3,3'-Dimethyl-1,1'-(propane-1,3-di-yl)diimidazol-1-ium bis(hexafluoro-phosphate).

In the title compound, C(11)H(18)N(4) (2+)·2PF(6) (-), the dihedral angle between the two planar imidozlium rings is 6.1 (2)°. Both [PF(6)](-) anions are disordered [occupancies 0.65 (2):0.35 (2) and 0.59 (5):0.41 (5)]. The crystal packing is stabilized by inter-molecular C-H⋯F hydrogen bonds which link two mol-ecules, forming centrosymmetric dimers.

Related literature

For applications of dicationic ionic liquids, see: Jared et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶); Matsumoto & Hagiwara (2007 ▶).

Experimental

Crystal data

C11H18N4 2+·2PF6 −

M = 496.23

Triclinic,

a = 8.2300 (16) Å

b = 10.192 (2) Å

c = 12.856 (3) Å

α = 107.99 (3)°

β = 104.50 (3)°

γ = 96.35 (3)°

V = 972.1 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 298 (2) K

0.30 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.905, T max = 0.935

3484 measured reflections

3484 independent reflections

2637 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.179

S = 0.97

3484 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global, x1. DOI: 10.1107/S160053680803746X/rn2047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803746X/rn2047Isup2.hkl

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

C11H18N42+·2PF6–	Z = 2
Mr = 496.23	F000 = 500
Triclinic, P1	Dx = 1.695 Mg m−3
Hall symbol: -P 1	Melting point: 414 K
a = 8.2300 (16) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.192 (2) Å	Cell parameters from 25 reflections
c = 12.856 (3) Å	θ = 10–12º
α = 107.99 (3)º	µ = 0.34 mm−1
β = 104.50 (3)º	T = 298 (2) K
γ = 96.35 (3)º	Block, colorless
V = 972.1 (5) Å3	0.30 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.8º
T = 298(2) K	h = −9→9
ω/2θ scans	k = −12→11
Absorption correction: ψ scan(North et al., 1968)	l = 0→15
Tmin = 0.905, Tmax = 0.935	3 standard reflections
3484 measured reflections	every 200 reflections
3484 independent reflections	intensity decay: none
2637 reflections with I > 2σ(I)

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.180	w = 1/[σ2(Fo2) + (0.1017P)2 + 1.1631P] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.008
3484 reflections	Δρmax = 0.30 e Å−3
372 parameters	Δρmin = −0.48 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.17011 (11)	0.74314 (10)	0.95610 (8)	0.0542 (3)
F1	0.2940 (19)	0.681 (2)	1.0328 (16)	0.131 (5)	0.65 (2)
F2	0.0282 (10)	0.752 (2)	0.8566 (8)	0.109 (4)	0.65 (2)
F3	0.2002 (14)	0.6372 (10)	0.8485 (8)	0.108 (4)	0.65 (2)
F4	0.114 (3)	0.871 (3)	1.042 (3)	0.104 (9)	0.35 (2)
F5	0.0358 (18)	0.6358 (16)	0.9717 (13)	0.105 (4)	0.65 (2)
F6	0.3276 (19)	0.8550 (14)	0.9610 (14)	0.089 (4)	0.65 (2)
F1'	0.309 (3)	0.753 (3)	1.0618 (19)	0.116 (7)	0.35 (2)
F2'	0.072 (3)	0.838 (3)	0.894 (2)	0.107 (6)	0.35 (2)
F3'	0.229 (3)	0.618 (2)	0.880 (3)	0.154 (13)	0.35 (2)
F4'	0.143 (2)	0.8495 (18)	1.0606 (13)	0.115 (5)	0.65 (2)
F5'	0.004 (3)	0.643 (3)	0.937 (3)	0.151 (12)	0.35 (2)
F6'	0.298 (4)	0.843 (3)	0.936 (2)	0.097 (8)	0.35 (2)
P2	0.71510 (11)	0.77369 (9)	0.42397 (8)	0.0508 (3)
F7	0.863 (3)	0.772 (3)	0.536 (2)	0.073 (5)	0.41 (5)
F8	0.671 (5)	0.902 (2)	0.513 (3)	0.119 (8)	0.41 (5)
F9	0.573 (4)	0.776 (5)	0.328 (3)	0.135 (11)	0.41 (5)
F10	0.803 (4)	0.865 (3)	0.380 (3)	0.070 (4)	0.41 (5)
F11	0.765 (3)	0.6468 (16)	0.3366 (17)	0.084 (5)	0.41 (5)
F12	0.588 (3)	0.659 (2)	0.4499 (13)	0.039 (4)	0.41 (5)
F8'	0.633 (2)	0.8923 (15)	0.4897 (19)	0.088 (4)	0.59 (5)
F9'	0.561 (2)	0.747 (2)	0.3081 (16)	0.080 (4)	0.59 (5)
F7'	0.864 (3)	0.800 (4)	0.526 (2)	0.127 (8)	0.59 (5)
F11'	0.791 (2)	0.6508 (15)	0.359 (2)	0.093 (4)	0.59 (5)
F10'	0.849 (3)	0.891 (2)	0.402 (2)	0.075 (3)	0.59 (5)
F12'	0.602 (3)	0.673 (2)	0.4581 (16)	0.083 (6)	0.59 (5)
N1	0.6733 (4)	0.7139 (4)	0.9682 (3)	0.0524 (8)
C1	0.7252 (7)	0.7372 (7)	1.0910 (4)	0.0879 (17)
H1A	0.7686	0.8359	1.1336	0.132*
H1B	0.8132	0.6858	1.1081	0.132*
H1C	0.6281	0.7052	1.1119	0.132*
N2	0.6251 (4)	0.7563 (3)	0.8105 (2)	0.0432 (7)
C2	0.6823 (4)	0.8143 (4)	0.9236 (3)	0.0452 (8)
H2A	0.7224	0.9101	0.9650	0.054*
N3	0.2487 (4)	0.7375 (3)	0.5612 (3)	0.0450 (7)
C3	0.5781 (5)	0.6144 (4)	0.7827 (4)	0.0597 (11)
H3A	0.5335	0.5478	0.7091	0.072*
N4	0.1799 (4)	0.6783 (3)	0.3781 (3)	0.0458 (7)
C4	0.6078 (5)	0.5889 (4)	0.8803 (4)	0.0645 (12)
H4A	0.5874	0.5008	0.8873	0.077*
C5	0.6155 (6)	0.8329 (5)	0.7305 (4)	0.0671 (12)
H5A	0.5976	0.7665	0.6540	0.081*
H5B	0.7237	0.8980	0.7523	0.081*
C6	0.4733 (7)	0.9135 (5)	0.7285 (4)	0.0737 (14)
H6A	0.4898	0.9764	0.8060	0.088*
H6B	0.4830	0.9715	0.6822	0.088*
C7	0.2951 (6)	0.8265 (5)	0.6833 (4)	0.0699 (13)
H7A	0.2848	0.7666	0.7281	0.084*
H7B	0.2147	0.8886	0.6931	0.084*
C8	0.2296 (4)	0.7848 (4)	0.4749 (3)	0.0440 (8)
H8A	0.2486	0.8793	0.4819	0.053*
C9	0.1662 (5)	0.5574 (4)	0.4025 (4)	0.0606 (11)
H9A	0.1337	0.4660	0.3495	0.073*
C10	0.2074 (5)	0.5934 (4)	0.5150 (4)	0.0609 (11)
H10A	0.2082	0.5320	0.5556	0.073*
C11	0.1433 (6)	0.6887 (6)	0.2638 (4)	0.0789 (14)
H11A	0.1623	0.7862	0.2709	0.118*
H11B	0.0261	0.6447	0.2209	0.118*
H11C	0.2176	0.6422	0.2247	0.118*

	U11	U22	U33	U12	U13	U23
P1	0.0474 (5)	0.0577 (6)	0.0566 (6)	0.0048 (4)	0.0160 (4)	0.0139 (4)
F1	0.124 (8)	0.185 (12)	0.171 (12)	0.084 (8)	0.069 (8)	0.146 (11)
F2	0.081 (4)	0.157 (10)	0.082 (5)	0.029 (6)	0.005 (3)	0.047 (6)
F3	0.141 (7)	0.077 (5)	0.081 (5)	−0.021 (5)	0.066 (4)	−0.019 (3)
F4	0.098 (10)	0.049 (6)	0.17 (2)	0.013 (6)	0.100 (12)	−0.003 (9)
F5	0.107 (9)	0.090 (6)	0.131 (6)	−0.011 (5)	0.063 (6)	0.047 (5)
F6	0.068 (4)	0.059 (4)	0.130 (10)	−0.007 (3)	0.047 (5)	0.013 (5)
F1'	0.073 (7)	0.159 (18)	0.093 (8)	0.019 (11)	−0.019 (7)	0.050 (12)
F2'	0.091 (11)	0.111 (12)	0.139 (15)	0.061 (10)	0.019 (10)	0.070 (11)
F3'	0.174 (16)	0.104 (11)	0.12 (3)	−0.081 (12)	0.09 (2)	−0.047 (15)
F4'	0.174 (11)	0.088 (8)	0.079 (5)	0.007 (6)	0.077 (6)	0.000 (5)
F5'	0.060 (7)	0.090 (13)	0.24 (3)	−0.031 (7)	0.080 (13)	−0.039 (14)
F6'	0.131 (18)	0.096 (11)	0.057 (7)	−0.035 (9)	0.054 (9)	0.017 (6)
P2	0.0517 (5)	0.0472 (5)	0.0584 (6)	0.0079 (4)	0.0169 (4)	0.0189 (4)
F7	0.055 (6)	0.096 (8)	0.063 (7)	0.011 (5)	−0.004 (5)	0.040 (7)
F8	0.23 (2)	0.039 (6)	0.108 (10)	−0.009 (9)	0.120 (12)	0.005 (6)
F9	0.093 (12)	0.21 (3)	0.128 (19)	0.047 (15)	0.005 (11)	0.12 (2)
F10	0.063 (10)	0.053 (10)	0.089 (9)	−0.027 (6)	0.026 (8)	0.027 (8)
F11	0.129 (11)	0.052 (7)	0.060 (7)	−0.011 (8)	0.058 (6)	−0.008 (6)
F12	0.049 (6)	0.027 (5)	0.041 (6)	−0.003 (4)	0.021 (4)	0.011 (4)
F8'	0.109 (7)	0.042 (5)	0.144 (11)	0.041 (5)	0.087 (6)	0.029 (6)
F9'	0.059 (5)	0.120 (7)	0.059 (5)	0.015 (4)	0.008 (3)	0.036 (5)
F7'	0.081 (7)	0.191 (17)	0.104 (8)	−0.001 (9)	−0.013 (5)	0.084 (9)
F11'	0.098 (6)	0.084 (7)	0.157 (12)	0.063 (6)	0.096 (7)	0.063 (8)
F10'	0.068 (8)	0.046 (6)	0.103 (9)	−0.028 (5)	0.044 (7)	0.017 (5)
F12'	0.085 (9)	0.066 (9)	0.110 (10)	0.005 (6)	0.055 (8)	0.032 (7)
N1	0.0406 (17)	0.073 (2)	0.0564 (19)	0.0199 (15)	0.0175 (15)	0.0355 (18)
C1	0.074 (3)	0.144 (5)	0.075 (3)	0.039 (3)	0.024 (3)	0.072 (4)
N2	0.0390 (15)	0.0474 (17)	0.0381 (15)	0.0049 (12)	0.0096 (12)	0.0108 (13)
C2	0.0433 (19)	0.047 (2)	0.0394 (19)	0.0078 (15)	0.0073 (15)	0.0113 (16)
N3	0.0434 (16)	0.0528 (18)	0.0523 (18)	0.0164 (13)	0.0173 (14)	0.0321 (15)
C3	0.052 (2)	0.046 (2)	0.065 (3)	0.0067 (17)	0.013 (2)	0.0041 (19)
N4	0.0344 (15)	0.0536 (18)	0.0444 (17)	0.0071 (13)	0.0079 (12)	0.0139 (14)
C4	0.050 (2)	0.050 (2)	0.101 (4)	0.0120 (18)	0.024 (2)	0.033 (2)
C5	0.065 (3)	0.085 (3)	0.047 (2)	−0.006 (2)	0.010 (2)	0.030 (2)
C6	0.111 (4)	0.059 (3)	0.039 (2)	0.019 (3)	0.002 (2)	0.0170 (19)
C7	0.081 (3)	0.097 (4)	0.050 (2)	0.047 (3)	0.026 (2)	0.035 (2)
C8	0.0453 (19)	0.0414 (19)	0.051 (2)	0.0084 (15)	0.0115 (16)	0.0261 (17)
C9	0.044 (2)	0.037 (2)	0.089 (3)	0.0003 (16)	0.012 (2)	0.014 (2)
C10	0.048 (2)	0.054 (2)	0.094 (3)	0.0080 (18)	0.018 (2)	0.049 (2)
C11	0.068 (3)	0.108 (4)	0.053 (3)	0.020 (3)	0.009 (2)	0.024 (3)

P1—F2	1.536 (8)	C1—H1C	0.9600
P1—F5'	1.534 (19)	N2—C2	1.322 (4)
P1—F4'	1.528 (12)	N2—C3	1.362 (5)
P1—F6'	1.51 (2)	N2—C5	1.465 (5)
P1—F1	1.563 (10)	C2—H2A	0.9300
P1—F1'	1.509 (18)	N3—C8	1.322 (4)
P1—F3'	1.556 (16)	N3—C10	1.369 (5)
P1—F5	1.561 (11)	N3—C7	1.475 (5)
P1—F3	1.565 (7)	C3—C4	1.328 (6)
P1—F2'	1.601 (12)	C3—H3A	0.9300
P1—F6	1.603 (14)	N4—C8	1.307 (5)
P1—F4	1.62 (2)	N4—C9	1.362 (5)
F1'—F4'	1.77 (3)	N4—C11	1.463 (5)
P2—F11'	1.565 (10)	C4—H4A	0.9300
P2—F7'	1.48 (2)	C5—C6	1.501 (7)
P2—F12'	1.54 (2)	C5—H5A	0.9700
P2—F9	1.48 (3)	C5—H5B	0.9700
P2—F7	1.65 (3)	C6—C7	1.497 (7)
P2—F10	1.44 (3)	C6—H6A	0.9700
P2—F8'	1.572 (9)	C6—H6B	0.9700
P2—F10'	1.674 (19)	C7—H7A	0.9700
P2—F8	1.596 (18)	C7—H7B	0.9700
P2—F12	1.65 (2)	C8—H8A	0.9300
P2—F11	1.597 (13)	C9—C10	1.319 (6)
P2—F9'	1.62 (2)	C9—H9A	0.9300
N1—C2	1.323 (5)	C10—H10A	0.9300
N1—C4	1.358 (6)	C11—H11A	0.9600
N1—C1	1.463 (5)	C11—H11B	0.9600
C1—H1A	0.9600	C11—H11C	0.9600
C1—H1B	0.9600
F2—P1—F5'	70.4 (13)	F10'—P2—F9'	95.3 (12)
F5'—P1—F4'	90.8 (12)	C2—N1—C4	107.8 (3)
F5'—P1—F6'	160 (2)	C2—N1—C1	124.8 (4)
F4'—P1—F6'	97.2 (11)	C4—N1—C1	127.3 (4)
F2—P1—F1	160.9 (14)	N1—C1—H1A	109.5
F5'—P1—F1'	112 (2)	N1—C1—H1B	109.5
F4'—P1—F1'	71.3 (12)	H1A—C1—H1B	109.5
F6'—P1—F1'	87.2 (14)	N1—C1—H1C	109.5
F5'—P1—F3'	89.3 (13)	H1A—C1—H1C	109.5
F4'—P1—F3'	161.5 (16)	H1B—C1—H1C	109.5
F6'—P1—F3'	88.8 (14)	C2—N2—C3	108.1 (3)
F1'—P1—F3'	91.6 (14)	C2—N2—C5	125.3 (3)
F2—P1—F5	88.4 (7)	C3—N2—C5	126.6 (3)
F1—P1—F5	80.4 (9)	N1—C2—N2	108.9 (3)
F2—P1—F3	77.4 (8)	N1—C2—H2A	125.6
F1—P1—F3	88.5 (7)	N2—C2—H2A	125.6
F5—P1—F3	96.3 (7)	C8—N3—C10	107.2 (3)
F5'—P1—F2'	93.1 (12)	C8—N3—C7	125.2 (3)
F4'—P1—F2'	81.4 (13)	C10—N3—C7	127.5 (3)
F6'—P1—F2'	70.4 (15)	C4—C3—N2	107.2 (4)
F1'—P1—F2'	142 (2)	C4—C3—H3A	126.4
F3'—P1—F2'	117 (2)	N2—C3—H3A	126.4
F2—P1—F6	101.0 (9)	C8—N4—C9	108.1 (3)
F1—P1—F6	91.1 (7)	C8—N4—C11	125.4 (4)
F5—P1—F6	170.3 (9)	C9—N4—C11	126.5 (4)
F3—P1—F6	88.2 (6)	C3—C4—N1	108.0 (4)
F2—P1—F4	88.3 (15)	C3—C4—H4A	126.0
F1—P1—F4	106.7 (12)	N1—C4—H4A	126.0
F5—P1—F4	89.2 (10)	N2—C5—C6	112.3 (4)
F3—P1—F4	164.5 (13)	N2—C5—H5A	109.2
F6—P1—F4	88.6 (9)	C6—C5—H5A	109.2
P1—F1'—F4'	54.9 (9)	N2—C5—H5B	109.1
P1—F4'—F1'	53.8 (8)	C6—C5—H5B	109.1
F11'—P2—F7'	87.0 (11)	H5A—C5—H5B	107.9
F11'—P2—F12'	92.0 (9)	C7—C6—C5	115.9 (4)
F7'—P2—F12'	93.3 (13)	C7—C6—H6A	108.3
F9—P2—F7	175.4 (16)	C5—C6—H6A	108.3
F9—P2—F10	79 (2)	C7—C6—H6B	108.3
F7—P2—F10	104.1 (17)	C5—C6—H6B	108.3
F11'—P2—F8'	177.5 (8)	H6A—C6—H6B	107.4
F7'—P2—F8'	93.5 (11)	N3—C7—C6	113.1 (4)
F12'—P2—F8'	85.5 (9)	N3—C7—H7A	109.0
F11'—P2—F10'	90.5 (10)	C6—C7—H7A	109.0
F7'—P2—F10'	81.4 (19)	N3—C7—H7B	109.0
F12'—P2—F10'	174.0 (13)	C6—C7—H7B	109.0
F8'—P2—F10'	92.0 (10)	H7A—C7—H7B	107.8
F9—P2—F8	91.7 (16)	N4—C8—N3	109.4 (3)
F7—P2—F8	85.2 (16)	N4—C8—H8A	125.3
F10—P2—F8	92.9 (14)	N3—C8—H8A	125.3
F9—P2—F12	90.7 (15)	C10—C9—N4	107.6 (4)
F7—P2—F12	86.0 (11)	C10—C9—H9A	126.2
F10—P2—F12	169.4 (14)	N4—C9—H9A	126.2
F8—P2—F12	91.3 (10)	C9—C10—N3	107.6 (3)
F9—P2—F11	89.6 (16)	C9—C10—H10A	126.2
F7—P2—F11	93.5 (12)	N3—C10—H10A	126.2
F10—P2—F11	86.4 (15)	N4—C11—H11A	109.5
F8—P2—F11	178.3 (13)	N4—C11—H11B	109.5
F12—P2—F11	89.8 (9)	H11A—C11—H11B	109.5
F11'—P2—F9'	91.1 (10)	N4—C11—H11C	109.5
F7'—P2—F9'	176.2 (13)	H11A—C11—H11C	109.5
F12'—P2—F9'	90.1 (10)	H11B—C11—H11C	109.5
F8'—P2—F9'	88.5 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F6i	0.93	2.41	3.256 (16)	151
C7—H7A···F3	0.97	2.49	3.446 (12)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F6i	0.93	2.41	3.256 (16)	151
C7—H7A⋯F3	0.97	2.49	3.446 (12)	167

Symmetry code: (i) .