(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetra-methyl-2-oxoperhydro-naphtho[2,1-b]furan-7-yl acetate.

THE TITLE COMPOUND (COMMON NAME: 3β-acet-oxy-8-epi-sclareolide), C(18)H(28)O(4), is a sclareolide derivative, which was synthesized from 9(11)-en-3β-acet-oxy-8-epi-sclareolide. In the mol-ecular structure, the two six-membered rings display chair conformations and the five-membered ring displays an envelope conformation. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For general background, see: Choudhary et al. (2004 ▶); Quideau et al. (2002 ▶). For related structures, see: Devi et al. (2004 ▶); Bhattacharyya et al. (2006 ▶). For synthesis, see: Yang et al. (2006 ▶).

Experimental

Crystal data

C18H28O4

M = 308.40

Monoclinic,

a = 10.1935 (5) Å

b = 7.3226 (3) Å

c = 11.3056 (4) Å

β = 99.2940 (1)°

V = 832.81 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 153 (2) K

0.60 × 0.54 × 0.47 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

8195 measured reflections

2046 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 0.99

2046 reflections

205 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025737/xu2447sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025737/xu2447Isup2.hkl

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

C18H28O4	F000 = 336
Mr = 308.40	Dx = 1.230 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7613 reflections
a = 10.1935 (5) Å	θ = 3.3–27.5º
b = 7.3226 (3) Å	µ = 0.09 mm−1
c = 11.3056 (4) Å	T = 153 (2) K
β = 99.2940 (1)º	Block, colourless
V = 832.81 (6) Å3	0.60 × 0.54 × 0.47 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1943 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.018
Monochromator: graphite	θmax = 27.5º
T = 153(2) K	θmin = 3.3º
ω scans	h = −13→13
Absorption correction: none	k = −9→9
8195 measured reflections	l = −14→12
2046 independent 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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0526P)2 + 0.1209P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
2046 reflections	Δρmax = 0.20 e Å−3
205 parameters	Δρmin = −0.14 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.065 (6)

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
O1	0.15453 (13)	0.2174 (2)	0.55280 (13)	0.0477 (4)
O2	0.10361 (18)	0.3434 (4)	0.37252 (14)	0.0809 (6)
O3	0.78754 (11)	0.58869 (17)	0.86839 (11)	0.0377 (3)
O4	0.77677 (15)	0.8581 (2)	0.96045 (15)	0.0599 (4)
C1	0.44238 (16)	0.6709 (2)	0.70097 (15)	0.0344 (3)
H1A	0.4104	0.7464	0.6295	0.041*
H1B	0.4025	0.7199	0.7687	0.041*
C2	0.59341 (16)	0.6859 (2)	0.73086 (15)	0.0370 (4)
H2A	0.6341	0.6395	0.6630	0.044*
H2B	0.6194	0.8154	0.7443	0.044*
C3	0.64282 (15)	0.5757 (2)	0.84229 (14)	0.0301 (3)
H3	0.6051	0.6290	0.9110	0.036*
C4	0.60784 (14)	0.3708 (2)	0.83267 (13)	0.0280 (3)
C5	0.45489 (14)	0.3533 (2)	0.78539 (13)	0.0259 (3)
H5	0.4102	0.3959	0.8529	0.031*
C6	0.40994 (16)	0.1550 (2)	0.76243 (16)	0.0360 (4)
H6A	0.4350	0.1121	0.6861	0.043*
H6B	0.4551	0.0762	0.8277	0.043*
C7	0.25934 (17)	0.1404 (3)	0.75616 (17)	0.0427 (4)
H7A	0.2310	0.0175	0.7257	0.051*
H7B	0.2388	0.1502	0.8386	0.051*
C8	0.17711 (15)	0.2812 (3)	0.67859 (15)	0.0386 (4)
C9	0.24142 (15)	0.4709 (3)	0.66974 (15)	0.0345 (3)
H9	0.2175	0.5507	0.7348	0.041*
C10	0.39595 (14)	0.4729 (2)	0.67643 (13)	0.0275 (3)
C11	0.1657 (2)	0.5373 (3)	0.54912 (19)	0.0482 (5)
H11A	0.0824	0.6003	0.5595	0.058*
H11B	0.2210	0.6213	0.5093	0.058*
C12	0.13711 (18)	0.3637 (4)	0.47870 (18)	0.0523 (5)
C13	0.43749 (17)	0.4084 (3)	0.55821 (14)	0.0384 (4)
H13A	0.5347	0.4090	0.5663	0.046*
H13B	0.4000	0.4909	0.4932	0.046*
H13C	0.4043	0.2844	0.5399	0.046*
C14	0.03976 (18)	0.2954 (4)	0.7163 (2)	0.0566 (6)
H14A	−0.0028	0.1750	0.7102	0.068*
H14B	−0.0153	0.3816	0.6635	0.068*
H14C	0.0494	0.3388	0.7993	0.068*
C15	0.84029 (17)	0.7424 (3)	0.92062 (16)	0.0399 (4)
C16	0.98747 (19)	0.7482 (3)	0.9221 (2)	0.0523 (5)
H16A	1.0279	0.8355	0.9830	0.063*
H16B	1.0056	0.7864	0.8432	0.063*
H16C	1.0252	0.6266	0.9411	0.063*
C17	0.69680 (16)	0.2695 (3)	0.75667 (16)	0.0395 (4)
H17A	0.6594	0.1485	0.7353	0.047*
H17B	0.7863	0.2562	0.8028	0.047*
H17C	0.7014	0.3393	0.6835	0.047*
C18	0.63524 (17)	0.2918 (3)	0.96055 (16)	0.0410 (4)
H18A	0.7252	0.3255	0.9987	0.049*
H18B	0.6274	0.1585	0.9569	0.049*
H18C	0.5705	0.3412	1.0074	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0391 (7)	0.0550 (9)	0.0468 (7)	−0.0076 (6)	0.0003 (5)	−0.0144 (6)
O2	0.0773 (11)	0.1122 (17)	0.0453 (8)	−0.0063 (12)	−0.0140 (7)	−0.0085 (11)
O3	0.0267 (6)	0.0346 (6)	0.0499 (7)	−0.0043 (5)	0.0006 (5)	−0.0051 (5)
O4	0.0517 (8)	0.0469 (8)	0.0773 (10)	−0.0032 (7)	−0.0014 (7)	−0.0222 (8)
C1	0.0347 (8)	0.0271 (7)	0.0390 (8)	0.0021 (7)	−0.0014 (6)	0.0043 (6)
C2	0.0352 (8)	0.0283 (8)	0.0455 (9)	−0.0064 (7)	0.0008 (6)	0.0055 (7)
C3	0.0243 (7)	0.0283 (8)	0.0365 (8)	−0.0006 (6)	0.0017 (5)	−0.0027 (6)
C4	0.0223 (6)	0.0265 (7)	0.0347 (7)	0.0003 (6)	0.0027 (5)	−0.0008 (6)
C5	0.0233 (6)	0.0255 (7)	0.0291 (7)	0.0001 (5)	0.0050 (5)	−0.0019 (6)
C6	0.0320 (8)	0.0273 (8)	0.0477 (9)	−0.0029 (7)	0.0039 (7)	0.0012 (7)
C7	0.0347 (9)	0.0406 (10)	0.0529 (10)	−0.0109 (8)	0.0072 (7)	0.0021 (8)
C8	0.0267 (7)	0.0466 (10)	0.0418 (9)	−0.0057 (7)	0.0039 (6)	−0.0079 (8)
C9	0.0268 (7)	0.0371 (9)	0.0382 (8)	0.0044 (7)	0.0006 (6)	−0.0045 (7)
C10	0.0267 (6)	0.0274 (7)	0.0278 (7)	0.0006 (6)	0.0026 (5)	−0.0010 (6)
C11	0.0353 (9)	0.0544 (12)	0.0501 (11)	0.0060 (8)	−0.0077 (8)	0.0034 (9)
C12	0.0358 (9)	0.0719 (14)	0.0454 (10)	−0.0014 (10)	−0.0050 (7)	−0.0045 (11)
C13	0.0367 (8)	0.0486 (10)	0.0301 (7)	−0.0023 (7)	0.0060 (6)	−0.0045 (7)
C14	0.0300 (8)	0.0750 (15)	0.0665 (12)	−0.0064 (10)	0.0132 (8)	−0.0086 (12)
C15	0.0383 (8)	0.0364 (9)	0.0415 (8)	−0.0063 (7)	−0.0041 (7)	0.0003 (8)
C16	0.0373 (9)	0.0492 (11)	0.0660 (12)	−0.0129 (9)	−0.0051 (8)	−0.0014 (10)
C17	0.0290 (7)	0.0357 (9)	0.0551 (10)	0.0030 (7)	0.0107 (7)	−0.0073 (8)
C18	0.0372 (8)	0.0409 (9)	0.0419 (9)	0.0002 (7)	−0.0021 (6)	0.0117 (7)

O1—C12	1.354 (3)	C7—H7B	0.9900
O1—C8	1.479 (2)	C8—C14	1.532 (2)
O2—C12	1.203 (2)	C8—C9	1.546 (3)
O3—C15	1.343 (2)	C9—C11	1.534 (2)
O3—C3	1.4601 (18)	C9—C10	1.565 (2)
O4—C15	1.197 (3)	C9—H9	1.0000
C1—C2	1.526 (2)	C10—C13	1.540 (2)
C1—C10	1.536 (2)	C11—C12	1.504 (3)
C1—H1A	0.9900	C11—H11A	0.9900
C1—H1B	0.9900	C11—H11B	0.9900
C2—C3	1.512 (2)	C13—H13A	0.9800
C2—H2A	0.9900	C13—H13B	0.9800
C2—H2B	0.9900	C13—H13C	0.9800
C3—C4	1.542 (2)	C14—H14A	0.9800
C3—H3	1.0000	C14—H14B	0.9800
C4—C17	1.537 (2)	C14—H14C	0.9800
C4—C18	1.540 (2)	C15—C16	1.498 (2)
C4—C5	1.5696 (18)	C16—H16A	0.9800
C5—C6	1.532 (2)	C16—H16B	0.9800
C5—C10	1.551 (2)	C16—H16C	0.9800
C5—H5	1.0000	C17—H17A	0.9800
C6—C7	1.529 (2)	C17—H17B	0.9800
C6—H6A	0.9900	C17—H17C	0.9800
C6—H6B	0.9900	C18—H18A	0.9800
C7—C8	1.516 (3)	C18—H18B	0.9800
C7—H7A	0.9900	C18—H18C	0.9800
C12—O1—C8	109.23 (16)	C8—C9—C10	116.08 (13)
C15—O3—C3	117.60 (13)	C11—C9—H9	108.8
C2—C1—C10	112.21 (13)	C8—C9—H9	108.8
C2—C1—H1A	109.2	C10—C9—H9	108.8
C10—C1—H1A	109.2	C1—C10—C13	109.04 (14)
C2—C1—H1B	109.2	C1—C10—C5	108.73 (11)
C10—C1—H1B	109.2	C13—C10—C5	112.98 (13)
H1A—C1—H1B	107.9	C1—C10—C9	107.23 (13)
C3—C2—C1	109.55 (13)	C13—C10—C9	111.77 (12)
C3—C2—H2A	109.8	C5—C10—C9	106.90 (12)
C1—C2—H2A	109.8	C12—C11—C9	103.26 (17)
C3—C2—H2B	109.8	C12—C11—H11A	111.1
C1—C2—H2B	109.8	C9—C11—H11A	111.1
H2A—C2—H2B	108.2	C12—C11—H11B	111.1
O3—C3—C2	108.86 (13)	C9—C11—H11B	111.1
O3—C3—C4	106.99 (12)	H11A—C11—H11B	109.1
C2—C3—C4	114.73 (13)	O2—C12—O1	120.5 (2)
O3—C3—H3	108.7	O2—C12—C11	129.2 (3)
C2—C3—H3	108.7	O1—C12—C11	110.28 (15)
C4—C3—H3	108.7	C10—C13—H13A	109.5
C17—C4—C18	108.03 (14)	C10—C13—H13B	109.5
C17—C4—C3	111.00 (13)	H13A—C13—H13B	109.5
C18—C4—C3	107.13 (13)	C10—C13—H13C	109.5
C17—C4—C5	114.41 (13)	H13A—C13—H13C	109.5
C18—C4—C5	107.97 (12)	H13B—C13—H13C	109.5
C3—C4—C5	108.02 (12)	C8—C14—H14A	109.5
C6—C5—C10	109.50 (12)	C8—C14—H14B	109.5
C6—C5—C4	112.88 (12)	H14A—C14—H14B	109.5
C10—C5—C4	117.40 (12)	C8—C14—H14C	109.5
C6—C5—H5	105.3	H14A—C14—H14C	109.5
C10—C5—H5	105.3	H14B—C14—H14C	109.5
C4—C5—H5	105.3	O4—C15—O3	123.78 (16)
C7—C6—C5	110.17 (14)	O4—C15—C16	125.24 (18)
C7—C6—H6A	109.6	O3—C15—C16	110.98 (17)
C5—C6—H6A	109.6	C15—C16—H16A	109.5
C7—C6—H6B	109.6	C15—C16—H16B	109.5
C5—C6—H6B	109.6	H16A—C16—H16B	109.5
H6A—C6—H6B	108.1	C15—C16—H16C	109.5
C8—C7—C6	115.88 (15)	H16A—C16—H16C	109.5
C8—C7—H7A	108.3	H16B—C16—H16C	109.5
C6—C7—H7A	108.3	C4—C17—H17A	109.5
C8—C7—H7B	108.3	C4—C17—H17B	109.5
C6—C7—H7B	108.3	H17A—C17—H17B	109.5
H7A—C7—H7B	107.4	C4—C17—H17C	109.5
O1—C8—C7	109.08 (16)	H17A—C17—H17C	109.5
O1—C8—C14	106.37 (14)	H17B—C17—H17C	109.5
C7—C8—C14	109.27 (17)	C4—C18—H18A	109.5
O1—C8—C9	102.92 (14)	C4—C18—H18B	109.5
C7—C8—C9	116.62 (13)	H18A—C18—H18B	109.5
C14—C8—C9	111.92 (17)	C4—C18—H18C	109.5
C11—C9—C8	100.65 (14)	H18A—C18—H18C	109.5
C11—C9—C10	113.45 (15)	H18B—C18—H18C	109.5
C10—C1—C2—C3	−60.61 (18)	C14—C8—C9—C11	−77.70 (18)
C15—O3—C3—C2	77.96 (18)	O1—C8—C9—C10	−86.75 (15)
C15—O3—C3—C4	−157.52 (14)	C7—C8—C9—C10	32.6 (2)
C1—C2—C3—O3	178.97 (13)	C14—C8—C9—C10	159.43 (15)
C1—C2—C3—C4	59.15 (18)	C2—C1—C10—C13	−68.69 (16)
O3—C3—C4—C17	−45.26 (17)	C2—C1—C10—C5	54.89 (17)
C2—C3—C4—C17	75.59 (16)	C2—C1—C10—C9	170.13 (13)
O3—C3—C4—C18	72.47 (15)	C6—C5—C10—C1	−179.85 (13)
C2—C3—C4—C18	−166.68 (13)	C4—C5—C10—C1	−49.46 (17)
O3—C3—C4—C5	−171.45 (11)	C6—C5—C10—C13	−58.66 (16)
C2—C3—C4—C5	−50.60 (17)	C4—C5—C10—C13	71.73 (17)
C17—C4—C5—C6	51.22 (18)	C6—C5—C10—C9	64.69 (15)
C18—C4—C5—C6	−69.07 (17)	C4—C5—C10—C9	−164.91 (13)
C3—C4—C5—C6	175.39 (13)	C11—C9—C10—C1	79.44 (17)
C17—C4—C5—C10	−77.59 (18)	C8—C9—C10—C1	−164.68 (14)
C18—C4—C5—C10	162.11 (14)	C11—C9—C10—C13	−40.0 (2)
C3—C4—C5—C10	46.57 (17)	C8—C9—C10—C13	75.88 (18)
C10—C5—C6—C7	−65.31 (17)	C11—C9—C10—C5	−164.10 (15)
C4—C5—C6—C7	161.90 (13)	C8—C9—C10—C5	−48.22 (17)
C5—C6—C7—C8	47.1 (2)	C8—C9—C11—C12	−31.47 (18)
C12—O1—C8—C7	−152.81 (14)	C10—C9—C11—C12	93.22 (18)
C12—O1—C8—C14	89.45 (19)	C8—O1—C12—O2	−172.27 (18)
C12—O1—C8—C9	−28.36 (17)	C8—O1—C12—C11	7.91 (19)
C6—C7—C8—O1	84.82 (18)	C9—C11—C12—O2	−163.8 (2)
C6—C7—C8—C14	−159.28 (17)	C9—C11—C12—O1	16.0 (2)
C6—C7—C8—C9	−31.1 (2)	C3—O3—C15—O4	9.9 (3)
O1—C8—C9—C11	36.12 (16)	C3—O3—C15—C16	−170.25 (14)
C7—C8—C9—C11	155.46 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O2i	0.98	2.55	3.383 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O2i	0.98	2.55	3.383 (3)	143

Symmetry code: (i) .