1-[(2R,4aR,8R,8aR)-8-Hy-droxy-4a,8-di-methyl-perhydronaphthalen-2-yl]ethan-1-one.

The title compound, C(14)H(24)O(2), was synthesized from ilicic acid, which was isolated from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The mol-ecule contains two fused six-membered rings, which both display a chair conformation. In the crystal, mol-ecules are linked into chains propagating along the b axis by inter-molecular 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 = 224.33

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.09

1362 reflections

152 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004454/fj2393sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H24O2	F(000) = 248
Mr = 224.33	Dx = 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

Agilent Eos Gemini Ultra diffractometer	1262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
graphite	θmax = 26.4°, θmin = 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 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(Fo2) + (0.0935P)2 + 0.0033P] where P = (Fo2 + 2Fc2)/3
1362 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) .