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Volume 69 
Part 4 
Page o549  
April 2013  

Received 25 February 2013
Accepted 13 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.133
Data-to-parameter ratio = 13.8
Details
Open access

1,3-Bis(6-methylpyridin-2-yl)-1H-imidazol-3-ium hexafluorophosphate

aDepartment of Chemistry, Chonbuk National University, Jeonju, Chonbuk 561-756, Republic of Korea,bCenter for Smart Supramolecules, Department of Chemistry and Division of Advanced Materials Science, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea,cDepartment of Material Science & Engineering, Kunsan National University, Jeonbuk 573-701, Republic of Korea,dDepartment of Chemistry and Research Institute of Physics and Chemistry, Chonbuk National University, Jeonju 561-756, Republic of Korea, and eDepartment of Chemistry, Kunsan National University, Kunsan, Chonbuk 573-701, Republic of Korea
Correspondence e-mail: dhl@jbnu.ac.kr, parkg@kunsan.ac.kr

In the title salt, C17H19N4+·PF6-, the two pyridine rings of the cation are inclined to one another by 15.89 (8)°, and inclined to the imidazole ring by 65.05 (10) and 64.07 (10)°. In the crystal, the cations and anions are linked via a series of C-H...N and C-H...F hydrogen bonds, forming two-dimensional networks lying parallel to (001).

Related literature

For the isolation of an N-heterocyclic carbene, see: Arduengo et al. (1991[Arduengo, A. J. III, Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.]). For related structures, see: Huang et al. (2011[Huang, K., Du, B.-X. & Liu, C.-L. (2011). Acta Cryst. E67, o2062.]); Grieco et al. (2011[Grieco, G., Blacque, O. & Berke, H. (2011). Acta Cryst. E67, o2066-o2067.]); Kim et al. (2009[Kim, G. Y., Park, S.-K., Lee, D.-H. & Park, G. (2009). Acta Cryst. E65, o637.]). For applications of N-heterocyclic carbenes in catalytic processes, see: Enders et al. (1996[Enders, D., Gielen, H., Raabe, G., Runsink, J. & Teles, J. H. (1996). Chem. Ber. 129, 1483-1488.]); Frenzel et al. (1999[Frenzel, U., Weskamp, T., Kohl, F. J., Schattenmann, W. C., Nuyken, O. & Herrmann, W. A. (1999). J. Organomet. Chem. 586, 263-265.]); Scholl et al. (1999[Scholl, M., Ding, S., Lee, C. W. & Grubbs, R. H. (1999). Org. Lett. 1, 953-956.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N4+·PF6-

  • Mr = 424.33

  • Triclinic, [P \overline 1]

  • a = 6.3839 (3) Å

  • b = 12.0353 (5) Å

  • c = 12.8006 (5) Å

  • [alpha] = 108.039 (2)°

  • [beta] = 96.091 (2)°

  • [gamma] = 100.593 (2)°

  • V = 905.12 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 100 K

  • 0.16 × 0.07 × 0.07 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.965, Tmax = 0.986

  • 19206 measured reflections

  • 3700 independent reflections

  • 2898 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.133

  • S = 0.97

  • 3700 reflections

  • 269 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...F3i 0.95 2.45 3.263 (2) 144
C7-H7A...N2ii 0.99 2.59 3.567 (2) 170
C7-H7B...F6iii 0.99 2.28 3.264 (2) 172
C10-H10...F2iv 0.95 2.53 3.373 (2) 148
C11-H11B...F4iv 0.99 2.44 3.355 (2) 154
C13-H13...F4iv 0.95 2.34 3.193 (2) 149
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) x, y, z+1; (iv) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2000[Bruker (2000). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). 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: DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). 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: NG5317 ).


Acknowledgements

This work was supported by the "Human Resource Development (project name: Advanced track for Si-based solar cell materials and devices, project No. 201040100660)" of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant funded by the Korean Government Ministry of Knowledge Economy.

References

Arduengo, A. J. III, Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2000). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Enders, D., Gielen, H., Raabe, G., Runsink, J. & Teles, J. H. (1996). Chem. Ber. 129, 1483-1488.  [CrossRef] [ChemPort]
Frenzel, U., Weskamp, T., Kohl, F. J., Schattenmann, W. C., Nuyken, O. & Herrmann, W. A. (1999). J. Organomet. Chem. 586, 263-265.  [CrossRef] [ChemPort]
Grieco, G., Blacque, O. & Berke, H. (2011). Acta Cryst. E67, o2066-o2067.  [CrossRef] [details]
Huang, K., Du, B.-X. & Liu, C.-L. (2011). Acta Cryst. E67, o2062.  [CrossRef] [details]
Kim, G. Y., Park, S.-K., Lee, D.-H. & Park, G. (2009). Acta Cryst. E65, o637.  [CSD] [CrossRef] [details]
Scholl, M., Ding, S., Lee, C. W. & Grubbs, R. H. (1999). Org. Lett. 1, 953-956.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o549  [ doi:10.1107/S1600536813006971 ]

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