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

Xiang-Yong Lu; Jia-Feng Sun; Lin Zhang; Xue-Tai Chen

doi:10.1107/S1600536810000437

. 2010 Jan 16;66(Pt 2):o378. doi: 10.1107/S1600536810000437

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

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

PMCID: PMC2979844 PMID: 21579800

Abstract

In the title compound, C₁₃H₁₅N₂ ⁺·PF₆ ⁻, the dihedral angle between the two aromatic rings is 85.48 (7)°. In the crystal, C—H⋯F 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,
a = 10.482 (2) Å
b = 11.272 (3) Å
c = 12.556 (3) Å
V = 1483.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.085

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.127
S = 1.03
3542 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.89 e Å⁻³
Absolute structure: Flack (1983 ▶), 1484 Friedel pairs
Flack parameter: 0.05 (13)

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000437/bt5162sup1.cif

e-66-0o378-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000437/bt5162Isup2.hkl

e-66-0o378-Isup2.hkl^{(173.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯F1ⁱ	0.93	2.36	3.266 (3)	164
C3—H3⋯F6ⁱⁱ	0.93	2.25	3.044 (3)	143

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

N-heterocyclic carbenes have attracted great attention as they can act as efficient supporting ligands in organometallic chemistry and homogeneous catalysis (Herrmann, 2002). Imidazolium salts are the useful precusors of the N-heterocyclic carbenes. The silver compound with 1-methyl-3-(4-vinylbenzyl)imidazol-2-ylidene has been synthesized (Lu et al., 2009).

The structure of the title compound is shown in Fig. 1. The two aromatic rings enclose a dihedral angle of 85.48 (7)°. The hexafluorophosphate anions are linked to 1-methyl-3-(4-vinylbenzyl)imidazolium cations via C—H···F hydrogen bonds (Table 1 and Fig. 2). These interacions stabilize the crystal structure.

Experimental

1-Methyl-3-(4-vinylbenzyl)imidazolium chloride was synthesized according to the literature method (Kim et al., 2005). The resulting white solid (0.70 g, 3.00 mmol) was dissolved in acetone (30 ml) and then potassium hexafluorophosphate (1.38 g, 7.50 mmol) was added. The mixture was stirred at room temperature for 26 h and the solvent was removed under reduced pressure. The residue was then dissolved in distilled water and extracted with CH₂Cl₂. The white solid was abtained after the removal of solvent. Yield: 0.78 g (76%). Anal. Calcd for C₁₃H₁₅F₆N₂P: C,45.36; H, 4.39; N, 8.14. Found: C, 45.13; H, 4.03; N, 8.35. The elemental analyses were performed with Vario MICRO elemental analyzer.