1-Methyl-3-(4-vinyl-benz-yl)imidazolium hexa-fluoro-phosphate.

In the title compound, C(13)H(15)N(2) (+)·PF(6) (-), the dihedral angle between the two aromatic rings is 85.48 (7)°. In the crystal, C-H⋯F hydrogen bonds connect the imidazolium and hexa-fluoro-phosphate 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 = 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

Δρmax = 0.65 e Å−3

Δρmin = −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.

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

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

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

C13H15N2+·PF6−	F(000) = 704
Mr = 344.24	Dx = 1.541 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6513 reflections
a = 10.482 (2) Å	θ = 2.4–28.3°
b = 11.272 (3) Å	µ = 0.25 mm−1
c = 12.556 (3) Å	T = 298 K
V = 1483.4 (6) Å3	Block, colorless
Z = 4	0.32 × 0.29 × 0.26 mm

Bruker SMART CCD area-detector diffractometer	3542 independent reflections
Radiation source: fine-focus sealed tube	3407 reflections with I > 2σ(I)
graphite	Rint = 0.085
phi and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→11
Tmin = 0.925, Tmax = 0.939	k = −14→14
9185 measured reflections	l = −16→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0549P)2 + 1.5672P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3542 reflections	Δρmax = 0.65 e Å−3
200 parameters	Δρmin = −0.89 e Å−3
0 restraints	Absolute structure: Flack (1983), 1484 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (13)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.8710 (3)	0.2998 (3)	0.0944 (2)	0.0351 (7)
H1A	0.9248	0.2527	0.1396	0.053*
H1B	0.9017	0.3800	0.0931	0.053*
H1C	0.8722	0.2679	0.0235	0.053*
C2	0.6394 (3)	0.3609 (2)	0.0958 (2)	0.0283 (6)
H2	0.6415	0.4128	0.0382	0.034*
C3	0.5369 (3)	0.3342 (2)	0.1548 (2)	0.0249 (5)
H3	0.4549	0.3641	0.1460	0.030*
C4	0.6999 (3)	0.2335 (2)	0.21741 (19)	0.0204 (5)
H4	0.7497	0.1826	0.2583	0.025*
C5	0.4948 (3)	0.2031 (3)	0.3150 (2)	0.0228 (5)
H5A	0.4678	0.2657	0.3630	0.027*
H5B	0.5440	0.1461	0.3558	0.027*
C6	0.3787 (2)	0.1426 (2)	0.26935 (19)	0.0192 (5)
C7	0.2587 (3)	0.1657 (2)	0.3101 (2)	0.0236 (5)
H7	0.2489	0.2225	0.3632	0.028*
C8	0.1529 (3)	0.1050 (3)	0.2724 (2)	0.0234 (5)
H8	0.0729	0.1216	0.3008	0.028*
C9	0.1643 (2)	0.0194 (2)	0.19242 (19)	0.0191 (5)
C10	0.2861 (2)	−0.0017 (2)	0.14997 (18)	0.0190 (5)
H10	0.2960	−0.0569	0.0956	0.023*
C11	0.3914 (2)	0.0584 (2)	0.1878 (2)	0.0199 (5)
H11	0.4714	0.0429	0.1590	0.024*
C12	0.0501 (3)	−0.0449 (2)	0.1563 (2)	0.0230 (5)
H12	−0.0282	−0.0177	0.1812	0.028*
C13	0.0480 (3)	−0.1377 (3)	0.0917 (2)	0.0260 (5)
H13A	0.1239	−0.1681	0.0647	0.031*
H13B	−0.0294	−0.1725	0.0733	0.031*
F1	0.67298 (19)	0.98396 (17)	0.85265 (12)	0.0364 (4)
F2	0.75104 (15)	0.85036 (13)	0.96990 (13)	0.0245 (3)
F3	0.54994 (15)	0.92291 (15)	0.99001 (14)	0.0297 (4)
F4	0.70480 (17)	0.97546 (17)	1.10592 (12)	0.0305 (4)
F5	0.62797 (17)	1.11050 (14)	0.98847 (14)	0.0309 (4)
F6	0.82848 (16)	1.03763 (16)	0.96874 (17)	0.0359 (4)
N1	0.7402 (2)	0.2980 (2)	0.13540 (17)	0.0247 (5)
N2	0.5760 (2)	0.25420 (19)	0.23092 (17)	0.0191 (4)
P1	0.68904 (6)	0.98115 (6)	0.97936 (5)	0.01785 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0343 (15)	0.0449 (17)	0.0259 (13)	−0.0109 (14)	0.0098 (12)	−0.0043 (13)
C2	0.0468 (16)	0.0210 (12)	0.0170 (11)	−0.0073 (12)	−0.0057 (12)	0.0022 (10)
C3	0.0371 (14)	0.0197 (12)	0.0179 (11)	0.0005 (11)	−0.0092 (11)	0.0012 (9)
C4	0.0257 (12)	0.0206 (12)	0.0149 (10)	−0.0049 (10)	−0.0021 (9)	−0.0001 (8)
C5	0.0254 (12)	0.0298 (13)	0.0130 (10)	−0.0031 (11)	−0.0006 (10)	0.0008 (10)
C6	0.0227 (11)	0.0222 (12)	0.0128 (10)	0.0002 (10)	−0.0020 (9)	0.0007 (9)
C7	0.0295 (13)	0.0235 (12)	0.0180 (10)	0.0022 (11)	0.0003 (10)	−0.0052 (10)
C8	0.0218 (12)	0.0274 (13)	0.0212 (11)	0.0045 (10)	0.0049 (10)	−0.0042 (10)
C9	0.0244 (12)	0.0188 (11)	0.0142 (9)	0.0014 (9)	−0.0009 (9)	0.0024 (9)
C10	0.0266 (12)	0.0191 (12)	0.0114 (9)	0.0024 (9)	0.0013 (9)	−0.0005 (8)
C11	0.0197 (11)	0.0246 (12)	0.0154 (10)	0.0046 (10)	0.0016 (9)	0.0024 (9)
C12	0.0210 (11)	0.0288 (13)	0.0192 (11)	−0.0004 (10)	0.0015 (10)	0.0016 (10)
C13	0.0262 (12)	0.0297 (14)	0.0223 (12)	−0.0030 (11)	−0.0030 (10)	−0.0017 (11)
F1	0.0519 (11)	0.0436 (10)	0.0136 (7)	0.0145 (9)	−0.0002 (7)	−0.0030 (7)
F2	0.0282 (8)	0.0221 (7)	0.0234 (7)	0.0037 (6)	−0.0019 (7)	−0.0001 (6)
F3	0.0214 (7)	0.0343 (9)	0.0336 (9)	−0.0042 (6)	−0.0004 (7)	0.0058 (7)
F4	0.0384 (9)	0.0382 (9)	0.0149 (7)	0.0029 (8)	0.0031 (6)	0.0037 (6)
F5	0.0343 (8)	0.0240 (8)	0.0343 (9)	0.0064 (7)	0.0045 (8)	0.0040 (7)
F6	0.0238 (8)	0.0317 (9)	0.0521 (11)	−0.0055 (7)	−0.0052 (8)	−0.0098 (8)
N1	0.0333 (12)	0.0256 (11)	0.0153 (9)	−0.0103 (10)	0.0007 (9)	−0.0018 (9)
N2	0.0234 (10)	0.0191 (10)	0.0147 (9)	−0.0025 (8)	−0.0026 (8)	0.0011 (8)
P1	0.0191 (3)	0.0204 (3)	0.0141 (3)	0.0009 (2)	−0.0008 (2)	0.0002 (2)

C1—N1	1.464 (4)	C7—H7	0.9300
C1—H1A	0.9600	C8—C9	1.398 (4)
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—C10	1.404 (3)
C2—C3	1.339 (4)	C9—C12	1.471 (4)
C2—N1	1.367 (4)	C10—C11	1.379 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—N2	1.377 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.324 (4)
C4—N1	1.330 (3)	C12—H12	0.9300
C4—N2	1.330 (3)	C13—H13A	0.9300
C4—H4	0.9300	C13—H13B	0.9300
C5—N2	1.473 (3)	F1—P1	1.6001 (17)
C5—C6	1.508 (4)	F2—P1	1.6156 (16)
C5—H5A	0.9700	F3—P1	1.6046 (17)
C5—H5B	0.9700	F4—P1	1.5988 (16)
C6—C7	1.383 (4)	F5—P1	1.5964 (17)
C6—C11	1.403 (4)	F6—P1	1.5998 (18)
C7—C8	1.387 (4)
N1—C1—H1A	109.5	C11—C10—C9	120.9 (2)
N1—C1—H1B	109.5	C11—C10—H10	119.5
H1A—C1—H1B	109.5	C9—C10—H10	119.5
N1—C1—H1C	109.5	C10—C11—C6	120.5 (2)
H1A—C1—H1C	109.5	C10—C11—H11	119.7
H1B—C1—H1C	109.5	C6—C11—H11	119.7
C3—C2—N1	107.6 (2)	C13—C12—C9	126.3 (3)
C3—C2—H2	126.2	C13—C12—H12	116.9
N1—C2—H2	126.2	C9—C12—H12	116.9
C2—C3—N2	107.0 (3)	C12—C13—H13A	120.0
C2—C3—H3	126.5	C12—C13—H13B	120.0
N2—C3—H3	126.5	H13A—C13—H13B	120.0
N1—C4—N2	108.3 (2)	C4—N1—C2	108.6 (2)
N1—C4—H4	125.9	C4—N1—C1	125.3 (3)
N2—C4—H4	125.9	C2—N1—C1	126.0 (3)
N2—C5—C6	111.8 (2)	C4—N2—C3	108.5 (2)
N2—C5—H5A	109.3	C4—N2—C5	125.9 (2)
C6—C5—H5A	109.3	C3—N2—C5	125.6 (2)
N2—C5—H5B	109.3	F5—P1—F4	90.40 (10)
C6—C5—H5B	109.3	F5—P1—F6	90.51 (10)
H5A—C5—H5B	107.9	F4—P1—F6	90.25 (10)
C7—C6—C11	118.9 (2)	F5—P1—F1	90.63 (10)
C7—C6—C5	120.6 (2)	F4—P1—F1	178.83 (11)
C11—C6—C5	120.5 (2)	F6—P1—F1	90.30 (11)
C6—C7—C8	120.6 (2)	F5—P1—F3	90.19 (10)
C6—C7—H7	119.7	F4—P1—F3	89.69 (10)
C8—C7—H7	119.7	F6—P1—F3	179.30 (10)
C7—C8—C9	121.2 (2)	F1—P1—F3	89.74 (10)
C7—C8—H8	119.4	F5—P1—F2	179.86 (11)
C9—C8—H8	119.4	F4—P1—F2	89.71 (9)
C8—C9—C10	117.8 (2)	F6—P1—F2	89.39 (9)
C8—C9—C12	119.5 (2)	F1—P1—F2	89.27 (9)
C10—C9—C12	122.7 (2)	F3—P1—F2	89.91 (9)

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

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

Symmetry codes: (i) ; (ii) .