anti-1′,6′,7′,8′,9′,14′,15′,16′-Octa­chloro­dispiro­[1,3-dioxolane-2,17′-penta­cyclo­[12.2.1.16,9.02,13.05,10]octa­decane-18′,2′′-1,3-dioxolane]-7′,15′-diene

Tenbusch, M.E.; Brooker, M.D.; Timmerman, J.C.; Jones, D.S.; Etzkorn, M.

doi:10.1107/S1600536810024669

Volume 66
Part 8
Page o1882
August 2010

Received 15 June 2010
Accepted 23 June 2010
Online 3 July 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R = 0.041
wR = 0.118
Data-to-parameter ratio = 14.7
Details

anti-1',6',7',8',9',14',15',16'-Octachlorodispiro[1,3-dioxolane-2,17'-pentacyclo[12.2.1.1^6,9.0^2,13.0^5,10]octadecane-18',2''-1,3-dioxolane]-7',15'-diene

Megan E. Tenbusch,^a Matthew D. Brooker,^a Jacob C. Timmerman,^a Daniel S. Jones ^a ^* and Markus Etzkorn ^a ^*

^aDepartment of Chemistry, The University of North Carolina at Charlotte, 9201 University City Blvd, Charlotte, NC 28223, USA
Correspondence e-mail: djones@uncc.edu, metzkorn@uncc.edu

The title compound, C₂₂H₂₀Cl₈O₄, was prepared as part of the synthesis of precursors for the preparation of fluorinated molecular tweezers. The molecule sits on an inversion center, thus requiring that the cyclooctane ring adopt a chair conformation.

Related literature

For related structures, see: Garcia et al. (1991b,c). For related chemistry on analogous polycyclic scaffolds, see: Garcia et al. (1991a); Chou et al. (2005)

Experimental

Crystal data

C₂₂H₂₀Cl₈O₄
M_r = 631.98
Monoclinic, P 2₁ /c
a = 9.5332 (7) Å
b = 7.9121 (6) Å
c = 17.014 (2) Å
= 101.099 (8)°
V = 1259.3 (2) Å³
Z = 2
Cu K radiation
= 8.44 mm^-1
T = 295 K
0.25 × 0.20 × 0.08 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: multi-scan (Blessing, 1995) T_min = 0.190, T_max = 0.561
4703 measured reflections
2275 independent reflections
1702 reflections with I > 2(I)
R_int = 0.047
3 standard reflections every 62 reflections intensity decay: 13%

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.118
S = 1.05
2275 reflections
155 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.47 e Å^-3

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF08 (Beurskens et al., 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2171 ).

Acknowledgements

This work was supported in part by funds provided by The University of North Carolina at Charlotte.

References

Beurskens, P. T., Beurskens, G., de Gelder, R., Garciía-Granda, S., Gould, R. O. & Smits, J. M. M. (2008). The DIRDIF2008 Program System. Crystallography Laboratory, University of Nijmegen, The Netherlands.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Chou, T.-H., Liao, K.-C. & Lin, J.-J. (2005). Org. Lett. 7, 4843-4846.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Garcia, J. G., Fronczek, F. R. & McLaughlin, M. L. (1991a). Acta Cryst. C47, 206-209.
Garcia, J. G., Fronczek, F. R. & McLaughlin, M. L. (1991b). Acta Cryst. C47, 451-453.
Garcia, J. G., Fronczek, F. R. & McLaughlin, M. L. (1991c). Tetrahedron Lett. 32, 3289-3292.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.