3-(3-Cyano-benz-yl)-1-methyl-1H-imidazol-3-ium hexa-fluoro-phosphate.

In the title compound, C(12)H(12)N(3) (+)·PF(6) (-), the hexa-fluoro-phosphate anion is disordered over two orientations with refined site occupancies of 0.8071 (17) and 0.1929 (17). The dihedral angle between the imidazole and benzene rings in the cation is 71.26 (7)°. In the crystal, the cations and anions are linked by C-H⋯F and C-H⋯N hydrogen bonds into a three-dimensional network.

Related literature

For details and applications of N-heterocyclic carbenes, see: Hermann et al. (1997 ▶); Wanzlick & Kleiner (1961 ▶); Hermann & Köcher (1997 ▶); Baker et al. (2007 ▶); Gade & Laponnaz (2007 ▶); Özdemir et al. (2005 ▶); Köcher & Hermann (1997 ▶); Cetinkaya et al. (1997 ▶). For a related structure, see: Haque et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C12H12N3 +·F6P−

M = 343.22

Triclinic,

a = 5.9782 (1) Å

b = 8.7920 (1) Å

c = 14.1028 (2) Å

α = 77.975 (1)°

β = 83.279 (1)°

γ = 86.635 (1)°

V = 719.55 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.43 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.897, T max = 0.949

14376 measured reflections

5233 independent reflections

4485 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.04

5233 reflections

246 parameters

21 restraints

H-atom parameters constrained

Δρmax = 0.91 e Å−3

Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001882/hb6605sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001882/hb6605Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001882/hb6605Isup3.cml

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

C12H12N3+·F6P−	Z = 2
Mr = 343.22	F(000) = 348
Triclinic, P1	Dx = 1.584 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9782 (1) Å	Cell parameters from 6359 reflections
b = 8.7920 (1) Å	θ = 2.5–32.7°
c = 14.1028 (2) Å	µ = 0.26 mm−1
α = 77.975 (1)°	T = 100 K
β = 83.279 (1)°	Block, colourless
γ = 86.635 (1)°	0.43 × 0.24 × 0.21 mm
V = 719.55 (2) Å3

Bruker SMART APEXII CCD diffractometer	5233 independent reflections
Radiation source: fine-focus sealed tube	4485 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 32.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.897, Tmax = 0.949	k = −13→13
14376 measured reflections	l = −21→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.372P] where P = (Fo2 + 2Fc2)/3
5233 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.91 e Å−3
21 restraints	Δρmin = −0.64 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
P1	0.0915 (2)	0.73349 (10)	0.16370 (8)	0.0173 (2)	0.8071 (17)
F1	0.3566 (2)	0.7033 (2)	0.15625 (12)	0.0487 (4)	0.8071 (17)
F2	0.1025 (4)	0.8343 (3)	0.05737 (16)	0.0487 (6)	0.8071 (17)
F3	−0.1762 (2)	0.75757 (17)	0.17710 (10)	0.0374 (3)	0.8071 (17)
F4	0.0797 (3)	0.6287 (2)	0.27361 (12)	0.0451 (4)	0.8071 (17)
F5	0.0591 (2)	0.57833 (15)	0.12519 (12)	0.0465 (4)	0.8071 (17)
F6	0.1151 (3)	0.88412 (15)	0.20813 (11)	0.0484 (4)	0.8071 (17)
P1X	0.0958 (11)	0.7363 (8)	0.1577 (5)	0.045 (2)	0.1929 (17)
F1X	0.3348 (10)	0.8099 (9)	0.1558 (4)	0.0486 (16)	0.1929 (17)
F2X	0.0465 (16)	0.8713 (10)	0.0645 (7)	0.0324 (16)	0.1929 (17)
F3X	−0.1326 (12)	0.6656 (11)	0.1492 (5)	0.077 (3)	0.1929 (17)
F4X	0.1509 (10)	0.6010 (6)	0.2425 (4)	0.0288 (12)	0.1929 (17)
F5X	0.2115 (10)	0.6342 (6)	0.0790 (5)	0.0465 (4)	0.1929 (17)
F6X	−0.0153 (13)	0.8381 (7)	0.2262 (5)	0.0484 (4)	0.1929 (17)
N1	0.46336 (19)	0.22118 (13)	0.12431 (7)	0.0216 (2)
N2	0.6288 (2)	0.30531 (13)	0.23067 (8)	0.0233 (2)
N3	0.8071 (2)	−0.08439 (15)	0.65425 (9)	0.0290 (2)
C1	0.4607 (2)	0.33312 (14)	0.17476 (9)	0.0229 (2)
H1A	0.3558	0.4190	0.1715	0.027*
C2	0.6385 (2)	0.11742 (16)	0.14906 (9)	0.0267 (3)
H2A	0.6791	0.0262	0.1240	0.032*
C3	0.7419 (2)	0.16950 (17)	0.21571 (9)	0.0270 (3)
H3A	0.8686	0.1217	0.2465	0.032*
C4	0.6750 (3)	0.39959 (17)	0.30071 (10)	0.0312 (3)
H4A	0.6125	0.5067	0.2803	0.037*
H4B	0.8399	0.4054	0.3004	0.037*
C5	0.5724 (2)	0.33138 (14)	0.40301 (9)	0.0238 (2)
C6	0.3613 (3)	0.38393 (16)	0.43888 (10)	0.0278 (3)
H6A	0.2810	0.4643	0.3991	0.033*
C7	0.2671 (2)	0.31960 (17)	0.53257 (11)	0.0288 (3)
H7A	0.1238	0.3572	0.5565	0.035*
C8	0.3807 (2)	0.20105 (16)	0.59146 (10)	0.0253 (3)
H8A	0.3163	0.1570	0.6554	0.030*
C9	0.5913 (2)	0.14774 (15)	0.55501 (9)	0.02253 (17)
C10	0.6883 (2)	0.21320 (15)	0.46148 (9)	0.0222 (2)
H10A	0.8329	0.1771	0.4379	0.027*
C11	0.3054 (3)	0.21229 (18)	0.05341 (10)	0.0303 (3)
H11A	0.1951	0.2996	0.0509	0.045*
H11B	0.2269	0.1141	0.0732	0.045*
H11C	0.3889	0.2172	−0.0112	0.045*
C12	0.7105 (2)	0.01965 (15)	0.61205 (9)	0.02253 (17)

	U11	U22	U33	U12	U13	U23
P1	0.0196 (5)	0.0133 (3)	0.0188 (3)	0.0025 (3)	−0.0025 (3)	−0.0035 (3)
F1	0.0187 (5)	0.0593 (9)	0.0658 (10)	−0.0012 (6)	0.0014 (5)	−0.0109 (8)
F2	0.0589 (15)	0.0616 (16)	0.0208 (7)	−0.0189 (10)	−0.0030 (8)	0.0067 (8)
F3	0.0226 (5)	0.0446 (7)	0.0422 (7)	0.0100 (5)	−0.0036 (5)	−0.0058 (6)
F4	0.0442 (9)	0.0523 (10)	0.0318 (8)	−0.0136 (7)	−0.0165 (6)	0.0179 (7)
F5	0.0475 (8)	0.0333 (6)	0.0690 (9)	0.0102 (5)	−0.0183 (7)	−0.0302 (6)
F6	0.0702 (10)	0.0290 (6)	0.0559 (8)	0.0030 (6)	−0.0275 (8)	−0.0211 (6)
P1X	0.019 (3)	0.053 (4)	0.058 (4)	0.001 (2)	−0.007 (2)	0.000 (3)
F1X	0.035 (3)	0.060 (4)	0.047 (3)	−0.026 (3)	−0.014 (2)	0.010 (3)
F2X	0.036 (4)	0.023 (3)	0.028 (3)	0.010 (2)	0.006 (2)	0.008 (2)
F3X	0.047 (4)	0.112 (7)	0.055 (4)	−0.054 (5)	−0.038 (3)	0.056 (5)
F4X	0.039 (3)	0.027 (2)	0.015 (2)	0.012 (2)	−0.0012 (18)	0.0023 (17)
F5X	0.0475 (8)	0.0333 (6)	0.0690 (9)	0.0102 (5)	−0.0183 (7)	−0.0302 (6)
F6X	0.0702 (10)	0.0290 (6)	0.0559 (8)	0.0030 (6)	−0.0275 (8)	−0.0211 (6)
N1	0.0237 (5)	0.0234 (5)	0.0160 (4)	0.0022 (4)	−0.0016 (4)	−0.0014 (4)
N2	0.0265 (5)	0.0237 (5)	0.0181 (4)	−0.0015 (4)	−0.0018 (4)	−0.0006 (4)
N3	0.0273 (6)	0.0320 (6)	0.0274 (5)	0.0024 (5)	−0.0061 (4)	−0.0048 (5)
C1	0.0261 (6)	0.0206 (5)	0.0200 (5)	0.0030 (4)	−0.0013 (4)	−0.0012 (4)
C2	0.0310 (6)	0.0268 (6)	0.0196 (5)	0.0097 (5)	0.0008 (5)	−0.0035 (4)
C3	0.0251 (6)	0.0329 (6)	0.0198 (5)	0.0077 (5)	−0.0013 (4)	−0.0011 (5)
C4	0.0437 (8)	0.0280 (6)	0.0221 (6)	−0.0134 (6)	−0.0048 (5)	−0.0014 (5)
C5	0.0313 (6)	0.0211 (5)	0.0203 (5)	−0.0053 (5)	−0.0054 (5)	−0.0045 (4)
C6	0.0348 (7)	0.0232 (5)	0.0273 (6)	0.0041 (5)	−0.0112 (5)	−0.0068 (5)
C7	0.0285 (6)	0.0296 (6)	0.0297 (6)	0.0070 (5)	−0.0034 (5)	−0.0111 (5)
C8	0.0268 (6)	0.0275 (6)	0.0217 (5)	0.0018 (5)	−0.0006 (5)	−0.0074 (5)
C9	0.0234 (4)	0.0245 (4)	0.0208 (4)	−0.0005 (3)	−0.0034 (3)	−0.0066 (3)
C10	0.0222 (5)	0.0242 (5)	0.0213 (5)	−0.0022 (4)	−0.0029 (4)	−0.0067 (4)
C11	0.0322 (7)	0.0357 (7)	0.0237 (6)	−0.0039 (6)	−0.0067 (5)	−0.0046 (5)
C12	0.0234 (4)	0.0245 (4)	0.0208 (4)	−0.0005 (3)	−0.0034 (3)	−0.0066 (3)

P1—F2	1.571 (2)	C2—C3	1.351 (2)
P1—F1	1.5860 (17)	C2—H2A	0.9500
P1—F3	1.5964 (17)	C3—H3A	0.9500
P1—F6	1.5983 (15)	C4—C5	1.5141 (19)
P1—F5	1.5993 (14)	C4—H4A	0.9900
P1—F4	1.6257 (18)	C4—H4B	0.9900
P1X—F6X	1.523 (8)	C5—C10	1.3899 (18)
P1X—F4X	1.552 (8)	C5—C6	1.394 (2)
P1X—F3X	1.560 (8)	C6—C7	1.391 (2)
P1X—F1X	1.598 (8)	C6—H6A	0.9500
P1X—F2X	1.619 (10)	C7—C8	1.3875 (19)
P1X—F5X	1.637 (8)	C7—H7A	0.9500
N1—C1	1.3275 (17)	C8—C9	1.3959 (18)
N1—C2	1.3751 (17)	C8—H8A	0.9500
N1—C11	1.4695 (18)	C9—C10	1.3970 (18)
N2—C1	1.3298 (17)	C9—C12	1.4444 (18)
N2—C3	1.3799 (17)	C10—H10A	0.9500
N2—C4	1.4733 (18)	C11—H11A	0.9800
N3—C12	1.1471 (18)	C11—H11B	0.9800
C1—H1A	0.9500	C11—H11C	0.9800
F2—P1—F1	92.46 (13)	N2—C1—H1A	125.6
F2—P1—F3	90.74 (12)	C3—C2—N1	107.16 (12)
F1—P1—F3	176.79 (11)	C3—C2—H2A	126.4
F2—P1—F6	91.41 (12)	N1—C2—H2A	126.4
F1—P1—F6	90.49 (11)	C2—C3—N2	107.07 (12)
F3—P1—F6	89.64 (10)	C2—C3—H3A	126.5
F2—P1—F5	91.54 (13)	N2—C3—H3A	126.5
F1—P1—F5	91.14 (10)	N2—C4—C5	111.59 (11)
F3—P1—F5	88.56 (10)	N2—C4—H4A	109.3
F6—P1—F5	176.57 (12)	C5—C4—H4A	109.3
F2—P1—F4	179.81 (15)	N2—C4—H4B	109.3
F1—P1—F4	87.62 (10)	C5—C4—H4B	109.3
F3—P1—F4	89.18 (10)	H4A—C4—H4B	108.0
F6—P1—F4	88.76 (10)	C10—C5—C6	119.47 (12)
F5—P1—F4	88.29 (10)	C10—C5—C4	119.72 (13)
F6X—P1X—F4X	93.3 (5)	C6—C5—C4	120.81 (13)
F6X—P1X—F3X	92.6 (6)	C7—C6—C5	120.48 (12)
F4X—P1X—F3X	92.2 (5)	C7—C6—H6A	119.8
F6X—P1X—F1X	91.3 (5)	C5—C6—H6A	119.8
F4X—P1X—F1X	91.2 (5)	C8—C7—C6	120.60 (13)
F3X—P1X—F1X	174.7 (6)	C8—C7—H7A	119.7
F6X—P1X—F2X	90.2 (5)	C6—C7—H7A	119.7
F4X—P1X—F2X	176.5 (6)	C7—C8—C9	118.78 (12)
F3X—P1X—F2X	87.9 (6)	C7—C8—H8A	120.6
F1X—P1X—F2X	88.5 (6)	C9—C8—H8A	120.6
F6X—P1X—F5X	176.9 (6)	C8—C9—C10	120.97 (12)
F4X—P1X—F5X	89.9 (4)	C8—C9—C12	120.61 (12)
F3X—P1X—F5X	87.1 (6)	C10—C9—C12	118.39 (12)
F1X—P1X—F5X	88.8 (5)	C5—C10—C9	119.70 (12)
F2X—P1X—F5X	86.6 (5)	C5—C10—H10A	120.2
C1—N1—C2	108.59 (11)	C9—C10—H10A	120.2
C1—N1—C11	125.08 (11)	N1—C11—H11A	109.5
C2—N1—C11	126.33 (12)	N1—C11—H11B	109.5
C1—N2—C3	108.33 (11)	H11A—C11—H11B	109.5
C1—N2—C4	125.08 (12)	N1—C11—H11C	109.5
C3—N2—C4	126.49 (12)	H11A—C11—H11C	109.5
N1—C1—N2	108.85 (11)	H11B—C11—H11C	109.5
N1—C1—H1A	125.6	N3—C12—C9	177.42 (14)
C2—N1—C1—N2	0.34 (14)	N2—C4—C5—C6	−95.13 (16)
C11—N1—C1—N2	−179.13 (12)	C10—C5—C6—C7	0.3 (2)
C3—N2—C1—N1	−0.48 (14)	C4—C5—C6—C7	179.33 (13)
C4—N2—C1—N1	−177.01 (11)	C5—C6—C7—C8	−0.7 (2)
C1—N1—C2—C3	−0.07 (15)	C6—C7—C8—C9	0.1 (2)
C11—N1—C2—C3	179.40 (12)	C7—C8—C9—C10	0.8 (2)
N1—C2—C3—N2	−0.22 (15)	C7—C8—C9—C12	−177.06 (13)
C1—N2—C3—C2	0.43 (15)	C6—C5—C10—C9	0.52 (19)
C4—N2—C3—C2	176.90 (12)	C4—C5—C10—C9	−178.47 (12)
C1—N2—C4—C5	95.87 (16)	C8—C9—C10—C5	−1.09 (19)
C3—N2—C4—C5	−80.04 (18)	C12—C9—C10—C5	176.79 (12)
N2—C4—C5—C10	83.85 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F1	0.95	2.46	3.240 (2)	139
C1—H1A···F5	0.95	2.27	3.1715 (18)	159
C2—H2A···F3i	0.95	2.46	3.250 (2)	140
C3—H3A···N3ii	0.95	2.49	3.3970 (19)	160
C4—H4B···F4iii	0.99	2.44	3.177 (2)	131
C6—H6A···F4	0.95	2.43	3.361 (2)	167
C10—H10A···N3ii	0.95	2.56	3.5019 (17)	170
C11—H11B···F6iv	0.98	2.53	3.400 (2)	148
C11—H11C···F1v	0.98	2.41	3.353 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯F1	0.95	2.46	3.240 (2)	139
C1—H1A⋯F5	0.95	2.27	3.1715 (18)	159
C2—H2A⋯F3i	0.95	2.46	3.250 (2)	140
C3—H3A⋯N3ii	0.95	2.49	3.3970 (19)	160
C4—H4B⋯F4iii	0.99	2.44	3.177 (2)	131
C6—H6A⋯F4	0.95	2.43	3.361 (2)	167
C10—H10A⋯N3ii	0.95	2.56	3.5019 (17)	170
C11—H11B⋯F6iv	0.98	2.53	3.400 (2)	148
C11—H11C⋯F1v	0.98	2.41	3.353 (2)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .