7-[2-(3-Fur-yl)eth-yl]-7,8-dimethyl-3,5,6,6a,7,8,9,10-octa-hydro-1H-naphtho-[1,8a-c]furan-3-one.

In the title mol-ecule, C(20)H(26)O(3), a clerodane diterpenoid isolated from Dodonaea viscosa-, the trans-fused six-membered rings of the deca-line system display chair conformations. The five-membered lactone ring adopts an envelope conformation and the five-membered furan ring is essentially planar with a maximum deviation of 0.0052 (12) Å.

Related literature

For the absolute stereochemistry of the title compound from NMR and literature data, see: Jefferies & Payne (1967 ▶). For background to natural product chemistry, see: Arfan et al. (2010 ▶); Khan et al. (2005 ▶).

Experimental

Crystal data

C20H26O3

M = 314.41

Orthorhombic,

a = 9.1343 (8) Å

b = 11.8752 (10) Å

c = 15.5255 (13) Å

V = 1684.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.46 × 0.21 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.963, T max = 0.994

17210 measured reflections

2378 independent reflections

2124 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.05

2378 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶) and OLEX2 (Dolomanov et al., 2009 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶) and OLEX2; molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035373/pv2325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035373/pv2325Isup2.hkl

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

C20H26O3	F(000) = 680
Mr = 314.41	Dx = 1.240 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4592 reflections
a = 9.1343 (8) Å	θ = 2.6–25.8°
b = 11.8752 (10) Å	µ = 0.08 mm−1
c = 15.5255 (13) Å	T = 150 K
V = 1684.1 (2) Å3	Plate, colourless
Z = 4	0.46 × 0.21 × 0.08 mm

Bruker APEXII CCD diffractometer	2378 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω rotation with narrow frames scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −12→12
Tmin = 0.963, Tmax = 0.994	k = −15→15
17210 measured reflections	l = −20→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1493P] where P = (Fo2 + 2Fc2)/3
2378 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.7909 (2)	0.60429 (16)	0.47103 (12)	0.0302 (4)
H1	0.7308	0.5466	0.4945	0.036*
O1	0.90632 (16)	0.65328 (12)	0.51339 (8)	0.0364 (3)
C2	0.9617 (2)	0.73164 (17)	0.45834 (13)	0.0363 (4)
H2	1.0422	0.7795	0.4710	0.044*
C3	0.8874 (2)	0.73222 (16)	0.38386 (13)	0.0313 (4)
H3	0.9060	0.7787	0.3353	0.038*
C4	0.77393 (19)	0.64889 (14)	0.39168 (11)	0.0243 (3)
C5	0.6611 (2)	0.61806 (14)	0.32528 (11)	0.0263 (4)
H5A	0.5867	0.5685	0.3520	0.032*
H5B	0.7089	0.5754	0.2783	0.032*
C6	0.58507 (19)	0.72228 (13)	0.28730 (11)	0.0232 (3)
H6A	0.6615	0.7716	0.2624	0.028*
H6B	0.5391	0.7642	0.3353	0.028*
C7	0.46681 (18)	0.70275 (13)	0.21744 (10)	0.0205 (3)
C8	0.4031 (2)	0.82001 (13)	0.19732 (12)	0.0274 (4)
H8A	0.3394	0.8439	0.2447	0.041*
H8B	0.3461	0.8165	0.1439	0.041*
H8C	0.4831	0.8742	0.1905	0.041*
C9	0.53645 (18)	0.64730 (14)	0.13577 (10)	0.0223 (3)
H9	0.5889	0.5781	0.1557	0.027*
C10	0.6498 (2)	0.72123 (16)	0.09011 (12)	0.0310 (4)
H10A	0.6954	0.6784	0.0432	0.047*
H10B	0.7252	0.7444	0.1314	0.047*
H10C	0.6015	0.7881	0.0665	0.047*
C11	0.42124 (19)	0.60881 (15)	0.06978 (10)	0.0260 (4)
H11A	0.3736	0.6761	0.0447	0.031*
H11B	0.4713	0.5683	0.0225	0.031*
C12	0.30336 (19)	0.53222 (15)	0.10773 (10)	0.0256 (4)
H12A	0.3482	0.4606	0.1268	0.031*
H12B	0.2295	0.5147	0.0630	0.031*
C13	0.22816 (18)	0.59026 (14)	0.18497 (10)	0.0219 (3)
C14	0.34897 (18)	0.61938 (13)	0.25089 (10)	0.0194 (3)
H14	0.4034	0.5471	0.2589	0.023*
C15	0.2826 (2)	0.64366 (14)	0.33993 (10)	0.0237 (3)
H15A	0.3606	0.6675	0.3803	0.028*
H15B	0.2101	0.7053	0.3355	0.028*
C16	0.2082 (2)	0.53662 (15)	0.37365 (11)	0.0280 (4)
H16A	0.2832	0.4784	0.3853	0.034*
H16B	0.1571	0.5535	0.4284	0.034*
C17	0.1000 (2)	0.49250 (14)	0.30904 (12)	0.0281 (4)
H17	0.0218	0.4459	0.3279	0.034*
C18	0.11187 (19)	0.51761 (15)	0.22587 (11)	0.0257 (4)
C19	−0.0169 (2)	0.52032 (18)	0.16805 (12)	0.0330 (4)
O4	−0.11876 (15)	0.45656 (14)	0.15980 (10)	0.0450 (4)
O5	−0.00711 (14)	0.61773 (13)	0.12226 (9)	0.0390 (3)
C20	0.12289 (19)	0.68107 (16)	0.14996 (12)	0.0298 (4)
H20A	0.0974	0.7361	0.1955	0.036*
H20B	0.1674	0.7218	0.1009	0.036*

	U11	U22	U33	U12	U13	U23
C1	0.0278 (9)	0.0339 (9)	0.0288 (9)	0.0042 (8)	−0.0020 (7)	−0.0021 (7)
O1	0.0330 (7)	0.0472 (8)	0.0288 (6)	0.0075 (7)	−0.0079 (6)	−0.0087 (6)
C2	0.0273 (9)	0.0389 (10)	0.0426 (11)	0.0006 (8)	−0.0051 (8)	−0.0131 (9)
C3	0.0259 (8)	0.0338 (9)	0.0341 (9)	−0.0024 (8)	0.0017 (8)	−0.0050 (8)
C4	0.0216 (8)	0.0248 (8)	0.0265 (8)	0.0019 (7)	0.0001 (7)	−0.0044 (7)
C5	0.0281 (8)	0.0231 (8)	0.0277 (8)	−0.0004 (7)	−0.0053 (7)	−0.0019 (7)
C6	0.0247 (8)	0.0202 (7)	0.0245 (8)	−0.0023 (7)	−0.0018 (7)	−0.0015 (6)
C7	0.0235 (7)	0.0183 (7)	0.0196 (7)	0.0008 (6)	0.0006 (6)	0.0005 (6)
C8	0.0317 (9)	0.0192 (7)	0.0313 (9)	0.0031 (7)	0.0000 (8)	0.0022 (7)
C9	0.0239 (8)	0.0222 (7)	0.0209 (7)	0.0020 (7)	0.0008 (6)	0.0015 (6)
C10	0.0299 (9)	0.0357 (9)	0.0274 (9)	−0.0036 (8)	0.0068 (7)	0.0036 (8)
C11	0.0263 (8)	0.0331 (9)	0.0188 (7)	0.0008 (8)	0.0014 (7)	−0.0020 (7)
C12	0.0259 (8)	0.0310 (9)	0.0200 (7)	−0.0013 (7)	−0.0004 (7)	−0.0056 (7)
C13	0.0225 (8)	0.0236 (8)	0.0195 (7)	0.0014 (6)	−0.0005 (6)	−0.0016 (6)
C14	0.0208 (7)	0.0192 (7)	0.0180 (7)	0.0013 (6)	−0.0001 (6)	0.0004 (6)
C15	0.0278 (8)	0.0243 (8)	0.0190 (7)	−0.0015 (7)	0.0001 (7)	−0.0021 (6)
C16	0.0318 (9)	0.0304 (9)	0.0217 (8)	−0.0001 (8)	0.0036 (7)	0.0027 (7)
C17	0.0274 (8)	0.0258 (8)	0.0311 (8)	−0.0045 (7)	0.0064 (7)	−0.0014 (7)
C18	0.0219 (8)	0.0259 (8)	0.0293 (8)	−0.0015 (7)	0.0007 (7)	−0.0058 (7)
C19	0.0222 (8)	0.0461 (11)	0.0307 (9)	0.0012 (8)	0.0014 (8)	−0.0100 (8)
O4	0.0257 (7)	0.0606 (10)	0.0486 (8)	−0.0090 (7)	−0.0011 (7)	−0.0152 (8)
O5	0.0255 (7)	0.0542 (9)	0.0372 (7)	0.0028 (6)	−0.0079 (6)	0.0003 (7)
C20	0.0261 (9)	0.0344 (9)	0.0289 (9)	0.0061 (7)	−0.0036 (7)	0.0029 (7)

C1—C4	1.350 (3)	C10—H10C	0.9800
C1—O1	1.372 (2)	C11—C12	1.528 (2)
C1—H1	0.9500	C11—H11A	0.9900
O1—C2	1.361 (3)	C11—H11B	0.9900
C2—C3	1.341 (3)	C12—C13	1.544 (2)
C2—H2	0.9500	C12—H12A	0.9900
C3—C4	1.438 (2)	C12—H12B	0.9900
C3—H3	0.9500	C13—C18	1.509 (2)
C4—C5	1.503 (2)	C13—C20	1.544 (2)
C5—C6	1.537 (2)	C13—C14	1.544 (2)
C5—H5A	0.9900	C14—C15	1.537 (2)
C5—H5B	0.9900	C14—H14	1.0000
C6—C7	1.548 (2)	C15—C16	1.534 (2)
C6—H6A	0.9900	C15—H15A	0.9900
C6—H6B	0.9900	C15—H15B	0.9900
C7—C8	1.541 (2)	C16—C17	1.502 (3)
C7—C14	1.552 (2)	C16—H16A	0.9900
C7—C9	1.564 (2)	C16—H16B	0.9900
C8—H8A	0.9800	C17—C18	1.330 (3)
C8—H8B	0.9800	C17—H17	0.9500
C8—H8C	0.9800	C18—C19	1.480 (2)
C9—C10	1.532 (2)	C19—O4	1.207 (2)
C9—C11	1.538 (2)	C19—O5	1.361 (3)
C9—H9	1.0000	O5—C20	1.470 (2)
C10—H10A	0.9800	C20—H20A	0.9900
C10—H10B	0.9800	C20—H20B	0.9900
C4—C1—O1	111.05 (17)	C9—C11—H11A	108.8
C4—C1—H1	124.5	C12—C11—H11B	108.8
O1—C1—H1	124.5	C9—C11—H11B	108.8
C2—O1—C1	105.92 (15)	H11A—C11—H11B	107.7
C3—C2—O1	110.93 (18)	C11—C12—C13	110.32 (14)
C3—C2—H2	124.5	C11—C12—H12A	109.6
O1—C2—H2	124.5	C13—C12—H12A	109.6
C2—C3—C4	106.76 (18)	C11—C12—H12B	109.6
C2—C3—H3	126.6	C13—C12—H12B	109.6
C4—C3—H3	126.6	H12A—C12—H12B	108.1
C1—C4—C3	105.33 (16)	C18—C13—C20	96.26 (13)
C1—C4—C5	127.53 (17)	C18—C13—C14	110.63 (13)
C3—C4—C5	127.14 (16)	C20—C13—C14	121.47 (14)
C4—C5—C6	112.14 (14)	C18—C13—C12	112.63 (14)
C4—C5—H5A	109.2	C20—C13—C12	108.38 (14)
C6—C5—H5A	109.2	C14—C13—C12	107.26 (13)
C4—C5—H5B	109.2	C15—C14—C13	110.88 (13)
C6—C5—H5B	109.2	C15—C14—C7	117.05 (13)
H5A—C5—H5B	107.9	C13—C14—C7	114.63 (13)
C5—C6—C7	117.61 (13)	C15—C14—H14	104.2
C5—C6—H6A	107.9	C13—C14—H14	104.2
C7—C6—H6A	107.9	C7—C14—H14	104.2
C5—C6—H6B	107.9	C16—C15—C14	109.05 (13)
C7—C6—H6B	107.9	C16—C15—H15A	109.9
H6A—C6—H6B	107.2	C14—C15—H15A	109.9
C8—C7—C6	105.68 (13)	C16—C15—H15B	109.9
C8—C7—C14	112.47 (13)	C14—C15—H15B	109.9
C6—C7—C14	110.19 (12)	H15A—C15—H15B	108.3
C8—C7—C9	111.70 (13)	C17—C16—C15	110.66 (14)
C6—C7—C9	110.32 (13)	C17—C16—H16A	109.5
C14—C7—C9	106.55 (12)	C15—C16—H16A	109.5
C7—C8—H8A	109.5	C17—C16—H16B	109.5
C7—C8—H8B	109.5	C15—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	108.1
C7—C8—H8C	109.5	C18—C17—C16	121.11 (16)
H8A—C8—H8C	109.5	C18—C17—H17	119.4
H8B—C8—H8C	109.5	C16—C17—H17	119.4
C10—C9—C11	108.94 (14)	C17—C18—C19	121.95 (17)
C10—C9—C7	114.14 (14)	C17—C18—C13	126.47 (16)
C11—C9—C7	112.76 (13)	C19—C18—C13	106.96 (15)
C10—C9—H9	106.9	O4—C19—O5	121.90 (18)
C11—C9—H9	106.9	O4—C19—C18	131.6 (2)
C7—C9—H9	106.9	O5—C19—C18	106.47 (15)
C9—C10—H10A	109.5	C19—O5—C20	109.57 (14)
C9—C10—H10B	109.5	O5—C20—C13	104.40 (14)
H10A—C10—H10B	109.5	O5—C20—H20A	110.9
C9—C10—H10C	109.5	C13—C20—H20A	110.9
H10A—C10—H10C	109.5	O5—C20—H20B	110.9
H10B—C10—H10C	109.5	C13—C20—H20B	110.9
C12—C11—C9	113.72 (13)	H20A—C20—H20B	108.9
C12—C11—H11A	108.8
C4—C1—O1—C2	0.5 (2)	C12—C13—C14—C7	62.01 (17)
C1—O1—C2—C3	−0.8 (2)	C8—C7—C14—C15	−67.88 (18)
O1—C2—C3—C4	0.8 (2)	C6—C7—C14—C15	49.74 (18)
O1—C1—C4—C3	−0.1 (2)	C9—C7—C14—C15	169.42 (13)
O1—C1—C4—C5	179.74 (15)	C8—C7—C14—C13	64.53 (18)
C2—C3—C4—C1	−0.4 (2)	C6—C7—C14—C13	−177.85 (13)
C2—C3—C4—C5	179.75 (17)	C9—C7—C14—C13	−58.16 (16)
C1—C4—C5—C6	131.66 (19)	C13—C14—C15—C16	63.59 (17)
C3—C4—C5—C6	−48.6 (2)	C7—C14—C15—C16	−162.32 (14)
C4—C5—C6—C7	179.56 (14)	C14—C15—C16—C17	−53.83 (19)
C5—C6—C7—C8	175.77 (15)	C15—C16—C17—C18	23.3 (2)
C5—C6—C7—C14	54.02 (18)	C16—C17—C18—C19	−152.89 (18)
C5—C6—C7—C9	−63.35 (18)	C16—C17—C18—C13	−0.2 (3)
C8—C7—C9—C10	53.24 (19)	C20—C13—C18—C17	−118.6 (2)
C6—C7—C9—C10	−63.98 (17)	C14—C13—C18—C17	8.4 (3)
C14—C7—C9—C10	176.42 (14)	C12—C13—C18—C17	128.46 (19)
C8—C7—C9—C11	−71.78 (18)	C20—C13—C18—C19	37.37 (17)
C6—C7—C9—C11	171.00 (13)	C14—C13—C18—C19	164.41 (14)
C14—C7—C9—C11	51.41 (16)	C12—C13—C18—C19	−75.55 (18)
C10—C9—C11—C12	178.88 (14)	C17—C18—C19—O4	−44.6 (3)
C7—C9—C11—C12	−53.32 (19)	C13—C18—C19—O4	158.06 (19)
C9—C11—C12—C13	55.58 (19)	C17—C18—C19—O5	132.85 (18)
C11—C12—C13—C18	−179.20 (14)	C13—C18—C19—O5	−24.47 (19)
C11—C12—C13—C20	75.54 (17)	O4—C19—O5—C20	176.28 (17)
C11—C12—C13—C14	−57.24 (17)	C18—C19—O5—C20	−1.49 (19)
C18—C13—C14—C15	−39.51 (18)	C19—O5—C20—C13	25.98 (18)
C20—C13—C14—C15	72.02 (19)	C18—C13—C20—O5	−37.35 (15)
C12—C13—C14—C15	−162.72 (13)	C14—C13—C20—O5	−156.21 (14)
C18—C13—C14—C7	−174.78 (13)	C12—C13—C20—O5	79.04 (16)
C20—C13—C14—C7	−63.25 (19)