Acta Cryst. (2008). E64, o2480 [ doi:10.1107/S160053680803746X ]
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.
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)
Both two distinct hexafluorophosphate groups are disordered over two sites while central P atoms are fixed; the site occupancy factors were refined and converged to 0.65 (2) and 0.35 (2) for F1—F6 and F1'—F6', 0.41 (5) and 0.59 (5) for F7—F12 and F7'—F12' respectively.
H atoms were positioned geometrically, with C—H = 0.93, 0.96 and 0.97 Å for methine, methyl, methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
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).
![[Figure 1]](./rn2047fig1thm.gif)
| 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. |
![[Figure 2]](./rn2047fig2thm.gif)
| Fig. 2. Crystal packing in (I). Dashed lines indicate intermolecular C-H···F hydrogen bonds. |
| C11H18N42+·2PF6− | Z = 2 |
| Mr = 496.23 | F(000) = 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 = 10–12° |
| 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 |
| Enraf–Nonius CAD-4 diffractometer | 2637 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.000 |
| graphite | θmax = 25.2°, θmin = 1.8° |
| ω/2θ scans | h = −9→9 |
| Absorption correction: ψ scan (North et al., 1968) | k = −12→11 |
| Tmin = 0.905, Tmax = 0.935 | l = 0→15 |
| 3484 measured reflections | 3 standard reflections every 200 reflections |
| 3484 independent reflections | intensity decay: none |
| 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(Fo2) + (0.1017P)2 + 1.1631P] where P = (Fo2 + 2Fc2)/3 |
| 3484 reflections | (Δ/σ)max = 0.008 |
| 372 parameters | Δρmax = 0.30 e Å−3 |
| 0 restraints | Δρmin = −0.48 e Å−3 |
| C11H18N42+·2PF6− | γ = 96.35 (3)° |
| Mr = 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)° |
| Enraf–Nonius CAD-4 diffractometer | 2637 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.000 |
| Tmin = 0.905, Tmax = 0.935 | θmax = 25.2° |
| 3484 measured reflections | 3 standard reflections every 200 reflections |
| 3484 independent reflections | intensity decay: none |
| R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
| wR(F2) = 0.180 | Δρmax = 0.30 e Å−3 |
| S = 0.97 | Δρmin = −0.48 e Å−3 |
| 3484 reflections | Absolute structure: ? |
| 372 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 |
| Symmetry codes: (i) −x+1, −y+2, −z+2. |
| 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 codes: (i) −x+1, −y+2, −z+2. |
The authors thank Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for carrying out the X-ray crystallographic analysis.
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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.