Methyl 2-(8a-hy-droxy-4a-methyl-8-methyl-enedeca-hydro-naphthalen-2-yl)acrylate.

The title compound, C(16)H(24)O(3), 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 both in chair conformations. In the crystal, mol-ecules are linked into chains running parallel to the a axis by O-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Barrero et al. (2009 ▶). For the medicinal and pharmacological properties of Inula Viscosa (L) Aiton [or Dittrichia Viscosa­ (L) Greuter], see: Shtacher & Kasshman (1970 ▶); Bohlmann et al. (1977 ▶); Chiappini et al. (1982 ▶); 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

C16H24O3

M = 264.35

Orthorhombic,

a = 6.0666 (5) Å

b = 10.0900 (9) Å

c = 23.747 (2) Å

V = 1453.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.65 × 0.45 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

6831 measured reflections

1745 independent reflections

1202 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.114

S = 1.04

1745 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053712/bt5751sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053712/bt5751Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053712/bt5751Isup3.cml

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

C16H24O3	F(000) = 576
Mr = 264.35	Dx = 1.208 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6881 reflections
a = 6.0666 (5) Å	θ = 3.5–26.4°
b = 10.0900 (9) Å	µ = 0.08 mm−1
c = 23.747 (2) Å	T = 296 K
V = 1453.6 (2) Å3	Prism, colourless
Z = 4	0.65 × 0.45 × 0.26 mm

Bruker APEXII CCD diffractometer	1202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
graphite	θmax = 26.4°, θmin = 3.5°
φ and ω scans	h = −7→7
6831 measured reflections	k = −11→12
1745 independent reflections	l = −29→29

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.056P)2 + 0.0754P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
1745 reflections	Δρmax = 0.18 e Å−3
176 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

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
C1	0.1942 (5)	0.9387 (3)	0.90963 (10)	0.0356 (7)
H1A	0.0601	0.9883	0.9026	0.043*
H1B	0.1598	0.8451	0.9064	0.043*
C2	0.2754 (5)	0.9680 (3)	0.96934 (11)	0.0383 (7)
H2	0.4089	0.9153	0.9756	0.046*
C3	0.3401 (6)	1.1152 (3)	0.97421 (12)	0.0471 (8)
H3A	0.2093	1.1697	0.9702	0.056*
H3B	0.4019	1.1315	1.0112	0.056*
C4	0.5077 (5)	1.1547 (3)	0.92942 (12)	0.0443 (8)
H4A	0.6448	1.1082	0.9365	0.053*
H4B	0.5369	1.2489	0.9326	0.053*
C4A	0.4312 (5)	1.1240 (3)	0.86892 (11)	0.0347 (7)
C5	0.6221 (5)	1.1502 (3)	0.82769 (12)	0.0449 (8)
H5A	0.6604	1.2435	0.8291	0.054*
H5B	0.7500	1.1000	0.8397	0.054*
C6	0.5660 (6)	1.1129 (4)	0.76711 (13)	0.0538 (9)
H6A	0.6967	1.1222	0.7439	0.065*
H6B	0.4549	1.1733	0.7528	0.065*
C7	0.4804 (5)	0.9707 (3)	0.76277 (12)	0.0458 (8)
H7A	0.4242	0.9554	0.7251	0.055*
H7B	0.6012	0.9094	0.7691	0.055*
C8	0.3005 (5)	0.9442 (3)	0.80496 (11)	0.0364 (7)
C8A	0.3675 (4)	0.9758 (3)	0.86540 (11)	0.0323 (7)
C9	0.1081 (5)	0.9271 (3)	1.01354 (12)	0.0417 (8)
C10	0.1797 (6)	0.9201 (3)	1.07371 (12)	0.0438 (8)
C11	0.4791 (6)	0.9357 (4)	1.13715 (12)	0.0622 (10)
H11A	0.4307	1.0140	1.1565	0.093*
H11B	0.6373	0.9337	1.1364	0.093*
H11C	0.4251	0.8586	1.1564	0.093*
C12	0.2369 (5)	1.2136 (3)	0.85384 (14)	0.0507 (9)
H12A	0.2844	1.3044	0.8537	0.076*
H12B	0.1217	1.2024	0.8811	0.076*
H12C	0.1824	1.1904	0.8172	0.076*
C13	0.1041 (5)	0.8994 (3)	0.79041 (12)	0.0480 (8)
H13A	0.0723	0.8829	0.7527	0.058*
H13B	−0.0025	0.8843	0.8178	0.058*
C15	−0.0984 (6)	0.8966 (4)	1.00336 (14)	0.0586 (10)
H15A	−0.1910	0.8724	1.0328	0.070*
H15B	−0.1520	0.8992	0.9667	0.070*
O1	0.5665 (3)	0.9020 (2)	0.87737 (8)	0.0406 (5)
H1	0.5425	0.8225	0.8734	0.061*
O2	0.3955 (4)	0.9371 (2)	1.08027 (8)	0.0514 (6)
O3	0.0589 (4)	0.8972 (3)	1.11270 (9)	0.0684 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0353 (17)	0.0361 (17)	0.0354 (15)	−0.0003 (14)	0.0008 (12)	0.0014 (14)
C2	0.0363 (17)	0.0434 (19)	0.0352 (15)	−0.0013 (15)	0.0007 (12)	0.0009 (14)
C3	0.056 (2)	0.047 (2)	0.0380 (15)	−0.0083 (17)	0.0031 (15)	−0.0083 (15)
C4	0.049 (2)	0.0409 (18)	0.0430 (17)	−0.0123 (16)	−0.0021 (15)	−0.0041 (14)
C4A	0.0386 (17)	0.0309 (16)	0.0344 (13)	−0.0028 (13)	−0.0020 (13)	0.0018 (12)
C5	0.046 (2)	0.0416 (19)	0.0469 (17)	−0.0073 (16)	0.0046 (15)	0.0040 (15)
C6	0.060 (2)	0.057 (2)	0.0444 (16)	−0.0056 (19)	0.0084 (17)	0.0056 (17)
C7	0.055 (2)	0.051 (2)	0.0320 (14)	−0.0024 (17)	0.0040 (14)	−0.0020 (15)
C8	0.0417 (18)	0.0327 (17)	0.0348 (14)	0.0041 (15)	−0.0043 (13)	−0.0010 (14)
C8A	0.0308 (17)	0.0316 (16)	0.0347 (14)	0.0022 (12)	−0.0012 (12)	0.0023 (13)
C9	0.0396 (19)	0.047 (2)	0.0387 (14)	−0.0005 (16)	0.0036 (13)	−0.0008 (15)
C10	0.047 (2)	0.046 (2)	0.0386 (16)	−0.0012 (16)	0.0038 (15)	0.0002 (15)
C11	0.062 (2)	0.086 (3)	0.0396 (16)	0.001 (2)	−0.0049 (15)	−0.0004 (18)
C12	0.055 (2)	0.0378 (19)	0.059 (2)	0.0032 (16)	−0.0014 (16)	0.0036 (17)
C13	0.049 (2)	0.056 (2)	0.0389 (15)	−0.0014 (18)	−0.0085 (14)	−0.0026 (16)
C15	0.044 (2)	0.080 (3)	0.0513 (19)	−0.008 (2)	0.0048 (16)	0.0058 (19)
O1	0.0377 (12)	0.0393 (12)	0.0447 (11)	0.0068 (10)	−0.0038 (9)	0.0005 (11)
O2	0.0436 (14)	0.0750 (17)	0.0354 (10)	−0.0031 (13)	0.0001 (9)	0.0007 (12)
O3	0.0595 (16)	0.103 (2)	0.0431 (12)	−0.0137 (16)	0.0125 (11)	0.0082 (13)

C1—C2	1.530 (4)	C7—C8	1.506 (4)
C1—C8A	1.533 (4)	C7—H7A	0.9700
C1—H1A	0.9700	C7—H7B	0.9700
C1—H1B	0.9700	C8—C13	1.320 (4)
C2—C9	1.518 (4)	C8—C8A	1.525 (4)
C2—C3	1.541 (4)	C8A—O1	1.446 (3)
C2—H2	0.9800	C9—C15	1.312 (5)
C3—C4	1.524 (4)	C9—C10	1.495 (4)
C3—H3A	0.9700	C10—O3	1.203 (4)
C3—H3B	0.9700	C10—O2	1.330 (4)
C4—C4A	1.541 (4)	C11—O2	1.443 (3)
C4—H4A	0.9700	C11—H11A	0.9600
C4—H4B	0.9700	C11—H11B	0.9600
C4A—C12	1.528 (4)	C11—H11C	0.9600
C4A—C5	1.539 (4)	C12—H12A	0.9600
C4A—C8A	1.547 (4)	C12—H12B	0.9600
C5—C6	1.526 (4)	C12—H12C	0.9600
C5—H5A	0.9700	C13—H13A	0.9300
C5—H5B	0.9700	C13—H13B	0.9300
C6—C7	1.530 (5)	C15—H15A	0.9300
C6—H6A	0.9700	C15—H15B	0.9300
C6—H6B	0.9700	O1—H1	0.8200
C2—C1—C8A	111.5 (2)	C8—C7—C6	111.6 (3)
C2—C1—H1A	109.3	C8—C7—H7A	109.3
C8A—C1—H1A	109.3	C6—C7—H7A	109.3
C2—C1—H1B	109.3	C8—C7—H7B	109.3
C8A—C1—H1B	109.3	C6—C7—H7B	109.3
H1A—C1—H1B	108.0	H7A—C7—H7B	108.0
C9—C2—C1	111.9 (2)	C13—C8—C7	122.7 (3)
C9—C2—C3	112.4 (2)	C13—C8—C8A	124.0 (3)
C1—C2—C3	109.8 (2)	C7—C8—C8A	113.3 (2)
C9—C2—H2	107.5	O1—C8A—C8	107.5 (2)
C1—C2—H2	107.5	O1—C8A—C1	108.2 (2)
C3—C2—H2	107.5	C8—C8A—C1	114.2 (2)
C4—C3—C2	111.7 (2)	O1—C8A—C4A	106.2 (2)
C4—C3—H3A	109.3	C8—C8A—C4A	108.6 (2)
C2—C3—H3A	109.3	C1—C8A—C4A	111.7 (2)
C4—C3—H3B	109.3	C15—C9—C10	116.3 (3)
C2—C3—H3B	109.3	C15—C9—C2	125.1 (3)
H3A—C3—H3B	107.9	C10—C9—C2	118.7 (3)
C3—C4—C4A	113.4 (3)	O3—C10—O2	122.3 (3)
C3—C4—H4A	108.9	O3—C10—C9	124.6 (3)
C4A—C4—H4A	108.9	O2—C10—C9	113.1 (3)
C3—C4—H4B	108.9	O2—C11—H11A	109.5
C4A—C4—H4B	108.9	O2—C11—H11B	109.5
H4A—C4—H4B	107.7	H11A—C11—H11B	109.5
C12—C4A—C5	109.2 (2)	O2—C11—H11C	109.5
C12—C4A—C4	109.4 (2)	H11A—C11—H11C	109.5
C5—C4A—C4	109.4 (2)	H11B—C11—H11C	109.5
C12—C4A—C8A	111.5 (2)	C4A—C12—H12A	109.5
C5—C4A—C8A	108.6 (2)	C4A—C12—H12B	109.5
C4—C4A—C8A	108.6 (2)	H12A—C12—H12B	109.5
C6—C5—C4A	112.9 (3)	C4A—C12—H12C	109.5
C6—C5—H5A	109.0	H12A—C12—H12C	109.5
C4A—C5—H5A	109.0	H12B—C12—H12C	109.5
C6—C5—H5B	109.0	C8—C13—H13A	120.0
C4A—C5—H5B	109.0	C8—C13—H13B	120.0
H5A—C5—H5B	107.8	H13A—C13—H13B	120.0
C5—C6—C7	111.8 (3)	C9—C15—H15A	120.0
C5—C6—H6A	109.3	C9—C15—H15B	120.0
C7—C6—H6A	109.3	H15A—C15—H15B	120.0
C5—C6—H6B	109.3	C8A—O1—H1	109.5
C7—C6—H6B	109.3	C10—O2—C11	117.1 (2)
H6A—C6—H6B	107.9

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.82	2.24	3.033 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	2.24	3.033 (4)	161

Symmetry code: (i) .