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The title compound, 2α,3β-24-tri­hydroxy­olean-12-en-28-oic acid, C30H48O5, is a stereoisomer of hyptatic acid A (2α,3β-24-tri­hydroxy­olean-12-en-28-oic methano­late). The central ring, which is flattened due to the presence of a C=C double bond, adopts a sofa conformation. All other six-membered rings adopt distorted chair conformations. The crystal structure is stabilized by O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006451/ci6116sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006451/ci6116Isup2.hkl
Contains datablock I

CCDC reference: 189407

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.050
  • wR factor = 0.164
  • Data-to-parameter ratio = 9.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_420 Alert B D-H Without Acceptor O(2) - H(2O) ? General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 71.90 From the CIF: _reflns_number_total 2962 Count of symmetry unique reflns 2988 Completeness (_total/calc) 99.13% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: PARST97 (Nardelli, 1995) and PLATON (Spek, 2000).

2α,3β-24-trihydroxyolean-12-en-28-oic acid top
Crystal data top
C30H48O5Dx = 1.202 Mg m3
Mr = 488.68Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 11.580 (2) Åθ = 14–25°
b = 14.623 (2) ŵ = 0.63 mm1
c = 15.952 (4) ÅT = 293 K
V = 2701.2 (9) Å3Needle, colourless
Z = 40.22 × 0.13 × 0.10 mm
F(000) = 1072
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 71.9°, θmin = 4.1°
Graphite monochromatorh = 014
ω–2θ scansk = 017
2962 measured reflectionsl = 019
2962 independent reflections3 standard reflections every 120 min
1388 reflections with I > 2σ(I) intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.164 w = 1/[σ2(Fo2) + (0.0781P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
2962 reflectionsΔρmax = 0.23 e Å3
317 parametersΔρmin = 0.19 e Å3
9 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (4)
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
xyzUiso*/Ueq
O10.0538 (4)0.1668 (3)0.1689 (3)0.0534 (12)
H1O0.11480.19540.16960.080*
O20.0234 (4)0.0514 (3)0.2862 (2)0.0645 (14)
H2O0.03380.03320.31160.097*
O30.1564 (4)0.0952 (3)0.3095 (2)0.0684 (15)
H3O0.12360.04720.32140.103*
O40.1286 (4)0.3528 (3)0.3376 (3)0.0629 (14)
H4O0.19380.37260.32910.094*
O50.2193 (4)0.2209 (3)0.3343 (4)0.0727 (16)
C10.0799 (5)0.0476 (4)0.0637 (3)0.0385 (14)
H1A0.14430.07900.03760.046*
H1B0.00950.06990.03780.046*
C20.0776 (5)0.0711 (4)0.1564 (3)0.0396 (15)
H20.15180.05530.18210.048*
C30.0177 (6)0.0214 (4)0.2000 (3)0.0417 (15)
H30.09020.03950.17310.050*
C40.0097 (5)0.0833 (4)0.1947 (3)0.0390 (15)
C50.0024 (5)0.1072 (4)0.0989 (3)0.0352 (14)
H50.07610.08610.07570.042*
C60.0013 (6)0.2094 (4)0.0788 (3)0.0452 (16)
H6A0.07890.23260.08730.054*
H6B0.05040.24230.11590.054*
C70.0348 (6)0.2244 (4)0.0115 (3)0.0437 (16)
H7A0.11500.20630.01730.052*
H7B0.03030.28940.02360.052*
C80.0373 (5)0.1724 (4)0.0781 (4)0.0354 (14)
C90.0576 (5)0.0720 (4)0.0474 (3)0.0310 (13)
H90.01740.04190.05390.037*
C100.0910 (5)0.0564 (4)0.0464 (3)0.0351 (14)
C110.1374 (5)0.0229 (4)0.1098 (4)0.0430 (16)
H11A0.13170.04260.10090.052*
H11B0.21660.04090.09890.052*
C120.1084 (5)0.0439 (4)0.1992 (3)0.0379 (14)
H120.14340.00770.23980.046*
C130.0373 (5)0.1095 (4)0.2266 (3)0.0348 (14)
C140.0298 (5)0.1675 (4)0.1641 (3)0.0360 (14)
C150.0471 (6)0.2648 (4)0.2007 (3)0.0487 (17)
H15A0.02340.29930.19210.058*
H15B0.10780.29490.16920.058*
C160.0780 (5)0.2691 (4)0.2934 (4)0.0470 (17)
H16A0.15310.24120.30220.056*
H16B0.08270.33250.31100.056*
C170.0131 (5)0.2188 (4)0.3469 (4)0.0405 (15)
C180.0194 (5)0.1183 (4)0.3207 (3)0.0363 (14)
H180.08910.09350.34710.044*
C190.0818 (5)0.0623 (4)0.3548 (3)0.0451 (16)
H19A0.15210.08240.32740.054*
H19B0.06990.00140.34020.054*
C200.0980 (6)0.0694 (5)0.4497 (4)0.0457 (17)
C210.1131 (6)0.1702 (4)0.4723 (4)0.0529 (18)
H21A0.18440.19240.44780.063*
H21B0.11960.17580.53270.063*
C220.0141 (6)0.2293 (4)0.4421 (3)0.0470 (17)
H22A0.05460.21380.47390.056*
H22B0.03230.29280.45360.056*
C230.1273 (6)0.1209 (5)0.2258 (4)0.0518 (18)
H23A0.18760.09950.18840.062*
H23B0.12580.18720.22240.062*
C240.0856 (6)0.1231 (4)0.2502 (4)0.0573 (19)
H24A0.07310.10480.30730.086*
H24B0.15930.10090.23160.086*
H24C0.08430.18860.24660.086*
C250.2164 (5)0.0842 (4)0.0682 (4)0.0480 (17)
H25A0.23060.07240.12650.072*
H25B0.26920.04920.03480.072*
H25C0.22700.14810.05700.072*
C260.1540 (5)0.2230 (4)0.0890 (4)0.0552 (19)
H26A0.19350.22530.03620.083*
H26B0.20070.19090.12910.083*
H26C0.14000.28400.10860.083*
C270.1540 (5)0.1257 (4)0.1554 (4)0.0495 (18)
H27A0.19060.12440.20930.074*
H27B0.14840.06460.13370.074*
H27C0.19890.16250.11770.074*
C280.1311 (6)0.2621 (5)0.3372 (4)0.0425 (15)
C290.0029 (7)0.0267 (5)0.4960 (4)0.072 (2)
H29A0.07280.05830.48140.108*
H29B0.00960.03650.48060.108*
H29C0.00970.03140.55530.108*
C300.2087 (7)0.0182 (6)0.4742 (4)0.075 (3)
H30A0.21950.02200.53380.112*
H30B0.20210.04480.45800.112*
H30C0.27360.04530.44630.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.061 (3)0.045 (3)0.054 (3)0.013 (2)0.007 (2)0.016 (2)
O20.077 (3)0.082 (4)0.035 (2)0.019 (3)0.008 (2)0.012 (2)
O30.079 (3)0.088 (4)0.039 (3)0.038 (3)0.011 (2)0.008 (3)
O40.062 (3)0.039 (3)0.087 (4)0.006 (2)0.010 (3)0.002 (3)
O50.034 (2)0.054 (3)0.129 (5)0.004 (2)0.001 (3)0.011 (3)
C10.034 (3)0.044 (4)0.037 (3)0.007 (3)0.000 (3)0.001 (3)
C20.044 (3)0.040 (4)0.035 (3)0.004 (3)0.003 (3)0.006 (3)
C30.046 (4)0.054 (4)0.025 (3)0.013 (3)0.001 (3)0.003 (3)
C40.044 (4)0.042 (4)0.032 (3)0.007 (3)0.005 (3)0.002 (3)
C50.038 (3)0.039 (4)0.029 (3)0.000 (3)0.002 (3)0.007 (3)
C60.058 (4)0.036 (4)0.041 (3)0.005 (3)0.004 (3)0.009 (3)
C70.057 (4)0.037 (4)0.037 (3)0.006 (3)0.004 (3)0.003 (3)
C80.035 (3)0.036 (4)0.035 (3)0.002 (3)0.001 (3)0.004 (3)
C90.031 (3)0.029 (3)0.033 (3)0.000 (3)0.001 (3)0.003 (3)
C100.041 (3)0.036 (4)0.029 (3)0.002 (3)0.001 (2)0.008 (3)
C110.050 (4)0.040 (4)0.038 (3)0.009 (3)0.003 (3)0.002 (3)
C120.045 (3)0.040 (4)0.029 (3)0.004 (3)0.002 (3)0.005 (3)
C130.034 (3)0.039 (4)0.031 (3)0.006 (3)0.002 (3)0.000 (3)
C140.039 (3)0.036 (3)0.033 (3)0.002 (3)0.007 (3)0.003 (3)
C150.058 (4)0.043 (4)0.045 (4)0.013 (3)0.003 (3)0.006 (3)
C160.048 (4)0.048 (4)0.045 (4)0.012 (3)0.002 (3)0.013 (3)
C170.039 (3)0.041 (4)0.041 (3)0.003 (3)0.002 (3)0.005 (3)
C180.039 (3)0.035 (3)0.035 (3)0.002 (3)0.004 (3)0.005 (3)
C190.048 (4)0.049 (4)0.038 (3)0.009 (3)0.008 (3)0.005 (3)
C200.048 (4)0.050 (4)0.039 (4)0.004 (4)0.013 (3)0.001 (3)
C210.054 (4)0.062 (5)0.043 (4)0.003 (4)0.008 (3)0.013 (3)
C220.053 (4)0.057 (4)0.031 (3)0.007 (4)0.008 (3)0.011 (3)
C230.059 (4)0.060 (5)0.037 (3)0.013 (4)0.006 (3)0.001 (3)
C240.065 (5)0.063 (5)0.043 (4)0.006 (4)0.013 (4)0.012 (4)
C250.038 (3)0.057 (5)0.049 (4)0.002 (3)0.004 (3)0.002 (3)
C260.056 (4)0.051 (4)0.059 (4)0.013 (4)0.010 (4)0.009 (4)
C270.038 (3)0.069 (5)0.041 (3)0.002 (4)0.001 (3)0.009 (4)
C280.047 (4)0.046 (4)0.035 (3)0.008 (3)0.007 (3)0.010 (3)
C290.089 (6)0.082 (6)0.045 (4)0.012 (6)0.002 (4)0.001 (4)
C300.082 (6)0.091 (6)0.051 (4)0.034 (5)0.019 (4)0.006 (4)
Geometric parameters (Å, º) top
O1—C21.439 (7)C14—C271.569 (8)
O1—H1O0.82C15—C161.523 (8)
O2—C31.445 (6)C15—H15A0.97
O2—H2O0.82C15—H15B0.97
O3—C231.427 (7)C16—C171.542 (8)
O3—H3O0.82C16—H16A0.97
O4—C281.326 (7)C16—H16B0.97
O4—H4O0.82C17—C281.514 (8)
O5—C281.187 (7)C17—C181.529 (8)
C1—C21.518 (7)C17—C221.559 (7)
C1—C101.552 (8)C18—C191.529 (8)
C1—H1A0.97C18—H180.98
C1—H1B0.97C19—C201.529 (8)
C2—C31.494 (8)C19—H19A0.97
C2—H20.98C19—H19B0.97
C3—C41.536 (8)C20—C291.518 (9)
C3—H30.98C20—C211.527 (9)
C4—C241.530 (8)C20—C301.535 (9)
C4—C231.550 (8)C21—C221.514 (8)
C4—C51.570 (7)C21—H21A0.97
C5—C61.530 (7)C21—H21B0.97
C5—C101.557 (8)C22—H22A0.97
C5—H50.98C22—H22B0.97
C6—C71.516 (8)C23—H23A0.97
C6—H6A0.97C23—H23B0.97
C6—H6B0.97C24—H24A0.96
C7—C81.551 (8)C24—H24B0.96
C7—H7A0.97C24—H24C0.96
C7—H7B0.97C25—H25A0.96
C8—C261.551 (8)C25—H25B0.96
C8—C91.565 (8)C25—H25C0.96
C8—C141.578 (8)C26—H26A0.96
C9—C111.536 (7)C26—H26B0.96
C9—C101.562 (7)C26—H26C0.96
C9—H90.98C27—H27A0.96
C10—C251.547 (8)C27—H27B0.96
C11—C121.497 (7)C27—H27C0.96
C11—H11A0.97C29—H29A0.96
C11—H11B0.97C29—H29B0.96
C12—C131.338 (8)C29—H29C0.96
C12—H120.93C30—H30A0.96
C13—C181.521 (7)C30—H30B0.96
C13—C141.522 (8)C30—H30C0.96
C14—C151.551 (8)
C2—O1—H1O109.5C15—C16—C17110.9 (5)
C3—O2—H2O109.5C15—C16—H16A109.5
C23—O3—H3O109.5C17—C16—H16A109.5
C28—O4—H4O109.5C15—C16—H16B109.5
C2—C1—C10113.4 (5)C17—C16—H16B109.5
C2—C1—H1A108.9H16A—C16—H16B108.1
C10—C1—H1A108.9C28—C17—C18109.3 (5)
C2—C1—H1B108.9C28—C17—C16111.2 (5)
C10—C1—H1B108.9C18—C17—C16109.9 (5)
H1A—C1—H1B107.7C28—C17—C22103.9 (5)
O1—C2—C3105.5 (5)C18—C17—C22111.7 (5)
O1—C2—C1111.0 (5)C16—C17—C22110.8 (5)
C3—C2—C1110.9 (5)C13—C18—C17110.9 (5)
O1—C2—H2109.8C13—C18—C19114.2 (5)
C3—C2—H2109.8C17—C18—C19112.5 (5)
C1—C2—H2109.8C13—C18—H18106.2
O2—C3—C2109.2 (5)C17—C18—H18106.2
O2—C3—C4111.0 (5)C19—C18—H18106.2
C2—C3—C4114.6 (5)C20—C19—C18114.1 (5)
O2—C3—H3107.3C20—C19—H19A108.7
C2—C3—H3107.3C18—C19—H19A108.7
C4—C3—H3107.3C20—C19—H19B108.7
C24—C4—C3113.0 (5)C18—C19—H19B108.7
C24—C4—C23108.3 (5)H19A—C19—H19B107.6
C3—C4—C23106.5 (5)C29—C20—C21111.7 (6)
C24—C4—C5116.1 (5)C29—C20—C19111.1 (5)
C3—C4—C5106.2 (4)C21—C20—C19108.3 (5)
C23—C4—C5106.2 (5)C29—C20—C30108.5 (6)
C6—C5—C10109.4 (5)C21—C20—C30108.4 (6)
C6—C5—C4115.0 (4)C19—C20—C30108.8 (6)
C10—C5—C4117.1 (5)C22—C21—C20112.9 (5)
C6—C5—H5104.6C22—C21—H21A109.0
C10—C5—H5104.6C20—C21—H21A109.0
C4—C5—H5104.6C22—C21—H21B109.0
C7—C6—C5109.5 (4)C20—C21—H21B109.0
C7—C6—H6A109.8H21A—C21—H21B107.8
C5—C6—H6A109.8C21—C22—C17114.0 (5)
C7—C6—H6B109.8C21—C22—H22A108.8
C5—C6—H6B109.8C17—C22—H22A108.8
H6A—C6—H6B108.2C21—C22—H22B108.8
C6—C7—C8115.5 (5)C17—C22—H22B108.8
C6—C7—H7A108.4H22A—C22—H22B107.7
C8—C7—H7A108.4O3—C23—C4114.3 (5)
C6—C7—H7B108.4O3—C23—H23A108.7
C8—C7—H7B108.4C4—C23—H23A108.7
H7A—C7—H7B107.5O3—C23—H23B108.7
C7—C8—C26108.2 (5)C4—C23—H23B108.7
C7—C8—C9109.1 (5)H23A—C23—H23B107.6
C26—C8—C9110.6 (5)C4—C24—H24A109.5
C7—C8—C14110.7 (4)C4—C24—H24B109.5
C26—C8—C14110.6 (5)H24A—C24—H24B109.5
C9—C8—C14107.7 (4)C4—C24—H24C109.5
C11—C9—C10113.8 (4)H24A—C24—H24C109.5
C11—C9—C8109.1 (4)H24B—C24—H24C109.5
C10—C9—C8118.2 (5)C10—C25—H25A109.5
C11—C9—H9104.8C10—C25—H25B109.5
C10—C9—H9104.8H25A—C25—H25B109.5
C8—C9—H9104.8C10—C25—H25C109.5
C25—C10—C1107.1 (5)H25A—C25—H25C109.5
C25—C10—C5113.9 (4)H25B—C25—H25C109.5
C1—C10—C5108.3 (5)C8—C26—H26A109.5
C25—C10—C9114.2 (5)C8—C26—H26B109.5
C1—C10—C9107.0 (4)H26A—C26—H26B109.5
C5—C10—C9105.9 (4)C8—C26—H26C109.5
C12—C11—C9112.7 (5)H26A—C26—H26C109.5
C12—C11—H11A109.0H26B—C26—H26C109.5
C9—C11—H11A109.0C14—C27—H27A109.5
C12—C11—H11B109.0C14—C27—H27B109.5
C9—C11—H11B109.0H27A—C27—H27B109.5
H11A—C11—H11B107.8C14—C27—H27C109.5
C13—C12—C11126.6 (5)H27A—C27—H27C109.5
C13—C12—H12116.7H27B—C27—H27C109.5
C11—C12—H12116.7O5—C28—O4121.8 (6)
C12—C13—C18117.9 (5)O5—C28—C17124.7 (6)
C12—C13—C14119.9 (5)O4—C28—C17113.4 (6)
C18—C13—C14122.0 (5)C20—C29—H29A109.5
C13—C14—C15109.2 (5)C20—C29—H29B109.5
C13—C14—C27108.0 (5)H29A—C29—H29B109.5
C15—C14—C27105.8 (5)C20—C29—H29C109.5
C13—C14—C8110.1 (4)H29A—C29—H29C109.5
C15—C14—C8110.5 (5)H29B—C29—H29C109.5
C27—C14—C8113.1 (4)C20—C30—H30A109.5
C16—C15—C14115.7 (5)C20—C30—H30B109.5
C16—C15—H15A108.3H30A—C30—H30B109.5
C14—C15—H15A108.3C20—C30—H30C109.5
C16—C15—H15B108.3H30A—C30—H30C109.5
C14—C15—H15B108.3H30B—C30—H30C109.5
H15A—C15—H15B107.4
C10—C1—C2—O1173.4 (5)C12—C13—C14—C2797.1 (6)
C10—C1—C2—C356.4 (7)C18—C13—C14—C2778.0 (6)
O1—C2—C3—O254.8 (6)C12—C13—C14—C826.8 (7)
C1—C2—C3—O2175.1 (5)C18—C13—C14—C8158.1 (5)
O1—C2—C3—C4180.0 (5)C7—C8—C14—C13175.3 (5)
C1—C2—C3—C459.7 (7)C26—C8—C14—C1364.8 (6)
O2—C3—C4—C2450.9 (7)C9—C8—C14—C1356.1 (6)
C2—C3—C4—C2473.3 (6)C7—C8—C14—C1563.9 (6)
O2—C3—C4—C2367.8 (6)C26—C8—C14—C1556.0 (6)
C2—C3—C4—C23167.9 (5)C9—C8—C14—C15176.9 (5)
O2—C3—C4—C5179.3 (4)C7—C8—C14—C2754.4 (6)
C2—C3—C4—C555.0 (7)C26—C8—C14—C27174.3 (5)
C24—C4—C5—C655.9 (7)C9—C8—C14—C2764.8 (6)
C3—C4—C5—C6177.6 (5)C13—C14—C15—C1641.5 (7)
C23—C4—C5—C664.6 (7)C27—C14—C15—C1674.5 (6)
C24—C4—C5—C1074.8 (7)C8—C14—C15—C16162.8 (5)
C3—C4—C5—C1051.7 (7)C14—C15—C16—C1755.9 (7)
C23—C4—C5—C10164.7 (5)C15—C16—C17—C2860.9 (7)
C10—C5—C6—C766.0 (6)C15—C16—C17—C1860.2 (7)
C4—C5—C6—C7159.7 (5)C15—C16—C17—C22176.0 (5)
C5—C6—C7—C856.9 (7)C12—C13—C18—C17140.9 (5)
C6—C7—C8—C2676.6 (6)C14—C13—C18—C1743.9 (7)
C6—C7—C8—C943.8 (6)C12—C13—C18—C1990.8 (6)
C6—C7—C8—C14162.1 (5)C14—C13—C18—C1984.3 (7)
C7—C8—C9—C11175.3 (5)C28—C17—C18—C1369.7 (6)
C26—C8—C9—C1156.4 (6)C16—C17—C18—C1352.6 (7)
C14—C8—C9—C1164.5 (5)C22—C17—C18—C13175.9 (5)
C7—C8—C9—C1043.2 (6)C28—C17—C18—C19161.1 (5)
C26—C8—C9—C1075.6 (6)C16—C17—C18—C1976.6 (6)
C14—C8—C9—C10163.4 (4)C22—C17—C18—C1946.7 (7)
C2—C1—C10—C2572.7 (6)C13—C18—C19—C20178.7 (5)
C2—C1—C10—C550.6 (6)C17—C18—C19—C2053.8 (7)
C2—C1—C10—C9164.4 (5)C18—C19—C20—C2966.2 (7)
C6—C5—C10—C2564.6 (6)C18—C19—C20—C2156.8 (7)
C4—C5—C10—C2568.7 (7)C18—C19—C20—C30174.4 (6)
C6—C5—C10—C1176.4 (5)C29—C20—C21—C2266.7 (7)
C4—C5—C10—C150.4 (6)C19—C20—C21—C2255.9 (7)
C6—C5—C10—C961.8 (6)C30—C20—C21—C22173.7 (5)
C4—C5—C10—C9164.9 (5)C20—C21—C22—C1753.1 (7)
C11—C9—C10—C2556.4 (7)C28—C17—C22—C21165.0 (5)
C8—C9—C10—C2573.5 (6)C18—C17—C22—C2147.3 (7)
C11—C9—C10—C162.0 (6)C16—C17—C22—C2175.5 (7)
C8—C9—C10—C1168.1 (5)C24—C4—C23—O362.5 (7)
C11—C9—C10—C5177.3 (5)C3—C4—C23—O359.3 (7)
C8—C9—C10—C552.7 (6)C5—C4—C23—O3172.2 (5)
C10—C9—C11—C12176.2 (5)C18—C17—C28—O520.4 (8)
C8—C9—C11—C1241.8 (7)C16—C17—C28—O5141.9 (7)
C9—C11—C12—C1311.9 (9)C22—C17—C28—O598.9 (7)
C11—C12—C13—C18179.5 (6)C18—C17—C28—O4163.8 (5)
C11—C12—C13—C144.2 (9)C16—C17—C28—O442.4 (7)
C12—C13—C14—C15148.3 (5)C22—C17—C28—O476.8 (6)
C18—C13—C14—C1536.6 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O5i0.821.962.744 (6)160
O3—H3O···O20.821.932.665 (6)148
O4—H4O···O3ii0.821.822.642 (7)174
Symmetry codes: (i) x+1/2, y, z1/2; (ii) x+1/2, y+1/2, z.
Table 2. Comparison of the unusually large bond lengths (Å) and angles (°) in the skleton of Arjunolic Acid with those found in the average skeleton of related structures top
BondArjunolic AcidAverage
C4-C51.570 (7)1.563 (9)
C5-C101.557 (8)1.552 (8)
C9-C101.562 (7)1.570 (10)
C7-C81.551 (8)1.541 (8)
C8-C91.565 (8)1.553 (8)
C8-C141.578 (8)1.589 (6)
C17-C221.559 (7)1.546 (13)
C2-C3-C4114.6 (5)114.2 (12)
C1-C2-C3110.9 (5)111.0 (12)
C10-C1-C2113.4 (5)113.5 (11)
C4-C5-C10117.1 (5)117.0 (9)
C4-C5-C6115.0 (4)114.4 (5)
C6-C7-C8115.5 (5)114.1 (7)
C7-C8-C14110.7 (4)110.5 (5)
C8-C9-C10118.2 (5)117.5 (8)
C10-C9-C11113.8 (4)113.2 (6)
C14-C15-C16115.7 (5)114.6 (5)
C15-C16-C17110.9 (5)112.4 (7)
C16-C17-C18109.9 (5)108.7 (11)
C16-C17-C22110.8 (5)112.0 (13)
C18-C17-C22111.7 (5)110.2 (12)
C17-C18-C13110.9 (5)112.3 (9)
C17-C18-C19112.5 (5)112.8 (10)
C13-C18-C19114.2 (5)111.9 (15)
C18-C19-C20114.1 (5)113.7 (20)
C20-C21-C22112.9 (5)112.8 (14)
C21-C22-C17114.0 (5)114.4 (10)
 

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