Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036379/hb2492sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036379/hb2492Isup2.hkl |
CCDC reference: 657875
Sodium perborate tetrahydrate (35.39 g, 230 mmol) was added in batches to a stirred mixture of 2-iodo-4-methylanisole (5.71 g, 23 mmol) in acetic acid (100 ml) and acetic anhydride (50 ml) at 318 K. The suspension was stirred for 4.5 h at 318 K, diluted with 600 ml of water and extracted three times with dichloromethane. The organic extracts were dried with sodium sulfate, the solvent removed in vacuum and the residue crystallized from diethyl ether to obtain 2-methoxy-5-methylbis(acetoxy)iodobenzene.
Trifluoromethanesulfonic acid (0.63 ml, 8.2 mmol) was added dropwise to a stirred suspension of this product (1.5 g, 4.1 mmol) in dichloromethane (50 ml) at 263 K under nitrogen. The mixture was stirred for 30 min at 263 K, then at room temperature for a further 1.5 h, cooled to 263 K and 3-methylanisole (0.50 g, 4.1 mmol) added dropwise via syringe. The mixture was stirred at 263 K for 1 h and then at room temperature overnight, solvent was removed in vacuum and the residue crystallized from diethyl ether. Crystals suitable for X-ray analysis were obtained by slow evaporation in dichloromethane solution.
The fluorine atoms in the CF3 group were found to be disordered over two positions. Their occupancy factors refined to 0.512 (18) and 0.488 (18) respectively. The C—F distance was restrained to 1.37 (1) Å.
All the H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Diaryliodonium salts are useful in organic synthesis for arylation of organic and inorganic bases (Shah et al., 1997; Shah et al., 1998). The title compound, (I), (Fig. 1), is an important representative of such reagents. The iodine atom lies almost in the plane of both attached benzene rings with r.m.s. deviations of 0.022 (3) Å and 0.015 (3) Å from the C1—C6 and C9—C14 mean planes respectively. These rings are nearly orthogonal with a dihedral angle between them of 87.76 (5) °.
Each iodine atom interacts with two O atoms from adjacent trifloroacetate anions. Inversion symmetry then generates cyclic units (Fig. 2). Similar interactions have been observed previously in iodonium salts (Li & Jiang, 2007). The distances I1—O3i and I1—O3ii (i = x - 1, y + 1, z; ii = 1 - x, 1 - y, -z) in (I) are 3.019 (13) and 2.807 (9) Å, respectively.
For related literature, see: Shah et al. (1997, 1998); Li & Jiang (2007).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C16H18IO2+·C2F3O2− | Z = 2 |
Mr = 482.22 | F(000) = 476 |
Triclinic, P1 | Dx = 1.626 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.211 (4) Å | Cell parameters from 2102 reflections |
b = 11.182 (6) Å | θ = 2.4–24.9° |
c = 12.200 (6) Å | µ = 1.67 mm−1 |
α = 93.690 (8)° | T = 294 K |
β = 107.874 (7)° | Block, colourless |
γ = 109.841 (8)° | 0.20 × 0.18 × 0.14 mm |
V = 984.9 (8) Å3 |
Bruker SMART 1000 CCD area-detector diffractometer | 3425 independent reflections |
Radiation source: fine-focus sealed tube | 2356 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→8 |
Tmin = 0.731, Tmax = 0.800 | k = −13→13 |
4842 measured reflections | l = −8→14 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0996P)2 + 1.2747P] where P = (Fo2 + 2Fc2)/3 |
3425 reflections | (Δ/σ)max = 0.004 |
267 parameters | Δρmax = 1.20 e Å−3 |
72 restraints | Δρmin = −0.78 e Å−3 |
C16H18IO2+·C2F3O2− | γ = 109.841 (8)° |
Mr = 482.22 | V = 984.9 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.211 (4) Å | Mo Kα radiation |
b = 11.182 (6) Å | µ = 1.67 mm−1 |
c = 12.200 (6) Å | T = 294 K |
α = 93.690 (8)° | 0.20 × 0.18 × 0.14 mm |
β = 107.874 (7)° |
Bruker SMART 1000 CCD area-detector diffractometer | 3425 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2356 reflections with I > 2σ(I) |
Tmin = 0.731, Tmax = 0.800 | Rint = 0.026 |
4842 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 72 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.01 | Δρmax = 1.20 e Å−3 |
3425 reflections | Δρmin = −0.78 e Å−3 |
267 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) | |
I1 | 0.19140 (9) | 0.97059 (6) | 0.12590 (4) | 0.0615 (3) | |
O1 | 0.6312 (9) | 0.6100 (7) | 0.1571 (7) | 0.082 (2) | |
O2 | 0.1034 (10) | 0.8681 (8) | 0.3388 (6) | 0.079 (2) | |
C1 | 0.3292 (11) | 0.8419 (7) | 0.1341 (6) | 0.0426 (18) | |
C2 | 0.5130 (12) | 0.8923 (9) | 0.1423 (8) | 0.057 (2) | |
H2 | 0.5706 | 0.9802 | 0.1440 | 0.068* | |
C3 | 0.6100 (12) | 0.8126 (10) | 0.1480 (9) | 0.065 (2) | |
H3 | 0.7324 | 0.8454 | 0.1520 | 0.078* | |
C4 | 0.5232 (11) | 0.6840 (9) | 0.1477 (8) | 0.054 (2) | |
C5 | 0.3393 (11) | 0.6320 (8) | 0.1396 (7) | 0.0465 (18) | |
H5 | 0.2836 | 0.5442 | 0.1388 | 0.056* | |
C6 | 0.2382 (10) | 0.7105 (8) | 0.1327 (6) | 0.0452 (19) | |
C7 | 0.0350 (12) | 0.6463 (10) | 0.1190 (10) | 0.074 (3) | |
H7A | 0.0033 | 0.5549 | 0.1161 | 0.111* | |
H7B | −0.0404 | 0.6607 | 0.0477 | 0.111* | |
H7C | 0.0143 | 0.6827 | 0.1844 | 0.111* | |
C8 | 0.5516 (17) | 0.4762 (11) | 0.1592 (13) | 0.096 (4) | |
H8A | 0.5154 | 0.4663 | 0.2269 | 0.144* | |
H8B | 0.6405 | 0.4374 | 0.1627 | 0.144* | |
H8C | 0.4450 | 0.4346 | 0.0895 | 0.144* | |
C9 | 0.3077 (12) | 1.0572 (9) | 0.3044 (7) | 0.055 (2) | |
C10 | 0.2357 (14) | 0.9876 (11) | 0.3836 (7) | 0.063 (2) | |
C11 | 0.3145 (17) | 1.0517 (13) | 0.5011 (8) | 0.080 (3) | |
H11 | 0.2757 | 1.0099 | 0.5573 | 0.096* | |
C12 | 0.4429 (16) | 1.1706 (13) | 0.5338 (8) | 0.079 (3) | |
H12 | 0.4872 | 1.2099 | 0.6122 | 0.095* | |
C13 | 0.5142 (16) | 1.2393 (12) | 0.4585 (10) | 0.084 (4) | |
C14 | 0.4398 (14) | 1.1769 (10) | 0.3386 (9) | 0.066 (3) | |
H14 | 0.4828 | 1.2191 | 0.2838 | 0.079* | |
C15 | 0.658 (2) | 1.3747 (12) | 0.4951 (13) | 0.119 (5) | |
H15A | 0.6070 | 1.4332 | 0.5185 | 0.179* | |
H15B | 0.6967 | 1.3997 | 0.4304 | 0.179* | |
H15C | 0.7627 | 1.3777 | 0.5597 | 0.179* | |
C16 | 0.0146 (19) | 0.8018 (14) | 0.4130 (12) | 0.107 (4) | |
H16A | 0.1041 | 0.7881 | 0.4775 | 0.161* | |
H16B | −0.0786 | 0.7198 | 0.3691 | 0.161* | |
H16C | −0.0418 | 0.8528 | 0.4423 | 0.161* | |
F1 | 0.964 (3) | 0.3874 (13) | 0.2500 (18) | 0.143 (8) | 0.488 (18) |
F2 | 0.813 (2) | 0.208 (2) | 0.282 (2) | 0.167 (9) | 0.488 (18) |
F3 | 1.101 (2) | 0.2949 (18) | 0.3656 (11) | 0.124 (7) | 0.488 (18) |
F1' | 0.794 (2) | 0.267 (2) | 0.2015 (18) | 0.157 (9) | 0.512 (18) |
F2' | 0.924 (3) | 0.1712 (17) | 0.3198 (16) | 0.153 (8) | 0.512 (18) |
F3' | 1.052 (4) | 0.3757 (18) | 0.336 (2) | 0.269 (18) | 0.512 (18) |
C17 | 1.0118 (16) | 0.2125 (12) | 0.1657 (9) | 0.068 (3) | |
C18 | 0.9657 (16) | 0.2663 (10) | 0.2565 (10) | 0.110 (4) | |
O3 | 0.9273 (16) | 0.1057 (9) | 0.1183 (8) | 0.115 (3) | |
O4 | 1.1470 (18) | 0.2865 (18) | 0.1514 (14) | 0.210 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0862 (5) | 0.0779 (5) | 0.0292 (3) | 0.0555 (4) | 0.0053 (3) | 0.0064 (2) |
O1 | 0.063 (4) | 0.072 (5) | 0.125 (7) | 0.042 (4) | 0.033 (4) | 0.019 (4) |
O2 | 0.085 (5) | 0.092 (5) | 0.046 (4) | 0.022 (4) | 0.016 (4) | 0.010 (4) |
C1 | 0.054 (5) | 0.045 (5) | 0.032 (4) | 0.027 (4) | 0.010 (3) | 0.008 (3) |
C2 | 0.057 (6) | 0.054 (5) | 0.059 (5) | 0.019 (4) | 0.022 (4) | 0.008 (4) |
C3 | 0.046 (5) | 0.069 (7) | 0.082 (7) | 0.020 (5) | 0.027 (5) | 0.014 (5) |
C4 | 0.045 (5) | 0.060 (6) | 0.059 (5) | 0.027 (4) | 0.013 (4) | 0.009 (4) |
C5 | 0.050 (5) | 0.048 (5) | 0.042 (4) | 0.021 (4) | 0.014 (4) | 0.006 (4) |
C6 | 0.038 (4) | 0.065 (6) | 0.033 (4) | 0.025 (4) | 0.008 (3) | 0.003 (3) |
C7 | 0.048 (5) | 0.071 (7) | 0.091 (7) | 0.018 (5) | 0.018 (5) | −0.007 (5) |
C8 | 0.108 (9) | 0.078 (8) | 0.138 (12) | 0.064 (7) | 0.056 (9) | 0.035 (7) |
C9 | 0.069 (6) | 0.065 (6) | 0.033 (4) | 0.046 (5) | 0.001 (4) | 0.008 (4) |
C10 | 0.075 (6) | 0.092 (8) | 0.034 (4) | 0.053 (6) | 0.012 (4) | 0.009 (5) |
C11 | 0.100 (8) | 0.122 (10) | 0.039 (5) | 0.072 (8) | 0.019 (6) | 0.014 (6) |
C12 | 0.096 (8) | 0.105 (9) | 0.027 (5) | 0.050 (7) | 0.001 (5) | −0.011 (5) |
C13 | 0.089 (7) | 0.087 (8) | 0.055 (6) | 0.048 (7) | −0.013 (6) | −0.026 (6) |
C14 | 0.081 (7) | 0.061 (6) | 0.056 (5) | 0.043 (6) | 0.007 (5) | 0.002 (5) |
C15 | 0.131 (11) | 0.078 (9) | 0.116 (11) | 0.037 (8) | 0.009 (9) | −0.015 (8) |
C16 | 0.104 (9) | 0.138 (12) | 0.087 (9) | 0.040 (9) | 0.045 (8) | 0.032 (9) |
F1 | 0.169 (12) | 0.106 (10) | 0.157 (12) | 0.084 (9) | 0.029 (8) | 0.005 (7) |
F2 | 0.150 (11) | 0.206 (14) | 0.164 (13) | 0.053 (8) | 0.104 (10) | 0.006 (8) |
F3 | 0.142 (10) | 0.134 (11) | 0.087 (9) | 0.056 (8) | 0.029 (7) | 0.000 (7) |
F1' | 0.156 (11) | 0.165 (12) | 0.189 (13) | 0.087 (9) | 0.081 (9) | 0.030 (8) |
F2' | 0.177 (12) | 0.185 (12) | 0.108 (10) | 0.052 (8) | 0.078 (9) | 0.050 (8) |
F3' | 0.28 (2) | 0.25 (2) | 0.27 (2) | 0.110 (12) | 0.083 (12) | 0.029 (10) |
C17 | 0.070 (7) | 0.085 (8) | 0.056 (6) | 0.040 (6) | 0.016 (5) | 0.032 (6) |
C18 | 0.140 (13) | 0.081 (9) | 0.095 (10) | 0.028 (9) | 0.044 (10) | −0.008 (7) |
O3 | 0.175 (9) | 0.084 (6) | 0.072 (5) | 0.055 (6) | 0.022 (6) | −0.008 (5) |
O4 | 0.131 (9) | 0.31 (2) | 0.211 (16) | 0.068 (12) | 0.091 (11) | 0.154 (15) |
I1—C1 | 2.101 (7) | C10—C11 | 1.404 (13) |
I1—C9 | 2.102 (8) | C11—C12 | 1.327 (16) |
O1—C4 | 1.390 (10) | C11—H11 | 0.9300 |
O1—C8 | 1.420 (13) | C12—C13 | 1.376 (17) |
O2—C10 | 1.349 (13) | C12—H12 | 0.9300 |
O2—C16 | 1.423 (14) | C13—C14 | 1.426 (14) |
C1—C2 | 1.389 (12) | C13—C15 | 1.504 (18) |
C1—C6 | 1.400 (11) | C14—H14 | 0.9300 |
C2—C3 | 1.375 (12) | C15—H15A | 0.9600 |
C2—H2 | 0.9300 | C15—H15B | 0.9600 |
C3—C4 | 1.371 (13) | C15—H15C | 0.9600 |
C3—H3 | 0.9300 | C16—H16A | 0.9600 |
C4—C5 | 1.391 (12) | C16—H16B | 0.9600 |
C5—C6 | 1.388 (11) | C16—H16C | 0.9600 |
C5—H5 | 0.9300 | F1—C18 | 1.365 (8) |
C6—C7 | 1.526 (12) | F2—C18 | 1.343 (8) |
C7—H7A | 0.9600 | F3—C18 | 1.380 (8) |
C7—H7B | 0.9600 | F1'—C18 | 1.367 (8) |
C7—H7C | 0.9600 | F2'—C18 | 1.366 (8) |
C8—H8A | 0.9600 | F3'—C18 | 1.331 (9) |
C8—H8B | 0.9600 | C17—O3 | 1.159 (13) |
C8—H8C | 0.9600 | C17—O4 | 1.209 (15) |
C9—C14 | 1.344 (14) | C17—C18 | 1.435 (15) |
C9—C10 | 1.422 (14) | ||
C1—I1—C9 | 97.7 (3) | C13—C12—H12 | 118.0 |
C4—O1—C8 | 118.9 (7) | C12—C13—C14 | 116.3 (11) |
C10—O2—C16 | 118.5 (9) | C12—C13—C15 | 124.0 (11) |
C2—C1—C6 | 121.7 (7) | C14—C13—C15 | 119.7 (13) |
C2—C1—I1 | 117.6 (6) | C9—C14—C13 | 120.1 (11) |
C6—C1—I1 | 120.7 (5) | C9—C14—H14 | 119.9 |
C3—C2—C1 | 120.1 (8) | C13—C14—H14 | 119.9 |
C3—C2—H2 | 120.0 | C13—C15—H15A | 109.5 |
C1—C2—H2 | 120.0 | C13—C15—H15B | 109.5 |
C4—C3—C2 | 118.9 (8) | H15A—C15—H15B | 109.5 |
C4—C3—H3 | 120.5 | C13—C15—H15C | 109.5 |
C2—C3—H3 | 120.5 | H15A—C15—H15C | 109.5 |
C3—C4—O1 | 115.7 (7) | H15B—C15—H15C | 109.5 |
C3—C4—C5 | 121.7 (7) | O2—C16—H16A | 109.5 |
O1—C4—C5 | 122.6 (8) | O2—C16—H16B | 109.5 |
C6—C5—C4 | 120.4 (8) | H16A—C16—H16B | 109.5 |
C6—C5—H5 | 119.8 | O2—C16—H16C | 109.5 |
C4—C5—H5 | 119.8 | H16A—C16—H16C | 109.5 |
C5—C6—C1 | 117.3 (7) | H16B—C16—H16C | 109.5 |
C5—C6—C7 | 117.6 (8) | O3—C17—O4 | 126.6 (15) |
C1—C6—C7 | 125.0 (7) | O3—C17—C18 | 120.0 (11) |
C6—C7—H7A | 109.5 | O4—C17—C18 | 113.3 (14) |
C6—C7—H7B | 109.5 | F3'—C18—F2 | 103 (2) |
H7A—C7—H7B | 109.5 | F3'—C18—F1 | 48.9 (12) |
C6—C7—H7C | 109.5 | F2—C18—F1 | 102.0 (12) |
H7A—C7—H7C | 109.5 | F3'—C18—F2' | 104.7 (13) |
H7B—C7—H7C | 109.5 | F2—C18—F2' | 48.5 (11) |
O1—C8—H8A | 109.5 | F1—C18—F2' | 139.8 (16) |
O1—C8—H8B | 109.5 | F3'—C18—F1' | 104.1 (12) |
H8A—C8—H8B | 109.5 | F2—C18—F1' | 53.2 (11) |
O1—C8—H8C | 109.5 | F1—C18—F1' | 66.5 (11) |
H8A—C8—H8C | 109.5 | F2'—C18—F1' | 100.2 (11) |
H8B—C8—H8C | 109.5 | F3'—C18—F3 | 49.9 (12) |
C14—C9—C10 | 122.7 (8) | F2—C18—F3 | 101.0 (11) |
C14—C9—I1 | 119.4 (7) | F1—C18—F3 | 98.4 (10) |
C10—C9—I1 | 117.8 (7) | F2'—C18—F3 | 68.2 (11) |
O2—C10—C11 | 127.4 (10) | F1'—C18—F3 | 142.2 (15) |
O2—C10—C9 | 117.2 (8) | F3'—C18—C17 | 132.8 (17) |
C11—C10—C9 | 115.4 (11) | F2—C18—C17 | 124.5 (13) |
C12—C11—C10 | 121.5 (11) | F1—C18—C17 | 114.4 (12) |
C12—C11—H11 | 119.2 | F2'—C18—C17 | 105.6 (12) |
C10—C11—H11 | 119.2 | F1'—C18—C17 | 105.1 (12) |
C11—C12—C13 | 123.9 (9) | F3—C18—C17 | 112.7 (11) |
C11—C12—H12 | 118.0 | ||
C9—I1—C1—C2 | −76.8 (7) | C14—C9—C10—C11 | −1.1 (12) |
C9—I1—C1—C6 | 102.4 (6) | I1—C9—C10—C11 | −178.1 (6) |
C6—C1—C2—C3 | 0.7 (13) | O2—C10—C11—C12 | −179.2 (9) |
I1—C1—C2—C3 | 180.0 (7) | C9—C10—C11—C12 | 2.1 (14) |
C1—C2—C3—C4 | −1.3 (14) | C10—C11—C12—C13 | −2.3 (17) |
C2—C3—C4—O1 | −178.2 (9) | C11—C12—C13—C14 | 1.3 (16) |
C2—C3—C4—C5 | 1.2 (15) | C11—C12—C13—C15 | 179.3 (11) |
C8—O1—C4—C3 | 179.0 (10) | C10—C9—C14—C13 | 0.2 (13) |
C8—O1—C4—C5 | −0.4 (14) | I1—C9—C14—C13 | 177.2 (7) |
C3—C4—C5—C6 | −0.6 (13) | C12—C13—C14—C9 | −0.2 (14) |
O1—C4—C5—C6 | 178.7 (8) | C15—C13—C14—C9 | −178.3 (10) |
C4—C5—C6—C1 | 0.1 (11) | O3—C17—C18—F3' | 168.4 (17) |
C4—C5—C6—C7 | 177.6 (8) | O4—C17—C18—F3' | −8 (2) |
C2—C1—C6—C5 | −0.1 (11) | O3—C17—C18—F2 | −9.8 (19) |
I1—C1—C6—C5 | −179.4 (5) | O4—C17—C18—F2 | 173.7 (16) |
C2—C1—C6—C7 | −177.4 (9) | O3—C17—C18—F1 | −135.9 (13) |
I1—C1—C6—C7 | 3.4 (11) | O4—C17—C18—F1 | 47.6 (15) |
C1—I1—C9—C14 | 104.3 (7) | O3—C17—C18—F2' | 40.2 (15) |
C1—I1—C9—C10 | −78.6 (7) | O4—C17—C18—F2' | −136.3 (13) |
C16—O2—C10—C11 | 8.0 (15) | O3—C17—C18—F1' | −65.2 (14) |
C16—O2—C10—C9 | −173.3 (9) | O4—C17—C18—F1' | 118.3 (14) |
C14—C9—C10—O2 | −180.0 (8) | O3—C17—C18—F3 | 112.7 (13) |
I1—C9—C10—O2 | 3.0 (10) | O4—C17—C18—F3 | −63.8 (14) |
Experimental details
Crystal data | |
Chemical formula | C16H18IO2+·C2F3O2− |
Mr | 482.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 8.211 (4), 11.182 (6), 12.200 (6) |
α, β, γ (°) | 93.690 (8), 107.874 (7), 109.841 (8) |
V (Å3) | 984.9 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.67 |
Crystal size (mm) | 0.20 × 0.18 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.731, 0.800 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4842, 3425, 2356 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.169, 1.01 |
No. of reflections | 3425 |
No. of parameters | 267 |
No. of restraints | 72 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.20, −0.78 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
Diaryliodonium salts are useful in organic synthesis for arylation of organic and inorganic bases (Shah et al., 1997; Shah et al., 1998). The title compound, (I), (Fig. 1), is an important representative of such reagents. The iodine atom lies almost in the plane of both attached benzene rings with r.m.s. deviations of 0.022 (3) Å and 0.015 (3) Å from the C1—C6 and C9—C14 mean planes respectively. These rings are nearly orthogonal with a dihedral angle between them of 87.76 (5) °.
Each iodine atom interacts with two O atoms from adjacent trifloroacetate anions. Inversion symmetry then generates cyclic units (Fig. 2). Similar interactions have been observed previously in iodonium salts (Li & Jiang, 2007). The distances I1—O3i and I1—O3ii (i = x - 1, y + 1, z; ii = 1 - x, 1 - y, -z) in (I) are 3.019 (13) and 2.807 (9) Å, respectively.