PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o479.
Published online 2008 January 23. doi:  10.1107/S1600536808001402
PMCID: PMC2960231

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

Abstract

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 [triangle]). For biological activities of sesquiterpenes, see: Endo et al. (1979 [triangle]); Iguchi et al. (1986 [triangle]); Kubo et al. (1992 [triangle]); Delgado et al. (1991 [triangle])

An external file that holds a picture, illustration, etc.
Object name is e-64-0o479-scheme1.jpg

Experimental

Crystal data

  • C15H20O3
  • M r = 248.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o479-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.111
  • S = 1.02
  • 3254 reflections
  • 343 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.16 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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].

Experimental

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.

Refinement

All H atoms were found on difference maps. Atoms H2A, H5A, H9A and H9A were isotropically refined. The remaining H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 (1.5 for methyl) times Ueq(C). In the absence of any significant anomalous scatterers in the compound, the 1052 Friedel pairs were merged before the final refinement.

Figures

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.

Crystal data

C15H20O3F(000) = 536
Mr = 248.31Dx = 1.226 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6207 reflections
a = 9.5295 (19) Åθ = 6.0–55.0°
b = 9.4821 (19) ŵ = 0.08 mm1
c = 15.047 (3) ÅT = 293 K
β = 98.36 (3)°Needle, colorless
V = 1345.2 (5) Å30.29 × 0.08 × 0.08 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer3254 independent reflections
Radiation source: Rotating Anode2012 reflections with I > 2σ(I)
graphiteRint = 0.067
ω oscillation scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −12→12
Tmin = 0.976, Tmax = 0.993k = −11→12
13040 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0543P)2] where P = (Fo2 + 2Fc2)/3
3254 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = −0.16 e Å3

Special details

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)

xyzUiso*/Ueq
O10.1814 (3)0.3739 (4)0.2549 (2)0.1099 (14)
O20.1916 (3)0.4857 (3)0.12807 (18)0.0632 (7)
O3−0.6320 (3)0.5450 (4)−0.18584 (17)0.0883 (11)
O41.1007 (3)0.4719 (3)0.65333 (19)0.0753 (8)
O51.2819 (3)0.6146 (4)0.6438 (2)0.0726 (8)
O60.4647 (2)0.5556 (3)0.18400 (17)0.0685 (8)
C10.1251 (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−0.06510.51400.04650.047*
C4−0.2392 (3)0.3848 (4)0.0280 (2)0.0484 (9)
H4A−0.25380.28410.02000.058*
H4B−0.28040.41220.08070.058*
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−0.20520.6255−0.08660.057*
C7−0.1458 (3)0.4665 (4)−0.1671 (2)0.0507 (9)
H7A−0.12670.5285−0.21610.061*
C8−0.2072 (5)0.3311 (5)−0.2112 (3)0.0745 (12)
H8A−0.13750.2862−0.24170.112*
H8B−0.28960.3529−0.25360.112*
H8C−0.23310.2687−0.16600.112*
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)
H10A0.09460.3278−0.00080.058*
H10B−0.04780.2588−0.04520.058*
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−0.54400.40970.04400.118*
H12B−0.54460.2783−0.01930.118*
H12C−0.65640.3989−0.04280.118*
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−0.38890.7009−0.17970.075*
H14B−0.37750.5710−0.24370.075*
C151.1608 (3)0.5541 (4)0.6110 (2)0.0511 (9)
C161.1042 (3)0.5984 (4)0.5178 (2)0.0458 (8)
C170.9465 (3)0.5744 (4)0.4913 (2)0.0415 (8)
H17A0.92570.47700.50690.050*
C180.8648 (3)0.6722 (4)0.5459 (2)0.0510 (9)
H18A0.92210.68840.60380.061*
H18B0.85260.76230.51530.061*
C190.7194 (3)0.6196 (5)0.5620 (2)0.0545 (9)
H19A0.73140.52730.58990.065*
H19B0.68460.68240.60480.065*
C200.6060 (3)0.6081 (4)0.4799 (2)0.0484 (8)
H20A0.52170.56980.50160.058*
C210.5632 (4)0.7506 (5)0.4404 (3)0.0631 (11)
H21A0.53900.81160.48680.095*
H21B0.48270.74030.39450.095*
H21C0.64080.79070.41480.095*
C220.6444 (3)0.5018 (4)0.4090 (2)0.0458 (8)
H22A0.68180.41490.43870.055*
C230.7508 (3)0.5621 (3)0.3543 (2)0.0390 (7)
C240.9026 (3)0.5920 (4)0.3903 (2)0.0450 (8)
H24A0.92340.68810.37460.054*
H24B0.96150.53040.35990.054*
C250.5173 (3)0.4672 (5)0.3372 (2)0.0571 (9)
H25A0.50930.36620.32740.069*
H25B0.42980.50160.35510.069*
C260.5476 (3)0.5405 (4)0.2543 (2)0.0501 (9)
C270.6940 (3)0.5903 (4)0.2692 (2)0.0422 (8)
C280.7624 (4)0.6651 (4)0.1996 (3)0.0598 (10)
H28A0.85670.62930.19980.090*
H28B0.76680.76430.21260.090*
H28C0.70780.65000.14160.090*
C29−0.0845 (4)0.2777 (5)0.1914 (3)0.0642 (11)
H29A−0.04070.25230.24840.077*
H29B−0.17520.24480.17020.077*
C301.1901 (4)0.6522 (5)0.4661 (3)0.0745 (14)
H30B1.28610.66250.48770.089*
H30C1.15510.68010.40780.089*
H2A0.281 (6)0.505 (6)0.156 (4)0.13 (2)*
H5A1.310 (5)0.600 (5)0.703 (3)0.095 (16)*
H9A0.038 (4)0.530 (4)−0.085 (2)0.053 (10)*
H9B0.064 (3)0.408 (3)−0.146 (2)0.045 (9)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.071 (2)0.175 (4)0.069 (2)−0.038 (2)−0.0345 (17)0.046 (2)
O20.0440 (14)0.0778 (19)0.0615 (17)−0.0130 (14)−0.0139 (13)0.0067 (15)
O30.0444 (15)0.156 (3)0.0570 (17)0.0192 (17)−0.0173 (12)0.006 (2)
O40.0705 (17)0.088 (2)0.0608 (18)−0.0119 (17)−0.0140 (14)0.0196 (17)
O50.0468 (15)0.107 (2)0.0570 (19)−0.0091 (15)−0.0175 (13)0.0051 (17)
O60.0454 (14)0.098 (2)0.0551 (17)−0.0105 (14)−0.0164 (12)−0.0039 (16)
C10.044 (2)0.066 (2)0.048 (2)0.0027 (18)−0.0050 (18)0.002 (2)
C20.0367 (17)0.045 (2)0.0414 (19)0.0039 (15)−0.0034 (14)0.0019 (16)
C30.0309 (16)0.0446 (18)0.0411 (19)0.0009 (13)−0.0010 (13)−0.0020 (15)
C40.0371 (17)0.062 (2)0.043 (2)−0.0046 (16)−0.0052 (14)0.0043 (17)
C50.0365 (17)0.055 (2)0.0383 (19)−0.0006 (16)−0.0010 (14)−0.0051 (17)
C60.0417 (17)0.051 (2)0.047 (2)0.0049 (15)−0.0006 (15)0.0064 (17)
C70.0506 (19)0.062 (2)0.0388 (19)−0.0016 (18)0.0026 (15)0.0049 (18)
C80.089 (3)0.085 (3)0.046 (2)0.004 (3)−0.003 (2)−0.014 (2)
C90.045 (2)0.069 (3)0.050 (2)0.010 (2)0.0107 (18)0.004 (2)
C100.0398 (17)0.053 (2)0.050 (2)0.0096 (16)−0.0016 (16)0.0045 (18)
C110.0329 (17)0.082 (3)0.0371 (19)−0.0007 (17)−0.0021 (14)−0.0076 (19)
C120.040 (2)0.141 (5)0.053 (2)−0.019 (2)−0.0010 (18)0.000 (3)
C130.0418 (19)0.084 (3)0.044 (2)0.0127 (19)−0.0054 (16)−0.004 (2)
C140.050 (2)0.076 (3)0.057 (2)0.012 (2)−0.0069 (17)0.016 (2)
C150.0392 (19)0.057 (2)0.052 (2)0.0039 (17)−0.0078 (16)0.003 (2)
C160.0329 (15)0.058 (2)0.043 (2)0.0003 (16)−0.0042 (14)−0.0023 (17)
C170.0320 (15)0.055 (2)0.0353 (17)0.0000 (15)−0.0033 (13)−0.0019 (16)
C180.0346 (17)0.067 (2)0.048 (2)0.0031 (17)−0.0060 (15)−0.0116 (18)
C190.0463 (19)0.075 (3)0.043 (2)0.0037 (18)0.0092 (16)−0.0038 (18)
C200.0329 (16)0.064 (2)0.048 (2)−0.0001 (17)0.0059 (14)−0.0020 (18)
C210.045 (2)0.073 (3)0.072 (3)0.0121 (19)0.0091 (19)−0.001 (2)
C220.0365 (16)0.059 (2)0.0399 (19)−0.0068 (15)−0.0020 (14)0.0013 (16)
C230.0337 (15)0.0435 (18)0.0392 (19)−0.0033 (14)0.0029 (13)−0.0046 (15)
C240.0333 (15)0.060 (2)0.0395 (19)−0.0020 (16)−0.0018 (14)−0.0030 (17)
C250.0447 (19)0.070 (2)0.055 (2)−0.0174 (19)0.0021 (16)−0.003 (2)
C260.0396 (18)0.056 (2)0.051 (2)−0.0045 (16)−0.0047 (16)−0.0079 (18)
C270.0354 (15)0.0500 (19)0.0389 (19)−0.0004 (15)−0.0024 (14)−0.0075 (16)
C280.052 (2)0.078 (3)0.049 (2)−0.0049 (19)0.0043 (17)0.002 (2)
C290.054 (2)0.080 (3)0.052 (2)0.000 (2)−0.0118 (18)0.012 (2)
C300.0357 (19)0.128 (4)0.058 (3)−0.018 (2)0.0005 (18)0.010 (3)

Geometric parameters (Å, °)

O1—C11.197 (4)C14—H14A0.9700
O2—C11.328 (4)C14—H14B0.9700
O2—H2A0.91 (6)C15—C161.487 (5)
O3—C131.225 (4)C16—C301.312 (5)
O4—C151.203 (4)C16—C171.515 (4)
O5—C151.318 (4)C17—C241.525 (4)
O5—H5A0.90 (5)C17—C181.526 (4)
O6—C261.233 (4)C17—H17A0.9800
C1—C21.480 (5)C18—C191.524 (5)
C2—C291.314 (5)C18—H18A0.9700
C2—C31.520 (4)C18—H18B0.9700
C3—C41.530 (4)C19—C201.523 (5)
C3—C101.537 (4)C19—H19A0.9700
C3—H3A0.9800C19—H19B0.9700
C4—C51.487 (4)C20—C211.508 (5)
C4—H4A0.9700C20—C221.550 (5)
C4—H4B0.9700C20—H20A0.9800
C5—C111.341 (4)C21—H21A0.9600
C5—C61.512 (4)C21—H21B0.9600
C6—C71.534 (5)C21—H21C0.9600
C6—C141.545 (5)C22—C231.509 (4)
C6—H6A0.9800C22—C251.537 (4)
C7—C81.522 (6)C22—H22A0.9800
C7—C91.530 (5)C23—C271.342 (4)
C7—H7A0.9800C23—C241.496 (4)
C8—H8A0.9600C24—H24A0.9700
C8—H8B0.9600C24—H24B0.9700
C8—H8C0.9600C25—C261.492 (5)
C9—C101.523 (5)C25—H25A0.9700
C9—H9A0.97 (4)C25—H25B0.9700
C9—H9B0.97 (3)C26—C271.459 (4)
C10—H10A0.9700C27—C281.492 (5)
C10—H10B0.9700C28—H28A0.9600
C11—C131.454 (5)C28—H28B0.9600
C11—C121.486 (5)C28—H28C0.9600
C12—H12A0.9600C29—H29A0.9300
C12—H12B0.9600C29—H29B0.9300
C12—H12C0.9600C30—H30B0.9300
C13—C141.489 (5)C30—H30C0.9300
C1—O2—H2A109 (3)O5—C15—C16114.1 (3)
C15—O5—H5A115 (3)C30—C16—C15119.8 (3)
O1—C1—O2120.8 (4)C30—C16—C17125.6 (3)
O1—C1—C2124.8 (4)C15—C16—C17114.6 (3)
O2—C1—C2114.3 (3)C16—C17—C24111.4 (2)
C29—C2—C1115.3 (3)C16—C17—C18109.3 (3)
C29—C2—C3125.2 (3)C24—C17—C18112.5 (3)
C1—C2—C3119.5 (3)C16—C17—H17A107.8
C2—C3—C4111.1 (3)C24—C17—H17A107.8
C2—C3—C10112.3 (3)C18—C17—H17A107.8
C4—C3—C10111.1 (3)C19—C18—C17115.7 (3)
C2—C3—H3A107.4C19—C18—H18A108.4
C4—C3—H3A107.4C17—C18—H18A108.4
C10—C3—H3A107.4C19—C18—H18B108.4
C5—C4—C3117.3 (3)C17—C18—H18B108.4
C5—C4—H4A108.0H18A—C18—H18B107.4
C3—C4—H4A108.0C20—C19—C18116.7 (3)
C5—C4—H4B108.0C20—C19—H19A108.1
C3—C4—H4B108.0C18—C19—H19A108.1
H4A—C4—H4B107.2C20—C19—H19B108.1
C11—C5—C4122.2 (3)C18—C19—H19B108.1
C11—C5—C6113.1 (3)H19A—C19—H19B107.3
C4—C5—C6124.8 (3)C21—C20—C19112.0 (3)
C5—C6—C7115.5 (3)C21—C20—C22112.9 (3)
C5—C6—C14102.9 (3)C19—C20—C22113.2 (3)
C7—C6—C14113.0 (3)C21—C20—H20A106.0
C5—C6—H6A108.4C19—C20—H20A106.0
C7—C6—H6A108.4C22—C20—H20A106.0
C14—C6—H6A108.4C20—C21—H21A109.5
C8—C7—C9112.2 (3)C20—C21—H21B109.5
C8—C7—C6112.0 (3)H21A—C21—H21B109.5
C9—C7—C6113.1 (3)C20—C21—H21C109.5
C8—C7—H7A106.3H21A—C21—H21C109.5
C9—C7—H7A106.3H21B—C21—H21C109.5
C6—C7—H7A106.3C23—C22—C25102.8 (3)
C7—C8—H8A109.5C23—C22—C20112.0 (3)
C7—C8—H8B109.5C25—C22—C20112.5 (3)
H8A—C8—H8B109.5C23—C22—H22A109.8
C7—C8—H8C109.5C25—C22—H22A109.8
H8A—C8—H8C109.5C20—C22—H22A109.8
H8B—C8—H8C109.5C27—C23—C24122.9 (3)
C10—C9—C7117.1 (3)C27—C23—C22112.7 (3)
C10—C9—H9A105 (2)C24—C23—C22124.4 (3)
C7—C9—H9A111 (2)C23—C24—C17116.9 (3)
C10—C9—H9B111 (2)C23—C24—H24A108.1
C7—C9—H9B109 (2)C17—C24—H24A108.1
H9A—C9—H9B103 (3)C23—C24—H24B108.1
C9—C10—C3114.0 (3)C17—C24—H24B108.1
C9—C10—H10A108.7H24A—C24—H24B107.3
C3—C10—H10A108.7C26—C25—C22105.0 (3)
C9—C10—H10B108.7C26—C25—H25A110.7
C3—C10—H10B108.7C22—C25—H25A110.7
H10A—C10—H10B107.6C26—C25—H25B110.7
C5—C11—C13109.3 (3)C22—C25—H25B110.7
C5—C11—C12127.4 (3)H25A—C25—H25B108.8
C13—C11—C12123.2 (3)O6—C26—C27125.0 (3)
C11—C12—H12A109.5O6—C26—C25126.4 (3)
C11—C12—H12B109.5C27—C26—C25108.6 (3)
H12A—C12—H12B109.5C23—C27—C26109.1 (3)
C11—C12—H12C109.5C23—C27—C28127.4 (3)
H12A—C12—H12C109.5C26—C27—C28123.5 (3)
H12B—C12—H12C109.5C27—C28—H28A109.5
O3—C13—C11125.1 (3)C27—C28—H28B109.5
O3—C13—C14125.7 (4)H28A—C28—H28B109.5
C11—C13—C14109.2 (3)C27—C28—H28C109.5
C13—C14—C6105.4 (3)H28A—C28—H28C109.5
C13—C14—H14A110.7H28B—C28—H28C109.5
C6—C14—H14A110.7C2—C29—H29A120.0
C13—C14—H14B110.7C2—C29—H29B120.0
C6—C14—H14B110.7H29A—C29—H29B120.0
H14A—C14—H14B108.8C16—C30—H30B120.0
O4—C15—O5122.7 (3)C16—C30—H30C120.0
O4—C15—C16123.1 (3)H30B—C30—H30C120.0
O1—C1—C2—C29−0.4 (6)O4—C15—C16—C30−159.5 (4)
O2—C1—C2—C29178.2 (3)O5—C15—C16—C3021.6 (5)
O1—C1—C2—C3178.2 (4)O4—C15—C16—C1720.0 (5)
O2—C1—C2—C3−3.1 (4)O5—C15—C16—C17−159.0 (3)
C29—C2—C3—C413.2 (5)C30—C16—C17—C2411.7 (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—C1069.6 (4)C15—C16—C17—C1867.4 (4)
C2—C3—C4—C5166.6 (3)C16—C17—C18—C19−152.4 (3)
C10—C3—C4—C5−67.6 (4)C24—C17—C18—C1983.4 (4)
C3—C4—C5—C11−173.6 (3)C17—C18—C19—C20−66.8 (5)
C3—C4—C5—C66.0 (5)C18—C19—C20—C21−67.0 (4)
C11—C5—C6—C7−121.7 (3)C18—C19—C20—C2262.1 (4)
C4—C5—C6—C758.7 (5)C21—C20—C22—C2351.2 (4)
C11—C5—C6—C142.0 (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—C853.1 (4)C19—C20—C22—C25167.5 (3)
C14—C6—C7—C8−65.1 (4)C25—C22—C23—C2711.9 (4)
C5—C6—C7—C9−74.9 (4)C20—C22—C23—C27−109.1 (3)
C14—C6—C7—C9167.0 (3)C25—C22—C23—C24−169.8 (3)
C8—C7—C9—C10−64.2 (5)C20—C22—C23—C2469.2 (4)
C6—C7—C9—C1063.7 (5)C27—C23—C24—C17171.4 (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—C23176.3 (3)
C4—C3—C10—C984.1 (4)C18—C17—C24—C23−60.6 (4)
C4—C5—C11—C13179.8 (3)C23—C22—C25—C26−13.2 (4)
C6—C5—C11—C130.2 (4)C20—C22—C25—C26107.4 (3)
C4—C5—C11—C120.6 (6)C22—C25—C26—O6−169.9 (4)
C6—C5—C11—C12−179.0 (4)C22—C25—C26—C2711.0 (4)
C5—C11—C13—O3177.8 (4)C24—C23—C27—C26176.4 (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—C14176.9 (4)C22—C23—C27—C28172.4 (3)
O3—C13—C14—C6−176.7 (4)O6—C26—C27—C23177.0 (3)
C11—C13—C14—C63.5 (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—C13122.1 (3)C25—C26—C27—C28178.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2A···O60.91 (6)1.80 (6)2.699 (4)166 (5)
O5—H5A···O3i0.90 (5)1.76 (5)2.658 (4)171 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2378).

References

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography