4α,6α-Dihy-droxy-1β-methyl-sulfonyl-8α,9α-ep-oxy-2β,12-epoxymethano-β-dihydro-agarofuran.

The title mol-ecule, C(16)H(24)O(8)S, is a dihydro-agrofuran 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 inter-molecular C-H⋯O hydrogen-bonding inter-action to stabilize the packing.

Related literature

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

Experimental

Crystal data

C16H24O8S

M = 376.41

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.085

S = 1.06

3151 reflections

232 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1325 Friedel pairs

Flack parameter: 0.13 (9)

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034179/qm2023sup1.cif

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

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

C16H24O8S	F(000) = 800
Mr = 376.41	Dx = 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

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

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(Fo2) + (0.0384P)2 + 0.135P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3151 reflections	Δρmax = 0.19 e Å−3
232 parameters	Δρmin = −0.20 e Å−3
0 restraints	Absolute structure: Flack (1983), 1325 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.13 (9)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .