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Volume 69 
Part 8 
Pages o1359-o1360  
August 2013  

Received 10 July 2013
Accepted 22 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.029
wR = 0.063
Data-to-parameter ratio = 31.5
Details
Open access

Bis(1-ethyl-3-methylimidazolium) 3,6-diselanylidene-1,2,4,5-tetraselena-3,6-diphosphacyclohexane-3,6-diselenolate

aLake Forest College, 555 N. Sheridan Rd, Lake Forest, IL 60045, USA, and bInstitut des Matériaux Jean Rouxel (IMN), UMR 6502 CNRS-Université de Nantes, 2 rue de la Houssinière, BP 32229, 44322 Nantes Cedex 03, France
Correspondence e-mail: cody@lakeforest.edu

In the title compound, 2C6H11N2+·P2Se82- or [EMIM]2P2Se8 (EMIM = 1-ethyl-3-methylimidazolium), the anions, located about inversion centers between EMIM cations, exhibit a cyclohexane-like chair conformation. The cations are found in columns along the a axis, with centroid-centroid distances of 3.8399 (3) and 4.7530 (2) Å. The observed P-Se distances and Se-P-Se angles agree with other salts of this anion.

Related literature

For similar selenophosphate compounds, see: Biswas et al. (2010[Biswas, K., Zhang, Q., Chung, I., Song, J., Androulakis, J., Freeman, A. J. & Kanatzidis, M. G. (2010). J. Am. Chem. Soc. 132, 14760-14762.]); Lin et al. (2012[Lin, Y., Massa, W. & Dehnen, S. (2012). Chem. Eur. J. 18, 13427-, 13434.]). For ionothermal reactions in room-temperature ionic liquids, see: Morris (2009[Morris, R. E. (2009). Chem. Commun. pp. 2990-2998.]); Parnham & Morris (2007[Parnham, E. R. & Morris, R. E. (2007). Acc. Chem. Res. 40, 1005-1013.]); Cody et al. (2012[Cody, J. A., Finch, K. B., Reynders, G. J. III, Alexander, G. C. B., Lim, H. G., Näther, C. & Bensch, W. (2012). Inorg. Chem. 51, 13357-13362.]). For the preparation of EMIM(BF4), see: Egashira et al. (2006[Egashira, M., Yamamoto, Y., Fukutake, T., Yoshimoto, N. & Morita, M. (2006). J. Fluorine Chem. 127, 1261-1264.]). For the structure of the P2Se82- anion, see: Zhao et al. (1992[Zhao, J., Pennington, W. T. & Kolis, J. W. (1992). J. Chem. Soc. Chem. Commun. pp. 265-266.]); Rotter et al. (2008[Rotter, C., Schuster, M., Kidik, M., Schön, O., Klapötke, T. M. & Karaghiosoff, K. (2008). Inorg. Chem. 47, 1663-1673.]). For [pi]-[pi] interactions between imidazolium cations, see: Wilkes & Zaworotko (1993[Wilkes, J. S. & Zaworotko, M. J. (1993). Supramol. Chem. 1, 191-193.]).

[Scheme 1]

Experimental

Crystal data
  • 2C6H11N2+·P2Se82-

  • Mr = 915.96

  • Triclinic, [P \overline 1]

  • a = 7.8885 (4) Å

  • b = 9.3783 (4) Å

  • c = 9.8039 (5) Å

  • [alpha] = 110.390 (3)°

  • [beta] = 96.395 (4)°

  • [gamma] = 102.992 (5)°

  • V = 648.00 (5) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 11.41 mm-1

  • T = 293 K

  • 0.19 × 0.07 × 0.03 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: Gaussian [JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]) and X-SHAPE (Stoe & Cie, 1998[Stoe & Cie (1998). X-SHAPE. Stoe & Cie, Darmstadt, Germany.])] Tmin = 0.204, Tmax = 0.754

  • 22118 measured reflections

  • 3719 independent reflections

  • 2622 reflections with I > 2[sigma](I)

  • Rint = 0.072

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.063

  • S = 1.02

  • 3719 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Selected geometric parameters (Å, °)

P1-Se4 2.1104 (8)
P1-Se3 2.1334 (8)
P1-Se1 2.2794 (9)
P1-Se2i 2.2809 (8)
Se1-Se2 2.3442 (5)
Se4-P1-Se3 122.19 (4)
Se4-P1-Se1 113.49 (4)
Se3-P1-Se1 100.04 (3)
Se4-P1-Se2i 113.90 (4)
Se3-P1-Se2i 100.49 (3)
Se1-P1-Se2i 104.32 (3)
P1-Se1-Se2 102.89 (2)
P1i-Se2-Se1 102.37 (2)
Symmetry code: (i) -x+1, -y, -z.

Data collection: COLLECT (Hooft, 2009[Hooft, R. W. W. (2009). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: COLLECT; data reduction: COLLECT; 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 & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2314 ).


Acknowledgements

We thank Lake Forest College and Pays de la Loire for sabbatical support for JAC at the Institut des Matériaux Jean Rouxel (IMN) in Nantes, France. We also thank Stéphane Jobic for his assistance with this structure and sabbatical.

References

Biswas, K., Zhang, Q., Chung, I., Song, J., Androulakis, J., Freeman, A. J. & Kanatzidis, M. G. (2010). J. Am. Chem. Soc. 132, 14760-14762.  [CrossRef] [ChemPort] [PubMed]
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cody, J. A., Finch, K. B., Reynders, G. J. III, Alexander, G. C. B., Lim, H. G., Näther, C. & Bensch, W. (2012). Inorg. Chem. 51, 13357-13362.  [CrossRef] [ChemPort] [PubMed]
Egashira, M., Yamamoto, Y., Fukutake, T., Yoshimoto, N. & Morita, M. (2006). J. Fluorine Chem. 127, 1261-1264.  [CrossRef] [ChemPort]
Hooft, R. W. W. (2009). COLLECT. Nonius BV, Delft, The Netherlands.
Lin, Y., Massa, W. & Dehnen, S. (2012). Chem. Eur. J. 18, 13427-, 13434.
Morris, R. E. (2009). Chem. Commun. pp. 2990-2998.  [CrossRef]
Parnham, E. R. & Morris, R. E. (2007). Acc. Chem. Res. 40, 1005-1013.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Rotter, C., Schuster, M., Kidik, M., Schön, O., Klapötke, T. M. & Karaghiosoff, K. (2008). Inorg. Chem. 47, 1663-1673.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (1998). X-SHAPE. Stoe & Cie, Darmstadt, Germany.
Wilkes, J. S. & Zaworotko, M. J. (1993). Supramol. Chem. 1, 191-193.  [CrossRef] [ChemPort]
Zhao, J., Pennington, W. T. & Kolis, J. W. (1992). J. Chem. Soc. Chem. Commun. pp. 265-266.  [CrossRef]


Acta Cryst (2013). E69, o1359-o1360   [ doi:10.1107/S1600536813020308 ]

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