3-(7,7-Di­methyl-2-oxobi­cyclo­[2.2.1.]­hept-1-yl­methane­sulfonyl­oxy)-2-methyl-2-(toluene-4-sulfonyl­oxy­methyl)­propyl 4-chloro­benzoate

The title compound, C₂₉H₃₅ClO₉S₂, is a tris­(hydroxy­methyl)­ethane derivative with an asymmetric carbon in the propane skeleton. Surprisingly, in the unit cell, two stereoisomers with different configuration at this centre are present. Their relative orientation gives a nearly centrosymmetric arrangement, and all corresponding bond lengths and angles are comparable in the two mol­ecules. Two additional chiral centres with S-configurations present in the camphor­sulfonic acid group have to be the same in both mol­ecules, rendering the two compounds diastereomers.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.078
• Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.45
         From the CIF: _reflns_number_total              10443
         Count of symmetry unique reflns         7006
         Completeness (_total/calc)            149.06%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      3437
         Fraction of Friedel pairs measured     0.491
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

---

S1. Comment

2-Hydroxymethyl-2-methyl-3-(toluene-4-sulfonyloxy)propyl 4-chlorobenzoate with high enantiomeric purity was treated with (1S)-camphorsulfonic acid chloride to yield the title compound, (I) (von Matt et al., 1995). ¹H NMR analysis of the resulting colourless solid showed a high diastereomeric excess. Treatment with a 4:1 mixture of hexane and methanol yielded a small amount of crystals suitable for X-ray diffraction. The structure given in Fig. 1 shows there are actually two compounds present in the unit cell. Removal of the camphorsulfonic acid group would leave two centrosymmetrically related molecules with the tosylate groups facing each other. The corresponding bond lengths and angles of both molecules are nearly identical and the configuration at both C114 and C214 is S. They differ only in the configuration of their central asymmetric carbon, this being R for C12 and S for C22. It has not yet been possible to obtain crystals for X-ray diffraction of a single diastereomer.

S2. Experimental

0.95 g (2.29 mmol) of 2-hydroxymethyl-2-methyl-3-(toluene-4-sulfonyloxy)propyl 4-chlorobenzoate was dissolved in 50 ml of dichloromethane and treated with 0.86 g (3.44 mmol) of camphorsulfonic acid chloride in 35 ml of dichloromethane and 5 ml of triethylamine. After stirring overnight at room temperature, the reaction mixture was washed with 60 ml of 10% NaHCO₃ solution and 60 ml of water, and dried with Na₂SO₄. The crude product was purified by column chromatography (2:1 cyclohexane/ethyl acetate) to yield 1.12 g (1.78 mmol, 78%) of the title compound. The colourless oil was crystallized from petroleum ether (65–90)/MTBE (2:1) to give a colourless solid (m.p. 346–348 K). Treatment with methanol/hexane (1:4) gave crystals after four weeks suitable for X-ray diffraction; m.p. 347–349 K.

S3. Refinement

H atoms were placed in calculated positions with U_iso constrained to be 1.5 times U_eq of the carrier atom for the methyl-H and 1.2 times U_eq for the remaining H atoms.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

Figures

Fig. 1. View of the title compound showing the labelling of all non-H atoms. Displacement ellipsoids are shown at the 30% probability level. H atoms have been omitted.

(I)

Crystal data

C29H35ClO9S2	Z = 2
Mr = 627.14	F(000) = 660
Triclinic, P1	Dx = 1.357 Mg m^−3
a = 8.5321 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0941 (4) Å	Cell parameters from 15324 reflections
c = 16.6243 (6) Å	θ = 3.3–27.5°
α = 70.7225 (14)°	µ = 0.31 mm^−1
β = 85.0894 (14)°	T = 291 K
γ = 71.5179 (14)°	Block, colourless
V = 1535.38 (9) Å^3	0.6 × 0.4 × 0.35 mm

Data collection

Nonius KappaCCD diffractometer	5566 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 27.5°, θmin = 3.3°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −10→11
323 frames via ω–rotation (Δω=1°) with 3 sets at different κ–angles and two times 10 s per frame scans	k = −15→15
15324 measured reflections	l = −17→21
10443 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0209P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.84	(Δ/σ)max = 0.001
10443 reflections	Δρmax = 0.15 e Å^−3
747 parameters	Δρmin = −0.22 e Å^−3
3 restraints	Absolute structure: Flack (1983); 3632 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (4)

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
Cl11	0.59265 (14)	1.02472 (12)	−0.42133 (7)	0.0975 (4)
Cl21	0.1042 (2)	0.36583 (15)	0.66811 (8)	0.1360 (6)
S11	0.52469 (10)	0.97463 (10)	0.34109 (6)	0.0615 (3)
S12	0.22971 (10)	0.89733 (9)	0.11206 (6)	0.0567 (3)
S21	0.23458 (12)	0.34549 (10)	−0.08986 (6)	0.0658 (3)
S22	0.57190 (10)	0.46912 (10)	0.13108 (6)	0.0609 (3)
O11	0.7248 (3)	0.8994 (2)	−0.00957 (15)	0.0647 (7)
O12	0.9164 (3)	0.7337 (3)	−0.02537 (17)	0.0893 (9)
O13	0.5788 (3)	1.0066 (2)	0.24544 (14)	0.0572 (6)
O14	0.4672 (3)	1.0909 (3)	0.35471 (18)	0.0873 (9)
O15	0.6544 (3)	0.8776 (3)	0.39350 (15)	0.0810 (8)
O16	0.4587 (3)	0.6978 (3)	0.48851 (18)	0.0887 (9)
O17	0.4178 (2)	0.8813 (2)	0.12512 (14)	0.0529 (6)
O18	0.1318 (2)	0.9993 (2)	0.13758 (15)	0.0673 (7)
O19	0.2140 (3)	0.7784 (2)	0.15475 (16)	0.0742 (8)
O21	0.0642 (3)	0.4601 (2)	0.25177 (16)	0.0639 (7)
O22	−0.1322 (3)	0.6303 (3)	0.25677 (18)	0.0852 (9)
O23	0.2589 (3)	0.3556 (2)	0.00014 (14)	0.0589 (6)
O24	0.0650 (3)	0.3514 (3)	−0.09825 (16)	0.0851 (8)
O25	0.3628 (3)	0.2382 (2)	−0.09393 (17)	0.0761 (7)
O26	0.2462 (4)	0.7137 (3)	−0.26179 (17)	0.0905 (9)
O27	0.3858 (2)	0.4809 (2)	0.11710 (14)	0.0543 (6)
O28	0.6765 (3)	0.3647 (2)	0.11039 (16)	0.0743 (8)
O29	0.5832 (3)	0.5889 (2)	0.08473 (16)	0.0770 (8)
C11	0.7561 (4)	0.8543 (3)	0.0818 (2)	0.0578 (10)
H11A	0.8725	0.8355	0.0941	0.069*
H11B	0.7243	0.7802	0.1078	0.069*
C12	0.6524 (3)	0.9566 (3)	0.1161 (2)	0.0450 (9)
C13	0.6767 (4)	0.9063 (3)	0.2123 (2)	0.0514 (9)
H13A	0.6382	0.8348	0.2357	0.062*
H13B	0.7926	0.8824	0.2276	0.062*
C14	0.4706 (4)	0.9916 (3)	0.0913 (2)	0.0488 (9)
H14A	0.4041	1.0548	0.1147	0.059*
H14B	0.4567	1.0235	0.0297	0.059*
C15	0.7051 (4)	1.0723 (3)	0.0775 (2)	0.0648 (11)
H15A	0.6383	1.1356	0.0998	0.097*
H15B	0.6910	1.1001	0.0167	0.097*
H15C	0.8192	1.0540	0.0919	0.097*
C16	0.8097 (4)	0.8289 (4)	−0.0551 (3)	0.0611 (10)
C17	0.7569 (4)	0.8840 (3)	−0.1465 (2)	0.0560 (10)
C18	0.8396 (4)	0.8259 (4)	−0.2037 (3)	0.0704 (11)
H18	0.9302	0.7559	−0.1847	0.085*
C19	0.7914 (5)	0.8688 (4)	−0.2876 (3)	0.0699 (11)
H19	0.8473	0.8276	−0.3249	0.084*
C110	0.6621 (5)	0.9716 (4)	−0.3155 (2)	0.0665 (11)
C111	0.5766 (5)	1.0346 (4)	−0.2617 (3)	0.0816 (13)
H111	0.4883	1.1059	−0.2821	0.098*
C112	0.6257 (5)	0.9890 (4)	−0.1759 (3)	0.0756 (12)
H112	0.5692	1.0299	−0.1384	0.091*
C113	0.3557 (3)	0.9222 (3)	0.3369 (2)	0.0488 (8)
H11C	0.2813	0.9833	0.2911	0.059*
H11D	0.3970	0.8474	0.3216	0.059*
C114	0.2550 (4)	0.8958 (3)	0.4178 (2)	0.0489 (9)
C115	0.3202 (5)	0.7686 (4)	0.4814 (2)	0.0664 (10)
C116	0.1735 (5)	0.7450 (4)	0.5360 (2)	0.0828 (12)
H11E	0.1501	0.6733	0.5324	0.099*
H11F	0.1927	0.7339	0.5953	0.099*
C117	0.0339 (4)	0.8628 (4)	0.4956 (2)	0.0681 (11)
H117	−0.0773	0.8551	0.5073	0.082*
C118	0.0644 (4)	0.9627 (4)	0.5217 (2)	0.0855 (13)
H11G	0.0860	0.9360	0.5826	0.103*
H11H	−0.0295	1.0371	0.5064	0.103*
C119	0.2196 (4)	0.9842 (4)	0.4705 (2)	0.0659 (10)
H11I	0.1965	1.0690	0.4338	0.079*
H11J	0.3121	0.9641	0.5084	0.079*
C120	0.0785 (3)	0.8953 (3)	0.4006 (2)	0.0522 (9)
C121	0.0782 (4)	0.7973 (3)	0.3606 (2)	0.0613 (10)
H12A	0.1142	0.8202	0.3028	0.092*
H12B	−0.0316	0.7916	0.3613	0.092*
H12C	0.1518	0.7191	0.3927	0.092*
C122	−0.0315 (4)	1.0197 (3)	0.3448 (2)	0.0680 (11)
H12D	−0.0116	1.0845	0.3595	0.102*
H12E	−0.1455	1.0234	0.3539	0.102*
H12F	−0.0066	1.0292	0.2859	0.102*
C123	0.2037 (4)	0.9342 (3)	0.0024 (2)	0.0513 (9)
C124	0.2720 (7)	0.8468 (4)	−0.0350 (3)	0.1137 (19)
H124	0.3340	0.7682	−0.0027	0.136*
C125	0.2491 (8)	0.8746 (5)	−0.1210 (3)	0.133 (2)
H125	0.2962	0.8135	−0.1459	0.159*
C126	0.1601 (5)	0.9884 (4)	−0.1712 (3)	0.0723 (12)
C127	0.0966 (5)	1.0741 (4)	−0.1327 (3)	0.0776 (12)
H127	0.0365	1.1531	−0.1654	0.093*
C128	0.1172 (4)	1.0495 (4)	−0.0458 (3)	0.0683 (11)
H128	0.0723	1.1110	−0.0211	0.082*
C129	0.1343 (6)	1.0188 (4)	−0.2658 (3)	0.1115 (18)
H12G	0.0591	1.1004	−0.2883	0.167*
H12H	0.0891	0.9609	−0.2755	0.167*
H12I	0.2382	1.0144	−0.2938	0.167*
C21	0.0465 (4)	0.5033 (4)	0.1599 (2)	0.0587 (10)
H21A	0.0804	0.5767	0.1357	0.070*
H21B	−0.0676	0.5224	0.1430	0.070*
C22	0.1581 (4)	0.3984 (3)	0.1298 (2)	0.0478 (9)
C23	0.1350 (4)	0.4443 (3)	0.0328 (2)	0.0589 (10)
H23A	0.0247	0.4502	0.0176	0.071*
H23B	0.1498	0.5251	0.0090	0.071*
C24	0.3359 (4)	0.3704 (3)	0.1547 (2)	0.0533 (9)
H24A	0.3477	0.3437	0.2163	0.064*
H24B	0.4059	0.3047	0.1345	0.064*
C25	0.1088 (4)	0.2812 (3)	0.1671 (2)	0.0681 (11)
H25A	0.1740	0.2204	0.1423	0.102*
H25B	−0.0061	0.2990	0.1548	0.102*
H25C	0.1275	0.2504	0.2277	0.102*
C26	−0.0314 (5)	0.5343 (4)	0.2930 (3)	0.0577 (10)
C27	0.0029 (5)	0.4873 (4)	0.3860 (3)	0.0578 (10)
C28	−0.0963 (5)	0.5523 (4)	0.4356 (3)	0.0660 (11)
H28	−0.1835	0.6221	0.4102	0.079*
C29	−0.0684 (6)	0.5158 (5)	0.5224 (3)	0.0821 (13)
H29	−0.1362	0.5598	0.5555	0.098*
C210	0.0599 (7)	0.4143 (6)	0.5582 (3)	0.0863 (14)
C211	0.1606 (5)	0.3452 (4)	0.5106 (3)	0.0943 (15)
H211	0.2471	0.2751	0.5365	0.113*
C212	0.1293 (5)	0.3829 (4)	0.4238 (3)	0.0776 (12)
H212	0.1945	0.3373	0.3910	0.093*
C213	0.2585 (4)	0.4777 (3)	−0.1658 (2)	0.0697 (11)
H21C	0.2375	0.4735	−0.2210	0.084*
H21D	0.1705	0.5466	−0.1574	0.084*
C214	0.4209 (4)	0.5120 (3)	−0.1732 (2)	0.0572 (9)
C215	0.3822 (6)	0.6415 (4)	−0.2396 (2)	0.0708 (11)
C216	0.5440 (6)	0.6608 (4)	−0.2679 (3)	0.0970 (14)
H21E	0.5539	0.7328	−0.2577	0.116*
H21F	0.5597	0.6699	−0.3280	0.116*
C217	0.6685 (5)	0.5417 (4)	−0.2118 (3)	0.0857 (12)
H217	0.7818	0.5243	−0.2327	0.103*
C218	0.6514 (5)	0.5467 (4)	−0.1198 (3)	0.0913 (14)
H21G	0.6546	0.6253	−0.1180	0.110*
H21H	0.7384	0.4813	−0.0827	0.110*
C219	0.4783 (4)	0.5290 (4)	−0.0939 (2)	0.0762 (11)
H21I	0.4873	0.4570	−0.0441	0.091*
H21J	0.4029	0.6007	−0.0821	0.091*
C220	0.5816 (4)	0.4441 (4)	−0.2079 (3)	0.0725 (11)
C221	0.5595 (5)	0.4306 (4)	−0.2949 (3)	0.1047 (15)
H22A	0.4911	0.3789	−0.2886	0.157*
H22B	0.6656	0.3944	−0.3153	0.157*
H22C	0.5081	0.5103	−0.3348	0.157*
C222	0.6776 (4)	0.3176 (4)	−0.1477 (3)	0.1019 (15)
H22D	0.6227	0.2587	−0.1458	0.153*
H22E	0.6827	0.3224	−0.0916	0.153*
H22F	0.7877	0.2923	−0.1681	0.153*
C223	0.5862 (4)	0.4412 (4)	0.2407 (2)	0.0533 (9)
C224	0.5269 (5)	0.5355 (4)	0.2737 (3)	0.0821 (13)
H224	0.4822	0.6158	0.2378	0.099*
C225	0.5336 (6)	0.5113 (4)	0.3604 (3)	0.0921 (14)
H225	0.4916	0.5759	0.3826	0.111*
C226	0.6000 (5)	0.3955 (5)	0.4145 (3)	0.0700 (12)
C227	0.6571 (5)	0.3030 (4)	0.3808 (3)	0.0830 (13)
H227	0.7009	0.2228	0.4170	0.100*
C228	0.6523 (5)	0.3243 (4)	0.2940 (3)	0.0768 (12)
H228	0.6938	0.2593	0.2722	0.092*
C229	0.6074 (6)	0.3717 (5)	0.5113 (3)	0.1041 (15)
H22G	0.5191	0.4334	0.5263	0.156*
H22H	0.7114	0.3749	0.5265	0.156*
H22I	0.5961	0.2919	0.5413	0.156*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl11	0.1092 (8)	0.1286 (10)	0.0538 (7)	−0.0434 (7)	−0.0084 (6)	−0.0190 (7)
Cl21	0.1985 (14)	0.1704 (15)	0.0563 (8)	−0.0892 (12)	−0.0102 (8)	−0.0243 (9)
S11	0.0512 (5)	0.0886 (8)	0.0612 (7)	−0.0299 (5)	0.0095 (5)	−0.0392 (6)
S12	0.0511 (6)	0.0707 (8)	0.0503 (6)	−0.0202 (6)	−0.0021 (5)	−0.0198 (6)
S21	0.0642 (6)	0.0735 (7)	0.0599 (7)	−0.0142 (5)	−0.0007 (5)	−0.0278 (6)
S22	0.0526 (6)	0.0755 (8)	0.0544 (7)	−0.0212 (6)	−0.0037 (5)	−0.0178 (6)
O11	0.0695 (15)	0.0659 (17)	0.0421 (17)	0.0051 (13)	0.0023 (12)	−0.0211 (14)
O12	0.094 (2)	0.075 (2)	0.0619 (19)	0.0191 (17)	−0.0027 (15)	−0.0168 (16)
O13	0.0534 (13)	0.0694 (16)	0.0554 (16)	−0.0229 (12)	0.0075 (11)	−0.0262 (13)
O14	0.0976 (19)	0.106 (2)	0.103 (2)	−0.0580 (18)	0.0441 (16)	−0.0744 (19)
O15	0.0464 (13)	0.137 (2)	0.0554 (16)	−0.0254 (15)	−0.0087 (12)	−0.0258 (16)
O16	0.0731 (18)	0.085 (2)	0.091 (2)	−0.0105 (16)	−0.0178 (16)	−0.0151 (17)
O17	0.0494 (13)	0.0539 (15)	0.0543 (16)	−0.0162 (12)	−0.0058 (11)	−0.0140 (12)
O18	0.0480 (14)	0.094 (2)	0.0610 (18)	−0.0102 (14)	0.0030 (12)	−0.0375 (16)
O19	0.0822 (17)	0.077 (2)	0.0687 (19)	−0.0439 (15)	−0.0039 (13)	−0.0102 (16)
O21	0.0603 (15)	0.0639 (17)	0.0531 (19)	0.0002 (13)	−0.0053 (13)	−0.0169 (15)
O22	0.0936 (19)	0.068 (2)	0.0665 (19)	0.0122 (17)	0.0018 (16)	−0.0224 (16)
O23	0.0560 (13)	0.0677 (16)	0.0495 (15)	−0.0076 (12)	−0.0024 (11)	−0.0243 (13)
O24	0.0640 (16)	0.116 (2)	0.093 (2)	−0.0317 (15)	−0.0041 (13)	−0.0515 (17)
O25	0.0782 (16)	0.0587 (16)	0.091 (2)	−0.0095 (14)	0.0127 (14)	−0.0368 (14)
O26	0.117 (2)	0.0723 (19)	0.0674 (19)	−0.0066 (18)	−0.0141 (17)	−0.0211 (15)
O27	0.0458 (13)	0.0554 (16)	0.0590 (16)	−0.0153 (12)	−0.0077 (11)	−0.0129 (13)
O28	0.0530 (14)	0.097 (2)	0.072 (2)	−0.0079 (15)	−0.0001 (13)	−0.0403 (17)
O29	0.0868 (18)	0.082 (2)	0.0634 (18)	−0.0477 (16)	−0.0043 (13)	−0.0027 (16)
C11	0.056 (2)	0.064 (3)	0.040 (3)	−0.007 (2)	−0.0044 (18)	−0.010 (2)
C12	0.0330 (18)	0.050 (2)	0.048 (2)	−0.0082 (17)	−0.0058 (15)	−0.0143 (19)
C13	0.0324 (17)	0.058 (2)	0.062 (3)	−0.0040 (17)	0.0025 (16)	−0.027 (2)
C14	0.0414 (18)	0.042 (2)	0.061 (3)	−0.0066 (17)	−0.0065 (17)	−0.0170 (19)
C15	0.052 (2)	0.073 (3)	0.069 (3)	−0.018 (2)	0.0010 (18)	−0.023 (2)
C16	0.054 (2)	0.061 (3)	0.059 (3)	−0.006 (2)	0.005 (2)	−0.019 (2)
C17	0.056 (2)	0.056 (2)	0.050 (3)	−0.011 (2)	0.0062 (19)	−0.016 (2)
C18	0.062 (2)	0.071 (3)	0.060 (3)	−0.001 (2)	0.002 (2)	−0.015 (2)
C19	0.078 (3)	0.082 (3)	0.050 (3)	−0.022 (3)	0.012 (2)	−0.026 (2)
C110	0.078 (3)	0.082 (3)	0.048 (3)	−0.034 (3)	−0.004 (2)	−0.021 (2)
C111	0.081 (3)	0.084 (3)	0.061 (3)	0.002 (2)	−0.018 (2)	−0.020 (3)
C112	0.081 (3)	0.069 (3)	0.061 (3)	0.006 (2)	−0.004 (2)	−0.027 (2)
C113	0.0419 (18)	0.054 (2)	0.052 (2)	−0.0146 (16)	−0.0044 (15)	−0.0182 (17)
C114	0.0395 (18)	0.060 (2)	0.050 (2)	−0.0142 (17)	−0.0004 (16)	−0.0219 (19)
C115	0.065 (3)	0.077 (3)	0.059 (3)	−0.026 (2)	−0.018 (2)	−0.016 (2)
C116	0.094 (3)	0.108 (4)	0.042 (2)	−0.046 (3)	−0.002 (2)	−0.002 (2)
C117	0.056 (2)	0.099 (3)	0.060 (3)	−0.036 (2)	0.0136 (19)	−0.031 (2)
C118	0.074 (2)	0.137 (4)	0.074 (3)	−0.045 (3)	0.026 (2)	−0.064 (3)
C119	0.055 (2)	0.092 (3)	0.066 (3)	−0.026 (2)	0.0119 (18)	−0.045 (2)
C120	0.0464 (19)	0.059 (2)	0.051 (2)	−0.0202 (18)	−0.0021 (16)	−0.0134 (19)
C121	0.065 (2)	0.072 (3)	0.056 (2)	−0.034 (2)	−0.0009 (17)	−0.021 (2)
C122	0.0400 (19)	0.076 (3)	0.080 (3)	−0.0143 (18)	−0.0030 (18)	−0.017 (2)
C123	0.057 (2)	0.049 (2)	0.049 (2)	−0.0148 (19)	−0.0096 (18)	−0.017 (2)
C124	0.200 (5)	0.058 (3)	0.070 (4)	−0.009 (3)	−0.048 (3)	−0.020 (3)
C125	0.251 (7)	0.069 (4)	0.070 (4)	−0.016 (4)	−0.032 (4)	−0.036 (3)
C126	0.105 (3)	0.066 (3)	0.054 (3)	−0.032 (3)	−0.021 (2)	−0.019 (3)
C127	0.070 (3)	0.076 (3)	0.065 (3)	−0.002 (2)	−0.011 (2)	−0.013 (3)
C128	0.072 (2)	0.062 (3)	0.064 (3)	−0.006 (2)	−0.002 (2)	−0.025 (2)
C129	0.187 (5)	0.096 (4)	0.066 (4)	−0.056 (4)	−0.024 (3)	−0.027 (3)
C21	0.048 (2)	0.072 (3)	0.045 (3)	−0.009 (2)	−0.0019 (17)	−0.013 (2)
C22	0.0378 (18)	0.050 (2)	0.050 (2)	−0.0052 (17)	0.0011 (16)	−0.0169 (19)
C23	0.052 (2)	0.063 (3)	0.060 (3)	−0.0057 (19)	0.0020 (18)	−0.029 (2)
C24	0.055 (2)	0.052 (2)	0.048 (2)	−0.0126 (19)	−0.0036 (17)	−0.0132 (19)
C25	0.071 (2)	0.058 (3)	0.070 (3)	−0.019 (2)	0.006 (2)	−0.017 (2)
C26	0.064 (2)	0.057 (3)	0.056 (3)	−0.023 (2)	0.004 (2)	−0.019 (2)
C27	0.067 (2)	0.050 (2)	0.052 (3)	−0.016 (2)	−0.001 (2)	−0.013 (2)
C28	0.081 (3)	0.066 (3)	0.051 (3)	−0.023 (2)	0.006 (2)	−0.019 (2)
C29	0.102 (3)	0.089 (4)	0.072 (4)	−0.050 (3)	0.020 (3)	−0.031 (3)
C210	0.116 (4)	0.114 (4)	0.045 (3)	−0.062 (3)	0.006 (3)	−0.021 (3)
C211	0.096 (3)	0.092 (4)	0.074 (4)	−0.022 (3)	−0.012 (3)	−0.003 (3)
C212	0.090 (3)	0.081 (3)	0.053 (3)	−0.017 (3)	0.000 (2)	−0.017 (2)
C213	0.077 (2)	0.059 (2)	0.059 (2)	0.005 (2)	−0.0253 (19)	−0.018 (2)
C214	0.070 (2)	0.056 (2)	0.050 (2)	−0.0191 (19)	−0.0036 (18)	−0.0209 (19)
C215	0.090 (3)	0.072 (3)	0.049 (3)	−0.023 (3)	−0.006 (2)	−0.016 (2)
C216	0.136 (4)	0.088 (3)	0.067 (3)	−0.051 (3)	0.010 (3)	−0.011 (3)
C217	0.077 (3)	0.092 (3)	0.087 (3)	−0.033 (3)	0.011 (2)	−0.023 (3)
C218	0.091 (3)	0.121 (4)	0.074 (3)	−0.054 (3)	−0.006 (2)	−0.025 (3)
C219	0.076 (3)	0.091 (3)	0.057 (3)	−0.019 (2)	−0.009 (2)	−0.021 (2)
C220	0.063 (2)	0.064 (3)	0.079 (3)	−0.009 (2)	−0.001 (2)	−0.019 (2)
C221	0.113 (3)	0.125 (4)	0.082 (3)	−0.022 (3)	0.017 (3)	−0.059 (3)
C222	0.062 (3)	0.083 (3)	0.129 (4)	−0.001 (2)	−0.007 (2)	−0.011 (3)
C223	0.050 (2)	0.059 (3)	0.047 (2)	−0.0117 (19)	−0.0065 (17)	−0.015 (2)
C224	0.118 (3)	0.058 (3)	0.061 (3)	−0.006 (2)	−0.015 (2)	−0.021 (2)
C225	0.140 (4)	0.066 (3)	0.067 (4)	−0.011 (3)	−0.009 (3)	−0.035 (3)
C226	0.078 (3)	0.081 (3)	0.058 (3)	−0.030 (3)	−0.003 (2)	−0.025 (3)
C227	0.104 (3)	0.064 (3)	0.058 (3)	−0.008 (3)	−0.013 (2)	−0.004 (2)
C228	0.097 (3)	0.063 (3)	0.055 (3)	0.003 (2)	−0.011 (2)	−0.023 (2)
C229	0.139 (4)	0.132 (4)	0.054 (3)	−0.065 (3)	0.003 (3)	−0.024 (3)

Geometric parameters (Å, º)

Cl11—C110	1.747 (4)	C122—H12F	0.960
Cl21—C210	1.759 (5)	C123—C124	1.351 (5)
S11—O14	1.422 (3)	C123—C128	1.357 (5)
S11—O15	1.424 (2)	C124—C125	1.372 (6)
S11—O13	1.572 (2)	C124—H124	0.930
S11—C113	1.764 (3)	C125—C126	1.363 (6)
S12—O19	1.423 (3)	C125—H125	0.930
S12—O18	1.425 (2)	C126—C127	1.342 (5)
S12—O17	1.579 (2)	C126—C129	1.511 (5)
S12—C123	1.744 (4)	C127—C128	1.389 (5)
S21—O25	1.425 (2)	C127—H127	0.930
S21—O24	1.442 (2)	C128—H128	0.930
S21—O23	1.577 (2)	C129—H12G	0.960
S21—C213	1.738 (4)	C129—H12H	0.960
S22—O28	1.424 (3)	C129—H12I	0.960
S22—O29	1.428 (3)	C21—C22	1.529 (4)
S22—O27	1.579 (2)	C21—H21A	0.970
S22—C223	1.748 (4)	C21—H21B	0.970
O11—C16	1.329 (4)	C22—C24	1.508 (4)
O11—C11	1.452 (4)	C22—C25	1.524 (5)
O12—C16	1.198 (4)	C22—C23	1.530 (4)
O13—C13	1.481 (4)	C23—H23A	0.970
O16—C115	1.208 (4)	C23—H23B	0.970
O17—C14	1.463 (4)	C24—H24A	0.970
O21—C26	1.336 (4)	C24—H24B	0.970
O21—C21	1.446 (4)	C25—H25A	0.960
O22—C26	1.202 (4)	C25—H25B	0.960
O23—C23	1.460 (4)	C25—H25C	0.960
O26—C215	1.210 (4)	C26—C27	1.480 (5)
O27—C24	1.456 (4)	C27—C212	1.372 (5)
C11—C12	1.525 (4)	C27—C28	1.380 (5)
C11—H11A	0.970	C28—C29	1.379 (6)
C11—H11B	0.970	C28—H28	0.930
C12—C13	1.517 (5)	C29—C210	1.356 (6)
C12—C15	1.526 (4)	C29—H29	0.930
C12—C14	1.528 (4)	C210—C211	1.388 (6)
C13—H13A	0.970	C211—C212	1.384 (5)
C13—H13B	0.970	C211—H211	0.930
C14—H14A	0.970	C212—H212	0.930
C14—H14B	0.970	C213—C214	1.552 (5)
C15—H15A	0.960	C213—H21C	0.970
C15—H15B	0.960	C213—H21D	0.970
C15—H15C	0.960	C214—C220	1.534 (5)
C16—C17	1.487 (5)	C214—C219	1.540 (4)
C17—C112	1.374 (5)	C214—C215	1.541 (5)
C17—C18	1.382 (5)	C215—C216	1.484 (5)
C18—C19	1.366 (5)	C216—C217	1.545 (6)
C18—H18	0.930	C216—H21E	0.970
C19—C110	1.348 (5)	C216—H21F	0.970
C19—H19	0.930	C217—C218	1.544 (5)
C110—C111	1.377 (5)	C217—C220	1.564 (5)
C111—C112	1.398 (5)	C217—H217	0.980
C111—H111	0.930	C218—C219	1.563 (5)
C112—H112	0.930	C218—H21G	0.970
C113—C114	1.530 (4)	C218—H21H	0.970
C113—H11C	0.970	C219—H21I	0.970
C113—H11D	0.970	C219—H21J	0.970
C114—C115	1.510 (5)	C220—C222	1.532 (5)
C114—C119	1.540 (4)	C220—C221	1.541 (5)
C114—C120	1.559 (4)	C221—H22A	0.960
C115—C116	1.528 (5)	C221—H22B	0.960
C116—C117	1.526 (5)	C221—H22C	0.960
C116—H11E	0.970	C222—H22D	0.960
C116—H11F	0.970	C222—H22E	0.960
C117—C118	1.510 (5)	C222—H22F	0.960
C117—C120	1.541 (4)	C223—C228	1.363 (5)
C117—H117	0.980	C223—C224	1.363 (5)
C118—C119	1.558 (5)	C224—C225	1.376 (6)
C118—H11G	0.970	C224—H224	0.930
C118—H11H	0.970	C225—C226	1.358 (5)
C119—H11I	0.970	C225—H225	0.930
C119—H11J	0.970	C226—C227	1.351 (5)
C120—C122	1.529 (4)	C226—C229	1.541 (5)
C120—C121	1.539 (4)	C227—C228	1.381 (5)
C121—H12A	0.960	C227—H227	0.930
C121—H12B	0.960	C228—H228	0.930
C121—H12C	0.960	C229—H22G	0.960
C122—H12D	0.960	C229—H22H	0.960
C122—H12E	0.960	C229—H22I	0.960
O14—S11—O15	120.20 (17)	C127—C126—C125	116.6 (4)
O14—S11—O13	103.74 (16)	C127—C126—C129	120.9 (4)
O15—S11—O13	109.66 (14)	C125—C126—C129	122.4 (4)
O14—S11—C113	109.79 (15)	C126—C127—C128	122.6 (4)
O15—S11—C113	110.21 (15)	C126—C127—H127	118.7
O13—S11—C113	101.44 (13)	C128—C127—H127	118.7
O19—S12—O18	119.59 (16)	C123—C128—C127	119.1 (4)
O19—S12—O17	104.41 (14)	C123—C128—H128	120.5
O18—S12—O17	108.27 (13)	C127—C128—H128	120.5
O19—S12—C123	109.93 (17)	C126—C129—H12G	109.5
O18—S12—C123	108.78 (17)	C126—C129—H12H	109.5
O17—S12—C123	104.79 (14)	H12G—C129—H12H	109.5
O25—S21—O24	118.87 (16)	C126—C129—H12I	109.5
O25—S21—O23	104.98 (14)	H12G—C129—H12I	109.5
O24—S21—O23	108.19 (14)	H12H—C129—H12I	109.5
O25—S21—C213	111.55 (16)	O21—C21—C22	106.0 (3)
O24—S21—C213	105.82 (17)	O21—C21—H21A	110.5
O23—S21—C213	106.87 (16)	C22—C21—H21A	110.5
O28—S22—O29	119.83 (16)	O21—C21—H21B	110.5
O28—S22—O27	108.97 (14)	C22—C21—H21B	110.5
O29—S22—O27	103.77 (14)	H21A—C21—H21B	108.7
O28—S22—C223	109.27 (17)	C24—C22—C25	108.7 (3)
O29—S22—C223	110.43 (18)	C24—C22—C21	110.5 (3)
O27—S22—C223	103.17 (14)	C25—C22—C21	112.0 (3)
C16—O11—C11	117.9 (3)	C24—C22—C23	111.0 (3)
C13—O13—S11	119.6 (2)	C25—C22—C23	109.3 (3)
C14—O17—S12	117.16 (17)	C21—C22—C23	105.4 (3)
C26—O21—C21	116.7 (3)	O23—C23—C22	107.2 (3)
C23—O23—S21	120.9 (2)	O23—C23—H23A	110.3
C24—O27—S22	117.16 (18)	C22—C23—H23A	110.3
O11—C11—C12	106.5 (3)	O23—C23—H23B	110.3
O11—C11—H11A	110.4	C22—C23—H23B	110.3
C12—C11—H11A	110.4	H23A—C23—H23B	108.5
O11—C11—H11B	110.4	O27—C24—C22	109.1 (3)
C12—C11—H11B	110.4	O27—C24—H24A	109.9
H11A—C11—H11B	108.6	C22—C24—H24A	109.9
C13—C12—C11	106.4 (3)	O27—C24—H24B	109.9
C13—C12—C15	111.8 (3)	C22—C24—H24B	109.9
C11—C12—C15	110.8 (3)	H24A—C24—H24B	108.3
C13—C12—C14	110.9 (3)	C22—C25—H25A	109.5
C11—C12—C14	110.1 (3)	C22—C25—H25B	109.5
C15—C12—C14	106.9 (3)	H25A—C25—H25B	109.5
O13—C13—C12	106.4 (3)	C22—C25—H25C	109.5
O13—C13—H13A	110.4	H25A—C25—H25C	109.5
C12—C13—H13A	110.4	H25B—C25—H25C	109.5
O13—C13—H13B	110.4	O22—C26—O21	122.4 (4)
C12—C13—H13B	110.4	O22—C26—C27	124.3 (4)
H13A—C13—H13B	108.6	O21—C26—C27	113.2 (4)
O17—C14—C12	108.2 (2)	C212—C27—C28	119.4 (4)
O17—C14—H14A	110.1	C212—C27—C26	122.5 (4)
C12—C14—H14A	110.1	C28—C27—C26	118.1 (4)
O17—C14—H14B	110.1	C29—C28—C27	121.2 (4)
C12—C14—H14B	110.1	C29—C28—H28	119.4
H14A—C14—H14B	108.4	C27—C28—H28	119.4
C12—C15—H15A	109.5	C210—C29—C28	118.5 (4)
C12—C15—H15B	109.5	C210—C29—H29	120.7
H15A—C15—H15B	109.5	C28—C29—H29	120.7
C12—C15—H15C	109.5	C29—C210—C211	122.0 (4)
H15A—C15—H15C	109.5	C29—C210—Cl21	120.4 (4)
H15B—C15—H15C	109.5	C211—C210—Cl21	117.7 (5)
O12—C16—O11	123.4 (4)	C212—C211—C210	118.5 (4)
O12—C16—C17	125.0 (4)	C212—C211—H211	120.7
O11—C16—C17	111.6 (3)	C210—C211—H211	120.7
C112—C17—C18	118.5 (4)	C27—C212—C211	120.4 (4)
C112—C17—C16	122.4 (4)	C27—C212—H212	119.8
C18—C17—C16	119.0 (3)	C211—C212—H212	119.8
C19—C18—C17	121.6 (4)	C214—C213—S21	122.3 (2)
C19—C18—H18	119.2	C214—C213—H21C	106.8
C17—C18—H18	119.2	S21—C213—H21C	106.8
C110—C19—C18	119.2 (4)	C214—C213—H21D	106.8
C110—C19—H19	120.4	S21—C213—H21D	106.8
C18—C19—H19	120.4	H21C—C213—H21D	106.6
C19—C110—C111	121.8 (4)	C220—C214—C219	103.8 (3)
C19—C110—Cl11	120.1 (3)	C220—C214—C215	100.9 (3)
C111—C110—Cl11	118.1 (3)	C219—C214—C215	103.4 (3)
C110—C111—C112	118.5 (4)	C220—C214—C213	123.6 (3)
C110—C111—H111	120.8	C219—C214—C213	116.9 (3)
C112—C111—H111	120.8	C215—C214—C213	105.3 (3)
C17—C112—C111	120.4 (4)	O26—C215—C216	127.4 (4)
C17—C112—H112	119.8	O26—C215—C214	126.2 (4)
C111—C112—H112	119.8	C216—C215—C214	106.4 (4)
C114—C113—S11	117.1 (2)	C215—C216—C217	102.7 (4)
C114—C113—H11C	108.0	C215—C216—H21E	111.2
S11—C113—H11C	108.0	C217—C216—H21E	111.2
C114—C113—H11D	108.0	C215—C216—H21F	111.2
S11—C113—H11D	108.0	C217—C216—H21F	111.2
H11C—C113—H11D	107.3	H21E—C216—H21F	109.1
C115—C114—C113	115.4 (3)	C218—C217—C216	106.8 (4)
C115—C114—C119	105.2 (3)	C218—C217—C220	102.3 (3)
C113—C114—C119	118.4 (3)	C216—C217—C220	101.1 (3)
C115—C114—C120	99.9 (3)	C218—C217—H217	115.0
C113—C114—C120	113.2 (3)	C216—C217—H217	115.0
C119—C114—C120	102.5 (2)	C220—C217—H217	115.0
O16—C115—C114	128.1 (3)	C217—C218—C219	103.0 (3)
O16—C115—C116	126.0 (4)	C217—C218—H21G	111.2
C114—C115—C116	105.9 (3)	C219—C218—H21G	111.2
C117—C116—C115	102.0 (3)	C217—C218—H21H	111.2
C117—C116—H11E	111.4	C219—C218—H21H	111.2
C115—C116—H11E	111.4	H21G—C218—H21H	109.1
C117—C116—H11F	111.4	C214—C219—C218	103.0 (3)
C115—C116—H11F	111.4	C214—C219—H21I	111.2
H11E—C116—H11F	109.2	C218—C219—H21I	111.2
C118—C117—C116	106.7 (3)	C214—C219—H21J	111.2
C118—C117—C120	103.2 (3)	C218—C219—H21J	111.2
C116—C117—C120	102.3 (3)	H21I—C219—H21J	109.1
C118—C117—H117	114.5	C222—C220—C214	115.8 (3)
C116—C117—H117	114.5	C222—C220—C221	108.4 (4)
C120—C117—H117	114.5	C214—C220—C221	113.8 (3)
C117—C118—C119	103.4 (3)	C222—C220—C217	110.4 (3)
C117—C118—H11G	111.1	C214—C220—C217	93.7 (3)
C119—C118—H11G	111.1	C221—C220—C217	114.4 (4)
C117—C118—H11H	111.1	C220—C221—H22A	109.5
C119—C118—H11H	111.1	C220—C221—H22B	109.5
H11G—C118—H11H	109.1	H22A—C221—H22B	109.5
C114—C119—C118	103.2 (3)	C220—C221—H22C	109.5
C114—C119—H11I	111.1	H22A—C221—H22C	109.5
C118—C119—H11I	111.1	H22B—C221—H22C	109.5
C114—C119—H11J	111.1	C220—C222—H22D	109.5
C118—C119—H11J	111.1	C220—C222—H22E	109.5
H11I—C119—H11J	109.1	H22D—C222—H22E	109.5
C122—C120—C121	107.9 (3)	C220—C222—H22F	109.5
C122—C120—C117	113.9 (3)	H22D—C222—H22F	109.5
C121—C120—C117	113.7 (3)	H22E—C222—H22F	109.5
C122—C120—C114	113.6 (3)	C228—C223—C224	119.5 (4)
C121—C120—C114	113.7 (3)	C228—C223—S22	120.1 (3)
C117—C120—C114	93.6 (2)	C224—C223—S22	120.3 (3)
C120—C121—H12A	109.5	C223—C224—C225	119.6 (4)
C120—C121—H12B	109.5	C223—C224—H224	120.2
H12A—C121—H12B	109.5	C225—C224—H224	120.2
C120—C121—H12C	109.5	C226—C225—C224	121.7 (4)
H12A—C121—H12C	109.5	C226—C225—H225	119.1
H12B—C121—H12C	109.5	C224—C225—H225	119.1
C120—C122—H12D	109.5	C227—C226—C225	117.9 (4)
C120—C122—H12E	109.5	C227—C226—C229	121.6 (4)
H12D—C122—H12E	109.5	C225—C226—C229	120.4 (5)
C120—C122—H12F	109.5	C226—C227—C228	121.7 (4)
H12D—C122—H12F	109.5	C226—C227—H227	119.1
H12E—C122—H12F	109.5	C228—C227—H227	119.1
C124—C123—C128	119.6 (4)	C223—C228—C227	119.5 (4)
C124—C123—S12	119.4 (3)	C223—C228—H228	120.2
C128—C123—S12	121.0 (3)	C227—C228—H228	120.2
C123—C124—C125	119.6 (4)	C226—C229—H22G	109.5
C123—C124—H124	120.2	C226—C229—H22H	109.5
C125—C124—H124	120.2	H22G—C229—H22H	109.5
C126—C125—C124	122.5 (5)	C226—C229—H22I	109.5
C126—C125—H125	118.8	H22G—C229—H22I	109.5
C124—C125—H125	118.8	H22H—C229—H22I	109.5
O14—S11—O13—C13	167.8 (2)	C124—C125—C126—C129	−179.7 (5)
O15—S11—O13—C13	38.2 (2)	C125—C126—C127—C128	−0.9 (7)
C113—S11—O13—C13	−78.3 (2)	C129—C126—C127—C128	179.7 (4)
O19—S12—O17—C14	−177.0 (2)	C124—C123—C128—C127	1.8 (6)
O18—S12—O17—C14	−48.6 (2)	S12—C123—C128—C127	−178.7 (3)
C123—S12—O17—C14	67.4 (3)	C126—C127—C128—C123	−0.5 (6)
O25—S21—O23—C23	−170.7 (2)	C26—O21—C21—C22	−175.7 (3)
O24—S21—O23—C23	−42.8 (3)	O21—C21—C22—C24	−61.3 (3)
C213—S21—O23—C23	70.7 (3)	O21—C21—C22—C25	59.9 (3)
O28—S22—O27—C24	49.1 (2)	O21—C21—C22—C23	178.7 (2)
O29—S22—O27—C24	177.8 (2)	S21—O23—C23—C22	158.1 (2)
C223—S22—O27—C24	−67.0 (3)	C24—C22—C23—O23	51.4 (4)
C16—O11—C11—C12	175.9 (3)	C25—C22—C23—O23	−68.5 (3)
O11—C11—C12—C13	176.5 (2)	C21—C22—C23—O23	171.0 (2)
O11—C11—C12—C15	−61.8 (3)	S22—O27—C24—C22	−176.6 (2)
O11—C11—C12—C14	56.3 (3)	C25—C22—C24—O27	178.2 (3)
S11—O13—C13—C12	158.6 (2)	C21—C22—C24—O27	−58.6 (4)
C11—C12—C13—O13	178.8 (2)	C23—C22—C24—O27	57.9 (3)
C15—C12—C13—O13	57.8 (3)	C21—O21—C26—O22	2.7 (5)
C14—C12—C13—O13	−61.5 (3)	C21—O21—C26—C27	−175.9 (3)
S12—O17—C14—C12	176.3 (2)	O22—C26—C27—C212	−173.7 (4)
C13—C12—C14—O17	−59.7 (3)	O21—C26—C27—C212	4.9 (5)
C11—C12—C14—O17	57.8 (4)	O22—C26—C27—C28	5.8 (5)
C15—C12—C14—O17	178.2 (2)	O21—C26—C27—C28	−175.7 (3)
C11—O11—C16—O12	−4.1 (5)	C212—C27—C28—C29	1.4 (6)
C11—O11—C16—C17	176.6 (3)	C26—C27—C28—C29	−178.1 (3)
O12—C16—C17—C112	175.2 (4)	C27—C28—C29—C210	0.4 (6)
O11—C16—C17—C112	−5.6 (5)	C28—C29—C210—C211	−1.5 (7)
O12—C16—C17—C18	−3.0 (6)	C28—C29—C210—Cl21	178.4 (3)
O11—C16—C17—C18	176.2 (3)	C29—C210—C211—C212	0.9 (7)
C112—C17—C18—C19	−1.5 (6)	Cl21—C210—C211—C212	−179.0 (3)
C16—C17—C18—C19	176.7 (3)	C28—C27—C212—C211	−2.0 (6)
C17—C18—C19—C110	1.2 (6)	C26—C27—C212—C211	177.5 (4)
C18—C19—C110—C111	−0.1 (6)	C210—C211—C212—C27	0.9 (6)
C18—C19—C110—Cl11	−177.3 (3)	O25—S21—C213—C214	−54.3 (3)
C19—C110—C111—C112	−0.7 (6)	O24—S21—C213—C214	175.1 (3)
Cl11—C110—C111—C112	176.6 (3)	O23—S21—C213—C214	60.0 (3)
C18—C17—C112—C111	0.7 (6)	S21—C213—C214—C220	72.2 (4)
C16—C17—C112—C111	−177.5 (4)	S21—C213—C214—C219	−59.0 (4)
C110—C111—C112—C17	0.4 (6)	S21—C213—C214—C215	−173.1 (3)
O14—S11—C113—C114	−63.7 (3)	C220—C214—C215—O26	148.9 (4)
O15—S11—C113—C114	70.9 (3)	C219—C214—C215—O26	−103.9 (4)
O13—S11—C113—C114	−173.0 (2)	C213—C214—C215—O26	19.3 (5)
S11—C113—C114—C115	−86.0 (3)	C220—C214—C215—C216	−33.1 (4)
S11—C113—C114—C119	39.8 (4)	C219—C214—C215—C216	74.1 (4)
S11—C113—C114—C120	159.8 (2)	C213—C214—C215—C216	−162.7 (3)
C113—C114—C115—O16	21.3 (5)	O26—C215—C216—C217	175.2 (4)
C119—C114—C115—O16	−111.0 (4)	C214—C215—C216—C217	−2.7 (4)
C120—C114—C115—O16	143.1 (4)	C215—C216—C217—C218	−69.7 (4)
C113—C114—C115—C116	−158.1 (3)	C215—C216—C217—C220	37.0 (4)
C119—C114—C115—C116	69.6 (3)	C216—C217—C218—C219	70.2 (4)
C120—C114—C115—C116	−36.3 (3)	C220—C217—C218—C219	−35.7 (4)
O16—C115—C116—C117	−177.9 (4)	C220—C214—C219—C218	33.7 (4)
C114—C115—C116—C117	1.5 (4)	C215—C214—C219—C218	−71.3 (4)
C115—C116—C117—C118	−73.3 (4)	C213—C214—C219—C218	173.6 (3)
C115—C116—C117—C120	34.6 (4)	C217—C218—C219—C214	1.7 (4)
C116—C117—C118—C119	70.5 (4)	C219—C214—C220—C222	60.9 (4)
C120—C117—C118—C119	−36.8 (4)	C215—C214—C220—C222	167.8 (4)
C115—C114—C119—C118	−71.5 (3)	C213—C214—C220—C222	−75.4 (5)
C113—C114—C119—C118	157.9 (3)	C219—C214—C220—C221	−172.5 (3)
C120—C114—C119—C118	32.6 (4)	C215—C214—C220—C221	−65.6 (4)
C117—C118—C119—C114	2.2 (4)	C213—C214—C220—C221	51.2 (5)
C118—C117—C120—C122	−62.8 (4)	C219—C214—C220—C217	−53.8 (3)
C116—C117—C120—C122	−173.4 (3)	C215—C214—C220—C217	53.1 (3)
C118—C117—C120—C121	172.9 (3)	C213—C214—C220—C217	169.9 (3)
C116—C117—C120—C121	62.3 (3)	C218—C217—C220—C222	−64.8 (4)
C118—C117—C120—C114	55.1 (3)	C216—C217—C220—C222	−175.0 (4)
C116—C117—C120—C114	−55.6 (3)	C218—C217—C220—C214	54.5 (3)
C115—C114—C120—C122	173.3 (3)	C216—C217—C220—C214	−55.7 (3)
C113—C114—C120—C122	−63.4 (4)	C218—C217—C220—C221	172.7 (3)
C119—C114—C120—C122	65.2 (4)	C216—C217—C220—C221	62.5 (4)
C115—C114—C120—C121	−62.7 (3)	O28—S22—C223—C228	−16.3 (4)
C113—C114—C120—C121	60.6 (4)	O29—S22—C223—C228	−150.1 (3)
C119—C114—C120—C121	−170.8 (3)	O27—S22—C223—C228	99.6 (3)
C115—C114—C120—C117	55.2 (3)	O28—S22—C223—C224	165.7 (3)
C113—C114—C120—C117	178.4 (3)	O29—S22—C223—C224	31.9 (4)
C119—C114—C120—C117	−52.9 (3)	O27—S22—C223—C224	−78.4 (3)
O19—S12—C123—C124	−40.8 (4)	C228—C223—C224—C225	−0.4 (6)
O18—S12—C123—C124	−173.5 (3)	S22—C223—C224—C225	177.6 (3)
O17—S12—C123—C124	70.9 (4)	C223—C224—C225—C226	0.9 (7)
O19—S12—C123—C128	139.7 (3)	C224—C225—C226—C227	−1.3 (7)
O18—S12—C123—C128	7.0 (3)	C224—C225—C226—C229	179.3 (4)
O17—S12—C123—C128	−108.6 (3)	C225—C226—C227—C228	1.3 (7)
C128—C123—C124—C125	−1.8 (7)	C229—C226—C227—C228	−179.3 (4)
S12—C123—C124—C125	178.7 (4)	C224—C223—C228—C227	0.5 (6)
C123—C124—C125—C126	0.4 (9)	S22—C223—C228—C227	−177.6 (3)
C124—C125—C126—C127	1.0 (9)	C226—C227—C228—C223	−0.9 (6)