Received 13 April 2013
The title compound, C23H26O6S2 was synthesized by esterification of tricyclo[3.3.1.03,7]nonane-3,7-diol with p-toluenesulfonyl chloride. The molecule has symmetry 2 and is situated on site 4e. The C-C bond length between the quartenary C atoms is 1.598 (2) Å, which is considerably longer than other C-C bonds in the molecule. There are C-HO interactions present in the structure. As a consequence, the packing of the molecule (viewed along ) appears as chains where the molecules run parallel, but each chain has the opposite direction to the neighboring ones.
For reviews on noradamantene and analogous pyramidalized alkenes, see: Borden (1989, 1996); Vazquez & Camps (2005). For tosylates, see: Hoffman (1965). For related structures, see: Ioannou & Nicolaides (2009); Ioannou et al. (2010, 2012a), and for polycyclic compounds prepared from noradamantene, see: Ioannou et al. (2012b,c, 2013). For a description of the Cambridge Crystallographic Database, see: Allen (2002).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2286 ).
We are grateful to the Research Promotion Foundation (IE) of Cyprus and the European Structural Funds for grant ANABA/AIO/0308/12 which allowed the purchase of the XRD instrument, NEK/0308/02, the purchase of a 500 MHz NMR spectrometer as well as of the RSC journal archive, and enabled the access to Reaxys, and financially supported SI (ENEK/ENIX/0308/01). Partial financial support (SI) has also been provided by the SRP "Interesting Divalent Carbon Compounds" granted by UCY. The A. G. Leventis Foundation is gratefully acknowledged for a generous donation to the University of Cyprus enabling the purchase of the 300 MHz NMR spectrometer. Dr Athanassios Nicolaides and Dr Anastasios Tasiopoulos are thanked for their illuminating comments.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Borden, W. T. (1989). Chem. Rev. 89, 1095-1109.
Borden, W. T. (1996). Synlett, pp. 711-719.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Hoffman, H. M. R. (1965). J. Chem. Soc. pp. 6753-6761.
Ioannou, S., Krassos, H. & Nicolaides, A. V. (2013). Tetrahedron, 69, 8064-8068.
Ioannou, S. & Moushi, E. (2012a). Acta Cryst. E68, o1719.
Ioannou, S. & Moushi, E. (2012b). Acta Cryst. E68, o2150.
Ioannou, S. & Moushi, E. (2012c). Acta Cryst. E68, o2340-o2341.
Ioannou, S. & Nicolaides, A. V. (2009). Tetrahedron Lett. 50, 6938-6940.
Ioannou, S., Nicolaides, A. V. & Manos, M. J. (2010). Acta Cryst. E66, o409.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vazquez, S. & Camps, P. (2005). Tetrahedron, 61, 5147-5208.