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

Jahangiri, A.; Wendt, O.F.; Strand, D.

doi:10.1107/S160053681300161X

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 (C-C) = 0.004 Å
R = 0.047
wR = 0.148
Data-to-parameter ratio = 16.7
Details

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

Amita Jahangiri,^a Ola F. Wendt ^b and Daniel Strand ^a ^*

^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). Alternative methods for the synthesis of this coumpound include alkylation of cyclohexanone (Balasubrahmanyam & Balasubramanian, 1969; Beckman & Munshi, 2011). Synthesis and characterization of a related 1,3-trans-dicarboxylate cyclohexanone has been reported (Scaric & Turjak-Cebic, 1982). The acetal formation follows standard procedures (Wuts & Greene, 2007).

Experimental

Crystal data

C₁₂H₁₈O₆
M_r = 258.26
Monoclinic, P c
a = 8.6243 (9) Å
b = 7.3203 (6) Å
c = 10.1704 (9) Å
= 91.719 (8)°
V = 641.79 (10) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.919, T_max = 1.000
5645 measured reflections
2717 independent reflections
2329 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.148
S = 1.03
2717 reflections
163 parameters
2 restraints
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.23 e Å^-3

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2011); 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.
Beckman, E. J. & Munshi, P. (2011). Green Chem. 13, 376-383.
Blicke, F. F. & McCarty, F. J. (1959). J. Org. Chem. 24, 1069-1076.
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.
Wuts, P. G. M. & Greene, T. W. (2007). In Greene's Protective Groups in Organic Synthesis. Hoboken, NJ: Wiley Interscience.

organic compounds

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