1-Phenyl-1-[(1-phenyl-ethyl)sulfonyl-methyl-sulfon-yl]ethane.

There are two mol-ecules in the asymmetric unit of the title compound, C(17)H(20)O(4)S(2). There are slight differences in the twist of the two rings relative to the S-C-S chain [dihedral angles of 48.41 (18) and 87.58 (16)° in the first mol-ecule and 45.98 (18) and 87.02 (18)° in the second] and the difference in the C-S-C-S torsion angles [176.68 (17) and -77.6 (2)° for the two independent mol-ecules].

Related literature

The title compound is a by-product from the synthesis of 1-phenyl­ethanesulfonic acid. 1-Phenyl-ethanesulfonic acid is a favorable resolving agent for the diastereomeric resolution of dl-p-hydroxy­phenyl­glycine, see: Yoshioka, et al. (1987 ▶). d-p-hydroxy­phenyl­glycine is useful as a side chain in semi-synthetic penicillins or cephalosporins, see: Crast (1970 ▶).

Experimental

Crystal data

C17H20O4S2

M = 352.45

Orthorhombic,

a = 16.662 (3) Å

b = 19.270 (4) Å

c = 22.094 (4) Å

V = 7094 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.20 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.940, T max = 0.951

45855 measured reflections

6253 independent reflections

5060 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.155

S = 1.11

6253 reflections

420 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049423/fl2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049423/fl2264Isup2.hkl

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

C17H20O4S2	Dx = 1.320 Mg m−3
Mr = 352.45	Melting point = 443.0–442.0 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 16.662 (3) Å	Cell parameters from 12971 reflections
b = 19.270 (4) Å	θ = 2.1–27.1°
c = 22.094 (4) Å	µ = 0.32 mm−1
V = 7094 (2) Å3	T = 293 K
Z = 16	Block, light yellow
F(000) = 2976	0.20 × 0.18 × 0.16 mm

Rigaku Saturn CCD area-detector diffractometer	6253 independent reflections
Radiation source: rotating anode	5060 reflections with I > 2σ(I)
confocal	Rint = 0.052
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.1°
ω and φ scans	h = −19→18
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −22→22
Tmin = 0.940, Tmax = 0.951	l = −26→26
45855 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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0766P)2 + 2.0257P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.002
6253 reflections	Δρmax = 0.26 e Å−3
420 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (4)

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.

	x	y	z	Uiso*/Ueq
S1	0.42601 (4)	0.14356 (4)	0.65021 (3)	0.0548 (2)
S2	0.43044 (5)	0.28236 (4)	0.71302 (4)	0.0658 (3)
S3	0.91769 (4)	0.01716 (4)	0.58927 (3)	0.0549 (2)
S4	0.95474 (4)	0.14921 (4)	0.52137 (3)	0.0595 (2)
O1	0.50929 (13)	0.14107 (13)	0.66501 (12)	0.0812 (7)
O2	0.40126 (15)	0.11824 (12)	0.59213 (9)	0.0745 (6)
O3	0.39709 (17)	0.25589 (12)	0.76788 (9)	0.0842 (7)
O4	0.51574 (14)	0.28768 (13)	0.70805 (14)	0.0964 (8)
O5	0.99638 (12)	−0.01180 (13)	0.58338 (9)	0.0716 (6)
O6	0.90029 (12)	0.05709 (11)	0.64260 (8)	0.0626 (5)
O7	1.03467 (12)	0.13461 (14)	0.54114 (11)	0.0783 (7)
O8	0.94424 (13)	0.17500 (12)	0.46090 (9)	0.0680 (6)
C1	0.2418 (2)	0.0672 (2)	0.65607 (16)	0.0807 (10)
H1	0.2706	0.0376	0.6309	0.097*
C2	0.1600 (3)	0.0728 (3)	0.6496 (2)	0.1075 (15)
H2	0.1340	0.0469	0.6200	0.129*
C3	0.1172 (3)	0.1152 (3)	0.6855 (3)	0.1045 (15)
H3	0.0619	0.1186	0.6805	0.125*
C4	0.1543 (2)	0.1535 (2)	0.7294 (2)	0.0925 (12)
H4	0.1244	0.1825	0.7544	0.111*
C5	0.2375 (2)	0.14881 (17)	0.73661 (16)	0.0702 (9)
H5	0.2631	0.1750	0.7662	0.084*
C6	0.28160 (17)	0.10547 (14)	0.69983 (12)	0.0520 (7)
C7	0.37104 (17)	0.09921 (14)	0.70854 (12)	0.0516 (7)
H7	0.3846	0.1210	0.7473	0.062*
C8	0.4035 (2)	0.02521 (17)	0.70958 (16)	0.0789 (10)
H8A	0.3753	−0.0013	0.7396	0.118*
H8B	0.4597	0.0261	0.7192	0.118*
H8C	0.3960	0.0042	0.6706	0.118*
C9	0.39327 (17)	0.23133 (14)	0.65224 (12)	0.0521 (7)
H9A	0.4088	0.2534	0.6145	0.063*
H9B	0.3351	0.2316	0.6541	0.063*
C10	0.3892 (2)	0.36687 (17)	0.69637 (16)	0.0721 (9)
H10	0.4176	0.3848	0.6608	0.086*
C11	0.4098 (3)	0.4138 (2)	0.7492 (2)	0.1226 (18)
H11A	0.3917	0.4601	0.7407	0.184*
H11B	0.4669	0.4141	0.7551	0.184*
H11C	0.3840	0.3970	0.7851	0.184*
C12	0.30164 (19)	0.36350 (15)	0.68054 (15)	0.0607 (8)
C13	0.2783 (2)	0.3767 (2)	0.62202 (18)	0.0861 (11)
H13	0.3168	0.3885	0.5933	0.103*
C14	0.1986 (4)	0.3726 (3)	0.6053 (3)	0.133 (2)
H14	0.1825	0.3822	0.5659	0.160*
C15	0.1430 (3)	0.3535 (3)	0.6495 (5)	0.149 (3)
H15	0.0892	0.3485	0.6393	0.179*
C16	0.1663 (4)	0.3425 (3)	0.7057 (4)	0.133 (2)
H16	0.1279	0.3318	0.7348	0.160*
C17	0.2446 (3)	0.34631 (19)	0.7224 (2)	0.0892 (12)
H17	0.2594	0.3372	0.7622	0.107*
C18	0.7175 (2)	−0.03355 (18)	0.52485 (15)	0.0732 (9)
H18	0.7416	−0.0530	0.4909	0.088*
C19	0.6381 (2)	−0.0121 (2)	0.52199 (19)	0.0934 (12)
H19	0.6089	−0.0180	0.4865	0.112*
C20	0.6028 (2)	0.0175 (2)	0.5712 (2)	0.0885 (11)
H20	0.5498	0.0324	0.5691	0.106*
C21	0.6446 (2)	0.02539 (19)	0.62323 (18)	0.0764 (10)
H21	0.6202	0.0459	0.6566	0.092*
C22	0.72306 (19)	0.00328 (17)	0.62717 (14)	0.0654 (8)
H22	0.7509	0.0081	0.6634	0.078*
C23	0.76090 (17)	−0.02629 (15)	0.57724 (13)	0.0536 (7)
C24	0.84634 (17)	−0.05169 (15)	0.58011 (13)	0.0570 (7)
H24	0.8581	−0.0748	0.5416	0.068*
C25	0.8621 (2)	−0.10406 (19)	0.63070 (16)	0.0807 (10)
H25A	0.8535	−0.0823	0.6692	0.121*
H25B	0.9166	−0.1201	0.6282	0.121*
H25C	0.8262	−0.1427	0.6264	0.121*
C26	0.89830 (16)	0.07083 (16)	0.52489 (11)	0.0534 (7)
H26A	0.9092	0.0441	0.4886	0.064*
H26B	0.8417	0.0825	0.5246	0.064*
C27	0.90765 (19)	0.20848 (18)	0.57385 (14)	0.0671 (9)
H27	0.9089	0.1869	0.6140	0.081*
C28	0.9598 (3)	0.2734 (3)	0.5763 (2)	0.1152 (16)
H28A	0.9649	0.2925	0.5364	0.173*
H28B	1.0120	0.2615	0.5916	0.173*
H28C	0.9354	0.3070	0.6026	0.173*
C29	0.82128 (19)	0.22151 (16)	0.55802 (14)	0.0611 (8)
C30	0.7612 (2)	0.18929 (19)	0.59077 (16)	0.0771 (10)
H30	0.7748	0.1587	0.6217	0.093*
C31	0.6814 (2)	0.2018 (2)	0.5783 (2)	0.0978 (13)
H31	0.6419	0.1802	0.6013	0.117*
C32	0.6603 (3)	0.2448 (2)	0.5333 (2)	0.1013 (14)
H32	0.6063	0.2530	0.5256	0.122*
C33	0.7169 (3)	0.2765 (2)	0.4991 (2)	0.0950 (13)
H33	0.7016	0.3052	0.4674	0.114*
C34	0.7977 (3)	0.26611 (18)	0.51137 (16)	0.0802 (10)
H34	0.8364	0.2889	0.4884	0.096*

	U11	U22	U33	U12	U13	U23
S1	0.0510 (4)	0.0588 (5)	0.0545 (4)	0.0056 (3)	0.0035 (3)	−0.0007 (3)
S2	0.0669 (5)	0.0562 (5)	0.0742 (6)	−0.0133 (4)	−0.0189 (4)	0.0005 (4)
S3	0.0473 (4)	0.0713 (5)	0.0460 (4)	0.0054 (3)	−0.0008 (3)	0.0045 (3)
S4	0.0458 (4)	0.0806 (6)	0.0522 (4)	−0.0071 (4)	0.0008 (3)	0.0088 (4)
O1	0.0452 (12)	0.0881 (17)	0.1104 (18)	0.0122 (11)	0.0044 (12)	−0.0007 (14)
O2	0.1017 (18)	0.0751 (15)	0.0467 (12)	0.0035 (13)	0.0062 (11)	−0.0084 (10)
O3	0.125 (2)	0.0704 (15)	0.0570 (13)	−0.0155 (14)	−0.0186 (13)	−0.0040 (11)
O4	0.0565 (14)	0.0835 (17)	0.149 (2)	−0.0166 (13)	−0.0312 (14)	0.0037 (16)
O5	0.0459 (12)	0.0994 (17)	0.0696 (13)	0.0169 (11)	−0.0043 (10)	0.0080 (12)
O6	0.0709 (14)	0.0757 (14)	0.0413 (10)	−0.0014 (11)	0.0021 (9)	−0.0015 (9)
O7	0.0431 (12)	0.1102 (19)	0.0816 (15)	−0.0108 (12)	−0.0066 (10)	0.0171 (13)
O8	0.0707 (14)	0.0814 (15)	0.0518 (12)	0.0013 (11)	0.0071 (10)	0.0163 (10)
C1	0.071 (2)	0.091 (3)	0.081 (2)	−0.0129 (19)	−0.0115 (18)	−0.009 (2)
C2	0.073 (3)	0.129 (4)	0.120 (4)	−0.028 (3)	−0.027 (3)	0.003 (3)
C3	0.058 (2)	0.115 (4)	0.140 (4)	−0.012 (3)	−0.007 (3)	0.032 (3)
C4	0.069 (2)	0.090 (3)	0.119 (3)	0.001 (2)	0.033 (2)	0.012 (2)
C5	0.061 (2)	0.069 (2)	0.080 (2)	−0.0048 (16)	0.0154 (17)	−0.0030 (17)
C6	0.0534 (16)	0.0508 (16)	0.0517 (16)	−0.0087 (13)	0.0000 (13)	0.0073 (12)
C7	0.0582 (17)	0.0513 (16)	0.0453 (15)	0.0014 (13)	−0.0045 (12)	0.0034 (12)
C8	0.101 (3)	0.0556 (19)	0.080 (2)	0.0167 (18)	−0.0067 (19)	0.0087 (16)
C9	0.0525 (16)	0.0547 (16)	0.0492 (15)	−0.0053 (13)	−0.0019 (12)	0.0091 (12)
C10	0.073 (2)	0.0572 (19)	0.086 (2)	−0.0122 (17)	−0.0067 (18)	0.0010 (16)
C11	0.143 (4)	0.065 (2)	0.160 (4)	−0.013 (3)	−0.052 (3)	−0.033 (3)
C12	0.0620 (19)	0.0499 (16)	0.070 (2)	−0.0009 (14)	0.0113 (15)	−0.0139 (14)
C13	0.087 (3)	0.092 (3)	0.079 (3)	0.019 (2)	0.000 (2)	−0.015 (2)
C14	0.119 (4)	0.134 (4)	0.147 (5)	0.058 (4)	−0.058 (4)	−0.071 (4)
C15	0.065 (3)	0.116 (4)	0.267 (9)	0.003 (3)	−0.021 (5)	−0.110 (6)
C16	0.085 (4)	0.085 (3)	0.229 (7)	−0.012 (3)	0.061 (4)	−0.036 (4)
C17	0.086 (3)	0.073 (2)	0.108 (3)	0.008 (2)	0.037 (2)	−0.010 (2)
C18	0.065 (2)	0.084 (2)	0.070 (2)	0.0042 (18)	−0.0046 (16)	−0.0184 (17)
C19	0.069 (2)	0.111 (3)	0.100 (3)	0.003 (2)	−0.023 (2)	−0.027 (2)
C20	0.053 (2)	0.092 (3)	0.121 (3)	0.0045 (19)	−0.004 (2)	−0.018 (2)
C21	0.061 (2)	0.078 (2)	0.090 (3)	0.0038 (18)	0.0190 (19)	−0.0103 (19)
C22	0.066 (2)	0.070 (2)	0.0601 (18)	0.0020 (16)	0.0102 (15)	−0.0033 (15)
C23	0.0514 (16)	0.0561 (17)	0.0535 (16)	−0.0020 (13)	0.0050 (13)	−0.0014 (13)
C24	0.0564 (18)	0.0613 (18)	0.0534 (16)	0.0067 (14)	0.0012 (13)	−0.0014 (13)
C25	0.090 (3)	0.068 (2)	0.084 (2)	0.0091 (19)	−0.0015 (19)	0.0184 (18)
C26	0.0425 (15)	0.0736 (19)	0.0442 (15)	0.0020 (14)	−0.0010 (11)	0.0033 (13)
C27	0.068 (2)	0.082 (2)	0.0521 (17)	−0.0144 (17)	0.0001 (15)	−0.0049 (15)
C28	0.099 (3)	0.120 (4)	0.126 (4)	−0.050 (3)	0.006 (3)	−0.042 (3)
C29	0.0656 (19)	0.0579 (17)	0.0597 (18)	−0.0021 (15)	0.0042 (15)	−0.0043 (14)
C30	0.071 (2)	0.070 (2)	0.090 (2)	0.0053 (18)	0.0155 (18)	0.0123 (18)
C31	0.070 (3)	0.077 (3)	0.146 (4)	0.005 (2)	0.023 (2)	0.003 (3)
C32	0.081 (3)	0.085 (3)	0.138 (4)	0.025 (2)	−0.011 (3)	−0.019 (3)
C33	0.117 (4)	0.078 (3)	0.091 (3)	0.041 (3)	−0.015 (3)	−0.002 (2)
C34	0.106 (3)	0.065 (2)	0.069 (2)	0.008 (2)	0.014 (2)	0.0018 (17)

S1—O1	1.426 (2)	C13—H13	0.9300
S1—O2	1.433 (2)	C14—C15	1.396 (9)
S1—C9	1.778 (3)	C14—H14	0.9300
S1—C7	1.797 (3)	C15—C16	1.318 (9)
S2—O3	1.428 (2)	C15—H15	0.9300
S2—O4	1.429 (2)	C16—C17	1.358 (7)
S2—C9	1.776 (3)	C16—H16	0.9300
S2—C10	1.805 (3)	C17—H17	0.9300
S3—O5	1.431 (2)	C18—C23	1.372 (4)
S3—O6	1.437 (2)	C18—C19	1.388 (5)
S3—C26	1.788 (3)	C18—H18	0.9300
S3—C24	1.793 (3)	C19—C20	1.362 (5)
S4—O7	1.430 (2)	C19—H19	0.9300
S4—O8	1.436 (2)	C20—C21	1.352 (5)
S4—C26	1.781 (3)	C20—H20	0.9300
S4—C27	1.807 (3)	C21—C22	1.377 (4)
C1—C2	1.374 (5)	C21—H21	0.9300
C1—C6	1.385 (4)	C22—C23	1.392 (4)
C1—H1	0.9300	C22—H22	0.9300
C2—C3	1.345 (6)	C23—C24	1.507 (4)
C2—H2	0.9300	C24—C25	1.529 (4)
C3—C4	1.366 (6)	C24—H24	0.9800
C3—H3	0.9300	C25—H25A	0.9600
C4—C5	1.398 (5)	C25—H25B	0.9600
C4—H4	0.9300	C25—H25C	0.9600
C5—C6	1.377 (4)	C26—H26A	0.9700
C5—H5	0.9300	C26—H26B	0.9700
C6—C7	1.507 (4)	C27—C29	1.502 (4)
C7—C8	1.526 (4)	C27—C28	1.524 (5)
C7—H7	0.9800	C27—H27	0.9800
C8—H8A	0.9600	C28—H28A	0.9600
C8—H8B	0.9600	C28—H28B	0.9600
C8—H8C	0.9600	C28—H28C	0.9600
C9—H9A	0.9700	C29—C30	1.383 (4)
C9—H9B	0.9700	C29—C34	1.398 (5)
C10—C12	1.501 (4)	C30—C31	1.379 (5)
C10—C11	1.517 (5)	C30—H30	0.9300
C10—H10	0.9800	C31—C32	1.341 (6)
C11—H11A	0.9600	C31—H31	0.9300
C11—H11B	0.9600	C32—C33	1.353 (6)
C11—H11C	0.9600	C32—H32	0.9300
C12—C17	1.367 (5)	C33—C34	1.388 (5)
C12—C13	1.374 (5)	C33—H33	0.9300
C13—C14	1.382 (6)	C34—H34	0.9300
O1—S1—O2	118.26 (15)	C13—C14—C15	117.8 (6)
O1—S1—C9	108.95 (14)	C13—C14—H14	121.1
O2—S1—C9	104.96 (13)	C15—C14—H14	121.1
O1—S1—C7	108.39 (14)	C16—C15—C14	120.5 (6)
O2—S1—C7	109.48 (14)	C16—C15—H15	119.8
C9—S1—C7	106.14 (13)	C14—C15—H15	119.8
O3—S2—O4	118.55 (16)	C15—C16—C17	122.0 (6)
O3—S2—C9	107.97 (13)	C15—C16—H16	119.0
O4—S2—C9	109.17 (16)	C17—C16—H16	119.0
O3—S2—C10	110.31 (17)	C16—C17—C12	119.9 (5)
O4—S2—C10	107.35 (16)	C16—C17—H17	120.1
C9—S2—C10	102.27 (14)	C12—C17—H17	120.1
O5—S3—O6	117.93 (13)	C23—C18—C19	120.7 (3)
O5—S3—C26	108.59 (13)	C23—C18—H18	119.6
O6—S3—C26	107.82 (13)	C19—C18—H18	119.6
O5—S3—C24	107.99 (14)	C20—C19—C18	120.0 (3)
O6—S3—C24	110.80 (13)	C20—C19—H19	120.0
C26—S3—C24	102.61 (13)	C18—C19—H19	120.0
O7—S4—O8	117.77 (13)	C21—C20—C19	120.2 (3)
O7—S4—C26	108.16 (14)	C21—C20—H20	119.9
O8—S4—C26	105.66 (13)	C19—C20—H20	119.9
O7—S4—C27	109.44 (15)	C20—C21—C22	120.5 (3)
O8—S4—C27	108.98 (15)	C20—C21—H21	119.7
C26—S4—C27	106.18 (14)	C22—C21—H21	119.7
C2—C1—C6	120.4 (4)	C21—C22—C23	120.4 (3)
C2—C1—H1	119.8	C21—C22—H22	119.8
C6—C1—H1	119.8	C23—C22—H22	119.8
C3—C2—C1	120.8 (4)	C18—C23—C22	118.1 (3)
C3—C2—H2	119.6	C18—C23—C24	120.0 (3)
C1—C2—H2	119.6	C22—C23—C24	121.8 (3)
C2—C3—C4	120.4 (4)	C23—C24—C25	114.1 (3)
C2—C3—H3	119.8	C23—C24—S3	113.0 (2)
C4—C3—H3	119.8	C25—C24—S3	107.0 (2)
C3—C4—C5	119.7 (4)	C23—C24—H24	107.5
C3—C4—H4	120.2	C25—C24—H24	107.5
C5—C4—H4	120.2	S3—C24—H24	107.5
C6—C5—C4	120.0 (3)	C24—C25—H25A	109.5
C6—C5—H5	120.0	C24—C25—H25B	109.5
C4—C5—H5	120.0	H25A—C25—H25B	109.5
C5—C6—C1	118.6 (3)	C24—C25—H25C	109.5
C5—C6—C7	120.0 (3)	H25A—C25—H25C	109.5
C1—C6—C7	121.3 (3)	H25B—C25—H25C	109.5
C6—C7—C8	115.3 (3)	S4—C26—S3	115.46 (15)
C6—C7—S1	111.98 (18)	S4—C26—H26A	108.4
C8—C7—S1	105.9 (2)	S3—C26—H26A	108.4
C6—C7—H7	107.8	S4—C26—H26B	108.4
C8—C7—H7	107.8	S3—C26—H26B	108.4
S1—C7—H7	107.8	H26A—C26—H26B	107.5
C7—C8—H8A	109.5	C29—C27—C28	114.7 (3)
C7—C8—H8B	109.5	C29—C27—S4	111.9 (2)
H8A—C8—H8B	109.5	C28—C27—S4	107.1 (2)
C7—C8—H8C	109.5	C29—C27—H27	107.6
H8A—C8—H8C	109.5	C28—C27—H27	107.6
H8B—C8—H8C	109.5	S4—C27—H27	107.6
S2—C9—S1	116.03 (15)	C27—C28—H28A	109.5
S2—C9—H9A	108.3	C27—C28—H28B	109.5
S1—C9—H9A	108.3	H28A—C28—H28B	109.5
S2—C9—H9B	108.3	C27—C28—H28C	109.5
S1—C9—H9B	108.3	H28A—C28—H28C	109.5
H9A—C9—H9B	107.4	H28B—C28—H28C	109.5
C12—C10—C11	115.2 (3)	C30—C29—C34	117.3 (3)
C12—C10—S2	112.2 (2)	C30—C29—C27	119.8 (3)
C11—C10—S2	107.2 (3)	C34—C29—C27	122.9 (3)
C12—C10—H10	107.3	C31—C30—C29	121.0 (4)
C11—C10—H10	107.3	C31—C30—H30	119.5
S2—C10—H10	107.3	C29—C30—H30	119.5
C10—C11—H11A	109.5	C32—C31—C30	120.6 (4)
C10—C11—H11B	109.5	C32—C31—H31	119.7
H11A—C11—H11B	109.5	C30—C31—H31	119.7
C10—C11—H11C	109.5	C31—C32—C33	120.6 (4)
H11A—C11—H11C	109.5	C31—C32—H32	119.7
H11B—C11—H11C	109.5	C33—C32—H32	119.7
C17—C12—C13	119.0 (4)	C32—C33—C34	120.2 (4)
C17—C12—C10	121.9 (3)	C32—C33—H33	119.9
C13—C12—C10	119.1 (3)	C34—C33—H33	119.9
C12—C13—C14	120.9 (4)	C33—C34—C29	120.3 (4)
C12—C13—H13	119.6	C33—C34—H34	119.9
C14—C13—H13	119.6	C29—C34—H34	119.9
C6—C1—C2—C3	−0.1 (7)	C23—C18—C19—C20	1.1 (6)
C1—C2—C3—C4	−0.3 (7)	C18—C19—C20—C21	−0.9 (7)
C2—C3—C4—C5	0.6 (7)	C19—C20—C21—C22	−0.3 (6)
C3—C4—C5—C6	−0.5 (6)	C20—C21—C22—C23	1.2 (5)
C4—C5—C6—C1	0.1 (5)	C19—C18—C23—C22	−0.2 (5)
C4—C5—C6—C7	−178.6 (3)	C19—C18—C23—C24	178.3 (3)
C2—C1—C6—C5	0.2 (5)	C21—C22—C23—C18	−1.0 (5)
C2—C1—C6—C7	178.9 (3)	C21—C22—C23—C24	−179.4 (3)
C5—C6—C7—C8	132.9 (3)	C18—C23—C24—C25	−123.5 (3)
C1—C6—C7—C8	−45.7 (4)	C22—C23—C24—C25	54.9 (4)
C5—C6—C7—S1	−105.8 (3)	C18—C23—C24—S3	114.0 (3)
C1—C6—C7—S1	75.5 (3)	C22—C23—C24—S3	−67.6 (3)
O1—S1—C7—C6	174.3 (2)	O5—S3—C24—C23	−172.48 (19)
O2—S1—C7—C6	−55.4 (2)	O6—S3—C24—C23	57.0 (2)
C9—S1—C7—C6	57.4 (2)	C26—S3—C24—C23	−57.9 (2)
O1—S1—C7—C8	−59.3 (2)	O5—S3—C24—C25	61.2 (2)
O2—S1—C7—C8	71.1 (2)	O6—S3—C24—C25	−69.4 (2)
C9—S1—C7—C8	−176.2 (2)	C26—S3—C24—C25	175.8 (2)
O3—S2—C9—S1	−67.0 (2)	O7—S4—C26—S3	39.8 (2)
O4—S2—C9—S1	63.2 (2)	O8—S4—C26—S3	166.74 (15)
C10—S2—C9—S1	176.68 (17)	C27—S4—C26—S3	−77.6 (2)
O1—S1—C9—S2	−41.5 (2)	O5—S3—C26—S4	−69.9 (2)
O2—S1—C9—S2	−169.10 (16)	O6—S3—C26—S4	58.95 (19)
C7—S1—C9—S2	75.01 (19)	C24—S3—C26—S4	175.96 (16)
O3—S2—C10—C12	−67.9 (3)	O7—S4—C27—C29	−175.6 (2)
O4—S2—C10—C12	161.6 (2)	O8—S4—C27—C29	54.3 (3)
C9—S2—C10—C12	46.8 (3)	C26—S4—C27—C29	−59.1 (3)
O3—S2—C10—C11	59.5 (3)	O7—S4—C27—C28	57.9 (3)
O4—S2—C10—C11	−71.0 (3)	O8—S4—C27—C28	−72.2 (3)
C9—S2—C10—C11	174.2 (3)	C26—S4—C27—C28	174.4 (3)
C11—C10—C12—C17	−54.8 (4)	C28—C27—C29—C30	−134.8 (3)
S2—C10—C12—C17	68.2 (4)	S4—C27—C29—C30	103.0 (3)
C11—C10—C12—C13	126.6 (4)	C28—C27—C29—C34	44.4 (4)
S2—C10—C12—C13	−110.4 (3)	S4—C27—C29—C34	−77.8 (4)
C17—C12—C13—C14	−0.2 (5)	C34—C29—C30—C31	−1.0 (5)
C10—C12—C13—C14	178.5 (3)	C27—C29—C30—C31	178.2 (3)
C12—C13—C14—C15	−1.1 (7)	C29—C30—C31—C32	1.0 (6)
C13—C14—C15—C16	2.5 (8)	C30—C31—C32—C33	0.4 (7)
C14—C15—C16—C17	−2.8 (9)	C31—C32—C33—C34	−1.8 (6)
C15—C16—C17—C12	1.5 (7)	C32—C33—C34—C29	1.7 (6)
C13—C12—C17—C16	0.0 (5)	C30—C29—C34—C33	−0.3 (5)
C10—C12—C17—C16	−178.6 (4)	C27—C29—C34—C33	−179.5 (3)