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The asymmetric unit of the title compound C15H16IO2+·CF3CO2-, comprises an iodonium cation and a trifluoroacetate anion. The benzene rings are inclined at an angle of 87.76 (5)° to one another. There is evidence for strong electrostatic interactions between the I atom and two adjacent trifluoroacetate counter-ions.
Supporting information
CCDC reference: 634001
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.035
- wR factor = 0.079
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT431_ALERT_2_A Short Inter HL..A Contact I1 .. O3 .. 2.86 Ang.
| Author Response: These are due to strong electrostatic intetactions between the
cation and anion in the structure.
|
PLAT431_ALERT_2_A Short Inter HL..A Contact I1 .. O4 .. 2.96 Ang.
| Author Response: These are due to strong electrostatic intetactions between the
cation and anion in the structure.
|
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C16
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C17
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 30.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact I1 .. O3 .. 3.32 Ang.
| Author Response: These are due to strong electrostatic intetactions between the
cation and anion in the structure.
|
PLAT432_ALERT_2_C Short Inter X...Y Contact I1 .. C16 .. 3.45 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact F1 .. C7 .. 2.91 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.00 Deg.
F3 -C17 -F3' 1.555 1.555 1.555
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.
(2-Methoxy-5-methylphenyl)(4-methoxyphenyl)iodonium trifluoroacetate
top
Crystal data top
C15H16IO2+·C2F3O2− | F(000) = 920 |
Mr = 468.20 | Dx = 1.696 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2446 reflections |
a = 12.805 (3) Å | θ = 2.4–23.6° |
b = 10.620 (2) Å | µ = 1.79 mm−1 |
c = 14.334 (3) Å | T = 294 K |
β = 109.803 (3)° | Block, colorless |
V = 1833.9 (6) Å3 | 0.26 × 0.24 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 3744 independent reflections |
Radiation source: fine-focus sealed tube | 2099 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→15 |
Tmin = 0.644, Tmax = 0.716 | k = −10→13 |
10107 measured reflections | l = −17→15 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0273P)2 + 0.6825P] where P = (Fo2 + 2Fc2)/3 |
3744 reflections | (Δ/σ)max = 0.001 |
257 parameters | Δρmax = 0.70 e Å−3 |
78 restraints | Δρmin = −0.44 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
I1 | 0.83685 (2) | 0.49497 (3) | 0.47230 (2) | 0.06367 (13) | |
O1 | 0.6711 (3) | 0.3792 (3) | 0.5599 (3) | 0.0845 (10) | |
O2 | 0.4356 (3) | 0.4838 (3) | 0.0809 (2) | 0.0797 (9) | |
O3 | 0.9461 (3) | 0.3993 (3) | 0.3430 (2) | 0.0853 (10) | |
O4 | 1.0299 (3) | 0.5736 (4) | 0.3214 (3) | 0.1062 (13) | |
C1 | 0.7454 (3) | 0.5791 (5) | 0.5524 (3) | 0.0563 (11) | |
C2 | 0.6744 (3) | 0.5034 (5) | 0.5827 (3) | 0.0629 (11) | |
C3 | 0.6124 (4) | 0.5621 (5) | 0.6334 (3) | 0.0693 (13) | |
H3 | 0.5638 | 0.5151 | 0.6552 | 0.083* | |
C4 | 0.6231 (4) | 0.6901 (5) | 0.6513 (3) | 0.0719 (14) | |
H4 | 0.5818 | 0.7269 | 0.6865 | 0.086* | |
C5 | 0.6918 (4) | 0.7661 (5) | 0.6197 (3) | 0.0647 (12) | |
C6 | 0.7542 (3) | 0.7067 (4) | 0.5696 (3) | 0.0605 (12) | |
H6 | 0.8023 | 0.7539 | 0.5475 | 0.073* | |
C7 | 0.6020 (4) | 0.2956 (5) | 0.5929 (4) | 0.0999 (18) | |
H7A | 0.5262 | 0.3230 | 0.5664 | 0.150* | |
H7B | 0.6259 | 0.2964 | 0.6640 | 0.150* | |
H7C | 0.6080 | 0.2117 | 0.5703 | 0.150* | |
C8 | 0.6969 (4) | 0.9059 (5) | 0.6354 (4) | 0.0911 (16) | |
H8A | 0.6803 | 0.9253 | 0.6943 | 0.137* | |
H8B | 0.6436 | 0.9461 | 0.5794 | 0.137* | |
H8C | 0.7700 | 0.9356 | 0.6425 | 0.137* | |
C9 | 0.7025 (3) | 0.4896 (4) | 0.3381 (3) | 0.0491 (9) | |
C10 | 0.6579 (4) | 0.6001 (4) | 0.2917 (3) | 0.0623 (12) | |
H10 | 0.6880 | 0.6772 | 0.3183 | 0.075* | |
C11 | 0.5679 (4) | 0.5950 (4) | 0.2050 (3) | 0.0673 (13) | |
H11 | 0.5362 | 0.6690 | 0.1732 | 0.081* | |
C12 | 0.5253 (3) | 0.4799 (4) | 0.1659 (3) | 0.0565 (11) | |
C13 | 0.5713 (3) | 0.3693 (4) | 0.2122 (3) | 0.0588 (11) | |
H13 | 0.5425 | 0.2920 | 0.1850 | 0.071* | |
C14 | 0.6608 (3) | 0.3749 (4) | 0.2998 (3) | 0.0556 (11) | |
H14 | 0.6924 | 0.3012 | 0.3323 | 0.067* | |
C15 | 0.3905 (4) | 0.3664 (5) | 0.0365 (4) | 0.1022 (18) | |
H15A | 0.3633 | 0.3201 | 0.0811 | 0.153* | |
H15B | 0.4473 | 0.3184 | 0.0229 | 0.153* | |
H15C | 0.3306 | 0.3818 | −0.0243 | 0.153* | |
C16 | 0.9681 (4) | 0.4834 (5) | 0.2931 (3) | 0.0616 (12) | |
C17 | 0.9126 (4) | 0.4741 (4) | 0.1821 (4) | 0.0684 (13) | |
F1 | 0.9646 (4) | 0.3923 (5) | 0.1437 (3) | 0.1214 (19) | 0.881 (7) |
F2 | 0.8092 (3) | 0.4274 (5) | 0.1544 (3) | 0.1075 (18) | 0.881 (7) |
F3 | 0.9058 (5) | 0.5807 (4) | 0.1324 (3) | 0.1080 (17) | 0.881 (7) |
F1' | 0.885 (3) | 0.3617 (17) | 0.137 (2) | 0.108 (11) | 0.119 (7) |
F2' | 0.8181 (15) | 0.545 (2) | 0.1626 (15) | 0.065 (8) | 0.119 (7) |
F3' | 0.966 (2) | 0.531 (3) | 0.1278 (17) | 0.077 (9) | 0.119 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.04634 (16) | 0.0873 (2) | 0.06048 (18) | −0.00048 (18) | 0.02217 (12) | −0.00776 (18) |
O1 | 0.089 (3) | 0.069 (2) | 0.109 (3) | −0.011 (2) | 0.052 (2) | 0.001 (2) |
O2 | 0.069 (2) | 0.090 (3) | 0.068 (2) | 0.002 (2) | 0.0075 (16) | −0.0010 (19) |
O3 | 0.112 (3) | 0.074 (2) | 0.081 (2) | 0.022 (2) | 0.046 (2) | 0.010 (2) |
O4 | 0.119 (3) | 0.083 (3) | 0.089 (3) | −0.011 (2) | −0.002 (2) | −0.013 (2) |
C1 | 0.045 (2) | 0.076 (3) | 0.053 (3) | 0.002 (2) | 0.023 (2) | −0.001 (2) |
C2 | 0.053 (2) | 0.075 (3) | 0.064 (3) | −0.001 (3) | 0.024 (2) | 0.002 (3) |
C3 | 0.063 (3) | 0.086 (4) | 0.072 (3) | 0.003 (3) | 0.039 (3) | 0.018 (3) |
C4 | 0.067 (3) | 0.090 (4) | 0.071 (3) | 0.009 (3) | 0.039 (3) | 0.002 (3) |
C5 | 0.060 (3) | 0.079 (4) | 0.055 (3) | 0.000 (3) | 0.019 (2) | −0.007 (2) |
C6 | 0.059 (3) | 0.072 (3) | 0.052 (3) | −0.011 (2) | 0.021 (2) | −0.003 (2) |
C7 | 0.115 (4) | 0.080 (4) | 0.107 (4) | −0.022 (4) | 0.040 (4) | 0.014 (3) |
C8 | 0.098 (4) | 0.082 (4) | 0.101 (4) | −0.008 (3) | 0.045 (3) | −0.022 (3) |
C9 | 0.048 (2) | 0.052 (3) | 0.051 (2) | 0.000 (2) | 0.0217 (18) | −0.002 (2) |
C10 | 0.074 (3) | 0.047 (3) | 0.070 (3) | −0.004 (2) | 0.030 (3) | −0.006 (2) |
C11 | 0.078 (3) | 0.052 (3) | 0.072 (3) | 0.009 (3) | 0.026 (3) | 0.010 (3) |
C12 | 0.053 (2) | 0.062 (3) | 0.058 (3) | −0.003 (2) | 0.024 (2) | −0.004 (2) |
C13 | 0.059 (3) | 0.055 (3) | 0.065 (3) | −0.009 (2) | 0.024 (2) | −0.008 (2) |
C14 | 0.057 (3) | 0.048 (3) | 0.065 (3) | 0.003 (2) | 0.024 (2) | 0.006 (2) |
C15 | 0.086 (4) | 0.119 (5) | 0.079 (4) | −0.017 (4) | −0.001 (3) | −0.013 (4) |
C16 | 0.065 (3) | 0.050 (3) | 0.068 (3) | 0.012 (3) | 0.020 (2) | −0.007 (3) |
C17 | 0.069 (3) | 0.064 (4) | 0.076 (3) | 0.000 (3) | 0.028 (3) | −0.009 (3) |
F1 | 0.135 (4) | 0.137 (4) | 0.102 (3) | 0.029 (3) | 0.054 (3) | −0.040 (2) |
F2 | 0.080 (3) | 0.136 (4) | 0.097 (3) | −0.028 (3) | 0.018 (2) | −0.008 (3) |
F3 | 0.135 (4) | 0.084 (3) | 0.089 (3) | −0.009 (3) | 0.017 (3) | 0.019 (2) |
F1' | 0.110 (14) | 0.104 (14) | 0.110 (13) | −0.007 (9) | 0.036 (9) | −0.004 (9) |
F2' | 0.057 (11) | 0.084 (12) | 0.056 (10) | 0.028 (8) | 0.021 (7) | 0.005 (8) |
F3' | 0.084 (11) | 0.084 (13) | 0.068 (11) | −0.008 (8) | 0.035 (8) | 0.014 (8) |
Geometric parameters (Å, º) top
I1—C1 | 2.097 (4) | C8—H8B | 0.9600 |
I1—C9 | 2.102 (4) | C8—H8C | 0.9600 |
O1—C2 | 1.357 (5) | C9—C14 | 1.369 (5) |
O1—C7 | 1.441 (5) | C9—C10 | 1.373 (5) |
O2—C12 | 1.363 (5) | C10—C11 | 1.380 (5) |
O2—C15 | 1.430 (5) | C10—H10 | 0.9300 |
O3—C16 | 1.235 (5) | C11—C12 | 1.378 (6) |
O4—C16 | 1.221 (5) | C11—H11 | 0.9300 |
C1—C6 | 1.375 (6) | C12—C13 | 1.379 (5) |
C1—C2 | 1.390 (6) | C13—C14 | 1.385 (5) |
C2—C3 | 1.392 (6) | C13—H13 | 0.9300 |
C3—C4 | 1.382 (6) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—H15A | 0.9600 |
C4—C5 | 1.378 (6) | C15—H15B | 0.9600 |
C4—H4 | 0.9300 | C15—H15C | 0.9600 |
C5—C6 | 1.394 (5) | C16—C17 | 1.511 (6) |
C5—C8 | 1.499 (6) | C17—F1 | 1.323 (5) |
C6—H6 | 0.9300 | C17—F3 | 1.325 (5) |
C7—H7A | 0.9600 | C17—F2 | 1.341 (5) |
C7—H7B | 0.9600 | C17—F1' | 1.343 (10) |
C7—H7C | 0.9600 | C17—F3' | 1.345 (10) |
C8—H8A | 0.9600 | C17—F2' | 1.371 (9) |
| | | |
C1—I1—C9 | 94.37 (15) | C10—C11—H11 | 120.1 |
C2—O1—C7 | 119.5 (4) | O2—C12—C11 | 115.7 (4) |
C12—O2—C15 | 117.5 (4) | O2—C12—C13 | 123.3 (4) |
C6—C1—C2 | 122.4 (4) | C11—C12—C13 | 120.9 (4) |
C6—C1—I1 | 119.4 (3) | C12—C13—C14 | 119.1 (4) |
C2—C1—I1 | 118.1 (3) | C12—C13—H13 | 120.4 |
O1—C2—C1 | 117.2 (4) | C14—C13—H13 | 120.4 |
O1—C2—C3 | 125.8 (4) | C9—C14—C13 | 119.5 (4) |
C1—C2—C3 | 117.0 (5) | C9—C14—H14 | 120.2 |
C4—C3—C2 | 119.9 (5) | C13—C14—H14 | 120.2 |
C4—C3—H3 | 120.0 | O2—C15—H15A | 109.5 |
C2—C3—H3 | 120.0 | O2—C15—H15B | 109.5 |
C5—C4—C3 | 123.3 (4) | H15A—C15—H15B | 109.5 |
C5—C4—H4 | 118.3 | O2—C15—H15C | 109.5 |
C3—C4—H4 | 118.3 | H15A—C15—H15C | 109.5 |
C4—C5—C6 | 116.5 (4) | H15B—C15—H15C | 109.5 |
C4—C5—C8 | 122.0 (4) | O4—C16—O3 | 128.6 (5) |
C6—C5—C8 | 121.5 (4) | O4—C16—C17 | 115.0 (5) |
C1—C6—C5 | 120.8 (4) | O3—C16—C17 | 116.4 (4) |
C1—C6—H6 | 119.6 | F1—C17—F3 | 106.7 (5) |
C5—C6—H6 | 119.6 | F1—C17—F2 | 102.7 (4) |
O1—C7—H7A | 109.5 | F3—C17—F2 | 106.1 (4) |
O1—C7—H7B | 109.5 | F1—C17—F1' | 46.0 (17) |
H7A—C7—H7B | 109.5 | F3—C17—F1' | 122.9 (14) |
O1—C7—H7C | 109.5 | F2—C17—F1' | 57.2 (17) |
H7A—C7—H7C | 109.5 | F1—C17—F3' | 68.1 (14) |
H7B—C7—H7C | 109.5 | F3—C17—F3' | 42.0 (13) |
C5—C8—H8A | 109.5 | F2—C17—F3' | 129.9 (12) |
C5—C8—H8B | 109.5 | F1'—C17—F3' | 103.1 (19) |
H8A—C8—H8B | 109.5 | F1—C17—F2' | 144.1 (10) |
C5—C8—H8C | 109.5 | F3—C17—F2' | 61.9 (11) |
H8A—C8—H8C | 109.5 | F2—C17—F2' | 55.1 (12) |
H8B—C8—H8C | 109.5 | F1'—C17—F2' | 108.7 (19) |
C14—C9—C10 | 121.6 (4) | F3'—C17—F2' | 102.9 (16) |
C14—C9—I1 | 118.6 (3) | F1—C17—C16 | 111.0 (4) |
C10—C9—I1 | 119.8 (3) | F3—C17—C16 | 115.6 (4) |
C9—C10—C11 | 119.1 (4) | F2—C17—C16 | 113.7 (4) |
C9—C10—H10 | 120.5 | F1'—C17—C16 | 120.9 (14) |
C11—C10—H10 | 120.5 | F3'—C17—C16 | 115.5 (12) |
C12—C11—C10 | 119.7 (4) | F2'—C17—C16 | 104.3 (9) |
C12—C11—H11 | 120.1 | | |
| | | |
C9—I1—C1—C6 | −99.6 (3) | C15—O2—C12—C11 | 178.5 (4) |
C9—I1—C1—C2 | 77.9 (3) | C15—O2—C12—C13 | −2.4 (6) |
C7—O1—C2—C1 | 177.6 (4) | C10—C11—C12—O2 | 179.2 (4) |
C7—O1—C2—C3 | −2.8 (7) | C10—C11—C12—C13 | 0.1 (6) |
C6—C1—C2—O1 | 178.7 (4) | O2—C12—C13—C14 | −178.4 (3) |
I1—C1—C2—O1 | 1.3 (5) | C11—C12—C13—C14 | 0.6 (6) |
C6—C1—C2—C3 | −0.9 (6) | C10—C9—C14—C13 | −0.3 (6) |
I1—C1—C2—C3 | −178.3 (3) | I1—C9—C14—C13 | 179.1 (3) |
O1—C2—C3—C4 | −179.5 (4) | C12—C13—C14—C9 | −0.5 (6) |
C1—C2—C3—C4 | 0.1 (6) | O4—C16—C17—F1 | 99.7 (5) |
C2—C3—C4—C5 | 1.2 (7) | O3—C16—C17—F1 | −79.9 (6) |
C3—C4—C5—C6 | −1.6 (7) | O4—C16—C17—F3 | −22.1 (7) |
C3—C4—C5—C8 | 176.5 (5) | O3—C16—C17—F3 | 158.4 (5) |
C2—C1—C6—C5 | 0.5 (6) | O4—C16—C17—F2 | −145.2 (5) |
I1—C1—C6—C5 | 177.9 (3) | O3—C16—C17—F2 | 35.3 (6) |
C4—C5—C6—C1 | 0.7 (6) | O4—C16—C17—F1' | 150 (2) |
C8—C5—C6—C1 | −177.4 (4) | O3—C16—C17—F1' | −29 (2) |
C1—I1—C9—C14 | −113.5 (3) | O4—C16—C17—F3' | 24.8 (17) |
C1—I1—C9—C10 | 65.9 (3) | O3—C16—C17—F3' | −154.8 (16) |
C14—C9—C10—C11 | 1.0 (6) | O4—C16—C17—F2' | −87.4 (14) |
I1—C9—C10—C11 | −178.4 (3) | O3—C16—C17—F2' | 93.1 (14) |
C9—C10—C11—C12 | −0.9 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O3i | 0.93 | 2.48 | 3.297 (6) | 147 |
C13—H13···O4ii | 0.93 | 2.49 | 3.368 (6) | 158 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2. |
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