Methyl 2-(4a,8-Dimethyl-7-oxodeca-hydro-naphthalen-2-yl)acrylate.

The title compound, C(16)H(24)O(3), was isolated from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The mol-ecule contains two fused (trans) six-membered rings which both exibit a chair conformation. In the crystal, mol-ecules are linked into chains along [100] by weak C-H⋯O hydrogen bonds involving the methyl and carbonyl groups.

Related literature

For the synthesis of the title compound, 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 ▶). 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

C16H24O3

M = 264.35

Tetragonal,

a = 7.3359 (1) Å

c = 54.7419 (13) Å

V = 2945.96 (9) Å3

Z = 8

Cu Kα radiation

μ = 0.64 mm−1

T = 180 K

0.48 × 0.24 × 0.18 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.737, T max = 1.000

11562 measured reflections

2319 independent reflections

2286 reflections with I > 2σ(I)

R int = 0.027

θmax = 62.0°

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.22

2319 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029303/fj2573sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029303/fj2573Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029303/fj2573Isup3.cml

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

C16H24O3	Dx = 1.192 Mg m−3
Mr = 264.35	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P41212	Cell parameters from 6272 reflections
Hall symbol: P 4abw 2nw	θ = 3.2–61.9°
a = 7.3359 (1) Å	µ = 0.64 mm−1
c = 54.7419 (13) Å	T = 180 K
V = 2945.96 (9) Å3	Box, colorless
Z = 8	0.48 × 0.24 × 0.18 mm
F(000) = 1152

Agilent Xcalibur Eos Gemini ultra diffractometer	2319 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2286 reflections with I > 2σ(I)
Miror monochromator	Rint = 0.027
Detector resolution: 16.1978 pixels mm-1	θmax = 62.0°, θmin = 3.2°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −7→8
Tmin = 0.737, Tmax = 1.000	l = −61→62
11562 measured reflections

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0378P)2 + 1.4663P] where P = (Fo2 + 2Fc2)/3
S = 1.22	(Δ/σ)max < 0.001
2319 reflections	Δρmax = 0.15 e Å−3
176 parameters	Δρmin = −0.13 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: 0.0079 (4)

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.

	x	y	z	Uiso*/Ueq
C1	1.0927 (3)	0.8703 (3)	0.07690 (4)	0.0245 (5)
H1A	1.2083	0.8472	0.0849	0.029*
H1B	1.0311	0.9671	0.0857	0.029*
C2	1.1272 (3)	0.9311 (3)	0.05053 (4)	0.0261 (5)
H2	1.1913	0.8313	0.0423	0.031*
C3	0.9461 (3)	0.9583 (4)	0.03717 (4)	0.0342 (6)
H3A	0.8808	1.0594	0.0445	0.041*
H3B	0.9699	0.9887	0.0202	0.041*
C4	0.8288 (3)	0.7880 (4)	0.03835 (4)	0.0368 (6)
H4A	0.8897	0.6905	0.0296	0.044*
H4B	0.7139	0.8118	0.0302	0.044*
C4A	0.7903 (3)	0.7247 (3)	0.06465 (4)	0.0293 (5)
C5	0.6931 (4)	0.5403 (4)	0.06370 (4)	0.0413 (6)
H5A	0.7621	0.4583	0.0533	0.050*
H5B	0.5739	0.5567	0.0564	0.050*
C6	0.6696 (4)	0.4520 (4)	0.08907 (4)	0.0406 (6)
H6A	0.5858	0.5240	0.0988	0.049*
H6B	0.6188	0.3307	0.0873	0.049*
C7	0.8502 (3)	0.4407 (3)	0.10176 (4)	0.0300 (5)
C8	0.9541 (3)	0.6181 (3)	0.10379 (3)	0.0265 (5)
H8	0.8789	0.7032	0.1132	0.032*
C8A	0.9762 (3)	0.6979 (3)	0.07764 (4)	0.0234 (5)
H8A	1.0423	0.6059	0.0682	0.028*
C9	1.2453 (3)	1.0976 (3)	0.04836 (4)	0.0247 (5)
C10	1.3641 (3)	1.1046 (3)	0.02623 (4)	0.0286 (5)
C11	0.6688 (3)	0.8646 (4)	0.07742 (4)	0.0395 (6)
H11A	0.5602	0.8834	0.0680	0.059*
H11B	0.7334	0.9778	0.0790	0.059*
H11C	0.6364	0.8205	0.0933	0.059*
C12	1.1327 (3)	0.5938 (3)	0.11736 (4)	0.0354 (6)
H12A	1.1111	0.5291	0.1323	0.053*
H12B	1.1839	0.7112	0.1210	0.053*
H12C	1.2161	0.5257	0.1074	0.053*
C13	1.2460 (3)	1.2350 (3)	0.06410 (4)	0.0344 (6)
H13A	1.3205	1.3355	0.0613	0.041*
H13B	1.1721	1.2308	0.0779	0.041*
C14	1.5954 (4)	1.2590 (4)	0.00496 (4)	0.0429 (7)
H14A	1.6742	1.1545	0.0051	0.064*
H14B	1.6673	1.3680	0.0062	0.064*
H14C	1.5271	1.2611	−0.0100	0.064*
O1	0.9105 (2)	0.2973 (2)	0.10919 (3)	0.0385 (4)
O2	1.3651 (3)	0.9897 (3)	0.01066 (3)	0.0601 (6)
O3	1.4716 (2)	1.2492 (2)	0.02541 (3)	0.0393 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0237 (12)	0.0234 (12)	0.0265 (10)	−0.0016 (9)	−0.0015 (9)	−0.0006 (9)
C2	0.0271 (13)	0.0245 (12)	0.0267 (10)	−0.0025 (9)	0.0026 (9)	−0.0036 (9)
C3	0.0344 (14)	0.0428 (15)	0.0254 (10)	−0.0081 (11)	−0.0019 (10)	0.0071 (10)
C4	0.0315 (14)	0.0503 (16)	0.0287 (11)	−0.0116 (12)	−0.0069 (10)	0.0017 (11)
C4A	0.0221 (12)	0.0352 (13)	0.0307 (11)	−0.0037 (10)	−0.0012 (9)	0.0018 (10)
C5	0.0332 (15)	0.0448 (16)	0.0459 (14)	−0.0175 (12)	−0.0064 (11)	0.0034 (12)
C6	0.0326 (15)	0.0385 (15)	0.0507 (14)	−0.0120 (12)	−0.0002 (11)	0.0078 (12)
C7	0.0321 (13)	0.0284 (13)	0.0297 (10)	−0.0008 (11)	0.0103 (9)	0.0010 (10)
C8	0.0272 (12)	0.0267 (12)	0.0256 (10)	0.0021 (10)	0.0031 (9)	0.0001 (9)
C8A	0.0225 (11)	0.0218 (12)	0.0257 (10)	0.0006 (9)	0.0022 (8)	−0.0025 (8)
C9	0.0242 (12)	0.0223 (12)	0.0275 (10)	0.0004 (10)	0.0007 (8)	0.0010 (9)
C10	0.0312 (13)	0.0230 (12)	0.0316 (11)	−0.0036 (10)	0.0012 (9)	−0.0016 (9)
C11	0.0239 (13)	0.0462 (16)	0.0483 (14)	0.0076 (12)	0.0026 (11)	0.0121 (12)
C12	0.0369 (14)	0.0326 (14)	0.0367 (12)	−0.0039 (11)	−0.0062 (10)	0.0078 (10)
C13	0.0333 (13)	0.0310 (13)	0.0389 (12)	−0.0066 (11)	0.0098 (10)	−0.0038 (11)
C14	0.0352 (14)	0.0504 (17)	0.0430 (14)	−0.0076 (13)	0.0161 (11)	0.0028 (12)
O1	0.0422 (11)	0.0254 (10)	0.0479 (9)	−0.0015 (8)	0.0084 (8)	0.0057 (7)
O2	0.0819 (16)	0.0494 (12)	0.0490 (10)	−0.0310 (11)	0.0323 (10)	−0.0215 (10)
O3	0.0392 (10)	0.0375 (10)	0.0411 (9)	−0.0152 (8)	0.0162 (7)	−0.0061 (7)

C1—C8A	1.527 (3)	C7—O1	1.211 (3)
C1—C2	1.532 (3)	C7—C8	1.512 (3)
C1—H1A	0.9700	C8—C12	1.517 (3)
C1—H1B	0.9700	C8—C8A	1.555 (3)
C2—C9	1.502 (3)	C8—H8	0.9800
C2—C3	1.529 (3)	C8A—H8A	0.9800
C2—H2	0.9800	C9—C13	1.326 (3)
C3—C4	1.519 (3)	C9—C10	1.493 (3)
C3—H3A	0.9700	C10—O2	1.199 (3)
C3—H3B	0.9700	C10—O3	1.322 (3)
C4—C4A	1.539 (3)	C11—H11A	0.9600
C4—H4A	0.9700	C11—H11B	0.9600
C4—H4B	0.9700	C11—H11C	0.9600
C4A—C11	1.529 (3)	C12—H12A	0.9600
C4A—C5	1.530 (3)	C12—H12B	0.9600
C4A—C8A	1.551 (3)	C12—H12C	0.9600
C5—C6	1.542 (3)	C13—H13A	0.9300
C5—H5A	0.9700	C13—H13B	0.9300
C5—H5B	0.9700	C14—O3	1.443 (3)
C6—C7	1.498 (3)	C14—H14A	0.9600
C6—H6A	0.9700	C14—H14B	0.9600
C6—H6B	0.9700	C14—H14C	0.9600
C8A—C1—C2	111.03 (17)	O1—C7—C8	122.6 (2)
C8A—C1—H1A	109.4	C6—C7—C8	115.6 (2)
C2—C1—H1A	109.4	C7—C8—C12	111.72 (19)
C8A—C1—H1B	109.4	C7—C8—C8A	107.99 (17)
C2—C1—H1B	109.4	C12—C8—C8A	113.89 (18)
H1A—C1—H1B	108.0	C7—C8—H8	107.7
C9—C2—C3	110.93 (19)	C12—C8—H8	107.7
C9—C2—C1	114.00 (17)	C8A—C8—H8	107.7
C3—C2—C1	110.20 (18)	C1—C8A—C4A	112.01 (17)
C9—C2—H2	107.1	C1—C8A—C8	113.25 (17)
C3—C2—H2	107.1	C4A—C8A—C8	112.22 (17)
C1—C2—H2	107.1	C1—C8A—H8A	106.2
C4—C3—C2	111.4 (2)	C4A—C8A—H8A	106.2
C4—C3—H3A	109.4	C8—C8A—H8A	106.2
C2—C3—H3A	109.4	C13—C9—C10	119.9 (2)
C4—C3—H3B	109.4	C13—C9—C2	124.7 (2)
C2—C3—H3B	109.4	C10—C9—C2	115.42 (18)
H3A—C3—H3B	108.0	O2—C10—O3	122.4 (2)
C3—C4—C4A	113.09 (18)	O2—C10—C9	123.8 (2)
C3—C4—H4A	109.0	O3—C10—C9	113.80 (18)
C4A—C4—H4A	109.0	C4A—C11—H11A	109.5
C3—C4—H4B	109.0	C4A—C11—H11B	109.5
C4A—C4—H4B	109.0	H11A—C11—H11B	109.5
H4A—C4—H4B	107.8	C4A—C11—H11C	109.5
C11—C4A—C5	109.7 (2)	H11A—C11—H11C	109.5
C11—C4A—C4	109.4 (2)	H11B—C11—H11C	109.5
C5—C4A—C4	108.70 (19)	C8—C12—H12A	109.5
C11—C4A—C8A	112.85 (18)	C8—C12—H12B	109.5
C5—C4A—C8A	108.26 (19)	H12A—C12—H12B	109.5
C4—C4A—C8A	107.80 (18)	C8—C12—H12C	109.5
C4A—C5—C6	113.1 (2)	H12A—C12—H12C	109.5
C4A—C5—H5A	109.0	H12B—C12—H12C	109.5
C6—C5—H5A	109.0	C9—C13—H13A	120.0
C4A—C5—H5B	109.0	C9—C13—H13B	120.0
C6—C5—H5B	109.0	H13A—C13—H13B	120.0
H5A—C5—H5B	107.8	O3—C14—H14A	109.5
C7—C6—C5	110.0 (2)	O3—C14—H14B	109.5
C7—C6—H6A	109.7	H14A—C14—H14B	109.5
C5—C6—H6A	109.7	O3—C14—H14C	109.5
C7—C6—H6B	109.7	H14A—C14—H14C	109.5
C5—C6—H6B	109.7	H14B—C14—H14C	109.5
H6A—C6—H6B	108.2	C10—O3—C14	116.22 (19)
O1—C7—C6	121.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2i	0.96	2.54	3.113 (3)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O2i	0.96	2.54	3.113 (3)	118

Symmetry code: (i) .