(5R,8R)-2-(3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octa­hydro­azulen-5-yl)acrylic acid (rupestonic acid)

Aisa, H.A.; Yong, J.-P.; Lv, Q.-Y.; Wu, T.

doi:10.1107/S1600536808001402

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o479

doi:10.1107/S1600536808001402

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(5R,8R)-2-(3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylic acid (rupestonic acid)

Haji Akber Aisa,^a ^* Jian-Ping Yong,^a,^b Qiao-Ying Lv ^a,^b and Tao Wu ^a,^b

^aXinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Science, Urumqi 830011, People's Republic of China, and ^bGraduate School of Chinese Academy of Science, Beijing 100039, People's Republic of China
^*Correspondence e-mail: haji@ms.xjb.ac.cn

(Received 14 December 2007; accepted 14 January 2008; online 23 January 2008)

The title compound, C₁₅H₂₀O₃, crystallizes with two independent molecules in the asymmetric unit. In both molecules, the seven-membered ring adopts a chair conformation. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains extending in the [201] direction. The absolute configuration was assigned on the basis of the starting materials.

Related literature

For related crystal structures, see: Oberti et al. (1983 ). For biological activities of sesquiterpenes, see: Endo et al. (1979 ); Iguchi et al. (1986 ); Kubo et al. (1992 ); Delgado et al. (1991 )

Experimental

Crystal data

C₁₅H₂₀O₃
M_r = 248.31
Monoclinic, P 2₁
a = 9.5295 (19) Å
b = 9.4821 (19) Å
c = 15.047 (3) Å
β = 98.36 (3)°
V = 1345.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.29 × 0.08 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.976, T_max = 0.993
13040 measured reflections
3254 independent reflections
2012 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.111
S = 1.02
3254 reflections
343 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O6	0.91 (6)	1.80 (6)	2.699 (4)	166 (5)
O5—H5A⋯O3ⁱ	0.90 (5)	1.76 (5)	2.658 (4)	171 (5)
Symmetry code: (i) x+2, y, z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001402/cv2378sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001402/cv2378Isup2.hkl

checkCIF report

Comment top

Rupestonic acid (the title compound) is a sesquiterpene with multifunctional groups, isolated from the Artemisia Rupestris L. (Chinese name is Yizhihao). Sesquiterpenes always exhibit considerable biological activities such as antiinflammatory (Endo et al., 1979), ichtyotoxic and cytotoxic (Iguchi et al., 1986), molluscicidal activities (Kubo et al., 1992; Delgado et al., 1991). Our researching groups have tested the title compound against the herpes simplex type 1, herpes simplex type 2 (HSV-1, HSV-2) and the influenza A3,B virus. The results showed that it exhibits higher activity against influenza B virus (TC50=258.69ug/ml, IC50=28.74ug/ml). We report here the crystal structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Oberti et al., 1983). The title compound crystallizes with two independent molecules in the asymmetric unit. In both molecules, the seven-membered ring adopts a chair conformation. In the crystal, the intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains extended in direction [201].

Related literature top

For related crystal structures, see: Oberti et al. (1983). For biological activities of sesquiterpenes, see: Endo et al. (1979); Iguchi et al. (1986); Kubo et al. (1992); Delgado et al. (1991)

Experimental top

The dry Artemisia Rupestris L. (Chinese name is Yizhihao) was extracted with ethanol, the extraction was evaporated under reduced pressure. The rusidue was purified by the silicon gel column chromatography (EtOAc/ petroleum ether: 5:1–2:1) to obtain the title compound (I). Crystals suitable for X-ray diffraction analysis were obtained by re-crystallization of (I) in acetone/petral ether (1:1 V/V) repetitiously at room temperature.

Computing details top

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

Figures top

Fig. 1. The content of asymmetric unit of (I) showing the atomic numbering and displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.

(5R,8R)-2-(3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8a- octahydroazulen-5-yl)acrylic acid top

Crystal data top

C₁₅H₂₀O₃	F(000) = 536
M_r = 248.31	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6207 reflections
a = 9.5295 (19) Å	θ = 6.0–55.0°
b = 9.4821 (19) Å	µ = 0.08 mm⁻¹
c = 15.047 (3) Å	T = 293 K
β = 98.36 (3)°	Needle, colorless
V = 1345.2 (5) Å³	0.29 × 0.08 × 0.08 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3254 independent reflections
Radiation source: Rotating Anode	2012 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ω oscillation scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
T_min = 0.976, T_max = 0.993	k = −11→12
13040 measured reflections	l = −19→19

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0543P)²] where P = (F_o² + 2F_c²)/3
3254 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₅H₂₀O₃	V = 1345.2 (5) Å³
M_r = 248.31	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.5295 (19) Å	µ = 0.08 mm⁻¹
b = 9.4821 (19) Å	T = 293 K
c = 15.047 (3) Å	0.29 × 0.08 × 0.08 mm
β = 98.36 (3)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3254 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2012 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.993	R_int = 0.067
13040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.14 e Å⁻³
3254 reflections	Δρ_min = −0.16 e Å⁻³
343 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1814 (3)	0.3739 (4)	0.2549 (2)	0.1099 (14)
O2	0.1916 (3)	0.4857 (3)	0.12807 (18)	0.0632 (7)
O3	−0.6320 (3)	0.5450 (4)	−0.18584 (17)	0.0883 (11)
O4	1.1007 (3)	0.4719 (3)	0.65333 (19)	0.0753 (8)
O5	1.2819 (3)	0.6146 (4)	0.6438 (2)	0.0726 (8)
O6	0.4647 (2)	0.5556 (3)	0.18400 (17)	0.0685 (8)
C1	0.1251 (4)	0.4058 (4)	0.1813 (3)	0.0539 (10)
C2	−0.0184 (3)	0.3600 (4)	0.1407 (2)	0.0418 (8)
C3	−0.0794 (3)	0.4117 (3)	0.0475 (2)	0.0395 (7)
H3A	−0.0651	0.5140	0.0465	0.047*
C4	−0.2392 (3)	0.3848 (4)	0.0280 (2)	0.0484 (9)
H4A	−0.2538	0.2841	0.0200	0.058*
H4B	−0.2804	0.4122	0.0807	0.058*
C5	−0.3195 (3)	0.4575 (4)	−0.0511 (2)	0.0438 (8)
C6	−0.2531 (3)	0.5444 (4)	−0.1181 (2)	0.0475 (8)
H6A	−0.2052	0.6255	−0.0866	0.057*
C7	−0.1458 (3)	0.4665 (4)	−0.1671 (2)	0.0507 (9)
H7A	−0.1267	0.5285	−0.2161	0.061*
C8	−0.2072 (5)	0.3311 (5)	−0.2112 (3)	0.0745 (12)
H8A	−0.1375	0.2862	−0.2417	0.112*
H8B	−0.2896	0.3529	−0.2536	0.112*
H8C	−0.2331	0.2687	−0.1660	0.112*
C9	−0.0031 (4)	0.4419 (5)	−0.1081 (3)	0.0541 (10)
C10	−0.0028 (4)	0.3477 (4)	−0.0261 (2)	0.0482 (9)
H10A	0.0946	0.3278	−0.0008	0.058*
H10B	−0.0478	0.2588	−0.0452	0.058*
C11	−0.4614 (3)	0.4519 (4)	−0.0694 (2)	0.0515 (9)
C12	−0.5604 (4)	0.3782 (6)	−0.0172 (3)	0.0790 (15)
H12A	−0.5440	0.4097	0.0440	0.118*
H12B	−0.5446	0.2783	−0.0193	0.118*
H12C	−0.6564	0.3989	−0.0428	0.118*
C13	−0.5085 (4)	0.5330 (5)	−0.1502 (2)	0.0579 (10)
C14	−0.3832 (4)	0.5989 (5)	−0.1823 (3)	0.0626 (10)
H14A	−0.3889	0.7009	−0.1797	0.075*
H14B	−0.3775	0.5710	−0.2437	0.075*
C15	1.1608 (3)	0.5541 (4)	0.6110 (2)	0.0511 (9)
C16	1.1042 (3)	0.5984 (4)	0.5178 (2)	0.0458 (8)
C17	0.9465 (3)	0.5744 (4)	0.4913 (2)	0.0415 (8)
H17A	0.9257	0.4770	0.5069	0.050*
C18	0.8648 (3)	0.6722 (4)	0.5459 (2)	0.0510 (9)
H18A	0.9221	0.6884	0.6038	0.061*
H18B	0.8526	0.7623	0.5153	0.061*
C19	0.7194 (3)	0.6196 (5)	0.5620 (2)	0.0545 (9)
H19A	0.7314	0.5273	0.5899	0.065*
H19B	0.6846	0.6824	0.6048	0.065*
C20	0.6060 (3)	0.6081 (4)	0.4799 (2)	0.0484 (8)
H20A	0.5217	0.5698	0.5016	0.058*
C21	0.5632 (4)	0.7506 (5)	0.4404 (3)	0.0631 (11)
H21A	0.5390	0.8116	0.4868	0.095*
H21B	0.4827	0.7403	0.3945	0.095*
H21C	0.6408	0.7907	0.4148	0.095*
C22	0.6444 (3)	0.5018 (4)	0.4090 (2)	0.0458 (8)
H22A	0.6818	0.4149	0.4387	0.055*
C23	0.7508 (3)	0.5621 (3)	0.3543 (2)	0.0390 (7)
C24	0.9026 (3)	0.5920 (4)	0.3903 (2)	0.0450 (8)
H24A	0.9234	0.6881	0.3746	0.054*
H24B	0.9615	0.5304	0.3599	0.054*
C25	0.5173 (3)	0.4672 (5)	0.3372 (2)	0.0571 (9)
H25A	0.5093	0.3662	0.3274	0.069*
H25B	0.4298	0.5016	0.3551	0.069*
C26	0.5476 (3)	0.5405 (4)	0.2543 (2)	0.0501 (9)
C27	0.6940 (3)	0.5903 (4)	0.2692 (2)	0.0422 (8)
C28	0.7624 (4)	0.6651 (4)	0.1996 (3)	0.0598 (10)
H28A	0.8567	0.6293	0.1998	0.090*
H28B	0.7668	0.7643	0.2126	0.090*
H28C	0.7078	0.6500	0.1416	0.090*
C29	−0.0845 (4)	0.2777 (5)	0.1914 (3)	0.0642 (11)
H29A	−0.0407	0.2523	0.2484	0.077*
H29B	−0.1752	0.2448	0.1702	0.077*
C30	1.1901 (4)	0.6522 (5)	0.4661 (3)	0.0745 (14)
H30B	1.2861	0.6625	0.4877	0.089*
H30C	1.1551	0.6801	0.4078	0.089*
H2A	0.281 (6)	0.505 (6)	0.156 (4)	0.13 (2)*
H5A	1.310 (5)	0.600 (5)	0.703 (3)	0.095 (16)*
H9A	0.038 (4)	0.530 (4)	−0.085 (2)	0.053 (10)*
H9B	0.064 (3)	0.408 (3)	−0.146 (2)	0.045 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.071 (2)	0.175 (4)	0.069 (2)	−0.038 (2)	−0.0345 (17)	0.046 (2)
O2	0.0440 (14)	0.0778 (19)	0.0615 (17)	−0.0130 (14)	−0.0139 (13)	0.0067 (15)
O3	0.0444 (15)	0.156 (3)	0.0570 (17)	0.0192 (17)	−0.0173 (12)	0.006 (2)
O4	0.0705 (17)	0.088 (2)	0.0608 (18)	−0.0119 (17)	−0.0140 (14)	0.0196 (17)
O5	0.0468 (15)	0.107 (2)	0.0570 (19)	−0.0091 (15)	−0.0175 (13)	0.0051 (17)
O6	0.0454 (14)	0.098 (2)	0.0551 (17)	−0.0105 (14)	−0.0164 (12)	−0.0039 (16)
C1	0.044 (2)	0.066 (2)	0.048 (2)	0.0027 (18)	−0.0050 (18)	0.002 (2)
C2	0.0367 (17)	0.045 (2)	0.0414 (19)	0.0039 (15)	−0.0034 (14)	0.0019 (16)
C3	0.0309 (16)	0.0446 (18)	0.0411 (19)	0.0009 (13)	−0.0010 (13)	−0.0020 (15)
C4	0.0371 (17)	0.062 (2)	0.043 (2)	−0.0046 (16)	−0.0052 (14)	0.0043 (17)
C5	0.0365 (17)	0.055 (2)	0.0383 (19)	−0.0006 (16)	−0.0010 (14)	−0.0051 (17)
C6	0.0417 (17)	0.051 (2)	0.047 (2)	0.0049 (15)	−0.0006 (15)	0.0064 (17)
C7	0.0506 (19)	0.062 (2)	0.0388 (19)	−0.0016 (18)	0.0026 (15)	0.0049 (18)
C8	0.089 (3)	0.085 (3)	0.046 (2)	0.004 (3)	−0.003 (2)	−0.014 (2)
C9	0.045 (2)	0.069 (3)	0.050 (2)	0.010 (2)	0.0107 (18)	0.004 (2)
C10	0.0398 (17)	0.053 (2)	0.050 (2)	0.0096 (16)	−0.0016 (16)	0.0045 (18)
C11	0.0329 (17)	0.082 (3)	0.0371 (19)	−0.0007 (17)	−0.0021 (14)	−0.0076 (19)
C12	0.040 (2)	0.141 (5)	0.053 (2)	−0.019 (2)	−0.0010 (18)	0.000 (3)
C13	0.0418 (19)	0.084 (3)	0.044 (2)	0.0127 (19)	−0.0054 (16)	−0.004 (2)
C14	0.050 (2)	0.076 (3)	0.057 (2)	0.012 (2)	−0.0069 (17)	0.016 (2)
C15	0.0392 (19)	0.057 (2)	0.052 (2)	0.0039 (17)	−0.0078 (16)	0.003 (2)
C16	0.0329 (15)	0.058 (2)	0.043 (2)	0.0003 (16)	−0.0042 (14)	−0.0023 (17)
C17	0.0320 (15)	0.055 (2)	0.0353 (17)	0.0000 (15)	−0.0033 (13)	−0.0019 (16)
C18	0.0346 (17)	0.067 (2)	0.048 (2)	0.0031 (17)	−0.0060 (15)	−0.0116 (18)
C19	0.0463 (19)	0.075 (3)	0.043 (2)	0.0037 (18)	0.0092 (16)	−0.0038 (18)
C20	0.0329 (16)	0.064 (2)	0.048 (2)	−0.0001 (17)	0.0059 (14)	−0.0020 (18)
C21	0.045 (2)	0.073 (3)	0.072 (3)	0.0121 (19)	0.0091 (19)	−0.001 (2)
C22	0.0365 (16)	0.059 (2)	0.0399 (19)	−0.0068 (15)	−0.0020 (14)	0.0013 (16)
C23	0.0337 (15)	0.0435 (18)	0.0392 (19)	−0.0033 (14)	0.0029 (13)	−0.0046 (15)
C24	0.0333 (15)	0.060 (2)	0.0395 (19)	−0.0020 (16)	−0.0018 (14)	−0.0030 (17)
C25	0.0447 (19)	0.070 (2)	0.055 (2)	−0.0174 (19)	0.0021 (16)	−0.003 (2)
C26	0.0396 (18)	0.056 (2)	0.051 (2)	−0.0045 (16)	−0.0047 (16)	−0.0079 (18)
C27	0.0354 (15)	0.0500 (19)	0.0389 (19)	−0.0004 (15)	−0.0024 (14)	−0.0075 (16)
C28	0.052 (2)	0.078 (3)	0.049 (2)	−0.0049 (19)	0.0043 (17)	0.002 (2)
C29	0.054 (2)	0.080 (3)	0.052 (2)	0.000 (2)	−0.0118 (18)	0.012 (2)
C30	0.0357 (19)	0.128 (4)	0.058 (3)	−0.018 (2)	0.0005 (18)	0.010 (3)

Geometric parameters (Å, º) top

O1—C1	1.197 (4)	C14—H14A	0.9700
O2—C1	1.328 (4)	C14—H14B	0.9700
O2—H2A	0.91 (6)	C15—C16	1.487 (5)
O3—C13	1.225 (4)	C16—C30	1.312 (5)
O4—C15	1.203 (4)	C16—C17	1.515 (4)
O5—C15	1.318 (4)	C17—C24	1.525 (4)
O5—H5A	0.90 (5)	C17—C18	1.526 (4)
O6—C26	1.233 (4)	C17—H17A	0.9800
C1—C2	1.480 (5)	C18—C19	1.524 (5)
C2—C29	1.314 (5)	C18—H18A	0.9700
C2—C3	1.520 (4)	C18—H18B	0.9700
C3—C4	1.530 (4)	C19—C20	1.523 (5)
C3—C10	1.537 (4)	C19—H19A	0.9700
C3—H3A	0.9800	C19—H19B	0.9700
C4—C5	1.487 (4)	C20—C21	1.508 (5)
C4—H4A	0.9700	C20—C22	1.550 (5)
C4—H4B	0.9700	C20—H20A	0.9800
C5—C11	1.341 (4)	C21—H21A	0.9600
C5—C6	1.512 (4)	C21—H21B	0.9600
C6—C7	1.534 (5)	C21—H21C	0.9600
C6—C14	1.545 (5)	C22—C23	1.509 (4)
C6—H6A	0.9800	C22—C25	1.537 (4)
C7—C8	1.522 (6)	C22—H22A	0.9800
C7—C9	1.530 (5)	C23—C27	1.342 (4)
C7—H7A	0.9800	C23—C24	1.496 (4)
C8—H8A	0.9600	C24—H24A	0.9700
C8—H8B	0.9600	C24—H24B	0.9700
C8—H8C	0.9600	C25—C26	1.492 (5)
C9—C10	1.523 (5)	C25—H25A	0.9700
C9—H9A	0.97 (4)	C25—H25B	0.9700
C9—H9B	0.97 (3)	C26—C27	1.459 (4)
C10—H10A	0.9700	C27—C28	1.492 (5)
C10—H10B	0.9700	C28—H28A	0.9600
C11—C13	1.454 (5)	C28—H28B	0.9600
C11—C12	1.486 (5)	C28—H28C	0.9600
C12—H12A	0.9600	C29—H29A	0.9300
C12—H12B	0.9600	C29—H29B	0.9300
C12—H12C	0.9600	C30—H30B	0.9300
C13—C14	1.489 (5)	C30—H30C	0.9300

C1—O2—H2A	109 (3)	O5—C15—C16	114.1 (3)
C15—O5—H5A	115 (3)	C30—C16—C15	119.8 (3)
O1—C1—O2	120.8 (4)	C30—C16—C17	125.6 (3)
O1—C1—C2	124.8 (4)	C15—C16—C17	114.6 (3)
O2—C1—C2	114.3 (3)	C16—C17—C24	111.4 (2)
C29—C2—C1	115.3 (3)	C16—C17—C18	109.3 (3)
C29—C2—C3	125.2 (3)	C24—C17—C18	112.5 (3)
C1—C2—C3	119.5 (3)	C16—C17—H17A	107.8
C2—C3—C4	111.1 (3)	C24—C17—H17A	107.8
C2—C3—C10	112.3 (3)	C18—C17—H17A	107.8
C4—C3—C10	111.1 (3)	C19—C18—C17	115.7 (3)
C2—C3—H3A	107.4	C19—C18—H18A	108.4
C4—C3—H3A	107.4	C17—C18—H18A	108.4
C10—C3—H3A	107.4	C19—C18—H18B	108.4
C5—C4—C3	117.3 (3)	C17—C18—H18B	108.4
C5—C4—H4A	108.0	H18A—C18—H18B	107.4
C3—C4—H4A	108.0	C20—C19—C18	116.7 (3)
C5—C4—H4B	108.0	C20—C19—H19A	108.1
C3—C4—H4B	108.0	C18—C19—H19A	108.1
H4A—C4—H4B	107.2	C20—C19—H19B	108.1
C11—C5—C4	122.2 (3)	C18—C19—H19B	108.1
C11—C5—C6	113.1 (3)	H19A—C19—H19B	107.3
C4—C5—C6	124.8 (3)	C21—C20—C19	112.0 (3)
C5—C6—C7	115.5 (3)	C21—C20—C22	112.9 (3)
C5—C6—C14	102.9 (3)	C19—C20—C22	113.2 (3)
C7—C6—C14	113.0 (3)	C21—C20—H20A	106.0
C5—C6—H6A	108.4	C19—C20—H20A	106.0
C7—C6—H6A	108.4	C22—C20—H20A	106.0
C14—C6—H6A	108.4	C20—C21—H21A	109.5
C8—C7—C9	112.2 (3)	C20—C21—H21B	109.5
C8—C7—C6	112.0 (3)	H21A—C21—H21B	109.5
C9—C7—C6	113.1 (3)	C20—C21—H21C	109.5
C8—C7—H7A	106.3	H21A—C21—H21C	109.5
C9—C7—H7A	106.3	H21B—C21—H21C	109.5
C6—C7—H7A	106.3	C23—C22—C25	102.8 (3)
C7—C8—H8A	109.5	C23—C22—C20	112.0 (3)
C7—C8—H8B	109.5	C25—C22—C20	112.5 (3)
H8A—C8—H8B	109.5	C23—C22—H22A	109.8
C7—C8—H8C	109.5	C25—C22—H22A	109.8
H8A—C8—H8C	109.5	C20—C22—H22A	109.8
H8B—C8—H8C	109.5	C27—C23—C24	122.9 (3)
C10—C9—C7	117.1 (3)	C27—C23—C22	112.7 (3)
C10—C9—H9A	105 (2)	C24—C23—C22	124.4 (3)
C7—C9—H9A	111 (2)	C23—C24—C17	116.9 (3)
C10—C9—H9B	111 (2)	C23—C24—H24A	108.1
C7—C9—H9B	109 (2)	C17—C24—H24A	108.1
H9A—C9—H9B	103 (3)	C23—C24—H24B	108.1
C9—C10—C3	114.0 (3)	C17—C24—H24B	108.1
C9—C10—H10A	108.7	H24A—C24—H24B	107.3
C3—C10—H10A	108.7	C26—C25—C22	105.0 (3)
C9—C10—H10B	108.7	C26—C25—H25A	110.7
C3—C10—H10B	108.7	C22—C25—H25A	110.7
H10A—C10—H10B	107.6	C26—C25—H25B	110.7
C5—C11—C13	109.3 (3)	C22—C25—H25B	110.7
C5—C11—C12	127.4 (3)	H25A—C25—H25B	108.8
C13—C11—C12	123.2 (3)	O6—C26—C27	125.0 (3)
C11—C12—H12A	109.5	O6—C26—C25	126.4 (3)
C11—C12—H12B	109.5	C27—C26—C25	108.6 (3)
H12A—C12—H12B	109.5	C23—C27—C26	109.1 (3)
C11—C12—H12C	109.5	C23—C27—C28	127.4 (3)
H12A—C12—H12C	109.5	C26—C27—C28	123.5 (3)
H12B—C12—H12C	109.5	C27—C28—H28A	109.5
O3—C13—C11	125.1 (3)	C27—C28—H28B	109.5
O3—C13—C14	125.7 (4)	H28A—C28—H28B	109.5
C11—C13—C14	109.2 (3)	C27—C28—H28C	109.5
C13—C14—C6	105.4 (3)	H28A—C28—H28C	109.5
C13—C14—H14A	110.7	H28B—C28—H28C	109.5
C6—C14—H14A	110.7	C2—C29—H29A	120.0
C13—C14—H14B	110.7	C2—C29—H29B	120.0
C6—C14—H14B	110.7	H29A—C29—H29B	120.0
H14A—C14—H14B	108.8	C16—C30—H30B	120.0
O4—C15—O5	122.7 (3)	C16—C30—H30C	120.0
O4—C15—C16	123.1 (3)	H30B—C30—H30C	120.0

O1—C1—C2—C29	−0.4 (6)	O4—C15—C16—C30	−159.5 (4)
O2—C1—C2—C29	178.2 (3)	O5—C15—C16—C30	21.6 (5)
O1—C1—C2—C3	178.2 (4)	O4—C15—C16—C17	20.0 (5)
O2—C1—C2—C3	−3.1 (4)	O5—C15—C16—C17	−159.0 (3)
C29—C2—C3—C4	13.2 (5)	C30—C16—C17—C24	11.7 (5)
C1—C2—C3—C4	−165.3 (3)	C15—C16—C17—C24	−167.7 (3)
C29—C2—C3—C10	−111.9 (4)	C30—C16—C17—C18	−113.2 (4)
C1—C2—C3—C10	69.6 (4)	C15—C16—C17—C18	67.4 (4)
C2—C3—C4—C5	166.6 (3)	C16—C17—C18—C19	−152.4 (3)
C10—C3—C4—C5	−67.6 (4)	C24—C17—C18—C19	83.4 (4)
C3—C4—C5—C11	−173.6 (3)	C17—C18—C19—C20	−66.8 (5)
C3—C4—C5—C6	6.0 (5)	C18—C19—C20—C21	−67.0 (4)
C11—C5—C6—C7	−121.7 (3)	C18—C19—C20—C22	62.1 (4)
C4—C5—C6—C7	58.7 (5)	C21—C20—C22—C23	51.2 (4)
C11—C5—C6—C14	2.0 (4)	C19—C20—C22—C23	−77.3 (4)
C4—C5—C6—C14	−177.7 (3)	C21—C20—C22—C25	−63.9 (4)
C5—C6—C7—C8	53.1 (4)	C19—C20—C22—C25	167.5 (3)
C14—C6—C7—C8	−65.1 (4)	C25—C22—C23—C27	11.9 (4)
C5—C6—C7—C9	−74.9 (4)	C20—C22—C23—C27	−109.1 (3)
C14—C6—C7—C9	167.0 (3)	C25—C22—C23—C24	−169.8 (3)
C8—C7—C9—C10	−64.2 (5)	C20—C22—C23—C24	69.2 (4)
C6—C7—C9—C10	63.7 (5)	C27—C23—C24—C17	171.4 (3)
C7—C9—C10—C3	−68.2 (5)	C22—C23—C24—C17	−6.7 (5)
C2—C3—C10—C9	−150.9 (3)	C16—C17—C24—C23	176.3 (3)
C4—C3—C10—C9	84.1 (4)	C18—C17—C24—C23	−60.6 (4)
C4—C5—C11—C13	179.8 (3)	C23—C22—C25—C26	−13.2 (4)
C6—C5—C11—C13	0.2 (4)	C20—C22—C25—C26	107.4 (3)
C4—C5—C11—C12	0.6 (6)	C22—C25—C26—O6	−169.9 (4)
C6—C5—C11—C12	−179.0 (4)	C22—C25—C26—C27	11.0 (4)
C5—C11—C13—O3	177.8 (4)	C24—C23—C27—C26	176.4 (3)
C12—C11—C13—O3	−3.0 (6)	C22—C23—C27—C26	−5.3 (4)
C5—C11—C13—C14	−2.4 (4)	C24—C23—C27—C28	−5.9 (5)
C12—C11—C13—C14	176.9 (4)	C22—C23—C27—C28	172.4 (3)
O3—C13—C14—C6	−176.7 (4)	O6—C26—C27—C23	177.0 (3)
C11—C13—C14—C6	3.5 (4)	C25—C26—C27—C23	−3.9 (4)
C5—C6—C14—C13	−3.2 (4)	O6—C26—C27—C28	−0.8 (5)
C7—C6—C14—C13	122.1 (3)	C25—C26—C27—C28	178.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O6	0.91 (6)	1.80 (6)	2.699 (4)	166 (5)
O5—H5A···O3ⁱ	0.90 (5)	1.76 (5)	2.658 (4)	171 (5)

Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀O₃
M_r	248.31
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.5295 (19), 9.4821 (19), 15.047 (3)
β (°)	98.36 (3)
V (Å³)	1345.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.08 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.976, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	13040, 3254, 2012
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.111, 1.02
No. of reflections	3254
No. of parameters	343
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O6	0.91 (6)	1.80 (6)	2.699 (4)	166 (5)
O5—H5A···O3ⁱ	0.90 (5)	1.76 (5)	2.658 (4)	171 (5)

Symmetry code: (i) x+2, y, z+1.

Acknowledgements

This work was supported financially by the Foundation of Xinjiang Key Laboratory of Plant Resources and Natural Products Chemistry (grant No. 2006-6).

References

Delgado, G., Garcia, P. E., Bye, R. A. & Linares, E. (1991). Phytochemistry, 30, 1716–1719. CrossRef CAS Web of Science Google Scholar
Endo, K., Taguchi, T., Taguchi, F., Hikino, H., Yamahara, J. & Fujimura, H. (1979). Chem. Pharm. Bull. 27, 2954–5958. CrossRef CAS PubMed Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Iguchi, K., Mori, K., Suzuki, M., Takahashi, H. & Yamada, Y. (1986). Chem. Lett. pp. 1789–1792. CrossRef Web of Science Google Scholar
Kubo, I., Ying, B. P., Castillo, M., Brinen, L. S. & Clardy, J. (1992). Phytochemistry, 31, 1545–1548. CSD CrossRef CAS Web of Science Google Scholar
Oberti, J. C., Sosa, V. E., Herz, W., Prasad, J. S. & Goedken, V. L. (1983). J. Org. Chem. 48, 4038–4043. CSD CrossRef CAS Web of Science Google Scholar
Rigaku (2004). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 2| February 2008| Page o479

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(5R,8R)-2-(3,8-Di­methyl-2-oxo-1,2,4,5,6,7,8,8a-octa­hydro­azulen-5-yl)acrylic acid (rupestonic acid)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(5R,8R)-2-(3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylic acid (rupestonic acid)