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Volume 69 
Part 9 
Pages o1464-o1465  
September 2013  

Received 13 April 2013
Accepted 19 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.089
Data-to-parameter ratio = 17.0
Details
Open access

Tricyclo[3.3.1.03,7]nonane-3,7-diyl bis(4-methylbenzenesulfonate)

aChemistry Department, University of Cyprus, Nicosia, 1678, Cyprus
Correspondence e-mail: ioannou.savvas@ucy.ac.cy

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-H...O interactions present in the structure. As a consequence, the packing of the molecule (viewed along [100]) appears as chains where the molecules run parallel, but each chain has the opposite direction to the neighboring ones.

Related literature

For reviews on noradamantene and analogous pyramidalized alkenes, see: Borden (1989[Borden, W. T. (1989). Chem. Rev. 89, 1095-1109.], 1996[Borden, W. T. (1996). Synlett, pp. 711-719.]); Vazquez & Camps (2005[Vazquez, S. & Camps, P. (2005). Tetrahedron, 61, 5147-5208.]). For tosylates, see: Hoffman (1965[Hoffman, H. M. R. (1965). J. Chem. Soc. pp. 6753-6761.]). For related structures, see: Ioannou & Nicolaides (2009[Ioannou, S. & Nicolaides, A. V. (2009). Tetrahedron Lett. 50, 6938-6940.]); Ioannou et al. (2010[Ioannou, S., Nicolaides, A. V. & Manos, M. J. (2010). Acta Cryst. E66, o409.], 2012a[Ioannou, S. & Moushi, E. (2012a). Acta Cryst. E68, o1719.]), and for polycyclic compounds prepared from noradamantene, see: Ioannou et al. (2012b[Ioannou, S. & Moushi, E. (2012b). Acta Cryst. E68, o2150.],c[Ioannou, S. & Moushi, E. (2012c). Acta Cryst. E68, o2340-o2341.], 2013[Ioannou, S., Krassos, H. & Nicolaides, A. V. (2013). Tetrahedron, 69, 8064-8068.]). For a description of the Cambridge Crystallographic Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C23H26O6S2

  • Mr = 462.58

  • Monoclinic, C 2/c

  • a = 22.3068 (8) Å

  • b = 7.5667 (2) Å

  • c = 12.7114 (5) Å

  • [beta] = 98.837 (4)°

  • V = 2120.07 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 100 K

  • 0.68 × 0.20 × 0.05 mm

Data collection
  • Oxford Diffraction SuperNova diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.933, Tmax = 0.986

  • 17770 measured reflections

  • 2420 independent reflections

  • 2210 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.089

  • S = 1.09

  • 2420 reflections

  • 142 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4A...O3i 0.99 2.49 3.4714 (16) 171
C10-H10...O2ii 0.95 2.57 3.2551 (19) 129
C12-H12C...O2iii 0.98 2.49 3.4444 (19) 164
Symmetry codes: (i) [-x+1, y-1, -z+{\script{1\over 2}}]; (ii) [x, -y+1, z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Mercury (Macrae et al., 2006[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.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2286 ).


Acknowledgements

We are grateful to the Research Promotion Foundation (I[Pi]E) of Cyprus and the European Structural Funds for grant ANABA[Theta]/[Pi]A[Gamma]IO/0308/12 which allowed the purchase of the XRD instrument, NEK[Pi]/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 ([Pi]ENEK/ENI[Sigma]X/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.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Borden, W. T. (1989). Chem. Rev. 89, 1095-1109.  [CrossRef] [ChemPort] [ISI]
Borden, W. T. (1996). Synlett, pp. 711-719.  [CrossRef]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hoffman, H. M. R. (1965). J. Chem. Soc. pp. 6753-6761.
Ioannou, S., Krassos, H. & Nicolaides, A. V. (2013). Tetrahedron, 69, 8064-8068.  [CSD] [CrossRef] [ChemPort]
Ioannou, S. & Moushi, E. (2012a). Acta Cryst. E68, o1719.  [CSD] [CrossRef] [details]
Ioannou, S. & Moushi, E. (2012b). Acta Cryst. E68, o2150.  [CSD] [CrossRef] [details]
Ioannou, S. & Moushi, E. (2012c). Acta Cryst. E68, o2340-o2341.  [CSD] [CrossRef] [ChemPort] [details]
Ioannou, S. & Nicolaides, A. V. (2009). Tetrahedron Lett. 50, 6938-6940.  [ISI] [CrossRef] [ChemPort]
Ioannou, S., Nicolaides, A. V. & Manos, M. J. (2010). Acta Cryst. E66, o409.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Vazquez, S. & Camps, P. (2005). Tetrahedron, 61, 5147-5208.  [ChemPort]


Acta Cryst (2013). E69, o1464-o1465   [ doi:10.1107/S1600536813023234 ]

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