4,4′-Bis(4-fluoro­phenyl­sulfon­yl)­oxy­dibenzene

Lister, A.R.; Moratti, S.C.; Simpson, J.

doi:10.1107/S1600536807047204

4,4′-Bis(4-fluorophenylsulfonyl)oxydibenzene

A. R. Lister, S. C. Moratti and J. Simpson

In the title compound, C₂₄H₁₆F₂O₅S₂, the benzene rings of the central oxydibenzene unit are inclined at an angle of 83.49 (8)° to one another. Each of these benzene rings carries a p-substituted 4-fluorosulfonylbenzene group with dihedral angles of 77.27 (8) and 62.06 (11)° between the respective 4-fluorosulfonylbenzene and oxydibenzene rings. In the crystal structure, a complex network of C—H

F and C—H

O hydrogen bonds and a C—H

π interaction link the molecules into columns along the bc diagonal.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047204/gw2026sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047204/gw2026Isup2.hkl Contains datablock I

CCDC reference: 667293

checkCIF report

Key indicators

Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.004 Å
R factor = 0.039
wR factor = 0.096
Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found





Alert level A
THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5366
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6].....      22.42 Deg.
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      22.42 Deg.

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5366
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.1812
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.18
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A   ..  F1      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23A   ..  F1      ..       2.65 Ang.

   3 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Polysulphones are an important class of high temperature thermoplastics. The properties of these polymers are dependent on the flexibility of the chain (for the glass transition temperature) and any crystallinity (for the melting point transition) (Carlier et al., 1992). An important method of obtaining and refining the X-ray structure for any polymer is by using the X-ray structure of related oligomers (Colquhoun et al., 2003), thus any information on the packing motifs of extended oligomers is very useful. During the preparation of a polysulfone dendrimer, the title compound was obtained as a minor impurity. It probably arose from the nucleophilic attack of trace amounts of water on 4-fluorophenylsulfone under the reaction conditions (160 °C in DMSO).

The benzene rings of the central oxydibenzene unit are inclined at an angle of 83.49 (8)° to one another. Each of these benzene rings carries a p-substituted 4-fluorosulfonylbenzene system with dihedral angles of 77.27 (8)° and 62.06 (11)° between the C1···C6 & C7···C9 and between the C13···C18 & C19···C24 rings respectively.

In the crystal structure, a complex network of C—H···F, C—H···O hydrogen bonds and a C11—H11A···Cg1^vii π-interaction link the molecules into columns along the bc diagonal (Cg1 is the centroid of the C1···C6 ring; iv = x, -y + 1/2, z + 1/2), Table 1.

Related literature top

For details of structure–property relationships of crystalline polysulfones, see Carlier et al. (1992), and for information on structure determinations of polymers from powder data, see Colquhoun et al. (2003). For related structures, see for example Colquhoun et al. (2005, 2002) and Holman et al. (2001).

Experimental top

To a solution of a generation 1 polysulfone dendrimer (0.50 g, 0.6 mmol) and 4-fluorophenyl sulphone (3.08 g, 12.1 mmol) in anhydrous DMSO (40 ml) was added Na₂CO₃ (0.26 g, 2.4 mmol). The mixture was heated under nitrogen at 160 °C for 5 h, water (60 ml) was added and the mixture extracted with ethyl acetate (3 x 40 ml). The combined extracts were then dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography using 80:20 hexane:ethyl acetate yielded 0.02 g (1%) of a white solid, the title compound (I). Rf (hexane:ethyl acetate 1:1) 0.80; m.p 140–142 °C; IR (KBr) 2900, 1750, 1590, 1505, 1490, 1410, 1300, 1250, 1150, 1010 cm^-1; 1H NMR (400 MHz) δ (CDCl₃) 7.96–7.88 (m, 4H, H-3, H-6), 7.18 (t, 2H, H-2, ³JHH = 8.5 Hz), 7.08 (d, 2H, H-7, ³JHH = 9.0 Hz). Colourles needles were obtained by layering a solution in ethyl acetate with hexane.

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick 1997), enCIFer (Allen et al., 2004) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I) showing the atom numbering with ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal packing for (I) with hydrogen bonds drawn as dashed lines.

4,4'-Bis(4-fluorophenylsulfonyl)oxydibenzene top

Crystal data top

C₂₄H₁₆F₂O₅S₂	F(000) = 1000
M_r = 486.49	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6093 reflections
a = 14.0437 (6) Å	θ = 1.0–22.5°
b = 16.0590 (6) Å	µ = 0.30 mm⁻¹
c = 9.6644 (3) Å	T = 180 K
β = 102.223 (1)°	Needle, colourless
V = 2130.18 (14) Å³	0.23 × 0.07 × 0.05 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2736 independent reflections
Radiation source: fine-focus sealed tube	2084 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Thin–slice ω and φ scans	θ_max = 22.4°, θ_min = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −15→15
T_min = 0.954, T_max = 0.996	k = −17→16
10006 measured reflections	l = −10→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0393P)² + 0.9105P] where P = (F_o² + 2F_c²)/3
2736 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₄H₁₆F₂O₅S₂	V = 2130.18 (14) Å³
M_r = 486.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.0437 (6) Å	µ = 0.30 mm⁻¹
b = 16.0590 (6) Å	T = 180 K
c = 9.6644 (3) Å	0.23 × 0.07 × 0.05 mm
β = 102.223 (1)°

Data collection top

Nonius KappaCCD diffractometer	2736 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2084 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.996	R_int = 0.055
10006 measured reflections	θ_max = 22.4°

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.06	Δρ_max = 0.28 e Å⁻³
2736 reflections	Δρ_min = −0.34 e Å⁻³
298 parameters

Special details top

Experimental. Poorly diffracting crystals (ThetaMax=22.5 degrees).

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
S1	−0.13021 (6)	0.01325 (5)	−0.26488 (8)	0.0311 (3)
S2	0.48394 (6)	0.32919 (6)	0.15358 (8)	0.0318 (3)
O1	−0.21631 (15)	−0.01428 (14)	−0.2205 (2)	0.0387 (6)
O2	−0.06039 (15)	−0.04715 (13)	−0.2910 (2)	0.0364 (6)
O3	0.06855 (15)	0.26534 (14)	0.1351 (2)	0.0386 (6)
O4	0.48671 (16)	0.35984 (15)	0.0145 (2)	0.0428 (6)
O5	0.53284 (15)	0.25302 (14)	0.2019 (2)	0.0439 (6)
F1	−0.25344 (14)	0.20090 (14)	−0.79030 (19)	0.0568 (6)
F2	0.65833 (17)	0.59150 (16)	0.5413 (2)	0.0847 (8)
C1	−0.2260 (2)	0.1570 (2)	−0.6682 (3)	0.0370 (9)
C2	−0.1336 (2)	0.1256 (2)	−0.6377 (3)	0.0406 (9)
H2A	−0.0907	0.1334	−0.7005	0.049*
C3	−0.1043 (2)	0.0820 (2)	−0.5124 (3)	0.0341 (8)
H3A	−0.0404	0.0596	−0.4879	0.041*
C4	−0.1681 (2)	0.0710 (2)	−0.4232 (3)	0.0285 (8)
C5	−0.2618 (2)	0.1028 (2)	−0.4580 (3)	0.0347 (9)
H5A	−0.3056	0.0944	−0.3967	0.042*
C6	−0.2913 (2)	0.1470 (2)	−0.5834 (3)	0.0394 (9)
H6A	−0.3551	0.1696	−0.6092	0.047*
C7	−0.0686 (2)	0.08542 (19)	−0.1416 (3)	0.0266 (8)
C8	0.0317 (2)	0.0945 (2)	−0.1237 (3)	0.0309 (8)
H8A	0.0670	0.0599	−0.1747	0.037*
C9	0.0800 (2)	0.1539 (2)	−0.0319 (3)	0.0316 (8)
H9A	0.1484	0.1607	−0.0197	0.038*
C10	0.0276 (2)	0.2034 (2)	0.0422 (3)	0.0275 (8)
C11	−0.0724 (2)	0.1941 (2)	0.0261 (3)	0.0306 (8)
H11A	−0.1075	0.2284	0.0780	0.037*
C12	−0.1202 (2)	0.1350 (2)	−0.0651 (3)	0.0314 (8)
H12A	−0.1886	0.1279	−0.0761	0.038*
C13	0.1672 (2)	0.2833 (2)	0.1457 (3)	0.0308 (8)
C14	0.1924 (2)	0.3476 (2)	0.0666 (3)	0.0367 (9)
H14A	0.1435	0.3803	0.0081	0.044*
C15	0.2898 (2)	0.3641 (2)	0.0732 (3)	0.0372 (9)
H15A	0.3083	0.4079	0.0182	0.045*
C16	0.3603 (2)	0.31666 (19)	0.1601 (3)	0.0266 (8)
C17	0.3337 (2)	0.2549 (2)	0.2444 (3)	0.0336 (8)
H17A	0.3823	0.2246	0.3079	0.040*
C18	0.2363 (2)	0.2377 (2)	0.2360 (3)	0.0337 (8)
H18A	0.2173	0.1947	0.2921	0.040*
C19	0.5321 (2)	0.4080 (2)	0.2748 (3)	0.0285 (8)
C20	0.5202 (2)	0.4902 (2)	0.2328 (3)	0.0392 (9)
H20A	0.4836	0.5037	0.1412	0.047*
C21	0.5614 (3)	0.5524 (2)	0.3236 (4)	0.0483 (10)
H21A	0.5527	0.6093	0.2969	0.058*
C22	0.6147 (3)	0.5304 (3)	0.4519 (4)	0.0495 (11)
C23	0.6269 (2)	0.4498 (3)	0.4990 (4)	0.0481 (10)
H23A	0.6635	0.4372	0.5910	0.058*
C24	0.5846 (2)	0.3878 (2)	0.4090 (3)	0.0387 (9)
H24A	0.5912	0.3313	0.4384	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0289 (5)	0.0299 (5)	0.0332 (5)	−0.0017 (4)	0.0037 (4)	0.0001 (4)
S2	0.0277 (5)	0.0332 (6)	0.0339 (5)	−0.0006 (4)	0.0049 (4)	−0.0033 (4)
O1	0.0299 (13)	0.0412 (15)	0.0465 (13)	−0.0085 (11)	0.0112 (11)	0.0047 (11)
O2	0.0341 (13)	0.0312 (14)	0.0415 (13)	0.0064 (11)	0.0029 (10)	−0.0002 (11)
O3	0.0299 (14)	0.0460 (16)	0.0406 (13)	−0.0055 (12)	0.0090 (10)	−0.0136 (11)
O4	0.0412 (14)	0.0584 (17)	0.0304 (12)	−0.0075 (13)	0.0112 (10)	−0.0024 (11)
O5	0.0329 (13)	0.0313 (15)	0.0652 (15)	0.0065 (12)	0.0048 (11)	−0.0052 (12)
F1	0.0491 (13)	0.0766 (17)	0.0446 (12)	0.0151 (12)	0.0096 (10)	0.0244 (11)
F2	0.0787 (17)	0.090 (2)	0.0900 (17)	−0.0365 (15)	0.0284 (14)	−0.0590 (16)
C1	0.038 (2)	0.041 (2)	0.0298 (19)	0.0054 (18)	0.0020 (17)	0.0033 (16)
C2	0.038 (2)	0.048 (2)	0.039 (2)	0.0067 (19)	0.0164 (16)	0.0064 (18)
C3	0.0279 (19)	0.034 (2)	0.0409 (19)	0.0040 (16)	0.0087 (16)	0.0009 (16)
C4	0.0277 (19)	0.028 (2)	0.0284 (17)	−0.0005 (16)	0.0024 (15)	−0.0021 (14)
C5	0.0267 (19)	0.042 (2)	0.0367 (19)	−0.0009 (17)	0.0092 (15)	−0.0020 (17)
C6	0.0261 (19)	0.050 (2)	0.040 (2)	0.0070 (18)	0.0027 (16)	0.0015 (18)
C7	0.0252 (19)	0.027 (2)	0.0269 (16)	0.0006 (15)	0.0033 (14)	0.0038 (14)
C8	0.0274 (19)	0.038 (2)	0.0286 (17)	0.0045 (16)	0.0086 (14)	−0.0002 (16)
C9	0.0193 (17)	0.045 (2)	0.0304 (17)	−0.0031 (17)	0.0051 (14)	−0.0017 (17)
C10	0.028 (2)	0.030 (2)	0.0238 (16)	−0.0020 (16)	0.0036 (14)	−0.0003 (15)
C11	0.0254 (19)	0.038 (2)	0.0302 (17)	0.0028 (16)	0.0088 (14)	−0.0003 (16)
C12	0.0228 (18)	0.037 (2)	0.0338 (18)	−0.0001 (17)	0.0040 (15)	0.0034 (16)
C13	0.0248 (19)	0.041 (2)	0.0265 (17)	−0.0019 (17)	0.0059 (15)	−0.0082 (16)
C14	0.030 (2)	0.042 (2)	0.0357 (18)	0.0065 (17)	0.0017 (15)	0.0091 (17)
C15	0.033 (2)	0.038 (2)	0.041 (2)	−0.0004 (18)	0.0082 (16)	0.0093 (17)
C16	0.0307 (19)	0.023 (2)	0.0245 (16)	0.0006 (15)	0.0014 (14)	−0.0026 (15)
C17	0.038 (2)	0.030 (2)	0.0303 (17)	0.0003 (17)	0.0019 (15)	0.0025 (16)
C18	0.037 (2)	0.031 (2)	0.0350 (19)	−0.0043 (17)	0.0109 (16)	0.0034 (16)
C19	0.0231 (17)	0.030 (2)	0.0334 (18)	−0.0038 (16)	0.0092 (14)	−0.0007 (16)
C20	0.043 (2)	0.037 (2)	0.0411 (19)	−0.0020 (19)	0.0153 (17)	0.0013 (18)
C21	0.053 (2)	0.034 (2)	0.064 (3)	−0.010 (2)	0.026 (2)	−0.005 (2)
C22	0.038 (2)	0.056 (3)	0.059 (3)	−0.016 (2)	0.020 (2)	−0.033 (2)
C23	0.036 (2)	0.071 (3)	0.035 (2)	0.000 (2)	0.0025 (16)	−0.011 (2)
C24	0.035 (2)	0.046 (2)	0.0335 (19)	0.0066 (18)	0.0026 (16)	0.0006 (17)

Geometric parameters (Å, º) top

S1—O1	1.436 (2)	C9—C10	1.382 (4)
S1—O2	1.439 (2)	C9—H9A	0.9500
S1—C7	1.754 (3)	C10—C11	1.387 (4)
S1—C4	1.772 (3)	C11—C12	1.370 (4)
S2—O5	1.432 (2)	C11—H11A	0.9500
S2—O4	1.440 (2)	C12—H12A	0.9500
S2—C19	1.759 (3)	C13—C18	1.372 (4)
S2—C16	1.762 (3)	C13—C14	1.376 (5)
O3—C10	1.381 (4)	C14—C15	1.381 (4)
O3—C13	1.397 (4)	C14—H14A	0.9500
F1—C1	1.359 (4)	C15—C16	1.384 (4)
F2—C22	1.363 (4)	C15—H15A	0.9500
C1—C6	1.362 (4)	C16—C17	1.384 (4)
C1—C2	1.365 (4)	C17—C18	1.382 (4)
C2—C3	1.383 (4)	C17—H17A	0.9500
C2—H2A	0.9500	C18—H18A	0.9500
C3—C4	1.380 (4)	C19—C20	1.381 (5)
C3—H3A	0.9500	C19—C24	1.387 (4)
C4—C5	1.384 (4)	C20—C21	1.374 (5)
C5—C6	1.390 (4)	C20—H20A	0.9500
C5—H5A	0.9500	C21—C22	1.353 (5)
C6—H6A	0.9500	C21—H21A	0.9500
C7—C8	1.390 (4)	C22—C23	1.372 (5)
C7—C12	1.391 (4)	C23—C24	1.371 (5)
C8—C9	1.379 (4)	C23—H23A	0.9500
C8—H8A	0.9500	C24—H24A	0.9500

O1—S1—O2	119.54 (14)	C12—C11—C10	119.6 (3)
O1—S1—C7	109.04 (14)	C12—C11—H11A	120.2
O2—S1—C7	107.93 (13)	C10—C11—H11A	120.2
O1—S1—C4	107.54 (14)	C11—C12—C7	119.9 (3)
O2—S1—C4	107.03 (14)	C11—C12—H12A	120.1
C7—S1—C4	104.80 (14)	C7—C12—H12A	120.1
O5—S2—O4	119.39 (15)	C18—C13—C14	121.6 (3)
O5—S2—C19	107.87 (14)	C18—C13—O3	119.6 (3)
O4—S2—C19	107.08 (15)	C14—C13—O3	118.8 (3)
O5—S2—C16	107.39 (14)	C13—C14—C15	119.2 (3)
O4—S2—C16	107.11 (13)	C13—C14—H14A	120.4
C19—S2—C16	107.50 (14)	C15—C14—H14A	120.4
C10—O3—C13	117.9 (2)	C14—C15—C16	119.7 (3)
F1—C1—C6	118.7 (3)	C14—C15—H15A	120.1
F1—C1—C2	117.5 (3)	C16—C15—H15A	120.1
C6—C1—C2	123.8 (3)	C17—C16—C15	120.3 (3)
C1—C2—C3	118.0 (3)	C17—C16—S2	119.6 (2)
C1—C2—H2A	121.0	C15—C16—S2	119.9 (2)
C3—C2—H2A	121.0	C18—C17—C16	119.8 (3)
C4—C3—C2	120.0 (3)	C18—C17—H17A	120.1
C4—C3—H3A	120.0	C16—C17—H17A	120.1
C2—C3—H3A	120.0	C13—C18—C17	119.3 (3)
C3—C4—C5	120.7 (3)	C13—C18—H18A	120.4
C3—C4—S1	119.4 (2)	C17—C18—H18A	120.4
C5—C4—S1	119.9 (2)	C20—C19—C24	120.3 (3)
C4—C5—C6	119.5 (3)	C20—C19—S2	119.1 (2)
C4—C5—H5A	120.2	C24—C19—S2	120.5 (3)
C6—C5—H5A	120.2	C21—C20—C19	120.0 (3)
C1—C6—C5	118.1 (3)	C21—C20—H20A	120.0
C1—C6—H6A	121.0	C19—C20—H20A	120.0
C5—C6—H6A	121.0	C22—C21—C20	118.1 (4)
C8—C7—C12	120.2 (3)	C22—C21—H21A	120.9
C8—C7—S1	119.7 (2)	C20—C21—H21A	120.9
C12—C7—S1	120.1 (2)	C21—C22—F2	118.7 (4)
C9—C8—C7	120.0 (3)	C21—C22—C23	123.8 (3)
C9—C8—H8A	120.0	F2—C22—C23	117.5 (4)
C7—C8—H8A	120.0	C24—C23—C22	117.9 (3)
C8—C9—C10	119.2 (3)	C24—C23—H23A	121.0
C8—C9—H9A	120.4	C22—C23—H23A	121.0
C10—C9—H9A	120.4	C23—C24—C19	119.8 (3)
O3—C10—C9	123.8 (3)	C23—C24—H24A	120.1
O3—C10—C11	115.0 (3)	C19—C24—H24A	120.1
C9—C10—C11	121.2 (3)

F1—C1—C2—C3	178.9 (3)	C10—O3—C13—C18	−85.5 (3)
C6—C1—C2—C3	−0.9 (5)	C10—O3—C13—C14	95.6 (4)
C1—C2—C3—C4	0.3 (5)	C18—C13—C14—C15	3.1 (5)
C2—C3—C4—C5	0.5 (5)	O3—C13—C14—C15	−178.0 (3)
C2—C3—C4—S1	178.7 (3)	C13—C14—C15—C16	−0.8 (5)
O1—S1—C4—C3	−159.3 (3)	C14—C15—C16—C17	−2.5 (5)
O2—S1—C4—C3	−29.7 (3)	C14—C15—C16—S2	172.6 (2)
C7—S1—C4—C3	84.8 (3)	O5—S2—C16—C17	19.8 (3)
O1—S1—C4—C5	18.9 (3)	O4—S2—C16—C17	149.1 (2)
O2—S1—C4—C5	148.6 (3)	C19—S2—C16—C17	−96.1 (3)
C7—S1—C4—C5	−97.0 (3)	O5—S2—C16—C15	−155.3 (2)
C3—C4—C5—C6	−0.8 (5)	O4—S2—C16—C15	−26.0 (3)
S1—C4—C5—C6	−179.1 (2)	C19—S2—C16—C15	88.8 (3)
F1—C1—C6—C5	−179.2 (3)	C15—C16—C17—C18	3.5 (5)
C2—C1—C6—C5	0.5 (5)	S2—C16—C17—C18	−171.6 (2)
C4—C5—C6—C1	0.4 (5)	C14—C13—C18—C17	−2.1 (5)
O1—S1—C7—C8	152.6 (2)	O3—C13—C18—C17	179.0 (3)
O2—S1—C7—C8	21.3 (3)	C16—C17—C18—C13	−1.3 (5)
C4—S1—C7—C8	−92.5 (3)	O5—S2—C19—C20	160.3 (2)
O1—S1—C7—C12	−29.3 (3)	O4—S2—C19—C20	30.7 (3)
O2—S1—C7—C12	−160.6 (2)	C16—S2—C19—C20	−84.1 (3)
C4—S1—C7—C12	85.6 (3)	O5—S2—C19—C24	−17.1 (3)
C12—C7—C8—C9	−1.2 (4)	O4—S2—C19—C24	−146.8 (2)
S1—C7—C8—C9	176.9 (2)	C16—S2—C19—C24	98.4 (3)
C7—C8—C9—C10	0.5 (5)	C24—C19—C20—C21	0.7 (5)
C13—O3—C10—C9	5.3 (4)	S2—C19—C20—C21	−176.8 (3)
C13—O3—C10—C11	−174.0 (3)	C19—C20—C21—C22	1.3 (5)
C8—C9—C10—O3	−179.0 (3)	C20—C21—C22—F2	178.1 (3)
C8—C9—C10—C11	0.2 (5)	C20—C21—C22—C23	−2.6 (6)
O3—C10—C11—C12	179.1 (3)	C21—C22—C23—C24	1.7 (6)
C9—C10—C11—C12	−0.2 (5)	F2—C22—C23—C24	−179.0 (3)
C10—C11—C12—C7	−0.6 (5)	C22—C23—C24—C19	0.4 (5)
C8—C7—C12—C11	1.3 (4)	C20—C19—C24—C23	−1.6 (5)
S1—C7—C12—C11	−176.9 (2)	S2—C19—C24—C23	175.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	0.95	2.55	3.206 (4)	126
C6—H6A···O5ⁱⁱ	0.95	2.53	3.337 (4)	143
C14—H14A···O2ⁱⁱⁱ	0.95	2.47	3.361 (4)	157
C17—H17A···O4^iv	0.95	2.60	3.529 (4)	168
C11—H11A···F1^v	0.95	2.67	3.396 (4)	134
C23—H23A···F1^vi	0.95	2.65	3.373 (5)	133
C11—H11A···Cg1^iv	0.95	2.97	3.541 (3)	120

Symmetry codes: (i) −x, −y, −z−1; (ii) x−1, y, z−1; (iii) −x, y+1/2, −z−1/2; (iv) x, −y+1/2, z+1/2; (v) x, y, z+1; (vi) x+1, −y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆F₂O₅S₂
M_r	486.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	180
a, b, c (Å)	14.0437 (6), 16.0590 (6), 9.6644 (3)
β (°)	102.223 (1)
V (Å³)	2130.18 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.23 × 0.07 × 0.05

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.954, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	10006, 2736, 2084
R_int	0.055
θ_max (°)	22.4
(sin θ/λ)_max (Å⁻¹)	0.537

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.096, 1.06
No. of reflections	2736
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.34

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick 1997), enCIFer (Allen et al., 2004) and PLATON (Spek, 2003).