(R)-2′-Benz­yloxy-5,5′,6,6′,7,7′,8,8′-octa­hydro-1,1′-binaphthyl-2-ol

Abreu, A.R.; Ramos Silva, M.; Pereira, M.M.; Bayon, J.C.; Matos Beja, A.

doi:10.1107/S1600536810002308

Volume 66
Part 2
Page o437
February 2010

Received 28 December 2009
Accepted 18 January 2010
Online 23 January 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.038
wR = 0.094
Data-to-parameter ratio = 7.0
Details

(R)-2'-Benzyloxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2-ol

Artur R. Abreu,^a Manuela Ramos Silva,^b ^* Mariette M. Pereira,^a J. Carles Bayon ^c and Ana Matos Beja ^b

^aChemistry Department, University of Coimbra, P-3004-516 Coimbra, Portugal,^bCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^cChemistry Department, University of Barcelona, Bellaterra, 08193 Barcelona, Portugal
Correspondence e-mail: manuela@pollux.fis.uc.pt

The molecules of the title compound, C₂₇H₂₈O₂, exhibit axial chirality. The planes of the aromatic rings of the tetralin ring systems make an angle of 85.72 (11)°. The non-aromatic rings adopt distorted half-chair conformations. In one of them, two C atoms of the four-atom aliphatic chain are disordered over two sites in a 0.75 (2):0.25 (2) ratio. The substituent phenyl ring is also disordered over two positions in a 0.59 (3):0.41 (3) ratio. There are no conventional hydrogen bonds joining the molecules.

Related literature

For the use of 1,1'-binaphthyl-2,2'-diol in asymmetric synthesis, see: Brunel (2005) Nájera et al. (2009). For the catalytic properties of related compounds, see: Zhang et al. (1997); Reetz et al. (1997); Chan et al. (1997); Waltz et al. (2004). For the synthetic procedure, see: Carrilho et al. (2009); Abreu et al. (2010).

Experimental

Crystal data

C₂₇H₂₈O₂
M_r = 384.49
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.9871 (3) Å
b = 11.6926 (3) Å
c = 20.0324 (5) Å
V = 2105.06 (10) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.30 × 0.30 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) T_min = 0.944, T_max = 0.999
26201 measured reflections
2294 independent reflections
1798 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.094
S = 1.09
2294 reflections
329 parameters
H-atom parameters constrained
_max = 0.12 e Å^-3
_min = -0.15 e Å^-3

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2312 ).

Acknowledgements

This work was supported by the Fundação para a Ciência e a Tecnologia (FCT) through project PTDC/QUI/66015/2006 and Merquinsa (Barcelona, Spain). ARA also thanks the FCT for a PhD grant (SFRH/BD/21314/2005).

References

Abreu, A. R., Bayón, J. C. & Pereira, M. M. (2010). Tetrahedron, 66, 743-749.
Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Brunel, J. M. (2005). Chem. Rev. 105, 857-897.
Carrilho, R. M. B., Abreu, A. R., Peticz, G., Bayón, J. C., Moreno, M. J. S. M., Kollár, L. & Pereira, M. M. (2009). Chem. Lett. 8, 844-845.
Chan, A. S. C., Zhang, F.-Y. & Yip, C.-W. (1997). J. Am. Chem. Soc. 119, 4080-4081.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Nájera, C., Sansano, J. & Saá, J. M. (2009). Eur. J. Org. Chem. pp. 2385-2400.
Reetz, M. T., Merk, C., Naberfeld, G., Rudolph, J., Gribenow, N. & Goddard, R. (1997). Tetrahedron Lett. 38, 5273-5276.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Waltz, K. M., Carroll, P. J. & Walsh, P. J. (2004). Organometallics, 23, 127-134.
Zhang, F.-Y., Yip, C.-W., Cao, R. & Chan, A. S. C. (1997). Tetrahedron Asymmetry, 8, 585-589.

organic compounds