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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1872.
Published online 2009 July 15. doi:  10.1107/S1600536809026695
PMCID: PMC2977140

Benzyl 3-dehydr­oxy-1,2,5-oxadiazolo[3′,4′:2,3]oleanolate

Abstract

The title compound, C37H50N2O3, is a benzyl ester derivative of oleanolic acid, a penta­cyclic triterpene, with a five-membered oxadiazole ring fused to the ring A. The triterpene A and C rings adopt slightly distorted half-chair conformations, whereas the remaining three six-membered rings are in chair forms.

Related literature

For information on oleanolic acid and its derivatives, see: Chen et al. (2006 [triangle]); Liu (2005 [triangle]).

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Object name is e-65-o1872-scheme1.jpg

Experimental

Crystal data

  • C37H50N2O3
  • M r = 570.79
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1872-efi1.jpg
  • a = 8.7124 (19) Å
  • b = 19.054 (3) Å
  • c = 19.480 (3) Å
  • V = 3233.7 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 295 K
  • 0.4 × 0.3 × 0.2 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: none
  • 4315 measured reflections
  • 3398 independent reflections
  • 1649 reflections with I > 2σ(I)
  • R int = 0.060
  • 3 standard reflections every 97 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.131
  • S = 1.00
  • 3398 reflections
  • 381 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: XSCANS (Bruker, 1997 [triangle]); cell refinement: XSCANS; data reduction: XSCANS; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026695/gk2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026695/gk2215Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from NSFC (grant No. 20772071)

supplementary crystallographic information

Comment

Recently, our group has designed and synthesized a novel series of oleanolic acid derivatives by chemical modification. Oleanolic acid is a pentacyclic triterpenoid with interesting biological activities that has been isolated from many medicinal plants (Liu, 2005). As our studies show the title compound, first reported by Chen et al. (2006), inhibits considerably growth of HepG-2 tumour cells and therefore its crystal structure is reported here.

The title compound was obtained as colourless plates. A view of the molecular structure with the numbering scheme is shown in Fig. 1. The molecule is composed of five fused six-membered rings, a five-membered heterocyclic ring and an independent benzene ring, viz. A(C1–C5/C10), B(C5–C10), C(C8/C9/C11–C14), D(C13–C18), E(C17–C22), F(C2—N2—O2—N1—C3) and G(C32–C37). The rings B, D and E adopt chair conformations, while the rings A and C adopt a slightly distorted half-chair conformation as a result of the presence of endo or exo double bonds. The lengths of double bonds N1–C3 and N2–C2 are nearly equal, even though they are in non-symmetrical environment.

Experimental

Benzyl 2,3-dihydroxyiminooleanolate (500 mg, 0.85 mmol), 18-crown-6 (30 mg, 0.11 mmol) and t-BuOK (190 mg, 1.70 mmol) were dissolved in 15 ml tetrahydrofurane and 15 ml dichloromethane. The mixture was stirred for 10 min at 50°C. The product was treated with hydrochloric acid, then washed with water and extracted with ethyl acetate. The combined organic phase was washed with brine, dried and evaporated. Purification by flash chromatography (dichloromethane:methanol =100:1) gave title compound (456 mg; yield 94%). Crystals suitable for X-ray structure analysis were obtained via slow evaporation of a chloroform/acetone solution ( 1:5 vol.) at room temperature.

Refinement

In the absence of significant anomalous scattering Friedel pairs were merged. The enantiomer has been assigned by reference to unchanging chiral centers in the synthetic procedure. All hydrogen atoms were generated geometrically with C—H bonds of 0.93–0.98 Å according to criteria described in the SHELXTL manual (Bruker, 1997a). They were included in the refinement with Uiso(H) = 1.2Ueq(C), except methyl groups where Uiso(H) = 1.5Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound with 35% probability displacement ellipsoids, showing the atomic numbering scheme.

Crystal data

C37H50N2O3F(000) = 1240
Mr = 570.79Dx = 1.172 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 49 reflections
a = 8.7124 (19) Åθ = 2.1–15.1°
b = 19.054 (3) ŵ = 0.07 mm1
c = 19.480 (3) ÅT = 295 K
V = 3233.7 (10) Å3Prism, colorless
Z = 40.4 × 0.3 × 0.2 mm

Data collection

Bruker P4 diffractometerRint = 0.060
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 2.1°
graphiteh = −1→10
ω scansk = −23→1
4315 measured reflectionsl = −1→23
3398 independent reflections3 standard reflections every 97 reflections
1649 reflections with I > 2σ(I) intensity decay: none

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.131w = 1/[σ2(Fo2) + (0.001P)2 + 1.8P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.008
3398 reflectionsΔρmax = 0.16 e Å3
381 parametersΔρmin = −0.22 e Å3
1 restraintExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00114 (8)

Special details

Experimental. absolute configuration has not been established by anomalous dispersion effects in diffraction measurements on the crystal. The enantiomer has been assigned by reference to unchanging chiral centres in the synthetic procedure. The Friedel pairs were averaged in the final refinement because the Mo Kα radiation was used and the compound was made of C, H, N and O.
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.
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
O11.1911 (2)0.29241 (10)0.64263 (10)0.0744 (7)
O20.4830 (2)0.57882 (10)0.26204 (9)0.0712 (6)
O30.2427 (2)0.55498 (10)0.29343 (10)0.0716 (6)
N11.0434 (3)0.26443 (11)0.64843 (12)0.0666 (8)
N21.1866 (3)0.35735 (12)0.60900 (12)0.0664 (8)
C10.9740 (3)0.42957 (13)0.55969 (15)0.0616 (9)
H1A1.04690.44750.52640.074*
H1B0.95140.46670.59220.074*
C21.0416 (3)0.36797 (13)0.59652 (13)0.0537 (8)
C30.9526 (3)0.31095 (13)0.62036 (14)0.0538 (8)
C40.7825 (3)0.30445 (13)0.61483 (14)0.0551 (9)
C50.7189 (3)0.37107 (12)0.57597 (13)0.0513 (8)
H5A0.70440.40640.61190.062*
C60.5586 (3)0.35847 (13)0.54702 (15)0.0601 (9)
H6A0.49630.33440.58090.072*
H6B0.56540.32890.50660.072*
C70.4830 (3)0.42843 (13)0.52804 (14)0.0584 (9)
H7A0.47050.45620.56940.070*
H7B0.38150.41910.50970.070*
C80.5739 (3)0.47144 (12)0.47542 (13)0.0486 (8)
C90.7459 (3)0.47566 (12)0.49632 (13)0.0478 (8)
H9A0.74810.50770.53570.057*
C100.8244 (3)0.40676 (12)0.52265 (14)0.0488 (8)
C110.8355 (3)0.51355 (12)0.44024 (14)0.0544 (8)
H11A0.93200.52990.45930.065*
H11B0.85930.48040.40400.065*
C120.7521 (3)0.57467 (13)0.40973 (13)0.0535 (8)
H12A0.80760.60330.38010.064*
C130.6062 (3)0.59207 (12)0.42089 (13)0.0476 (8)
C140.5073 (3)0.54920 (12)0.47100 (13)0.0482 (8)
C150.3371 (3)0.54676 (13)0.44892 (15)0.0582 (9)
H15A0.32450.50990.41500.070*
H15B0.27520.53440.48850.070*
C160.2764 (3)0.61563 (12)0.41882 (13)0.0555 (9)
H16A0.17170.60860.40340.067*
H16B0.27490.65100.45460.067*
C170.3727 (3)0.64233 (13)0.35880 (14)0.0527 (8)
C180.5388 (3)0.65564 (12)0.38321 (13)0.0528 (8)
H18A0.60140.66300.34200.063*
C190.5519 (3)0.72292 (12)0.42714 (13)0.0573 (9)
H19A0.50030.71510.47060.069*
H19B0.65940.73160.43690.069*
C200.4830 (4)0.78871 (12)0.39294 (14)0.0590 (9)
C210.3161 (3)0.77305 (13)0.37401 (14)0.0595 (9)
H21A0.25780.76480.41560.071*
H21B0.27240.81370.35120.071*
C220.3016 (3)0.70920 (13)0.32701 (14)0.0590 (9)
H22A0.35230.71920.28370.071*
H22B0.19390.70070.31750.071*
C230.7150 (4)0.30364 (15)0.68788 (14)0.0743 (10)
H23A0.75260.26330.71220.112*
H23B0.60500.30150.68530.112*
H23C0.74510.34550.71170.112*
C240.7422 (4)0.23391 (13)0.57912 (16)0.0779 (11)
H24A0.78360.23370.53340.117*
H24B0.63270.22870.57700.117*
H24C0.78530.19570.60480.117*
C250.8705 (3)0.35522 (13)0.46425 (14)0.0644 (9)
H25A0.78000.33940.44080.097*
H25B0.92330.31560.48350.097*
H25C0.93680.37880.43230.097*
C260.5545 (3)0.43558 (13)0.40356 (13)0.0616 (9)
H26A0.44780.42590.39560.092*
H26B0.61150.39250.40270.092*
H26C0.59220.46640.36840.092*
C270.5144 (3)0.58773 (12)0.54287 (12)0.0602 (9)
H27A0.47320.63420.53840.090*
H27B0.61910.59040.55800.090*
H27C0.45510.56190.57580.090*
C280.4855 (4)0.85000 (13)0.44522 (15)0.0815 (11)
H28A0.58970.86060.45730.122*
H28B0.42960.83670.48570.122*
H28C0.43860.89070.42510.122*
C290.5774 (4)0.81142 (14)0.33019 (15)0.0767 (11)
H29A0.57880.77410.29710.115*
H29B0.68050.82190.34420.115*
H29C0.53190.85250.31010.115*
C300.3771 (3)0.58947 (14)0.30003 (14)0.0593 (9)
C310.2337 (4)0.50425 (15)0.23783 (15)0.0753 (10)
H31A0.31750.47090.24100.090*
H31B0.23990.52780.19380.090*
C320.0835 (3)0.46753 (14)0.24481 (14)0.0614 (9)
C330.0760 (4)0.39893 (15)0.26336 (16)0.0816 (12)
H33A0.16680.37440.27080.098*
C34−0.0612 (4)0.36458 (17)0.27150 (17)0.0924 (13)
H34A−0.06340.31740.28370.111*
C35−0.1919 (4)0.40016 (18)0.26151 (17)0.0987 (13)
H35A−0.28490.37710.26820.118*
C36−0.1941 (4)0.4695 (2)0.24168 (16)0.0971 (13)
H36A−0.28580.49300.23340.116*
C37−0.0519 (4)0.50313 (16)0.23452 (15)0.0804 (11)
H37A−0.04900.55040.22260.096*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0625 (13)0.0800 (13)0.0808 (13)0.0098 (12)−0.0046 (12)0.0181 (12)
O20.0653 (12)0.0774 (12)0.0710 (12)−0.0048 (12)0.0123 (12)−0.0125 (11)
O30.0688 (13)0.0741 (11)0.0718 (12)−0.0144 (13)0.0066 (12)−0.0206 (11)
N10.0565 (15)0.0613 (13)0.0820 (16)0.0021 (14)−0.0040 (15)0.0038 (14)
N20.0561 (14)0.0712 (14)0.0720 (15)0.0048 (14)0.0006 (15)0.0129 (14)
C10.0469 (15)0.0509 (14)0.087 (2)−0.0029 (15)−0.0043 (17)0.0110 (16)
C20.0470 (16)0.0578 (15)0.0564 (16)0.0052 (15)0.0004 (15)−0.0019 (14)
C30.0513 (16)0.0497 (14)0.0603 (17)−0.0033 (15)−0.0011 (16)0.0004 (14)
C40.0536 (16)0.0426 (13)0.0691 (18)−0.0012 (14)−0.0076 (17)0.0090 (15)
C50.0541 (16)0.0429 (13)0.0570 (16)−0.0053 (14)−0.0005 (15)0.0004 (13)
C60.0482 (16)0.0533 (15)0.0789 (19)−0.0037 (15)−0.0041 (17)0.0129 (16)
C70.0508 (16)0.0536 (15)0.0708 (18)−0.0008 (15)−0.0001 (17)0.0126 (15)
C80.0447 (15)0.0458 (13)0.0553 (15)−0.0034 (14)0.0071 (14)−0.0011 (13)
C90.0456 (14)0.0447 (13)0.0531 (15)0.0027 (14)0.0036 (14)−0.0006 (13)
C100.0445 (15)0.0405 (13)0.0613 (16)−0.0005 (13)0.0034 (15)0.0068 (13)
C110.0519 (16)0.0456 (14)0.0656 (17)0.0032 (14)0.0037 (16)0.0070 (14)
C120.0586 (17)0.0491 (14)0.0530 (15)−0.0001 (16)0.0016 (16)0.0063 (14)
C130.0518 (16)0.0414 (13)0.0498 (15)0.0030 (14)0.0026 (15)0.0009 (13)
C140.0468 (15)0.0438 (13)0.0540 (15)0.0008 (13)0.0081 (15)0.0018 (13)
C150.0487 (16)0.0581 (16)0.0679 (17)0.0012 (15)0.0051 (16)0.0062 (16)
C160.0557 (17)0.0541 (15)0.0566 (16)0.0067 (16)−0.0029 (16)0.0062 (14)
C170.0530 (16)0.0514 (14)0.0537 (16)0.0034 (15)0.0049 (15)0.0054 (14)
C180.0619 (18)0.0429 (13)0.0536 (16)0.0046 (15)−0.0007 (16)0.0061 (13)
C190.0622 (18)0.0486 (14)0.0609 (17)0.0049 (16)−0.0081 (17)0.0037 (14)
C200.072 (2)0.0411 (13)0.0638 (17)−0.0008 (16)0.0027 (18)−0.0011 (14)
C210.0629 (18)0.0579 (16)0.0578 (17)0.0085 (17)−0.0036 (17)0.0028 (15)
C220.0648 (19)0.0524 (15)0.0598 (16)0.0023 (17)−0.0090 (17)0.0011 (15)
C230.066 (2)0.0791 (19)0.078 (2)−0.0034 (19)0.0058 (19)0.0283 (18)
C240.070 (2)0.0465 (15)0.117 (3)−0.0008 (18)−0.015 (2)−0.0007 (19)
C250.0627 (18)0.0582 (16)0.0722 (19)0.0106 (17)0.0095 (18)−0.0040 (16)
C260.0556 (17)0.0552 (15)0.0739 (19)−0.0023 (17)−0.0038 (18)−0.0032 (16)
C270.0718 (19)0.0519 (15)0.0568 (16)0.0080 (16)0.0083 (18)0.0032 (14)
C280.102 (3)0.0570 (17)0.085 (2)0.018 (2)−0.016 (2)−0.0103 (18)
C290.085 (2)0.0624 (17)0.083 (2)0.000 (2)0.006 (2)0.0221 (17)
C300.0629 (18)0.0577 (16)0.0572 (17)0.0024 (17)0.0026 (17)0.0015 (15)
C310.080 (2)0.0779 (18)0.0681 (18)−0.017 (2)0.005 (2)−0.0234 (17)
C320.0621 (18)0.0638 (17)0.0584 (17)0.0028 (17)0.0008 (17)−0.0110 (15)
C330.085 (2)0.0689 (19)0.091 (2)0.012 (2)−0.012 (2)−0.0114 (19)
C340.109 (3)0.0729 (19)0.095 (2)−0.023 (2)0.015 (3)−0.013 (2)
C350.089 (2)0.125 (3)0.082 (2)−0.034 (2)0.013 (2)−0.043 (2)
C360.073 (2)0.146 (3)0.071 (2)0.032 (3)−0.014 (2)−0.023 (2)
C370.090 (2)0.078 (2)0.074 (2)0.011 (2)−0.005 (2)−0.0125 (18)

Geometric parameters (Å, °)

O1—N11.398 (3)C17—C221.546 (4)
O1—N21.401 (3)C18—C191.545 (3)
O2—C301.200 (3)C18—H18A0.9800
O3—C301.349 (3)C19—C201.541 (3)
O3—C311.454 (3)C19—H19A0.9700
N1—C31.308 (3)C19—H19B0.9700
N2—C21.302 (4)C20—C211.529 (4)
C1—C21.497 (4)C20—C291.536 (4)
C1—C101.551 (4)C20—C281.550 (4)
C1—H1A0.9700C21—C221.528 (4)
C1—H1B0.9700C21—H21A0.9700
C2—C31.413 (4)C21—H21B0.9700
C3—C41.491 (4)C22—H22A0.9700
C4—C231.540 (4)C22—H22B0.9700
C4—C241.554 (4)C23—H23A0.9600
C4—C51.579 (3)C23—H23B0.9600
C5—C61.525 (4)C23—H23C0.9600
C5—C101.545 (4)C24—H24A0.9600
C5—H5A0.9800C24—H24B0.9600
C6—C71.532 (3)C24—H24C0.9600
C6—H6A0.9700C25—H25A0.9600
C6—H6B0.9700C25—H25B0.9600
C7—C81.533 (3)C25—H25C0.9600
C7—H7A0.9700C26—H26A0.9600
C7—H7B0.9700C26—H26B0.9600
C8—C91.555 (4)C26—H26C0.9600
C8—C261.567 (3)C27—H27A0.9600
C8—C141.593 (3)C27—H27B0.9600
C9—C111.524 (3)C27—H27C0.9600
C9—C101.567 (3)C28—H28A0.9600
C9—H9A0.9800C28—H28B0.9600
C10—C251.556 (4)C28—H28C0.9600
C11—C121.496 (3)C29—H29A0.9600
C11—H11A0.9700C29—H29B0.9600
C11—H11B0.9700C29—H29C0.9600
C12—C131.332 (4)C31—C321.490 (4)
C12—H12A0.9300C31—H31A0.9700
C13—C181.533 (3)C31—H31B0.9700
C13—C141.537 (3)C32—C331.358 (4)
C14—C151.545 (4)C32—C371.376 (4)
C14—C271.582 (3)C33—C341.372 (5)
C15—C161.531 (3)C33—H33A0.9300
C15—H15A0.9700C34—C351.340 (5)
C15—H15B0.9700C34—H34A0.9300
C16—C171.526 (4)C35—C361.377 (5)
C16—H16A0.9700C35—H35A0.9300
C16—H16B0.9700C36—C371.402 (5)
C17—C301.525 (4)C36—H36A0.9300
C17—C181.544 (4)C37—H37A0.9300
N1—O1—N2110.42 (19)C13—C18—H18A107.0
C30—O3—C31116.2 (2)C17—C18—H18A107.0
C3—N1—O1105.3 (2)C19—C18—H18A107.0
C2—N2—O1104.6 (2)C20—C19—C18114.0 (2)
C2—C1—C10109.5 (2)C20—C19—H19A108.8
C2—C1—H1A109.8C18—C19—H19A108.8
C10—C1—H1A109.8C20—C19—H19B108.8
C2—C1—H1B109.8C18—C19—H19B108.8
C10—C1—H1B109.8H19A—C19—H19B107.6
H1A—C1—H1B108.2C21—C20—C29111.9 (2)
N2—C2—C3110.6 (2)C21—C20—C19108.4 (2)
N2—C2—C1126.4 (2)C29—C20—C19111.4 (2)
C3—C2—C1123.0 (2)C21—C20—C28108.6 (2)
N1—C3—C2109.1 (2)C29—C20—C28107.7 (2)
N1—C3—C4125.1 (2)C19—C20—C28108.9 (2)
C2—C3—C4125.8 (2)C22—C21—C20112.2 (2)
C3—C4—C23108.3 (2)C22—C21—H21A109.2
C3—C4—C24109.2 (2)C20—C21—H21A109.2
C23—C4—C24108.6 (2)C22—C21—H21B109.2
C3—C4—C5108.5 (2)C20—C21—H21B109.2
C23—C4—C5108.5 (2)H21A—C21—H21B107.9
C24—C4—C5113.7 (2)C21—C22—C17112.5 (2)
C6—C5—C10111.5 (2)C21—C22—H22A109.1
C6—C5—C4111.9 (2)C17—C22—H22A109.1
C10—C5—C4117.8 (2)C21—C22—H22B109.1
C6—C5—H5A104.8C17—C22—H22B109.1
C10—C5—H5A104.8H22A—C22—H22B107.8
C4—C5—H5A104.8C4—C23—H23A109.5
C5—C6—C7110.2 (2)C4—C23—H23B109.5
C5—C6—H6A109.6H23A—C23—H23B109.5
C7—C6—H6A109.6C4—C23—H23C109.5
C5—C6—H6B109.6H23A—C23—H23C109.5
C7—C6—H6B109.6H23B—C23—H23C109.5
H6A—C6—H6B108.1C4—C24—H24A109.5
C6—C7—C8113.8 (2)C4—C24—H24B109.5
C6—C7—H7A108.8H24A—C24—H24B109.5
C8—C7—H7A108.8C4—C24—H24C109.5
C6—C7—H7B108.8H24A—C24—H24C109.5
C8—C7—H7B108.8H24B—C24—H24C109.5
H7A—C7—H7B107.7C10—C25—H25A109.5
C7—C8—C9110.5 (2)C10—C25—H25B109.5
C7—C8—C26107.9 (2)H25A—C25—H25B109.5
C9—C8—C26111.2 (2)C10—C25—H25C109.5
C7—C8—C14110.2 (2)H25A—C25—H25C109.5
C9—C8—C14108.48 (19)H25B—C25—H25C109.5
C26—C8—C14108.5 (2)C8—C26—H26A109.5
C11—C9—C8109.3 (2)C8—C26—H26B109.5
C11—C9—C10114.1 (2)H26A—C26—H26B109.5
C8—C9—C10117.6 (2)C8—C26—H26C109.5
C11—C9—H9A104.8H26A—C26—H26C109.5
C8—C9—H9A104.8H26B—C26—H26C109.5
C10—C9—H9A104.8C14—C27—H27A109.5
C5—C10—C1108.1 (2)C14—C27—H27B109.5
C5—C10—C25111.6 (2)H27A—C27—H27B109.5
C1—C10—C25107.5 (2)C14—C27—H27C109.5
C5—C10—C9109.2 (2)H27A—C27—H27C109.5
C1—C10—C9106.51 (19)H27B—C27—H27C109.5
C25—C10—C9113.7 (2)C20—C28—H28A109.5
C12—C11—C9113.9 (2)C20—C28—H28B109.5
C12—C11—H11A108.8H28A—C28—H28B109.5
C9—C11—H11A108.8C20—C28—H28C109.5
C12—C11—H11B108.8H28A—C28—H28C109.5
C9—C11—H11B108.8H28B—C28—H28C109.5
H11A—C11—H11B107.7C20—C29—H29A109.5
C13—C12—C11126.4 (2)C20—C29—H29B109.5
C13—C12—H12A116.8H29A—C29—H29B109.5
C11—C12—H12A116.8C20—C29—H29C109.5
C12—C13—C18119.0 (2)H29A—C29—H29C109.5
C12—C13—C14120.4 (2)H29B—C29—H29C109.5
C18—C13—C14120.6 (2)O2—C30—O3121.8 (3)
C13—C14—C15112.1 (2)O2—C30—C17126.4 (3)
C13—C14—C27107.1 (2)O3—C30—C17111.8 (2)
C15—C14—C27107.3 (2)O3—C31—C32106.9 (2)
C13—C14—C8108.9 (2)O3—C31—H31A110.3
C15—C14—C8109.7 (2)C32—C31—H31A110.3
C27—C14—C8111.70 (19)O3—C31—H31B110.3
C16—C15—C14114.4 (2)C32—C31—H31B110.3
C16—C15—H15A108.7H31A—C31—H31B108.6
C14—C15—H15A108.7C33—C32—C37118.2 (3)
C16—C15—H15B108.7C33—C32—C31121.2 (3)
C14—C15—H15B108.7C37—C32—C31120.6 (3)
H15A—C15—H15B107.6C32—C33—C34122.1 (3)
C17—C16—C15112.9 (2)C32—C33—H33A118.9
C17—C16—H16A109.0C34—C33—H33A118.9
C15—C16—H16A109.0C35—C34—C33118.9 (3)
C17—C16—H16B109.0C35—C34—H34A120.6
C15—C16—H16B109.0C33—C34—H34A120.6
H16A—C16—H16B107.8C34—C35—C36122.5 (4)
C30—C17—C16111.6 (2)C34—C35—H35A118.7
C30—C17—C18108.4 (2)C36—C35—H35A118.7
C16—C17—C18109.5 (2)C35—C36—C37117.1 (3)
C30—C17—C22104.7 (2)C35—C36—H36A121.5
C16—C17—C22111.2 (2)C37—C36—H36A121.5
C18—C17—C22111.3 (2)C32—C37—C36121.2 (3)
C13—C18—C17112.1 (2)C32—C37—H37A119.4
C13—C18—C19111.2 (2)C36—C37—H37A119.4
C17—C18—C19112.1 (2)
N2—O1—N1—C3−0.9 (3)C12—C13—C14—C8−25.8 (3)
N1—O1—N2—C21.1 (3)C18—C13—C14—C8154.5 (2)
O1—N2—C2—C3−0.9 (3)C7—C8—C14—C13176.9 (2)
O1—N2—C2—C1−178.5 (2)C9—C8—C14—C1355.8 (3)
C10—C1—C2—N2150.4 (3)C26—C8—C14—C13−65.1 (3)
C10—C1—C2—C3−26.9 (4)C7—C8—C14—C15−60.0 (3)
O1—N1—C3—C20.3 (3)C9—C8—C14—C15178.9 (2)
O1—N1—C3—C4−179.5 (2)C26—C8—C14—C1558.0 (3)
N2—C2—C3—N10.4 (3)C7—C8—C14—C2758.9 (3)
C1—C2—C3—N1178.1 (2)C9—C8—C14—C27−62.3 (3)
N2—C2—C3—C4−179.8 (3)C26—C8—C14—C27176.8 (2)
C1—C2—C3—C4−2.1 (4)C13—C14—C15—C16−38.5 (3)
N1—C3—C4—C2363.8 (3)C27—C14—C15—C1678.8 (3)
C2—C3—C4—C23−116.0 (3)C8—C14—C15—C16−159.6 (2)
N1—C3—C4—C24−54.2 (4)C14—C15—C16—C1754.7 (3)
C2—C3—C4—C24125.9 (3)C15—C16—C17—C3059.8 (3)
N1—C3—C4—C5−178.6 (2)C15—C16—C17—C18−60.3 (3)
C2—C3—C4—C51.6 (4)C15—C16—C17—C22176.3 (2)
C3—C4—C5—C6160.9 (2)C12—C13—C18—C17140.0 (2)
C23—C4—C5—C6−81.6 (3)C14—C13—C18—C17−40.2 (3)
C24—C4—C5—C639.2 (3)C12—C13—C18—C19−93.6 (3)
C3—C4—C5—C1029.8 (3)C14—C13—C18—C1986.1 (3)
C23—C4—C5—C10147.2 (2)C30—C17—C18—C13−70.7 (3)
C24—C4—C5—C10−91.9 (3)C16—C17—C18—C1351.4 (3)
C10—C5—C6—C7−61.6 (3)C22—C17—C18—C13174.7 (2)
C4—C5—C6—C7164.1 (2)C30—C17—C18—C19163.4 (2)
C5—C6—C7—C858.4 (3)C16—C17—C18—C19−74.6 (3)
C6—C7—C8—C9−47.9 (3)C22—C17—C18—C1948.8 (3)
C6—C7—C8—C2673.9 (3)C13—C18—C19—C20−178.7 (2)
C6—C7—C8—C14−167.8 (2)C17—C18—C19—C20−52.3 (3)
C7—C8—C9—C11175.45 (19)C18—C19—C20—C2155.3 (3)
C26—C8—C9—C1155.6 (3)C18—C19—C20—C29−68.2 (3)
C14—C8—C9—C11−63.7 (2)C18—C19—C20—C28173.2 (2)
C7—C8—C9—C1043.3 (3)C29—C20—C21—C2266.0 (3)
C26—C8—C9—C10−76.5 (3)C19—C20—C21—C22−57.2 (3)
C14—C8—C9—C10164.2 (2)C28—C20—C21—C22−175.3 (2)
C6—C5—C10—C1170.1 (2)C20—C21—C22—C1757.3 (3)
C4—C5—C10—C1−58.6 (3)C30—C17—C22—C21−168.8 (2)
C6—C5—C10—C25−72.0 (3)C16—C17—C22—C2170.6 (3)
C4—C5—C10—C2559.3 (3)C18—C17—C22—C21−51.8 (3)
C6—C5—C10—C954.6 (3)C31—O3—C30—O20.1 (4)
C4—C5—C10—C9−174.1 (2)C31—O3—C30—C17178.8 (2)
C2—C1—C10—C553.2 (3)C16—C17—C30—O2−145.9 (3)
C2—C1—C10—C25−67.3 (3)C18—C17—C30—O2−25.2 (4)
C2—C1—C10—C9170.4 (2)C22—C17—C30—O293.7 (3)
C11—C9—C10—C5−176.7 (2)C16—C17—C30—O335.4 (3)
C8—C9—C10—C5−46.8 (3)C18—C17—C30—O3156.1 (2)
C11—C9—C10—C166.8 (3)C22—C17—C30—O3−85.0 (3)
C8—C9—C10—C1−163.3 (2)C30—O3—C31—C32174.1 (2)
C11—C9—C10—C25−51.4 (3)O3—C31—C32—C33−111.0 (3)
C8—C9—C10—C2578.5 (3)O3—C31—C32—C3767.0 (3)
C8—C9—C11—C1239.5 (3)C37—C32—C33—C340.5 (5)
C10—C9—C11—C12173.5 (2)C31—C32—C33—C34178.6 (3)
C9—C11—C12—C13−8.8 (4)C32—C33—C34—C35−0.7 (5)
C11—C12—C13—C18−178.2 (2)C33—C34—C35—C361.7 (5)
C11—C12—C13—C142.1 (4)C34—C35—C36—C37−2.3 (5)
C12—C13—C14—C15−147.4 (2)C33—C32—C37—C36−1.1 (4)
C18—C13—C14—C1532.9 (3)C31—C32—C37—C36−179.3 (3)
C12—C13—C14—C2795.2 (3)C35—C36—C37—C322.0 (5)
C18—C13—C14—C27−84.6 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2215).

References

  • Bruker (1997). XSCANS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, J., Liu, J., Zhang, L. Y., Wu, G. Z., Hua, W. Y., Wu, X. M. & Sun, H. B. (2006). Bioorg. Med. Chem. Lett.16, 2915–2919. [PubMed]
  • Liu, J. (2005). J. Ethnopharmacol.100, 92-94. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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