organic compounds
(5-Fluoro-4′-methylbiphenyl-3-yl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate
aKey Laboratory of Fine Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
*Correspondence e-mail: shaoying810724@163.com
In the title molecular salt, C22H21FI+·CF3SO3−, the dihedral angle between the rings of the biphenyl group is 65.6 (1)°. The ring of the mesitylene group is inclined to the fluorobenzene ring at an angle of 86.1 (3)° and the C—I—C bond angle is 97.0 (2)°. In the crystal, extremely short I⋯O contacts of 2.862 (5) and 2.932 (5) Å occur, due to the strong electrostatic interactions between the I atom and two adjacent trifluoromethanesulfonate counter-ions. There are also C—H⋯F and C—H⋯π interactions present: together with the I⋯O bonds, these result in a three-dimensional network.
CCDC reference: 994798
Related literature
For background to diaryliodonium salts, see: Grushin (2000); Merritt & Olofsson (2009).
Experimental
Crystal data
|
|
Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; 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
CCDC reference: 994798
10.1107/S160053681400720X/hb7213sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400720X/hb7213Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400720X/hb7213Isup3.cdx
Supporting information file. DOI: 10.1107/S160053681400720X/hb7213Isup4.cml
m-CPBA10 (85%, 2.5 mmol), 3-fluoro-5-iodo-4'-methylbiphenyl (2.0 mmol), and mesitylene (3.0 mmol) were dissolved in CH2Cl2 (5 ml). Then, TfOH (5.0 mmol) was added to the solution dropwise at 0 °C and the mixture was stirred at room temperature for 2 h and the solution was concentrated in vacuo. Et2O (1 ml) was added and the mixture was stirred at r.t. for 10 min to precipitate out an yellow solid. The precipitate was filtered off, washed with Et2O, and dried under vacuum to give the salt. Yield 76%. Yellow blocks were obtained by slow evaporation of a petroleum / CH2Cl2 solution.
All the H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).Fig. 1. View of the title compound, showing 50% probability ellipsoids. | |
Fig. 2. Perspective view of the title compound along a direction. Labels of atoms have been omitted for clarity. |
C22H21FI+·CF3O3S− | F(000) = 1152 |
Mr = 580.37 | Dx = 1.650 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3546 reflections |
a = 9.8987 (8) Å | θ = 0–25.5° |
b = 24.374 (2) Å | µ = 1.51 mm−1 |
c = 10.0794 (9) Å | T = 296 K |
β = 105.820 (2)° | Block, yellow |
V = 2339.7 (3) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 4341 independent reflections |
Radiation source: fine-focus sealed tube | 3405 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ϕ and ω scans | θmax = 25.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→11 |
Tmin = 0.732, Tmax = 0.772 | k = −27→29 |
13544 measured reflections | l = −12→12 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0805P)2] where P = (Fo2 + 2Fc2)/3 |
4341 reflections | (Δ/σ)max < 0.001 |
293 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −1.24 e Å−3 |
C22H21FI+·CF3O3S− | V = 2339.7 (3) Å3 |
Mr = 580.37 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.8987 (8) Å | µ = 1.51 mm−1 |
b = 24.374 (2) Å | T = 296 K |
c = 10.0794 (9) Å | 0.22 × 0.20 × 0.18 mm |
β = 105.820 (2)° |
Bruker APEXII CCD diffractometer | 4341 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 3405 reflections with I > 2σ(I) |
Tmin = 0.732, Tmax = 0.772 | Rint = 0.057 |
13544 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.75 e Å−3 |
4341 reflections | Δρmin = −1.24 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 | ||
O1 | 0.3026 (6) | 0.06955 (18) | 0.8802 (5) | 0.0656 (14) | |
C1 | 0.6362 (7) | 0.1152 (2) | 0.6650 (6) | 0.0490 (15) | |
C2 | 0.7058 (6) | 0.1336 (2) | 0.5718 (7) | 0.0533 (16) | |
H2 | 0.7900 | 0.1524 | 0.6045 | 0.064* | |
C3 | 0.6542 (5) | 0.1249 (2) | 0.4321 (6) | 0.0368 (12) | |
C4 | 0.5286 (5) | 0.0968 (2) | 0.3865 (6) | 0.0349 (12) | |
C5 | 0.4560 (6) | 0.0757 (2) | 0.4748 (6) | 0.0375 (12) | |
C6 | 0.5089 (7) | 0.0871 (2) | 0.6182 (6) | 0.0460 (15) | |
H6 | 0.4595 | 0.0760 | 0.6799 | 0.055* | |
C7 | 0.2621 (5) | 0.1271 (2) | 0.1450 (5) | 0.0361 (12) | |
C8 | 0.2661 (6) | 0.1846 (2) | 0.1484 (6) | 0.0419 (13) | |
C9 | 0.1403 (6) | 0.2116 (2) | 0.1369 (7) | 0.0494 (15) | |
H9 | 0.1372 | 0.2497 | 0.1361 | 0.059* | |
C10 | 0.0189 (6) | 0.1814 (3) | 0.1265 (7) | 0.0520 (16) | |
C11 | 0.0135 (6) | 0.1253 (2) | 0.1185 (6) | 0.0456 (14) | |
H11 | −0.0707 | 0.1064 | 0.1055 | 0.055* | |
C12 | 0.1373 (6) | 0.0983 (2) | 0.1305 (6) | 0.0428 (13) | |
H12 | 0.1382 | 0.0601 | 0.1289 | 0.051* | |
C13 | 0.7364 (8) | 0.3215 (3) | 0.1208 (12) | 0.106 (4) | |
H13A | 0.8164 | 0.2994 | 0.1202 | 0.159* | |
H13B | 0.7599 | 0.3457 | 0.1990 | 0.159* | |
H13C | 0.7092 | 0.3428 | 0.0377 | 0.159* | |
C14 | 0.3908 (6) | 0.2173 (2) | 0.1483 (6) | 0.0387 (12) | |
C15 | 0.4525 (6) | 0.2532 (2) | 0.2526 (7) | 0.0495 (15) | |
H15 | 0.4197 | 0.2554 | 0.3305 | 0.059* | |
C16 | 0.5641 (7) | 0.2863 (3) | 0.2419 (8) | 0.0606 (18) | |
H16 | 0.6043 | 0.3101 | 0.3140 | 0.073* | |
C17 | 0.6170 (6) | 0.2852 (3) | 0.1295 (8) | 0.0584 (18) | |
C18 | 0.5565 (7) | 0.2485 (3) | 0.0272 (7) | 0.0573 (17) | |
H18 | 0.5904 | 0.2461 | −0.0500 | 0.069* | |
C19 | 0.4453 (7) | 0.2149 (3) | 0.0362 (7) | 0.0523 (15) | |
H19 | 0.4070 | 0.1905 | −0.0349 | 0.063* | |
C21 | 0.0696 (7) | 0.0300 (3) | 0.7314 (8) | 0.0619 (18) | |
C22 | 0.7369 (6) | 0.1458 (3) | 0.3363 (7) | 0.0537 (16) | |
H22A | 0.7797 | 0.1154 | 0.3026 | 0.080* | |
H22B | 0.8086 | 0.1706 | 0.3855 | 0.080* | |
H22C | 0.6750 | 0.1647 | 0.2600 | 0.080* | |
C23 | 0.6930 (8) | 0.1254 (3) | 0.8169 (7) | 0.071 (2) | |
H23A | 0.7348 | 0.0924 | 0.8617 | 0.107* | |
H23B | 0.6179 | 0.1366 | 0.8544 | 0.107* | |
H23C | 0.7625 | 0.1539 | 0.8318 | 0.107* | |
C24 | 0.3196 (6) | 0.0431 (3) | 0.4328 (7) | 0.0535 (16) | |
H24A | 0.2414 | 0.0679 | 0.4109 | 0.080* | |
H24B | 0.3133 | 0.0197 | 0.5076 | 0.080* | |
H24C | 0.3182 | 0.0210 | 0.3535 | 0.080* | |
F1 | −0.1015 (4) | 0.20869 (18) | 0.1145 (6) | 0.0883 (15) | |
F2 | 0.0066 (6) | −0.0156 (2) | 0.6819 (6) | 0.117 (2) | |
F3 | 0.0720 (5) | 0.0605 (2) | 0.6257 (5) | 0.0839 (13) | |
F4 | −0.0073 (6) | 0.0542 (4) | 0.7991 (7) | 0.147 (3) | |
I1 | 0.44677 (3) | 0.080765 (13) | 0.17435 (3) | 0.03628 (16) | |
O2 | 0.2225 (6) | −0.0155 (2) | 0.9503 (5) | 0.0728 (14) | |
O3 | 0.3103 (5) | −0.01180 (19) | 0.7496 (5) | 0.0687 (14) | |
S3 | 0.24551 (15) | 0.01636 (6) | 0.84096 (15) | 0.0418 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.075 (3) | 0.050 (3) | 0.060 (3) | −0.018 (2) | −0.002 (3) | −0.007 (2) |
C1 | 0.057 (4) | 0.041 (3) | 0.039 (3) | 0.008 (3) | −0.005 (3) | −0.006 (3) |
C2 | 0.044 (3) | 0.042 (3) | 0.063 (4) | −0.001 (3) | −0.004 (3) | −0.010 (3) |
C3 | 0.032 (3) | 0.035 (3) | 0.043 (3) | 0.002 (2) | 0.009 (2) | −0.003 (2) |
C4 | 0.030 (3) | 0.035 (3) | 0.037 (3) | 0.000 (2) | 0.005 (2) | −0.002 (2) |
C5 | 0.031 (3) | 0.041 (3) | 0.042 (3) | 0.009 (2) | 0.013 (2) | 0.002 (2) |
C6 | 0.046 (3) | 0.056 (4) | 0.040 (3) | 0.015 (3) | 0.017 (3) | 0.000 (3) |
C7 | 0.030 (3) | 0.037 (3) | 0.036 (3) | 0.003 (2) | −0.001 (2) | 0.000 (2) |
C8 | 0.043 (3) | 0.034 (3) | 0.040 (3) | 0.000 (2) | −0.002 (3) | 0.001 (2) |
C9 | 0.046 (3) | 0.040 (3) | 0.068 (4) | 0.007 (3) | 0.025 (3) | 0.003 (3) |
C10 | 0.038 (3) | 0.056 (4) | 0.067 (4) | 0.016 (3) | 0.021 (3) | 0.009 (3) |
C11 | 0.028 (3) | 0.051 (4) | 0.054 (4) | −0.003 (3) | 0.006 (3) | 0.007 (3) |
C12 | 0.041 (3) | 0.044 (3) | 0.045 (3) | −0.001 (3) | 0.013 (3) | −0.003 (3) |
C13 | 0.071 (5) | 0.044 (5) | 0.203 (12) | −0.015 (4) | 0.036 (7) | −0.004 (6) |
C14 | 0.034 (3) | 0.038 (3) | 0.043 (3) | 0.008 (2) | 0.008 (2) | 0.001 (2) |
C15 | 0.045 (3) | 0.052 (4) | 0.055 (4) | −0.001 (3) | 0.021 (3) | −0.003 (3) |
C16 | 0.046 (4) | 0.040 (4) | 0.090 (5) | −0.006 (3) | 0.009 (4) | −0.014 (3) |
C17 | 0.040 (3) | 0.037 (3) | 0.100 (6) | 0.002 (3) | 0.023 (4) | 0.005 (3) |
C18 | 0.056 (4) | 0.063 (4) | 0.066 (4) | 0.001 (3) | 0.037 (4) | 0.011 (3) |
C19 | 0.051 (4) | 0.052 (4) | 0.054 (4) | −0.008 (3) | 0.015 (3) | −0.004 (3) |
C21 | 0.039 (3) | 0.074 (5) | 0.068 (5) | 0.001 (3) | 0.006 (3) | 0.003 (4) |
C22 | 0.039 (3) | 0.061 (4) | 0.060 (4) | −0.010 (3) | 0.013 (3) | −0.003 (3) |
C23 | 0.083 (5) | 0.087 (5) | 0.040 (4) | 0.007 (4) | 0.008 (4) | −0.008 (4) |
C24 | 0.039 (3) | 0.056 (4) | 0.061 (4) | −0.005 (3) | 0.006 (3) | 0.011 (3) |
F1 | 0.046 (2) | 0.069 (3) | 0.155 (5) | 0.023 (2) | 0.037 (3) | 0.017 (3) |
F2 | 0.079 (3) | 0.127 (5) | 0.115 (4) | −0.059 (3) | −0.024 (3) | 0.016 (3) |
F3 | 0.072 (3) | 0.094 (3) | 0.073 (3) | 0.004 (3) | −0.002 (2) | 0.029 (3) |
F4 | 0.066 (3) | 0.237 (8) | 0.137 (6) | 0.063 (5) | 0.027 (4) | −0.017 (6) |
I1 | 0.0311 (2) | 0.0377 (2) | 0.0380 (2) | 0.00328 (14) | 0.00587 (16) | −0.00459 (14) |
O2 | 0.097 (4) | 0.078 (3) | 0.048 (3) | −0.016 (3) | 0.026 (3) | 0.014 (2) |
O3 | 0.064 (3) | 0.067 (3) | 0.066 (3) | 0.032 (2) | 0.003 (2) | −0.014 (2) |
S3 | 0.0421 (8) | 0.0415 (8) | 0.0386 (7) | 0.0011 (6) | 0.0056 (6) | −0.0001 (6) |
O1—S3 | 1.427 (4) | C13—H13B | 0.9600 |
C1—C2 | 1.383 (9) | C13—H13C | 0.9600 |
C1—C6 | 1.398 (9) | C14—C15 | 1.377 (8) |
C1—C23 | 1.501 (8) | C14—C19 | 1.380 (8) |
C2—C3 | 1.377 (8) | C15—C16 | 1.395 (9) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.384 (7) | C16—C17 | 1.372 (10) |
C3—C22 | 1.515 (8) | C16—H16 | 0.9300 |
C4—C5 | 1.387 (8) | C17—C18 | 1.372 (10) |
C4—I1 | 2.107 (5) | C18—C19 | 1.395 (9) |
C5—C6 | 1.424 (8) | C18—H18 | 0.9300 |
C5—C24 | 1.524 (8) | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C21—F4 | 1.294 (9) |
C7—C12 | 1.393 (8) | C21—F3 | 1.304 (8) |
C7—C8 | 1.403 (8) | C21—F2 | 1.306 (9) |
C7—I1 | 2.099 (5) | C21—S3 | 1.820 (7) |
C8—C9 | 1.384 (8) | C22—H22A | 0.9600 |
C8—C14 | 1.469 (8) | C22—H22B | 0.9600 |
C9—C10 | 1.389 (8) | C22—H22C | 0.9600 |
C9—H9 | 0.9300 | C23—H23A | 0.9600 |
C10—F1 | 1.342 (7) | C23—H23B | 0.9600 |
C10—C11 | 1.369 (9) | C23—H23C | 0.9600 |
C11—C12 | 1.367 (8) | C24—H24A | 0.9600 |
C11—H11 | 0.9300 | C24—H24B | 0.9600 |
C12—H12 | 0.9300 | C24—H24C | 0.9600 |
C13—C17 | 1.499 (9) | O2—S3 | 1.416 (5) |
C13—H13A | 0.9600 | O3—S3 | 1.433 (5) |
C2—C1—C6 | 120.0 (5) | C14—C15—H15 | 119.9 |
C2—C1—C23 | 121.4 (6) | C16—C15—H15 | 119.9 |
C6—C1—C23 | 118.6 (6) | C17—C16—C15 | 122.8 (6) |
C3—C2—C1 | 122.0 (5) | C17—C16—H16 | 118.6 |
C3—C2—H2 | 119.0 | C15—C16—H16 | 118.6 |
C1—C2—H2 | 119.0 | C16—C17—C18 | 116.5 (6) |
C2—C3—C4 | 117.7 (5) | C16—C17—C13 | 121.4 (8) |
C2—C3—C22 | 119.1 (5) | C18—C17—C13 | 122.1 (8) |
C4—C3—C22 | 123.2 (5) | C17—C18—C19 | 121.6 (6) |
C3—C4—C5 | 123.2 (5) | C17—C18—H18 | 119.2 |
C3—C4—I1 | 119.4 (4) | C19—C18—H18 | 119.2 |
C5—C4—I1 | 117.4 (4) | C14—C19—C18 | 121.4 (6) |
C4—C5—C6 | 117.8 (5) | C14—C19—H19 | 119.3 |
C4—C5—C24 | 126.2 (5) | C18—C19—H19 | 119.3 |
C6—C5—C24 | 115.9 (5) | F4—C21—F3 | 108.4 (7) |
C1—C6—C5 | 119.1 (6) | F4—C21—F2 | 107.5 (7) |
C1—C6—H6 | 120.4 | F3—C21—F2 | 106.6 (6) |
C5—C6—H6 | 120.4 | F4—C21—S3 | 111.5 (5) |
C12—C7—C8 | 121.6 (5) | F3—C21—S3 | 111.8 (5) |
C12—C7—I1 | 117.2 (4) | F2—C21—S3 | 110.7 (5) |
C8—C7—I1 | 121.1 (4) | C3—C22—H22A | 109.5 |
C9—C8—C7 | 117.0 (5) | C3—C22—H22B | 109.5 |
C9—C8—C14 | 118.6 (5) | H22A—C22—H22B | 109.5 |
C7—C8—C14 | 124.0 (5) | C3—C22—H22C | 109.5 |
C8—C9—C10 | 119.6 (5) | H22A—C22—H22C | 109.5 |
C8—C9—H9 | 120.2 | H22B—C22—H22C | 109.5 |
C10—C9—H9 | 120.2 | C1—C23—H23A | 109.5 |
F1—C10—C11 | 118.1 (6) | C1—C23—H23B | 109.5 |
F1—C10—C9 | 118.2 (5) | H23A—C23—H23B | 109.5 |
C11—C10—C9 | 123.6 (5) | C1—C23—H23C | 109.5 |
C12—C11—C10 | 117.1 (5) | H23A—C23—H23C | 109.5 |
C12—C11—H11 | 121.4 | H23B—C23—H23C | 109.5 |
C10—C11—H11 | 121.4 | C5—C24—H24A | 109.5 |
C11—C12—C7 | 121.0 (5) | C5—C24—H24B | 109.5 |
C11—C12—H12 | 119.5 | H24A—C24—H24B | 109.5 |
C7—C12—H12 | 119.5 | C5—C24—H24C | 109.5 |
C17—C13—H13A | 109.5 | H24A—C24—H24C | 109.5 |
C17—C13—H13B | 109.5 | H24B—C24—H24C | 109.5 |
H13A—C13—H13B | 109.5 | C7—I1—C4 | 97.0 (2) |
C17—C13—H13C | 109.5 | O2—S3—O1 | 114.7 (3) |
H13A—C13—H13C | 109.5 | O2—S3—O3 | 115.7 (3) |
H13B—C13—H13C | 109.5 | O1—S3—O3 | 113.6 (3) |
C15—C14—C19 | 117.4 (5) | O2—S3—C21 | 104.0 (3) |
C15—C14—C8 | 122.9 (5) | O1—S3—C21 | 104.1 (3) |
C19—C14—C8 | 119.6 (5) | O3—S3—C21 | 102.7 (3) |
C14—C15—C16 | 120.3 (6) | ||
C6—C1—C2—C3 | −0.4 (9) | I1—C7—C12—C11 | 176.4 (4) |
C23—C1—C2—C3 | −179.4 (6) | C9—C8—C14—C15 | 66.3 (8) |
C1—C2—C3—C4 | 0.0 (9) | C7—C8—C14—C15 | −120.6 (7) |
C1—C2—C3—C22 | −179.4 (6) | C9—C8—C14—C19 | −109.7 (7) |
C2—C3—C4—C5 | −2.2 (8) | C7—C8—C14—C19 | 63.4 (8) |
C22—C3—C4—C5 | 177.2 (5) | C19—C14—C15—C16 | 1.1 (9) |
C2—C3—C4—I1 | −178.6 (4) | C8—C14—C15—C16 | −175.0 (5) |
C22—C3—C4—I1 | 0.7 (7) | C14—C15—C16—C17 | 0.3 (10) |
C3—C4—C5—C6 | 4.6 (8) | C15—C16—C17—C18 | −1.4 (10) |
I1—C4—C5—C6 | −178.9 (4) | C15—C16—C17—C13 | 179.5 (6) |
C3—C4—C5—C24 | −178.3 (5) | C16—C17—C18—C19 | 1.1 (10) |
I1—C4—C5—C24 | −1.8 (7) | C13—C17—C18—C19 | −179.9 (7) |
C2—C1—C6—C5 | 2.9 (8) | C15—C14—C19—C18 | −1.4 (9) |
C23—C1—C6—C5 | −178.2 (6) | C8—C14—C19—C18 | 174.8 (6) |
C4—C5—C6—C1 | −4.8 (8) | C17—C18—C19—C14 | 0.3 (10) |
C24—C5—C6—C1 | 177.8 (5) | C12—C7—I1—C4 | −105.0 (4) |
C12—C7—C8—C9 | 0.1 (9) | C8—C7—I1—C4 | 71.2 (5) |
I1—C7—C8—C9 | −176.0 (4) | C3—C4—I1—C7 | −116.7 (4) |
C12—C7—C8—C14 | −173.1 (5) | C5—C4—I1—C7 | 66.6 (4) |
I1—C7—C8—C14 | 10.9 (8) | F4—C21—S3—O2 | 56.9 (7) |
C7—C8—C9—C10 | 1.7 (9) | F3—C21—S3—O2 | 178.5 (5) |
C14—C8—C9—C10 | 175.3 (6) | F2—C21—S3—O2 | −62.7 (6) |
C8—C9—C10—F1 | −179.5 (6) | F4—C21—S3—O1 | −63.5 (7) |
C8—C9—C10—C11 | −4.1 (11) | F3—C21—S3—O1 | 58.1 (6) |
F1—C10—C11—C12 | 179.7 (6) | F2—C21—S3—O1 | 176.9 (6) |
C9—C10—C11—C12 | 4.3 (10) | F4—C21—S3—O3 | 177.8 (7) |
C10—C11—C12—C7 | −2.3 (9) | F3—C21—S3—O3 | −60.6 (6) |
C8—C7—C12—C11 | 0.2 (9) | F2—C21—S3—O3 | 58.2 (6) |
Cg3 is the centroid of the C14–C19 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···F1i | 0.96 | 2.36 | 3.193 (9) | 145 |
C22—H22C···Cg3ii | 0.96 | 2.76 | 3.648 (7) | 154 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y+1/2, −z+1/2. |
Cg3 is the centroid of the C14–C19 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···F1i | 0.96 | 2.36 | 3.193 (9) | 145 |
C22—H22C···Cg3ii | 0.96 | 2.76 | 3.648 (7) | 154 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y+1/2, −z+1/2. |
Acknowledgements
We gratefully acknowledge the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), the National Natural Science Foundation of China (grant No. 21302015), and the Natural Science Fundation for Colleges and Universities of Jiangsu Province (grant No. 12KJB150005) for financial support.
References
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Grushin, V. V. (2000). Chem. Soc. Rev. 29, 315–324. Web of Science CrossRef CAS Google Scholar
Merritt, E. A. & Olofsson, B. (2009). Angew. Chem. Int. Ed. 48, 9052–9070. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The use of diaryliodonium salts has recently gained considerable attention in organic synthesis for arylation of organic bases (Merritt et al., 2009; Grushin et al., 2000). The title compound (Fig. 1) is an important representative of such reagents. In the molecule of the compound, the iodine atom lies almost in the plane of both attached benzene rings with r.m.s. deviations of 0.012 (2) Å and 0.028 (1) Å from the C1—C6 and C7—C12 mean planes respectively. The dihedral angle between the rings of the biphenyl group is 65.6 (1)°. The ring of the mesitylene group is inclined to the phenyl rings of the biphenyl group by 93.9 (2)° (for fluorobenzene ring) and 22.4 (2)° (for toluene ring). Extremely short intermolecular I···O contacts [2.93 (5) and 2.86 (6) Å] occur, due to strong electrostatic interactions between the I atom and two adjacent trifluoromethanesulfonate counter-ions. There are also C—H···F and C—H···π hydrogen bonds present (contact distances are shown in Table 1), which combined with the other inter-actions, form a three-dimensional network (Fig. 2).