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Volume 69 
Part 8 
Pages o1216-o1217  
August 2013  

Received 7 June 2013
Accepted 1 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.036
wR = 0.098
Data-to-parameter ratio = 10.7
Details
Open access

Bis(1,3-dimethyl-1H-imidazolium) hexafluorosilicate methanol 0.33-solvate

aCollege of Chemistry, Leshan Normal University, Binhe Rd 778, Leshan 614000, Sichuan Province, People's Republic of China
Correspondence e-mail: maxborzov@mail.ru

The title compound, 6C5H9N2+·3SiF62-·CH3OH, (I), was prepared by recrystallization of the crude salt from methanol along with solvent-free 2C5H9N2+·SiF62- (II). Crystals of these solvatomorphs can be separated manually. The solvate (I) crystallizes in a rare hexagonal space group P6/mcc. Its asymmetric unit comprises one half of an imidazolium cation bisected by the crystallographic m-plane, one-sixth and one-twelfth of two crystallographically independent SiF62- dianions (Si atoms are located on the 3.2 and 6/m inversion centres), and one-twelfth of a methanol molecule (C atoms are situated on the 622 inversion centres, other atoms are disordered between general positions). In (I), all F atoms of 3.2-located SiF62- dianions participate in the formation of symmetry-equivalent contacts to the H atoms of imidazolium fragments, thus forming rod-type ensembles positioned on the -6 axes. These `pillar' rods are, in turn, F...H interlinked through SiF62- dianions disordered around the 6/m centres. The twelvefold disordered methanol molecules are appended to this array by O-H...F hydrogen bonds to the 6/m located SiF62- dianions. In terms of graph-set notation, the first and second level networks in (I) are N1 = C22(7)[3R44(14)]D22(4) and N2 = D22(5) (C-H...O hydrogen bonds are not considered). After locating all symmetrically independent atoms in the cation and anions, there remained a strong (> 3 e Å-3) residual electron density peak located at the 622 inversion centre. Treatment of this pre-refined model with the SQUEEZE procedure in PLATON [Spek (2009). Acta Cryst. D65, 148-155] revealed two voids per unit cell, indicative of the presence of the solvent methanol molecule disordered about the 622 inversion centre.

Related literature

For solvatomorphs of (I)[link], see: Light et al. (2007[Light, M. E., Bates, G. W. & Gale, P. A. (2007). Private communication (refcode NIQFAV). CCDC, Cambridge, England.]); Tian et al. (2013[Tian, C., Nie, W. & Borzov, M. V. (2013). Acta Cryst. E69, o1218-o1219.]). For solvatomorphism of (1,3-dimethyl-1H-imidazolium) hexafluorophosphate, C5H9N2+·PF6-, see: Holbrey et al. (2003[Holbrey, J. D., Reichert, W. M. & Nieuwenhuyzen, M. (2003). Chem. Commun. pp. 476-477.]). For the practical utility of sterically non-hindered 1,3-dialkyl-1H-imidazolium salts with BF4- and PF6- anions for the preparation of Arduengo carbene adducts with BF3 and PF5, see: Tian et al. (2012[Tian, C., Nie, W., Borzov, M. V. & Su, P. (2012). Organometallics, 31, 1751-1760.]). For graph-set notation, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Grell et al. (1999[Grell, J., Bernstein, J. & Tinhofer, G. (1999). Graph Set Analysis of Some Hydrogen Bond Patterns. Some Mathematical Concepts, edited by H. Wähling. München: Fakultät für Mathematik und Informatik, Technische Universität München.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the SQUEEZE procedure in PLATON, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • 6C5H9N2+·3SiF62-·CH4O

  • Mr = 1041.10

  • Hexagonal, P 6/m c c

  • a = 12.6577 (7) Å

  • c = 16.8174 (18) Å

  • V = 2333.5 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 296 K

  • 0.32 × 0.20 × 0.15 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.934, Tmax = 0.968

  • 11115 measured reflections

  • 804 independent reflections

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

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.098

  • S = 1.10

  • 804 reflections

  • 75 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...F1 0.85 1.96 (1) 2.80 (3) 177 (13)
C1-H1...F1 0.94 (3) 2.24 (3) 3.044 (3) 143 (2)
C2-H2...F2i 0.92 (2) 2.21 (2) 3.095 (2) 160.3 (17)
Symmetry code: (i) -x+1, -y+1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXTL and OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2435 ).


Acknowledgements

Financial support from the National Natural Science Foundation of China (project Nos. 20702041 and 21072157) and the Shaanxi Province Administration of Foreign Experts Bureau Foundation (grant No. 20106100079) is gratefully acknowledged. The authors are thankful to Mr Su Pengfei (Xi'an Modern Chemistry Research Institute) for his help in carrying out X-ray diffraction measurements.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [Web of Science] [IUCr Journals]
Grell, J., Bernstein, J. & Tinhofer, G. (1999). Graph Set Analysis of Some Hydrogen Bond Patterns. Some Mathematical Concepts, edited by H. Wähling. München: Fakultät für Mathematik und Informatik, Technische Universität München.
Holbrey, J. D., Reichert, W. M. & Nieuwenhuyzen, M. (2003). Chem. Commun. pp. 476-477.  [CSD] [CrossRef]
Light, M. E., Bates, G. W. & Gale, P. A. (2007). Private communication (refcode NIQFAV). CCDC, Cambridge, England.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Tian, C., Nie, W. & Borzov, M. V. (2013). Acta Cryst. E69, o1218-o1219.  [CrossRef] [IUCr Journals]
Tian, C., Nie, W., Borzov, M. V. & Su, P. (2012). Organometallics, 31, 1751-1760.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1216-o1217   [ doi:10.1107/S1600536813018230 ]

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