(5-Fluoro-4′-methyl­biphenyl-3-yl)(2,4,6-tri­methyl­phen­yl)iodo­nium tri­fluoro­methane­sulfonate

Shao, Y.; Liu, X.-L.; Wu, Z.-H.; Xia, Y.-A.

doi:10.1107/S160053681400720X

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o522

doi:10.1107/S160053681400720X

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(5-Fluoro-4′-methylbiphenyl-3-yl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate

Ying Shao,^a ^* Xiao-Long Liu,^a Zhu-Hong Wu ^a and Yong-An Xia ^a

^aKey Laboratory of Fine Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
^*Correspondence e-mail: shaoying810724@163.com

(Received 19 March 2014; accepted 1 April 2014; online 5 April 2014)

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

C₂₂H₂₁FI⁺·CF₃O₃S⁻
M_r = 580.37
Monoclinic, P 2₁ /n
a = 9.8987 (8) Å
b = 24.374 (2) Å
c = 10.0794 (9) Å
β = 105.820 (2)°
V = 2339.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.732, T_max = 0.772
13544 measured reflections
4341 independent reflections
3405 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.142
S = 1.14
4341 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −1.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: 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

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681400720X/hb7213sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

For background to diaryliodonium salts, see: Grushin (2000); Merritt & Olofsson (2009).

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: 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).

Figures top

	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.

(5-Fluoro-4'-methylbiphenyl-3-yl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate top

Crystal data top

C₂₂H₂₁FI⁺·CF₃O₃S⁻	F(000) = 1152
M_r = 580.37	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	4341 independent reflections
Radiation source: fine-focus sealed tube	3405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.732, T_max = 0.772	k = −27→29
13544 measured reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0805P)²] where P = (F_o² + 2F_c²)/3
4341 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −1.24 e Å⁻³

Crystal data top

C₂₂H₂₁FI⁺·CF₃O₃S⁻	V = 2339.7 (3) Å³
M_r = 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)°

Data collection top

Bruker APEXII CCD diffractometer	4341 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3405 reflections with I > 2σ(I)
T_min = 0.732, T_max = 0.772	R_int = 0.057
13544 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.14	Δρ_max = 0.75 e Å⁻³
4341 reflections	Δρ_min = −1.24 e Å⁻³
293 parameters

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	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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

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Volume 70| Part 5| May 2014| Page o522

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(5-Fluoro-4′-methyl­bi­phenyl-3-yl)(2,4,6-tri­methyl­phen­yl)iodo­nium tri­fluoro­methane­sulfonate

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Experimental

Crystal data

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organic compounds

(5-Fluoro-4′-methylbiphenyl-3-yl)(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate