6,8-Dihy­droxy-8a-methyl-3,5-dimethyl­idenedeca­hydro­naphtho­[2,3-b]furan-2(3H)-one

Liu, T.; Wu, H.-B.; Wang, W.-S.

doi:10.1107/S160053681204425X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3251

doi:10.1107/S160053681204425X

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6,8-Dihydroxy-8a-methyl-3,5-dimethylidenedecahydronaphtho[2,3-b]furan-2(3H)-one

Ting-ting Liu,^a Hai-Bo Wu ^a and Wen-Shu Wang ^a ^*

^aCollege of Life and Environment Science, Minzu University of China, Beijing 100081, People's Republic of China
^*Correspondence e-mail: wangws@muc.edu.cn

(Received 1 August 2012; accepted 25 October 2012; online 31 October 2012)

The title compound, C₁₅H₂₀O₄, is a eudesmanolide isolated from the Chinese medicinal plant Carpesium triste Maxim. The molecule contains three rings, viz. two fused six-membered rings in chair conformations and a five-membered ring in a flattened envelope conformation. In the crystal, two hydroxy groups are involved in the formation of intra- and intermolecular O—H⋯O hydrogen bonds. The H atoms in these groups are split, with site-occupation factors of 0.5. The intermolecular hydrogen bonds link molecules into chains propagating in [010].

Related literature

For related compounds extracted from Carpesium triste Maxim, see: Masao & Fumiko (1975 ).

Experimental

Crystal data

C₁₅H₂₀O₄
M_r = 264.31
Tetragonal, P 4₁ 2₁ 2
a = 6.4737 (4) Å
c = 62.438 (8) Å
V = 2616.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 133 K
0.54 × 0.48 × 0.32 mm

Data collection

Rigaku AFC10/Saturn-724+ CCD diffractometer
19607 measured reflections
1990 independent reflections
1826 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.124
S = 1.00
1990 reflections
185 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O2ⁱ	0.84 (1)	1.90 (1)	2.733 (3)	173 (5)
O2—H2O′⋯O3	0.84 (1)	1.94 (2)	2.690 (2)	148 (2)
O3—H3O′⋯O2	0.84 (1)	1.97 (4)	2.690 (2)	143 (5)
O3—H3O⋯O3ⁱⁱ	0.83 (1)	1.88 (2)	2.697 (3)	168 (6)
Symmetry codes: (i) y, x, -z; (ii) y+1, x-1, -z.

Data collection: CrystalClear (Rigaku/MSC, 2008 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S160053681204425X/rk2376sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204425X/rk2376Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204425X/rk2376Isup3.cml

checkCIF report

Comment top

Carpesium triste Maxim grows in the northeast and southwest area of mainland China. It is used as traditional Chinese medicine having effects on detoxification and antibacterial activities. As a part of our research on biological resource by ethnic minorities in Guizhou province, the title compound was isolated form Carpesium triste Maxim. Its structure was identified by NMR spectra data and compared with the previous reports (Masao & Fumiko, 1975). Herewith we present its molecular structure. The molecule of the title compound contains a three-ring system A/B/C (Fig. 1). Ring A and B are both in chair conformations and there is a trans-junction between ring A (C1-C5/C10) and ring B (C5-C7/C8-C10). Furthermore, the methyl group at C14 sites is in the opposite orientation with the two hydroxyl groups at C1 and C3 sites. The furan ring C (C8-C12/O1) is in an envelope-like conformation. Two hydroxy groups contribute to the formation of intra- and inter-molecular O–H···O hydrogen bonds (Table 1). The latter ones link molecules into chain propagated in direction [0 1 0].

Related literature top

For related compounds extracted from Carpesium triste Maxim, see: Masao & Fumiko (1975).

Experimental top

The air-dried whole plant of Carpesium triste Maxim (0.337 kg) were pulverized and extracted three times with CH₃OH (each for less than 1 minutes) at room temperature by flash-type extractor. The extract was concentrated to give a residue (33.5 g), which was further separated by CC (SiO₂, 200-300 mesh, petroleum ether/acetone (25:1, 20:1, 15:1, 10:1, 8:1, 5:1, 3:1, 2:1, 1:1(v/v)) to yield 9 fractions: Fr. 1-9. Each fraction was examined by TLC and combined to afford many subfractions. Fr. 5 (270 mg) was subjected to Sephadex LH-20 (CHCl₃/CH₃OH 1:1) to provide the title compound (4 mg). ¹H and ¹³C NMR spectral data of this compound was recorded on Bruker-AV-500 spectrometer, using CDCl₃ as solvent and Me₄Si as internal standard. The relative stereochemistry can be observed by X-ray diffraction experiment.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); 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. View of the title molecule showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. In the both hydroxy groups only one H atom is presented.

6,8-Dihydroxy-8a-methyl-3,5- dimethylidenedecahydronaphtho[2,3-b]furan-2(3H)-one top

Crystal data top

C₁₅H₂₀O₄	D_x = 1.342 Mg m⁻³
M_r = 264.31	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 4658 reflections
Hall symbol: P 4abw 2nw	θ = 3.2–27.9°
a = 6.4737 (4) Å	µ = 0.10 mm⁻¹
c = 62.438 (8) Å	T = 133 K
V = 2616.7 (5) Å³	Block, colourless
Z = 8	0.54 × 0.48 × 0.32 mm
F(000) = 1136

Data collection top

Rigaku AFC10/Saturn-724+ CCD diffractometer	1826 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.058
Graphite monochromator	θ_max = 27.9°, θ_min = 2.6°
Detector resolution: 28.5714 pixels mm^-1	h = −8→8
ϕ– and ω–scans	k = −8→8
19607 measured reflections	l = −82→82
1990 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0836P)² + 0.316P] where P = (F_o² + 2F_c²)/3
1990 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.23 e Å⁻³
6 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₂₀O₄	Z = 8
M_r = 264.31	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 0.10 mm⁻¹
a = 6.4737 (4) Å	T = 133 K
c = 62.438 (8) Å	0.54 × 0.48 × 0.32 mm
V = 2616.7 (5) Å³

Data collection top

Rigaku AFC10/Saturn-724+ CCD diffractometer	1826 reflections with I > 2σ(I)
19607 measured reflections	R_int = 0.058
1990 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	6 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.23 e Å⁻³
1990 reflections	Δρ_min = −0.21 e Å⁻³
185 parameters

Special details top

Experimental. Since the skeleton methyl groups in eudesmanolide are biogenic 8a position, we draw the relative stereochemistry of the title eudesmanolide, by reference to the structures of related eudesmanolide in (Masao & Fumiko, 1975) although the absolute configuration could not be reliably determined from anomalous dispersion effects, if Mo radiation is used in experiment. Furthermore, the relative stereochemistry in the title compound was confirmed by NMR data. ¹³C NMR (125 MHz, CDCl₃, δ,p.p.m.): 178.1 (C12), 149.2 (C4), 141.4 (C11), 120.5 (C13), 110.9 (C15), 77.6 (C8), 75.2 (C3), 74.7 (C1), 63.8 (C10), 40.3 (C7), 33.9 (C5), 33.6 (C9), 33.5 (C2), 26.8 (C6), 17.7 (C14).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
O1	0.6749 (2)	0.7974 (2)	0.09621 (2)	0.0238 (3)
O2	0.9609 (2)	0.7729 (3)	0.01700 (2)	0.0259 (4)
H2O	0.903 (5)	0.820 (6)	0.0061 (5)	0.031*	0.50
H2O'	1.080 (3)	0.727 (4)	0.0149 (8)	0.031*	0.50
O3	1.2633 (3)	0.4894 (3)	0.01385 (3)	0.0277 (4)
H3O	1.329 (7)	0.432 (8)	0.0040 (7)	0.033*	0.50
H3O'	1.216 (8)	0.609 (4)	0.0132 (9)	0.033*	0.50
O4	0.6433 (3)	0.7218 (3)	0.13102 (3)	0.0289 (4)
C1	0.8323 (3)	0.6114 (3)	0.02599 (3)	0.0222 (4)
H1	0.6856	0.6382	0.0218	0.027*
C2	0.8995 (3)	0.4040 (4)	0.01641 (3)	0.0252 (5)
H2A	0.8023	0.2947	0.0210	0.030*
H2B	0.8947	0.4124	0.0006	0.030*
C3	1.1183 (3)	0.3474 (3)	0.02353 (3)	0.0230 (4)
H3	1.1504	0.2041	0.0186	0.028*
C4	1.1394 (3)	0.3561 (3)	0.04749 (3)	0.0188 (4)
C5	1.0717 (3)	0.5576 (3)	0.05753 (3)	0.0176 (4)
H5	1.1636	0.6681	0.0517	0.021*
C6	1.0932 (3)	0.5634 (3)	0.08181 (3)	0.0197 (4)
H6A	1.2369	0.5273	0.0857	0.024*
H6B	1.0010	0.4578	0.0881	0.024*
C7	1.0399 (3)	0.7753 (3)	0.09141 (3)	0.0199 (4)
H7	1.1590	0.8724	0.0898	0.024*
C8	0.8417 (3)	0.8722 (3)	0.08222 (3)	0.0206 (4)
H8	0.8518	1.0254	0.0840	0.025*
C9	0.7925 (3)	0.8280 (3)	0.05891 (3)	0.0208 (4)
H9A	0.8663	0.9307	0.0500	0.025*
H9B	0.6427	0.8502	0.0567	0.025*
C10	0.8472 (3)	0.6116 (3)	0.05061 (3)	0.0196 (4)
C11	0.9826 (3)	0.7535 (3)	0.11464 (3)	0.0221 (4)
C12	0.7532 (3)	0.7548 (3)	0.11580 (3)	0.0217 (4)
C13	1.1009 (4)	0.7239 (4)	0.13160 (3)	0.0287 (5)
H13A	1.0399	0.7022	0.1453	0.034*
H13B	1.2470	0.7243	0.1301	0.034*
C14	0.6907 (3)	0.4523 (3)	0.05931 (4)	0.0235 (5)
H14A	0.6728	0.4728	0.0747	0.028*
H14B	0.7424	0.3124	0.0566	0.028*
H14C	0.5577	0.4707	0.0521	0.028*
C15	1.2136 (3)	0.1949 (3)	0.05820 (4)	0.0253 (5)
H15A	1.2536	0.0735	0.0507	0.030*
H15B	1.2267	0.2010	0.0733	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0227 (8)	0.0298 (8)	0.0189 (7)	0.0009 (6)	0.0021 (6)	0.0013 (6)
O2	0.0313 (9)	0.0272 (8)	0.0192 (8)	−0.0013 (7)	0.0007 (6)	0.0057 (6)
O3	0.0311 (9)	0.0287 (8)	0.0232 (8)	−0.0024 (7)	0.0085 (7)	0.0027 (7)
O4	0.0321 (9)	0.0319 (8)	0.0228 (8)	0.0021 (7)	0.0073 (7)	0.0024 (7)
C1	0.0221 (10)	0.0250 (10)	0.0196 (10)	−0.0023 (8)	−0.0023 (8)	0.0024 (8)
C2	0.0281 (11)	0.0314 (12)	0.0161 (10)	−0.0054 (9)	−0.0024 (8)	−0.0028 (9)
C3	0.0272 (11)	0.0210 (10)	0.0208 (10)	−0.0026 (8)	0.0038 (9)	−0.0021 (8)
C4	0.0183 (9)	0.0207 (9)	0.0173 (10)	−0.0031 (7)	0.0014 (8)	−0.0015 (8)
C5	0.0182 (9)	0.0187 (10)	0.0158 (9)	−0.0015 (7)	−0.0012 (7)	−0.0003 (8)
C6	0.0215 (10)	0.0211 (10)	0.0164 (9)	0.0004 (8)	−0.0008 (8)	0.0014 (8)
C7	0.0213 (10)	0.0212 (10)	0.0171 (9)	−0.0017 (8)	−0.0012 (8)	0.0010 (8)
C8	0.0241 (10)	0.0198 (9)	0.0178 (10)	−0.0008 (8)	0.0015 (8)	0.0009 (8)
C9	0.0222 (10)	0.0212 (10)	0.0190 (10)	0.0024 (8)	−0.0002 (8)	0.0025 (8)
C10	0.0183 (9)	0.0234 (10)	0.0169 (10)	−0.0012 (8)	−0.0011 (8)	0.0017 (8)
C11	0.0265 (10)	0.0202 (10)	0.0197 (10)	−0.0004 (8)	0.0014 (8)	−0.0010 (8)
C12	0.0282 (11)	0.0201 (10)	0.0169 (9)	0.0007 (8)	0.0015 (8)	−0.0007 (8)
C13	0.0318 (12)	0.0360 (12)	0.0182 (10)	−0.0009 (10)	−0.0014 (9)	0.0003 (9)
C14	0.0203 (10)	0.0257 (11)	0.0245 (10)	−0.0056 (8)	0.0015 (8)	0.0005 (9)
C15	0.0256 (10)	0.0246 (11)	0.0255 (11)	−0.0009 (8)	0.0008 (9)	−0.0012 (8)

Geometric parameters (Å, º) top

O1—C12	1.353 (3)	C6—C7	1.536 (3)
O1—C8	1.471 (2)	C6—H6A	0.9900
O2—C1	1.449 (3)	C6—H6B	0.9900
O2—H2O	0.840 (10)	C7—C11	1.504 (3)
O2—H2O'	0.839 (10)	C7—C8	1.539 (3)
O3—C3	1.447 (3)	C7—H7	1.0000
O3—H3O	0.834 (10)	C8—C9	1.517 (3)
O3—H3O'	0.836 (10)	C8—H8	1.0000
O4—C12	1.206 (3)	C9—C10	1.535 (3)
C1—C2	1.533 (3)	C9—H9A	0.9900
C1—C10	1.540 (3)	C9—H9B	0.9900
C1—H1	1.0000	C10—C14	1.544 (3)
C2—C3	1.529 (3)	C11—C13	1.321 (3)
C2—H2A	0.9900	C11—C12	1.486 (3)
C2—H2B	0.9900	C13—H13A	0.9500
C3—C4	1.503 (3)	C13—H13B	0.9500
C3—H3	1.0000	C14—H14A	0.9800
C4—C15	1.330 (3)	C14—H14B	0.9800
C4—C5	1.512 (3)	C14—H14C	0.9800
C5—C6	1.523 (3)	C15—H15A	0.9500
C5—C10	1.556 (3)	C15—H15B	0.9500
C5—H5	1.0000

C12—O1—C8	109.21 (16)	C11—C7—C8	101.06 (17)
C1—O2—H2O	108.7 (12)	C6—C7—C8	113.93 (16)
C1—O2—H2O'	109.6 (12)	C11—C7—H7	110.4
H2O—O2—H2O'	115 (5)	C6—C7—H7	110.4
C3—O3—H3O	111 (4)	C8—C7—H7	110.4
C3—O3—H3O'	112 (4)	O1—C8—C9	110.70 (17)
H3O—O3—H3O'	124 (6)	O1—C8—C7	104.87 (15)
O2—C1—C2	108.53 (17)	C9—C8—C7	117.13 (17)
O2—C1—C10	110.48 (16)	O1—C8—H8	107.9
C2—C1—C10	111.86 (17)	C9—C8—H8	107.9
O2—C1—H1	108.6	C7—C8—H8	107.9
C2—C1—H1	108.6	C8—C9—C10	116.56 (16)
C10—C1—H1	108.6	C8—C9—H9A	108.2
C3—C2—C1	111.05 (17)	C10—C9—H9A	108.2
C3—C2—H2A	109.4	C8—C9—H9B	108.2
C1—C2—H2A	109.4	C10—C9—H9B	108.2
C3—C2—H2B	109.4	H9A—C9—H9B	107.3
C1—C2—H2B	109.4	C9—C10—C1	108.84 (16)
H2A—C2—H2B	108.0	C9—C10—C14	109.84 (17)
O3—C3—C4	109.47 (17)	C1—C10—C14	108.02 (16)
O3—C3—C2	109.10 (17)	C9—C10—C5	109.08 (16)
C4—C3—C2	111.38 (17)	C1—C10—C5	109.60 (16)
O3—C3—H3	108.9	C14—C10—C5	111.41 (17)
C4—C3—H3	108.9	C13—C11—C12	122.7 (2)
C2—C3—H3	108.9	C13—C11—C7	130.1 (2)
C15—C4—C3	120.26 (19)	C12—C11—C7	107.06 (18)
C15—C4—C5	124.99 (19)	O4—C12—O1	121.8 (2)
C3—C4—C5	114.75 (17)	O4—C12—C11	128.8 (2)
C4—C5—C6	114.06 (17)	O1—C12—C11	109.35 (17)
C4—C5—C10	110.44 (16)	C11—C13—H13A	120.0
C6—C5—C10	110.86 (16)	C11—C13—H13B	120.0
C4—C5—H5	107.0	H13A—C13—H13B	120.0
C6—C5—H5	107.0	C10—C14—H14A	109.5
C10—C5—H5	107.0	C10—C14—H14B	109.5
C5—C6—C7	112.94 (16)	H14A—C14—H14B	109.5
C5—C6—H6A	109.0	C10—C14—H14C	109.5
C7—C6—H6A	109.0	H14A—C14—H14C	109.5
C5—C6—H6B	109.0	H14B—C14—H14C	109.5
C7—C6—H6B	109.0	C4—C15—H15A	120.0
H6A—C6—H6B	107.8	C4—C15—H15B	120.0
C11—C7—C6	110.34 (17)	H15A—C15—H15B	120.0

O2—C1—C2—C3	65.9 (2)	C8—C9—C10—C14	74.5 (2)
C10—C1—C2—C3	−56.2 (2)	C8—C9—C10—C5	−47.9 (2)
C1—C2—C3—O3	−68.2 (2)	O2—C1—C10—C9	55.0 (2)
C1—C2—C3—C4	52.7 (2)	C2—C1—C10—C9	176.05 (17)
O3—C3—C4—C15	−112.1 (2)	O2—C1—C10—C14	174.25 (17)
C2—C3—C4—C15	127.1 (2)	C2—C1—C10—C14	−64.7 (2)
O3—C3—C4—C5	67.6 (2)	O2—C1—C10—C5	−64.2 (2)
C2—C3—C4—C5	−53.2 (2)	C2—C1—C10—C5	56.8 (2)
C15—C4—C5—C6	−0.6 (3)	C4—C5—C10—C9	−173.51 (16)
C3—C4—C5—C6	179.74 (17)	C6—C5—C10—C9	59.1 (2)
C15—C4—C5—C10	−126.2 (2)	C4—C5—C10—C1	−54.4 (2)
C3—C4—C5—C10	54.1 (2)	C6—C5—C10—C1	178.14 (16)
C4—C5—C6—C7	175.41 (16)	C4—C5—C10—C14	65.1 (2)
C10—C5—C6—C7	−59.2 (2)	C6—C5—C10—C14	−62.4 (2)
C5—C6—C7—C11	157.85 (17)	C6—C7—C11—C13	76.2 (3)
C5—C6—C7—C8	45.0 (2)	C8—C7—C11—C13	−162.9 (2)
C12—O1—C8—C9	153.66 (17)	C6—C7—C11—C12	−99.4 (2)
C12—O1—C8—C7	26.4 (2)	C8—C7—C11—C12	21.5 (2)
C11—C7—C8—O1	−28.42 (19)	C8—O1—C12—O4	168.33 (19)
C6—C7—C8—O1	89.89 (19)	C8—O1—C12—C11	−12.6 (2)
C11—C7—C8—C9	−151.58 (17)	C13—C11—C12—O4	−3.7 (4)
C6—C7—C8—C9	−33.3 (2)	C7—C11—C12—O4	172.3 (2)
O1—C8—C9—C10	−83.9 (2)	C13—C11—C12—O1	177.4 (2)
C7—C8—C9—C10	36.2 (3)	C7—C11—C12—O1	−6.6 (2)
C8—C9—C10—C1	−167.46 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O2ⁱ	0.84 (1)	1.90 (1)	2.733 (3)	173 (5)
O2—H2O′···O3	0.84 (1)	1.94 (2)	2.690 (2)	148 (2)
O3—H3O′···O2	0.84 (1)	1.97 (4)	2.690 (2)	143 (5)
O3—H3O···O3ⁱⁱ	0.83 (1)	1.88 (2)	2.697 (3)	168 (6)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀O₄
M_r	264.31
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	133
a, c (Å)	6.4737 (4), 62.438 (8)
V (Å³)	2616.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.54 × 0.48 × 0.32

Data collection
Diffractometer	Rigaku AFC10/Saturn-724+ CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19607, 1990, 1826
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.124, 1.00
No. of reflections	1990
No. of parameters	185
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: CrystalClear (Rigaku/MSC, 2008), 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
O2—H2O···O2ⁱ	0.840 (10)	1.898 (12)	2.733 (3)	173 (5)
O2—H2O'···O3	0.839 (10)	1.942 (17)	2.690 (2)	147.9 (17)
O3—H3O'···O2	0.836 (10)	1.97 (4)	2.690 (2)	143 (5)
O3—H3O···O3ⁱⁱ	0.834 (10)	1.876 (16)	2.697 (3)	168 (6)

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

Acknowledgements

The project was supported by the 985 Project (grant Nos. MUC98504-14, MUC98507-08), Minzu University of China, together with the `Programme of Introducing Talents of Discipline to Universities' (grant No. B08044), and the `Project for Scientific and Technical Achievements in Industrialization', Beijing Education Commission.

References

Masao, M. & Fumiko, S. (1975). Phytochemistry, 14, 2247–2248. Google Scholar
Rigaku/MSC (2008). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3251

doi:10.1107/S160053681204425X

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

6,8-Dihy­dr­oxy-8a-methyl-3,5-di­methyl­idenedeca­hydro­naphtho­[2,3-b]furan-2(3H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,8-Dihydroxy-8a-methyl-3,5-dimethylidenedecahydronaphtho[2,3-b]furan-2(3H)-one