1,3-Bis(6-methyl-pyridin-2-yl)-1H-imidazol-3-ium hexa-fluoro-phosphate.

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 ▶). For related structures, see: Huang et al. (2011 ▶); Grieco et al. (2011 ▶); Kim et al. (2009 ▶). For applications of N-heterocyclic carbenes in catalytic processes, see: Enders et al. (1996 ▶); Frenzel et al. (1999 ▶); Scholl et al. (1999 ▶).

Experimental

Crystal data

C17H19N4 +·PF6 −

M = 424.33

Triclinic,

a = 6.3839 (3) Å

b = 12.0353 (5) Å

c = 12.8006 (5) Å

α = 108.039 (2)°

β = 96.091 (2)°

γ = 100.593 (2)°

V = 905.12 (7) Å3

Z = 2

Mo Kα radiation

μ = 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 ▶) T min = 0.965, T max = 0.986

19206 measured reflections

3700 independent reflections

2898 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.133

S = 0.97

3700 reflections

269 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006971/ng5317sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006971/ng5317Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006971/ng5317Isup3.cml

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

C17H19N4+·PF6−	Z = 2
Mr = 424.33	F(000) = 436
Triclinic, P1	Dx = 1.557 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3839 (3) Å	Cell parameters from 3700 reflections
b = 12.0353 (5) Å	θ = 1.7–26.5°
c = 12.8006 (5) Å	µ = 0.22 mm−1
α = 108.039 (2)°	T = 100 K
β = 96.091 (2)°	Block, colorless
γ = 100.593 (2)°	0.16 × 0.07 × 0.07 mm
V = 905.12 (7) Å3

Bruker APEXII diffractometer	2898 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 26.5°, θmin = 1.7°
θ/2πhi scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→15
Tmin = 0.965, Tmax = 0.986	l = −16→16
19206 measured reflections	4 standard reflections every 10 min
3700 independent reflections	intensity decay: 0.0%

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3700 reflections	(Δ/σ)max < 0.001
269 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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
P1	0.02678 (7)	0.17116 (4)	0.22243 (4)	0.02100 (17)
F1	−0.20955 (18)	0.16206 (10)	0.25487 (10)	0.0319 (3)
F2	0.26436 (17)	0.18066 (10)	0.18965 (10)	0.0307 (3)
F3	0.09571 (18)	0.30854 (9)	0.30069 (11)	0.0335 (3)
F4	0.1109 (2)	0.13509 (11)	0.32678 (10)	0.0383 (3)
F5	−0.0381 (2)	0.03350 (11)	0.14681 (12)	0.0517 (4)
F6	−0.05468 (19)	0.21073 (14)	0.12030 (11)	0.0472 (4)
N1	0.4837 (2)	0.09220 (12)	0.78766 (12)	0.0161 (3)
N2	0.2781 (2)	0.42854 (12)	0.85867 (12)	0.0172 (3)
N3	0.5463 (2)	0.18196 (13)	0.59095 (12)	0.0178 (3)
N4	0.3855 (2)	0.21935 (12)	0.92229 (12)	0.0159 (3)
C1	0.3009 (3)	0.54548 (17)	0.73429 (16)	0.0246 (4)
H1A	0.3075	0.6315	0.7669	0.037*
H1B	0.2319	0.5167	0.6557	0.037*
H1C	0.4478	0.5319	0.7397	0.037*
C2	0.1717 (3)	0.47883 (15)	0.79610 (14)	0.0181 (4)
C3	−0.0512 (3)	0.46979 (15)	0.78953 (15)	0.0201 (4)
H3	−0.1230	0.5075	0.7462	0.025 (5)*
C4	−0.1665 (3)	0.40628 (16)	0.84576 (16)	0.0218 (4)
H4	−0.3181	0.3993	0.8416	0.027 (5)*
C5	−0.0567 (3)	0.35243 (15)	0.90892 (15)	0.0205 (4)
H5	−0.1320	0.3067	0.9477	0.023 (5)*
C6	0.1643 (3)	0.36706 (15)	0.91398 (14)	0.0173 (4)
C7	0.2937 (3)	0.31832 (16)	0.98693 (14)	0.0199 (4)
H7A	0.4132	0.3841	1.0371	0.032 (6)*
H7B	0.1998	0.2888	1.0340	0.023 (5)*
C8	0.3746 (3)	0.17802 (15)	0.81261 (14)	0.0162 (4)
H8	0.3008	0.2054	0.7604	0.017 (5)*
C9	0.5053 (3)	0.15701 (16)	0.96936 (15)	0.0194 (4)
H9	0.5382	0.1678	1.0465	0.033 (6)*
C10	0.5668 (3)	0.07800 (15)	0.88527 (15)	0.0189 (4)
H10	0.6517	0.0227	0.8920	0.030 (5)*
C11	0.5118 (3)	0.02583 (15)	0.67421 (14)	0.0187 (4)
H11A	0.3680	−0.0104	0.6259	0.028 (5)*
H11B	0.5827	−0.0401	0.6767	0.043 (7)*
C12	0.6464 (3)	0.10626 (15)	0.62463 (14)	0.0164 (4)
C13	0.8589 (3)	0.10113 (16)	0.61417 (15)	0.0198 (4)
H13	0.9250	0.0475	0.6396	0.021 (5)*
C14	0.9729 (3)	0.17597 (16)	0.56576 (15)	0.0210 (4)
H14	1.1185	0.1743	0.5573	0.020 (5)*
C15	0.8716 (3)	0.25257 (16)	0.53018 (15)	0.0199 (4)
H15	0.9460	0.3038	0.4960	0.022 (5)*
C16	0.6582 (3)	0.25440 (15)	0.54479 (14)	0.0185 (4)
C17	0.5434 (3)	0.33675 (18)	0.50650 (18)	0.0277 (4)
H17A	0.5198	0.3113	0.4248	0.042*
H17B	0.6318	0.4190	0.5378	0.042*
H17C	0.4035	0.3337	0.5319	0.042*

	U11	U22	U33	U12	U13	U23
P1	0.0187 (3)	0.0230 (3)	0.0248 (3)	0.0041 (2)	0.0065 (2)	0.0125 (2)
F1	0.0232 (6)	0.0308 (6)	0.0450 (7)	0.0050 (5)	0.0158 (5)	0.0147 (5)
F2	0.0196 (6)	0.0401 (7)	0.0371 (7)	0.0072 (5)	0.0100 (5)	0.0176 (5)
F3	0.0274 (6)	0.0206 (6)	0.0519 (8)	0.0073 (5)	0.0026 (5)	0.0117 (5)
F4	0.0493 (8)	0.0459 (8)	0.0417 (8)	0.0283 (6)	0.0193 (6)	0.0317 (6)
F5	0.0393 (8)	0.0334 (8)	0.0601 (10)	−0.0049 (6)	0.0220 (7)	−0.0123 (6)
F6	0.0257 (7)	0.0908 (11)	0.0386 (8)	0.0116 (7)	0.0034 (6)	0.0427 (8)
N1	0.0154 (7)	0.0146 (7)	0.0194 (8)	0.0032 (6)	0.0042 (6)	0.0073 (6)
N2	0.0157 (8)	0.0177 (7)	0.0187 (8)	0.0043 (6)	0.0038 (6)	0.0062 (6)
N3	0.0169 (8)	0.0183 (8)	0.0181 (8)	0.0037 (6)	0.0024 (6)	0.0062 (6)
N4	0.0135 (7)	0.0172 (7)	0.0188 (7)	0.0036 (6)	0.0030 (6)	0.0086 (6)
C1	0.0240 (10)	0.0272 (10)	0.0275 (10)	0.0082 (8)	0.0058 (8)	0.0142 (8)
C2	0.0203 (9)	0.0157 (8)	0.0171 (9)	0.0050 (7)	0.0031 (7)	0.0035 (7)
C3	0.0178 (9)	0.0170 (9)	0.0239 (9)	0.0054 (7)	0.0004 (7)	0.0047 (7)
C4	0.0139 (9)	0.0185 (9)	0.0292 (10)	0.0027 (7)	0.0031 (7)	0.0036 (8)
C5	0.0192 (9)	0.0164 (9)	0.0249 (10)	0.0027 (7)	0.0070 (7)	0.0052 (7)
C6	0.0185 (9)	0.0151 (8)	0.0182 (9)	0.0049 (7)	0.0044 (7)	0.0041 (7)
C7	0.0225 (10)	0.0211 (9)	0.0177 (9)	0.0076 (7)	0.0061 (7)	0.0066 (7)
C8	0.0133 (8)	0.0170 (8)	0.0190 (9)	0.0024 (7)	0.0016 (7)	0.0081 (7)
C9	0.0172 (9)	0.0235 (9)	0.0207 (9)	0.0045 (7)	0.0021 (7)	0.0124 (7)
C10	0.0158 (9)	0.0203 (9)	0.0246 (10)	0.0046 (7)	0.0032 (7)	0.0130 (8)
C11	0.0193 (9)	0.0177 (9)	0.0197 (9)	0.0062 (7)	0.0064 (7)	0.0048 (7)
C12	0.0169 (9)	0.0158 (8)	0.0141 (8)	0.0041 (7)	0.0007 (7)	0.0025 (7)
C13	0.0172 (9)	0.0211 (9)	0.0213 (9)	0.0054 (7)	0.0021 (7)	0.0075 (7)
C14	0.0147 (9)	0.0239 (9)	0.0229 (10)	0.0047 (7)	0.0037 (7)	0.0055 (8)
C15	0.0190 (9)	0.0220 (9)	0.0178 (9)	0.0013 (7)	0.0052 (7)	0.0067 (7)
C16	0.0188 (9)	0.0204 (9)	0.0151 (9)	0.0040 (7)	0.0024 (7)	0.0051 (7)
C17	0.0272 (11)	0.0284 (10)	0.0345 (11)	0.0087 (8)	0.0067 (9)	0.0186 (9)

P1—F5	1.5883 (13)	C4—H4	0.9500
P1—F6	1.5933 (12)	C5—C6	1.381 (2)
P1—F3	1.5951 (12)	C5—H5	0.9500
P1—F4	1.5980 (12)	C6—C7	1.501 (2)
P1—F1	1.6003 (12)	C7—H7A	0.9900
P1—F2	1.6095 (12)	C7—H7B	0.9900
N1—C8	1.327 (2)	C8—H8	0.9500
N1—C10	1.377 (2)	C9—C10	1.345 (3)
N1—C11	1.473 (2)	C9—H9	0.9500
N2—C2	1.343 (2)	C10—H10	0.9500
N2—C6	1.346 (2)	C11—C12	1.506 (3)
N3—C16	1.341 (2)	C11—H11A	0.9900
N3—C12	1.350 (2)	C11—H11B	0.9900
N4—C8	1.326 (2)	C12—C13	1.388 (2)
N4—C9	1.380 (2)	C13—C14	1.388 (3)
N4—C7	1.482 (2)	C13—H13	0.9500
C1—C2	1.496 (3)	C14—C15	1.376 (2)
C1—H1A	0.9800	C14—H14	0.9500
C1—H1B	0.9800	C15—C16	1.398 (2)
C1—H1C	0.9800	C15—H15	0.9500
C2—C3	1.399 (2)	C16—C17	1.501 (2)
C3—C4	1.375 (3)	C17—H17A	0.9800
C3—H3	0.9500	C17—H17B	0.9800
C4—C5	1.391 (2)	C17—H17C	0.9800
F5—P1—F6	91.57 (8)	C5—C6—C7	120.87 (16)
F5—P1—F3	178.51 (7)	N4—C7—C6	112.82 (14)
F6—P1—F3	89.86 (7)	N4—C7—H7A	109.0
F5—P1—F4	89.92 (8)	C6—C7—H7A	109.0
F6—P1—F4	178.50 (8)	N4—C7—H7B	109.0
F3—P1—F4	88.65 (7)	C6—C7—H7B	109.0
F5—P1—F1	90.45 (7)	H7A—C7—H7B	107.8
F6—P1—F1	89.57 (6)	N4—C8—N1	108.81 (14)
F3—P1—F1	89.98 (6)	N4—C8—H8	125.6
F4—P1—F1	90.59 (7)	N1—C8—H8	125.6
F5—P1—F2	89.65 (7)	C10—C9—N4	106.99 (15)
F6—P1—F2	90.28 (6)	C10—C9—H9	126.5
F3—P1—F2	89.92 (6)	N4—C9—H9	126.5
F4—P1—F2	89.57 (6)	C9—C10—N1	107.26 (15)
F1—P1—F2	179.82 (6)	C9—C10—H10	126.4
C8—N1—C10	108.43 (15)	N1—C10—H10	126.4
C8—N1—C11	124.97 (14)	N1—C11—C12	111.69 (14)
C10—N1—C11	126.59 (14)	N1—C11—H11A	109.3
C2—N2—C6	118.40 (15)	C12—C11—H11A	109.3
C16—N3—C12	118.01 (15)	N1—C11—H11B	109.3
C8—N4—C9	108.50 (14)	C12—C11—H11B	109.3
C8—N4—C7	127.20 (14)	H11A—C11—H11B	107.9
C9—N4—C7	124.26 (15)	N3—C12—C13	122.89 (16)
C2—C1—H1A	109.5	N3—C12—C11	115.65 (15)
C2—C1—H1B	109.5	C13—C12—C11	121.46 (15)
H1A—C1—H1B	109.5	C14—C13—C12	118.66 (16)
C2—C1—H1C	109.5	C14—C13—H13	120.7
H1A—C1—H1C	109.5	C12—C13—H13	120.7
H1B—C1—H1C	109.5	C15—C14—C13	118.86 (17)
N2—C2—C3	121.23 (17)	C15—C14—H14	120.6
N2—C2—C1	117.52 (16)	C13—C14—H14	120.6
C3—C2—C1	121.25 (16)	C14—C15—C16	119.50 (17)
C4—C3—C2	120.01 (17)	C14—C15—H15	120.2
C4—C3—H3	120.0	C16—C15—H15	120.2
C2—C3—H3	120.0	N3—C16—C15	122.06 (16)
C3—C4—C5	118.67 (17)	N3—C16—C17	117.27 (16)
C3—C4—H4	120.7	C15—C16—C17	120.66 (16)
C5—C4—H4	120.7	C16—C17—H17A	109.5
C6—C5—C4	118.44 (17)	C16—C17—H17B	109.5
C6—C5—H5	120.8	H17A—C17—H17B	109.5
C4—C5—H5	120.8	C16—C17—H17C	109.5
N2—C6—C5	123.21 (16)	H17A—C17—H17C	109.5
N2—C6—C7	115.87 (15)	H17B—C17—H17C	109.5

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

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) ; (ii) ; (iii) ; (iv) .