(1R,2S,4S,4aS,8S,8aS)-4-Hy­droxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexa­hydro-1H-4a,1-(ep­oxy­methano)­naphthalen-2-yl acetate

Selaïmia-Ferdjani, O.; Bidjou-Haiour, C.; Planchat, A.; Pipelier, M.

doi:10.1107/S1600536813013524

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o938-o939

doi:10.1107/S1600536813013524

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(1R,2S,4S,4aS,8S,8aS)-4-Hydroxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-2-yl acetate

Ouassila Selaïmia-Ferdjani,^a,^b Chahra Bidjou-Haiour,^a Aurelien Planchat ^b and Muriel Pipelier ^b ^*

^aLaboratoire de Synthèse Organique Modélisation et Optimisation des Procédés Chimiques, Université Badji-Mokhtar Annaba, BP12, 23000 Annaba, Algeria, and ^bUniversité de Nantes, CNRS, Laboratoire CEISAM-UMR 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France
^*Correspondence e-mail: muriel.pipelier@univ-nantes.fr

(Received 13 May 2013; accepted 16 May 2013; online 22 May 2013)

The title compound, C₁₅H₂₀O₅, presents a bisnorsesquiterpene skeleton, with a trans-decaline backbone constrained by the lactone bridge. The α-hydroxy substituent and the methyl group belonging to the two decaline rings are in axial positions, whereas the other methyl group and the acyl group occupy the sterically preferred equatorial positions. The molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond. In the crystal, molecules are linked into chains along [010] by O—H⋯O hydrogen bonds

Related literature

For the synthesis, see: Selaimia-Ferdjani et al. (2013 ). For the biological activity of the natural lactone Paralemnolide A analogue of the title compound, see: Wang et al. (2012 ) and of related nardosinane sesquiterpene derivatives, see: Bishara et al. (2008 ); Huang et al. (2011 ); Petit et al. (2004 ); Lu et al. (2011 ). For related nardosinane sesquiterpenes whose biological activity has not been investigated, see: El-Gamal et al. (2005 ); Huang et al. (2006 ); Wang & Duh (2007 ); Wang et al. (2010 ).

Experimental

Crystal data

C₁₅H₂₀O₅
M_r = 280.3
Monoclinic, P 2₁
a = 10.3312 (10) Å
b = 7.1692 (8) Å
c = 10.8502 (6) Å
β = 115.958 (5)°
V = 722.56 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.48 × 0.42 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: gaussian (JANA2006; Petříček et al., 2006) T_min = 0.967, T_max = 0.972
12282 measured reflections
3328 independent reflections
2774 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.138
S = 1.84
3328 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
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
C10—H3c10⋯O4	0.96	2.31	2.946 (4)	122.91
O4—H1⋯O9ⁱ	0.83 (5)	2.10 (4)	2.907 (2)	165 (4)
Symmetry code: (i) x, y+1, z.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: EVALCCD (Duisenberg et al., 2003 ); data reduction: COLLECT (Nonius, 1998); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813013524/bt6907sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013524/bt6907Isup2.hkl

checkCIF report

Comment top

Several nardosinane sesquiterpene derivatives, extracted from different soft corals (Lemnalia, Paralemnalia, Rhytisma and others), have already expressed promising biological properties (Bishara et al. 2008; Huang et al. 2011; Lu et al. 2011; Petit et al. 2004; Wang et al. 2012) while the potential of others remains to be explored (El-Gamal et al. 2005; Huang et al. 2006; Wang and Duh 2007; Wang et al. 2010). In our continuing interest in the total synthesis of biologically active compounds, we have recently proposed a synthetic strategy to access such sesquiterpene derivatives. In the course of the synthesis, the title compound appeared as an analogue structurally close to the natural lactone Paralemnolide A (Wang et al. 2012) which possesses cytotoxic activity. We report herein on the crystal structure of a new nardosinane sesquiterpene analogue.

The title compound presents a bisnorsesquiterpene skeleton, with a trans-decaline backbone constrained by the lactone bridge. The α-hydroxy substituent and the methyl group belonging to the two decaline rings are in an axial position, whereas the other methyl group and the acyl group occupy the sterically preferred equatorial position. In the crystal, the molecules form chains connected by O-H···O hydrogen bonds. The crystal structure is further stabilized by C-H···O contacts.

Related literature top

For the synthesis of the title compound, see: Selaimia-Ferdjani et al. (2013). For the biological activity of the natural lactone Paralemnolide A analogue of the title compound, see: Wang et al. (2012) and of related nardosinane sesquiterpene derivatives, see: Bishara et al. (2008); Huang et al. (2011); Petit et al. (2004); Lu et al. (2011). For related nardosinane sesquiterpenes whose biological activity has not yet been investigated, see: El-Gamal et al. (2005); Huang et al. (2006); Wang & Duh (2007); Wang et al. (2010).

Experimental top

Title compound was synthesized according to the reported method (Selaimia-Ferdjani et al., 2013): To a solution of diene 1 (100 mg, 0.38 mmol) in CH₂Cl₂ (2.5 ml) at 0°C was added via cannula a solution of mCPBA (350 mg, 0.38 mmol) in CH₂Cl₂ (5.0 ml). After 20 min, the reaction mixture was quenched with saturated NaHCO₃ solution (10 ml). The aqueous layer was extracted with CH₂Cl₂ (3 x 25 ml) then the combined organic layers were washed with brine (50 ml), dried over MgSO₄, filtered and concentrated under vacuum. The residue was purified by flash chromatography (eluant Petroleum Ether-EtOAc 100/0 to 7/3) to afford lactone 2 (title compound) (63 mg, 60%) as a solide. Crystals suitable for X-ray structure analysis (colorless crystals) were obtained by slow evaporation of a solution of the title compound in ethyl acetate/hexane (1:1, v/v) at room temperature. mp = 434 K; [α]²⁰_D= - 17 (c = 0.29 in CH₂Cl₂); ¹H NMR (400 MHz, CDCl₃) d 6.28 (ddd, J_6–5 = 10.1 Hz, J_6–7 = 4.7 Hz, J_6–7 = 1.5 Hz, 1H, H₆), 5.69 (d, J_6–5 = 10.1 Hz, 1H, H₅), 5.45 (ddd, J_2–1 = 3.1 Hz, J_3–2 = 7.2 Hz, J_3–2 = 10.4 Hz, 1H, H₂), 4.27 (d, J_4–3 = 6.6 Hz, 1H, H₄), 2.82 (d, J_2–1 = 3.1 Hz, 1H, H₁), 2.39 (m, 1H, H₃), 2.15 (s, 3H, H₁₃), 1.91–2.35 (m, 4H, H₃, H₇, H₇, H₈), 1.27 (s, 3H, H₁₀), 0.90 (d, J_8–11 = 6.5 Hz, 3H, H₁₁). MS (EI): m/z (%) = 220 (28), 124 (96), 109 (72), 95 (29), 43 (100) HRMS (ESI⁺): calcd. for [M+Na]⁺ (C₁₅H₂₀O₅Na) 303.12029, found 303.12015; elemental analysis calcd (%) C₁₅H₂₀O₅: C 64.27, H 7.19, found: C 64.24, H 7.16.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: COLLECT (Nonius, 1998); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top

	Fig. 1. Synthetic scheme to prepare title compound.
	Fig. 2. ORTEP drawing of the X-Ray crystallographic structure of the title molecule, with atom labeling. The displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius
	Fig. 3. Portion of the crystal structure showing the packing of the H–bonded infinite chains of the title compound. The intermolecular O-H···O bonds are depicted by blue lines.

(1R,2S,4S,4aS,8S,8aS)-4-Hydroxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexahydro-1H- 4a,1-(epoxymethano)naphthalen-2-yl acetate top

Crystal data top

C₁₅H₂₀O₅	Z = 2
M_r = 280.3	F(000) = 300
Monoclinic, P2₁	D_x = 1.288 Mg m⁻³
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71069 Å
a = 10.3312 (10) Å	µ = 0.10 mm⁻¹
b = 7.1692 (8) Å	T = 293 K
c = 10.8502 (6) Å	Block, colourless
β = 115.958 (5)°	0.48 × 0.42 × 0.30 mm
V = 722.56 (12) Å³

Data collection top

Nonius KappaCCD diffractometer	3328 independent reflections
Radiation source: X-ray tube	2774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
CCD, ϕ and ω frames scans	θ_max = 28.1°, θ_min = 6.5°
Absorption correction: gaussian (JANA2006; Petříček et al., 2006)	h = −13→13
T_min = 0.967, T_max = 0.972	k = −9→9
12282 measured reflections	l = −14→14

Refinement top

Refinement on F²	77 constraints
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.138	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0025000002I²)
S = 1.84	(Δ/σ)_max = 0.013
3328 reflections	Δρ_max = 0.15 e Å⁻³
185 parameters	Δρ_min = −0.12 e Å⁻³
0 restraints

Crystal data top

C₁₅H₂₀O₅	V = 722.56 (12) Å³
M_r = 280.3	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.3312 (10) Å	µ = 0.10 mm⁻¹
b = 7.1692 (8) Å	T = 293 K
c = 10.8502 (6) Å	0.48 × 0.42 × 0.30 mm
β = 115.958 (5)°

Data collection top

Nonius KappaCCD diffractometer	3328 independent reflections
Absorption correction: gaussian (JANA2006; Petříček et al., 2006)	2774 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.972	R_int = 0.049
12282 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.84	Δρ_max = 0.15 e Å⁻³
3328 reflections	Δρ_min = −0.12 e Å⁻³
185 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4a	−0.24245 (17)	−0.3248 (2)	−0.96277 (13)	0.0469 (6)
O2	0.13229 (15)	−0.5347 (2)	−0.74186 (16)	0.0540 (6)
O9	−0.1870 (2)	−0.6248 (2)	−0.95660 (17)	0.0580 (7)
O4	−0.0236 (2)	0.0757 (2)	−0.7741 (2)	0.0747 (9)
O12	0.3391 (2)	−0.4418 (4)	−0.5763 (2)	0.0969 (10)
C1	−0.0910 (2)	−0.4390 (3)	−0.74640 (18)	0.0373 (6)
C2	0.0592 (2)	−0.3717 (3)	−0.7223 (2)	0.0452 (8)
C3	0.0495 (3)	−0.2237 (3)	−0.8268 (3)	0.0614 (11)
C4	−0.0719 (3)	−0.0820 (3)	−0.8628 (3)	0.0554 (10)
C5	−0.3316 (3)	−0.0382 (3)	−0.9057 (3)	0.0649 (10)
C6	−0.4264 (3)	−0.0442 (5)	−0.8551 (3)	0.0789 (12)
C7	−0.4257 (3)	−0.1856 (5)	−0.7544 (3)	0.0787 (13)
C8	−0.3245 (2)	−0.3495 (4)	−0.7387 (2)	0.0565 (9)
C9	−0.1760 (2)	−0.4802 (3)	−0.8969 (2)	0.0409 (7)
C10	−0.0991 (3)	−0.1656 (4)	−0.5957 (2)	0.0558 (9)
C11	−0.3100 (3)	−0.4779 (6)	−0.6212 (3)	0.0855 (15)
C12	0.2732 (2)	−0.5534 (3)	−0.6613 (2)	0.0504 (8)
C13	0.3297 (3)	−0.7288 (4)	−0.6924 (3)	0.0661 (11)
C8a	−0.1778 (2)	−0.2776 (3)	−0.72788 (18)	0.0400 (7)
C4a	−0.2064 (2)	−0.1689 (3)	−0.8603 (2)	0.0446 (7)
H1c5	−0.343345	0.053419	−0.97428	0.0778*
H1c6	−0.500769	0.048719	−0.885126	0.0947*
H1c7	−0.521658	−0.231528	−0.781906	0.0945*
H2c7	−0.398331	−0.127184	−0.666953	0.0945*
H1c8	−0.365931	−0.42545	−0.819637	0.0678*
H1c11	−0.262203	−0.590901	−0.625442	0.1026*
H2c11	−0.254686	−0.416546	−0.535349	0.1026*
H3c11	−0.403884	−0.507108	−0.628833	0.1026*
H1c10	−0.162091	−0.070956	−0.590084	0.0669*
H2c10	−0.070651	−0.247485	−0.518177	0.0669*
H3c10	−0.015259	−0.108038	−0.595774	0.0669*
H1c1	−0.078238	−0.541924	−0.68555	0.0448*
H1c2	0.108852	−0.317946	−0.632628	0.0543*
H1c13	0.266544	−0.830237	−0.698342	0.0793*
H2c13	0.335007	−0.715916	−0.778133	0.0793*
H3c13	0.42399	−0.753581	−0.620827	0.0793*
H1c3	0.041767	−0.283227	−0.908981	0.0736*
H2c3	0.139807	−0.159392	−0.795406	0.0736*
H1c4	−0.099131	−0.040857	−0.955087	0.0665*
H1	−0.056 (5)	0.173 (7)	−0.818 (4)	0.107 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4a	0.0587 (9)	0.0363 (7)	0.0343 (7)	−0.0011 (7)	0.0100 (6)	−0.0009 (5)
O2	0.0389 (8)	0.0493 (8)	0.0649 (9)	0.0047 (7)	0.0145 (7)	−0.0114 (8)
O9	0.0699 (11)	0.0392 (7)	0.0577 (9)	−0.0061 (8)	0.0212 (8)	−0.0126 (7)
O4	0.0777 (13)	0.0319 (8)	0.0961 (15)	−0.0112 (8)	0.0212 (11)	−0.0057 (9)
O12	0.0516 (11)	0.1034 (17)	0.1043 (16)	0.0019 (11)	0.0053 (10)	−0.0446 (15)
C1	0.0363 (9)	0.0341 (8)	0.0368 (9)	−0.0012 (8)	0.0116 (7)	0.0027 (8)
C2	0.0379 (10)	0.0385 (9)	0.0574 (12)	−0.0036 (8)	0.0191 (9)	−0.0110 (9)
C3	0.0679 (15)	0.0409 (10)	0.0914 (18)	−0.0106 (11)	0.0498 (14)	−0.0025 (12)
C4	0.0704 (16)	0.0313 (10)	0.0618 (14)	−0.0047 (10)	0.0264 (12)	0.0031 (9)
C5	0.0615 (15)	0.0462 (11)	0.0603 (14)	0.0115 (12)	0.0022 (12)	0.0025 (11)
C6	0.0530 (15)	0.0752 (17)	0.0814 (18)	0.0256 (15)	0.0043 (13)	−0.0116 (16)
C7	0.0430 (13)	0.105 (2)	0.0816 (18)	0.0144 (15)	0.0214 (12)	−0.0156 (17)
C8	0.0391 (11)	0.0744 (15)	0.0528 (12)	−0.0025 (11)	0.0171 (9)	−0.0064 (12)
C9	0.0448 (10)	0.0342 (9)	0.0414 (9)	−0.0066 (8)	0.0168 (8)	−0.0016 (8)
C10	0.0477 (12)	0.0648 (14)	0.0440 (11)	0.0048 (11)	0.0100 (9)	−0.0161 (11)
C11	0.0634 (18)	0.123 (3)	0.0822 (18)	−0.0143 (19)	0.0428 (15)	0.011 (2)
C12	0.0388 (10)	0.0562 (12)	0.0541 (12)	0.0009 (10)	0.0183 (9)	0.0023 (11)
C13	0.0491 (13)	0.0702 (15)	0.0796 (16)	0.0127 (12)	0.0289 (12)	0.0025 (14)
C8a	0.0353 (9)	0.0430 (9)	0.0351 (9)	0.0008 (8)	0.0091 (7)	−0.0031 (8)
C4a	0.0498 (11)	0.0325 (8)	0.0406 (10)	0.0004 (8)	0.0097 (8)	−0.0019 (8)

Geometric parameters (Å, º) top

O4a—C9	1.340 (2)	C5—H1c5	0.96
O4a—C4a	1.504 (2)	C6—C7	1.488 (5)
O2—C2	1.456 (3)	C6—H1c6	0.96
O2—C12	1.337 (2)	C7—C8	1.532 (4)
O9—C9	1.201 (3)	C7—H1c7	0.96
O4—C4	1.426 (3)	C7—H2c7	0.96
O4—H1	0.83 (5)	C8—C11	1.526 (5)
O12—C12	1.185 (3)	C8—C8a	1.556 (3)
C1—C2	1.535 (3)	C8—H1c8	0.96
C1—C9	1.507 (3)	C10—C8a	1.531 (3)
C1—C8a	1.530 (3)	C10—H1c10	0.96
C1—H1c1	0.96	C10—H2c10	0.96
C2—C3	1.524 (4)	C10—H3c10	0.96
C2—H1c2	0.96	C11—H1c11	0.96
C3—C4	1.526 (4)	C11—H2c11	0.96
C3—H1c3	0.96	C11—H3c11	0.96
C3—H2c3	0.96	C12—C13	1.486 (4)
C4—C4a	1.534 (4)	C13—H1c13	0.96
C4—H1c4	0.96	C13—H2c13	0.96
C5—C6	1.316 (5)	C13—H3c13	0.96
C5—C4a	1.495 (3)	C8a—C4a	1.545 (3)

C9—O4a—C4a	108.72 (13)	C7—C8—H1c8	108.87
C2—O2—C12	118.11 (17)	C11—C8—C8a	113.63 (18)
C4—O4—H1	111 (3)	C11—C8—H1c8	105.3
C2—C1—C9	108.2 (2)	C8a—C8—H1c8	106.65
C2—C1—C8a	110.30 (16)	O4a—C9—O9	121.67 (17)
C2—C1—H1c1	107.44	O4a—C9—C1	109.53 (16)
C9—C1—C8a	101.19 (14)	O9—C9—C1	128.80 (17)
C9—C1—H1c1	115.73	C8a—C10—H1c10	109.47
C8a—C1—H1c1	113.8	C8a—C10—H2c10	109.47
O2—C2—C1	105.87 (16)	C8a—C10—H3c10	109.47
O2—C2—C3	108.7 (2)	H1c10—C10—H2c10	109.47
O2—C2—H1c2	112.88	H1c10—C10—H3c10	109.47
C1—C2—C3	111.08 (17)	H2c10—C10—H3c10	109.47
C1—C2—H1c2	110.54	C8—C11—H1c11	109.47
C3—C2—H1c2	107.84	C8—C11—H2c11	109.47
C2—C3—C4	115.7 (3)	C8—C11—H3c11	109.47
C2—C3—H1c3	109.47	H1c11—C11—H2c11	109.47
C2—C3—H2c3	109.47	H1c11—C11—H3c11	109.47
C4—C3—H1c3	109.47	H2c11—C11—H3c11	109.47
C4—C3—H2c3	109.47	O2—C12—O12	122.1 (2)
H1c3—C3—H2c3	102.43	O2—C12—C13	111.11 (19)
O4—C4—C3	110.43 (19)	O12—C12—C13	126.8 (2)
O4—C4—C4a	111.3 (3)	C12—C13—H1c13	109.47
O4—C4—H1c4	108.45	C12—C13—H2c13	109.47
C3—C4—C4a	111.97 (19)	C12—C13—H3c13	109.47
C3—C4—H1c4	107.71	H1c13—C13—H2c13	109.47
C4a—C4—H1c4	106.8	H1c13—C13—H3c13	109.47
C6—C5—C4a	122.5 (3)	H2c13—C13—H3c13	109.47
C6—C5—H1c5	118.76	C1—C8a—C8	110.28 (18)
C4a—C5—H1c5	118.76	C1—C8a—C10	114.76 (15)
C5—C6—C7	124.3 (3)	C1—C8a—C4a	98.29 (18)
C5—C6—H1c6	117.87	C8—C8a—C10	110.2 (2)
C7—C6—H1c6	117.87	C8—C8a—C4a	108.26 (15)
C6—C7—C8	112.8 (3)	C10—C8a—C4a	114.46 (17)
C6—C7—H1c7	109.47	O4a—C4a—C4	102.8 (2)
C6—C7—H2c7	109.47	O4a—C4a—C5	108.89 (15)
C8—C7—H1c7	109.47	O4a—C4a—C8a	101.37 (14)
C8—C7—H2c7	109.47	C4—C4a—C5	113.57 (19)
H1c7—C7—H2c7	105.88	C4—C4a—C8a	114.52 (16)
C7—C8—C11	111.6 (3)	C5—C4a—C8a	114.1 (2)
C7—C8—C8a	110.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H1c8···C9	0.96	2.48	2.913 (4)	107.28
C10—H3c10···O4	0.96	2.31	2.946 (4)	122.91
C2—H1c2···O12	0.96	2.36	2.668 (3)	98.20
O4—H1···O9ⁱ	0.83 (5)	2.10 (4)	2.907 (2)	165 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀O₅
M_r	280.3
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	10.3312 (10), 7.1692 (8), 10.8502 (6)
β (°)	115.958 (5)
V (Å³)	722.56 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.42 × 0.30

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Gaussian (JANA2006; Petříček et al., 2006)
T_min, T_max	0.967, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	12282, 3328, 2774
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.663

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.138, 1.84
No. of reflections	3328
No. of parameters	185
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.12

Computer programs: COLLECT (Nonius, 1998), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), JANA2006 (Petříček et al., 2006), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H3c10···O4	0.96	2.31	2.946 (4)	122.91
O4—H1···O9ⁱ	0.83 (5)	2.10 (4)	2.907 (2)	165 (4)

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

Acknowledgements

The authors thank the Profas Programme for a 18 month PhD felloship for OS-F in the CEISAM laboratory at Nantes University.

References

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Volume 69| Part 6| June 2013| Pages o938-o939

doi:10.1107/S1600536813013524

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

(1R,2S,4S,4aS,8S,8aS)-4-Hy­dr­oxy-8,8a-di­methyl-10-oxo-2,3,4,7,8,8a-hexa­hydro-1H-4a,1-(ep­­oxy­methano)­naphthalen-2-yl acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1R,2S,4S,4aS,8S,8aS)-4-Hydroxy-8,8a-dimethyl-10-oxo-2,3,4,7,8,8a-hexahydro-1H-4a,1-(epoxymethano)naphthalen-2-yl acetate