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Volume 69 
Part 3 
Page o325  
March 2013  

Received 28 January 2013
Accepted 29 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.062
wR = 0.165
Data-to-parameter ratio = 19.9
Details
Open access

(±)-(4aR,5R,8S,8aR)-8-(tert-Butyldimethylsilyloxy)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione

aDepartment of Chemistry, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: felixdelling@ufscar.br

In the title compound, C19H30O3Si, both rings adopt a half-boat conformation. Overall, the molecule approximates a U-shape as the cyclo-2-ene-1,4-dione and butyldimethylsilyloxy substituents lie to the same side of the central cyclohexene ring; the methyl substituent lies to the other side of the molecule. In the crystal, linear supramolecular chains along the b axis are sustained by C-H...O interactions.

Related literature

For a general description of the synthesis of higher terpenoids using the Diels-Alder reaction, see: Brocksom et al. (2001[Brocksom, T. J., Correa, A. G., Naves, R. M., Silva, F. Jr, Catani, V., Ceschi, M. A., Zukerman-Schpector, J., Toloi, A. P., Ferreira, M. L. & Brocksom, U. (2001). Diels-Alder Reactions in the Synthesis of Higher Terpenes, in Organic Synthesis: Theory and Applications, Vol. 5, edited by T. Hudlicky, pp. 390-87. London: JAI/Elsevier Science.]). For the synthesis of a similar compound containing an N atom in place of the O atom, see: Vieira et al. (2007[Vieira, Y. W., Nakamura, J., Finelli, F. G., Brocksom, U. & Brocksom, T. J. (2007). J. Braz. Chem. Soc. 18, 448-451.]). For the synthesis, see: Finelli (2004[Finelli, F. G. (2004). MSc thesis, Universidade Federal de São Carlos, Brazil.]). For additional conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C19H30O3Si

  • Mr = 334.52

  • Monoclinic, P 2/c

  • a = 15.325 (2) Å

  • b = 7.1744 (9) Å

  • c = 17.965 (2) Å

  • [beta] = 93.577 (9)°

  • V = 1971.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.15 × 0.10 × 0.08 mm

Data collection
  • Enraf-Nonius CAD-4 MACH 3 diffractometer

  • 4451 measured reflections

  • 4305 independent reflections

  • 1463 reflections with I > 2[sigma](I)

  • Rint = 0.072

  • 3 standard reflections every 30 min intensity decay: 1.4%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.165

  • S = 0.93

  • 4305 reflections

  • 216 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...O2i 0.98 2.55 3.524 (5) 171
Symmetry code: (i) x, y+1, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990[Fair, C. K. (1990). MolEN. Enraf-Nonius, Delft, The Netherlands.]); program(s) used to solve structure: SIR92 (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.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and MarvinSketch (ChemAxon, 2009[ChemAxon (2009). MarvinSketch. www.chemaxon.com.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5287 ).


Acknowledgements

We thank CNPq (142088/2011-0 to FND, 306532/2009-3 to JZS), FAPESP (2011/13993-2 to TJB), and CAPES (grant No. 808/2009 to JZS) for financial support. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12)

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]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brocksom, T. J., Correa, A. G., Naves, R. M., Silva, F. Jr, Catani, V., Ceschi, M. A., Zukerman-Schpector, J., Toloi, A. P., Ferreira, M. L. & Brocksom, U. (2001). Diels-Alder Reactions in the Synthesis of Higher Terpenes, in Organic Synthesis: Theory and Applications, Vol. 5, edited by T. Hudlicky, pp. 390-87. London: JAI/Elsevier Science.
ChemAxon (2009). MarvinSketch. www.chemaxon.com.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Fair, C. K. (1990). MolEN. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Finelli, F. G. (2004). MSc thesis, Universidade Federal de São Carlos, Brazil.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vieira, Y. W., Nakamura, J., Finelli, F. G., Brocksom, U. & Brocksom, T. J. (2007). J. Braz. Chem. Soc. 18, 448-451.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o325  [ doi:10.1107/S1600536813002973 ]

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