Bis(3-de­oxy-1,2-O-isopropyl­idene-α-d-glucofuranos-3-yl) disulfide

Luboradzki, R.; Pakulski, Z.

doi:10.1107/S1600536807035064

Bis(3-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-3-yl) disulfide

The title compound, C₁₈H₃₀O₁₀S₂, was prepared as a part of a project aimed at the synthesis of potential gelators of organic solvents. In the crystalline state, it forms hydrogen-bonded chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035064/at2343sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035064/at2343Isup2.hkl Contains datablock I

CCDC reference: 659097

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.029
wR factor = 0.066
Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.42 Ratio

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               5134
           Count of symmetry unique reflns         2923
           Completeness (_total/calc)            175.64%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2211
           Fraction of Friedel pairs measured     0.756
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
  13 ALERT level G = General alerts; check

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), was prepared as a part of a project aimed at the synthesis of potential gelators of organic solvents (Luboradzki et al., 2005). The class of saccharide-based gelators having free OH groups and the glucofuranose fragment are able to form gels with huge spectrum of organic solvents. According to the driving forces responsible for molecular aggregation they may be classified as hydrogen-bond-based gelators (Terech & Weiss 1997).

The crystal structure of (I) (Fig. 1) contains one independent molecule of the title compound per asymmetric unit. The molecules are bound into one dimensional hydrogen bond-based chains (generated by the screw axis along the a axis) utilizing all hydroxy H atoms (Fig. 2). Each molecule is involved in four hydrogen bonds as proton donor and in four as acceptor.

Related literature top

For low molecular weight?? organogelators see: Terech & Weiss (1997); Luboradzki et al. (2005). For related literature, see: Risbood et al. (1981).

Experimental top

The title compound (I) was prepared from 1,2-O-Isopropylidene-3-thio-α-D-glucofuranose by oxidation in hot methanol involving oxygen from the air. Subsequently it was recrystallized by cooling hot methanol solution.

Structure description top

For low molecular weight?? organogelators see: Terech & Weiss (1997); Luboradzki et al. (2005). For related literature, see: Risbood et al. (1981).

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as circles of arbitrary radii.
	Fig. 2. The packing of (I), viewed down the a axis, with the b axis vertical.

Bis(3-deoxy-1,2-O-isopropylidene-α-D-glucofuranos-3-yl) disulfide top

Crystal data top

C₁₈H₃₀O₁₀S₂	F(000) = 1000
M_r = 470.54	D_x = 1.385 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 17407 reflections
a = 8.7266 (1) Å	θ = 1.0–27.5°
b = 14.4778 (4) Å	µ = 0.29 mm⁻¹
c = 17.8606 (5) Å	T = 293 K
V = 2256.54 (9) Å³	Plate, colourless
Z = 4	0.4 × 0.2 × 0.1 mm

Data collection top

Nonius KappaCCD diffractometer	4969 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 2.6°
Detector resolution: 1242 (horizontal) x 1152 (vertical) pixels, CCD pixel size is 22.5 x 22.5 µm which gives at the imput a pixel of 110 x 110 µm (with 2 x 2 binning) pixels mm^-1	h = −11→11
189 frames via φ rotation (rotation angle 1.9°) and 2287 s per frame and 13 frames via ω rotation (rotation angle 1.9°) and 2287 s per frame scans	k = −18→18
22012 measured reflections	l = −23→23
5134 independent reflections

Refinement top

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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0134P)² + 1.4932P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
5134 reflections	Δρ_max = 0.21 e Å⁻³
279 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2211 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

Crystal data top

C₁₈H₃₀O₁₀S₂	V = 2256.54 (9) Å³
M_r = 470.54	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7266 (1) Å	µ = 0.29 mm⁻¹
b = 14.4778 (4) Å	T = 293 K
c = 17.8606 (5) Å	0.4 × 0.2 × 0.1 mm

Data collection top

Nonius KappaCCD diffractometer	4969 reflections with I > 2σ(I)
22012 measured reflections	R_int = 0.032
5134 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.066	Δρ_max = 0.21 e Å⁻³
S = 1.09	Δρ_min = −0.21 e Å⁻³
5134 reflections	Absolute structure: Flack (1983), 2211 Freidel pairs
279 parameters	Absolute structure parameter: 0.02 (5)
0 restraints

Special details top

Experimental. Synthesis of 1,2-O-Isopropylidene-3-thio-α-D-glucofuranose: To a suspension of LiAlH₄ (160 mg, 4.2 mM) in THF (25 ml) cooled in ice bath a solution of 5,6-di-O-acetyl-1,2-O-isopropylidene-3-thiocyanato-α-D-glucofuranose (Risbood et al.1981) (1, 629 mg, 1.8 mM) in THF (5 ml) was slowly added and stirred at room temp. for 3 h under an argon atmosphere. An excess of LiAlH₄ was decomposed by addition of ethyl acetate (1 ml), then the reaction mixture was cautiously acidified by addition of 5% aqueous NH₄Cl and solvents were evaporated to dryness. Column chromatography of the residue (hexane ? ethyl acetate, 5:1 than 1:1, then hexane ? ethyl acetate - methanol, 5:3:1) yielded 301 mg (70%) of the title compound as foam. [α]_D² -9.7 (c 1/2, chloroform ? methanol, 1:1); ¹H NMR (CD₃OD) δ: 5.86 (d, 1H, J_1,2 3.5 Hz, H-1), 4.66 (d, 1H, H-2), 4.18 (dd, 1H, J_4,3 3.7, J_4,5 9.4 Hz, H-4), 3.88 (m, 1H, H-5), 3.75 (dd, 1H, J_6,5 2.8, J_6,6? 11.6 Hz, H-6), 3.58 (dd, 1H, J_6?,5 5.7, H-6?), 3.48 (d, 1H, H-3), 3.31 (m, 1H, SH), 1.46 (s, 3H, CH₃), 1.29 (s, 3H, CH₃). ¹³C NMR (CD₃OD) δ: 112.9 (C), 106.0 (C-1), 88.7, 79.7, 71.8, 65.2 (C-6), 46.3 (C-3), 26.8 (CH₃), 26.4 (CH₃). HR—MS (ESI) calc. for C₉H₁₆NaO₅S [M+Na]+: 259.0611. Found: 259.0615.

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.06709 (5)	0.57977 (3)	0.73252 (2)	0.01991 (9)
S2	0.25277 (5)	0.54599 (3)	0.66943 (2)	0.01858 (9)
O1	−0.05475 (13)	0.73533 (8)	0.84580 (6)	0.0182 (2)
O2	0.13077 (14)	0.82781 (9)	0.90160 (7)	0.0221 (3)
O3	0.29050 (13)	0.80305 (8)	0.80408 (7)	0.0193 (3)
O4	−0.15521 (16)	0.76064 (10)	0.65014 (7)	0.0264 (3)
H4O	−0.2082	0.7303	0.6213	0.040*
O5	−0.45500 (14)	0.75117 (9)	0.71783 (7)	0.0227 (3)
H5O	−0.5321	0.7658	0.7413	0.034*
O6	0.35095 (14)	0.49495 (8)	0.50471 (7)	0.0197 (3)
O7	0.15464 (15)	0.42656 (10)	0.43354 (7)	0.0266 (3)
O8	0.00365 (14)	0.54097 (9)	0.48132 (7)	0.0230 (3)
O9	0.41651 (15)	0.72871 (8)	0.57326 (7)	0.0203 (3)
H9O	0.4679	0.7450	0.6094	0.030*
O10	0.72117 (14)	0.67699 (10)	0.52755 (7)	0.0254 (3)
H10O	0.7829	0.6932	0.4955	0.038*
C1	0.09359 (19)	0.73702 (12)	0.87676 (9)	0.0181 (3)
H1	0.1045	0.6917	0.9171	0.022*
C2	0.20792 (19)	0.71817 (12)	0.81233 (9)	0.0168 (3)
H2	0.2750	0.6653	0.8222	0.020*
C3	0.10501 (19)	0.70371 (11)	0.74457 (9)	0.0174 (3)
H3	0.1510	0.7302	0.6994	0.021*
C4	−0.03968 (19)	0.75640 (11)	0.76711 (9)	0.0162 (3)
H4	−0.0204	0.8227	0.7616	0.019*
C5	−0.18473 (19)	0.73217 (12)	0.72500 (9)	0.0179 (3)
H5A	−0.2013	0.6652	0.7265	0.022*
C6	−0.32189 (19)	0.78143 (12)	0.75760 (10)	0.0188 (3)
H6A	−0.3319	0.7670	0.8104	0.023*
H6B	−0.3098	0.8477	0.7524	0.023*
C7	0.2787 (2)	0.85227 (12)	0.87392 (10)	0.0204 (4)
C8	0.4020 (2)	0.82149 (14)	0.92836 (11)	0.0265 (4)
H8A	0.3869	0.8516	0.9757	0.040*
H8B	0.5009	0.8376	0.9088	0.040*
H8C	0.3961	0.7558	0.9351	0.040*
C9	0.2824 (2)	0.95448 (13)	0.85718 (12)	0.0284 (4)
H9A	0.2020	0.9695	0.8226	0.043*
H9B	0.3796	0.9704	0.8356	0.043*
H9C	0.2679	0.9886	0.9027	0.043*
C10	0.21131 (19)	0.44449 (12)	0.50562 (10)	0.0195 (3)
H10A	0.2237	0.3868	0.5336	0.023*
C11	0.0902 (2)	0.50586 (12)	0.54282 (9)	0.0189 (3)
H11A	0.0274	0.4729	0.5796	0.023*
C12	0.18450 (19)	0.58362 (12)	0.57694 (9)	0.0165 (3)
H12	0.1264	0.6414	0.5799	0.020*
C13	0.31752 (19)	0.59043 (11)	0.52161 (9)	0.0161 (3)
H13	0.2827	0.6217	0.4760	0.019*
C14	0.46207 (19)	0.63771 (11)	0.55074 (9)	0.0166 (3)
H14	0.5000	0.6040	0.5945	0.020*
C15	0.5868 (2)	0.64160 (12)	0.49218 (10)	0.0203 (3)
H15A	0.6063	0.5804	0.4723	0.024*
H15B	0.5562	0.6816	0.4512	0.024*
C16	0.0177 (2)	0.47929 (12)	0.41967 (10)	0.0207 (4)
C17	−0.1173 (2)	0.41418 (14)	0.41582 (11)	0.0288 (4)
H17A	−0.1226	0.3787	0.4611	0.043*
H17B	−0.1051	0.3734	0.3739	0.043*
H17C	−0.2100	0.4491	0.4100	0.043*
C18	0.0392 (3)	0.53557 (16)	0.34954 (12)	0.0432 (6)
H18A	−0.0497	0.5734	0.3414	0.065*
H18B	0.0531	0.4950	0.3076	0.065*
H18C	0.1278	0.5743	0.3549	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0209 (2)	0.01871 (19)	0.02014 (19)	−0.00514 (17)	0.00455 (17)	−0.00471 (16)
S2	0.01921 (19)	0.01991 (18)	0.01661 (18)	0.00203 (17)	0.00090 (17)	−0.00052 (15)
O1	0.0146 (6)	0.0254 (6)	0.0145 (5)	−0.0016 (5)	−0.0011 (4)	−0.0011 (5)
O2	0.0169 (6)	0.0228 (6)	0.0266 (7)	−0.0005 (5)	−0.0004 (5)	−0.0102 (5)
O3	0.0157 (6)	0.0193 (6)	0.0229 (6)	−0.0036 (5)	−0.0008 (5)	−0.0047 (5)
O4	0.0241 (7)	0.0420 (8)	0.0130 (6)	−0.0132 (6)	−0.0020 (5)	0.0002 (5)
O5	0.0147 (6)	0.0289 (7)	0.0246 (6)	−0.0020 (5)	−0.0027 (5)	−0.0026 (5)
O6	0.0168 (6)	0.0146 (5)	0.0276 (6)	−0.0005 (5)	0.0041 (5)	−0.0045 (5)
O7	0.0240 (7)	0.0302 (7)	0.0257 (7)	0.0022 (6)	−0.0003 (5)	−0.0131 (6)
O8	0.0238 (6)	0.0235 (6)	0.0219 (6)	0.0034 (5)	−0.0048 (5)	−0.0076 (5)
O9	0.0229 (6)	0.0144 (5)	0.0237 (6)	0.0017 (5)	−0.0047 (5)	−0.0030 (5)
O10	0.0185 (7)	0.0374 (8)	0.0202 (6)	−0.0108 (6)	0.0027 (5)	−0.0039 (6)
C1	0.0169 (8)	0.0196 (8)	0.0178 (7)	0.0002 (6)	−0.0029 (6)	−0.0016 (6)
C2	0.0140 (8)	0.0170 (8)	0.0196 (8)	−0.0006 (6)	−0.0017 (6)	−0.0019 (6)
C3	0.0174 (8)	0.0172 (8)	0.0176 (8)	−0.0029 (6)	0.0008 (6)	−0.0027 (6)
C4	0.0171 (8)	0.0179 (7)	0.0136 (7)	−0.0022 (6)	−0.0009 (6)	−0.0006 (6)
C5	0.0170 (8)	0.0213 (8)	0.0155 (7)	−0.0042 (6)	−0.0012 (6)	0.0003 (6)
C6	0.0177 (8)	0.0194 (8)	0.0193 (8)	−0.0012 (7)	−0.0051 (7)	−0.0008 (6)
C7	0.0162 (8)	0.0220 (9)	0.0229 (8)	0.0007 (7)	−0.0026 (7)	−0.0070 (7)
C8	0.0200 (9)	0.0303 (10)	0.0290 (10)	0.0039 (8)	−0.0069 (7)	−0.0084 (8)
C9	0.0235 (9)	0.0212 (8)	0.0406 (11)	−0.0007 (8)	−0.0030 (8)	−0.0072 (8)
C10	0.0209 (9)	0.0158 (8)	0.0219 (8)	−0.0023 (6)	0.0004 (6)	−0.0028 (6)
C11	0.0179 (8)	0.0205 (8)	0.0181 (8)	−0.0014 (7)	0.0004 (7)	−0.0032 (6)
C12	0.0176 (8)	0.0166 (7)	0.0155 (7)	0.0021 (6)	−0.0003 (6)	−0.0014 (6)
C13	0.0174 (8)	0.0125 (7)	0.0183 (8)	0.0010 (6)	0.0006 (6)	−0.0010 (6)
C14	0.0173 (8)	0.0151 (7)	0.0173 (7)	−0.0002 (6)	−0.0016 (6)	0.0009 (6)
C15	0.0199 (9)	0.0216 (8)	0.0194 (8)	−0.0043 (7)	0.0000 (7)	−0.0020 (7)
C16	0.0272 (9)	0.0192 (8)	0.0156 (8)	−0.0010 (7)	−0.0001 (7)	−0.0014 (6)
C17	0.0290 (10)	0.0252 (9)	0.0323 (10)	−0.0045 (8)	−0.0071 (8)	−0.0029 (8)
C18	0.0697 (17)	0.0351 (12)	0.0247 (10)	−0.0063 (12)	0.0037 (10)	0.0069 (9)

Geometric parameters (Å, º) top

S1—C3	1.8373 (17)	C5—H5A	0.9800
S1—S2	2.0335 (6)	C6—H6A	0.9700
S2—C12	1.8386 (17)	C6—H6B	0.9700
O1—C1	1.408 (2)	C7—C9	1.510 (3)
O1—C4	1.4442 (19)	C7—C8	1.517 (2)
O2—C1	1.425 (2)	C8—H8A	0.9600
O2—C7	1.427 (2)	C8—H8B	0.9600
O3—C2	1.432 (2)	C8—H8C	0.9600
O3—C7	1.440 (2)	C9—H9A	0.9600
O4—C5	1.423 (2)	C9—H9B	0.9600
O4—H4O	0.8200	C9—H9C	0.9600
O5—C6	1.430 (2)	C10—C11	1.533 (2)
O5—H5O	0.8200	C10—H10A	0.9800
O6—C10	1.421 (2)	C11—C12	1.522 (2)
O6—C13	1.4446 (19)	C11—H11A	0.9800
O7—C10	1.403 (2)	C12—C13	1.528 (2)
O7—C16	1.440 (2)	C12—H12	0.9800
O8—C16	1.423 (2)	C13—C14	1.527 (2)
O8—C11	1.426 (2)	C13—H13	0.9800
O9—C14	1.434 (2)	C14—C15	1.511 (2)
O9—H9O	0.8200	C14—H14	0.9800
O10—C15	1.427 (2)	C15—H15A	0.9700
O10—H10O	0.8200	C15—H15B	0.9700
C1—C2	1.547 (2)	C16—C18	1.506 (3)
C1—H1	0.9800	C16—C17	1.510 (3)
C2—C3	1.522 (2)	C17—H17A	0.9600
C2—H2	0.9800	C17—H17B	0.9600
C3—C4	1.529 (2)	C17—H17C	0.9600
C3—H3	0.9800	C18—H18A	0.9600
C4—C5	1.514 (2)	C18—H18B	0.9600
C4—H4	0.9800	C18—H18C	0.9600
C5—C6	1.510 (2)

C3—S1—S2	98.99 (6)	C7—C9—H9A	109.5
C12—S2—S1	99.69 (6)	C7—C9—H9B	109.5
C1—O1—C4	107.15 (12)	H9A—C9—H9B	109.5
C1—O2—C7	109.10 (13)	C7—C9—H9C	109.5
C2—O3—C7	107.43 (13)	H9A—C9—H9C	109.5
C5—O4—H4O	109.5	H9B—C9—H9C	109.5
C6—O5—H5O	109.5	O7—C10—O6	112.76 (14)
C10—O6—C13	108.45 (12)	O7—C10—C11	105.18 (14)
C10—O7—C16	110.64 (13)	O6—C10—C11	107.37 (13)
C16—O8—C11	109.08 (13)	O7—C10—H10A	110.5
C14—O9—H9O	109.5	O6—C10—H10A	110.5
C15—O10—H10O	109.5	C11—C10—H10A	110.5
O1—C1—O2	110.35 (13)	O8—C11—C12	109.33 (14)
O1—C1—C2	107.32 (13)	O8—C11—C10	103.76 (13)
O2—C1—C2	104.33 (13)	C12—C11—C10	103.25 (13)
O1—C1—H1	111.5	O8—C11—H11A	113.2
O2—C1—H1	111.5	C12—C11—H11A	113.2
C2—C1—H1	111.5	C10—C11—H11A	113.2
O3—C2—C3	109.47 (13)	C11—C12—C13	101.52 (13)
O3—C2—C1	104.45 (13)	C11—C12—S2	108.41 (12)
C3—C2—C1	103.61 (13)	C13—C12—S2	110.74 (11)
O3—C2—H2	112.9	C11—C12—H12	111.9
C3—C2—H2	112.9	C13—C12—H12	111.9
C1—C2—H2	112.9	S2—C12—H12	111.9
C2—C3—C4	102.08 (13)	O6—C13—C14	109.48 (13)
C2—C3—S1	109.50 (12)	O6—C13—C12	103.11 (13)
C4—C3—S1	111.67 (11)	C14—C13—C12	115.88 (14)
C2—C3—H3	111.1	O6—C13—H13	109.4
C4—C3—H3	111.1	C14—C13—H13	109.4
S1—C3—H3	111.1	C12—C13—H13	109.4
O1—C4—C5	111.01 (13)	O9—C14—C15	111.09 (14)
O1—C4—C3	103.07 (13)	O9—C14—C13	106.17 (13)
C5—C4—C3	116.36 (13)	C15—C14—C13	112.10 (14)
O1—C4—H4	108.7	O9—C14—H14	109.1
C5—C4—H4	108.7	C15—C14—H14	109.1
C3—C4—H4	108.7	C13—C14—H14	109.1
O4—C5—C6	111.65 (14)	O10—C15—C14	107.40 (13)
O4—C5—C4	104.38 (13)	O10—C15—H15A	110.2
C6—C5—C4	111.21 (14)	C14—C15—H15A	110.2
O4—C5—H5A	109.8	O10—C15—H15B	110.2
C6—C5—H5A	109.8	C14—C15—H15B	110.2
C4—C5—H5A	109.8	H15A—C15—H15B	108.5
O5—C6—C5	107.91 (13)	O8—C16—O7	105.71 (13)
O5—C6—H6A	110.1	O8—C16—C18	108.36 (15)
C5—C6—H6A	110.1	O7—C16—C18	109.05 (17)
O5—C6—H6B	110.1	O8—C16—C17	111.09 (15)
C5—C6—H6B	110.1	O7—C16—C17	108.93 (15)
H6A—C6—H6B	108.4	C18—C16—C17	113.40 (17)
O2—C7—O3	104.00 (13)	C16—C17—H17A	109.5
O2—C7—C9	109.33 (14)	C16—C17—H17B	109.5
O3—C7—C9	108.17 (15)	H17A—C17—H17B	109.5
O2—C7—C8	110.29 (15)	C16—C17—H17C	109.5
O3—C7—C8	111.04 (14)	H17A—C17—H17C	109.5
C9—C7—C8	113.56 (15)	H17B—C17—H17C	109.5
C7—C8—H8A	109.5	C16—C18—H18A	109.5
C7—C8—H8B	109.5	C16—C18—H18B	109.5
H8A—C8—H8B	109.5	H18A—C18—H18B	109.5
C7—C8—H8C	109.5	C16—C18—H18C	109.5
H8A—C8—H8C	109.5	H18A—C18—H18C	109.5
H8B—C8—H8C	109.5	H18B—C18—H18C	109.5

C3—S1—S2—C12	−81.01 (8)	C16—O7—C10—O6	−110.42 (15)
C4—O1—C1—O2	89.04 (15)	C16—O7—C10—C11	6.27 (18)
C4—O1—C1—C2	−24.05 (17)	C13—O6—C10—O7	101.54 (16)
C7—O2—C1—O1	−131.43 (14)	C13—O6—C10—C11	−13.84 (17)
C7—O2—C1—C2	−16.44 (17)	C16—O8—C11—C12	133.98 (14)
C7—O3—C2—C3	133.13 (14)	C16—O8—C11—C10	24.34 (17)
C7—O3—C2—C1	22.72 (16)	O7—C10—C11—O8	−18.43 (17)
O1—C1—C2—O3	113.11 (14)	O6—C10—C11—O8	101.89 (15)
O2—C1—C2—O3	−3.99 (16)	O7—C10—C11—C12	−132.51 (14)
O1—C1—C2—C3	−1.50 (17)	O6—C10—C11—C12	−12.19 (17)
O2—C1—C2—C3	−118.60 (14)	O8—C11—C12—C13	−78.46 (16)
O3—C2—C3—C4	−86.56 (15)	C10—C11—C12—C13	31.52 (16)
C1—C2—C3—C4	24.41 (16)	O8—C11—C12—S2	164.88 (11)
O3—C2—C3—S1	154.98 (11)	C10—C11—C12—S2	−85.14 (13)
C1—C2—C3—S1	−94.05 (13)	S1—S2—C12—C11	−84.82 (11)
S2—S1—C3—C2	−87.01 (11)	S1—S2—C12—C13	164.62 (10)
S2—S1—C3—C4	160.68 (10)	C10—O6—C13—C14	158.11 (13)
C1—O1—C4—C5	165.20 (13)	C10—O6—C13—C12	34.22 (16)
C1—O1—C4—C3	39.93 (15)	C11—C12—C13—O6	−40.33 (16)
C2—C3—C4—O1	−39.16 (15)	S2—C12—C13—O6	74.62 (14)
S1—C3—C4—O1	77.74 (13)	C11—C12—C13—C14	−159.90 (14)
C2—C3—C4—C5	−160.87 (14)	S2—C12—C13—C14	−44.95 (17)
S1—C3—C4—C5	−43.97 (17)	O6—C13—C14—O9	−174.31 (12)
O1—C4—C5—O4	177.28 (13)	C12—C13—C14—O9	−58.27 (18)
C3—C4—C5—O4	−65.29 (18)	O6—C13—C14—C15	64.22 (17)
O1—C4—C5—C6	56.74 (18)	C12—C13—C14—C15	−179.75 (14)
C3—C4—C5—C6	174.17 (14)	O9—C14—C15—O10	67.98 (18)
O4—C5—C6—O5	67.08 (17)	C13—C14—C15—O10	−173.41 (14)
C4—C5—C6—O5	−176.77 (13)	C11—O8—C16—O7	−20.99 (18)
C1—O2—C7—O3	30.63 (17)	C11—O8—C16—C18	−137.78 (17)
C1—O2—C7—C9	145.97 (15)	C11—O8—C16—C17	97.02 (17)
C1—O2—C7—C8	−88.49 (17)	C10—O7—C16—O8	8.42 (18)
C2—O3—C7—O2	−33.02 (16)	C10—O7—C16—C18	124.73 (17)
C2—O3—C7—C9	−149.18 (14)	C10—O7—C16—C17	−111.03 (16)
C2—O3—C7—C8	85.58 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O10ⁱ	0.82	1.94	2.7249 (18)	159
O5—H5O···O3ⁱ	0.82	1.99	2.8055 (18)	176
O9—H9O···O5ⁱⁱ	0.82	2.05	2.8338 (17)	159
O10—H10O···O9ⁱⁱⁱ	0.82	2.04	2.8305 (18)	163

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₃₀O₁₀S₂
M_r	470.54
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.7266 (1), 14.4778 (4), 17.8606 (5)
V (Å³)	2256.54 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.4 × 0.2 × 0.1

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22012, 5134, 4969
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.066, 1.09
No. of reflections	5134
No. of parameters	279
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21
Absolute structure	Flack (1983), 2211 Freidel pairs
Absolute structure parameter	0.02 (5)

Computer programs: COLLECT (Nonius, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).