Decachloro­hexa-1,5-diene

Schollmeyer, D.; Detert, H.

doi:10.1107/S1600536812019769

Volume 68
Part 6
Page o1685
June 2012

Received 30 April 2012
Accepted 2 May 2012
Online 12 May 2012

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R = 0.030
wR = 0.075
Data-to-parameter ratio = 21.9
Details

Decachlorohexa-1,5-diene

Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: detert@uni-mainz.de

The title compound, C₆Cl₁₀, cystallizes in a nearly C2-symmetrical gauche conformation. Both trichlorovinyl groups are nearly planar [Cl-C-C-Cl torsion angles = -178.47 (12) and -179.93 (11)°] and the lengths of their C-Cl bonds increase from the terminal trans and cis C-Cl bonds to the internal bonds. The Cl-C-Cl bond angles of the terminal dichloromethylene units are compressed to 111.75 (11) and 111.40 (11)°.

Related literature

For the synthesis of perchloroalkenes, see: Prins (1949); Roedig et al. (1963). For structures of perchloroalkenes, see: Herbstein (1979); Rao & Livingston (1958); Hopf et al. (1991); Detert et al. (2009). For rearrangements of highly halogenated alkenes, see: Maahs (1963); Herges et al. (2005). For recent reactions of perchloroalkenes, see: Schmidt et al. (2009); Rahimi & Schmidt (2010).

Experimental

Crystal data

C₆Cl₁₀
M_r = 426.56
Monoclinic, P 2₁ /c
a = 12.8936 (5) Å
b = 6.7051 (2) Å
c = 15.3753 (5) Å
= 93.858 (3)°
V = 1326.23 (8) Å³
Z = 4
Mo K radiation
= 2.07 mm^-1
T = 193 K
0.15 × 0.15 × 0.15 mm

Data collection

Stoe IPDS 2T diffractometer
Absorption correction: multi-scan (PLATON; Spek, 2009) T_min = 0.747, T_max = 0.747
18142 measured reflections
3181 independent reflections
2991 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.075
S = 1.06
3181 reflections
145 parameters
_max = 0.94 e Å^-3
_min = -0.44 e Å^-3

Data collection: X-AREA (Stoe & Cie, 2011); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2011); program(s) used to solve structure: SIR97 (Altomare et al. 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5907 ).

Acknowledgements

The authors are grateful to Dieter Lenoir for helpful discussions.

References

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Herbstein, F. H. (1979). Acta Cryst. B35, 1661-1670.
Herges, R., Papafilipopoulos, A., Hess, K., Lenoir, D., Chiappe, C. & Detert, H. (2005). Angew. Chem. Int. Ed. Engl. 44, 1412-1416.
Hopf, H., Stamm, R. & Jones, P. G. (1991). Chem. Ber. 124, 1291-1294.
Maahs, G. (1963). Angew. Chem. 75, 451-451.
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Rao, C. N. R. & Livingston, R. (1958). Curr. Sci. 27, 330-331.
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Schmidt, A., Rahimi, A. & Gjikai, M. (2009). Synthesis, pp. 2371-2378.
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Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stoe & Cie (2011). X-RED and X-AREA. Stoe & Cie GmbH, Darmstadt, Germany.

organic compounds