Octa-O-acetyl-[beta],[beta]-thiotrehalose

The structure of the title compound, C₂₈H₃₈O₁₈S, has been determined. The torsion angles of the glycosidic linkage in the non-reducing disaccharide, [varphi]_H and [varphi]_H', have values of 3 and 53°, respectively. The latter torsion angle is in agreement with the exo-anomeric effect, whereas the former shows an eclipsed conformation. Both glyco­pyran­osyl residues adopt a slightly distorted chair conformation.

Computing details

Data collection: Expose (Stoe & Cie, 1997); cell refinement: Cell (Stoe & Cie, 1997); data reduction: Integrate (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON98 (Spek, 1998).

Octa-O-acetyl β,β-thio-Trehalose

Crystal data

C28H38O18S	F(000) = 732
Mr = 694.64	Dx = 1.339 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 14.463 (4) Å	Cell parameters from 1068 reflections
b = 5.805 (2) Å	θ = 2.0–25.9°
c = 20.927 (7) Å	µ = 0.17 mm^−1
β = 101.27 (4)°	T = 293 K
V = 1723.0 (10) Å^3	Prism, colourless
Z = 2	0.20 × 0.05 × 0.05 mm

Data collection

STOE IPDS diffractometer	2091 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.103
Graphite monochromator	θmax = 25.9°, θmin = 2.0°
Detector resolution: 6.0 pixels mm^-1	h = −17→17
area detector scans	k = −7→6
13406 measured reflections	l = −25→25
6524 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2)]
wR(F^2) = 0.124	(Δ/σ)max = 0.001
S = 1.32	Δρmax = 0.81 e Å^−3
6524 reflections	Δρmin = −1.34 e Å^−3
425 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
116 restraints	Extinction coefficient: 0.0095 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (18)

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
S	0.53792 (12)	0.4249 (4)	0.68600 (10)	0.0639 (7)
C1	0.6308 (4)	0.2266 (15)	0.6828 (3)	0.055 (2)
H1	0.6045	0.0764	0.6674	0.066*
C2	0.6983 (4)	0.3110 (15)	0.6394 (3)	0.053 (2)
H2	0.7252	0.4613	0.6541	0.064*
O2	0.6499 (3)	0.3200 (10)	0.5710 (2)	0.0550 (14)
C21	0.6223 (5)	0.542 (2)	0.5472 (4)	0.061 (2)
O21	0.6331 (4)	0.7011 (12)	0.5815 (3)	0.083 (2)
C22	0.5764 (5)	0.5254 (19)	0.4769 (3)	0.086 (3)
H21	0.5786	0.3688	0.4625	0.129*
H22	0.6092	0.6227	0.4517	0.129*
H23	0.5119	0.5742	0.4715	0.129*
C3	0.7766 (4)	0.1301 (14)	0.6394 (3)	0.053 (2)
H3	0.7520	−0.0059	0.6139	0.063*
O3	0.8468 (3)	0.2486 (9)	0.6102 (2)	0.0572 (14)
C31	0.8995 (6)	0.118 (2)	0.5751 (5)	0.075 (3)
O31	0.8904 (4)	−0.0818 (16)	0.5661 (3)	0.096 (2)
C32	0.9683 (5)	0.279 (2)	0.5518 (4)	0.120 (4)
H31	0.9574	0.4341	0.5646	0.180*
H32	0.9595	0.2712	0.5052	0.180*
H33	1.0316	0.2345	0.5708	0.180*
C4	0.8234 (4)	0.0629 (15)	0.7093 (3)	0.053 (2)
H4	0.8670	0.1840	0.7291	0.063*
O4	0.8731 (3)	−0.1557 (9)	0.7093 (2)	0.0605 (16)
C41	0.9717 (5)	−0.1506 (19)	0.7223 (5)	0.076 (3)
O41	1.0126 (3)	0.0264 (13)	0.7275 (4)	0.105 (2)
C42	1.0083 (5)	−0.3871 (16)	0.7228 (4)	0.085 (3)
H41	0.9568	−0.4942	0.7170	0.128*
H42	1.0499	−0.4164	0.7637	0.128*
H43	1.0422	−0.4051	0.6880	0.128*
C5	0.7494 (4)	0.0126 (15)	0.7526 (3)	0.056 (2)
H5	0.7137	−0.1257	0.7361	0.067*
C6	0.7913 (5)	−0.0212 (17)	0.8230 (3)	0.070 (3)
H6A	0.7420	−0.0305	0.8484	0.084*
H6B	0.8280	−0.1621	0.8293	0.084*
O6	0.8525 (3)	0.1815 (11)	0.8432 (2)	0.0716 (17)
C61	0.8970 (7)	0.191 (3)	0.9078 (5)	0.093 (3)
O61	0.8818 (6)	0.0370 (19)	0.9434 (3)	0.160 (4)
C62	0.9567 (5)	0.394 (2)	0.9218 (4)	0.108 (4)
H61	0.9549	0.4802	0.8824	0.162*
H62	1.0203	0.3475	0.9390	0.162*
H63	0.9341	0.4888	0.9531	0.162*
O5	0.6860 (3)	0.2049 (10)	0.7472 (2)	0.0569 (15)
C1'	0.4740 (4)	0.2558 (16)	0.7339 (3)	0.058 (2)
H1'	0.5078	0.1113	0.7464	0.070*
C2'	0.4616 (4)	0.3865 (15)	0.7951 (3)	0.056 (2)
H2'	0.4400	0.5444	0.7845	0.067*
O2'	0.5507 (3)	0.3852 (10)	0.8402 (2)	0.0622 (15)
C21'	0.5953 (6)	0.590 (2)	0.8574 (4)	0.066 (3)
O21'	0.5645 (4)	0.7743 (12)	0.8374 (3)	0.087 (2)
C22'	0.6854 (4)	0.5497 (18)	0.9038 (4)	0.082 (3)
H21'	0.6930	0.3879	0.9127	0.123*
H22'	0.6847	0.6312	0.9436	0.123*
H23'	0.7369	0.6041	0.8851	0.123*
C3'	0.3934 (4)	0.2574 (14)	0.8317 (4)	0.055 (2)
H3'	0.4241	0.1194	0.8531	0.066*
O3'	0.3752 (3)	0.4253 (10)	0.8816 (3)	0.0650 (14)
C31'	0.3818 (6)	0.354 (2)	0.9449 (5)	0.077 (3)
O31'	0.3996 (5)	0.1564 (14)	0.9602 (3)	0.113 (3)
C32'	0.3624 (6)	0.546 (2)	0.9868 (4)	0.101 (3)
H31'	0.3522	0.6848	0.9616	0.152*
H32'	0.4152	0.5661	1.0221	0.152*
H33'	0.3071	0.5112	1.0040	0.152*
C4'	0.3017 (4)	0.1933 (16)	0.7878 (4)	0.061 (2)
H4'	0.2628	0.3293	0.7739	0.073*
O4'	0.2525 (3)	0.0275 (10)	0.8212 (2)	0.0700 (17)
C41'	0.1832 (6)	0.111 (2)	0.8524 (5)	0.078 (3)
O41'	0.1598 (4)	0.3051 (14)	0.8488 (4)	0.096 (2)
C42'	0.1448 (5)	−0.0890 (19)	0.8855 (4)	0.105 (4)
H41'	0.1786	−0.2267	0.8790	0.158*
H42'	0.0791	−0.1092	0.8671	0.158*
H43'	0.1524	−0.0583	0.9313	0.158*
C5'	0.3267 (4)	0.0615 (16)	0.7287 (3)	0.062 (2)
H5'	0.3625	−0.0775	0.7443	0.074*
C6'	0.2385 (5)	−0.007 (2)	0.6775 (4)	0.099 (4)
H6A'	0.1949	−0.0926	0.6982	0.119*
H6B'	0.2066	0.1304	0.6579	0.119*
O6'	0.2673 (5)	−0.1426 (18)	0.6295 (4)	0.143 (4)
C61'	0.2379 (8)	−0.333 (3)	0.6172 (7)	0.114 (4)
O61'	0.1890 (8)	−0.415 (2)	0.6486 (8)	0.304 (9)
C62'	0.2739 (5)	−0.4741 (18)	0.5692 (4)	0.095 (3)
H61'	0.2438	−0.6222	0.5659	0.143*
H62'	0.3408	−0.4934	0.5829	0.143*
H63'	0.2607	−0.3990	0.5276	0.143*
O5'	0.3831 (3)	0.2069 (11)	0.6965 (2)	0.0666 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0488 (10)	0.0704 (18)	0.0754 (15)	0.0045 (11)	0.0194 (10)	0.0039 (14)
C1	0.039 (3)	0.073 (7)	0.054 (4)	0.003 (4)	0.012 (3)	0.002 (5)
C2	0.036 (3)	0.068 (6)	0.055 (4)	0.000 (3)	0.009 (3)	0.001 (4)
O2	0.058 (3)	0.060 (4)	0.044 (3)	−0.009 (3)	0.006 (2)	0.001 (3)
C21	0.045 (4)	0.065 (7)	0.075 (6)	0.003 (5)	0.015 (4)	0.007 (5)
O21	0.077 (4)	0.058 (5)	0.106 (5)	−0.003 (4)	−0.003 (3)	−0.003 (4)
C22	0.079 (5)	0.113 (9)	0.060 (5)	0.019 (6)	0.001 (4)	0.013 (5)
C3	0.044 (4)	0.060 (6)	0.059 (4)	−0.006 (3)	0.024 (3)	0.004 (4)
O3	0.049 (3)	0.067 (4)	0.059 (3)	−0.007 (3)	0.021 (2)	−0.002 (3)
C31	0.056 (5)	0.098 (8)	0.078 (7)	−0.001 (6)	0.033 (5)	−0.016 (7)
O31	0.096 (4)	0.099 (6)	0.102 (5)	0.009 (5)	0.042 (4)	−0.015 (6)
C32	0.102 (6)	0.158 (10)	0.123 (8)	−0.053 (7)	0.078 (6)	−0.039 (8)
C4	0.047 (4)	0.049 (6)	0.066 (5)	0.003 (4)	0.020 (3)	0.003 (4)
O4	0.039 (2)	0.063 (5)	0.079 (4)	0.008 (2)	0.011 (2)	−0.002 (3)
C41	0.044 (4)	0.081 (7)	0.100 (7)	0.011 (4)	0.008 (5)	−0.003 (7)
O41	0.055 (4)	0.069 (5)	0.184 (7)	−0.006 (3)	0.008 (4)	−0.012 (5)
C42	0.054 (5)	0.067 (6)	0.135 (8)	0.021 (4)	0.023 (5)	0.006 (7)
C5	0.050 (4)	0.067 (7)	0.055 (4)	0.003 (4)	0.018 (3)	0.004 (4)
C6	0.063 (5)	0.094 (8)	0.050 (4)	−0.005 (5)	0.004 (4)	0.009 (5)
O6	0.066 (3)	0.095 (5)	0.052 (3)	0.001 (3)	0.005 (3)	0.002 (3)
C61	0.078 (6)	0.138 (11)	0.057 (6)	0.008 (6)	0.003 (5)	−0.011 (6)
O61	0.183 (7)	0.180 (10)	0.087 (6)	−0.028 (7)	−0.046 (5)	0.051 (6)
C62	0.086 (6)	0.138 (10)	0.094 (7)	−0.002 (6)	0.001 (5)	−0.040 (7)
O5	0.044 (3)	0.074 (5)	0.052 (3)	0.010 (3)	0.008 (2)	0.006 (3)
C1'	0.034 (3)	0.078 (7)	0.062 (4)	−0.012 (4)	0.007 (3)	0.000 (5)
C2'	0.040 (3)	0.059 (7)	0.069 (5)	−0.008 (4)	0.012 (3)	0.010 (4)
O2'	0.052 (3)	0.067 (5)	0.065 (3)	−0.004 (3)	0.007 (2)	−0.003 (3)
C21'	0.060 (5)	0.072 (7)	0.068 (6)	−0.003 (5)	0.019 (4)	−0.014 (6)
O21'	0.078 (4)	0.069 (5)	0.106 (5)	−0.008 (4)	0.001 (3)	−0.004 (4)
C22'	0.063 (4)	0.096 (8)	0.084 (6)	−0.008 (5)	0.008 (4)	−0.007 (6)
C3'	0.059 (4)	0.036 (6)	0.074 (5)	0.002 (4)	0.021 (4)	−0.003 (4)
O3'	0.065 (3)	0.056 (4)	0.077 (3)	0.003 (3)	0.022 (3)	−0.006 (3)
C31'	0.083 (6)	0.080 (8)	0.074 (6)	−0.006 (6)	0.030 (5)	−0.001 (6)
O31'	0.176 (6)	0.084 (6)	0.093 (5)	0.025 (5)	0.059 (5)	0.016 (4)
C32'	0.133 (7)	0.101 (9)	0.077 (6)	0.014 (7)	0.039 (5)	−0.020 (6)
C4'	0.053 (4)	0.053 (6)	0.080 (5)	−0.009 (4)	0.021 (4)	−0.005 (4)
O4'	0.059 (3)	0.065 (4)	0.094 (4)	0.002 (3)	0.035 (3)	0.009 (4)
C41'	0.059 (5)	0.096 (8)	0.087 (7)	0.006 (6)	0.029 (5)	0.004 (7)
O41'	0.076 (4)	0.097 (6)	0.125 (6)	0.011 (4)	0.047 (4)	0.001 (5)
C42'	0.077 (5)	0.130 (9)	0.120 (8)	0.002 (6)	0.046 (5)	0.058 (8)
C5'	0.057 (4)	0.063 (7)	0.069 (5)	−0.016 (4)	0.021 (4)	−0.005 (4)
C6'	0.054 (4)	0.142 (11)	0.105 (7)	−0.038 (5)	0.021 (4)	−0.048 (7)
O6'	0.141 (6)	0.169 (9)	0.138 (6)	−0.081 (6)	0.073 (5)	−0.094 (6)
C61'	0.084 (7)	0.104 (10)	0.170 (12)	0.002 (7)	0.063 (7)	−0.026 (8)
O61'	0.326 (12)	0.147 (10)	0.55 (2)	−0.062 (9)	0.349 (15)	−0.085 (12)
C62'	0.119 (7)	0.083 (9)	0.080 (6)	−0.016 (6)	0.012 (5)	−0.007 (6)
O5'	0.040 (2)	0.088 (5)	0.073 (3)	−0.016 (3)	0.013 (2)	0.008 (3)

Geometric parameters (Å, º)

S—C1	1.780 (7)	C62—H63	0.9600
S—C1'	1.784 (7)	C1'—O5'	1.420 (6)
C1—C1'	2.694 (8)	C1'—C2'	1.530 (9)
C1—O5	1.432 (7)	C1'—H1'	0.9800
C1—C2	1.537 (8)	C2'—O2'	1.441 (7)
C1—H1	0.9800	C2'—C3'	1.555 (8)
C2—O2	1.467 (7)	C2'—H2'	0.9800
C2—C3	1.545 (9)	O2'—C21'	1.367 (11)
C2—H2	0.9800	C21'—O21'	1.202 (10)
O2—C21	1.408 (11)	C21'—C22'	1.484 (10)
C21—O21	1.164 (10)	C22'—H21'	0.9600
C21—C22	1.492 (10)	C22'—H22'	0.9600
C22—H21	0.9600	C22'—H23'	0.9600
C22—H22	0.9600	C3'—O3'	1.488 (8)
C22—H23	0.9600	C3'—C4'	1.505 (9)
C3—O3	1.457 (7)	C3'—H3'	0.9800
C3—C4	1.537 (9)	O3'—C31'	1.374 (10)
C3—H3	0.9800	C31'—O31'	1.203 (11)
O3—C31	1.382 (10)	C31'—C32'	1.480 (13)
C31—O31	1.180 (10)	C32'—H31'	0.9600
C31—C32	1.513 (12)	C32'—H32'	0.9600
C32—H31	0.9600	C32'—H33'	0.9600
C32—H32	0.9600	C4'—O4'	1.455 (8)
C32—H33	0.9600	C4'—C5'	1.555 (9)
C4—O4	1.459 (9)	C4'—H4'	0.9800
C4—C5	1.558 (8)	O4'—C41'	1.387 (10)
C4—H4	0.9800	C41'—O41'	1.174 (11)
O4—C41	1.399 (8)	C41'—C42'	1.512 (13)
C41—O41	1.180 (10)	C42'—H41'	0.9600
C41—C42	1.471 (12)	C42'—H42'	0.9600
C42—H41	0.9600	C42'—H43'	0.9600
C42—H42	0.9600	C5'—O5'	1.431 (8)
C42—H43	0.9600	C5'—C6'	1.550 (9)
C5—O5	1.435 (8)	C5'—H5'	0.9800
C5—C6	1.493 (8)	C6'—O6'	1.402 (10)
C5—H5	0.9800	C6'—H6A'	0.9700
C6—O6	1.483 (9)	C6'—H6B'	0.9700
C6—H6A	0.9700	O6'—C61'	1.193 (13)
C6—H6B	0.9700	C61'—O61'	1.158 (14)
O6—C61	1.380 (10)	C61'—C62'	1.469 (13)
C61—O61	1.210 (12)	C62'—H61'	0.9600
C61—C62	1.458 (15)	C62'—H62'	0.9600
C62—H61	0.9600	C62'—H63'	0.9600
C62—H62	0.9600
C1—S—C1'	98.2 (4)	C1—O5—C5	111.9 (6)
H1'—C1'—C1	68.8	O5'—C1'—C2'	108.2 (5)
H1—C1—C1'	83.30	O5'—C1'—S	109.0 (4)
O5—C1—C2	106.4 (5)	C2'—C1'—S	110.9 (6)
O5—C1—S	107.9 (5)	O5'—C1'—H1'	109.6
C2—C1—S	112.8 (6)	C2'—C1'—H1'	109.6
O5—C1—H1	109.9	S—C1'—H1'	109.6
C2—C1—H1	109.9	O2'—C2'—C1'	108.1 (5)
S—C1—H1	109.9	O2'—C2'—C3'	104.3 (5)
O2—C2—C1	110.6 (5)	C1'—C2'—C3'	111.3 (6)
O2—C2—C3	103.5 (6)	O2'—C2'—H2'	111.0
C1—C2—C3	109.5 (6)	C1'—C2'—H2'	111.0
O2—C2—H2	111.0	C3'—C2'—H2'	111.0
C1—C2—H2	111.0	C21'—O2'—C2'	118.9 (7)
C3—C2—H2	111.0	O21'—C21'—O2'	123.9 (9)
C21—O2—C2	115.2 (6)	O21'—C21'—C22'	126.0 (10)
O21—C21—O2	120.9 (9)	O2'—C21'—C22'	110.1 (9)
O21—C21—C22	129.7 (11)	C21'—C22'—H21'	109.5
O2—C21—C22	109.4 (9)	C21'—C22'—H22'	109.5
C21—C22—H21	109.5	H21'—C22'—H22'	109.5
C21—C22—H22	109.5	C21'—C22'—H23'	109.5
H21—C22—H22	109.5	H21'—C22'—H23'	109.5
C21—C22—H23	109.5	H22'—C22'—H23'	109.5
H21—C22—H23	109.5	O3'—C3'—C4'	109.6 (5)
H22—C22—H23	109.5	O3'—C3'—C2'	104.2 (6)
O3—C3—C4	107.8 (5)	C4'—C3'—C2'	112.7 (6)
O3—C3—C2	104.5 (6)	O3'—C3'—H3'	110.1
C4—C3—C2	111.0 (6)	C4'—C3'—H3'	110.1
O3—C3—H3	111.1	C2'—C3'—H3'	110.1
C4—C3—H3	111.1	C31'—O3'—C3'	119.3 (7)
C2—C3—H3	111.1	O31'—C31'—O3'	121.0 (10)
C31—O3—C3	117.8 (7)	O31'—C31'—C32'	128.0 (11)
O31—C31—O3	124.6 (8)	O3'—C31'—C32'	111.0 (10)
O31—C31—C32	128.0 (9)	C31'—C32'—H31'	109.5
O3—C31—C32	107.4 (9)	C31'—C32'—H32'	109.5
C31—C32—H31	109.5	H31'—C32'—H32'	109.5
C31—C32—H32	109.5	C31'—C32'—H33'	109.5
H31—C32—H32	109.5	H31'—C32'—H33'	109.5
C31—C32—H33	109.5	H32'—C32'—H33'	109.5
H31—C32—H33	109.5	O4'—C4'—C3'	109.0 (6)
H32—C32—H33	109.5	O4'—C4'—C5'	105.6 (7)
O4—C4—C3	110.2 (6)	C3'—C4'—C5'	107.1 (5)
O4—C4—C5	103.4 (6)	O4'—C4'—H4'	111.7
C3—C4—C5	112.1 (5)	C3'—C4'—H4'	111.7
O4—C4—H4	110.3	C5'—C4'—H4'	111.7
C3—C4—H4	110.3	C41'—O4'—C4'	117.5 (7)
C5—C4—H4	110.3	O41'—C41'—O4'	122.1 (10)
C41—O4—C4	117.7 (6)	O41'—C41'—C42'	129.8 (9)
O41—C41—O4	120.7 (8)	O4'—C41'—C42'	108.1 (9)
O41—C41—C42	129.7 (7)	C41'—C42'—H41'	109.5
O4—C41—C42	109.5 (8)	C41'—C42'—H42'	109.5
C41—C42—H41	109.5	H41'—C42'—H42'	109.5
C41—C42—H42	109.5	C41'—C42'—H43'	109.5
H41—C42—H42	109.5	H41'—C42'—H43'	109.5
C41—C42—H43	109.5	H42'—C42'—H43'	109.5
H41—C42—H43	109.5	O5'—C5'—C6'	107.1 (6)
H42—C42—H43	109.5	O5'—C5'—C4'	109.1 (7)
O5—C5—C6	108.0 (6)	C6'—C5'—C4'	112.8 (6)
O5—C5—C4	108.0 (6)	O5'—C5'—H5'	109.3
C6—C5—C4	114.0 (5)	C6'—C5'—H5'	109.3
O5—C5—H5	108.9	C4'—C5'—H5'	109.3
C6—C5—H5	108.9	O6'—C6'—C5'	108.6 (7)
C4—C5—H5	108.9	O6'—C6'—H6A'	110.0
O6—C6—C5	106.3 (7)	C5'—C6'—H6A'	110.0
O6—C6—H6A	110.5	O6'—C6'—H6B'	110.0
C5—C6—H6A	110.5	C5'—C6'—H6B'	110.0
O6—C6—H6B	110.5	H6A'—C6'—H6B'	108.4
C5—C6—H6B	110.5	C61'—O6'—C6'	122.1 (10)
H6A—C6—H6B	108.7	O61'—C61'—O6'	119.5 (14)
C61—O6—C6	116.6 (8)	O61'—C61'—C62'	119.6 (14)
O61—C61—O6	117.9 (11)	O6'—C61'—C62'	120.3 (12)
O61—C61—C62	130.2 (10)	C61'—C62'—H61'	109.5
O6—C61—C62	111.9 (10)	C61'—C62'—H62'	109.5
C61—C62—H61	109.5	H61'—C62'—H62'	109.5
C61—C62—H62	109.5	C61'—C62'—H63'	109.5
H61—C62—H62	109.5	H61'—C62'—H63'	109.5
C61—C62—H63	109.5	H62'—C62'—H63'	109.5
H61—C62—H63	109.5	C1'—O5'—C5'	114.2 (5)
H62—C62—H63	109.5
C1'—S—C1—O5	−67.1 (6)	O5'—C1'—C2'—O2'	165.8 (6)
C1'—S—C1—C2	175.7 (5)	S—C1'—C2'—O2'	−74.7 (7)
O5—C1—C2—O2	175.2 (6)	O5'—C1'—C2'—C3'	51.8 (8)
S—C1—C2—O2	−66.7 (7)	S—C1'—C2'—C3'	171.3 (5)
O5—C1—C2—C3	61.7 (8)	C1'—C2'—O2'—C21'	116.8 (7)
S—C1—C2—C3	179.8 (5)	C3'—C2'—O2'—C21'	−124.7 (7)
C1—C2—O2—C21	102.4 (7)	C2'—O2'—C21'—O21'	0.5 (11)
C3—C2—O2—C21	−140.5 (6)	C2'—O2'—C21'—C22'	−179.8 (5)
C2—O2—C21—O21	−4.2 (10)	O2'—C2'—C3'—O3'	74.0 (7)
C2—O2—C21—C22	178.6 (5)	C1'—C2'—C3'—O3'	−169.7 (6)
O2—C2—C3—O3	74.8 (6)	O2'—C2'—C3'—C4'	−167.3 (6)
C1—C2—C3—O3	−167.3 (5)	C1'—C2'—C3'—C4'	−50.9 (8)
O2—C2—C3—C4	−169.2 (6)	C4'—C3'—O3'—C31'	106.8 (7)
C1—C2—C3—C4	−51.3 (8)	C2'—C3'—O3'—C31'	−132.3 (6)
C4—C3—O3—C31	92.6 (8)	C3'—O3'—C31'—O31'	−1.9 (12)
C2—C3—O3—C31	−149.2 (6)	C3'—O3'—C31'—C32'	179.4 (6)
C3—O3—C31—O31	1.6 (14)	O3'—C3'—C4'—O4'	−78.2 (7)
C3—O3—C31—C32	−178.5 (6)	C2'—C3'—C4'—O4'	166.2 (6)
O3—C3—C4—O4	−84.9 (7)	O3'—C3'—C4'—C5'	168.1 (6)
C2—C3—C4—O4	161.2 (5)	C2'—C3'—C4'—C5'	52.5 (9)
O3—C3—C4—C5	160.6 (6)	C3'—C4'—O4'—C41'	97.3 (8)
C2—C3—C4—C5	46.6 (9)	C5'—C4'—O4'—C41'	−148.0 (7)
C3—C4—O4—C41	108.4 (7)	C4'—O4'—C41'—O41'	5.1 (14)
C5—C4—O4—C41	−131.7 (6)	C4'—O4'—C41'—C42'	−177.9 (6)
C4—O4—C41—O41	−6.4 (13)	O4'—C4'—C5'—O5'	−174.7 (5)
C4—O4—C41—C42	177.7 (7)	C3'—C4'—C5'—O5'	−58.7 (8)
O4—C4—C5—O5	−170.6 (5)	O4'—C4'—C5'—C6'	66.4 (9)
C3—C4—C5—O5	−51.9 (8)	C3'—C4'—C5'—C6'	−177.6 (7)
O4—C4—C5—C6	69.4 (9)	O5'—C5'—C6'—O6'	65.5 (10)
C3—C4—C5—C6	−171.9 (7)	C4'—C5'—C6'—O6'	−174.5 (9)
O5—C5—C6—O6	−67.8 (7)	C5'—C6'—O6'—C61'	122.2 (13)
C4—C5—C6—O6	52.2 (9)	C6'—O6'—C61'—O61'	−6 (2)
C5—C6—O6—C61	178.2 (6)	C6'—O6'—C61'—C62'	−176.6 (9)
C6—O6—C61—O61	−1.3 (13)	C2'—C1'—O5'—C5'	−62.4 (9)
C6—O6—C61—C62	178.8 (7)	S—C1'—O5'—C5'	176.9 (6)
C2—C1—O5—C5	−71.6 (7)	C6'—C5'—O5'—C1'	−170.6 (7)
S—C1—O5—C5	167.1 (5)	C4'—C5'—O5'—C1'	67.1 (8)
C6—C5—O5—C1	−170.3 (6)	H1'—C1'—S—C1	2.7
C4—C5—O5—C1	66.0 (7)	H1—C1—S—C1'	52.7
C1—S—C1'—O5'	−117.2 (6)	H1'—C1'—C1—H1	51.6
C1—S—C1'—C2'	123.8 (5)