4α,6α-Dihy­droxy-1β-methyl­sulfonyl-8α,9α-ep­oxy-2β,12-epoxymethano-β-dihydro­agarofuran

Zhang, J.; Gao, P.; Li, L.; Wu, W.

doi:10.1107/S1600536811034179

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2496

doi:10.1107/S1600536811034179

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4α,6α-Dihydroxy-1β-methylsulfonyl-8α,9α-epoxy-2β,12-epoxymethano-β-dihydroagarofuran

Jiwen Zhang,^a Peng Gao,^b Longbo Li ^b and Wenjun Wu ^a ^*

^aInstitute of Pesticide Science and College of Sciences, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
^*Correspondence e-mail: nwzjw@yahoo.com.cn

(Received 15 August 2011; accepted 20 August 2011; online 27 August 2011)

The title molecule, C₁₆H₂₄O₈S, is a dihydroagrofuran derivative and has a heteropolycyclic structure. One cyclohexane ring exhibits a chair conformation and the other a non-chair conformation. In the crystal structure there is an intermolecular C—H⋯O hydrogen-bonding interaction to stabilize the packing.

Related literature

For general background, see: Gao et al. (2007 ); Spivey et al. (2002 ).

Experimental

Crystal data

C₁₆H₂₄O₈S
M_r = 376.41
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.530 (3) Å
b = 10.228 (3) Å
c = 17.424 (5) Å
V = 1698.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.25 × 0.22 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.944, T_max = 0.953
8175 measured reflections
3151 independent reflections
2633 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.085
S = 1.06
3151 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1325 Friedel pairs
Flack parameter: 0.13 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O2ⁱ	0.96	2.32	3.218 (4)	156
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034179/qm2023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034179/qm2023Isup2.hkl

checkCIF report

Comment top

Dihydroagrofuran esters and their derivatives have been widely explored as insecticidal medicine (Gao et al. 2007; Spivey et al. 2002). As a result of our program of screening insecticidal activity constituents from plants of China, some insecticidal β-dihydroagrofuran sesquiterpene polyol esters were isolated from the root bark of Chinese bittersweet, Celastrus angulatus Max. In order to find a new synthetic insecticide, the /b-dihydroagrofuran sesquiterpene polyol ester was optimized as a lead compound and we obtained an intermediate compound C₁₆H₂₄O₈S (I) and the synthesis and structure are reported here.

The title compound has a hetero-polycyclic structure. The 6-membering ring (C1–C6) exhibits a chair conformation. However, the other 6-membering ring (C1, C6–C10) exhibits neither a chair nor a boat conformation. The five atoms C1, C6, C8, C9 and C10 lie approximately in a plane, and the distance from C7 to the plane is 0.929 (3) Å.

The molecules of I crystalized in the P2₁2₁2₁ space group. In the crystal structure there is an intermolecular C—H···O hydrogen-bonding interaction (Table 1), which is helpful to the stabilization of the packing. Symmetry code: x, 1+y, z.

Related literature top

For general background, see: Gao et al. (2007); Spivey et al. (2002).

Experimental top

A mixture of dihydroagarofuran (3.34 g, 10 mmol) and methanesulfonyl chloride (3.5 mL, 44 mmol) in dry Pyridine (20 mL) was stirred over night at room temperature. When the reaction was completed, 2 mL methol was added to the reaction mixture to quench the reaction, then 50 mL water was added to the mixture and it was extracted with ethyl acetate. The ethyl acetate layer was washed with 50 mL of water, 15 mL of saturated sodium chloride and dried over anhydrous sodium sulfate and was separated on a silica gel column chromatography with a gradient of petroleum ether and ethyl acetate as eluent to yield 1.87 g of the title compound. The compound was then dissolved in THF, and colorless crystals were formed on slow evaporation at room temperature over one week.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

4α,6α-Dihydroxy-1β-methylsulfonyl-8α,9α-epoxy-2β,12-epoxymethano- β-dihydroagarofuran top

Crystal data top

C₁₆H₂₄O₈S	F(000) = 800
M_r = 376.41	D_x = 1.472 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2687 reflections
a = 9.530 (3) Å	θ = 2.3–22.5°
b = 10.228 (3) Å	µ = 0.23 mm⁻¹
c = 17.424 (5) Å	T = 296 K
V = 1698.3 (9) Å³	Block, colorless
Z = 4	0.25 × 0.22 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	3151 independent reflections
Radiation source: fine-focus sealed tube	2633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→7
T_min = 0.944, T_max = 0.953	k = −12→12
8175 measured reflections	l = −21→20

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0384P)² + 0.135P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3151 reflections	Δρ_max = 0.19 e Å⁻³
232 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1325 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.13 (9)

Crystal data top

C₁₆H₂₄O₈S	V = 1698.3 (9) Å³
M_r = 376.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.530 (3) Å	µ = 0.23 mm⁻¹
b = 10.228 (3) Å	T = 296 K
c = 17.424 (5) Å	0.25 × 0.22 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	3151 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2633 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.953	R_int = 0.034
8175 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.085	Δρ_max = 0.19 e Å⁻³
S = 1.06	Δρ_min = −0.20 e Å⁻³
3151 reflections	Absolute structure: Flack (1983), 1325 Friedel pairs
232 parameters	Absolute structure parameter: 0.13 (9)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.8202 (3)	0.4554 (2)	0.91912 (13)	0.0328 (6)
C2	0.9087 (3)	0.5765 (2)	0.90120 (14)	0.0346 (6)
H2	0.8965	0.6079	0.8485	0.042*
C3	1.0539 (3)	0.5224 (3)	0.91630 (14)	0.0426 (7)
H3	1.1223	0.5932	0.9220	0.051*
C4	1.0957 (3)	0.4311 (3)	0.85095 (16)	0.0463 (7)
H4A	1.1915	0.4021	0.8590	0.056*
H4B	1.0930	0.4793	0.8030	0.056*
C5	1.0002 (3)	0.3113 (3)	0.84427 (14)	0.0390 (6)
C6	0.8443 (3)	0.3563 (2)	0.85189 (13)	0.0303 (6)
C7	0.7308 (3)	0.2501 (3)	0.85700 (16)	0.0423 (7)
H7	0.7108	0.2316	0.9111	0.051*
C8	0.6076 (3)	0.3248 (3)	0.82229 (14)	0.0422 (7)
H8	0.5317	0.2652	0.8077	0.051*
C9	0.5590 (3)	0.4210 (3)	0.88392 (16)	0.0444 (7)
H9	0.4683	0.4023	0.9081	0.053*
C10	0.6664 (3)	0.4827 (2)	0.93331 (15)	0.0388 (6)
H10	0.6393	0.4986	0.9867	0.047*
C11	0.8932 (3)	0.4131 (3)	0.99432 (15)	0.0477 (7)
H11A	0.8498	0.4555	1.0381	0.057*
H11B	0.8863	0.3192	1.0010	0.057*
C12	0.6735 (3)	0.3883 (3)	0.75151 (14)	0.0382 (6)
C13	0.6056 (3)	0.5133 (3)	0.72187 (17)	0.0538 (8)
H13A	0.6224	0.5830	0.7576	0.081*
H13B	0.5063	0.5000	0.7164	0.081*
H13C	0.6452	0.5356	0.6729	0.081*
C14	0.6857 (3)	0.2946 (3)	0.68275 (15)	0.0531 (8)
H14A	0.7452	0.3329	0.6444	0.080*
H14B	0.5943	0.2793	0.6615	0.080*
H14C	0.7254	0.2132	0.6995	0.080*
C15	1.0454 (4)	0.2017 (3)	0.89920 (18)	0.0582 (9)
H15A	0.9702	0.1399	0.9047	0.087*
H15B	1.0677	0.2384	0.9484	0.087*
H15C	1.1266	0.1582	0.8788	0.087*
C16	0.7165 (3)	0.8404 (3)	0.88369 (19)	0.0586 (8)
H16A	0.6393	0.8104	0.9143	0.088*
H16B	0.7223	0.7891	0.8377	0.088*
H16C	0.7025	0.9306	0.8705	0.088*
O1	1.0156 (2)	0.2516 (2)	0.76988 (11)	0.0515 (5)
H1	0.9832	0.3003	0.7370	0.077*
O2	0.7634 (3)	0.13165 (18)	0.81877 (13)	0.0598 (6)
H2A	0.8383	0.1396	0.7961	0.090*
O3	1.0372 (2)	0.4519 (2)	0.98764 (10)	0.0540 (6)
O4	0.59795 (19)	0.56021 (18)	0.87714 (11)	0.0489 (5)
O5	0.81435 (16)	0.42256 (15)	0.77981 (8)	0.0310 (4)
O6	0.87426 (18)	0.67549 (17)	0.95895 (9)	0.0407 (4)
O7	0.9879 (2)	0.85121 (19)	0.88633 (12)	0.0590 (6)
O8	0.8610 (2)	0.89333 (19)	1.00595 (11)	0.0558 (5)
S1	0.87153 (7)	0.82442 (6)	0.93543 (4)	0.04001 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0404 (14)	0.0302 (13)	0.0278 (13)	−0.0028 (12)	0.0013 (11)	0.0036 (11)
C2	0.0408 (15)	0.0339 (14)	0.0293 (12)	−0.0035 (12)	−0.0021 (11)	−0.0016 (12)
C3	0.0402 (16)	0.0470 (17)	0.0406 (15)	−0.0038 (14)	−0.0085 (12)	0.0057 (14)
C4	0.0324 (15)	0.0525 (19)	0.0539 (17)	0.0080 (14)	−0.0023 (13)	0.0076 (15)
C5	0.0423 (15)	0.0369 (15)	0.0378 (14)	0.0094 (14)	−0.0046 (12)	0.0021 (13)
C6	0.0372 (15)	0.0265 (13)	0.0273 (12)	0.0023 (11)	−0.0007 (11)	0.0044 (10)
C7	0.0555 (17)	0.0296 (14)	0.0418 (16)	−0.0075 (14)	0.0082 (14)	−0.0024 (13)
C8	0.0367 (15)	0.0397 (16)	0.0502 (15)	−0.0110 (14)	0.0013 (12)	−0.0043 (14)
C9	0.0360 (14)	0.0453 (17)	0.0518 (16)	−0.0074 (13)	0.0099 (13)	−0.0013 (14)
C10	0.0430 (16)	0.0378 (15)	0.0355 (13)	−0.0011 (12)	0.0092 (13)	0.0052 (13)
C11	0.0603 (19)	0.0474 (17)	0.0353 (14)	0.0002 (15)	−0.0053 (14)	0.0032 (13)
C12	0.0309 (14)	0.0440 (17)	0.0396 (15)	−0.0021 (13)	−0.0042 (12)	−0.0073 (12)
C13	0.0502 (19)	0.064 (2)	0.0476 (16)	0.0101 (16)	−0.0130 (15)	0.0021 (16)
C14	0.0508 (17)	0.062 (2)	0.0463 (17)	−0.0026 (16)	−0.0084 (14)	−0.0189 (15)
C15	0.065 (2)	0.0468 (19)	0.063 (2)	0.0182 (16)	−0.0101 (16)	0.0088 (17)
C16	0.061 (2)	0.0390 (18)	0.076 (2)	−0.0010 (16)	−0.0203 (16)	0.0003 (17)
O1	0.0583 (13)	0.0482 (13)	0.0481 (12)	0.0175 (11)	0.0052 (11)	−0.0063 (10)
O2	0.0803 (16)	0.0256 (10)	0.0734 (15)	−0.0025 (11)	0.0017 (12)	−0.0087 (10)
O3	0.0535 (13)	0.0666 (14)	0.0420 (11)	0.0020 (11)	−0.0171 (10)	0.0074 (11)
O4	0.0431 (11)	0.0423 (12)	0.0614 (12)	0.0022 (10)	0.0045 (9)	0.0029 (10)
O5	0.0323 (9)	0.0312 (9)	0.0294 (8)	−0.0006 (8)	−0.0029 (7)	0.0035 (8)
O6	0.0544 (11)	0.0357 (10)	0.0318 (9)	−0.0046 (10)	−0.0022 (8)	−0.0062 (8)
O7	0.0615 (13)	0.0448 (13)	0.0707 (13)	−0.0125 (11)	0.0216 (11)	−0.0122 (11)
O8	0.0592 (13)	0.0517 (12)	0.0565 (12)	−0.0056 (11)	−0.0002 (11)	−0.0267 (10)
S1	0.0402 (4)	0.0345 (4)	0.0453 (4)	−0.0067 (3)	0.0010 (3)	−0.0108 (3)

Geometric parameters (Å, º) top

C1—C10	1.512 (3)	C10—O4	1.419 (3)
C1—C2	1.531 (4)	C10—H10	0.9800
C1—C11	1.545 (3)	C11—O3	1.433 (3)
C1—C6	1.566 (3)	C11—H11A	0.9700
C2—O6	1.465 (3)	C11—H11B	0.9700
C2—C3	1.513 (4)	C12—O5	1.472 (3)
C2—H2	0.9800	C12—C13	1.523 (4)
C3—O3	1.446 (3)	C12—C14	1.538 (4)
C3—C4	1.525 (4)	C13—H13A	0.9600
C3—H3	0.9800	C13—H13B	0.9600
C4—C5	1.531 (4)	C13—H13C	0.9600
C4—H4A	0.9700	C14—H14A	0.9600
C4—H4B	0.9700	C14—H14B	0.9600
C5—O1	1.440 (3)	C14—H14C	0.9600
C5—C15	1.536 (4)	C15—H15A	0.9600
C5—C6	1.561 (3)	C15—H15B	0.9600
C6—O5	1.455 (3)	C15—H15C	0.9600
C6—C7	1.535 (4)	C16—S1	1.738 (3)
C7—O2	1.417 (3)	C16—H16A	0.9600
C7—C8	1.526 (4)	C16—H16B	0.9600
C7—H7	0.9800	C16—H16C	0.9600
C8—C9	1.528 (4)	O1—H1	0.8200
C8—C12	1.529 (4)	O2—H2A	0.8200
C8—H8	0.9800	O6—S1	1.5777 (19)
C9—O4	1.476 (3)	O7—S1	1.427 (2)
C9—C10	1.478 (4)	O8—S1	1.4201 (18)
C9—H9	0.9800

C10—C1—C2	114.7 (2)	O4—C10—C9	61.24 (17)
C10—C1—C11	110.5 (2)	O4—C10—C1	115.9 (2)
C2—C1—C11	98.7 (2)	C9—C10—C1	119.8 (2)
C10—C1—C6	112.6 (2)	O4—C10—H10	116.2
C2—C1—C6	106.88 (19)	C9—C10—H10	116.2
C11—C1—C6	112.8 (2)	C1—C10—H10	116.2
O6—C2—C3	109.8 (2)	O3—C11—C1	106.6 (2)
O6—C2—C1	107.20 (19)	O3—C11—H11A	110.4
C3—C2—C1	99.9 (2)	C1—C11—H11A	110.4
O6—C2—H2	113.0	O3—C11—H11B	110.4
C3—C2—H2	113.0	C1—C11—H11B	110.4
C1—C2—H2	113.0	H11A—C11—H11B	108.6
O3—C3—C2	103.4 (2)	O5—C12—C13	107.5 (2)
O3—C3—C4	111.4 (2)	O5—C12—C8	101.85 (19)
C2—C3—C4	109.5 (2)	C13—C12—C8	117.1 (2)
O3—C3—H3	110.8	O5—C12—C14	109.9 (2)
C2—C3—H3	110.8	C13—C12—C14	106.9 (2)
C4—C3—H3	110.8	C8—C12—C14	113.3 (2)
C3—C4—C5	113.0 (2)	C12—C13—H13A	109.5
C3—C4—H4A	109.0	C12—C13—H13B	109.5
C5—C4—H4A	109.0	H13A—C13—H13B	109.5
C3—C4—H4B	109.0	C12—C13—H13C	109.5
C5—C4—H4B	109.0	H13A—C13—H13C	109.5
H4A—C4—H4B	107.8	H13B—C13—H13C	109.5
O1—C5—C4	110.3 (2)	C12—C14—H14A	109.5
O1—C5—C15	102.9 (2)	C12—C14—H14B	109.5
C4—C5—C15	111.7 (2)	H14A—C14—H14B	109.5
O1—C5—C6	107.38 (19)	C12—C14—H14C	109.5
C4—C5—C6	108.9 (2)	H14A—C14—H14C	109.5
C15—C5—C6	115.4 (2)	H14B—C14—H14C	109.5
O5—C6—C7	103.96 (19)	C5—C15—H15A	109.5
O5—C6—C5	104.51 (18)	C5—C15—H15B	109.5
C7—C6—C5	117.8 (2)	H15A—C15—H15B	109.5
O5—C6—C1	108.37 (17)	C5—C15—H15C	109.5
C7—C6—C1	108.1 (2)	H15A—C15—H15C	109.5
C5—C6—C1	113.21 (19)	H15B—C15—H15C	109.5
O2—C7—C8	114.2 (2)	S1—C16—H16A	109.5
O2—C7—C6	115.0 (2)	S1—C16—H16B	109.5
C8—C7—C6	99.5 (2)	H16A—C16—H16B	109.5
O2—C7—H7	109.2	S1—C16—H16C	109.5
C8—C7—H7	109.2	H16A—C16—H16C	109.5
C6—C7—H7	109.2	H16B—C16—H16C	109.5
C7—C8—C9	106.1 (2)	C5—O1—H1	109.5
C7—C8—C12	102.5 (2)	C7—O2—H2A	109.5
C9—C8—C12	114.7 (2)	C11—O3—C3	108.27 (19)
C7—C8—H8	111.0	C10—O4—C9	61.38 (17)
C9—C8—H8	111.0	C6—O5—C12	110.91 (17)
C12—C8—H8	111.0	C2—O6—S1	119.51 (14)
O4—C9—C10	57.38 (16)	O8—S1—O7	118.56 (12)
O4—C9—C8	119.2 (2)	O8—S1—O6	104.81 (11)
C10—C9—C8	118.3 (2)	O7—S1—O6	109.17 (11)
O4—C9—H9	116.3	O8—S1—C16	110.00 (15)
C10—C9—H9	116.3	O7—S1—C16	109.34 (14)
C8—C9—H9	116.3	O6—S1—C16	103.88 (12)

C10—C1—C2—O6	48.0 (3)	O2—C7—C8—C12	−77.3 (3)
C11—C1—C2—O6	−69.4 (2)	C6—C7—C8—C12	45.7 (2)
C6—C1—C2—O6	173.55 (17)	C7—C8—C9—O4	102.8 (3)
C10—C1—C2—C3	162.4 (2)	C12—C8—C9—O4	−9.5 (3)
C11—C1—C2—C3	45.1 (2)	C7—C8—C9—C10	36.4 (3)
C6—C1—C2—C3	−72.0 (2)	C12—C8—C9—C10	−76.0 (3)
O6—C2—C3—O3	67.6 (2)	C8—C9—C10—O4	108.3 (3)
C1—C2—C3—O3	−44.9 (2)	O4—C9—C10—C1	−105.0 (3)
O6—C2—C3—C4	−173.6 (2)	C8—C9—C10—C1	3.3 (4)
C1—C2—C3—C4	74.0 (2)	C2—C1—C10—O4	50.3 (3)
O3—C3—C4—C5	50.7 (3)	C11—C1—C10—O4	160.8 (2)
C2—C3—C4—C5	−63.0 (3)	C6—C1—C10—O4	−72.2 (3)
C3—C4—C5—O1	162.3 (2)	C2—C1—C10—C9	120.5 (3)
C3—C4—C5—C15	−84.0 (3)	C11—C1—C10—C9	−129.0 (3)
C3—C4—C5—C6	44.7 (3)	C6—C1—C10—C9	−2.0 (3)
O1—C5—C6—O5	−46.7 (2)	C10—C1—C11—O3	−151.7 (2)
C4—C5—C6—O5	72.7 (2)	C2—C1—C11—O3	−31.1 (3)
C15—C5—C6—O5	−160.7 (2)	C6—C1—C11—O3	81.4 (3)
O1—C5—C6—C7	68.1 (3)	C7—C8—C12—O5	−37.4 (2)
C4—C5—C6—C7	−172.5 (2)	C9—C8—C12—O5	77.1 (2)
C15—C5—C6—C7	−46.0 (3)	C7—C8—C12—C13	−154.3 (2)
O1—C5—C6—C1	−164.40 (19)	C9—C8—C12—C13	−39.8 (3)
C4—C5—C6—C1	−45.0 (3)	C7—C8—C12—C14	80.6 (2)
C15—C5—C6—C1	81.6 (3)	C9—C8—C12—C14	−165.0 (2)
C10—C1—C6—O5	73.0 (2)	C1—C11—O3—C3	3.9 (3)
C2—C1—C6—O5	−53.8 (2)	C2—C3—O3—C11	25.7 (3)
C11—C1—C6—O5	−161.2 (2)	C4—C3—O3—C11	−91.7 (3)
C10—C1—C6—C7	−39.1 (3)	C1—C10—O4—C9	111.3 (3)
C2—C1—C6—C7	−165.9 (2)	C8—C9—O4—C10	−106.7 (3)
C11—C1—C6—C7	86.7 (3)	C7—C6—O5—C12	14.6 (2)
C10—C1—C6—C5	−171.5 (2)	C5—C6—O5—C12	138.72 (19)
C2—C1—C6—C5	61.7 (2)	C1—C6—O5—C12	−100.3 (2)
C11—C1—C6—C5	−45.7 (3)	C13—C12—O5—C6	137.7 (2)
O5—C6—C7—O2	85.7 (3)	C8—C12—O5—C6	14.1 (2)
C5—C6—C7—O2	−29.4 (3)	C14—C12—O5—C6	−106.2 (2)
C1—C6—C7—O2	−159.3 (2)	C3—C2—O6—S1	107.6 (2)
O5—C6—C7—C8	−36.8 (2)	C1—C2—O6—S1	−144.83 (16)
C5—C6—C7—C8	−151.9 (2)	C2—O6—S1—O8	−169.57 (16)
C1—C6—C7—C8	78.2 (2)	C2—O6—S1—O7	−41.58 (19)
O2—C7—C8—C9	162.0 (2)	C2—O6—S1—C16	75.0 (2)
C6—C7—C8—C9	−74.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O2ⁱ	0.96	2.32	3.218 (4)	156

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₄O₈S
M_r	376.41
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.530 (3), 10.228 (3), 17.424 (5)
V (Å³)	1698.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.25 × 0.22 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.944, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	8175, 3151, 2633
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.085, 1.06
No. of reflections	3151
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20
Absolute structure	Flack (1983), 1325 Friedel pairs
Absolute structure parameter	0.13 (9)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), 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
C16—H16C···O2ⁱ	0.96	2.32	3.218 (4)	156

Symmetry code: (i) x, y+1, z.

Acknowledgements

This work was supported by the National Key S&T Research Foundation of China (grant No. 2010CB126105) and the National Natural Science Foundation of China (grant Nos. 30871663 and 30800729) as well as the program for Excellent Young Talents in Northwest A&F University (grant No. QNGG-2009-020).

References

Bruker (2001). SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gao, J. M., Wu, W. J., Zhang, J. W. & Konishi, Y. (2007). Nat. Prod. Rep. 24, 1153–1189. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spivey, A. C., Weston, M. & Woodhead, S. (2002). Chem. Soc. Rev. C31, 43–59. CrossRef Google Scholar

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Volume 67| Part 9| September 2011| Page o2496

doi:10.1107/S1600536811034179

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4α,6α-Dihy­dr­oxy-1β-methyl­sulfonyl-8α,9α-ep­­oxy-2β,12-epoxymethano-β-di­hydro­agaro­furan

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4α,6α-Dihydroxy-1β-methylsulfonyl-8α,9α-epoxy-2β,12-epoxymethano-β-dihydroagarofuran