Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026955/lh2402sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026955/lh2402Isup2.hkl |
CCDC reference: 654973
The title compound was synthesized according to the literature procedure (Bortolini et al., 2003).
All H atoms were included in calculated positions and refined as riding (C—H = 0.93–0.97 Å; N—H = 0.88 Å), with Uiso(H) = 1.5Ueq(C) for methyl and 1.2Ueq(C,N) for all other H atoms. The largest peak in the final difference Fourier of 1.33 e Å-3 is 0.83 Å from atom H7. The F atoms of the anion are disordered over two sites with refined occupancies 0.859 (6) and 0.141 (6) for the major and minor components.
Room-temperature ionic liquids are attracting significant interest owing to their chemical characteristics and potentially useful solvent properties (Dibrov & Kochi, 2006) and imidazolium salts, which are regarded as a type of ionic liquids, have an extensive application in organic synthesis (Pretti et al., 2006).
The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the quinoline plane and imidazole plane is 78.02 (7) °. In the crystal structure, π-π stacking internactions link molecules into centrosymmetric dimers. In addtion, weak intermolecular C—H···F and C—H···O interactions help stabilize the crystal structure.
For related literature, see: Bortolini et al. (2003); Dibrov & Kochi (2006); Pretti et al. (2006).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXTL (Bruker, 1998).
C15H17N3O+·F6P− | Z = 8 |
Mr = 400.29 | F(000) = 1640 |
Monoclinic, C2/c | Dx = 1.527 Mg m−3 |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2183 (11) Å | µ = 0.23 mm−1 |
b = 21.3444 (19) Å | T = 291 K |
c = 14.4056 (13) Å | Block, colourless |
β = 112.059 (1)° | 0.24 × 0.18 × 0.16 mm |
V = 3481.9 (5) Å3 |
Bruker SMART CCD area-detector diffractometer | 3087 independent reflections |
Radiation source: fine-focus sealed tube | 2808 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.108 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→13 |
Tmin = 0.947, Tmax = 0.964 | k = −25→25 |
12564 measured reflections | l = −16→17 |
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)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.0848P)2 + 6.8821P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3087 reflections | Δρmax = 1.13 e Å−3 |
293 parameters | Δρmin = −0.67 e Å−3 |
108 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0026 (5) |
C15H17N3O+·F6P− | V = 3481.9 (5) Å3 |
Mr = 400.29 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.2183 (11) Å | µ = 0.23 mm−1 |
b = 21.3444 (19) Å | T = 291 K |
c = 14.4056 (13) Å | 0.24 × 0.18 × 0.16 mm |
β = 112.059 (1)° |
Bruker SMART CCD area-detector diffractometer | 3087 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2808 reflections with I > 2σ(I) |
Tmin = 0.947, Tmax = 0.964 | Rint = 0.108 |
12564 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 108 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.05 | Δρmax = 1.13 e Å−3 |
3087 reflections | Δρmin = −0.67 e Å−3 |
293 parameters |
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 | 0.01910 (7) | 0.33923 (4) | 0.99358 (6) | 0.0431 (3) | |
F1 | 0.0575 (5) | 0.3561 (2) | 1.1098 (3) | 0.092 (2) | 0.859 (6) |
F2 | 0.0141 (3) | 0.26827 (11) | 1.0220 (2) | 0.0687 (9) | 0.859 (6) |
F3 | −0.1135 (2) | 0.3483 (2) | 0.9796 (3) | 0.0951 (13) | 0.859 (6) |
F4 | 0.0294 (4) | 0.41165 (15) | 0.9733 (3) | 0.1144 (16) | 0.859 (6) |
F5 | 0.1552 (2) | 0.33103 (19) | 1.0130 (3) | 0.0916 (12) | 0.859 (6) |
F6 | −0.0185 (5) | 0.3223 (3) | 0.8809 (3) | 0.118 (3) | 0.859 (6) |
F1' | 0.0459 (14) | 0.3516 (7) | 1.1049 (6) | 0.038 (6) | 0.141 (6) |
F2' | −0.0984 (11) | 0.3001 (8) | 0.9825 (10) | 0.080 (6) | 0.141 (6) |
F3' | −0.0593 (16) | 0.3991 (6) | 0.9584 (11) | 0.089 (7) | 0.141 (6) |
F4' | 0.1291 (12) | 0.3739 (9) | 0.9927 (12) | 0.113 (9) | 0.141 (6) |
F5' | 0.0894 (16) | 0.2751 (6) | 1.0179 (12) | 0.117 (9) | 0.141 (6) |
F6' | −0.0142 (12) | 0.3222 (7) | 0.8752 (7) | 0.046 (6) | 0.141 (6) |
N1 | 0.35973 (18) | 0.67281 (10) | 0.14547 (16) | 0.0286 (5) | |
N2 | 0.51217 (19) | 0.55385 (10) | 0.12278 (15) | 0.0297 (5) | |
H2 | 0.5699 | 0.5799 | 0.1455 | 0.036* | |
N3 | 0.29978 (19) | 0.68579 (10) | 0.26701 (16) | 0.0324 (5) | |
O1 | 0.73297 (16) | 0.51432 (9) | 0.21731 (16) | 0.0406 (5) | |
C1 | 0.5310 (2) | 0.49095 (12) | 0.13432 (18) | 0.0302 (6) | |
C2 | 0.4026 (2) | 0.57384 (13) | 0.07571 (19) | 0.0326 (6) | |
C3 | 0.3228 (2) | 0.64369 (12) | 0.20928 (19) | 0.0305 (6) | |
H3 | 0.3143 | 0.6006 | 0.2130 | 0.037* | |
C4 | 0.3047 (2) | 0.53339 (14) | 0.0384 (2) | 0.0403 (7) | |
H4 | 0.2290 | 0.5494 | 0.0063 | 0.048* | |
C5 | 0.6489 (2) | 0.46864 (12) | 0.1842 (2) | 0.0336 (6) | |
C6 | 0.3226 (3) | 0.47019 (14) | 0.0499 (2) | 0.0407 (7) | |
H6 | 0.2588 | 0.4429 | 0.0260 | 0.049* | |
C7 | 0.4631 (3) | 0.38144 (13) | 0.1118 (2) | 0.0410 (7) | |
H7 | 0.4025 | 0.3522 | 0.0882 | 0.049* | |
C8 | 0.4378 (2) | 0.44646 (13) | 0.09821 (19) | 0.0338 (6) | |
C9 | 0.3866 (3) | 0.64389 (13) | 0.0633 (2) | 0.0360 (6) | |
H9A | 0.4582 | 0.6624 | 0.0612 | 0.043* | |
H9B | 0.3229 | 0.6528 | 0.0000 | 0.043* | |
C10 | 0.3589 (3) | 0.73643 (13) | 0.1622 (2) | 0.0385 (6) | |
H10 | 0.3799 | 0.7680 | 0.1275 | 0.046* | |
C11 | 0.6706 (3) | 0.40540 (13) | 0.1961 (2) | 0.0407 (7) | |
H11 | 0.7475 | 0.3910 | 0.2284 | 0.049* | |
C12 | 0.3219 (3) | 0.74401 (13) | 0.2382 (2) | 0.0401 (7) | |
H12 | 0.3130 | 0.7820 | 0.2663 | 0.048* | |
C13 | 0.5766 (3) | 0.36226 (13) | 0.1594 (2) | 0.0436 (7) | |
H13 | 0.5927 | 0.3196 | 0.1680 | 0.052* | |
C14 | 0.2529 (3) | 0.67183 (15) | 0.3445 (2) | 0.0460 (7) | |
H14A | 0.1684 | 0.6752 | 0.3166 | 0.069* | |
H14B | 0.2846 | 0.7011 | 0.3987 | 0.069* | |
H14C | 0.2750 | 0.6300 | 0.3690 | 0.069* | |
C15 | 0.8535 (3) | 0.49475 (17) | 0.2664 (3) | 0.0613 (10) | |
H15A | 0.8622 | 0.4725 | 0.3266 | 0.092* | |
H15B | 0.9040 | 0.5309 | 0.2827 | 0.092* | |
H15C | 0.8749 | 0.4678 | 0.2226 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0324 (5) | 0.0473 (5) | 0.0488 (5) | −0.0030 (3) | 0.0140 (3) | 0.0112 (3) |
F1 | 0.112 (4) | 0.076 (3) | 0.066 (3) | 0.004 (3) | 0.009 (2) | −0.017 (2) |
F2 | 0.092 (2) | 0.0408 (13) | 0.0805 (18) | −0.0165 (13) | 0.0406 (16) | −0.0023 (12) |
F3 | 0.0347 (14) | 0.126 (3) | 0.115 (3) | 0.0141 (16) | 0.0167 (14) | −0.015 (2) |
F4 | 0.113 (3) | 0.068 (2) | 0.128 (3) | −0.0150 (19) | 0.006 (2) | 0.0528 (19) |
F5 | 0.0423 (15) | 0.118 (3) | 0.122 (3) | −0.0103 (16) | 0.0385 (16) | 0.007 (2) |
F6 | 0.125 (5) | 0.168 (5) | 0.057 (3) | −0.007 (4) | 0.029 (3) | 0.003 (3) |
F1' | 0.047 (8) | 0.035 (9) | 0.034 (9) | 0.004 (6) | 0.019 (7) | 0.015 (7) |
F2' | 0.082 (10) | 0.101 (11) | 0.067 (8) | −0.024 (8) | 0.039 (7) | 0.009 (7) |
F3' | 0.102 (11) | 0.073 (9) | 0.094 (10) | 0.033 (8) | 0.039 (8) | 0.015 (7) |
F4' | 0.100 (12) | 0.111 (12) | 0.134 (13) | −0.018 (9) | 0.052 (9) | 0.002 (9) |
F5' | 0.114 (12) | 0.101 (12) | 0.116 (12) | 0.033 (9) | 0.021 (9) | −0.005 (9) |
F6' | 0.037 (8) | 0.083 (11) | 0.033 (9) | −0.009 (7) | 0.032 (7) | 0.002 (7) |
N1 | 0.0253 (10) | 0.0285 (11) | 0.0319 (11) | 0.0030 (8) | 0.0105 (8) | 0.0018 (8) |
N2 | 0.0319 (11) | 0.0288 (11) | 0.0321 (11) | −0.0008 (9) | 0.0165 (9) | −0.0039 (9) |
N3 | 0.0322 (11) | 0.0332 (11) | 0.0325 (11) | 0.0028 (9) | 0.0130 (9) | −0.0019 (9) |
O1 | 0.0328 (10) | 0.0339 (10) | 0.0514 (12) | 0.0035 (8) | 0.0113 (9) | −0.0043 (9) |
C1 | 0.0380 (14) | 0.0310 (13) | 0.0274 (12) | 0.0017 (10) | 0.0190 (11) | −0.0021 (10) |
C2 | 0.0354 (13) | 0.0364 (14) | 0.0305 (13) | 0.0051 (11) | 0.0174 (11) | −0.0016 (11) |
C3 | 0.0335 (13) | 0.0269 (12) | 0.0314 (13) | 0.0033 (10) | 0.0124 (10) | 0.0017 (10) |
C4 | 0.0318 (14) | 0.0500 (17) | 0.0410 (15) | 0.0025 (12) | 0.0159 (12) | −0.0058 (13) |
C5 | 0.0377 (14) | 0.0323 (14) | 0.0337 (13) | 0.0018 (11) | 0.0166 (11) | −0.0033 (10) |
C6 | 0.0378 (15) | 0.0461 (17) | 0.0433 (15) | −0.0078 (12) | 0.0210 (12) | −0.0107 (13) |
C7 | 0.0544 (18) | 0.0345 (14) | 0.0419 (15) | −0.0075 (12) | 0.0270 (14) | −0.0057 (12) |
C8 | 0.0418 (14) | 0.0340 (14) | 0.0323 (13) | −0.0042 (11) | 0.0215 (11) | −0.0052 (11) |
C9 | 0.0391 (14) | 0.0381 (15) | 0.0357 (14) | 0.0082 (11) | 0.0195 (12) | 0.0039 (11) |
C10 | 0.0421 (15) | 0.0278 (13) | 0.0478 (16) | −0.0030 (11) | 0.0193 (13) | 0.0012 (12) |
C11 | 0.0483 (16) | 0.0335 (14) | 0.0420 (15) | 0.0088 (12) | 0.0190 (13) | 0.0016 (12) |
C12 | 0.0465 (16) | 0.0276 (13) | 0.0471 (16) | 0.0012 (11) | 0.0183 (13) | −0.0052 (12) |
C13 | 0.0627 (19) | 0.0275 (13) | 0.0463 (16) | 0.0018 (13) | 0.0271 (15) | 0.0005 (12) |
C14 | 0.0552 (18) | 0.0516 (18) | 0.0409 (16) | 0.0011 (14) | 0.0290 (14) | −0.0024 (13) |
C15 | 0.0341 (16) | 0.051 (2) | 0.084 (3) | 0.0072 (14) | 0.0059 (16) | −0.0075 (18) |
P1—F1' | 1.534 (8) | C2—C4 | 1.409 (4) |
P1—F4' | 1.539 (8) | C2—C9 | 1.510 (4) |
P1—F6 | 1.555 (4) | C3—H3 | 0.9300 |
P1—F3' | 1.563 (8) | C4—C6 | 1.367 (4) |
P1—F3 | 1.568 (3) | C4—H4 | 0.9300 |
P1—F2 | 1.576 (2) | C5—C11 | 1.374 (4) |
P1—F5' | 1.584 (8) | C6—C8 | 1.409 (4) |
P1—F4 | 1.587 (3) | C6—H6 | 0.9300 |
P1—F5 | 1.589 (3) | C7—C13 | 1.358 (5) |
P1—F1 | 1.601 (4) | C7—C8 | 1.420 (4) |
P1—F2' | 1.616 (8) | C7—H7 | 0.9300 |
P1—F6' | 1.639 (8) | C9—H9A | 0.9700 |
N1—C3 | 1.322 (3) | C9—H9B | 0.9700 |
N1—C10 | 1.380 (3) | C10—C12 | 1.343 (4) |
N1—C9 | 1.478 (3) | C10—H10 | 0.9300 |
N2—C2 | 1.323 (3) | C11—C13 | 1.411 (4) |
N2—C1 | 1.362 (3) | C11—H11 | 0.9300 |
N2—H2 | 0.8600 | C12—H12 | 0.9300 |
N3—C3 | 1.324 (3) | C13—H13 | 0.9300 |
N3—C12 | 1.369 (4) | C14—H14A | 0.9600 |
N3—C14 | 1.464 (3) | C14—H14B | 0.9600 |
O1—C5 | 1.366 (3) | C14—H14C | 0.9600 |
O1—C15 | 1.436 (4) | C15—H15A | 0.9600 |
C1—C8 | 1.423 (4) | C15—H15B | 0.9600 |
C1—C5 | 1.429 (4) | C15—H15C | 0.9600 |
F1'—P1—F4' | 94.7 (6) | C10—N1—C9 | 124.7 (2) |
F1'—P1—F6 | 174.1 (6) | C2—N2—C1 | 118.2 (2) |
F4'—P1—F6 | 91.2 (7) | C2—N2—H2 | 120.9 |
F1'—P1—F3' | 93.6 (5) | C1—N2—H2 | 120.9 |
F4'—P1—F3' | 92.0 (6) | C3—N3—C12 | 108.3 (2) |
F6—P1—F3' | 87.0 (7) | C3—N3—C14 | 125.2 (2) |
F1'—P1—F3 | 85.3 (6) | C12—N3—C14 | 126.5 (2) |
F4'—P1—F3 | 143.4 (8) | C5—O1—C15 | 117.5 (2) |
F6—P1—F3 | 90.5 (2) | N2—C1—C8 | 122.6 (2) |
F3'—P1—F3 | 51.7 (7) | N2—C1—C5 | 118.8 (2) |
F1'—P1—F2 | 84.7 (6) | C8—C1—C5 | 118.6 (2) |
F4'—P1—F2 | 125.7 (8) | N2—C2—C4 | 123.3 (3) |
F6—P1—F2 | 91.3 (2) | N2—C2—C9 | 116.2 (2) |
F3'—P1—F2 | 142.3 (7) | C4—C2—C9 | 120.5 (2) |
F3—P1—F2 | 90.74 (19) | N1—C3—N3 | 109.0 (2) |
F1'—P1—F5' | 91.8 (5) | N1—C3—H3 | 125.5 |
F4'—P1—F5' | 90.9 (6) | N3—C3—H3 | 125.5 |
F6—P1—F5' | 87.3 (7) | C6—C4—C2 | 118.9 (3) |
F3'—P1—F5' | 173.7 (7) | C6—C4—H4 | 120.5 |
F3—P1—F5' | 125.7 (8) | C2—C4—H4 | 120.5 |
F1'—P1—F4 | 91.4 (6) | O1—C5—C11 | 125.0 (3) |
F4'—P1—F4 | 53.1 (8) | O1—C5—C1 | 114.9 (2) |
F6—P1—F4 | 92.7 (3) | C11—C5—C1 | 120.1 (3) |
F3—P1—F4 | 90.3 (2) | C4—C6—C8 | 120.0 (3) |
F2—P1—F4 | 175.85 (18) | C4—C6—H6 | 120.0 |
F5'—P1—F4 | 144.0 (8) | C8—C6—H6 | 120.0 |
F1'—P1—F5 | 92.1 (6) | C13—C7—C8 | 119.5 (3) |
F6—P1—F5 | 92.2 (2) | C13—C7—H7 | 120.2 |
F3'—P1—F5 | 128.4 (7) | C8—C7—H7 | 120.2 |
F3—P1—F5 | 177.34 (19) | C6—C8—C7 | 123.0 (3) |
F2—P1—F5 | 89.34 (17) | C6—C8—C1 | 117.0 (3) |
F5'—P1—F5 | 54.7 (8) | C7—C8—C1 | 119.9 (3) |
F4—P1—F5 | 89.4 (2) | N1—C9—C2 | 112.1 (2) |
F4'—P1—F1 | 89.2 (7) | N1—C9—H9A | 109.2 |
F6—P1—F1 | 179.5 (3) | C2—C9—H9A | 109.2 |
F3'—P1—F1 | 93.3 (6) | N1—C9—H9B | 109.2 |
F3—P1—F1 | 89.4 (2) | C2—C9—H9B | 109.2 |
F2—P1—F1 | 88.2 (2) | H9A—C9—H9B | 107.9 |
F5'—P1—F1 | 92.4 (7) | C12—C10—N1 | 106.7 (2) |
F4—P1—F1 | 87.8 (2) | C12—C10—H10 | 126.6 |
F5—P1—F1 | 88.0 (2) | N1—C10—H10 | 126.6 |
F1'—P1—F2' | 91.4 (5) | C5—C11—C13 | 120.2 (3) |
F4'—P1—F2' | 173.8 (6) | C5—C11—H11 | 119.9 |
F6—P1—F2' | 82.7 (6) | C13—C11—H11 | 119.9 |
F3'—P1—F2' | 88.6 (5) | C10—C12—N3 | 107.6 (2) |
F2—P1—F2' | 53.8 (7) | C10—C12—H12 | 126.2 |
F5'—P1—F2' | 87.9 (5) | N3—C12—H12 | 126.2 |
F4—P1—F2' | 127.9 (7) | C7—C13—C11 | 121.7 (3) |
F5—P1—F2' | 142.5 (7) | C7—C13—H13 | 119.2 |
F1—P1—F2' | 96.9 (6) | C11—C13—H13 | 119.2 |
F1'—P1—F6' | 176.4 (6) | N3—C14—H14A | 109.5 |
F4'—P1—F6' | 88.6 (5) | N3—C14—H14B | 109.5 |
F3'—P1—F6' | 87.8 (5) | H14A—C14—H14B | 109.5 |
F3—P1—F6' | 93.0 (5) | N3—C14—H14C | 109.5 |
F2—P1—F6' | 92.2 (6) | H14A—C14—H14C | 109.5 |
F5'—P1—F6' | 86.6 (5) | H14B—C14—H14C | 109.5 |
F4—P1—F6' | 91.8 (6) | O1—C15—H15A | 109.5 |
F5—P1—F6' | 89.6 (5) | O1—C15—H15B | 109.5 |
F1—P1—F6' | 177.5 (6) | H15A—C15—H15B | 109.5 |
F2'—P1—F6' | 85.3 (5) | O1—C15—H15C | 109.5 |
C3—N1—C10 | 108.4 (2) | H15A—C15—H15C | 109.5 |
C3—N1—C9 | 126.7 (2) | H15B—C15—H15C | 109.5 |
C2—N2—C1—C8 | −0.2 (3) | C13—C7—C8—C6 | −179.8 (3) |
C2—N2—C1—C5 | 179.5 (2) | C13—C7—C8—C1 | 0.1 (4) |
C1—N2—C2—C4 | 0.9 (4) | N2—C1—C8—C6 | −0.7 (4) |
C1—N2—C2—C9 | −179.0 (2) | C5—C1—C8—C6 | 179.6 (2) |
C10—N1—C3—N3 | −0.8 (3) | N2—C1—C8—C7 | 179.4 (2) |
C9—N1—C3—N3 | −175.3 (2) | C5—C1—C8—C7 | −0.2 (4) |
C12—N3—C3—N1 | 0.6 (3) | C3—N1—C9—C2 | −16.9 (4) |
C14—N3—C3—N1 | 177.7 (2) | C10—N1—C9—C2 | 169.4 (2) |
N2—C2—C4—C6 | −0.7 (4) | N2—C2—C9—N1 | −93.1 (3) |
C9—C2—C4—C6 | 179.3 (2) | C4—C2—C9—N1 | 87.0 (3) |
C15—O1—C5—C11 | 1.4 (4) | C3—N1—C10—C12 | 0.7 (3) |
C15—O1—C5—C1 | −178.8 (3) | C9—N1—C10—C12 | 175.4 (2) |
N2—C1—C5—O1 | 0.8 (3) | O1—C5—C11—C13 | 179.5 (2) |
C8—C1—C5—O1 | −179.4 (2) | C1—C5—C11—C13 | −0.2 (4) |
N2—C1—C5—C11 | −179.4 (2) | N1—C10—C12—N3 | −0.4 (3) |
C8—C1—C5—C11 | 0.3 (4) | C3—N3—C12—C10 | −0.1 (3) |
C2—C4—C6—C8 | −0.3 (4) | C14—N3—C12—C10 | −177.2 (3) |
C4—C6—C8—C7 | −179.2 (3) | C8—C7—C13—C11 | 0.1 (4) |
C4—C6—C8—C1 | 0.9 (4) | C5—C11—C13—C7 | 0.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···F1i | 0.93 | 2.46 | 3.204 (5) | 137 |
C9—H9A···F2ii | 0.97 | 2.49 | 3.244 (4) | 135 |
C3—H3···O1iii | 0.93 | 2.27 | 3.122 (3) | 152 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x+1/2, y+1/2, z−1; (iii) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H17N3O+·F6P− |
Mr | 400.29 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 291 |
a, b, c (Å) | 12.2183 (11), 21.3444 (19), 14.4056 (13) |
β (°) | 112.059 (1) |
V (Å3) | 3481.9 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.24 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.947, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12564, 3087, 2808 |
Rint | 0.108 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.170, 1.05 |
No. of reflections | 3087 |
No. of parameters | 293 |
No. of restraints | 108 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.13, −0.67 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Putz, 2005), SHELXTL (Bruker, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···F1i | 0.93 | 2.46 | 3.204 (5) | 137 |
C9—H9A···F2ii | 0.97 | 2.49 | 3.244 (4) | 135 |
C3—H3···O1iii | 0.93 | 2.27 | 3.122 (3) | 152 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x+1/2, y+1/2, z−1; (iii) −x+1, y, −z+1/2. |
Room-temperature ionic liquids are attracting significant interest owing to their chemical characteristics and potentially useful solvent properties (Dibrov & Kochi, 2006) and imidazolium salts, which are regarded as a type of ionic liquids, have an extensive application in organic synthesis (Pretti et al., 2006).
The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the quinoline plane and imidazole plane is 78.02 (7) °. In the crystal structure, π-π stacking internactions link molecules into centrosymmetric dimers. In addtion, weak intermolecular C—H···F and C—H···O interactions help stabilize the crystal structure.