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

Delling, F.N.; Zukerman-Schpector, J.; Brocksom, T.J.; Brocksom, U.; Finelli, F.G.; Tiekink, E.R.T.

doi:10.1107/S1600536813002973

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 (C-C) = 0.006 Å
R = 0.062
wR = 0.165
Data-to-parameter ratio = 19.9
Details

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

Felix N. Delling,^a ^* Julio Zukerman-Schpector,^a Timothy J. Brocksom,^a Ursula Brocksom,^a Fernanda G. Finelli ^a and Edward R. T. Tiekink ^b

^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-HO interactions.

Related literature

For a general description of the synthesis of higher terpenoids using the Diels-Alder reaction, see: Brocksom et al. (2001). For the synthesis of a similar compound containing an N atom in place of the O atom, see: Vieira et al. (2007). For the synthesis, see: Finelli (2004). For additional conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₉H₃₀O₃Si
M_r = 334.52
Monoclinic, P 2/c
a = 15.325 (2) Å
b = 7.1744 (9) Å
c = 17.965 (2) Å
= 93.577 (9)°
V = 1971.4 (4) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.072
3 standard reflections every 30 min intensity decay: 1.4%

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.165
S = 0.93
4305 reflections
216 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9O2ⁱ	0.98	2.55	3.524 (5)	171
Symmetry code: (i) x, y+1, z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006) and MarvinSketch (ChemAxon, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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.
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.
Finelli, F. G. (2004). MSc thesis, Universidade Federal de São Carlos, Brazil.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vieira, Y. W., Nakamura, J., Finelli, F. G., Brocksom, U. & Brocksom, T. J. (2007). J. Braz. Chem. Soc. 18, 448-451.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds