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

Moumou, M.; Benharref, A.; Daran, J.C.; Mellouki, F.; Berraho, M.

doi:10.1107/S1600536812000165

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o386

doi:10.1107/S1600536812000165

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

Mohamed Moumou,^a Ahmed Benharref,^a Jean Claude Daran,^b Fouad Mellouki ^c ^* and Moha Berraho ^a

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, ^bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France, and ^cLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Universite' Hassan II, Mohammedia-Casablanca 20810 Mohammedia, Morocco
^*Correspondence e-mail: mberraho@yahoo.fr

(Received 18 December 2011; accepted 3 January 2012; online 14 January 2012)

The title compound, C₁₅H₁₈O₃, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.0^2,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The seven-membered ring of the title compound shows a chair conformation, while the five-membered rings exibit different conformations, viz a twisted one for the lactone ring and an envelope conformation for the other five-membered ring with the C atom closest to the hydroxy group forming the flap. In the crystal, O—H⋯O hydrogen bonds connect molecules into dimers that are interconnected by C—H⋯O interactions, producing supramolecular chains along the b axis.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996 ); Bellakhdar (1997 ); El Hassany et al. (2004 ); Qureshi et al. (1990 ). For the reactivity of this sesquiterpene, see: El Haib et al. (2011 ) For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₁₈O₃
M_r = 246.29
Monoclinic, C 2
a = 15.6732 (9) Å
b = 7.4208 (4) Å
c = 11.0544 (6) Å
β = 103.169 (6)°
V = 1251.90 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 180 K
0.42 × 0.19 × 0.12 mm

Data collection

Agilent Xcalibur Eos Gemini Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.631, T_max = 1.000
13492 measured reflections
1378 independent reflections
1313 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.05
1378 reflections
166 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	2.31	3.128 (2)	171
C8—H8B⋯O1ⁱⁱ	0.97	2.58	3.500 (2)	158
C7—H7⋯O1ⁱⁱⁱ	0.98	2.65	3.579 (2)	159
Symmetry codes: (i) -x+2, y, -z+2; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+2]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000165/im2349sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000165/im2349Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000165/im2349Isup3.cml

checkCIF report

Comment top

Anvillea radiata is a plant that grows in northern Africa and particularly found in the two Maghreb countries, Morocco and Algeria. This plant is used in traditional local medicine for the treatment of dysentery, gastric-intestinal disorders (Bellakhdar, 1997), hypoglycemic activity (Qureshi et al., 1990), and has been reported to have antitumoral activity (Abdel Sattar et al., 1996). In our study of different Moroccan endemic plants, we have demonstrated that the aerial parts of Anvillea radiata could be used as a renewable source of 9-hydroxyparthenolide (El Hassany, et al., 2004). In order to prepare products with high added value that can be used in pharmacology and cosmetics industry, we studied the chemical reactivity of this major constituent of Anvillea radiata. Thus, treatment of this sesquiterpene with Bi(OTf)₃ in dichloromethane (El Haib et al., 2011) leads to the litle compound with a yield of 60%. The crystal structure of (I) is reported herein.

The molecule contains three fused rings which exhibit different conformations. The molecular structure of (I), Fig.1, shows the lactone ring to adopt a twisted conformation, as indicated by Cremer & Pople (1975) puckering parameters Q = 0.2747 (18) Å and ϕ = 59.0 (4)° while the other five-membered ring displays an envelope conformation with Q = 0.291 (2)Å and ϕ = 290.3 (4)°. The seven-membered ring has a chair conformation with QT = 0.5793 (16) Å, θ2 = 16.44 (20)°, ϕ2 = -139.46 (75)° and ϕ3 =107.00 (25). In the crystal structure, molecules are connected by O—H···O hydrogen bonds connecting molecules into dimers that again are interconnected by C—H···O interactions to produce infinite chains along b axis (Table 1).

Related literature top

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996); Bellakhdar (1997); El Hassany et al. (2004); Qureshi et al. (1990). For the reactivity of this sesquiterpene, see: El Haib et al. (2011) For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

Bi(OTf)₃(39 mg, 6 x 10^–2 mmol) was added to a stirred solution of 9β- hydroxyparthenolide (600 mg, 2.27 mmol) in dichloromethane (10 ml). The reaction mixture is left stirring for three hours at room temperature. After completion of the reaction, a saturated solution of NaHCO₃ was added and the resulting mixture is extracted three times (3 x 20 mL) with dichloromethane. The organic phases are combined and dried over Na₂SO₄ and evaporated under vacuum. Chromatography of the residue obtained on a column of silica gel eluting with hexane - ethyl acetate (85/15) allowed the isolation of the title compound (334 mg, 1.35 mmol) with a yield of 60%. Recrystallization from ethyl acetate at room temperature yielded single crystals of the title compound.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick,2008); program(s) used to refine structure: SHELXL97 (Sheldrick,2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. : Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. : Partial packing view showing the O–H···O hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

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

Crystal data top

C₁₅H₁₈O₃	F(000) = 528
M_r = 246.29	D_x = 1.307 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 9785 reflections
a = 15.6732 (9) Å	θ = 3–26.4°
b = 7.4208 (4) Å	µ = 0.09 mm⁻¹
c = 11.0544 (6) Å	T = 180 K
β = 103.169 (6)°	Box, pale yellow
V = 1251.90 (12) Å³	0.42 × 0.19 × 0.12 mm
Z = 4

Data collection top

Agilent Xcalibur Eos Gemini Ultra diffractometer	1378 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.2632 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→9
T_min = 0.631, T_max = 1.000	l = −13→13
13492 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0581P)² + 0.1945P] where P = (F_o² + 2F_c²)/3
1378 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₅H₁₈O₃	V = 1251.90 (12) Å³
M_r = 246.29	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 15.6732 (9) Å	µ = 0.09 mm⁻¹
b = 7.4208 (4) Å	T = 180 K
c = 11.0544 (6) Å	0.42 × 0.19 × 0.12 mm
β = 103.169 (6)°

Data collection top

Agilent Xcalibur Eos Gemini Ultra diffractometer	1378 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1313 reflections with I > 2σ(I)
T_min = 0.631, T_max = 1.000	R_int = 0.029
13492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
1378 reflections	Δρ_min = −0.15 e Å⁻³
166 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies, 2010)

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 > 2σ(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
C1	0.80721 (11)	0.4633 (2)	0.61618 (14)	0.0267 (3)
C2	0.87339 (12)	0.4573 (3)	0.55907 (15)	0.0380 (4)
H2	0.8666	0.4746	0.4741	0.046*
C3	0.95947 (12)	0.4201 (4)	0.64549 (17)	0.0455 (5)
H3A	1.0049	0.4976	0.6278	0.055*
H3B	0.9766	0.2953	0.6399	0.055*
C4	0.94229 (10)	0.4614 (3)	0.77340 (14)	0.0322 (4)
C5	0.84280 (10)	0.4259 (2)	0.75363 (14)	0.0246 (3)
H5	0.8353	0.2968	0.7666	0.030*
C6	0.79591 (9)	0.5247 (2)	0.83742 (14)	0.0233 (3)
H6	0.7950	0.6540	0.8192	0.028*
C7	0.70300 (10)	0.4572 (2)	0.82786 (14)	0.0265 (3)
H7	0.7016	0.3276	0.8106	0.032*
C8	0.63569 (11)	0.5483 (3)	0.72710 (16)	0.0338 (4)
H8A	0.5782	0.5047	0.7319	0.041*
H8B	0.6372	0.6766	0.7443	0.041*
C9	0.64585 (11)	0.5222 (3)	0.59733 (16)	0.0323 (4)
H9	0.5935	0.5305	0.5378	0.039*
C10	0.71551 (11)	0.4891 (2)	0.54969 (14)	0.0287 (4)
C11	0.69280 (10)	0.4841 (2)	0.95746 (15)	0.0283 (3)
C12	0.78211 (11)	0.4836 (2)	1.03860 (15)	0.0290 (3)
C13	0.62238 (13)	0.5135 (3)	1.00137 (19)	0.0401 (5)
H13A	0.6280	0.5349	1.0857	0.048*
H13B	0.5672	0.5129	0.9479	0.048*
C14	0.70133 (13)	0.4837 (3)	0.41040 (15)	0.0402 (4)
H14A	0.6403	0.5011	0.3734	0.060*
H14B	0.7198	0.3690	0.3855	0.060*
H14C	0.7348	0.5777	0.3835	0.060*
C15	0.96829 (12)	0.6516 (3)	0.81170 (19)	0.0416 (5)
H15A	0.9542	0.6767	0.8901	0.062*
H15B	0.9371	0.7335	0.7501	0.062*
H15C	1.0302	0.6660	0.8194	0.062*
O1	0.80505 (9)	0.4767 (2)	1.14968 (11)	0.0415 (3)
O2	0.84070 (7)	0.49325 (18)	0.96669 (9)	0.0290 (3)
O3	0.98840 (8)	0.3361 (2)	0.86299 (13)	0.0437 (4)
H3	1.0346	0.3813	0.9005	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0301 (8)	0.0277 (8)	0.0211 (7)	0.0032 (7)	0.0037 (6)	−0.0003 (7)
C2	0.0369 (9)	0.0543 (12)	0.0231 (7)	0.0066 (10)	0.0078 (7)	0.0013 (9)
C3	0.0317 (9)	0.0765 (16)	0.0308 (9)	0.0111 (10)	0.0126 (7)	0.0002 (9)
C4	0.0201 (7)	0.0513 (11)	0.0253 (7)	0.0084 (8)	0.0054 (6)	0.0037 (8)
C5	0.0222 (7)	0.0281 (8)	0.0230 (7)	0.0048 (6)	0.0039 (5)	0.0012 (6)
C6	0.0211 (7)	0.0267 (8)	0.0215 (7)	0.0020 (6)	0.0038 (5)	0.0009 (6)
C7	0.0219 (7)	0.0281 (8)	0.0299 (8)	0.0012 (6)	0.0066 (6)	0.0011 (7)
C8	0.0204 (7)	0.0410 (10)	0.0386 (10)	0.0043 (7)	0.0037 (7)	0.0056 (8)
C9	0.0241 (8)	0.0351 (10)	0.0325 (8)	−0.0005 (7)	−0.0044 (6)	0.0052 (7)
C10	0.0316 (8)	0.0247 (8)	0.0258 (7)	0.0001 (7)	−0.0018 (6)	0.0015 (7)
C11	0.0298 (8)	0.0238 (8)	0.0337 (8)	0.0013 (7)	0.0122 (6)	0.0021 (7)
C12	0.0336 (8)	0.0276 (8)	0.0282 (8)	0.0031 (8)	0.0122 (6)	−0.0002 (7)
C13	0.0361 (9)	0.0428 (11)	0.0471 (10)	0.0010 (8)	0.0218 (8)	0.0011 (9)
C14	0.0467 (10)	0.0422 (11)	0.0261 (8)	0.0043 (10)	−0.0030 (7)	0.0002 (8)
C15	0.0245 (8)	0.0556 (12)	0.0437 (10)	−0.0066 (8)	0.0054 (7)	0.0022 (10)
O1	0.0481 (7)	0.0523 (8)	0.0255 (6)	0.0011 (7)	0.0114 (5)	−0.0005 (6)
O2	0.0244 (5)	0.0407 (7)	0.0218 (5)	0.0026 (5)	0.0049 (4)	−0.0002 (5)
O3	0.0232 (6)	0.0660 (10)	0.0394 (7)	0.0125 (6)	0.0021 (5)	0.0152 (7)

Geometric parameters (Å, º) top

C1—C2	1.332 (2)	C8—C9	1.492 (3)
C1—C10	1.470 (2)	C8—H8A	0.9700
C1—C5	1.520 (2)	C8—H8B	0.9700
C2—C3	1.491 (2)	C9—C10	1.339 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.530 (2)	C10—C14	1.505 (2)
C3—H3A	0.9700	C11—C13	1.321 (2)
C3—H3B	0.9700	C11—C12	1.481 (2)
C4—O3	1.429 (2)	C12—O1	1.199 (2)
C4—C15	1.503 (3)	C12—O2	1.3464 (19)
C4—C5	1.547 (2)	C13—H13A	0.9300
C5—C6	1.498 (2)	C13—H13B	0.9300
C5—H5	0.9800	C14—H14A	0.9600
C6—O2	1.4602 (18)	C14—H14B	0.9600
C6—C7	1.520 (2)	C14—H14C	0.9600
C6—H6	0.9800	C15—H15A	0.9600
C7—C11	1.491 (2)	C15—H15B	0.9600
C7—C8	1.508 (2)	C15—H15C	0.9600
C7—H7	0.9800	O3—H3	0.8200

C2—C1—C10	123.05 (14)	C9—C8—C7	116.23 (15)
C2—C1—C5	108.64 (14)	C9—C8—H8A	108.2
C10—C1—C5	128.16 (14)	C7—C8—H8A	108.2
C1—C2—C3	113.02 (14)	C9—C8—H8B	108.2
C1—C2—H2	123.5	C7—C8—H8B	108.2
C3—C2—H2	123.5	H8A—C8—H8B	107.4
C2—C3—C4	103.37 (14)	C10—C9—C8	132.66 (15)
C2—C3—H3A	111.1	C10—C9—H9	113.7
C4—C3—H3A	111.1	C8—C9—H9	113.7
C2—C3—H3B	111.1	C9—C10—C1	128.26 (14)
C4—C3—H3B	111.1	C9—C10—C14	117.63 (15)
H3A—C3—H3B	109.1	C1—C10—C14	114.06 (15)
O3—C4—C15	110.74 (15)	C13—C11—C12	122.10 (16)
O3—C4—C3	110.03 (16)	C13—C11—C7	131.05 (16)
C15—C4—C3	110.80 (17)	C12—C11—C7	106.76 (13)
O3—C4—C5	108.76 (15)	O1—C12—O2	121.41 (15)
C15—C4—C5	113.55 (15)	O1—C12—C11	129.93 (15)
C3—C4—C5	102.67 (13)	O2—C12—C11	108.66 (13)
C6—C5—C1	114.13 (13)	C11—C13—H13A	120.0
C6—C5—C4	116.75 (13)	C11—C13—H13B	120.0
C1—C5—C4	103.81 (12)	H13A—C13—H13B	120.0
C6—C5—H5	107.2	C10—C14—H14A	109.5
C1—C5—H5	107.2	C10—C14—H14B	109.5
C4—C5—H5	107.2	H14A—C14—H14B	109.5
O2—C6—C5	109.43 (12)	C10—C14—H14C	109.5
O2—C6—C7	104.76 (11)	H14A—C14—H14C	109.5
C5—C6—C7	113.14 (13)	H14B—C14—H14C	109.5
O2—C6—H6	109.8	C4—C15—H15A	109.5
C5—C6—H6	109.8	C4—C15—H15B	109.5
C7—C6—H6	109.8	H15A—C15—H15B	109.5
C11—C7—C8	116.08 (14)	C4—C15—H15C	109.5
C11—C7—C6	101.53 (12)	H15A—C15—H15C	109.5
C8—C7—C6	113.67 (14)	H15B—C15—H15C	109.5
C11—C7—H7	108.4	C12—O2—C6	110.23 (12)
C8—C7—H7	108.4	C4—O3—H3	109.5
C6—C7—H7	108.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	2.31	3.128 (2)	171
C8—H8B···O1ⁱⁱ	0.97	2.58	3.500 (2)	158
C7—H7···O1ⁱⁱⁱ	0.98	2.65	3.579 (2)	159

Symmetry codes: (i) −x+2, y, −z+2; (ii) −x+3/2, y+1/2, −z+2; (iii) −x+3/2, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈O₃
M_r	246.29
Crystal system, space group	Monoclinic, C2
Temperature (K)	180
a, b, c (Å)	15.6732 (9), 7.4208 (4), 11.0544 (6)
β (°)	103.169 (6)
V (Å³)	1251.90 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.42 × 0.19 × 0.12

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.631, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13492, 1378, 1313
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.05
No. of reflections	1378
No. of parameters	166
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.15

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick,2008), SHELXL97 (Sheldrick,2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	2.31	3.128 (2)	171
C8—H8B···O1ⁱⁱ	0.97	2.58	3.500 (2)	158
C7—H7···O1ⁱⁱⁱ	0.98	2.65	3.579 (2)	159

Symmetry codes: (i) −x+2, y, −z+2; (ii) −x+3/2, y+1/2, −z+2; (iii) −x+3/2, y−1/2, −z+2.

Acknowledgements

The authors thank Professor El Ammari for useful discussions.

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Volume 68| Part 2| February 2012| Page o386

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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