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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3301.
Published online 2010 November 27. doi:  10.1107/S1600536810047987
PMCID: PMC3011540

(20S)-20-Acet­oxy-4-pregnene-3,16-dione from Commiphora wightii

Abstract

The title triterpene compound, C23H32O4, isolated from Commiphora wightii features four trans-fused rings, among which the five-membered ring adopts an envelope conformation, the cyclo­hexene ring adopts a half-chair conformation and the two cyclo­hexane rings exist in chair conformations. The asymmetric unit contains two independent mol­ecules. Weak inter­molecular C—H(...)O hydrogen bonding is present in the crystal structure.

Related literature

For the crystal structures of similar steroids and terpene analogues and other related structures, see: Coiro et al. (1982 [triangle]); Geise et al. (1966) [triangle]. For the isolation of the title compound from other plants, see: Francis et al. (2004 [triangle]); Hung et al. (1995 [triangle]); Zhu et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3301-scheme1.jpg

Experimental

Crystal data

  • C23H32O4
  • M r = 372.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3301-efi1.jpg
  • a = 8.2802 (4) Å
  • b = 8.6819 (5) Å
  • c = 14.1363 (7) Å
  • α = 94.130 (1)°
  • β = 97.028 (1)°
  • γ = 90.603 (1)°
  • V = 1005.78 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.4 × 0.3 × 0.2 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 4968 measured reflections
  • 3440 independent reflections
  • 3340 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.111
  • S = 1.05
  • 3440 reflections
  • 495 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047987/xu5092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047987/xu5092Isup2.hkl

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

Acknowledgments

We acknowledge funding by the Pak-USAID Project (Linkages of Centers for Chemical Sciences, grant No. 1–5/ILS-US/HEC/2004) and the United States Food and Drug Administration (FDA) Specific Cooperative Research (Agreement No. 5U01FD002071–08). We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

20(S)-Acetyloxy-4-pregnene-3,16-dione (Scheme I) has been isolated from the gum resin of Ailanthus grandis and Commiphora mukul (Francis et al., 2004; Hung et al., 1995). Commiphora wightii (Arnott.), a medicinal plant native to parts of Pakistan and India (Zhu et al., 2001), also yields this compound. The triterpene, C23H32O4, features four trans fused-rings A–D. Rings B and C exist in a chair conformation whereas ring A adopts a half-chair conformation and ring D an envelope conformation. There are two independent molecules that have similar bond dimensions (Figs. 1 & 2). The stereochemistry is that established in others steroids and terpenes (Coiro et al., 1982; Geise et al., 1966).

Experimental

Gum resin samples of Commiphora wightii were collected from different locations of Pakistan and India, and were deposited at the National Center for Natural Products Research, University of Mississippi. Gum resin (1.5 kg) was extracted with ethyl acetate (5.0 L × 72 h) at room temperature; the extract was evaporated to a brown gummy material (250 g). This was subjected to silica-gel column-chromatography and eluted with hexane/ethyl acetate[19:1 (3 L), 9:1 (5 L), 4:1 (5 L), 7:3 (5 L), 1:1 (3 L), 0:1 (2 L)] and acetone (2 L) to yield 24 fractions. The seventeenth fraction was subjected to vapor-liquid chromatography on silica followed by elution with methanol/water [3:2 (1.5 L), 13:7 (1.5 L), 7:3 (1 L), 4:1 (2 L), 9:1 (3 L) and 1:0 (1 L)] and acetone (1 L)] to give 19 fractions. 20(S)-acetyloxy-4-pregnene-3,16-dione (10 mg) was obtained from the sixth fraction and purified by recrystallization from methanol to furnish colorless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of one molecule of C23H32O4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Thermal ellipsoid plot (Barbour, 2001) of second molecule of C23H32O4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C23H32O4Z = 2
Mr = 372.49F(000) = 404
Triclinic, P1Dx = 1.230 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2802 (4) ÅCell parameters from 3395 reflections
b = 8.6819 (5) Åθ = 2.4–28.3°
c = 14.1363 (7) ŵ = 0.08 mm1
α = 94.130 (1)°T = 293 K
β = 97.028 (1)°Block, colorless
γ = 90.603 (1)°0.4 × 0.3 × 0.2 mm
V = 1005.78 (9) Å3

Data collection

Bruker SMART APEX diffractometer3340 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
graphiteθmax = 25.0°, θmin = 1.5°
ω scansh = −9→9
4968 measured reflectionsk = −10→9
3440 independent reflectionsl = −7→16

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.080P)2 + 0.1003P] where P = (Fo2 + 2Fc2)/3
3440 reflections(Δ/σ)max = 0.001
495 parametersΔρmax = 0.28 e Å3
3 restraintsΔρmin = −0.22 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

xyzUiso*/Ueq
O10.2485 (3)0.2488 (3)0.00029 (16)0.0335 (6)
O2−0.3659 (3)0.3251 (3)0.65217 (16)0.0250 (5)
O30.1541 (2)0.3512 (2)0.75785 (14)0.0192 (4)
O40.1920 (3)0.5699 (3)0.85416 (18)0.0335 (6)
O51.0521 (3)1.0060 (3)1.23280 (15)0.0321 (6)
O60.1200 (3)0.9567 (2)0.59102 (15)0.0237 (5)
O70.5908 (2)0.9323 (2)0.47823 (14)0.0189 (4)
O80.5936 (3)0.7041 (3)0.39246 (18)0.0346 (6)
C10.1898 (4)0.6166 (4)0.2800 (2)0.0268 (7)
H1A0.21110.65090.21960.040*
H1B0.28140.64250.32720.040*
H1C0.09470.66630.29920.040*
C20.1611 (4)0.4405 (3)0.2706 (2)0.0200 (6)
C30.3192 (4)0.3581 (4)0.2519 (2)0.0269 (7)
H3A0.40790.40150.29750.032*
H3B0.30770.24960.26250.032*
C40.3626 (4)0.3723 (4)0.1505 (2)0.0298 (7)
H4A0.38640.47960.14190.036*
H4B0.45950.31360.14200.036*
C50.2258 (4)0.3138 (4)0.0768 (2)0.0256 (7)
C60.0621 (4)0.3419 (4)0.1015 (2)0.0236 (7)
H6−0.02530.31670.05490.028*
C70.0292 (4)0.4017 (3)0.1871 (2)0.0199 (6)
C8−0.1438 (4)0.4368 (4)0.2032 (2)0.0252 (7)
H8A−0.21710.39680.14790.030*
H8B−0.15660.54780.21040.030*
C9−0.1890 (4)0.3649 (4)0.2923 (2)0.0233 (7)
H9A−0.29870.39330.30280.028*
H9B−0.18600.25320.28300.028*
C10−0.0702 (3)0.4211 (3)0.3791 (2)0.0172 (6)
H10−0.07780.53350.38950.021*
C110.1060 (3)0.3806 (3)0.3636 (2)0.0171 (6)
H110.10890.26770.35580.021*
C120.2261 (4)0.4297 (3)0.45342 (19)0.0183 (6)
H12A0.33360.39360.44350.022*
H12B0.23180.54160.46170.022*
C130.1786 (3)0.3666 (3)0.5454 (2)0.0174 (6)
H13A0.18870.25520.54160.021*
H13B0.25270.40920.59970.021*
C140.0042 (3)0.4081 (3)0.56053 (19)0.0150 (6)
C15−0.0106 (4)0.5830 (3)0.5827 (2)0.0200 (6)
H15A0.02210.63680.53100.030*
H15B0.05830.61480.64060.030*
H15C−0.12150.60640.59040.030*
C16−0.1070 (3)0.3466 (3)0.46947 (19)0.0160 (6)
H16−0.08420.23650.45950.019*
C17−0.2799 (4)0.3562 (3)0.4976 (2)0.0197 (6)
H17A−0.32640.45610.48570.024*
H17B−0.35030.27600.46260.024*
C18−0.2555 (4)0.3326 (3)0.6037 (2)0.0180 (6)
C19−0.0724 (3)0.3211 (3)0.6372 (2)0.0166 (6)
H19−0.04410.21210.62850.020*
C20−0.0217 (3)0.3736 (3)0.7419 (2)0.0183 (6)
H20−0.04550.48320.75330.022*
C21−0.0954 (4)0.2809 (4)0.8131 (2)0.0227 (6)
H21A−0.04950.31600.87670.034*
H21B−0.07240.17360.80130.034*
H21C−0.21110.29440.80630.034*
C220.2442 (4)0.4532 (3)0.8198 (2)0.0198 (6)
C230.4153 (4)0.3996 (4)0.8376 (2)0.0249 (7)
H23A0.48120.47860.87550.037*
H23B0.45720.37870.77770.037*
H23C0.41750.30720.87110.037*
C240.8266 (4)0.6592 (4)0.9568 (2)0.0248 (6)
H24A0.87410.62561.01700.037*
H24B0.89240.62620.90800.037*
H24C0.71900.61520.94100.037*
C250.8174 (4)0.8369 (3)0.96365 (19)0.0180 (6)
C260.9907 (4)0.9082 (4)0.9777 (2)0.0239 (7)
H26A1.05280.85870.93060.029*
H26B0.98411.01690.96640.029*
C271.0807 (4)0.8922 (4)1.0769 (2)0.0268 (7)
H27A1.10210.78401.08500.032*
H27B1.18460.94691.08270.032*
C280.9851 (4)0.9551 (4)1.1542 (2)0.0240 (7)
C290.8083 (4)0.9441 (4)1.1330 (2)0.0253 (7)
H290.74650.97981.18040.030*
C300.7293 (4)0.8859 (3)1.0493 (2)0.0217 (7)
C310.5485 (4)0.8600 (4)1.0375 (2)0.0276 (7)
H31A0.50490.90651.09330.033*
H31B0.52460.75001.03350.033*
C320.4645 (4)0.9291 (4)0.9476 (2)0.0256 (7)
H32A0.34900.90380.94000.031*
H32B0.47731.04070.95440.031*
C330.5384 (4)0.8652 (3)0.8596 (2)0.0180 (6)
H330.51870.75330.85120.022*
C340.7233 (3)0.8976 (3)0.87123 (19)0.0161 (6)
H340.73661.01030.87850.019*
C350.7982 (4)0.8454 (3)0.7801 (2)0.0184 (6)
H350.79480.73340.77230.022*
H35B0.91150.87870.78790.022*
C360.7109 (3)0.9090 (3)0.6891 (2)0.0177 (6)
H36A0.72821.02000.69220.021*
H36B0.75730.86420.63390.021*
C370.5281 (3)0.8725 (3)0.67725 (19)0.0150 (6)
C380.4955 (4)0.6982 (3)0.6570 (2)0.0204 (6)
H38A0.53810.66340.59910.031*
H38B0.38030.67750.64990.031*
H38C0.54750.64470.70910.031*
C390.4629 (3)0.9379 (3)0.76972 (19)0.0167 (6)
H390.49461.04760.77810.020*
C400.2778 (4)0.9317 (4)0.7444 (2)0.0205 (6)
H40A0.23290.83350.75850.025*
H40B0.22731.01440.77950.025*
C410.2523 (4)0.9512 (3)0.6378 (2)0.0184 (6)
C420.4199 (3)0.9600 (3)0.6019 (2)0.0162 (6)
H420.45591.06860.61000.019*
C430.4216 (4)0.9065 (3)0.4966 (2)0.0192 (6)
H430.39310.79620.48620.023*
C440.3164 (4)0.9962 (4)0.4253 (2)0.0240 (7)
H44A0.32990.95700.36150.036*
H44B0.34811.10350.43390.036*
H44C0.20430.98500.43520.036*
C450.6574 (4)0.8269 (3)0.4217 (2)0.0204 (6)
C460.8215 (4)0.8812 (4)0.4021 (2)0.0262 (7)
H46A0.86670.80470.36090.039*
H46B0.89220.89730.46120.039*
H46C0.81100.97650.37150.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0412 (15)0.0379 (13)0.0235 (12)0.0034 (11)0.0133 (10)0.0012 (10)
O20.0210 (11)0.0307 (12)0.0252 (11)−0.0001 (9)0.0088 (9)0.0052 (9)
O30.0203 (11)0.0211 (10)0.0161 (10)−0.0008 (9)0.0024 (8)0.0001 (8)
O40.0271 (12)0.0255 (12)0.0452 (14)−0.0027 (10)0.0017 (10)−0.0113 (10)
O50.0362 (14)0.0370 (13)0.0204 (11)−0.0050 (11)−0.0074 (10)0.0026 (10)
O60.0159 (11)0.0266 (11)0.0278 (11)−0.0007 (9)−0.0031 (9)0.0060 (9)
O70.0198 (11)0.0203 (10)0.0167 (10)−0.0015 (8)0.0027 (8)0.0023 (8)
O80.0313 (14)0.0257 (12)0.0463 (15)−0.0016 (10)0.0102 (11)−0.0094 (10)
C10.0327 (18)0.0287 (16)0.0193 (15)−0.0077 (13)0.0014 (13)0.0081 (12)
C20.0175 (15)0.0272 (16)0.0162 (14)−0.0026 (12)0.0041 (11)0.0062 (12)
C30.0210 (16)0.0415 (19)0.0195 (15)0.0023 (14)0.0048 (12)0.0062 (13)
C40.0222 (17)0.046 (2)0.0244 (16)0.0004 (14)0.0113 (14)0.0072 (14)
C50.0350 (19)0.0254 (16)0.0187 (15)0.0040 (14)0.0087 (13)0.0078 (12)
C60.0259 (17)0.0267 (16)0.0184 (14)−0.0007 (13)0.0009 (12)0.0070 (12)
C70.0199 (16)0.0214 (15)0.0191 (14)−0.0005 (12)0.0025 (12)0.0065 (11)
C80.0218 (16)0.0356 (17)0.0182 (15)0.0033 (13)0.0003 (12)0.0057 (13)
C90.0181 (15)0.0329 (17)0.0193 (15)0.0006 (13)0.0032 (12)0.0025 (12)
C100.0176 (15)0.0192 (14)0.0155 (14)0.0001 (11)0.0038 (11)0.0027 (11)
C110.0173 (15)0.0202 (14)0.0143 (13)−0.0006 (11)0.0028 (11)0.0030 (11)
C120.0153 (14)0.0237 (14)0.0165 (14)−0.0036 (12)0.0033 (11)0.0031 (11)
C130.0163 (15)0.0203 (14)0.0153 (13)−0.0046 (12)0.0003 (11)0.0018 (11)
C140.0167 (14)0.0154 (13)0.0133 (13)−0.0024 (11)0.0032 (11)0.0025 (10)
C150.0270 (16)0.0187 (14)0.0147 (13)−0.0030 (12)0.0033 (11)0.0021 (11)
C160.0161 (14)0.0177 (14)0.0143 (13)0.0005 (11)0.0019 (11)0.0031 (11)
C170.0153 (14)0.0221 (14)0.0222 (15)−0.0014 (11)0.0043 (12)0.0012 (12)
C180.0181 (15)0.0128 (13)0.0239 (14)−0.0022 (11)0.0068 (12)−0.0009 (11)
C190.0191 (15)0.0137 (13)0.0183 (14)0.0008 (11)0.0066 (11)0.0032 (10)
C200.0182 (15)0.0182 (14)0.0193 (14)−0.0017 (12)0.0050 (11)0.0030 (11)
C210.0239 (16)0.0269 (16)0.0184 (14)−0.0044 (13)0.0065 (12)0.0042 (12)
C220.0225 (16)0.0197 (15)0.0179 (14)−0.0049 (12)0.0047 (12)0.0025 (12)
C230.0252 (17)0.0266 (16)0.0233 (15)−0.0054 (13)0.0038 (13)0.0048 (12)
C240.0292 (17)0.0247 (15)0.0208 (14)0.0026 (13)0.0005 (12)0.0072 (12)
C250.0185 (14)0.0234 (15)0.0125 (13)0.0005 (12)0.0010 (11)0.0050 (11)
C260.0223 (16)0.0302 (16)0.0197 (15)−0.0018 (13)0.0035 (12)0.0044 (12)
C270.0184 (16)0.0375 (18)0.0242 (16)−0.0020 (14)−0.0020 (12)0.0094 (13)
C280.0307 (17)0.0233 (15)0.0176 (15)−0.0009 (13)−0.0019 (13)0.0064 (12)
C290.0321 (18)0.0293 (16)0.0155 (14)0.0049 (14)0.0040 (13)0.0048 (12)
C300.0254 (17)0.0220 (15)0.0184 (14)0.0035 (13)0.0021 (12)0.0069 (12)
C310.0216 (16)0.046 (2)0.0167 (15)−0.0016 (14)0.0069 (12)0.0046 (13)
C320.0175 (15)0.0396 (19)0.0194 (15)0.0011 (14)0.0025 (12)−0.0003 (13)
C330.0170 (15)0.0198 (14)0.0175 (14)−0.0008 (11)0.0025 (11)0.0028 (11)
C340.0176 (15)0.0153 (13)0.0156 (14)0.0011 (11)0.0016 (11)0.0029 (11)
C350.0137 (14)0.0229 (15)0.0189 (14)−0.0002 (11)0.0022 (11)0.0026 (11)
C360.0153 (14)0.0224 (14)0.0154 (13)0.0012 (11)0.0024 (11)0.0006 (11)
C370.0135 (14)0.0169 (14)0.0143 (13)0.0014 (11)0.0006 (11)−0.0003 (10)
C380.0242 (15)0.0178 (14)0.0191 (14)0.0020 (12)0.0020 (12)0.0011 (11)
C390.0160 (14)0.0183 (14)0.0160 (14)−0.0009 (11)0.0031 (11)0.0007 (11)
C400.0160 (15)0.0233 (15)0.0224 (15)0.0005 (11)0.0041 (11)0.0004 (12)
C410.0170 (15)0.0111 (13)0.0262 (15)−0.0021 (11)0.0010 (12)−0.0015 (11)
C420.0196 (15)0.0125 (13)0.0160 (13)−0.0021 (11)0.0005 (11)−0.0005 (10)
C430.0185 (15)0.0225 (15)0.0160 (14)−0.0010 (12)0.0003 (11)0.0013 (11)
C440.0261 (16)0.0276 (16)0.0181 (15)−0.0001 (13)−0.0001 (12)0.0040 (12)
C450.0257 (16)0.0208 (15)0.0137 (13)0.0033 (12)−0.0024 (12)0.0019 (11)
C460.0274 (17)0.0286 (16)0.0232 (16)0.0031 (13)0.0042 (13)0.0033 (12)

Geometric parameters (Å, °)

O1—C51.220 (4)C21—H21C0.9600
O2—C181.211 (4)C22—C231.494 (4)
O3—C221.349 (4)C23—H23A0.9600
O3—C201.463 (3)C23—H23B0.9600
O4—C221.200 (4)C23—H23C0.9600
O5—C281.229 (4)C24—C251.542 (4)
O6—C411.212 (4)C24—H24A0.9600
O7—C451.339 (4)C24—H24B0.9600
O7—C431.473 (4)C24—H24C0.9600
O8—C451.207 (4)C25—C301.526 (4)
C1—C21.539 (4)C25—C261.541 (4)
C1—H1A0.9600C25—C341.566 (4)
C1—H1B0.9600C26—C271.522 (4)
C1—H1C0.9600C26—H26A0.9700
C2—C71.522 (4)C26—H26B0.9700
C2—C31.540 (4)C27—C281.502 (4)
C2—C111.565 (4)C27—H27A0.9700
C3—C41.532 (4)C27—H27B0.9700
C3—H3A0.9700C28—C291.458 (5)
C3—H3B0.9700C29—C301.341 (4)
C4—C51.500 (5)C29—H290.9300
C4—H4A0.9700C30—C311.499 (4)
C4—H4B0.9700C31—C321.536 (4)
C5—C61.459 (4)C31—H31A0.9700
C6—C71.342 (4)C31—H31B0.9700
C6—H60.9300C32—C331.525 (4)
C7—C81.509 (4)C32—H32A0.9700
C8—C91.529 (4)C32—H32B0.9700
C8—H8A0.9700C33—C391.528 (4)
C8—H8B0.9700C33—C341.540 (4)
C9—C101.523 (4)C33—H330.9800
C9—H9A0.9700C34—C351.538 (4)
C9—H9B0.9700C34—H340.9800
C10—C161.534 (4)C35—C361.538 (4)
C10—C111.542 (4)C35—H350.9700
C10—H100.9800C35—H35B0.9700
C11—C121.545 (4)C36—C371.530 (4)
C11—H110.9800C36—H36A0.9700
C12—C131.539 (4)C36—H36B0.9700
C12—H12A0.9700C37—C381.534 (4)
C12—H12B0.9700C37—C391.548 (4)
C13—C141.528 (4)C37—C421.553 (4)
C13—H13A0.9700C38—H38A0.9600
C13—H13B0.9700C38—H38B0.9600
C14—C151.537 (4)C38—H38C0.9600
C14—C161.546 (4)C39—C401.530 (4)
C14—C191.558 (4)C39—H390.9800
C15—H15A0.9600C40—C411.518 (4)
C15—H15B0.9600C40—H40A0.9700
C15—H15C0.9600C40—H40B0.9700
C16—C171.533 (4)C41—C421.538 (4)
C16—H160.9800C42—C431.529 (4)
C17—C181.518 (4)C42—H420.9800
C17—H17A0.9700C43—C441.515 (4)
C17—H17B0.9700C43—H430.9800
C18—C191.538 (4)C44—H44A0.9600
C19—C201.523 (4)C44—H44B0.9600
C19—H190.9800C44—H44C0.9600
C20—C211.512 (4)C45—C461.498 (4)
C20—H200.9800C46—H46A0.9600
C21—H21A0.9600C46—H46B0.9600
C21—H21B0.9600C46—H46C0.9600
C22—O3—C20117.8 (2)H23B—C23—H23C109.5
C45—O7—C43118.4 (2)C25—C24—H24A109.5
C2—C1—H1A109.5C25—C24—H24B109.5
C2—C1—H1B109.5H24A—C24—H24B109.5
H1A—C1—H1B109.5C25—C24—H24C109.5
C2—C1—H1C109.5H24A—C24—H24C109.5
H1A—C1—H1C109.5H24B—C24—H24C109.5
H1B—C1—H1C109.5C30—C25—C26109.9 (2)
C7—C2—C1108.1 (2)C30—C25—C24107.9 (2)
C7—C2—C3109.8 (2)C26—C25—C24109.7 (2)
C1—C2—C3110.1 (3)C30—C25—C34109.3 (2)
C7—C2—C11109.3 (2)C26—C25—C34108.2 (2)
C1—C2—C11111.7 (2)C24—C25—C34111.8 (2)
C3—C2—C11107.8 (2)C27—C26—C25113.5 (2)
C4—C3—C2113.3 (3)C27—C26—H26A108.9
C4—C3—H3A108.9C25—C26—H26A108.9
C2—C3—H3A108.9C27—C26—H26B108.9
C4—C3—H3B108.9C25—C26—H26B108.9
C2—C3—H3B108.9H26A—C26—H26B107.7
H3A—C3—H3B107.7C28—C27—C26111.9 (3)
C5—C4—C3111.2 (3)C28—C27—H27A109.2
C5—C4—H4A109.4C26—C27—H27A109.2
C3—C4—H4A109.4C28—C27—H27B109.2
C5—C4—H4B109.4C26—C27—H27B109.2
C3—C4—H4B109.4H27A—C27—H27B107.9
H4A—C4—H4B108.0O5—C28—C29121.8 (3)
O1—C5—C6121.6 (3)O5—C28—C27121.7 (3)
O1—C5—C4122.6 (3)C29—C28—C27116.4 (3)
C6—C5—C4115.7 (3)C30—C29—C28124.1 (3)
C7—C6—C5124.3 (3)C30—C29—H29117.9
C7—C6—H6117.8C28—C29—H29117.9
C5—C6—H6117.8C29—C30—C31120.7 (3)
C6—C7—C8120.1 (3)C29—C30—C25122.5 (3)
C6—C7—C2122.7 (3)C31—C30—C25116.8 (3)
C8—C7—C2117.1 (3)C30—C31—C32112.1 (3)
C7—C8—C9111.3 (2)C30—C31—H31A109.2
C7—C8—H8A109.4C32—C31—H31A109.2
C9—C8—H8A109.4C30—C31—H31B109.2
C7—C8—H8B109.4C32—C31—H31B109.2
C9—C8—H8B109.4H31A—C31—H31B107.9
H8A—C8—H8B108.0C33—C32—C31110.1 (3)
C10—C9—C8110.0 (3)C33—C32—H32A109.6
C10—C9—H9A109.7C31—C32—H32A109.6
C8—C9—H9A109.7C33—C32—H32B109.6
C10—C9—H9B109.7C31—C32—H32B109.6
C8—C9—H9B109.7H32A—C32—H32B108.1
H9A—C9—H9B108.2C32—C33—C39111.3 (2)
C9—C10—C16111.7 (2)C32—C33—C34110.9 (2)
C9—C10—C11110.9 (2)C39—C33—C34108.0 (2)
C16—C10—C11107.3 (2)C32—C33—H33108.9
C9—C10—H10109.0C39—C33—H33108.9
C16—C10—H10109.0C34—C33—H33108.9
C11—C10—H10109.0C35—C34—C33111.7 (2)
C10—C11—C12111.1 (2)C35—C34—C25112.8 (2)
C10—C11—C2114.1 (2)C33—C34—C25114.1 (2)
C12—C11—C2112.4 (2)C35—C34—H34105.8
C10—C11—H11106.2C33—C34—H34105.8
C12—C11—H11106.2C25—C34—H34105.8
C2—C11—H11106.2C34—C35—C36113.5 (2)
C13—C12—C11113.5 (2)C34—C35—H35108.9
C13—C12—H12A108.9C36—C35—H35108.9
C11—C12—H12A108.9C34—C35—H35B108.9
C13—C12—H12B108.9C36—C35—H35B108.9
C11—C12—H12B108.9H35—C35—H35B107.7
H12A—C12—H12B107.7C37—C36—C35111.6 (2)
C14—C13—C12111.3 (2)C37—C36—H36A109.3
C14—C13—H13A109.4C35—C36—H36A109.3
C12—C13—H13A109.4C37—C36—H36B109.3
C14—C13—H13B109.4C35—C36—H36B109.3
C12—C13—H13B109.4H36A—C36—H36B108.0
H13A—C13—H13B108.0C36—C37—C38110.7 (2)
C13—C14—C15111.0 (2)C36—C37—C39107.0 (2)
C13—C14—C16107.1 (2)C38—C37—C39112.7 (2)
C15—C14—C16112.7 (2)C36—C37—C42116.8 (2)
C13—C14—C19116.4 (2)C38—C37—C42109.1 (2)
C15—C14—C19109.1 (2)C39—C37—C42100.1 (2)
C16—C14—C19100.1 (2)C37—C38—H38A109.5
C14—C15—H15A109.5C37—C38—H38B109.5
C14—C15—H15B109.5H38A—C38—H38B109.5
H15A—C15—H15B109.5C37—C38—H38C109.5
C14—C15—H15C109.5H38A—C38—H38C109.5
H15A—C15—H15C109.5H38B—C38—H38C109.5
H15B—C15—H15C109.5C33—C39—C40119.0 (2)
C17—C16—C10118.7 (2)C33—C39—C37113.6 (2)
C17—C16—C14104.6 (2)C40—C39—C37104.2 (2)
C10—C16—C14113.4 (2)C33—C39—H39106.4
C17—C16—H16106.4C40—C39—H39106.4
C10—C16—H16106.4C37—C39—H39106.4
C14—C16—H16106.4C41—C40—C39104.0 (2)
C18—C17—C16103.3 (2)C41—C40—H40A111.0
C18—C17—H17A111.1C39—C40—H40A111.0
C16—C17—H17A111.1C41—C40—H40B111.0
C18—C17—H17B111.1C39—C40—H40B111.0
C16—C17—H17B111.1H40A—C40—H40B109.0
H17A—C17—H17B109.1O6—C41—C40124.1 (3)
O2—C18—C17123.8 (3)O6—C41—C42127.3 (3)
O2—C18—C19127.0 (3)C40—C41—C42108.5 (2)
C17—C18—C19109.2 (2)C43—C42—C41115.0 (2)
C20—C19—C18114.8 (2)C43—C42—C37117.6 (2)
C20—C19—C14117.7 (2)C41—C42—C37102.0 (2)
C18—C19—C14101.8 (2)C43—C42—H42107.2
C20—C19—H19107.3C41—C42—H42107.2
C18—C19—H19107.3C37—C42—H42107.2
C14—C19—H19107.3O7—C43—C44106.1 (2)
O3—C20—C21106.5 (2)O7—C43—C42104.9 (2)
O3—C20—C19105.3 (2)C44—C43—C42116.0 (2)
C21—C20—C19115.3 (2)O7—C43—H43109.9
O3—C20—H20109.8C44—C43—H43109.9
C21—C20—H20109.8C42—C43—H43109.9
C19—C20—H20109.8C43—C44—H44A109.5
C20—C21—H21A109.5C43—C44—H44B109.5
C20—C21—H21B109.5H44A—C44—H44B109.5
H21A—C21—H21B109.5C43—C44—H44C109.5
C20—C21—H21C109.5H44A—C44—H44C109.5
H21A—C21—H21C109.5H44B—C44—H44C109.5
H21B—C21—H21C109.5O8—C45—O7123.9 (3)
O4—C22—O3124.0 (3)O8—C45—C46125.3 (3)
O4—C22—C23125.9 (3)O7—C45—C46110.8 (2)
O3—C22—C23110.2 (3)C45—C46—H46A109.5
C22—C23—H23A109.5C45—C46—H46B109.5
C22—C23—H23B109.5H46A—C46—H46B109.5
H23A—C23—H23B109.5C45—C46—H46C109.5
C22—C23—H23C109.5H46A—C46—H46C109.5
H23A—C23—H23C109.5H46B—C46—H46C109.5
C7—C2—C3—C445.7 (4)C30—C25—C26—C2746.1 (3)
C1—C2—C3—C4−73.2 (3)C24—C25—C26—C27−72.4 (3)
C11—C2—C3—C4164.8 (3)C34—C25—C26—C27165.3 (3)
C2—C3—C4—C5−55.9 (4)C25—C26—C27—C28−54.0 (4)
C3—C4—C5—O1−146.1 (3)C26—C27—C28—O5−152.6 (3)
C3—C4—C5—C635.0 (4)C26—C27—C28—C2930.9 (4)
O1—C5—C6—C7174.6 (3)O5—C28—C29—C30−178.2 (3)
C4—C5—C6—C7−6.5 (4)C27—C28—C29—C30−1.7 (4)
C5—C6—C7—C8175.6 (3)C28—C29—C30—C31172.1 (3)
C5—C6—C7—C2−3.0 (5)C28—C29—C30—C25−5.4 (5)
C1—C2—C7—C6103.3 (3)C26—C25—C30—C29−17.0 (4)
C3—C2—C7—C6−16.9 (4)C24—C25—C30—C29102.6 (3)
C11—C2—C7—C6−135.0 (3)C34—C25—C30—C29−135.6 (3)
C1—C2—C7—C8−75.4 (3)C26—C25—C30—C31165.4 (3)
C3—C2—C7—C8164.5 (3)C24—C25—C30—C31−75.0 (3)
C11—C2—C7—C846.4 (3)C34—C25—C30—C3146.8 (3)
C6—C7—C8—C9128.6 (3)C29—C30—C31—C32130.3 (3)
C2—C7—C8—C9−52.7 (4)C25—C30—C31—C32−52.1 (4)
C7—C8—C9—C1056.5 (3)C30—C31—C32—C3355.3 (4)
C8—C9—C10—C16−177.8 (2)C31—C32—C33—C39−177.2 (2)
C8—C9—C10—C11−58.1 (3)C31—C32—C33—C34−56.9 (3)
C9—C10—C11—C12−177.0 (2)C32—C33—C34—C35−175.6 (2)
C16—C10—C11—C12−54.8 (3)C39—C33—C34—C35−53.4 (3)
C9—C10—C11—C254.6 (3)C32—C33—C34—C2555.0 (3)
C16—C10—C11—C2176.9 (2)C39—C33—C34—C25177.1 (2)
C7—C2—C11—C10−46.7 (3)C30—C25—C34—C35−176.6 (2)
C1—C2—C11—C1072.9 (3)C26—C25—C34—C3563.7 (3)
C3—C2—C11—C10−166.0 (2)C24—C25—C34—C35−57.2 (3)
C7—C2—C11—C12−174.4 (2)C30—C25—C34—C33−47.8 (3)
C1—C2—C11—C12−54.8 (3)C26—C25—C34—C33−167.4 (2)
C3—C2—C11—C1266.3 (3)C24—C25—C34—C3371.6 (3)
C10—C11—C12—C1353.1 (3)C33—C34—C35—C3652.0 (3)
C2—C11—C12—C13−177.6 (2)C25—C34—C35—C36−177.9 (2)
C11—C12—C13—C14−53.8 (3)C34—C35—C36—C37−53.6 (3)
C12—C13—C14—C15−67.9 (3)C35—C36—C37—C38−67.5 (3)
C12—C13—C14—C1655.5 (3)C35—C36—C37—C3955.6 (3)
C12—C13—C14—C19166.6 (2)C35—C36—C37—C42166.8 (2)
C9—C10—C16—C17−53.0 (3)C32—C33—C39—C40−54.3 (3)
C11—C10—C16—C17−174.8 (2)C34—C33—C39—C40−176.2 (2)
C9—C10—C16—C14−176.4 (2)C32—C33—C39—C37−177.6 (2)
C11—C10—C16—C1461.8 (3)C34—C33—C39—C3760.5 (3)
C13—C14—C16—C17166.9 (2)C36—C37—C39—C33−61.6 (3)
C15—C14—C16—C17−70.7 (3)C38—C37—C39—C3360.3 (3)
C19—C14—C16—C1745.0 (3)C42—C37—C39—C33176.1 (2)
C13—C14—C16—C10−62.3 (3)C36—C37—C39—C40167.3 (2)
C15—C14—C16—C1060.1 (3)C38—C37—C39—C40−70.8 (3)
C19—C14—C16—C10175.9 (2)C42—C37—C39—C4045.0 (3)
C10—C16—C17—C18−158.1 (2)C33—C39—C40—C41−157.7 (2)
C14—C16—C17—C18−30.4 (3)C37—C39—C40—C41−29.9 (3)
C16—C17—C18—O2−176.4 (3)C39—C40—C41—O6−177.9 (3)
C16—C17—C18—C193.8 (3)C39—C40—C41—C422.8 (3)
O2—C18—C19—C20−27.7 (4)O6—C41—C42—C43−26.0 (4)
C17—C18—C19—C20152.0 (2)C40—C41—C42—C43153.2 (2)
O2—C18—C19—C14−156.1 (3)O6—C41—C42—C37−154.3 (3)
C17—C18—C19—C1423.7 (3)C40—C41—C42—C3724.9 (3)
C13—C14—C19—C2077.6 (3)C36—C37—C42—C4376.4 (3)
C15—C14—C19—C20−48.9 (3)C38—C37—C42—C43−50.1 (3)
C16—C14—C19—C20−167.4 (2)C39—C37—C42—C43−168.6 (2)
C13—C14—C19—C18−156.0 (2)C36—C37—C42—C41−156.9 (2)
C15—C14—C19—C1877.5 (3)C38—C37—C42—C4176.6 (3)
C16—C14—C19—C18−41.0 (2)C39—C37—C42—C41−41.9 (2)
C22—O3—C20—C21−91.5 (3)C45—O7—C43—C44−95.8 (3)
C22—O3—C20—C19145.7 (2)C45—O7—C43—C42141.0 (2)
C18—C19—C20—O3179.4 (2)C41—C42—C43—O7177.4 (2)
C14—C19—C20—O3−60.8 (3)C37—C42—C43—O7−62.5 (3)
C18—C19—C20—C2162.3 (3)C41—C42—C43—C4460.7 (3)
C14—C19—C20—C21−177.8 (2)C37—C42—C43—C44−179.2 (3)
C20—O3—C22—O4−8.6 (4)C43—O7—C45—O8−7.9 (4)
C20—O3—C22—C23171.8 (2)C43—O7—C45—C46173.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C23—H23B···O2i0.962.463.393 (4)165
C46—H46B···O6i0.962.493.431 (4)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5092).

References

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  • Hung, T., Stuppner, H., Ellmerer-Müller, E. P., Scholz, D., Eigner, D. & Manandhar, M. P. (1995). Phytochemistry, 39, 1403–1409.
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  • Zhu, N., Rafi, M. M., DiPaloa, R. S., Xing, J. S., Chin, C.-K., Badmaey, V. G., Rosen, R. T. & Ho, C.-T. (2001). Phytochemistry, 56, 723–727. [PubMed]

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