3,4',5-Trichloro-biphenyl-4-yl 2,2,2-trichloro-ethyl sulfate.

Crystals of the title compound, C14H8Cl6O4S, are twinned by inversion, with unequal components [0.85 (3):0.15 (3)]. The asymmetric unit contains two independent mol-ecules that are related by a pseudo-inversion center. The Car-O [1.393 (9) and 1.397 (9) Å] and ester S-O bond lengths [1.600 (5) and 1.590 (5) Å] of both mol-ecules are comparable to the structurally related 2,3,5,5-trichloro-biphenyl-4-yl 2,2,2-trichloro-ethyl sulfate. The dihedral angles between the benzene rings in the two mol-ecules are 37.8 (2) and 35.0 (2)°.

Related literature

For related structures of biphenyl-4-yl ester 2,2,2-trichloro-ethyl esters of sulfuric acid, see: Li et al. (2008 ▶, 2010a ▶,b ▶,c ▶). For a review of structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005 ▶); Denehy et al. (2006 ▶). For additional background to sulfate metabolites of polychlorinated bi­phenyls, see: Liu et al. (2006 ▶, 2009 ▶); Wang et al. (2006 ▶); Dhakal et al. (2012 ▶); Zhai et al. (2013 ▶).

Experimental

Crystal data

C14H8Cl6O4S

M = 484.96

Orthorhombic,

a = 13.993 (3) Å

b = 9.1890 (18) Å

c = 28.778 (6) Å

V = 3700.3 (13) Å3

Z = 8

Cu Kα radiation

μ = 9.71 mm−1

T = 90 K

0.17 × 0.09 × 0.02 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.504, T max = 0.830

45894 measured reflections

6651 independent reflections

6238 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.161

S = 1.15

6651 reflections

302 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −0.85 e Å−3

Absolute structure: Flack (1983 ▶), 3176 Friedel pairs

Flack parameter: 0.15 (3)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007976/yk2088sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007976/yk2088Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007976/yk2088Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H8Cl6O4S	F(000) = 1936
Mr = 484.96	Dx = 1.741 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 9992 reflections
a = 13.993 (3) Å	θ = 3.1–68.3°
b = 9.1890 (18) Å	µ = 9.71 mm−1
c = 28.778 (6) Å	T = 90 K
V = 3700.3 (13) Å3	Flake, colourless
Z = 8	0.17 × 0.09 × 0.02 mm

Bruker X8 Proteum diffractometer	6651 independent reflections
Radiation source: fine-focus rotating anode	6238 reflections with I > 2σ(I)
Graded multilayer optics monochromator	Rint = 0.062
Detector resolution: 5.6 pixels mm-1	θmax = 68.4°, θmin = 3.1°
φ and ω scans	h = −14→16
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −10→11
Tmin = 0.504, Tmax = 0.830	l = −34→34
45894 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0514P)2 + 21.3733P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
6651 reflections	Δρmax = 0.96 e Å−3
302 parameters	Δρmin = −0.85 e Å−3
1 restraint	Absolute structure: Flack (1983), 3176 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.15 (3)

Experimental. The crystal was twinned by inversion, but with unequal sized pieces of each component. The refined Flack parameter indicates major:minor fractions of 0.85 (3):0.15 (3).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against all reflections. The weighted R-value wR and goodness of fit S are based on F2. Conventional R-values R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-values based on F2 are statistically about twice as large as those based on F, and R-values based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1A	0.77740 (12)	0.4047 (2)	0.35290 (7)	0.0283 (2)
O1A	0.8439 (4)	0.2785 (5)	0.33235 (19)	0.0273 (7)
O2A	0.8158 (4)	0.4167 (6)	0.40377 (19)	0.0313 (7)
O3A	0.7985 (4)	0.5393 (6)	0.3314 (2)	0.0302 (7)
O4A	0.6838 (4)	0.3483 (6)	0.3531 (2)	0.0349 (7)
Cl1A	1.03327 (13)	0.3420 (2)	0.37524 (7)	0.0380 (3)
Cl2A	0.78298 (12)	0.2737 (2)	0.23480 (7)	0.0318 (2)
Cl3A	1.37897 (13)	0.5084 (2)	0.10448 (8)	0.0378 (3)
Cl4A	0.8960 (2)	0.4431 (3)	0.50012 (9)	0.0563 (4)
Cl5A	0.69326 (19)	0.4810 (2)	0.48583 (9)	0.0487 (4)
Cl6A	0.76595 (19)	0.2066 (2)	0.52014 (8)	0.0489 (4)
C1A	1.0641 (5)	0.3630 (7)	0.2372 (3)	0.0240 (9)
C2A	1.0822 (5)	0.3612 (8)	0.2847 (3)	0.0273 (9)
H2A	1.1456	0.3760	0.2956	0.033*
C3A	1.0090 (5)	0.3381 (8)	0.3166 (3)	0.0276 (9)
C4A	0.9162 (5)	0.3143 (8)	0.3011 (3)	0.0252 (9)
C5A	0.8987 (5)	0.3119 (7)	0.2542 (3)	0.0259 (9)
C6A	0.9704 (5)	0.3381 (8)	0.2223 (3)	0.0273 (9)
H6A	0.9560	0.3393	0.1900	0.033*
C7A	0.7997 (6)	0.2919 (9)	0.4344 (3)	0.0326 (10)
H7A1	0.8546	0.2241	0.4332	0.039*
H7A2	0.7412	0.2386	0.4251	0.039*
C8A	0.7887 (7)	0.3548 (10)	0.4822 (3)	0.0431 (12)
C1'A	1.1400 (5)	0.3932 (8)	0.2034 (3)	0.0284 (9)
C2'A	1.1233 (5)	0.4783 (9)	0.1639 (3)	0.0314 (11)
H2'A	1.0607	0.5138	0.1581	0.038*
C3'A	1.1959 (5)	0.5118 (9)	0.1333 (3)	0.0307 (10)
H3'A	1.1833	0.5691	0.1065	0.037*
C4'A	1.2877 (5)	0.4609 (9)	0.1420 (3)	0.0284 (10)
C5'A	1.3053 (5)	0.3752 (8)	0.1800 (3)	0.0293 (10)
H5'A	1.3677	0.3379	0.1850	0.035*
C6'A	1.2329 (5)	0.3424 (8)	0.2113 (3)	0.0285 (9)
H6'A	1.2464	0.2854	0.2380	0.034*
S1B	0.48992 (12)	0.0952 (2)	0.44025 (7)	0.0283 (2)
O1B	0.4243 (3)	0.2207 (5)	0.46086 (19)	0.0273 (7)
O2B	0.4512 (4)	0.0835 (6)	0.38944 (19)	0.0313 (7)
O3B	0.4667 (4)	−0.0367 (6)	0.4615 (2)	0.0302 (7)
O4B	0.5834 (4)	0.1524 (6)	0.4402 (2)	0.0349 (7)
Cl1B	0.23508 (13)	0.1574 (2)	0.41731 (7)	0.0380 (3)
Cl2B	0.48229 (12)	0.2267 (2)	0.55864 (7)	0.0318 (2)
Cl3B	−0.11866 (13)	0.0187 (2)	0.68821 (8)	0.0378 (3)
Cl4B	0.3715 (2)	0.0537 (3)	0.29351 (9)	0.0563 (4)
Cl5B	0.50048 (19)	0.2929 (2)	0.27257 (8)	0.0487 (4)
Cl6B	0.57633 (19)	0.0222 (3)	0.30941 (8)	0.0489 (4)
C1B	0.2034 (5)	0.1376 (8)	0.5547 (3)	0.0240 (9)
C2B	0.1855 (5)	0.1373 (8)	0.5077 (3)	0.0273 (9)
H2B	0.1222	0.1221	0.4967	0.033*
C3B	0.2590 (5)	0.1590 (8)	0.4759 (3)	0.0276 (9)
C4B	0.3515 (5)	0.1866 (8)	0.4923 (3)	0.0252 (9)
C5B	0.3684 (5)	0.1883 (8)	0.5392 (3)	0.0259 (9)
C6B	0.2963 (5)	0.1672 (8)	0.5714 (3)	0.0273 (9)
H6B	0.3089	0.1725	0.6038	0.033*
C7B	0.4686 (6)	0.2041 (9)	0.3589 (3)	0.0326 (10)
H7B1	0.5276	0.2556	0.3684	0.039*
H7B2	0.4146	0.2736	0.3604	0.039*
C8B	0.4791 (7)	0.1461 (10)	0.3102 (3)	0.0431 (12)
C1'B	0.1230 (5)	0.1095 (8)	0.5886 (3)	0.0284 (9)
C2'B	0.1395 (5)	0.0364 (9)	0.6294 (3)	0.0314 (11)
H2'B	0.2024	0.0042	0.6364	0.038*
C3'B	0.0659 (5)	0.0087 (8)	0.6607 (3)	0.0307 (10)
H3'B	0.0784	−0.0421	0.6888	0.037*
C4'B	−0.0243 (5)	0.0551 (9)	0.6506 (3)	0.0284 (10)
C5'B	−0.0442 (5)	0.1307 (8)	0.6098 (3)	0.0293 (10)
H5'B	−0.1072	0.1629	0.6031	0.035*
C6'B	0.0308 (5)	0.1580 (8)	0.5789 (3)	0.0285 (9)
H6'B	0.0188	0.2102	0.5510	0.034*

	U11	U22	U33	U12	U13	U23
S1A	0.0183 (5)	0.0276 (5)	0.0392 (6)	0.0017 (4)	0.0002 (4)	0.0039 (4)
O1A	0.0202 (14)	0.0205 (15)	0.0411 (17)	−0.0046 (12)	0.0037 (13)	0.0031 (12)
O2A	0.0285 (16)	0.0267 (16)	0.0386 (17)	−0.0036 (13)	0.0023 (13)	0.0059 (13)
O3A	0.0248 (17)	0.0217 (16)	0.0442 (18)	0.0022 (12)	0.0006 (13)	0.0063 (13)
O4A	0.0187 (15)	0.0370 (18)	0.0491 (19)	−0.0033 (13)	−0.0001 (14)	0.0041 (15)
Cl1A	0.0219 (5)	0.0543 (7)	0.0379 (6)	−0.0016 (5)	−0.0044 (5)	0.0037 (5)
Cl2A	0.0167 (5)	0.0340 (6)	0.0447 (6)	−0.0060 (4)	−0.0047 (4)	0.0021 (5)
Cl3A	0.0279 (6)	0.0455 (7)	0.0399 (6)	−0.0032 (5)	0.0037 (5)	0.0000 (6)
Cl4A	0.0802 (11)	0.0341 (6)	0.0545 (8)	−0.0139 (7)	−0.0252 (7)	0.0035 (5)
Cl5A	0.0709 (11)	0.0286 (7)	0.0465 (9)	0.0093 (7)	0.0109 (8)	0.0067 (7)
Cl6A	0.0715 (11)	0.0299 (8)	0.0454 (9)	0.0031 (7)	0.0054 (8)	0.0030 (7)
C1A	0.018 (2)	0.0134 (18)	0.040 (2)	0.0007 (16)	0.0015 (18)	0.0006 (17)
C2A	0.0137 (19)	0.023 (2)	0.045 (3)	−0.0001 (16)	−0.0014 (17)	0.0013 (19)
C3A	0.019 (2)	0.020 (2)	0.044 (2)	0.0014 (17)	−0.0017 (18)	0.0002 (18)
C4A	0.0122 (18)	0.0156 (19)	0.048 (3)	−0.0009 (15)	−0.0002 (18)	0.0014 (17)
C5A	0.017 (2)	0.0120 (18)	0.048 (3)	0.0000 (16)	0.0010 (18)	0.0004 (17)
C6A	0.020 (2)	0.022 (2)	0.040 (2)	−0.0008 (17)	−0.0039 (18)	−0.0016 (18)
C7A	0.033 (2)	0.027 (2)	0.038 (2)	0.001 (2)	−0.002 (2)	0.0039 (19)
C8A	0.060 (3)	0.028 (2)	0.041 (3)	−0.002 (2)	−0.007 (3)	0.000 (2)
C1'A	0.017 (2)	0.024 (2)	0.044 (2)	0.0023 (17)	−0.0018 (18)	−0.0069 (19)
C2'A	0.017 (2)	0.034 (3)	0.043 (2)	0.0000 (19)	−0.0038 (19)	0.000 (2)
C3'A	0.025 (2)	0.030 (2)	0.037 (2)	0.002 (2)	−0.005 (2)	0.000 (2)
C4'A	0.019 (2)	0.026 (2)	0.040 (2)	−0.0023 (18)	0.0028 (18)	−0.0037 (19)
C5'A	0.019 (2)	0.026 (2)	0.043 (3)	0.0008 (18)	−0.0034 (18)	−0.003 (2)
C6'A	0.019 (2)	0.023 (2)	0.042 (3)	−0.0013 (17)	−0.0001 (19)	0.001 (2)
S1B	0.0183 (5)	0.0276 (5)	0.0392 (6)	0.0017 (4)	0.0002 (4)	0.0039 (4)
O1B	0.0202 (14)	0.0205 (15)	0.0411 (17)	−0.0046 (12)	0.0037 (13)	0.0031 (12)
O2B	0.0285 (16)	0.0267 (16)	0.0386 (17)	−0.0036 (13)	0.0023 (13)	0.0059 (13)
O3B	0.0248 (17)	0.0217 (16)	0.0442 (18)	0.0022 (12)	0.0006 (13)	0.0063 (13)
O4B	0.0187 (15)	0.0370 (18)	0.0491 (19)	−0.0033 (13)	−0.0001 (14)	0.0041 (15)
Cl1B	0.0219 (5)	0.0543 (7)	0.0379 (6)	−0.0016 (5)	−0.0044 (5)	0.0037 (5)
Cl2B	0.0167 (5)	0.0340 (6)	0.0447 (6)	−0.0060 (4)	−0.0047 (4)	0.0021 (5)
Cl3B	0.0279 (6)	0.0455 (7)	0.0399 (6)	−0.0032 (5)	0.0037 (5)	0.0000 (6)
Cl4B	0.0802 (11)	0.0341 (6)	0.0545 (8)	−0.0139 (7)	−0.0252 (7)	0.0035 (5)
Cl5B	0.0709 (11)	0.0286 (7)	0.0465 (9)	0.0093 (7)	0.0109 (8)	0.0067 (7)
Cl6B	0.0715 (11)	0.0299 (8)	0.0454 (9)	0.0031 (7)	0.0054 (8)	0.0030 (7)
C1B	0.018 (2)	0.0134 (18)	0.040 (2)	0.0007 (16)	0.0015 (18)	0.0006 (17)
C2B	0.0137 (19)	0.023 (2)	0.045 (3)	−0.0001 (16)	−0.0014 (17)	0.0013 (19)
C3B	0.019 (2)	0.020 (2)	0.044 (2)	0.0014 (17)	−0.0017 (18)	0.0002 (18)
C4B	0.0122 (18)	0.0156 (19)	0.048 (3)	−0.0009 (15)	−0.0002 (18)	0.0014 (17)
C5B	0.017 (2)	0.0120 (18)	0.048 (3)	0.0000 (16)	0.0010 (18)	0.0004 (17)
C6B	0.020 (2)	0.022 (2)	0.040 (2)	−0.0008 (17)	−0.0039 (18)	−0.0016 (18)
C7B	0.033 (2)	0.027 (2)	0.038 (2)	0.001 (2)	−0.002 (2)	0.0039 (19)
C8B	0.060 (3)	0.028 (2)	0.041 (3)	−0.002 (2)	−0.007 (3)	0.000 (2)
C1'B	0.017 (2)	0.024 (2)	0.044 (2)	0.0023 (17)	−0.0018 (18)	−0.0069 (19)
C2'B	0.017 (2)	0.034 (3)	0.043 (2)	0.0000 (19)	−0.0038 (19)	0.000 (2)
C3'B	0.025 (2)	0.030 (2)	0.037 (2)	0.002 (2)	−0.005 (2)	0.000 (2)
C4'B	0.019 (2)	0.026 (2)	0.040 (2)	−0.0023 (18)	0.0028 (18)	−0.0037 (19)
C5'B	0.019 (2)	0.026 (2)	0.043 (3)	0.0008 (18)	−0.0034 (18)	−0.003 (2)
C6'B	0.019 (2)	0.023 (2)	0.042 (3)	−0.0013 (17)	−0.0001 (19)	0.001 (2)

S1A—O4A	1.408 (5)	S1B—O3B	1.396 (6)
S1A—O3A	1.414 (6)	S1B—O4B	1.409 (5)
S1A—O2A	1.563 (6)	S1B—O2B	1.563 (6)
S1A—O1A	1.600 (5)	S1B—O1B	1.590 (5)
O1A—C4A	1.393 (9)	O1B—C4B	1.397 (9)
O2A—C7A	1.464 (9)	O2B—C7B	1.434 (9)
Cl1A—C3A	1.722 (9)	Cl1B—C3B	1.720 (8)
Cl2A—C5A	1.749 (7)	Cl2B—C5B	1.726 (7)
Cl3A—C4'A	1.730 (8)	Cl3B—C4'B	1.739 (8)
Cl4A—C8A	1.783 (10)	Cl4B—C8B	1.793 (10)
Cl5A—C8A	1.772 (10)	Cl5B—C8B	1.755 (9)
Cl6A—C8A	1.774 (9)	Cl6B—C8B	1.774 (10)
C1A—C2A	1.391 (11)	C1B—C2B	1.378 (11)
C1A—C6A	1.400 (10)	C1B—C6B	1.412 (10)
C1A—C1'A	1.467 (10)	C1B—C1'B	1.510 (10)
C2A—C3A	1.390 (11)	C2B—C3B	1.389 (11)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.390 (10)	C3B—C4B	1.401 (10)
C4A—C5A	1.373 (11)	C4B—C5B	1.370 (11)
C5A—C6A	1.381 (11)	C5B—C6B	1.384 (11)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.500 (12)	C7B—C8B	1.509 (12)
C7A—H7A1	0.9900	C7B—H7B1	0.9900
C7A—H7A2	0.9900	C7B—H7B2	0.9900
C1'A—C6'A	1.399 (10)	C1'B—C2'B	1.373 (12)
C1'A—C2'A	1.400 (12)	C1'B—C6'B	1.393 (10)
C2'A—C3'A	1.380 (12)	C2'B—C3'B	1.391 (12)
C2'A—H2'A	0.9500	C2'B—H2'B	0.9500
C3'A—C4'A	1.389 (11)	C3'B—C4'B	1.364 (10)
C3'A—H3'A	0.9500	C3'B—H3'B	0.9500
C4'A—C5'A	1.369 (12)	C4'B—C5'B	1.392 (12)
C5'A—C6'A	1.388 (11)	C5'B—C6'B	1.399 (11)
C5'A—H5'A	0.9500	C5'B—H5'B	0.9500
C6'A—H6'A	0.9500	C6'B—H6'B	0.9500
O4A—S1A—O3A	121.2 (3)	O3B—S1B—O4B	122.7 (3)
O4A—S1A—O2A	109.9 (3)	O3B—S1B—O2B	105.6 (3)
O3A—S1A—O2A	106.0 (3)	O4B—S1B—O2B	110.3 (3)
O4A—S1A—O1A	106.0 (3)	O3B—S1B—O1B	109.4 (3)
O3A—S1A—O1A	110.5 (3)	O4B—S1B—O1B	105.4 (3)
O2A—S1A—O1A	101.4 (3)	O2B—S1B—O1B	101.4 (3)
C4A—O1A—S1A	119.3 (4)	C4B—O1B—S1B	120.0 (4)
C7A—O2A—S1A	117.1 (5)	C7B—O2B—S1B	117.5 (5)
C2A—C1A—C6A	118.1 (7)	C2B—C1B—C6B	120.1 (7)
C2A—C1A—C1'A	121.5 (7)	C2B—C1B—C1'B	119.9 (6)
C6A—C1A—C1'A	120.3 (7)	C6B—C1B—C1'B	120.0 (7)
C3A—C2A—C1A	121.1 (7)	C1B—C2B—C3B	120.8 (7)
C3A—C2A—H2A	119.5	C1B—C2B—H2B	119.6
C1A—C2A—H2A	119.5	C3B—C2B—H2B	119.6
C4A—C3A—C2A	120.0 (8)	C2B—C3B—C4B	119.3 (8)
C4A—C3A—Cl1A	120.1 (6)	C2B—C3B—Cl1B	119.9 (6)
C2A—C3A—Cl1A	119.8 (6)	C4B—C3B—Cl1B	120.7 (6)
C5A—C4A—C3A	119.0 (7)	C5B—C4B—O1B	120.6 (6)
C5A—C4A—O1A	120.1 (6)	C5B—C4B—C3B	119.5 (7)
C3A—C4A—O1A	120.5 (7)	O1B—C4B—C3B	119.8 (7)
C4A—C5A—C6A	121.5 (7)	C4B—C5B—C6B	122.2 (7)
C4A—C5A—Cl2A	118.8 (6)	C4B—C5B—Cl2B	118.7 (6)
C6A—C5A—Cl2A	119.7 (6)	C6B—C5B—Cl2B	119.0 (6)
C5A—C6A—C1A	120.3 (8)	C5B—C6B—C1B	118.1 (7)
C5A—C6A—H6A	119.9	C5B—C6B—H6B	121.0
C1A—C6A—H6A	119.9	C1B—C6B—H6B	121.0
O2A—C7A—C8A	105.4 (6)	O2B—C7B—C8B	108.2 (7)
O2A—C7A—H7A1	110.7	O2B—C7B—H7B1	110.0
C8A—C7A—H7A1	110.7	C8B—C7B—H7B1	110.0
O2A—C7A—H7A2	110.7	O2B—C7B—H7B2	110.0
C8A—C7A—H7A2	110.7	C8B—C7B—H7B2	110.0
H7A1—C7A—H7A2	108.8	H7B1—C7B—H7B2	108.4
C7A—C8A—Cl5A	112.5 (6)	C7B—C8B—Cl5B	108.6 (6)
C7A—C8A—Cl6A	106.7 (6)	C7B—C8B—Cl6B	108.2 (6)
Cl5A—C8A—Cl6A	109.3 (5)	Cl5B—C8B—Cl6B	110.8 (6)
C7A—C8A—Cl4A	110.8 (7)	C7B—C8B—Cl4B	109.5 (7)
Cl5A—C8A—Cl4A	108.6 (5)	Cl5B—C8B—Cl4B	110.0 (5)
Cl6A—C8A—Cl4A	108.8 (5)	Cl6B—C8B—Cl4B	109.7 (5)
C6'A—C1'A—C2'A	118.2 (7)	C2'B—C1'B—C6'B	118.9 (7)
C6'A—C1'A—C1A	120.1 (7)	C2'B—C1'B—C1B	120.7 (6)
C2'A—C1'A—C1A	121.6 (6)	C6'B—C1'B—C1B	120.4 (7)
C3'A—C2'A—C1'A	121.3 (7)	C1'B—C2'B—C3'B	121.2 (7)
C3'A—C2'A—H2'A	119.3	C1'B—C2'B—H2'B	119.4
C1'A—C2'A—H2'A	119.3	C3'B—C2'B—H2'B	119.4
C2'A—C3'A—C4'A	119.3 (8)	C4'B—C3'B—C2'B	119.4 (8)
C2'A—C3'A—H3'A	120.3	C4'B—C3'B—H3'B	120.3
C4'A—C3'A—H3'A	120.3	C2'B—C3'B—H3'B	120.3
C5'A—C4'A—C3'A	120.3 (7)	C3'B—C4'B—C5'B	121.3 (8)
C5'A—C4'A—Cl3A	120.7 (6)	C3'B—C4'B—Cl3B	120.7 (7)
C3'A—C4'A—Cl3A	118.9 (7)	C5'B—C4'B—Cl3B	118.0 (6)
C4'A—C5'A—C6'A	120.7 (7)	C4'B—C5'B—C6'B	118.5 (7)
C4'A—C5'A—H5'A	119.6	C4'B—C5'B—H5'B	120.8
C6'A—C5'A—H5'A	119.6	C6'B—C5'B—H5'B	120.8
C5'A—C6'A—C1'A	120.0 (8)	C1'B—C6'B—C5'B	120.6 (8)
C5'A—C6'A—H6'A	120.0	C1'B—C6'B—H6'B	119.7
C1'A—C6'A—H6'A	120.0	C5'B—C6'B—H6'B	119.7
O4A—S1A—O1A—C4A	138.7 (5)	O3B—S1B—O1B—C4B	−4.9 (6)
O3A—S1A—O1A—C4A	5.6 (6)	O4B—S1B—O1B—C4B	−138.6 (6)
O2A—S1A—O1A—C4A	−106.4 (5)	O2B—S1B—O1B—C4B	106.3 (6)
O4A—S1A—O2A—C7A	45.2 (6)	O3B—S1B—O2B—C7B	−177.9 (5)
O3A—S1A—O2A—C7A	177.8 (5)	O4B—S1B—O2B—C7B	−43.3 (6)
O1A—S1A—O2A—C7A	−66.7 (5)	O1B—S1B—O2B—C7B	68.0 (6)
C6A—C1A—C2A—C3A	−1.2 (11)	C6B—C1B—C2B—C3B	3.1 (11)
C1'A—C1A—C2A—C3A	177.5 (7)	C1'B—C1B—C2B—C3B	−178.2 (7)
C1A—C2A—C3A—C4A	0.9 (11)	C1B—C2B—C3B—C4B	−2.3 (11)
C1A—C2A—C3A—Cl1A	−178.0 (6)	C1B—C2B—C3B—Cl1B	179.7 (6)
C2A—C3A—C4A—C5A	1.0 (11)	S1B—O1B—C4B—C5B	91.6 (8)
Cl1A—C3A—C4A—C5A	179.9 (5)	S1B—O1B—C4B—C3B	−92.2 (7)
C2A—C3A—C4A—O1A	174.4 (6)	C2B—C3B—C4B—C5B	1.6 (11)
Cl1A—C3A—C4A—O1A	−6.7 (10)	Cl1B—C3B—C4B—C5B	179.5 (6)
S1A—O1A—C4A—C5A	−92.0 (7)	C2B—C3B—C4B—O1B	−174.6 (6)
S1A—O1A—C4A—C3A	94.7 (7)	Cl1B—C3B—C4B—O1B	3.3 (10)
C3A—C4A—C5A—C6A	−2.6 (11)	O1B—C4B—C5B—C6B	174.4 (6)
O1A—C4A—C5A—C6A	−176.0 (6)	C3B—C4B—C5B—C6B	−1.8 (11)
C3A—C4A—C5A—Cl2A	177.1 (5)	O1B—C4B—C5B—Cl2B	−2.3 (10)
O1A—C4A—C5A—Cl2A	3.7 (9)	C3B—C4B—C5B—Cl2B	−178.5 (5)
C4A—C5A—C6A—C1A	2.3 (11)	C4B—C5B—C6B—C1B	2.5 (11)
Cl2A—C5A—C6A—C1A	−177.4 (5)	Cl2B—C5B—C6B—C1B	179.2 (5)
C2A—C1A—C6A—C5A	−0.4 (11)	C2B—C1B—C6B—C5B	−3.2 (11)
C1'A—C1A—C6A—C5A	−179.1 (6)	C1'B—C1B—C6B—C5B	178.2 (6)
S1A—O2A—C7A—C8A	−148.3 (6)	S1B—O2B—C7B—C8B	148.2 (6)
O2A—C7A—C8A—Cl5A	58.7 (8)	O2B—C7B—C8B—Cl5B	−180.0 (5)
O2A—C7A—C8A—Cl6A	178.5 (5)	O2B—C7B—C8B—Cl6B	−59.6 (8)
O2A—C7A—C8A—Cl4A	−63.2 (7)	O2B—C7B—C8B—Cl4B	59.9 (8)
C2A—C1A—C1'A—C6'A	36.2 (11)	C2B—C1B—C1'B—C2'B	145.8 (8)
C6A—C1A—C1'A—C6'A	−145.1 (7)	C6B—C1B—C1'B—C2'B	−35.5 (11)
C2A—C1A—C1'A—C2'A	−140.7 (8)	C2B—C1B—C1'B—C6'B	−34.4 (11)
C6A—C1A—C1'A—C2'A	38.0 (11)	C6B—C1B—C1'B—C6'B	144.2 (7)
C6'A—C1'A—C2'A—C3'A	0.1 (12)	C6'B—C1'B—C2'B—C3'B	0.8 (12)
C1A—C1'A—C2'A—C3'A	177.0 (7)	C1B—C1'B—C2'B—C3'B	−179.4 (7)
C1'A—C2'A—C3'A—C4'A	−0.5 (12)	C1'B—C2'B—C3'B—C4'B	0.0 (13)
C2'A—C3'A—C4'A—C5'A	1.7 (12)	C2'B—C3'B—C4'B—C5'B	−0.5 (12)
C2'A—C3'A—C4'A—Cl3A	−177.9 (6)	C2'B—C3'B—C4'B—Cl3B	178.5 (6)
C3'A—C4'A—C5'A—C6'A	−2.4 (12)	C3'B—C4'B—C5'B—C6'B	0.3 (12)
Cl3A—C4'A—C5'A—C6'A	177.1 (6)	Cl3B—C4'B—C5'B—C6'B	−178.8 (6)
C4'A—C5'A—C6'A—C1'A	2.0 (12)	C2'B—C1'B—C6'B—C5'B	−1.1 (12)
C2'A—C1'A—C6'A—C5'A	−0.8 (11)	C1B—C1'B—C6'B—C5'B	179.2 (7)
C1A—C1'A—C6'A—C5'A	−177.8 (7)	C4'B—C5'B—C6'B—C1'B	0.5 (11)