(2-Meth­oxy-5-methyl­phen­yl)(4-methoxy­phen­yl)iodo­nium trifluoro­acetate

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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.26 × 0.24 × 0.20 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0273P)^2 + 0.6825P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3^i	0.93	2.48	3.297 (6)	147
C13—H13···O4^ii	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.