3,3′-Dimethyl-1,1′-(propane-1,3-di­yl)diimidazol-1-ium bis(hexafluoro­phosphate)

Liang, J.; Dong, S.; Cang, H.; Wang, J.

doi:10.1107/S160053680803746X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2480

doi:10.1107/S160053680803746X

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3,3′-Dimethyl-1,1′-(propane-1,3-diyl)diimidazol-1-ium bis(hexafluorophosphate)

Jin-hua Liang,^a Su-lan Dong,^a,^b Hui Cang ^a and Jin-tang Wang ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bHuaiyin Institute of Technology, Huaiyin 223003, People's Republic of China
^*Correspondence e-mail: wjt@njut.edu.cn

(Received 4 July 2008; accepted 12 November 2008; online 29 November 2008)

In the title compound, C₁₁H₁₈N₄²⁺·2PF₆⁻, the dihedral angle between the two planar imidozlium rings is 6.1 (2)°. Both [PF₆]⁻ anions are disordered [occupancies 0.65 (2):0.35 (2) and 0.59 (5):0.41 (5)]. The crystal packing is stabilized by intermolecular C—H⋯F hydrogen bonds which link two molecules, 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

C₁₁H₁₈N₄²⁺·2PF₆⁻
M_r = 496.23
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.179
S = 0.97
3484 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.48 e Å⁻³

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) -x+1, -y+2, -z+2.

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound is a dicationic ionic liquid, which has high thermal stability. Applications of the dicationic ionic liquid are found in biochemistry as well as many areas of chemistry (Jared et al., 2005). We report the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C1—C5/N1/N2) and B (C7—C11/N3/N4) are, of course, planar and the dihedral angle between them is 6.1 (2) °. In the crystal structure, intermolecular C-H···F hydrogen bonds (Table 1) link the molecules (Fig. 2), forming centrosymmetric dimers, which may be effective in the stabilization of the crystals.

Related literature top

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

Experimental top

1,3-Dibromide propane(10.1 g, 0.05 mol) was added to acetonitrile solution(50 ml) of dehydrate imidazole(9.4 g, 0.11 mol) at 353 K. After stirring for 24 h, the mixture was cooled to room temperature and filtered. The solids were washed with ethyl acetate and dried. Above solid(1.42 g, 5 mmol) was dissolved in distilled water(50 mL) and potassium hexafluorophosphate(1.84 g, 10 mmol) was added. After stirring at room temperature for 3 h, a white solid formed which was collected by filtration, washed with distilled water(20 mL) and dried; The product was purified by repeated crystallization. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of acetone. Each starting material was distilled in advance under reduced pressure with 5 Å molecular sieve. (yield; 0.848 g, 40 %, m.p. 414 K)

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50 % probability level. Dashed lines indicate C-H···F hydrogen bonds.
	Fig. 2. Crystal packing in (I). Dashed lines indicate intermolecular C-H···F hydrogen bonds.

3,3'-Dimethyl-1,1'-(propane-1,3-diyl)diimidazol-1-ium bis(hexafluorophosphate) top

Crystal data top

C₁₁H₁₈N₄²⁺·2PF₆⁻	Z = 2
M_r = 496.23	F(000) = 500
Triclinic, P1	D_x = 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 = 10–12°
α = 107.99 (3)°	µ = 0.34 mm⁻¹
β = 104.50 (3)°	T = 298 K
γ = 96.35 (3)°	Block, colorless
V = 972.1 (5) Å³	0.30 × 0.30 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2637 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.2°, θ_min = 1.8°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −12→11
T_min = 0.905, T_max = 0.935	l = 0→15
3484 measured reflections	3 standard reflections every 200 reflections
3484 independent reflections	intensity decay: none

Refinement top

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.1017P)² + 1.1631P] where P = (F_o² + 2F_c²)/3
3484 reflections	(Δ/σ)_max = 0.008
372 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₁H₁₈N₄²⁺·2PF₆⁻	γ = 96.35 (3)°
M_r = 496.23	V = 972.1 (5) Å³
Triclinic, P1	Z = 2
a = 8.2300 (16) Å	Mo Kα radiation
b = 10.192 (2) Å	µ = 0.34 mm⁻¹
c = 12.856 (3) Å	T = 298 K
α = 107.99 (3)°	0.30 × 0.30 × 0.20 mm
β = 104.50 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2637 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.905, T_max = 0.935	3 standard reflections every 200 reflections
3484 measured reflections	intensity decay: none
3484 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 0.97	Δρ_max = 0.30 e Å⁻³
3484 reflections	Δρ_min = −0.48 e Å⁻³
372 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₈N₄²⁺·2PF₆⁻
M_r	496.23
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.2300 (16), 10.192 (2), 12.856 (3)
α, β, γ (°)	107.99 (3), 104.50 (3), 96.35 (3)
V (Å³)	972.1 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.905, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	3484, 3484, 2637
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.180, 0.97
No. of reflections	3484
No. of parameters	372
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.48

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F6ⁱ	0.9300	2.4100	3.256 (16)	151.00
C7—H7A···F3	0.9700	2.4900	3.446 (12)	167.00

Symmetry code: (i) −x+1, −y+2, −z+2.

Acknowledgements

The authors thank Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for carrying out the X-ray crystallographic analysis.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Jared, L. A., Ding, R. F., Ellern, A. & Armstrong, D. W. (2005). J. Am. Chem. Soc. 127, 593–604. Web of Science PubMed Google Scholar
Matsumoto, K. & Hagiwara, R. (2007). J. Fluorine Chem. 128, 317–331. Web of Science CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page o2480

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,3′-Di­methyl-1,1′-(propane-1,3-di­yl)diimidazol-1-ium bis­(hexa­fluoro­phosphate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,3′-Dimethyl-1,1′-(propane-1,3-diyl)diimidazol-1-ium bis(hexafluorophosphate)