1-Methyl-3-(4-vinyl­benz­yl)imidazolium hexa­fluoro­phosphate

Lu, X.-Y.; Sun, J.-F.; Zhang, L.; Chen, X.-T.

doi:10.1107/S1600536810000437

Volume 66
Part 2
Page o378
February 2010

Received 1 January 2010
Accepted 5 January 2010
Online 16 January 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.127
Data-to-parameter ratio = 17.7
Details

1-Methyl-3-(4-vinylbenzyl)imidazolium hexafluorophosphate

Xiang-Yong Lu,^a Jia-Feng Sun,^b Lin Zhang ^c and Xue-Tai Chen ^a ^*

^aState Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China,^bDepartment of Materials and Chemical Engineering, Taishan University, Taian 271021, People's Republic of China, and ^cResearch Centre of Laser Fusion, CAEP, Mianyang 621900, People's Republic of China
Correspondence e-mail: xtchen@netra.nju.edu.cn

In the title compound, C₁₃H₁₅N₂⁺·PF₆^-, the dihedral angle between the two aromatic rings is 85.48 (7)°. In the crystal, C-HF hydrogen bonds connect the imidazolium and hexafluorophosphate ions.

Related literature

For N-heterocyclic carbenes, see: Herrmann (2002). For the synthesis of the title compound, see: Kim et al. (2005). For a silver compound with 1-methyl-3-(4-vinylbenzyl)imidazol-2-ylidene, see: Lu et al. (2009).

Experimental

Crystal data

C₁₃H₁₅N₂⁺·PF₆^-
M_r = 344.24
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.482 (2) Å
b = 11.272 (3) Å
c = 12.556 (3) Å
V = 1483.4 (6) Å³
Z = 4
Mo K radiation
= 0.25 mm^-1
T = 298 K
0.32 × 0.29 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.925, T_max = 0.939
9185 measured reflections
3542 independent reflections
3407 reflections with I > 2(I)
R_int = 0.085

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.127
S = 1.03
3542 reflections
200 parameters
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.89 e Å^-3
Absolute structure: Flack (1983), 1484 Friedel pairs
Flack parameter: 0.05 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4F1ⁱ	0.93	2.36	3.266 (3)	164
C3-H3F6ⁱⁱ	0.93	2.25	3.044 (3)	143
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5162 ).

Acknowledgements

This work was supported by National Natural Science Foundation of China-NSAF (No. 10676012)

References

Bruker (2005). SMART, SAINT, SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Herrmann, W. A. (2002). Angew. Chem. Int. Ed. Engl. 41, 1290-1309.
Kim, J.-H., Kim, J.-W., Shokouhimehr, M. & Lee, Y.-S. (2005). J. Org. Chem. 70, 6714-6720.
Lu, X.-Y., CHen, F., Xu, W.-F. & Chen, X.-T. (2009). Inorg. Chim. Acta, 362, 5113-5116.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds