 91.719 (8)°

  • V = 641.79 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.2 × 0.2 × 0.05 mm

Data collection
  • Agilent Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.919, Tmax = 1.000

  • 5645 measured reflections

  • 2717 independent reflections

  • 2329 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.148

  • S = 1.03

  • 2717 reflections

  • 163 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: CrystalMaker (CrystalMaker, 2011[CrystalMaker (2011). CrystalMaker. CrystalMaker Software Ltd, Oxfordshire, England.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2225 ).


Acknowledgements

Lund University, the Swedish Research Council, the Knut and Alice Wallenberg Foundation and the Royal Physiographic Society in Lund are gratefully acknowledged for financial support.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Balasubrahmanyam, S. N. & Balasubramanian, M. (1969). Org. Synth. 49, 56-61.  [ChemPort]
Beckman, E. J. & Munshi, P. (2011). Green Chem. 13, 376-383.  [ISI] [CrossRef] [ChemPort]
Blicke, F. F. & McCarty, F. J. (1959). J. Org. Chem. 24, 1069-1076.  [CrossRef] [ChemPort]
CrystalMaker (2011). CrystalMaker. CrystalMaker Software Ltd, Oxfordshire, England.
Scaric, V. & Turjak-Cebic, V. (1982). Croat. Chem. Acta, 55, 457-65.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wuts, P. G. M. & Greene, T. W. (2007). In Greene's Protective Groups in Organic Synthesis. Hoboken, NJ: Wiley Interscience.


Acta Cryst (2013). E69, o265  [ doi:10.1107/S160053681300161X ]

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