(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetra­methyl-2-oxoperhydro­naphtho[2,1-b]furan-7-yl acetate

Huang, Q.-C.; Li, B.-G.; Xie, Y.-P.; Yu, K.-B.; Zhang, G.-L.

doi:10.1107/S1600536808025737

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1765

doi:10.1107/S1600536808025737

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(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetramethyl-2-oxoperhydronaphtho[2,1-b]furan-7-yl acetate

Qing-Chun Huang,^a,^b Bo-Gang Li,^a Yi-Peng Xie,^a,^b Kai-Bei Yu ^b and Guo-Lin Zhang ^a ^*

^aChengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China, and ^bChengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: youthhuang@yahoo.com.cn

(Received 3 August 2008; accepted 9 August 2008; online 16 August 2008)

The title compound (common name: 3β-acetoxy-8-epi-sclareolide), C₁₈H₂₈O₄, is a sclareolide derivative, which was synthesized from 9(11)-en-3β-acetoxy-8-epi-sclareolide. In the molecular structure, the two six-membered rings display chair conformations and the five-membered ring displays an envelope conformation. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For general background, see: Choudhary et al. (2004 ); Quideau et al. (2002 ). For related structures, see: Devi et al. (2004 ); Bhattacharyya et al. (2006 ). For synthesis, see: Yang et al. (2006 ).

Experimental

Crystal data

C₁₈H₂₈O₄
M_r = 308.40
Monoclinic, P 2₁
a = 10.1935 (5) Å
b = 7.3226 (3) Å
c = 11.3056 (4) Å
β = 99.2940 (1)°
V = 832.81 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 153 (2) K
0.60 × 0.54 × 0.47 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: none
8195 measured reflections
2046 independent reflections
1943 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 0.99
2046 reflections
205 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O2ⁱ	0.98	2.55	3.383 (3)	143
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025737/xu2447sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025737/xu2447Isup2.hkl

checkCIF report

Comment top

Sclareolide has exhibited phytotoxic activity and cytotoxicity against human cancer cell lines (Choudhary et al., 2004). It also be important pharmaceutical intermediates (Quideau et al., 2002). Here we report the synthesis and crystal structure of the title compound which is a 8-epi-sclareolide type compound.

The molecular structure is shown in Fig. 1. The molecule contains two six-membered rings, A (atoms C1–C5/C10) and B (atoms C5–C10), and one five-membered lactone rings C (C8/C9/O1/C11/C12). The cyclohexane ring A and the cyclohexane ring B exist both in chair conformation. The γ-lactone rings C adopt envelope conformations with C9 at the flap (Devi et al., 2004; Bhattacharyya et al., 2006). The rings A/B are trans fused and the rings B/C are cis fused. The C1/C2/C4/C5, C6/C7/C9/C10, C8/C11/C12/O1 form least square plane D, E and F, respectively. The dihedral angels between planes D and E is 15.50 (8)°, between planes E and F is 59.03 (7)°, between planes D and F is 43.54 (7)°. The C3 and C10 deviate from plane D by 0.634 (2)and 0.644 (2) Å, respectively. The C5 and C8 deviate from plane E by 0.765 (2) and 0.382 (3) Å, respectively. The C9 deviates from plane F by 0.566 (3) Å.

The intermolacular weak C—H···O hydrogen bonding presents in the crystal structure (Table 1).

Related literature top

For general background, see: Choudhary et al. (2004); Quideau et al. (2002). For related structures, see: Devi et al. (2004); Bhattacharyya et al. (2006). For synthesis, see: Yang et al. (2006).

Experimental top

To a methanol solution (10 ml) of 9(11)-en-3β-Acetoxy-8-epi-sclareolide (1 mmol) (Yang et al., 2006) was added NiCl₂.6H₂O (1 mmol), and the mixture was cooled to 273 K with an ice bath, then NaBH₄ (4 mmol) was added in small portions over 30 min. The ice bath was removed and the reaction mixture was left stirred for 4 h at room temperature. Then the suspension was filtered, and after usual workup, the residue was purified by flash chromatography eluted with petroleum ether–ethyl acetate (10:1) to afford the title compound. Yield (97%).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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, displacement ellipsoids are drawn at the 30% probability level.

(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetramethyl-2-oxoperhydronaphtho[2,1-b]furan-7-yl acetate top

Crystal data top

C₁₈H₂₈O₄	F(000) = 336
M_r = 308.40	D_x = 1.230 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7613 reflections
a = 10.1935 (5) Å	θ = 3.3–27.5°
b = 7.3226 (3) Å	µ = 0.09 mm⁻¹
c = 11.3056 (4) Å	T = 153 K
β = 99.2940 (1)°	Block, colourless
V = 832.81 (6) Å³	0.60 × 0.54 × 0.47 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1943 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.018
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −13→13
8195 measured reflections	k = −9→9
2046 independent reflections	l = −14→12

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0526P)² + 0.1209P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
2046 reflections	Δρ_max = 0.20 e Å⁻³
205 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.065 (6)

Crystal data top

C₁₈H₂₈O₄	V = 832.81 (6) Å³
M_r = 308.40	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.1935 (5) Å	µ = 0.09 mm⁻¹
b = 7.3226 (3) Å	T = 153 K
c = 11.3056 (4) Å	0.60 × 0.54 × 0.47 mm
β = 99.2940 (1)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1943 reflections with I > 2σ(I)
8195 measured reflections	R_int = 0.018
2046 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	1 restraint
wR(F²) = 0.086	H-atom parameters constrained
S = 0.99	Δρ_max = 0.20 e Å⁻³
2046 reflections	Δρ_min = −0.15 e Å⁻³
205 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	0.15453 (13)	0.2174 (2)	0.55280 (13)	0.0477 (4)
O2	0.10361 (18)	0.3434 (4)	0.37252 (14)	0.0809 (6)
O3	0.78754 (11)	0.58869 (17)	0.86839 (11)	0.0377 (3)
O4	0.77677 (15)	0.8581 (2)	0.96045 (15)	0.0599 (4)
C1	0.44238 (16)	0.6709 (2)	0.70097 (15)	0.0344 (3)
H1A	0.4104	0.7464	0.6295	0.041*
H1B	0.4025	0.7199	0.7687	0.041*
C2	0.59341 (16)	0.6859 (2)	0.73086 (15)	0.0370 (4)
H2A	0.6341	0.6395	0.6630	0.044*
H2B	0.6194	0.8154	0.7443	0.044*
C3	0.64282 (15)	0.5757 (2)	0.84229 (14)	0.0301 (3)
H3	0.6051	0.6290	0.9110	0.036*
C4	0.60784 (14)	0.3708 (2)	0.83267 (13)	0.0280 (3)
C5	0.45489 (14)	0.3533 (2)	0.78539 (13)	0.0259 (3)
H5	0.4102	0.3959	0.8529	0.031*
C6	0.40994 (16)	0.1550 (2)	0.76243 (16)	0.0360 (4)
H6A	0.4350	0.1121	0.6861	0.043*
H6B	0.4551	0.0762	0.8277	0.043*
C7	0.25934 (17)	0.1404 (3)	0.75616 (17)	0.0427 (4)
H7A	0.2310	0.0175	0.7257	0.051*
H7B	0.2388	0.1502	0.8386	0.051*
C8	0.17711 (15)	0.2812 (3)	0.67859 (15)	0.0386 (4)
C9	0.24142 (15)	0.4709 (3)	0.66974 (15)	0.0345 (3)
H9	0.2175	0.5507	0.7348	0.041*
C10	0.39595 (14)	0.4729 (2)	0.67643 (13)	0.0275 (3)
C11	0.1657 (2)	0.5373 (3)	0.54912 (19)	0.0482 (5)
H11A	0.0824	0.6003	0.5595	0.058*
H11B	0.2210	0.6213	0.5093	0.058*
C12	0.13711 (18)	0.3637 (4)	0.47870 (18)	0.0523 (5)
C13	0.43749 (17)	0.4084 (3)	0.55821 (14)	0.0384 (4)
H13A	0.5347	0.4090	0.5663	0.046*
H13B	0.4000	0.4909	0.4932	0.046*
H13C	0.4043	0.2844	0.5399	0.046*
C14	0.03976 (18)	0.2954 (4)	0.7163 (2)	0.0566 (6)
H14A	−0.0028	0.1750	0.7102	0.068*
H14B	−0.0153	0.3816	0.6635	0.068*
H14C	0.0494	0.3388	0.7993	0.068*
C15	0.84029 (17)	0.7424 (3)	0.92062 (16)	0.0399 (4)
C16	0.98747 (19)	0.7482 (3)	0.9221 (2)	0.0523 (5)
H16A	1.0279	0.8355	0.9830	0.063*
H16B	1.0056	0.7864	0.8432	0.063*
H16C	1.0252	0.6266	0.9411	0.063*
C17	0.69680 (16)	0.2695 (3)	0.75667 (16)	0.0395 (4)
H17A	0.6594	0.1485	0.7353	0.047*
H17B	0.7863	0.2562	0.8028	0.047*
H17C	0.7014	0.3393	0.6835	0.047*
C18	0.63524 (17)	0.2918 (3)	0.96055 (16)	0.0410 (4)
H18A	0.7252	0.3255	0.9987	0.049*
H18B	0.6274	0.1585	0.9569	0.049*
H18C	0.5705	0.3412	1.0074	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0391 (7)	0.0550 (9)	0.0468 (7)	−0.0076 (6)	0.0003 (5)	−0.0144 (6)
O2	0.0773 (11)	0.1122 (17)	0.0453 (8)	−0.0063 (12)	−0.0140 (7)	−0.0085 (11)
O3	0.0267 (6)	0.0346 (6)	0.0499 (7)	−0.0043 (5)	0.0006 (5)	−0.0051 (5)
O4	0.0517 (8)	0.0469 (8)	0.0773 (10)	−0.0032 (7)	−0.0014 (7)	−0.0222 (8)
C1	0.0347 (8)	0.0271 (7)	0.0390 (8)	0.0021 (7)	−0.0014 (6)	0.0043 (6)
C2	0.0352 (8)	0.0283 (8)	0.0455 (9)	−0.0064 (7)	0.0008 (6)	0.0055 (7)
C3	0.0243 (7)	0.0283 (8)	0.0365 (8)	−0.0006 (6)	0.0017 (5)	−0.0027 (6)
C4	0.0223 (6)	0.0265 (7)	0.0347 (7)	0.0003 (6)	0.0027 (5)	−0.0008 (6)
C5	0.0233 (6)	0.0255 (7)	0.0291 (7)	0.0001 (5)	0.0050 (5)	−0.0019 (6)
C6	0.0320 (8)	0.0273 (8)	0.0477 (9)	−0.0029 (7)	0.0039 (7)	0.0012 (7)
C7	0.0347 (9)	0.0406 (10)	0.0529 (10)	−0.0109 (8)	0.0072 (7)	0.0021 (8)
C8	0.0267 (7)	0.0466 (10)	0.0418 (9)	−0.0057 (7)	0.0039 (6)	−0.0079 (8)
C9	0.0268 (7)	0.0371 (9)	0.0382 (8)	0.0044 (7)	0.0006 (6)	−0.0045 (7)
C10	0.0267 (6)	0.0274 (7)	0.0278 (7)	0.0006 (6)	0.0026 (5)	−0.0010 (6)
C11	0.0353 (9)	0.0544 (12)	0.0501 (11)	0.0060 (8)	−0.0077 (8)	0.0034 (9)
C12	0.0358 (9)	0.0719 (14)	0.0454 (10)	−0.0014 (10)	−0.0050 (7)	−0.0045 (11)
C13	0.0367 (8)	0.0486 (10)	0.0301 (7)	−0.0023 (7)	0.0060 (6)	−0.0045 (7)
C14	0.0300 (8)	0.0750 (15)	0.0665 (12)	−0.0064 (10)	0.0132 (8)	−0.0086 (12)
C15	0.0383 (8)	0.0364 (9)	0.0415 (8)	−0.0063 (7)	−0.0041 (7)	0.0003 (8)
C16	0.0373 (9)	0.0492 (11)	0.0660 (12)	−0.0129 (9)	−0.0051 (8)	−0.0014 (10)
C17	0.0290 (7)	0.0357 (9)	0.0551 (10)	0.0030 (7)	0.0107 (7)	−0.0073 (8)
C18	0.0372 (8)	0.0409 (9)	0.0419 (9)	0.0002 (7)	−0.0021 (6)	0.0117 (7)

Geometric parameters (Å, º) top

O1—C12	1.354 (3)	C7—H7B	0.9900
O1—C8	1.479 (2)	C8—C14	1.532 (2)
O2—C12	1.203 (2)	C8—C9	1.546 (3)
O3—C15	1.343 (2)	C9—C11	1.534 (2)
O3—C3	1.4601 (18)	C9—C10	1.565 (2)
O4—C15	1.197 (3)	C9—H9	1.0000
C1—C2	1.526 (2)	C10—C13	1.540 (2)
C1—C10	1.536 (2)	C11—C12	1.504 (3)
C1—H1A	0.9900	C11—H11A	0.9900
C1—H1B	0.9900	C11—H11B	0.9900
C2—C3	1.512 (2)	C13—H13A	0.9800
C2—H2A	0.9900	C13—H13B	0.9800
C2—H2B	0.9900	C13—H13C	0.9800
C3—C4	1.542 (2)	C14—H14A	0.9800
C3—H3	1.0000	C14—H14B	0.9800
C4—C17	1.537 (2)	C14—H14C	0.9800
C4—C18	1.540 (2)	C15—C16	1.498 (2)
C4—C5	1.5696 (18)	C16—H16A	0.9800
C5—C6	1.532 (2)	C16—H16B	0.9800
C5—C10	1.551 (2)	C16—H16C	0.9800
C5—H5	1.0000	C17—H17A	0.9800
C6—C7	1.529 (2)	C17—H17B	0.9800
C6—H6A	0.9900	C17—H17C	0.9800
C6—H6B	0.9900	C18—H18A	0.9800
C7—C8	1.516 (3)	C18—H18B	0.9800
C7—H7A	0.9900	C18—H18C	0.9800

C12—O1—C8	109.23 (16)	C8—C9—C10	116.08 (13)
C15—O3—C3	117.60 (13)	C11—C9—H9	108.8
C2—C1—C10	112.21 (13)	C8—C9—H9	108.8
C2—C1—H1A	109.2	C10—C9—H9	108.8
C10—C1—H1A	109.2	C1—C10—C13	109.04 (14)
C2—C1—H1B	109.2	C1—C10—C5	108.73 (11)
C10—C1—H1B	109.2	C13—C10—C5	112.98 (13)
H1A—C1—H1B	107.9	C1—C10—C9	107.23 (13)
C3—C2—C1	109.55 (13)	C13—C10—C9	111.77 (12)
C3—C2—H2A	109.8	C5—C10—C9	106.90 (12)
C1—C2—H2A	109.8	C12—C11—C9	103.26 (17)
C3—C2—H2B	109.8	C12—C11—H11A	111.1
C1—C2—H2B	109.8	C9—C11—H11A	111.1
H2A—C2—H2B	108.2	C12—C11—H11B	111.1
O3—C3—C2	108.86 (13)	C9—C11—H11B	111.1
O3—C3—C4	106.99 (12)	H11A—C11—H11B	109.1
C2—C3—C4	114.73 (13)	O2—C12—O1	120.5 (2)
O3—C3—H3	108.7	O2—C12—C11	129.2 (3)
C2—C3—H3	108.7	O1—C12—C11	110.28 (15)
C4—C3—H3	108.7	C10—C13—H13A	109.5
C17—C4—C18	108.03 (14)	C10—C13—H13B	109.5
C17—C4—C3	111.00 (13)	H13A—C13—H13B	109.5
C18—C4—C3	107.13 (13)	C10—C13—H13C	109.5
C17—C4—C5	114.41 (13)	H13A—C13—H13C	109.5
C18—C4—C5	107.97 (12)	H13B—C13—H13C	109.5
C3—C4—C5	108.02 (12)	C8—C14—H14A	109.5
C6—C5—C10	109.50 (12)	C8—C14—H14B	109.5
C6—C5—C4	112.88 (12)	H14A—C14—H14B	109.5
C10—C5—C4	117.40 (12)	C8—C14—H14C	109.5
C6—C5—H5	105.3	H14A—C14—H14C	109.5
C10—C5—H5	105.3	H14B—C14—H14C	109.5
C4—C5—H5	105.3	O4—C15—O3	123.78 (16)
C7—C6—C5	110.17 (14)	O4—C15—C16	125.24 (18)
C7—C6—H6A	109.6	O3—C15—C16	110.98 (17)
C5—C6—H6A	109.6	C15—C16—H16A	109.5
C7—C6—H6B	109.6	C15—C16—H16B	109.5
C5—C6—H6B	109.6	H16A—C16—H16B	109.5
H6A—C6—H6B	108.1	C15—C16—H16C	109.5
C8—C7—C6	115.88 (15)	H16A—C16—H16C	109.5
C8—C7—H7A	108.3	H16B—C16—H16C	109.5
C6—C7—H7A	108.3	C4—C17—H17A	109.5
C8—C7—H7B	108.3	C4—C17—H17B	109.5
C6—C7—H7B	108.3	H17A—C17—H17B	109.5
H7A—C7—H7B	107.4	C4—C17—H17C	109.5
O1—C8—C7	109.08 (16)	H17A—C17—H17C	109.5
O1—C8—C14	106.37 (14)	H17B—C17—H17C	109.5
C7—C8—C14	109.27 (17)	C4—C18—H18A	109.5
O1—C8—C9	102.92 (14)	C4—C18—H18B	109.5
C7—C8—C9	116.62 (13)	H18A—C18—H18B	109.5
C14—C8—C9	111.92 (17)	C4—C18—H18C	109.5
C11—C9—C8	100.65 (14)	H18A—C18—H18C	109.5
C11—C9—C10	113.45 (15)	H18B—C18—H18C	109.5

C10—C1—C2—C3	−60.61 (18)	C14—C8—C9—C11	−77.70 (18)
C15—O3—C3—C2	77.96 (18)	O1—C8—C9—C10	−86.75 (15)
C15—O3—C3—C4	−157.52 (14)	C7—C8—C9—C10	32.6 (2)
C1—C2—C3—O3	178.97 (13)	C14—C8—C9—C10	159.43 (15)
C1—C2—C3—C4	59.15 (18)	C2—C1—C10—C13	−68.69 (16)
O3—C3—C4—C17	−45.26 (17)	C2—C1—C10—C5	54.89 (17)
C2—C3—C4—C17	75.59 (16)	C2—C1—C10—C9	170.13 (13)
O3—C3—C4—C18	72.47 (15)	C6—C5—C10—C1	−179.85 (13)
C2—C3—C4—C18	−166.68 (13)	C4—C5—C10—C1	−49.46 (17)
O3—C3—C4—C5	−171.45 (11)	C6—C5—C10—C13	−58.66 (16)
C2—C3—C4—C5	−50.60 (17)	C4—C5—C10—C13	71.73 (17)
C17—C4—C5—C6	51.22 (18)	C6—C5—C10—C9	64.69 (15)
C18—C4—C5—C6	−69.07 (17)	C4—C5—C10—C9	−164.91 (13)
C3—C4—C5—C6	175.39 (13)	C11—C9—C10—C1	79.44 (17)
C17—C4—C5—C10	−77.59 (18)	C8—C9—C10—C1	−164.68 (14)
C18—C4—C5—C10	162.11 (14)	C11—C9—C10—C13	−40.0 (2)
C3—C4—C5—C10	46.57 (17)	C8—C9—C10—C13	75.88 (18)
C10—C5—C6—C7	−65.31 (17)	C11—C9—C10—C5	−164.10 (15)
C4—C5—C6—C7	161.90 (13)	C8—C9—C10—C5	−48.22 (17)
C5—C6—C7—C8	47.1 (2)	C8—C9—C11—C12	−31.47 (18)
C12—O1—C8—C7	−152.81 (14)	C10—C9—C11—C12	93.22 (18)
C12—O1—C8—C14	89.45 (19)	C8—O1—C12—O2	−172.27 (18)
C12—O1—C8—C9	−28.36 (17)	C8—O1—C12—C11	7.91 (19)
C6—C7—C8—O1	84.82 (18)	C9—C11—C12—O2	−163.8 (2)
C6—C7—C8—C14	−159.28 (17)	C9—C11—C12—O1	16.0 (2)
C6—C7—C8—C9	−31.1 (2)	C3—O3—C15—O4	9.9 (3)
O1—C8—C9—C11	36.12 (16)	C3—O3—C15—C16	−170.25 (14)
C7—C8—C9—C11	155.46 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2ⁱ	0.98	2.55	3.383 (3)	143

Symmetry code: (i) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₈O₄
M_r	308.40
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	153
a, b, c (Å)	10.1935 (5), 7.3226 (3), 11.3056 (4)
β (°)	99.2940 (1)
V (Å³)	832.81 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.54 × 0.47

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8195, 2046, 1943
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.086, 0.99
No. of reflections	2046
No. of parameters	205
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2ⁱ	0.98	2.55	3.383 (3)	143.2

Symmetry code: (i) −x+1, y+1/2, −z+1.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant No. 20572107) and by Chengdu Municipal Bureau of Science and Technology.

References

Bhattacharyya, K., Kar, T., Bocelli, G., Banerjee, S. & Mondal, N. B. (2006). Acta Cryst. E62, o4007–o4009. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choudhary, M. I., Musharaff, S. G., Sami, A. & Atta-ur-Rahman (2004). Helv. Chim. Acta, 87, 2685–2694. Google Scholar
Devi, S. S., Malathi, R., Rajan, S. S., Aravind, S., Krishnakumari, G. N. & Ravikumar, K. (2004). Acta Cryst. E60, o117–o119. Web of Science CSD CrossRef IUCr Journals Google Scholar
Quideau, S., Lebon, M. & Lamidey, A.-M. (2002). Org. Lett. 4, 3975–3978. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, H.-J., Li, B.-G., Cai, X.-H., Qi, H.-Y., Luo, Y.-G. & Zhang, G.-L. (2006). J. Nat. Prod. 69, 1531–1538. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 64| Part 9| September 2008| Page o1765

doi:10.1107/S1600536808025737

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

(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetra­methyl-2-oxoperhydro­naphtho[2,1-b]furan-7-yl acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetramethyl-2-oxoperhydronaphtho[2,1-b]furan-7-yl acetate