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Volume 66 
Part 9 
Pages m1080-m1081  
September 2010  

Received 14 July 2010
Accepted 4 August 2010
Online 11 August 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.019 Å
R = 0.062
wR = 0.144
Data-to-parameter ratio = 18.5
Details
Open access

3,3-Dimethyl-1,1-(propane-1,3-diyl)diimidazol-1-ium tetrabromidocadmate(II)

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and bDepartment of Light Chemical Engineering, College of Food Science and Light Industry, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: kingwell2004@sina.com.cn

The title compound, (C11H18N4)[CdBr4], was prepared by an anion exchange. The dihedral angle between the two planar imidazolium rings in the cation is 74.4 (4)°. The crystal packing is stabilized by weak intermolecular C-H...Br hydrogen bonds between the cation and the tetrahedral anion, building up a three-dimensionnal network.

Related literature

For the properties and applications of ionic liquids, see: Welton (1999[Welton, T. (1999). Chem. Rev. 99, 2071-2083.]); Nicholas et al. (2004[Nicholas, G., Garcia, M. T. & Scammells, P. J. (2004). Green Chem. 6, 166-175.]); Yu et al. (2007[Yu, G. Q., Yan, S. Q., Zhou, F., Liu, X. Q., Liu, W. M. & Liang, Y. M. (2007). Tribol. Lett. 25, 197-205]). For dicationic ionic liquids, see: Jared et al. (2005[Jared, L. A., Ding, R. F., Ellern, A. & Armstrong, D. W. (2005). J. Am. Chem. Soc. 127, 593-604.]); Liang et al. (2008[Liang, J., Dong, S., Cang, H. & Wang, J. (2008). Acta Cryst. E64, o2480.]); Song et al. (2009[Song, L. C., Luo, X., Wang, Y. Z., Gai, B. & Hu, Q. M. (2009). J. Organomet. Chem. 694, 103-112.]); Geng et al. (2010[Geng, H., Zhuang, L., Zhang, J., Wang, G. & Yuan, A. (2010). Acta Cryst. E66, o1267.]). For related structures, see: Jared et al. (2005[Jared, L. A., Ding, R. F., Ellern, A. & Armstrong, D. W. (2005). J. Am. Chem. Soc. 127, 593-604.]); Liang et al. (2008[Liang, J., Dong, S., Cang, H. & Wang, J. (2008). Acta Cryst. E64, o2480.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • (C11H18N4)[CdBr4]

  • Mr = 638.33

  • Monoclinic, P 21 /c

  • a = 8.5050 (17) Å

  • b = 15.876 (3) Å

  • c = 13.836 (3) Å

  • [beta] = 96.07 (3)°

  • V = 1857.7 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 9.78 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.245, Tmax = 0.442

  • 3383 measured reflections

  • 3383 independent reflections

  • 1874 reflections with I > 2[sigma](I)

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.144

  • S = 0.95

  • 3383 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.72 e Å-3

  • [Delta][rho]min = -0.77 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7A...Br2 0.97 2.67 3.515 (15) 145
C1-H1C...Br3i 0.96 2.93 3.819 (13) 155
C4-H4A...Br3ii 0.93 2.70 3.606 (11) 164
C5-H5B...Br3iii 0.97 2.84 3.765 (11) 161
C8-H8A...Br4iv 0.93 2.86 3.699 (12) 151
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z; (iii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2593 ).


Acknowledgements

This work was supported by the Foundation for Young Teachers Scholarship of Nanjing University of Technology, Jiangsu, China (grant No. 39729005). The authors also thank the Centre of Testing and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Geng, H., Zhuang, L., Zhang, J., Wang, G. & Yuan, A. (2010). Acta Cryst. E66, o1267.  [CrossRef] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Jared, L. A., Ding, R. F., Ellern, A. & Armstrong, D. W. (2005). J. Am. Chem. Soc. 127, 593-604.  [ISI] [PubMed]
Liang, J., Dong, S., Cang, H. & Wang, J. (2008). Acta Cryst. E64, o2480.  [CSD] [CrossRef] [details]
Nicholas, G., Garcia, M. T. & Scammells, P. J. (2004). Green Chem. 6, 166-175.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Song, L. C., Luo, X., Wang, Y. Z., Gai, B. & Hu, Q. M. (2009). J. Organomet. Chem. 694, 103-112.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Welton, T. (1999). Chem. Rev. 99, 2071-2083.  [ISI] [CrossRef] [PubMed] [ChemPort]
Yu, G. Q., Yan, S. Q., Zhou, F., Liu, X. Q., Liu, W. M. & Liang, Y. M. (2007). Tribol. Lett. 25, 197-205  [CrossRef] [ChemPort]


Acta Cryst (2010). E66, m1080-m1081   [ doi:10.1107/S1600536810031211 ]

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