9a-Hy­droxy-3,8a-dimethyl-5-methyl­ene-4,4a,5,6,9,9a-hexa­hydro­naphtho­[2,3-b]furan-2(8aH)-one

Liu, W.-H.; He, J.; Ding, Z.-S.; Song, Z.-C.; Zhan, Z.-J.

doi:10.1107/S1600536811006519

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o730-o731

doi:10.1107/S1600536811006519

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access

9a-Hydroxy-3,8a-dimethyl-5-methylene-4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one

Wen-Hong Liu,^a Jie He,^a Zhi-Shan Ding,^b Zhong-Cheng Song ^a ^* and Zha-Jun Zhan ^c ^*

^aBioengineering Department, Zhejiang Traditional Chinese Medicine University, Hangzhou 310053, People's Republic of China, ^bDepartment of Life Science, Zhejiang Traditional Chinese Medicine University, Hangzhou 310053, People's Republic of China, and ^cCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China
^*Correspondence e-mail: songzhongcheng@gmail.com, tianranyaowu@zjut.edu.cn

(Received 13 February 2011; accepted 21 February 2011; online 26 February 2011)

The title compound, C₁₅H₁₈O₃, was isolated from Lactarius piperatus (Fr.) S. F. Gary collected from the Kunming area in Yunnan province, China. The central cyclohexyl ring adopts a chair conformation, while the furanone ring is close to planar (r.m.s. deviation = 0.0174 Å). The remaining methylene cyclohexene ring has a flattened chair conformation. In the crystal, molecules are linked via intermolecular O—H⋯O and C—H⋯O hydrogen bonds into zigzag chains along the a axis.

Related literature

For the distribution of the fungus Lactarius piperatus in China, see: Xie et al. (1996 ). For the anti-tumor activity of this species see: Mo et al. (1995 ). A series of sesquiterpenes has been isolated from the genus Lactarius, see: De Bernardi et al. (1993 ); Sterner et al. (1990 ). For the isolation of amino acids and sesquiterpenes from L. piperatus growing in Europe and Japan and their biological activity, see: Fushiya et al. (1988 ); Sterner et al. (1985a ,b ); Yaoita et al. (1999 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₈O₃
M_r = 247.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.5150 (19) Å
b = 10.885 (2) Å
c = 12.594 (3) Å
V = 1304.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.975, T_max = 0.983
2616 measured reflections
1367 independent reflections
1209 reflections with I > 2σ(I)
R_int = 0.021
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.06
1367 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.82	1.99	2.796 (2)	169
C1—H1A⋯O1	0.93	2.63	3.495 (2)	118
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811006519/sj5106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006519/sj5106Isup2.hkl

checkCIF report

Comment top

The fungus Lactarius piperatus (Fr.) S. F. Gary (family Russulaceae, Basidiomycotina) is widely distributed in China (Xie et al., 1996). The ethanolic extract has been reported to inhibit the growth of several tumor cell lines (Mo et al., 1995). L. Piperatus, growing in Europe and Japan, has been investigated, and a new amino acid and a few sesquiterpenes were isolated (Fushiya et al., 1988; Sterner et al., 1985a; Yaoita et al., 1999), but L. piperatus growing in China has not been previously investigated chemically. A series of sesquiterpenes, belonging to the marasmane, lactarane, isolactarane, and secolactarane types, has been isolated from the genus of Lactarius (De Bernardi et al., 1993, Sterner et al., 1990). These sesquiterpenes provide a chemical defense system against parasites and predators (Sterner et al., 1985b).

The molecular structure of the title compound is shown in Fig. 1. All bond lengths are within normal ranges (Allen et al., 1987). The central cyclohexyl ring C5-C6-C7-C10-C11-C12 adopts a chair conformation. The dihedral angle between the C7-C8-C9-O1-C10 ring and the plane defined by C12-C1-C2-C3-C4 is 75.3 (3)°. Atom C5 deviates 0.692 (2) Å from the plane defined by C12-C1-C2-C3-C4. In the crystal, molecules are linked via intermolecular O—H···O hydrogen bonds (Table 1) to form chains along the a axis (Fig. 2).

Related literature top

For the distribution of the fungus Lactarius piperatus in China, see: Xie et al. (1996). For the anti-tumor activity of this species see: Mo et al. (1995). A series of sesquiterpenes has been isolated from the genus Lactarius, see: De Bernardi et al. (1993); Sterner et al. (1990). For the isolation of amino acids and sesquiterpenes from L. piperatus growing in Europe and Japan and their biological activity, see: Fushiya et al. (1988); Sterner et al. (1985a,b); Yaoita et al. (1999). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Plant material: Lactarius piperatus (Fr.) S. F. Gary was collected from the Kunming area in Yunnan province of China and authenticated by Prof. Mu Zang, Kunming Institute of Botany, where a voucher specimen labeled as HKAS 30213, was deposited. Extraction and Isolation: The fresh mushroom (5 kg) was extracted with 95% EtOH and yielded 91 g of crude extract, which was then suspended in 2 L water. The suspension was partitioned with EtOAc (4× 200 ml) to give an EtOAc-soluble portion, and a water-soluble fraction. After removal of the EtOAc under reduced pressure, 49 g of dark residue was obtained, and this was subjected to silica-gel chromatography, eluted with a stepwise gradient solvent system of petroleum/acetone 10 : 0 to 5 : 5, followed by MeOH, to afford four major fractions (monitored by TLC). Fr. 1 consisted mainly of fatty acids. Fr. 4 was much smaller and complex. The separation and purification were focused on Fr. 2 and 3, in which the sesquiterpenes were concentrated. A portion of sub-fraction Fr. 2 was re-chromatographed on silica gel using a petroleum ether-acetone (8:2) system and the isolated product was recrystallized from chloroform-methanol (7:3) to yield the active component as light colorless crystals.

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. The molecular structure of the title compounds with atom labels and the 30% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. Molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

9a-Hydroxy-3,8a-dimethyl-5-methylene-4,4a,5,6,9,9a-hexahydronaphtho[2,3- b]furan-2(8aH)-one top

Crystal data top

C₁₅H₁₈O₃	F(000) = 532
M_r = 247.30	D_x = 1.259 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.5150 (19) Å	θ = 10–13°
b = 10.885 (2) Å	µ = 0.09 mm⁻¹
c = 12.594 (3) Å	T = 298 K
V = 1304.4 (5) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1209 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 25.3°, θ_min = 2.5°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.975, T_max = 0.983	l = −15→15
2616 measured reflections	3 standard reflections every 200 reflections
1367 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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0474P)² + 0.1815P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
1367 reflections	Δρ_max = 0.15 e Å⁻³
164 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (3)

Crystal data top

C₁₅H₁₈O₃	V = 1304.4 (5) Å³
M_r = 247.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.5150 (19) Å	µ = 0.09 mm⁻¹
b = 10.885 (2) Å	T = 298 K
c = 12.594 (3) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1209 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.021
T_min = 0.975, T_max = 0.983	3 standard reflections every 200 reflections
2616 measured reflections	intensity decay: 1%
1367 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
1367 reflections	Δρ_min = −0.12 e Å⁻³
164 parameters

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
O1	0.40511 (17)	0.69401 (16)	0.36817 (13)	0.0514 (5)
C1	−0.0968 (3)	0.6294 (2)	0.4001 (2)	0.0512 (6)
H1A	−0.0918	0.6506	0.4715	0.061*
O2	0.51038 (18)	0.85545 (16)	0.29192 (14)	0.0627 (5)
C2	−0.2158 (3)	0.6509 (3)	0.3493 (2)	0.0609 (8)
H2A	−0.2893	0.6871	0.3866	0.073*
O3	0.34477 (19)	0.48626 (15)	0.36469 (14)	0.0576 (5)
H3A	0.3854	0.4559	0.3136	0.086*
C3	−0.2383 (3)	0.6201 (3)	0.2348 (2)	0.0607 (8)
H3B	−0.2599	0.6949	0.1962	0.073*
H3C	−0.3188	0.5658	0.2288	0.073*
C4	−0.1128 (3)	0.5590 (2)	0.18373 (19)	0.0478 (6)
C5	0.0243 (2)	0.60217 (19)	0.22901 (16)	0.0387 (5)
H5A	0.0223	0.6920	0.2238	0.046*
C6	0.1574 (3)	0.5615 (2)	0.16947 (18)	0.0440 (6)
H6A	0.1696	0.4732	0.1748	0.053*
H6B	0.1513	0.5837	0.0950	0.053*
C7	0.2764 (2)	0.6267 (2)	0.22127 (18)	0.0405 (5)
C8	0.3544 (2)	0.7232 (2)	0.19078 (17)	0.0424 (5)
C9	0.4327 (2)	0.7661 (2)	0.2838 (2)	0.0460 (6)
C10	0.2974 (3)	0.6033 (2)	0.33811 (19)	0.0425 (6)
C11	0.1634 (2)	0.6320 (2)	0.39810 (17)	0.0423 (5)
H11A	0.1507	0.7204	0.3999	0.051*
H11B	0.1735	0.6039	0.4708	0.051*
C12	0.0308 (2)	0.5729 (2)	0.34989 (18)	0.0395 (5)
C13	0.0256 (3)	0.4326 (2)	0.3715 (2)	0.0569 (7)
H13B	0.0301	0.4181	0.4466	0.085*
H13C	0.1040	0.3934	0.3374	0.085*
H13D	−0.0604	0.3994	0.3439	0.085*
C14	−0.1255 (3)	0.4774 (3)	0.1063 (2)	0.0644 (8)
H14A	−0.0457	0.4425	0.0761	0.077*
H14B	−0.2142	0.4549	0.0821	0.077*
C15	0.3624 (3)	0.7890 (3)	0.0874 (2)	0.0607 (7)
H15A	0.3043	0.7478	0.0363	0.091*
H15B	0.4580	0.7895	0.0629	0.091*
H15C	0.3303	0.8719	0.0964	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0459 (9)	0.0572 (10)	0.0510 (9)	−0.0036 (9)	−0.0053 (8)	−0.0002 (9)
C1	0.0518 (14)	0.0515 (14)	0.0503 (13)	−0.0019 (13)	0.0146 (12)	−0.0027 (12)
O2	0.0517 (10)	0.0567 (11)	0.0797 (12)	−0.0136 (10)	0.0040 (11)	−0.0053 (10)
C2	0.0462 (15)	0.0611 (17)	0.0754 (19)	0.0031 (14)	0.0136 (14)	−0.0024 (16)
O3	0.0614 (11)	0.0476 (9)	0.0636 (11)	0.0159 (9)	0.0033 (10)	0.0107 (9)
C3	0.0448 (14)	0.0588 (16)	0.0784 (19)	−0.0034 (13)	−0.0039 (13)	0.0088 (16)
C4	0.0525 (15)	0.0402 (12)	0.0507 (13)	−0.0079 (12)	−0.0067 (12)	0.0077 (11)
C5	0.0455 (13)	0.0272 (10)	0.0433 (13)	−0.0020 (10)	0.0012 (11)	0.0012 (9)
C6	0.0532 (14)	0.0388 (12)	0.0402 (11)	−0.0012 (12)	0.0036 (11)	−0.0045 (10)
C7	0.0425 (12)	0.0366 (12)	0.0425 (11)	0.0061 (10)	0.0074 (10)	−0.0040 (11)
C8	0.0407 (12)	0.0394 (11)	0.0471 (12)	0.0056 (11)	0.0090 (10)	−0.0018 (10)
C9	0.0358 (11)	0.0439 (13)	0.0582 (14)	0.0033 (11)	0.0074 (11)	−0.0032 (12)
C10	0.0436 (12)	0.0370 (12)	0.0470 (12)	0.0028 (11)	−0.0037 (11)	0.0014 (10)
C11	0.0512 (13)	0.0365 (11)	0.0391 (11)	0.0019 (11)	0.0017 (11)	−0.0005 (10)
C12	0.0454 (13)	0.0328 (11)	0.0403 (11)	−0.0010 (10)	0.0039 (10)	0.0016 (10)
C13	0.0671 (17)	0.0367 (12)	0.0668 (16)	−0.0045 (13)	0.0016 (15)	0.0124 (12)
C14	0.0676 (18)	0.0618 (16)	0.0638 (16)	−0.0190 (15)	−0.0125 (15)	−0.0062 (14)
C15	0.0710 (18)	0.0546 (15)	0.0566 (14)	−0.0034 (15)	0.0161 (14)	0.0059 (13)

Geometric parameters (Å, º) top

O1—C9	1.347 (3)	C6—H6A	0.9700
O1—C10	1.473 (3)	C6—H6B	0.9700
C1—C2	1.321 (4)	C7—C8	1.342 (3)
C1—C12	1.501 (3)	C7—C10	1.507 (3)
C1—H1A	0.9300	C8—C9	1.465 (3)
O2—C9	1.225 (3)	C8—C15	1.487 (3)
C2—C3	1.496 (4)	C10—C11	1.515 (3)
C2—H2A	0.9300	C11—C12	1.541 (3)
O3—C10	1.392 (3)	C11—H11A	0.9700
O3—H3A	0.8200	C11—H11B	0.9700
C3—C4	1.510 (4)	C12—C13	1.552 (3)
C3—H3B	0.9700	C13—H13B	0.9600
C3—H3C	0.9700	C13—H13C	0.9600
C4—C14	1.325 (4)	C13—H13D	0.9600
C4—C5	1.499 (3)	C14—H14A	0.9300
C5—C6	1.537 (3)	C14—H14B	0.9300
C5—C12	1.557 (3)	C15—H15A	0.9600
C5—H5A	0.9800	C15—H15B	0.9600
C6—C7	1.488 (3)	C15—H15C	0.9600

C9—O1—C10	108.89 (17)	O2—C9—C8	128.8 (2)
C2—C1—C12	124.2 (2)	O1—C9—C8	110.22 (19)
C2—C1—H1A	117.9	O3—C10—O1	109.03 (18)
C12—C1—H1A	117.9	O3—C10—C7	115.6 (2)
C1—C2—C3	123.3 (3)	O1—C10—C7	103.28 (19)
C1—C2—H2A	118.3	O3—C10—C11	110.0 (2)
C3—C2—H2A	118.3	O1—C10—C11	108.62 (18)
C10—O3—H3A	109.5	C7—C10—C11	109.95 (19)
C2—C3—C4	113.4 (2)	C10—C11—C12	113.98 (17)
C2—C3—H3B	108.9	C10—C11—H11A	108.8
C4—C3—H3B	108.9	C12—C11—H11A	108.8
C2—C3—H3C	108.9	C10—C11—H11B	108.8
C4—C3—H3C	108.9	C12—C11—H11B	108.8
H3B—C3—H3C	107.7	H11A—C11—H11B	107.7
C14—C4—C5	124.7 (2)	C1—C12—C11	108.96 (18)
C14—C4—C3	122.4 (2)	C1—C12—C13	107.7 (2)
C5—C4—C3	112.8 (2)	C11—C12—C13	111.6 (2)
C4—C5—C6	116.17 (18)	C1—C12—C5	107.21 (19)
C4—C5—C12	110.03 (18)	C11—C12—C5	109.40 (18)
C6—C5—C12	112.67 (19)	C13—C12—C5	111.8 (2)
C4—C5—H5A	105.7	C12—C13—H13B	109.5
C6—C5—H5A	105.7	C12—C13—H13C	109.5
C12—C5—H5A	105.7	H13B—C13—H13C	109.5
C7—C6—C5	106.03 (17)	C12—C13—H13D	109.5
C7—C6—H6A	110.5	H13B—C13—H13D	109.5
C5—C6—H6A	110.5	H13C—C13—H13D	109.5
C7—C6—H6B	110.5	C4—C14—H14A	120.0
C5—C6—H6B	110.5	C4—C14—H14B	120.0
H6A—C6—H6B	108.7	H14A—C14—H14B	120.0
C8—C7—C6	132.0 (2)	C8—C15—H15A	109.5
C8—C7—C10	109.8 (2)	C8—C15—H15B	109.5
C6—C7—C10	116.6 (2)	H15A—C15—H15B	109.5
C7—C8—C9	107.6 (2)	C8—C15—H15C	109.5
C7—C8—C15	131.0 (2)	H15A—C15—H15C	109.5
C9—C8—C15	121.3 (2)	H15B—C15—H15C	109.5
O2—C9—O1	120.9 (2)

C12—C1—C2—C3	0.7 (5)	C9—O1—C10—C7	4.8 (2)
C1—C2—C3—C4	1.4 (4)	C9—O1—C10—C11	−111.9 (2)
C2—C3—C4—C14	148.5 (3)	C8—C7—C10—O3	−122.8 (2)
C2—C3—C4—C5	−32.3 (3)	C6—C7—C10—O3	69.8 (3)
C14—C4—C5—C6	9.1 (3)	C8—C7—C10—O1	−3.8 (2)
C3—C4—C5—C6	−170.1 (2)	C6—C7—C10—O1	−171.18 (18)
C14—C4—C5—C12	−120.4 (3)	C8—C7—C10—C11	111.9 (2)
C3—C4—C5—C12	60.4 (3)	C6—C7—C10—C11	−55.4 (3)
C4—C5—C6—C7	173.61 (19)	O3—C10—C11—C12	−79.2 (2)
C12—C5—C6—C7	−58.2 (2)	O1—C10—C11—C12	161.56 (18)
C5—C6—C7—C8	−105.0 (3)	C7—C10—C11—C12	49.2 (3)
C5—C6—C7—C10	59.0 (2)	C2—C1—C12—C11	144.3 (3)
C6—C7—C8—C9	166.2 (2)	C2—C1—C12—C13	−94.5 (3)
C10—C7—C8—C9	1.5 (2)	C2—C1—C12—C5	26.0 (3)
C6—C7—C8—C15	−9.7 (4)	C10—C11—C12—C1	−167.5 (2)
C10—C7—C8—C15	−174.5 (2)	C10—C11—C12—C13	73.7 (3)
C10—O1—C9—O2	173.7 (2)	C10—C11—C12—C5	−50.6 (2)
C10—O1—C9—C8	−4.2 (2)	C4—C5—C12—C1	−54.9 (2)
C7—C8—C9—O2	−176.0 (2)	C6—C5—C12—C1	173.76 (18)
C15—C8—C9—O2	0.4 (4)	C4—C5—C12—C11	−172.89 (18)
C7—C8—C9—O1	1.7 (3)	C6—C5—C12—C11	55.7 (2)
C15—C8—C9—O1	178.1 (2)	C4—C5—C12—C13	63.0 (3)
C9—O1—C10—O3	128.3 (2)	C6—C5—C12—C13	−68.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.82	1.99	2.796 (2)	169
C1—H1A···O1	0.93	2.63	3.495 (2)	118

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈O₃
M_r	247.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	9.5150 (19), 10.885 (2), 12.594 (3)
V (Å³)	1304.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	2616, 1367, 1209
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.06
No. of reflections	1367
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.12

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
O3—H3A···O2ⁱ	0.82	1.99	2.796 (2)	169
C1—H1A···O1	0.93	2.63	3.495 (2)	118

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of Zhejiang Province (Project Y2101290), the Zhejiang Traditional Chinese Medicine Administration Fund (Project 2009 C A003) and Zhejiang Traditional Chinese Medicine University (Project 2009ZY06).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Volume 67| Part 3| March 2011| Pages o730-o731

doi:10.1107/S1600536811006519

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

9a-Hy­dr­oxy-3,8a-di­methyl-5-methyl­ene-4,4a,5,6,9,9a-hexa­hydro­naphtho­[2,3-b]furan-2(8aH)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9a-Hydroxy-3,8a-dimethyl-5-methylene-4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one