4'-Chloro-biphenyl-4-yl 2,2,2-trichloro-ethyl sulfate.

The title compound, C(14)H(10)Cl(4)O(4)S, is an inter-mediate in the synthesis of the PCB sulfate monoester of 4'-chloro-biphenyl-4-ol. Both the sulfate monoester and 4'-chloro-biphenyl-4-ol are metabolites of PCB 3 (4-chloro-biphen-yl). There are two mol-ecules with different conformations in the asymmetric unit. The solid state dihedral angles between the benzene rings are 18.52 (10) and 41.84 (16)° in the two mol-ecules, whereas the dihedral angles between the least-squares plane of the sulfated benzene ring and O-S (Ar-C-O-S) are 66.2 (3) and 89.3 (3)°. The crystal was an inversion twin with a refined component fraction of 0.44 (7).

Related literature

For similar structures of hydroxy­lated chloro­biphenyls and their derivatives, see: Rissanen et al. (1988a ▶,b ▶); Lehmler et al. (2001 ▶, 2002 ▶); Desiraju et al. (1979 ▶); Vyas et al. (2006 ▶). For a review of structures of sulfuric acid aryl mono esters, see: Brandao et al. (2005 ▶). For additional background, see: Letcher et al. (2000 ▶); Liu et al. (2004 ▶, 2006 ▶); Sacco & James (2005 ▶); Shaikh et al. (2008 ▶); Tampal et al. (2002 ▶); Hansen (1999 ▶); Robertson & Hansen (2001 ▶).

Experimental

Crystal data

C14H10Cl4O4S

M = 416.08

Orthorhombic,

a = 9.6305 (19) Å

b = 30.273 (6) Å

c = 11.330 (2) Å

V = 3303.3 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.86 mm−1

T = 90.0 (2) K

0.40 × 0.34 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.679, T max = 0.861

25566 measured reflections

6476 independent reflections

4862 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.109

S = 1.05

6476 reflections

415 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.56 e Å−3

Absolute structure: Flack (1983 ▶), 2481 Friedel Pairs

Flack parameter: 0.44 (7)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038865/dn2403sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038865/dn2403Isup2.hkl

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

C14H10Cl4O4S	F000 = 1680
Mr = 416.08	Dx = 1.673 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4257 reflections
a = 9.6305 (19) Å	θ = 1.0–27.5º
b = 30.273 (6) Å	µ = 0.86 mm−1
c = 11.330 (2) Å	T = 90.0 (2) K
V = 3303.3 (11) Å3	Block, colourless
Z = 8	0.40 × 0.34 × 0.18 mm

Nonius KappaCCD diffractometer	6476 independent reflections
Radiation source: fine-focus sealed tube	4862 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.063
Detector resolution: 18 pixels mm-1	θmax = 27.5º
T = 90.0(2) K	θmin = 2.2º
ω scans at fixed χ = 55°	h = −12→12
Absorption correction: multi-scan(SCALEPACK; Otwinowski & Minor, 1997)	k = −39→38
Tmin = 0.679, Tmax = 0.861	l = −11→14
25566 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0569P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.51 e Å−3
6476 reflections	Δρmin = −0.56 e Å−3
415 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 2481 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.44 (7)
Secondary atom site location: difference Fourier map

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
S1A	0.37972 (11)	0.52517 (4)	0.22349 (11)	0.0182 (3)
O1A	0.4951 (3)	0.55663 (9)	0.2732 (3)	0.0189 (7)
O2A	0.3525 (3)	0.49236 (9)	0.3284 (3)	0.0162 (7)
O3A	0.2535 (3)	0.54799 (8)	0.2091 (3)	0.0228 (7)
O4A	0.4438 (3)	0.50234 (10)	0.1291 (3)	0.0219 (7)
Cl1A	0.32327 (13)	0.81401 (4)	0.83893 (12)	0.0332 (3)
Cl2A	0.34106 (12)	0.39176 (4)	0.28495 (11)	0.0249 (3)
Cl3A	0.55811 (11)	0.39177 (4)	0.46162 (11)	0.0250 (3)
Cl4A	0.28608 (11)	0.42787 (4)	0.51617 (10)	0.0251 (3)
C1A	0.4100 (4)	0.66199 (14)	0.5036 (4)	0.0185 (10)
C2A	0.4593 (5)	0.66887 (14)	0.3888 (4)	0.0253 (10)
H2A	0.4777	0.6981	0.3627	0.030*
C3A	0.4817 (4)	0.63383 (14)	0.3129 (4)	0.0255 (11)
H3A	0.5129	0.6390	0.2346	0.031*
C4A	0.4583 (4)	0.59162 (14)	0.3517 (4)	0.0169 (10)
C5A	0.4137 (4)	0.58287 (15)	0.4644 (4)	0.0192 (10)
H5A	0.4002	0.5534	0.4905	0.023*
C6A	0.3889 (4)	0.61848 (14)	0.5396 (4)	0.0203 (11)
H6A	0.3567	0.6129	0.6174	0.024*
C7A	0.4706 (4)	0.46577 (13)	0.3666 (4)	0.0171 (10)
H7A1	0.5192	0.4804	0.4329	0.021*
H7A2	0.5371	0.4619	0.3008	0.021*
C8A	0.4136 (4)	0.42113 (14)	0.4058 (4)	0.0174 (10)
C1'A	0.3849 (4)	0.69949 (14)	0.5865 (4)	0.0202 (10)
C2'A	0.3782 (4)	0.69245 (14)	0.7090 (4)	0.0229 (10)
H2'A	0.3882	0.6634	0.7393	0.028*
C3'A	0.3573 (5)	0.72738 (14)	0.7862 (4)	0.0278 (11)
H3'A	0.3519	0.7224	0.8689	0.033*
C4'A	0.3444 (5)	0.76930 (14)	0.7414 (4)	0.0215 (11)
C5'A	0.3477 (4)	0.77735 (13)	0.6205 (4)	0.0265 (11)
H5'A	0.3351	0.8064	0.5905	0.032*
C6'A	0.3696 (5)	0.74235 (14)	0.5456 (4)	0.0259 (11)
H6'A	0.3744	0.7477	0.4631	0.031*
S1B	0.36151 (11)	0.02678 (3)	0.20279 (10)	0.0170 (2)
O1B	0.4725 (3)	0.06109 (9)	0.1597 (3)	0.0197 (7)
O2B	0.3431 (3)	−0.00442 (9)	0.0931 (3)	0.0180 (7)
O3B	0.2310 (3)	0.04755 (8)	0.2178 (3)	0.0214 (7)
O4B	0.4277 (3)	0.00352 (10)	0.2956 (3)	0.0210 (7)
Cl1B	0.29897 (13)	0.31088 (4)	−0.42521 (12)	0.0308 (3)
Cl2B	0.30154 (11)	−0.06864 (4)	−0.10670 (11)	0.0226 (3)
Cl3B	0.55924 (11)	−0.10661 (4)	−0.02190 (12)	0.0258 (3)
Cl4B	0.31521 (12)	−0.10380 (4)	0.12863 (11)	0.0249 (3)
C1B	0.3812 (5)	0.16175 (14)	−0.0805 (4)	0.0198 (10)
C2B	0.4206 (4)	0.12024 (14)	−0.1204 (4)	0.0201 (10)
H2B	0.4293	0.1149	−0.2027	0.024*
C3B	0.4471 (4)	0.08652 (15)	−0.0409 (5)	0.0223 (11)
H3B	0.4745	0.0581	−0.0680	0.027*
C4B	0.4335 (4)	0.09461 (14)	0.0765 (5)	0.0183 (10)
C5B	0.3896 (4)	0.13457 (13)	0.1210 (4)	0.0225 (10)
H5B	0.3788	0.1390	0.2035	0.027*
C6B	0.3617 (5)	0.16827 (13)	0.0406 (4)	0.0218 (10)
H6B	0.3291	0.1960	0.0684	0.026*
C7B	0.4627 (4)	−0.03186 (14)	0.0616 (4)	0.0182 (10)
H7B1	0.5231	−0.0362	0.1313	0.022*
H7B2	0.5177	−0.0173	−0.0011	0.022*
C8B	0.4097 (4)	−0.07557 (14)	0.0186 (4)	0.0171 (10)
C1'B	0.3608 (4)	0.19884 (14)	−0.1657 (4)	0.0189 (10)
C2'B	0.2482 (5)	0.22865 (12)	−0.1553 (4)	0.0239 (10)
H2'B	0.1834	0.2250	−0.0928	0.029*
C3'B	0.2307 (5)	0.26276 (13)	−0.2336 (4)	0.0236 (10)
H3'B	0.1553	0.2827	−0.2245	0.028*
C4'B	0.3228 (5)	0.26804 (14)	−0.3252 (4)	0.0226 (11)
C5'B	0.4350 (5)	0.23942 (14)	−0.3388 (4)	0.0247 (11)
H5'B	0.4992	0.2435	−0.4016	0.030*
C6'B	0.4515 (5)	0.20517 (14)	−0.2599 (4)	0.0243 (10)
H6'B	0.5270	0.1853	−0.2700	0.029*

	U11	U22	U33	U12	U13	U23
S1A	0.0188 (5)	0.0180 (6)	0.0177 (6)	−0.0007 (4)	0.0011 (5)	0.0019 (5)
O1A	0.0170 (15)	0.0174 (15)	0.0223 (18)	−0.0042 (12)	0.0023 (14)	0.0009 (14)
O2A	0.0143 (14)	0.0185 (15)	0.0160 (18)	−0.0006 (12)	0.0034 (14)	0.0059 (14)
O3A	0.0188 (15)	0.0225 (15)	0.0270 (19)	0.0033 (14)	−0.0026 (15)	0.0035 (15)
O4A	0.0294 (17)	0.0197 (16)	0.0167 (18)	0.0004 (14)	0.0044 (14)	−0.0007 (14)
Cl1A	0.0430 (7)	0.0242 (6)	0.0323 (7)	−0.0018 (5)	−0.0001 (6)	−0.0100 (6)
Cl2A	0.0281 (6)	0.0220 (6)	0.0245 (7)	−0.0004 (5)	−0.0071 (5)	−0.0060 (5)
Cl3A	0.0226 (6)	0.0234 (6)	0.0289 (7)	0.0048 (5)	−0.0031 (5)	0.0023 (5)
Cl4A	0.0253 (6)	0.0273 (6)	0.0227 (6)	0.0025 (5)	0.0079 (5)	0.0047 (5)
C1A	0.019 (2)	0.020 (2)	0.016 (2)	0.0015 (18)	−0.003 (2)	0.000 (2)
C2A	0.031 (3)	0.018 (2)	0.027 (3)	−0.001 (2)	0.002 (2)	0.007 (2)
C3A	0.029 (3)	0.026 (2)	0.022 (3)	0.001 (2)	0.006 (2)	0.005 (2)
C4A	0.015 (2)	0.013 (2)	0.023 (3)	0.0012 (17)	−0.001 (2)	−0.0001 (19)
C5A	0.022 (2)	0.020 (2)	0.016 (2)	0.0024 (18)	0.002 (2)	0.002 (2)
C6A	0.017 (2)	0.019 (2)	0.024 (3)	−0.0005 (19)	−0.002 (2)	0.002 (2)
C7A	0.017 (2)	0.020 (2)	0.014 (2)	0.0019 (19)	−0.0016 (19)	0.002 (2)
C8A	0.014 (2)	0.018 (2)	0.020 (3)	0.0034 (18)	0.002 (2)	0.003 (2)
C1'A	0.019 (2)	0.020 (2)	0.021 (3)	−0.0009 (19)	0.001 (2)	0.005 (2)
C2'A	0.030 (3)	0.016 (2)	0.023 (2)	0.0041 (19)	0.003 (2)	0.001 (2)
C3'A	0.030 (3)	0.028 (3)	0.026 (3)	0.004 (2)	0.001 (2)	0.001 (2)
C4'A	0.022 (2)	0.019 (2)	0.023 (3)	−0.0030 (18)	−0.004 (2)	−0.010 (2)
C5'A	0.030 (3)	0.015 (2)	0.035 (3)	−0.0022 (19)	0.000 (2)	0.000 (2)
C6'A	0.028 (3)	0.020 (2)	0.029 (3)	0.001 (2)	0.003 (2)	0.001 (2)
S1B	0.0177 (5)	0.0161 (5)	0.0173 (6)	−0.0012 (4)	−0.0013 (5)	0.0001 (5)
O1B	0.0210 (15)	0.0143 (15)	0.0237 (19)	−0.0025 (13)	−0.0017 (14)	0.0024 (14)
O2B	0.0156 (15)	0.0191 (16)	0.0192 (19)	0.0025 (12)	−0.0009 (15)	−0.0058 (14)
O3B	0.0179 (15)	0.0198 (15)	0.0265 (18)	0.0001 (13)	−0.0005 (15)	−0.0040 (15)
O4B	0.0246 (16)	0.0219 (17)	0.0166 (18)	0.0001 (14)	−0.0045 (14)	0.0031 (15)
Cl1B	0.0450 (8)	0.0191 (6)	0.0285 (7)	−0.0008 (5)	−0.0068 (6)	0.0054 (5)
Cl2B	0.0221 (5)	0.0255 (6)	0.0203 (6)	−0.0011 (5)	−0.0054 (5)	−0.0012 (5)
Cl3B	0.0193 (6)	0.0255 (6)	0.0326 (7)	0.0056 (5)	−0.0011 (5)	−0.0071 (6)
Cl4B	0.0291 (6)	0.0221 (6)	0.0235 (6)	−0.0017 (5)	0.0031 (5)	0.0044 (5)
C1B	0.021 (2)	0.014 (2)	0.024 (3)	−0.0032 (18)	0.002 (2)	−0.003 (2)
C2B	0.022 (2)	0.016 (2)	0.022 (3)	−0.0002 (19)	0.002 (2)	−0.003 (2)
C3B	0.016 (2)	0.020 (2)	0.031 (3)	0.0001 (18)	0.002 (2)	−0.003 (2)
C4B	0.015 (2)	0.016 (2)	0.024 (3)	0.0002 (18)	−0.003 (2)	0.004 (2)
C5B	0.026 (2)	0.022 (2)	0.020 (2)	−0.0012 (19)	0.001 (2)	−0.003 (2)
C6B	0.026 (2)	0.011 (2)	0.028 (3)	0.0037 (19)	0.003 (2)	−0.0006 (19)
C7B	0.015 (2)	0.018 (2)	0.022 (3)	0.0026 (19)	−0.002 (2)	−0.004 (2)
C8B	0.015 (2)	0.018 (2)	0.019 (2)	0.0035 (18)	0.001 (2)	0.004 (2)
C1'B	0.024 (2)	0.014 (2)	0.019 (3)	−0.0047 (18)	−0.002 (2)	−0.002 (2)
C2'B	0.021 (2)	0.022 (2)	0.029 (3)	−0.0005 (19)	0.005 (2)	−0.002 (2)
C3'B	0.029 (3)	0.015 (2)	0.026 (3)	0.0048 (19)	−0.003 (2)	−0.0025 (19)
C4'B	0.030 (3)	0.014 (2)	0.024 (3)	−0.0054 (19)	−0.013 (2)	0.000 (2)
C5'B	0.029 (3)	0.026 (2)	0.019 (2)	−0.011 (2)	0.001 (2)	0.002 (2)
C6'B	0.026 (2)	0.020 (2)	0.027 (3)	−0.001 (2)	0.003 (2)	−0.005 (2)

S1A—O3A	1.408 (3)	S1B—O3B	1.415 (3)
S1A—O4A	1.415 (3)	S1B—O4B	1.417 (3)
S1A—O1A	1.568 (3)	S1B—O1B	1.568 (3)
S1A—O2A	1.571 (3)	S1B—O2B	1.571 (3)
O1A—C4A	1.427 (5)	O1B—C4B	1.435 (5)
O2A—C7A	1.459 (5)	O2B—C7B	1.464 (5)
Cl1A—C4'A	1.759 (5)	Cl1B—C4'B	1.738 (5)
Cl2A—C8A	1.776 (5)	Cl2B—C8B	1.773 (5)
Cl3A—C8A	1.768 (4)	Cl3B—C8B	1.780 (4)
Cl4A—C8A	1.765 (5)	Cl4B—C8B	1.764 (5)
C1A—C6A	1.394 (6)	C1B—C2B	1.388 (6)
C1A—C2A	1.400 (7)	C1B—C6B	1.399 (6)
C1A—C1'A	1.493 (6)	C1B—C1'B	1.494 (6)
C2A—C3A	1.383 (6)	C2B—C3B	1.386 (6)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.370 (6)	C3B—C4B	1.358 (7)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.373 (7)	C4B—C5B	1.377 (6)
C5A—C6A	1.395 (6)	C5B—C6B	1.394 (6)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.524 (6)	C7B—C8B	1.499 (6)
C7A—H7A1	0.9900	C7B—H7B1	0.9900
C7A—H7A2	0.9900	C7B—H7B2	0.9900
C1'A—C6'A	1.386 (6)	C1'B—C6'B	1.392 (6)
C1'A—C2'A	1.406 (7)	C1'B—C2'B	1.416 (6)
C2'A—C3'A	1.387 (6)	C2'B—C3'B	1.371 (6)
C2'A—H2'A	0.9500	C2'B—H2'B	0.9500
C3'A—C4'A	1.372 (6)	C3'B—C4'B	1.375 (7)
C3'A—H3'A	0.9500	C3'B—H3'B	0.9500
C4'A—C5'A	1.392 (7)	C4'B—C5'B	1.394 (6)
C5'A—C6'A	1.374 (6)	C5'B—C6'B	1.379 (6)
C5'A—H5'A	0.9500	C5'B—H5'B	0.9500
C6'A—H6'A	0.9500	C6'B—H6'B	0.9500
O3A—S1A—O4A	121.9 (2)	O3B—S1B—O4B	122.1 (2)
O3A—S1A—O1A	110.81 (17)	O3B—S1B—O1B	110.36 (16)
O4A—S1A—O1A	105.03 (18)	O4B—S1B—O1B	104.70 (17)
O3A—S1A—O2A	104.68 (17)	O3B—S1B—O2B	105.19 (17)
O4A—S1A—O2A	109.64 (18)	O4B—S1B—O2B	109.83 (18)
O1A—S1A—O2A	103.31 (17)	O1B—S1B—O2B	103.20 (17)
C4A—O1A—S1A	119.9 (3)	C4B—O1B—S1B	119.7 (3)
C7A—O2A—S1A	116.3 (2)	C7B—O2B—S1B	116.5 (3)
C6A—C1A—C2A	117.5 (4)	C2B—C1B—C6B	118.9 (4)
C6A—C1A—C1'A	120.7 (4)	C2B—C1B—C1'B	120.4 (4)
C2A—C1A—C1'A	121.7 (4)	C6B—C1B—C1'B	120.7 (4)
C3A—C2A—C1A	121.1 (4)	C3B—C2B—C1B	120.4 (5)
C3A—C2A—H2A	119.4	C3B—C2B—H2B	119.8
C1A—C2A—H2A	119.4	C1B—C2B—H2B	119.8
C4A—C3A—C2A	119.3 (4)	C4B—C3B—C2B	119.1 (5)
C4A—C3A—H3A	120.3	C4B—C3B—H3B	120.5
C2A—C3A—H3A	120.3	C2B—C3B—H3B	120.5
C3A—C4A—C5A	122.0 (4)	C3B—C4B—C5B	123.1 (5)
C3A—C4A—O1A	116.8 (4)	C3B—C4B—O1B	119.4 (4)
C5A—C4A—O1A	120.9 (4)	C5B—C4B—O1B	117.4 (4)
C4A—C5A—C6A	118.2 (4)	C4B—C5B—C6B	117.6 (4)
C4A—C5A—H5A	120.9	C4B—C5B—H5B	121.2
C6A—C5A—H5A	120.9	C6B—C5B—H5B	121.2
C1A—C6A—C5A	121.8 (4)	C5B—C6B—C1B	120.8 (4)
C1A—C6A—H6A	119.1	C5B—C6B—H6B	119.6
C5A—C6A—H6A	119.1	C1B—C6B—H6B	119.6
O2A—C7A—C8A	107.1 (3)	O2B—C7B—C8B	108.2 (3)
O2A—C7A—H7A1	110.3	O2B—C7B—H7B1	110.1
C8A—C7A—H7A1	110.3	C8B—C7B—H7B1	110.1
O2A—C7A—H7A2	110.3	O2B—C7B—H7B2	110.1
C8A—C7A—H7A2	110.3	C8B—C7B—H7B2	110.1
H7A1—C7A—H7A2	108.5	H7B1—C7B—H7B2	108.4
C7A—C8A—Cl4A	110.8 (3)	C7B—C8B—Cl4B	111.9 (3)
C7A—C8A—Cl3A	105.5 (3)	C7B—C8B—Cl2B	110.8 (3)
Cl4A—C8A—Cl3A	110.6 (3)	Cl4B—C8B—Cl2B	108.7 (2)
C7A—C8A—Cl2A	111.2 (3)	C7B—C8B—Cl3B	105.9 (3)
Cl4A—C8A—Cl2A	109.3 (2)	Cl4B—C8B—Cl3B	110.1 (2)
Cl3A—C8A—Cl2A	109.5 (2)	Cl2B—C8B—Cl3B	109.4 (3)
C6'A—C1'A—C2'A	117.9 (4)	C6'B—C1'B—C2'B	117.2 (4)
C6'A—C1'A—C1A	121.3 (4)	C6'B—C1'B—C1B	121.1 (4)
C2'A—C1'A—C1A	120.9 (4)	C2'B—C1'B—C1B	121.7 (4)
C3'A—C2'A—C1'A	120.9 (4)	C3'B—C2'B—C1'B	121.3 (4)
C3'A—C2'A—H2'A	119.5	C3'B—C2'B—H2'B	119.4
C1'A—C2'A—H2'A	119.5	C1'B—C2'B—H2'B	119.4
C4'A—C3'A—C2'A	119.0 (4)	C2'B—C3'B—C4'B	119.8 (4)
C4'A—C3'A—H3'A	120.5	C2'B—C3'B—H3'B	120.1
C2'A—C3'A—H3'A	120.5	C4'B—C3'B—H3'B	120.1
C3'A—C4'A—C5'A	121.6 (4)	C3'B—C4'B—C5'B	120.8 (4)
C3'A—C4'A—Cl1A	119.3 (4)	C3'B—C4'B—Cl1B	119.6 (4)
C5'A—C4'A—Cl1A	119.1 (4)	C5'B—C4'B—Cl1B	119.6 (4)
C6'A—C5'A—C4'A	118.5 (4)	C6'B—C5'B—C4'B	119.0 (4)
C6'A—C5'A—H5'A	120.8	C6'B—C5'B—H5'B	120.5
C4'A—C5'A—H5'A	120.8	C4'B—C5'B—H5'B	120.5
C5'A—C6'A—C1'A	122.1 (5)	C5'B—C6'B—C1'B	121.9 (4)
C5'A—C6'A—H6'A	118.9	C5'B—C6'B—H6'B	119.0
C1'A—C6'A—H6'A	118.9	C1'B—C6'B—H6'B	119.0
O3A—S1A—O1A—C4A	32.4 (4)	O3B—S1B—O1B—C4B	−38.3 (4)
O4A—S1A—O1A—C4A	165.9 (3)	O4B—S1B—O1B—C4B	−171.3 (3)
O2A—S1A—O1A—C4A	−79.2 (3)	O2B—S1B—O1B—C4B	73.7 (3)
O3A—S1A—O2A—C7A	−176.8 (3)	O3B—S1B—O2B—C7B	−177.1 (3)
O4A—S1A—O2A—C7A	50.8 (3)	O4B—S1B—O2B—C7B	−44.0 (4)
O1A—S1A—O2A—C7A	−60.8 (3)	O1B—S1B—O2B—C7B	67.2 (3)
C6A—C1A—C2A—C3A	2.1 (7)	C6B—C1B—C2B—C3B	−3.4 (7)
C1'A—C1A—C2A—C3A	−179.8 (4)	C1'B—C1B—C2B—C3B	176.3 (4)
C1A—C2A—C3A—C4A	−1.6 (7)	C1B—C2B—C3B—C4B	0.3 (6)
C2A—C3A—C4A—C5A	−0.3 (7)	C2B—C3B—C4B—C5B	2.3 (7)
C2A—C3A—C4A—O1A	−174.5 (4)	C2B—C3B—C4B—O1B	−174.6 (4)
S1A—O1A—C4A—C3A	−116.3 (4)	S1B—O1B—C4B—C3B	−90.7 (4)
S1A—O1A—C4A—C5A	69.5 (5)	S1B—O1B—C4B—C5B	92.3 (4)
C3A—C4A—C5A—C6A	1.6 (7)	C3B—C4B—C5B—C6B	−1.6 (7)
O1A—C4A—C5A—C6A	175.5 (4)	O1B—C4B—C5B—C6B	175.3 (4)
C2A—C1A—C6A—C5A	−0.8 (6)	C4B—C5B—C6B—C1B	−1.6 (7)
C1'A—C1A—C6A—C5A	−179.0 (4)	C2B—C1B—C6B—C5B	4.0 (7)
C4A—C5A—C6A—C1A	−1.0 (7)	C1'B—C1B—C6B—C5B	−175.7 (4)
S1A—O2A—C7A—C8A	−146.0 (3)	S1B—O2B—C7B—C8B	143.8 (3)
O2A—C7A—C8A—Cl4A	−55.9 (4)	O2B—C7B—C8B—Cl4B	−61.5 (4)
O2A—C7A—C8A—Cl3A	−175.6 (3)	O2B—C7B—C8B—Cl2B	59.9 (4)
O2A—C7A—C8A—Cl2A	65.8 (4)	O2B—C7B—C8B—Cl3B	178.4 (3)
C6A—C1A—C1'A—C6'A	−162.8 (4)	C2B—C1B—C1'B—C6'B	−41.0 (6)
C2A—C1A—C1'A—C6'A	19.1 (7)	C6B—C1B—C1'B—C6'B	138.6 (5)
C6A—C1A—C1'A—C2'A	18.2 (6)	C2B—C1B—C1'B—C2'B	138.2 (5)
C2A—C1A—C1'A—C2'A	−159.9 (4)	C6B—C1B—C1'B—C2'B	−42.1 (6)
C6'A—C1'A—C2'A—C3'A	−0.1 (7)	C6'B—C1'B—C2'B—C3'B	−1.1 (7)
C1A—C1'A—C2'A—C3'A	178.9 (4)	C1B—C1'B—C2'B—C3'B	179.6 (4)
C1'A—C2'A—C3'A—C4'A	−0.7 (7)	C1'B—C2'B—C3'B—C4'B	0.9 (7)
C2'A—C3'A—C4'A—C5'A	2.0 (7)	C2'B—C3'B—C4'B—C5'B	−0.8 (7)
C2'A—C3'A—C4'A—Cl1A	−178.0 (3)	C2'B—C3'B—C4'B—Cl1B	179.2 (3)
C3'A—C4'A—C5'A—C6'A	−2.5 (7)	C3'B—C4'B—C5'B—C6'B	0.9 (7)
Cl1A—C4'A—C5'A—C6'A	177.6 (3)	Cl1B—C4'B—C5'B—C6'B	−179.0 (3)
C4'A—C5'A—C6'A—C1'A	1.6 (7)	C4'B—C5'B—C6'B—C1'B	−1.2 (7)
C2'A—C1'A—C6'A—C5'A	−0.4 (7)	C2'B—C1'B—C6'B—C5'B	1.3 (7)
C1A—C1'A—C6'A—C5'A	−179.4 (4)	C1B—C1'B—C6'B—C5'B	−179.5 (4)