3-Meth­oxy­methyl-16β,17β-epiestriol-16β,17β-diyl sulfate

Chen, J.-J.; Wang, H.-D.; Yao, C.

doi:10.1107/S1600536811039213

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2910

doi:10.1107/S1600536811039213

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3-Methoxymethyl-16β,17β-epiestriol-16β,17β-diyl sulfate

Jian-Jun Chen,^a Hai-Dong Wang ^a and Cheng Yao ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: yaocheng@njut.edu.cn

(Received 8 September 2011; accepted 24 September 2011; online 12 October 2011)

The title compound, C₂₀H₂₆O₆S, synthesized by the reaction of 3-O-methoxymethyl-16β-epiestriol and sulfonyldiimidazole, is composed of a 3-methoxymethyl group connected via two O atoms to a 16,17-O-sulfuryl-16-epiestriol group. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into [001] chains.

Related literature

We have used the title compound as a substrate for the production of F-18 16α-fluoroestradiol via nucleophilic fluorination, see: Romer et al. (1996 ). Fluorine-18 16α-fluoroestradiol is a valuable radiopharmaceutical for the investigation of the estrogen receptor status of primary and metastatic breast cancer, see: Lim et al. (1996 ); Romer et al. (1996). For bond-length data, see: Allen et al. (2002 ).

Experimental

Crystal data

C₂₀H₂₆O₆S
M_r = 394.47
Orthorhombic, P 2₁ 2₁ 2
a = 10.296 (2) Å
b = 23.503 (5) Å
c = 7.9060 (16) Å
V = 1913.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.942, T_max = 0.980
3875 measured reflections
3530 independent reflections
2174 reflections with I > 2σ(I)
R_int = 0.060
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.182
S = 1.00
3530 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1483 Friedel pairs
Flack parameter: 0.00 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20A⋯O3ⁱ	0.96	2.50	3.338 (5)	146
Symmetry code: (i) x, y, z-1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811039213/bq2303sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039213/bq2303Isup2.hkl

checkCIF report

Comment top

Fluorine-18 16alpha-fluoroestradiol has proven to be a valuable radiopharmaceuticalfor the investigation of the estrogen receptor status of primary and metastatic breast cancer. (Lim et al.,1996; Romer et al.,1996). We have prepared 3-methoxymethyl-16β,17β-epiestriol-O-cyclic sulfone and used it as a substrate for the production of F-18 16alpha-fluoroestradiol, via nucleophilic fluorination with fluoride ion. (Romer et al.,1996).

We report here the crystal structure of the titled compound, (I). The molecular strucutre of (I) is shown in Fig. 1. In this structure, ring A (S/O2/C3/C2/O1) and ring B (C1-C5) adopt twist conformation, the mean deviation from plane are 0.1171 Å and 0.1817 Å, respectively. Ring C (C4-C9) and ring D (C8-C13) are two twisty six-mermbered rings, the dihedral angles between the C7/C8/C9 and C5/C4/C6, C10/C11/C12 and C8/C9/C13 are 1.1 (1) ° and 43.3 (2) °, respectively. So it can be found that the ring C is a six-membered ring in its chair form. Ring E (C10/C11/C14-C17) is a planar six-mermbered ring and the mean deviation from plane is 0.0170 Å. In the crystal structure, intermolecular weak C—H···O hydrogen bond (Table 1) links the molecules to form a dimeric unit (Fig. 2), in which it may be effective in the stabilization of the structure.

Related literature top

We have used the title compound as a substrate for the production of F-18 16α-fluoroestradiol via nucleophilic fluorination, see: Romer et al. (1996). Fluorine-18 16α-fluoroestradiol is a valuable radiopharmaceutical for the investigation of the estrogen receptor status of primary and metastatic breast cancer, see: Lim et al. (1996); Romer et al. (1996). For bond-length data, see: Allen et al. (2002).

Experimental top

A mixture of 3-O-Methoxymethyl-l6β-Epiestriol (0.9 mmol) and sodium hydride (3.5 mmol) in anhydrous THF (10 ml) was stirred for 15 min. Added a solution of sulfonyldiimidazole (0.9 mmol) in THF slowly, then stirred for 1 h, filtered through celite and washed with EtOAc to give pure compound (I) (m.p. 425–426 K).(Lim et al.,1996). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo,1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Dashed lines indicate an intermolecular C—H···O hydrogen bond.

3-Methoxymethyl-16β,17β-epiestriol-16β,17β-diyl sulfate top

Crystal data top

C₂₀H₂₆O₆S	D_x = 1.370 Mg m⁻³
M_r = 394.47	Melting point = 425–426 K
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P22ab	Cell parameters from 25 reflections
a = 10.296 (2) Å	θ = 9–13°
b = 23.503 (5) Å	µ = 0.20 mm⁻¹
c = 7.9060 (16) Å	T = 293 K
V = 1913.1 (7) Å³	Needle, colorless
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 840

Data collection top

Enraf–Nonius CAD-4 diffractometer	2174 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 25.4°, θ_min = 1.7°
ω/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = −28→0
T_min = 0.942, T_max = 0.980	l = −9→0
3875 measured reflections	3 standard reflections every 200 reflections
3530 independent reflections	intensity decay: 1%

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)] = 0.064	H-atom parameters constrained
wR(F²) = 0.182	w = 1/[σ²(F_o²) + (0.1P)² + 0.2P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3530 reflections	Δρ_max = 0.22 e Å⁻³
244 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1483 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (18)

Crystal data top

C₂₀H₂₆O₆S	V = 1913.1 (7) Å³
M_r = 394.47	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 10.296 (2) Å	µ = 0.20 mm⁻¹
b = 23.503 (5) Å	T = 293 K
c = 7.9060 (16) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2174 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.060
T_min = 0.942, T_max = 0.980	3 standard reflections every 200 reflections
3875 measured reflections	intensity decay: 1%
3530 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.182	Δρ_max = 0.22 e Å⁻³
S = 1.00	Δρ_min = −0.17 e Å⁻³
3530 reflections	Absolute structure: Flack (1983), 1483 Friedel pairs
244 parameters	Absolute structure parameter: 0.00 (18)
0 restraints

Special details top

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
S	0.28012 (13)	0.68651 (6)	0.51055 (15)	0.0796 (4)
O1	0.3963 (3)	0.72326 (15)	0.4438 (4)	0.0812 (9)
C1	0.4281 (4)	0.8080 (2)	0.2704 (6)	0.0746 (12)
H1A	0.4782	0.7802	0.2075	0.089*
H1B	0.4854	0.8383	0.3078	0.089*
O2	0.1693 (3)	0.72213 (15)	0.4266 (4)	0.0780 (9)
C2	0.3582 (4)	0.7803 (2)	0.4211 (6)	0.0719 (12)
H2A	0.3711	0.8024	0.5248	0.086*
O3	0.2689 (5)	0.6907 (2)	0.6849 (4)	0.1299 (16)
C3	0.2124 (4)	0.7777 (2)	0.3724 (5)	0.0673 (11)
H3B	0.1636	0.8076	0.4311	0.081*
C4	0.2067 (4)	0.78685 (18)	0.1763 (5)	0.0635 (10)
O4	0.2839 (4)	0.63112 (14)	0.4338 (5)	0.1001 (11)
C5	0.3156 (4)	0.83170 (18)	0.1630 (6)	0.0606 (11)
H5A	0.2838	0.8655	0.2228	0.073*
O5	0.2892 (7)	0.9855 (3)	−0.7260 (7)	0.155 (2)
C6	0.0819 (4)	0.8112 (2)	0.1126 (7)	0.0864 (15)
H6A	0.0543	0.8420	0.1860	0.104*
H6B	0.0151	0.7821	0.1142	0.104*
O6	0.2753 (9)	1.0346 (3)	−0.9382 (11)	0.190 (3)
C7	0.0990 (5)	0.8339 (3)	−0.0709 (7)	0.0858 (15)
H7A	0.1155	0.8021	−0.1463	0.103*
H7B	0.0191	0.8521	−0.1069	0.103*
C8	0.2109 (5)	0.87663 (17)	−0.0848 (6)	0.0705 (11)
H8A	0.1902	0.9082	−0.0084	0.085*
C9	0.3391 (4)	0.85036 (18)	−0.0208 (6)	0.0670 (12)
H9A	0.3592	0.8167	−0.0891	0.080*
C10	0.2324 (6)	0.90293 (19)	−0.2624 (7)	0.0827 (14)
C11	0.3484 (7)	0.9168 (2)	−0.3227 (8)	0.0948 (18)
C12	0.4723 (6)	0.9051 (3)	−0.2252 (9)	0.1062 (19)
H12A	0.5160	0.8727	−0.2753	0.127*
H12B	0.5294	0.9377	−0.2354	0.127*
C13	0.4483 (5)	0.8932 (2)	−0.0402 (7)	0.0838 (15)
H13A	0.4254	0.9283	0.0173	0.101*
H13B	0.5268	0.8784	0.0112	0.101*
C14	0.1150 (8)	0.9149 (2)	−0.3591 (8)	0.104 (2)
H14A	0.0322	0.9047	−0.3235	0.124*
C15	0.1424 (10)	0.9461 (3)	−0.5261 (9)	0.126 (3)
H15A	0.0727	0.9564	−0.5945	0.151*
C16	0.2557 (12)	0.9581 (3)	−0.5736 (9)	0.120 (3)
C17	0.3595 (9)	0.9437 (2)	−0.4803 (8)	0.110 (2)
H17A	0.4420	0.9519	−0.5218	0.132*
C18	0.2327 (12)	1.0332 (4)	−0.7645 (12)	0.168 (4)
H18A	0.2656	1.0650	−0.6991	0.202*
H18B	0.1389	1.0312	−0.7543	0.202*
C19	0.1688 (12)	1.0446 (4)	−1.0307 (14)	0.196 (5)
H19A	0.1908	1.0437	−1.1487	0.294*
H19B	0.1342	1.0813	−1.0024	0.294*
H19C	0.1049	1.0159	−1.0073	0.294*
C20	0.2369 (5)	0.73070 (18)	0.0879 (5)	0.0754 (13)
H20A	0.2351	0.7362	−0.0324	0.113*
H20B	0.1732	0.7028	0.1191	0.113*
H20C	0.3216	0.7178	0.1213	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0769 (7)	0.1030 (9)	0.0588 (6)	−0.0014 (7)	−0.0024 (6)	−0.0010 (7)
O1	0.0633 (18)	0.096 (2)	0.084 (2)	0.0045 (17)	−0.0062 (16)	−0.0018 (19)
C1	0.054 (2)	0.077 (3)	0.093 (3)	−0.008 (2)	−0.003 (2)	−0.007 (3)
O2	0.0670 (18)	0.095 (2)	0.0718 (19)	−0.0097 (17)	−0.0016 (15)	0.0055 (18)
C2	0.068 (3)	0.079 (3)	0.069 (3)	0.007 (2)	−0.015 (2)	−0.025 (3)
O3	0.115 (3)	0.219 (5)	0.0553 (19)	0.021 (4)	0.010 (2)	−0.008 (2)
C3	0.059 (2)	0.084 (3)	0.058 (2)	0.014 (2)	0.008 (2)	−0.010 (2)
C4	0.045 (2)	0.081 (3)	0.065 (2)	−0.006 (2)	−0.0058 (19)	−0.018 (2)
O4	0.106 (3)	0.093 (2)	0.101 (3)	−0.003 (2)	0.002 (2)	−0.009 (2)
C5	0.056 (2)	0.054 (2)	0.072 (3)	−0.0070 (17)	−0.0050 (19)	−0.0186 (19)
O5	0.205 (6)	0.134 (4)	0.127 (4)	0.023 (4)	0.005 (4)	0.011 (3)
C6	0.053 (2)	0.100 (4)	0.106 (4)	−0.007 (3)	−0.005 (2)	−0.010 (3)
O6	0.175 (6)	0.205 (6)	0.192 (7)	−0.012 (6)	0.017 (6)	0.012 (5)
C7	0.065 (3)	0.106 (4)	0.085 (3)	−0.002 (3)	−0.012 (3)	0.008 (3)
C8	0.069 (2)	0.060 (2)	0.083 (3)	−0.009 (2)	−0.017 (3)	−0.014 (2)
C9	0.058 (2)	0.062 (2)	0.082 (3)	−0.0060 (18)	−0.002 (2)	−0.017 (2)
C10	0.110 (4)	0.055 (2)	0.083 (3)	0.001 (3)	0.005 (3)	−0.019 (2)
C11	0.121 (5)	0.058 (3)	0.106 (5)	−0.014 (3)	0.013 (4)	−0.009 (3)
C12	0.096 (4)	0.092 (4)	0.130 (5)	−0.024 (3)	0.013 (4)	−0.003 (4)
C13	0.083 (3)	0.066 (3)	0.103 (4)	−0.017 (2)	0.010 (3)	−0.006 (3)
C14	0.138 (5)	0.081 (4)	0.093 (4)	0.020 (4)	−0.023 (4)	−0.014 (3)
C15	0.181 (8)	0.108 (5)	0.089 (5)	0.051 (5)	−0.011 (5)	−0.028 (4)
C16	0.177 (8)	0.101 (5)	0.081 (4)	0.045 (5)	0.025 (5)	−0.007 (4)
C17	0.185 (7)	0.061 (3)	0.084 (4)	−0.018 (4)	0.031 (5)	−0.003 (3)
C18	0.219 (11)	0.135 (7)	0.151 (8)	−0.035 (8)	0.000 (8)	0.040 (6)
C19	0.188 (11)	0.188 (9)	0.213 (12)	0.032 (8)	−0.038 (9)	0.028 (9)
C20	0.104 (4)	0.065 (2)	0.058 (2)	−0.009 (3)	0.006 (2)	−0.011 (2)

Geometric parameters (Å, º) top

S—O3	1.387 (4)	C8—C9	1.542 (6)
S—O4	1.437 (4)	C8—C10	1.550 (7)
S—O2	1.563 (3)	C8—H8A	0.9800
S—O1	1.567 (3)	C9—C13	1.518 (6)
O1—C2	1.407 (6)	C9—H9A	0.9800
C1—C2	1.537 (7)	C10—C11	1.326 (8)
C1—C5	1.541 (6)	C10—C14	1.458 (8)
C1—H1A	0.9700	C11—C17	1.402 (8)
C1—H1B	0.9700	C11—C12	1.515 (9)
O2—C3	1.444 (6)	C12—C13	1.510 (8)
C2—C3	1.551 (6)	C12—H12A	0.9700
C2—H2A	0.9800	C12—H12B	0.9700
C3—C4	1.567 (6)	C13—H13A	0.9700
C3—H3B	0.9800	C13—H13B	0.9700
C4—C6	1.494 (6)	C14—C15	1.536 (10)
C4—C20	1.526 (6)	C14—H14A	0.9300
C4—C5	1.543 (5)	C15—C16	1.258 (11)
C5—C9	1.537 (6)	C15—H15A	0.9300
C5—H5A	0.9800	C16—C17	1.342 (11)
O5—C18	1.300 (10)	C17—H17A	0.9300
O5—C16	1.410 (9)	C18—H18A	0.9700
C6—C7	1.556 (7)	C18—H18B	0.9700
C6—H6A	0.9700	C19—H19A	0.9600
C6—H6B	0.9700	C19—H19B	0.9600
O6—C19	1.339 (11)	C19—H19C	0.9600
O6—C18	1.442 (10)	C20—H20A	0.9600
C7—C8	1.532 (6)	C20—H20B	0.9600
C7—H7A	0.9700	C20—H20C	0.9600
C7—H7B	0.9700

O3—S—O4	119.2 (3)	C9—C8—H8A	106.7
O3—S—O2	108.8 (3)	C10—C8—H8A	106.7
O4—S—O2	109.0 (2)	C13—C9—C5	113.7 (4)
O3—S—O1	111.0 (3)	C13—C9—C8	109.6 (4)
O4—S—O1	109.7 (2)	C5—C9—C8	106.9 (3)
O2—S—O1	96.84 (17)	C13—C9—H9A	108.9
C2—O1—S	110.8 (3)	C5—C9—H9A	108.9
C2—C1—C5	103.2 (3)	C8—C9—H9A	108.9
C2—C1—H1A	111.1	C11—C10—C14	120.7 (6)
C5—C1—H1A	111.1	C11—C10—C8	123.5 (5)
C2—C1—H1B	111.1	C14—C10—C8	115.7 (5)
C5—C1—H1B	111.1	C10—C11—C17	120.2 (7)
H1A—C1—H1B	109.1	C10—C11—C12	122.0 (6)
C3—O2—S	112.7 (3)	C17—C11—C12	117.7 (7)
O1—C2—C1	111.9 (4)	C13—C12—C11	112.9 (5)
O1—C2—C3	105.3 (4)	C13—C12—H12A	109.0
C1—C2—C3	106.1 (4)	C11—C12—H12A	109.0
O1—C2—H2A	111.1	C13—C12—H12B	109.0
C1—C2—H2A	111.1	C11—C12—H12B	109.0
C3—C2—H2A	111.1	H12A—C12—H12B	107.8
O2—C3—C2	105.0 (4)	C12—C13—C9	110.0 (4)
O2—C3—C4	114.0 (4)	C12—C13—H13A	109.7
C2—C3—C4	106.0 (4)	C9—C13—H13A	109.7
O2—C3—H3B	110.5	C12—C13—H13B	109.7
C2—C3—H3B	110.5	C9—C13—H13B	109.7
C4—C3—H3B	110.5	H13A—C13—H13B	108.2
C6—C4—C20	110.6 (4)	C10—C14—C15	113.0 (7)
C6—C4—C5	109.9 (4)	C10—C14—H14A	123.5
C20—C4—C5	114.3 (4)	C15—C14—H14A	123.5
C6—C4—C3	114.7 (4)	C16—C15—C14	122.2 (8)
C20—C4—C3	109.1 (4)	C16—C15—H15A	118.9
C5—C4—C3	97.7 (3)	C14—C15—H15A	118.9
C9—C5—C1	120.4 (4)	C15—C16—C17	121.2 (8)
C9—C5—C4	111.9 (3)	C15—C16—O5	125.8 (10)
C1—C5—C4	105.2 (3)	C17—C16—O5	112.9 (9)
C9—C5—H5A	106.1	C16—C17—C11	122.5 (8)
C1—C5—H5A	106.1	C16—C17—H17A	118.8
C4—C5—H5A	106.1	C11—C17—H17A	118.8
C18—O5—C16	119.0 (8)	O5—C18—O6	96.1 (10)
C4—C6—C7	110.4 (4)	O5—C18—H18A	112.5
C4—C6—H6A	109.6	O6—C18—H18A	112.5
C7—C6—H6A	109.6	O5—C18—H18B	112.5
C4—C6—H6B	109.6	O6—C18—H18B	112.5
C7—C6—H6B	109.6	H18A—C18—H18B	110.1
H6A—C6—H6B	108.1	O6—C19—H19A	109.5
C19—O6—C18	106.0 (9)	O6—C19—H19B	109.5
C8—C7—C6	112.2 (4)	H19A—C19—H19B	109.5
C8—C7—H7A	109.2	O6—C19—H19C	109.5
C6—C7—H7A	109.2	H19A—C19—H19C	109.5
C8—C7—H7B	109.2	H19B—C19—H19C	109.5
C6—C7—H7B	109.2	C4—C20—H20A	109.5
H7A—C7—H7B	107.9	C4—C20—H20B	109.5
C7—C8—C9	110.9 (4)	H20A—C20—H20B	109.5
C7—C8—C10	115.7 (4)	C4—C20—H20C	109.5
C9—C8—C10	109.6 (4)	H20A—C20—H20C	109.5
C7—C8—H8A	106.7	H20B—C20—H20C	109.5

O3—S—O1—C2	−84.0 (4)	C6—C7—C8—C10	−178.2 (4)
O4—S—O1—C2	142.3 (3)	C1—C5—C9—C13	−54.0 (5)
O2—S—O1—C2	29.3 (3)	C4—C5—C9—C13	−178.3 (4)
O3—S—O2—C3	98.6 (4)	C1—C5—C9—C8	−175.0 (3)
O4—S—O2—C3	−129.9 (3)	C4—C5—C9—C8	60.7 (4)
O1—S—O2—C3	−16.4 (3)	C7—C8—C9—C13	178.7 (4)
S—O1—C2—C1	−146.1 (3)	C10—C8—C9—C13	49.7 (5)
S—O1—C2—C3	−31.3 (4)	C7—C8—C9—C5	−57.8 (4)
C5—C1—C2—O1	126.6 (4)	C10—C8—C9—C5	173.3 (3)
C5—C1—C2—C3	12.3 (4)	C7—C8—C10—C11	−146.2 (5)
S—O2—C3—C2	0.0 (4)	C9—C8—C10—C11	−19.9 (6)
S—O2—C3—C4	115.6 (3)	C7—C8—C10—C14	37.1 (6)
O1—C2—C3—O2	18.9 (4)	C9—C8—C10—C14	163.4 (4)
C1—C2—C3—O2	137.6 (4)	C14—C10—C11—C17	0.6 (7)
O1—C2—C3—C4	−102.1 (4)	C8—C10—C11—C17	−176.0 (4)
C1—C2—C3—C4	16.6 (5)	C14—C10—C11—C12	179.8 (5)
O2—C3—C4—C6	90.8 (5)	C8—C10—C11—C12	3.3 (8)
C2—C3—C4—C6	−154.2 (4)	C10—C11—C12—C13	−16.9 (8)
O2—C3—C4—C20	−33.9 (5)	C17—C11—C12—C13	162.4 (4)
C2—C3—C4—C20	81.1 (5)	C11—C12—C13—C9	47.5 (6)
O2—C3—C4—C5	−153.0 (4)	C5—C9—C13—C12	175.0 (4)
C2—C3—C4—C5	−38.0 (4)	C8—C9—C13—C12	−65.5 (5)
C2—C1—C5—C9	−165.2 (4)	C11—C10—C14—C15	−2.4 (7)
C2—C1—C5—C4	−37.7 (4)	C8—C10—C14—C15	174.5 (4)
C6—C4—C5—C9	−61.2 (5)	C10—C14—C15—C16	1.9 (9)
C20—C4—C5—C9	63.9 (5)	C14—C15—C16—C17	0.5 (12)
C3—C4—C5—C9	178.9 (3)	C14—C15—C16—O5	178.7 (5)
C6—C4—C5—C1	166.4 (4)	C18—O5—C16—C15	52.1 (13)
C20—C4—C5—C1	−68.6 (4)	C18—O5—C16—C17	−129.6 (9)
C3—C4—C5—C1	46.5 (4)	C15—C16—C17—C11	−2.7 (11)
C20—C4—C6—C7	−71.7 (5)	O5—C16—C17—C11	179.0 (5)
C5—C4—C6—C7	55.5 (5)	C10—C11—C17—C16	2.1 (8)
C3—C4—C6—C7	164.4 (4)	C12—C11—C17—C16	−177.2 (6)
C4—C6—C7—C8	−54.6 (6)	C16—O5—C18—O6	−167.1 (8)
C6—C7—C8—C9	56.2 (6)	C19—O6—C18—O5	130.1 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O3ⁱ	0.96	2.50	3.338 (5)	146

Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆O₆S
M_r	394.47
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	293
a, b, c (Å)	10.296 (2), 23.503 (5), 7.9060 (16)
V (Å³)	1913.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.942, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	3875, 3530, 2174
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.182, 1.00
No. of reflections	3530
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17
Absolute structure	Flack (1983), 1483 Friedel pairs
Absolute structure parameter	0.00 (18)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O3ⁱ	0.96	2.50	3.338 (5)	146

Symmetry code: (i) x, y, z−1.

Acknowledgements

The authors would like to thank Professor Hua-qin Wang of Nanjing University for carrying out the X-ray crystallographic analysis.

References

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Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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