1-[(2R,4aR,8R,8aR)-8-Hy­droxy-4a,8-di­methyl­perhydronaphthalen-2-yl]ethan-1-one

Tebbaa, M.; Benharref, A.; Berraho, M.; Daran, J.-C.; Akssira, M.; Elhakmaoui, A.

doi:10.1107/S1600536811004454

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o601

doi:10.1107/S1600536811004454

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1-[(2R,4aR,8R,8aR)-8-Hydroxy-4a,8-dimethylperhydronaphthalen-2-yl]ethan-1-one

Mohamed Tebbaa,^a Ahmed Benharref,^b Moha Berraho,^b Jean-Claude Daran,^c Mohamed Akssira ^a and Ahmed Elhakmaoui ^a ^*

^aLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia–Casablanca 20810 Mohammedia, Morocco, ^bLaboratoire de Chimie Biomoleculaire, Substances Naturelles et Réactivité, URAC16, Université Cadi Ayyad, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, and ^cLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
^*Correspondence e-mail: makssira@yahoo.fr

(Received 1 February 2011; accepted 6 February 2011; online 12 February 2011)

The title compound, C₁₄H₂₄O₂, was synthesized from ilicic acid, which was isolated from the aerial part of Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter]. The molecule contains two fused six-membered rings, which both display a chair conformation. In the crystal, molecules are linked into chains propagating along the b axis by intermolecular O—H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Barrero et al. (2009 ). For the medicinal interest in Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter], see: Shtacher & Kasshman, (1970 ); Bohlmann et al. (1977 ); Chiappini et al. (1982 ) and for the pharmacological interest, see: Azoulay et al. (1986 ); Bohlmann et al. (1977); Ceccherelli et al. (1988 ). For background to phytochemical studies of plants, see: Geissman & Toribio (1967 ). For conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₄H₂₄O₂
M_r = 224.33
Monoclinic, P 2₁
a = 6.4919 (7) Å
b = 9.4057 (9) Å
c = 10.3638 (11) Å
β = 97.286 (10)°
V = 627.71 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 180 K
0.6 × 0.25 × 0.15 mm

Data collection

Agilent Eos Gemini Ultra diffractometer
6571 measured reflections
1362 independent reflections
1262 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.119
S = 1.09
1362 reflections
152 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H2⋯O2ⁱ	0.84 (3)	2.05 (3)	2.883 (2)	169 (3)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+2]$ .

Data collection: CrysAlis PRO (Agilent, 2010 ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXL97 (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/S1600536811004454/fj2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004454/fj2393Isup2.hkl

checkCIF report

Comment top

The ilicic acid is one of the main components of the extracts of the aerial parts Inula viscose. This natural acid is a major constituent of the dichloromethane extract of the Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter]. This plant is widespread in Mediterranean area and extends to the Atlantic cost of Morocco. It is a well known medicinal plant (Shtacher & Kasshman, 1970; Chiappini et al., 1982) and has some pharmacological activities (Azoulay et al., 1986). the Inula Viscosa (L) Aiton has been the subject of chemical investigation in terms of isolating sesquiterpene lactones (Bohlmann et al., 1977), sesquiterpene acids (Ceccherelli et al., 1988; Geissman et al.1967). The literature report one article on the transformation of the ilicic acid (Barrero et al., 2009). In order to prepare products with high added value, used in the industry pharmacological or cosmetic, we have studied the reactivity of this acid. Thus, with the reaction Curtius, we synthesized the title compound(1R, 2R, 6R, 9R)-9-acethyl-2,6-dimethylbicyclo [4.4.0]decan-2-ol) with à yield 50%. The structure of this new derivative of ilicic acid was determined by NMR spectral analysis of 1H, 13 C and mass spectroscopy and confirmed by its single-crystal X-ray structure. The molecule is built up from two fused six-membered rings. The molecular structure of (I),Fig.1, shows the two rings to adopt a perfect chair conformation as indicated by Cremer & Pople (1975) puckering parameters Q(T)= 0.554 (2)Å and spherical polar angle θ = 178.1 (2)° with ϕ = 36 (7)° for the first ring (C1,C2··· C6) and Q(T)= 0.597 (2)Å with a spherical polar angle θ = 178.71 (19)° and ϕ = 108 (5)° for the second ring (C1, C6···C10)(Cremer and Pople,1975). In the crystal structure, molecules are linked into chains (Fig. 2) running along the b axis by intermolecular O—H···O hydrogen bonds (Table 1) involving the O1 and O2 atoms.

Related literature top

For the synthesis, see: Barrero et al. (2009). For the medicinal interest in Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter], see: Shtacher & Kasshman, (1970); Bohlmann et al. (1977); Chiappini et al. (1982) and for the pharmacological interest, see: Azoulay et al. (1986); Bohlmann et al. (1977); Ceccherelli et al. (1988). For background to phytochemical studies of plants, see: Geissman et al. (1967). For conformational analysis, see: Cremer & Pople (1975).

Experimental top

A solution containing the ilicic acid 1 g (3.96 mmol) and Et3N 0.82 ml (5.895 mmol) in dry THF (100 ml) was cooled at -10 °C. Ethyl chloroformate 0,56 ml (5.95 mm l) was added dropwise and the reaction mixture was stirred at this temperature for 1 h. A solution of NaN3 0.43 g (6.74 mmol) in H2O (10 ml) was then added in one portion. After 1.5 h at 0 °C, the resulting heterogeous mixture was filttered, the organic solvent was removed under reduced pressure and the aqueous phase was extracted tree time with ether (3 × 50 ml). The combined organic layers were dried over MgSO4, and concentrated in vacuo. The crude acyl-azide was then dissolved in toluene (50 ml) and the resulting solution was refluxed for 1 h. Then a solution of hydrochloric acid at 10% was added to the reaction mixture which is remized at reflux for 2 h. After extraction, the organic phase is washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The product was purified by column chromatography over silica gel (hexane/ethyl acetate 95/5). The title compound was recrystallized in dichloromethane.

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: SHELXL97 (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 the atom-labelling scheme. Displacement ellipsoids are 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 interactions (dashed lines)and the formation of a chain parallel to the b axis. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i)1 - x,-1/2 + y,-z + 2]

1-[(2R,4aR,8R,8aR)-8-Hydroxy-4a,8- dimethylperhydronaphthalen-2-yl]ethan-1-one top

Crystal data top

C₁₄H₂₄O₂	F(000) = 248
M_r = 224.33	D_x = 1.187 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6571 reflections
a = 6.4919 (7) Å	θ = 2.9–26.4°
b = 9.4057 (9) Å	µ = 0.08 mm⁻¹
c = 10.3638 (11) Å	T = 180 K
β = 97.286 (10)°	Prism, colourless
V = 627.71 (11) Å³	0.6 × 0.25 × 0.15 mm
Z = 2

Data collection top

Agilent Eos Gemini Ultra diffractometer	1262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.047
Graphite monochromator	θ_max = 26.4°, θ_min = 2.9°
Detector resolution: 16.1978 pixels mm^-1	h = −8→8
ϕ and ω scans	k = −11→11
6571 measured reflections	l = −12→12
1362 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0935P)² + 0.0033P] where P = (F_o² + 2F_c²)/3
1362 reflections	(Δ/σ)_max < 0.001
152 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₂₄O₂	V = 627.71 (11) Å³
M_r = 224.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.4919 (7) Å	µ = 0.08 mm⁻¹
b = 9.4057 (9) Å	T = 180 K
c = 10.3638 (11) Å	0.6 × 0.25 × 0.15 mm
β = 97.286 (10)°

Data collection top

Agilent Eos Gemini Ultra diffractometer	1262 reflections with I > 2σ(I)
6571 measured reflections	R_int = 0.047
1362 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.28 e Å⁻³
1362 reflections	Δρ_min = −0.24 e Å⁻³
152 parameters

Special details top

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
H2	0.822 (5)	0.709 (4)	0.829 (3)	0.039 (8)*
C1	0.8653 (3)	0.9919 (2)	0.80775 (19)	0.0185 (4)
H1	0.9924	0.9851	0.8695	0.022*
C2	0.8777 (3)	0.8642 (2)	0.7154 (2)	0.0214 (4)
C3	1.0704 (3)	0.8816 (2)	0.6454 (2)	0.0261 (5)
H3A	1.1934	0.8693	0.7081	0.031*
H3B	1.0705	0.8072	0.5806	0.031*
C4	1.0826 (3)	1.0251 (3)	0.5791 (2)	0.0296 (5)
H4A	0.9684	1.0339	0.5095	0.036*
H4B	1.2114	1.0311	0.5411	0.036*
C5	1.0729 (3)	1.1462 (2)	0.6757 (2)	0.0269 (5)
H5A	1.0766	1.2360	0.6300	0.032*
H5B	1.1947	1.1420	0.7403	0.032*
C6	0.8776 (3)	1.1420 (2)	0.7452 (2)	0.0220 (5)
C7	0.9014 (4)	1.2512 (2)	0.8558 (2)	0.0262 (5)
H7A	1.0348	1.2372	0.9079	0.031*
H7B	0.9008	1.3459	0.8186	0.031*
C8	0.7305 (4)	1.2420 (2)	0.9442 (2)	0.0267 (5)
H8A	0.5973	1.2638	0.8945	0.032*
H8B	0.7565	1.3112	1.0137	0.032*
C9	0.7245 (3)	1.0926 (2)	1.0020 (2)	0.0225 (4)
H9	0.8596	1.0737	1.0527	0.027*
C10	0.6895 (3)	0.9817 (2)	0.89272 (19)	0.0208 (4)
H10A	0.6867	0.8871	0.9298	0.025*
H10B	0.5572	0.9987	0.8402	0.025*
C11	0.6816 (3)	0.8367 (3)	0.6205 (2)	0.0281 (5)
H11A	0.5633	0.8342	0.6674	0.042*
H11B	0.6942	0.7472	0.5776	0.042*
H11C	0.6643	0.9114	0.5570	0.042*
C12	0.6859 (4)	1.1824 (3)	0.6488 (2)	0.0291 (5)
H12A	0.6890	1.1314	0.5688	0.044*
H12B	0.6873	1.2827	0.6321	0.044*
H12C	0.5619	1.1581	0.6854	0.044*
C13	0.5607 (4)	1.0824 (2)	1.0919 (2)	0.0254 (5)
C14	0.6262 (4)	1.0246 (3)	1.2248 (2)	0.0365 (6)
H14A	0.5094	1.0239	1.2732	0.055*
H14B	0.7341	1.0832	1.2688	0.055*
H14C	0.6770	0.9293	1.2181	0.055*
O1	0.9229 (2)	0.73764 (16)	0.79125 (15)	0.0258 (4)
O2	0.3823 (3)	1.1216 (2)	1.05879 (17)	0.0368 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0181 (9)	0.0150 (9)	0.0221 (10)	0.0001 (7)	0.0013 (7)	0.0000 (7)
C2	0.0234 (11)	0.0173 (9)	0.0236 (10)	0.0027 (8)	0.0035 (8)	0.0001 (8)
C3	0.0265 (11)	0.0247 (11)	0.0283 (11)	0.0026 (8)	0.0079 (8)	−0.0005 (9)
C4	0.0300 (11)	0.0311 (12)	0.0299 (11)	−0.0018 (9)	0.0119 (9)	0.0033 (9)
C5	0.0256 (11)	0.0237 (11)	0.0322 (11)	−0.0027 (8)	0.0065 (8)	0.0053 (9)
C6	0.0200 (10)	0.0188 (10)	0.0269 (10)	−0.0005 (7)	0.0017 (7)	0.0025 (8)
C7	0.0299 (11)	0.0163 (10)	0.0319 (11)	−0.0033 (8)	0.0016 (9)	−0.0003 (8)
C8	0.0308 (11)	0.0180 (10)	0.0309 (11)	0.0017 (9)	0.0024 (9)	−0.0025 (8)
C9	0.0258 (10)	0.0185 (10)	0.0229 (10)	0.0003 (8)	0.0026 (8)	−0.0020 (7)
C10	0.0236 (10)	0.0149 (9)	0.0241 (10)	0.0001 (8)	0.0040 (7)	−0.0014 (7)
C11	0.0253 (11)	0.0266 (11)	0.0321 (11)	−0.0011 (8)	0.0024 (9)	−0.0068 (9)
C12	0.0298 (12)	0.0263 (11)	0.0304 (11)	0.0037 (9)	0.0003 (9)	0.0055 (9)
C13	0.0325 (12)	0.0149 (9)	0.0296 (11)	0.0006 (8)	0.0070 (8)	−0.0058 (8)
C14	0.0463 (14)	0.0321 (13)	0.0324 (12)	−0.0030 (11)	0.0097 (10)	0.0025 (10)
O1	0.0279 (8)	0.0172 (7)	0.0341 (8)	0.0036 (6)	0.0103 (6)	0.0028 (6)
O2	0.0336 (9)	0.0360 (10)	0.0429 (9)	0.0095 (7)	0.0132 (7)	0.0005 (8)

Geometric parameters (Å, º) top

C1—C10	1.530 (3)	C8—C9	1.530 (3)
C1—C2	1.545 (3)	C8—H8A	0.9700
C1—C6	1.560 (3)	C8—H8B	0.9700
C1—H1	0.9800	C9—C13	1.503 (3)
C2—O1	1.436 (3)	C9—C10	1.535 (3)
C2—C11	1.529 (3)	C9—H9	0.9800
C2—C3	1.532 (3)	C10—H10A	0.9700
C3—C4	1.521 (3)	C10—H10B	0.9700
C3—H3A	0.9700	C11—H11A	0.9600
C3—H3B	0.9700	C11—H11B	0.9600
C4—C5	1.524 (3)	C11—H11C	0.9600
C4—H4A	0.9700	C12—H12A	0.9600
C4—H4B	0.9700	C12—H12B	0.9600
C5—C6	1.536 (3)	C12—H12C	0.9600
C5—H5A	0.9700	C13—O2	1.222 (3)
C5—H5B	0.9700	C13—C14	1.493 (3)
C6—C7	1.533 (3)	C14—H14A	0.9600
C6—C12	1.541 (3)	C14—H14B	0.9600
C7—C8	1.528 (3)	C14—H14C	0.9600
C7—H7A	0.9700	O1—H2	0.85 (3)
C7—H7B	0.9700

C10—C1—C2	114.14 (16)	H7A—C7—H7B	107.7
C10—C1—C6	112.18 (15)	C7—C8—C9	110.07 (17)
C2—C1—C6	115.90 (15)	C7—C8—H8A	109.6
C10—C1—H1	104.3	C9—C8—H8A	109.6
C2—C1—H1	104.3	C7—C8—H8B	109.6
C6—C1—H1	104.3	C9—C8—H8B	109.6
O1—C2—C11	107.93 (18)	H8A—C8—H8B	108.2
O1—C2—C3	103.02 (16)	C13—C9—C8	110.87 (17)
C11—C2—C3	112.14 (17)	C13—C9—C10	111.32 (17)
O1—C2—C1	109.18 (15)	C8—C9—C10	110.12 (16)
C11—C2—C1	115.19 (16)	C13—C9—H9	108.1
C3—C2—C1	108.64 (17)	C8—C9—H9	108.1
C4—C3—C2	113.69 (17)	C10—C9—H9	108.1
C4—C3—H3A	108.8	C1—C10—C9	109.28 (15)
C2—C3—H3A	108.8	C1—C10—H10A	109.8
C4—C3—H3B	108.8	C9—C10—H10A	109.8
C2—C3—H3B	108.8	C1—C10—H10B	109.8
H3A—C3—H3B	107.7	C9—C10—H10B	109.8
C3—C4—C5	110.96 (17)	H10A—C10—H10B	108.3
C3—C4—H4A	109.4	C2—C11—H11A	109.5
C5—C4—H4A	109.4	C2—C11—H11B	109.5
C3—C4—H4B	109.4	H11A—C11—H11B	109.5
C5—C4—H4B	109.4	C2—C11—H11C	109.5
H4A—C4—H4B	108.0	H11A—C11—H11C	109.5
C4—C5—C6	113.21 (17)	H11B—C11—H11C	109.5
C4—C5—H5A	108.9	C6—C12—H12A	109.5
C6—C5—H5A	108.9	C6—C12—H12B	109.5
C4—C5—H5B	108.9	H12A—C12—H12B	109.5
C6—C5—H5B	108.9	C6—C12—H12C	109.5
H5A—C5—H5B	107.7	H12A—C12—H12C	109.5
C7—C6—C5	108.80 (16)	H12B—C12—H12C	109.5
C7—C6—C12	108.44 (18)	O2—C13—C14	121.2 (2)
C5—C6—C12	109.67 (17)	O2—C13—C9	121.8 (2)
C7—C6—C1	107.52 (17)	C14—C13—C9	117.03 (19)
C5—C6—C1	107.90 (16)	C13—C14—H14A	109.5
C12—C6—C1	114.38 (18)	C13—C14—H14B	109.5
C8—C7—C6	113.48 (17)	H14A—C14—H14B	109.5
C8—C7—H7A	108.9	C13—C14—H14C	109.5
C6—C7—H7A	108.9	H14A—C14—H14C	109.5
C8—C7—H7B	108.9	H14B—C14—H14C	109.5
C6—C7—H7B	108.9	C2—O1—H2	113 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2···O2ⁱ	0.84 (3)	2.05 (3)	2.883 (2)	169 (3)

Symmetry code: (i) −x+1, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₄O₂
M_r	224.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	180
a, b, c (Å)	6.4919 (7), 9.4057 (9), 10.3638 (11)
β (°)	97.286 (10)
V (Å³)	627.71 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.6 × 0.25 × 0.15

Data collection
Diffractometer	Agilent Eos Gemini Ultra diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6571, 1362, 1262
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.119, 1.09
No. of reflections	1362
No. of parameters	152
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24

Computer programs: CrysAlis PRO (Agilent, 2010), 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
O1—H2···O2ⁱ	0.84 (3)	2.05 (3)	2.883 (2)	169 (3)

Symmetry code: (i) −x+1, y−1/2, −z+2.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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Volume 67| Part 3| March 2011| Page o601

doi:10.1107/S1600536811004454

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

1-[(2R,4aR,8R,8aR)-8-Hy­dr­oxy-4a,8-di­methyl­perhydronaphthalen-2-yl]ethan-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[(2R,4aR,8R,8aR)-8-Hydroxy-4a,8-dimethylperhydronaphthalen-2-yl]ethan-1-one