Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, 2α,3β-24-trihydroxyolean-12-en-28-oic acid, C
30H
48O
5, 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
CCDC reference: 189407
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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).
2
α,3
β-24-trihydroxyolean-12-en-28-oic acid
top
Crystal data top
C30H48O5 | Dx = 1.202 Mg m−3 |
Mr = 488.68 | Cu Kα radiation, λ = 1.5418 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 11.580 (2) Å | θ = 14–25° |
b = 14.623 (2) Å | µ = 0.63 mm−1 |
c = 15.952 (4) Å | T = 293 K |
V = 2701.2 (9) Å3 | Needle, colourless |
Z = 4 | 0.22 × 0.13 × 0.10 mm |
F(000) = 1072 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 71.9°, θmin = 4.1° |
Graphite monochromator | h = 0→14 |
ω–2θ scans | k = 0→17 |
2962 measured reflections | l = 0→19 |
2962 independent reflections | 3 standard reflections every 120 min |
1388 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-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 reflections | Δρmax = 0.23 e Å−3 |
317 parameters | Δρmin = −0.19 e Å−3 |
9 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.0538 (4) | −0.1668 (3) | −0.1689 (3) | 0.0534 (12) | |
H1O | 0.1148 | −0.1954 | −0.1696 | 0.080* | |
O2 | −0.0234 (4) | −0.0514 (3) | −0.2862 (2) | 0.0645 (14) | |
H2O | 0.0338 | −0.0332 | −0.3116 | 0.097* | |
O3 | −0.1564 (4) | 0.0952 (3) | −0.3095 (2) | 0.0684 (15) | |
H3O | −0.1236 | 0.0472 | −0.3214 | 0.103* | |
O4 | 0.1286 (4) | 0.3528 (3) | 0.3376 (3) | 0.0629 (14) | |
H4O | 0.1938 | 0.3726 | 0.3291 | 0.094* | |
O5 | 0.2193 (4) | 0.2209 (3) | 0.3343 (4) | 0.0727 (16) | |
C1 | 0.0799 (5) | −0.0476 (4) | −0.0637 (3) | 0.0385 (14) | |
H1A | 0.1443 | −0.0790 | −0.0376 | 0.046* | |
H1B | 0.0095 | −0.0699 | −0.0378 | 0.046* | |
C2 | 0.0776 (5) | −0.0711 (4) | −0.1564 (3) | 0.0396 (15) | |
H2 | 0.1518 | −0.0553 | −0.1821 | 0.048* | |
C3 | −0.0177 (6) | −0.0214 (4) | −0.2000 (3) | 0.0417 (15) | |
H3 | −0.0902 | −0.0395 | −0.1731 | 0.050* | |
C4 | −0.0097 (5) | 0.0833 (4) | −0.1947 (3) | 0.0390 (15) | |
C5 | −0.0024 (5) | 0.1072 (4) | −0.0989 (3) | 0.0352 (14) | |
H5 | −0.0761 | 0.0861 | −0.0757 | 0.042* | |
C6 | 0.0013 (6) | 0.2094 (4) | −0.0788 (3) | 0.0452 (16) | |
H6A | 0.0789 | 0.2326 | −0.0873 | 0.054* | |
H6B | −0.0504 | 0.2423 | −0.1159 | 0.054* | |
C7 | −0.0348 (6) | 0.2244 (4) | 0.0115 (3) | 0.0437 (16) | |
H7A | −0.1150 | 0.2063 | 0.0173 | 0.052* | |
H7B | −0.0303 | 0.2894 | 0.0236 | 0.052* | |
C8 | 0.0373 (5) | 0.1724 (4) | 0.0781 (4) | 0.0354 (14) | |
C9 | 0.0576 (5) | 0.0720 (4) | 0.0474 (3) | 0.0310 (13) | |
H9 | −0.0174 | 0.0419 | 0.0539 | 0.037* | |
C10 | 0.0910 (5) | 0.0564 (4) | −0.0464 (3) | 0.0351 (14) | |
C11 | 0.1374 (5) | 0.0229 (4) | 0.1098 (4) | 0.0430 (16) | |
H11A | 0.1317 | −0.0426 | 0.1009 | 0.052* | |
H11B | 0.2166 | 0.0409 | 0.0989 | 0.052* | |
C12 | 0.1084 (5) | 0.0439 (4) | 0.1992 (3) | 0.0379 (14) | |
H12 | 0.1434 | 0.0077 | 0.2398 | 0.046* | |
C13 | 0.0373 (5) | 0.1095 (4) | 0.2266 (3) | 0.0348 (14) | |
C14 | −0.0298 (5) | 0.1675 (4) | 0.1641 (3) | 0.0360 (14) | |
C15 | −0.0471 (6) | 0.2648 (4) | 0.2007 (3) | 0.0487 (17) | |
H15A | 0.0234 | 0.2993 | 0.1921 | 0.058* | |
H15B | −0.1078 | 0.2949 | 0.1692 | 0.058* | |
C16 | −0.0780 (5) | 0.2691 (4) | 0.2934 (4) | 0.0470 (17) | |
H16A | −0.1531 | 0.2412 | 0.3022 | 0.056* | |
H16B | −0.0827 | 0.3325 | 0.3110 | 0.056* | |
C17 | 0.0131 (5) | 0.2188 (4) | 0.3469 (4) | 0.0405 (15) | |
C18 | 0.0194 (5) | 0.1183 (4) | 0.3207 (3) | 0.0363 (14) | |
H18 | 0.0891 | 0.0935 | 0.3471 | 0.044* | |
C19 | −0.0818 (5) | 0.0623 (4) | 0.3548 (3) | 0.0451 (16) | |
H19A | −0.1521 | 0.0824 | 0.3274 | 0.054* | |
H19B | −0.0699 | −0.0014 | 0.3402 | 0.054* | |
C20 | −0.0980 (6) | 0.0694 (5) | 0.4497 (4) | 0.0457 (17) | |
C21 | −0.1131 (6) | 0.1702 (4) | 0.4723 (4) | 0.0529 (18) | |
H21A | −0.1844 | 0.1924 | 0.4478 | 0.063* | |
H21B | −0.1196 | 0.1758 | 0.5327 | 0.063* | |
C22 | −0.0141 (6) | 0.2293 (4) | 0.4421 (3) | 0.0470 (17) | |
H22A | 0.0546 | 0.2138 | 0.4739 | 0.056* | |
H22B | −0.0323 | 0.2928 | 0.4536 | 0.056* | |
C23 | −0.1273 (6) | 0.1209 (5) | −0.2258 (4) | 0.0518 (18) | |
H23A | −0.1876 | 0.0995 | −0.1884 | 0.062* | |
H23B | −0.1258 | 0.1872 | −0.2224 | 0.062* | |
C24 | 0.0856 (6) | 0.1231 (4) | −0.2502 (4) | 0.0573 (19) | |
H24A | 0.0731 | 0.1048 | −0.3073 | 0.086* | |
H24B | 0.1593 | 0.1009 | −0.2316 | 0.086* | |
H24C | 0.0843 | 0.1886 | −0.2466 | 0.086* | |
C25 | 0.2164 (5) | 0.0842 (4) | −0.0682 (4) | 0.0480 (17) | |
H25A | 0.2306 | 0.0724 | −0.1265 | 0.072* | |
H25B | 0.2692 | 0.0492 | −0.0348 | 0.072* | |
H25C | 0.2270 | 0.1481 | −0.0570 | 0.072* | |
C26 | 0.1540 (5) | 0.2230 (4) | 0.0890 (4) | 0.0552 (19) | |
H26A | 0.1935 | 0.2253 | 0.0362 | 0.083* | |
H26B | 0.2007 | 0.1909 | 0.1291 | 0.083* | |
H26C | 0.1400 | 0.2840 | 0.1086 | 0.083* | |
C27 | −0.1540 (5) | 0.1257 (4) | 0.1554 (4) | 0.0495 (18) | |
H27A | −0.1906 | 0.1244 | 0.2093 | 0.074* | |
H27B | −0.1484 | 0.0646 | 0.1337 | 0.074* | |
H27C | −0.1989 | 0.1625 | 0.1177 | 0.074* | |
C28 | 0.1311 (6) | 0.2621 (5) | 0.3372 (4) | 0.0425 (15) | |
C29 | 0.0029 (7) | 0.0267 (5) | 0.4960 (4) | 0.072 (2) | |
H29A | 0.0728 | 0.0583 | 0.4814 | 0.108* | |
H29B | 0.0096 | −0.0365 | 0.4806 | 0.108* | |
H29C | −0.0097 | 0.0314 | 0.5553 | 0.108* | |
C30 | −0.2087 (7) | 0.0182 (6) | 0.4742 (4) | 0.075 (3) | |
H30A | −0.2195 | 0.0220 | 0.5338 | 0.112* | |
H30B | −0.2021 | −0.0448 | 0.4580 | 0.112* | |
H30C | −0.2736 | 0.0453 | 0.4463 | 0.112* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.061 (3) | 0.045 (3) | 0.054 (3) | 0.013 (2) | −0.007 (2) | −0.016 (2) |
O2 | 0.077 (3) | 0.082 (4) | 0.035 (2) | 0.019 (3) | −0.008 (2) | −0.012 (2) |
O3 | 0.079 (3) | 0.088 (4) | 0.039 (3) | 0.038 (3) | −0.011 (2) | −0.008 (3) |
O4 | 0.062 (3) | 0.039 (3) | 0.087 (4) | −0.006 (2) | 0.010 (3) | −0.002 (3) |
O5 | 0.034 (2) | 0.054 (3) | 0.129 (5) | 0.004 (2) | 0.001 (3) | −0.011 (3) |
C1 | 0.034 (3) | 0.044 (4) | 0.037 (3) | 0.007 (3) | 0.000 (3) | −0.001 (3) |
C2 | 0.044 (3) | 0.040 (4) | 0.035 (3) | 0.004 (3) | 0.003 (3) | −0.006 (3) |
C3 | 0.046 (4) | 0.054 (4) | 0.025 (3) | 0.013 (3) | 0.001 (3) | −0.003 (3) |
C4 | 0.044 (4) | 0.042 (4) | 0.032 (3) | 0.007 (3) | 0.005 (3) | −0.002 (3) |
C5 | 0.038 (3) | 0.039 (4) | 0.029 (3) | 0.000 (3) | 0.002 (3) | 0.007 (3) |
C6 | 0.058 (4) | 0.036 (4) | 0.041 (3) | 0.005 (3) | −0.004 (3) | 0.009 (3) |
C7 | 0.057 (4) | 0.037 (4) | 0.037 (3) | 0.006 (3) | −0.004 (3) | 0.003 (3) |
C8 | 0.035 (3) | 0.036 (4) | 0.035 (3) | 0.002 (3) | 0.001 (3) | −0.004 (3) |
C9 | 0.031 (3) | 0.029 (3) | 0.033 (3) | 0.000 (3) | 0.001 (3) | −0.003 (3) |
C10 | 0.041 (3) | 0.036 (4) | 0.029 (3) | −0.002 (3) | 0.001 (2) | 0.008 (3) |
C11 | 0.050 (4) | 0.040 (4) | 0.038 (3) | 0.009 (3) | −0.003 (3) | 0.002 (3) |
C12 | 0.045 (3) | 0.040 (4) | 0.029 (3) | 0.004 (3) | −0.002 (3) | 0.005 (3) |
C13 | 0.034 (3) | 0.039 (4) | 0.031 (3) | −0.006 (3) | −0.002 (3) | 0.000 (3) |
C14 | 0.039 (3) | 0.036 (3) | 0.033 (3) | 0.002 (3) | −0.007 (3) | −0.003 (3) |
C15 | 0.058 (4) | 0.043 (4) | 0.045 (4) | 0.013 (3) | −0.003 (3) | −0.006 (3) |
C16 | 0.048 (4) | 0.048 (4) | 0.045 (4) | 0.012 (3) | −0.002 (3) | −0.013 (3) |
C17 | 0.039 (3) | 0.041 (4) | 0.041 (3) | 0.003 (3) | −0.002 (3) | −0.005 (3) |
C18 | 0.039 (3) | 0.035 (3) | 0.035 (3) | 0.002 (3) | −0.004 (3) | −0.005 (3) |
C19 | 0.048 (4) | 0.049 (4) | 0.038 (3) | −0.009 (3) | 0.008 (3) | −0.005 (3) |
C20 | 0.048 (4) | 0.050 (4) | 0.039 (4) | −0.004 (4) | 0.013 (3) | −0.001 (3) |
C21 | 0.054 (4) | 0.062 (5) | 0.043 (4) | 0.003 (4) | 0.008 (3) | −0.013 (3) |
C22 | 0.053 (4) | 0.057 (4) | 0.031 (3) | −0.007 (4) | 0.008 (3) | −0.011 (3) |
C23 | 0.059 (4) | 0.060 (5) | 0.037 (3) | 0.013 (4) | −0.006 (3) | 0.001 (3) |
C24 | 0.065 (5) | 0.063 (5) | 0.043 (4) | −0.006 (4) | 0.013 (4) | 0.012 (4) |
C25 | 0.038 (3) | 0.057 (5) | 0.049 (4) | 0.002 (3) | 0.004 (3) | −0.002 (3) |
C26 | 0.056 (4) | 0.051 (4) | 0.059 (4) | −0.013 (4) | 0.010 (4) | −0.009 (4) |
C27 | 0.038 (3) | 0.069 (5) | 0.041 (3) | −0.002 (4) | 0.001 (3) | −0.009 (4) |
C28 | 0.047 (4) | 0.046 (4) | 0.035 (3) | −0.008 (3) | −0.007 (3) | −0.010 (3) |
C29 | 0.089 (6) | 0.082 (6) | 0.045 (4) | 0.012 (6) | 0.002 (4) | 0.001 (4) |
C30 | 0.082 (6) | 0.091 (6) | 0.051 (4) | −0.034 (5) | 0.019 (4) | −0.006 (4) |
Geometric parameters (Å, º) top
O1—C2 | 1.439 (7) | C14—C27 | 1.569 (8) |
O1—H1O | 0.82 | C15—C16 | 1.523 (8) |
O2—C3 | 1.445 (6) | C15—H15A | 0.97 |
O2—H2O | 0.82 | C15—H15B | 0.97 |
O3—C23 | 1.427 (7) | C16—C17 | 1.542 (8) |
O3—H3O | 0.82 | C16—H16A | 0.97 |
O4—C28 | 1.326 (7) | C16—H16B | 0.97 |
O4—H4O | 0.82 | C17—C28 | 1.514 (8) |
O5—C28 | 1.187 (7) | C17—C18 | 1.529 (8) |
C1—C2 | 1.518 (7) | C17—C22 | 1.559 (7) |
C1—C10 | 1.552 (8) | C18—C19 | 1.529 (8) |
C1—H1A | 0.97 | C18—H18 | 0.98 |
C1—H1B | 0.97 | C19—C20 | 1.529 (8) |
C2—C3 | 1.494 (8) | C19—H19A | 0.97 |
C2—H2 | 0.98 | C19—H19B | 0.97 |
C3—C4 | 1.536 (8) | C20—C29 | 1.518 (9) |
C3—H3 | 0.98 | C20—C21 | 1.527 (9) |
C4—C24 | 1.530 (8) | C20—C30 | 1.535 (9) |
C4—C23 | 1.550 (8) | C21—C22 | 1.514 (8) |
C4—C5 | 1.570 (7) | C21—H21A | 0.97 |
C5—C6 | 1.530 (7) | C21—H21B | 0.97 |
C5—C10 | 1.557 (8) | C22—H22A | 0.97 |
C5—H5 | 0.98 | C22—H22B | 0.97 |
C6—C7 | 1.516 (8) | C23—H23A | 0.97 |
C6—H6A | 0.97 | C23—H23B | 0.97 |
C6—H6B | 0.97 | C24—H24A | 0.96 |
C7—C8 | 1.551 (8) | C24—H24B | 0.96 |
C7—H7A | 0.97 | C24—H24C | 0.96 |
C7—H7B | 0.97 | C25—H25A | 0.96 |
C8—C26 | 1.551 (8) | C25—H25B | 0.96 |
C8—C9 | 1.565 (8) | C25—H25C | 0.96 |
C8—C14 | 1.578 (8) | C26—H26A | 0.96 |
C9—C11 | 1.536 (7) | C26—H26B | 0.96 |
C9—C10 | 1.562 (7) | C26—H26C | 0.96 |
C9—H9 | 0.98 | C27—H27A | 0.96 |
C10—C25 | 1.547 (8) | C27—H27B | 0.96 |
C11—C12 | 1.497 (7) | C27—H27C | 0.96 |
C11—H11A | 0.97 | C29—H29A | 0.96 |
C11—H11B | 0.97 | C29—H29B | 0.96 |
C12—C13 | 1.338 (8) | C29—H29C | 0.96 |
C12—H12 | 0.93 | C30—H30A | 0.96 |
C13—C18 | 1.521 (7) | C30—H30B | 0.96 |
C13—C14 | 1.522 (8) | C30—H30C | 0.96 |
C14—C15 | 1.551 (8) | | |
| | | |
C2—O1—H1O | 109.5 | C15—C16—C17 | 110.9 (5) |
C3—O2—H2O | 109.5 | C15—C16—H16A | 109.5 |
C23—O3—H3O | 109.5 | C17—C16—H16A | 109.5 |
C28—O4—H4O | 109.5 | C15—C16—H16B | 109.5 |
C2—C1—C10 | 113.4 (5) | C17—C16—H16B | 109.5 |
C2—C1—H1A | 108.9 | H16A—C16—H16B | 108.1 |
C10—C1—H1A | 108.9 | C28—C17—C18 | 109.3 (5) |
C2—C1—H1B | 108.9 | C28—C17—C16 | 111.2 (5) |
C10—C1—H1B | 108.9 | C18—C17—C16 | 109.9 (5) |
H1A—C1—H1B | 107.7 | C28—C17—C22 | 103.9 (5) |
O1—C2—C3 | 105.5 (5) | C18—C17—C22 | 111.7 (5) |
O1—C2—C1 | 111.0 (5) | C16—C17—C22 | 110.8 (5) |
C3—C2—C1 | 110.9 (5) | C13—C18—C17 | 110.9 (5) |
O1—C2—H2 | 109.8 | C13—C18—C19 | 114.2 (5) |
C3—C2—H2 | 109.8 | C17—C18—C19 | 112.5 (5) |
C1—C2—H2 | 109.8 | C13—C18—H18 | 106.2 |
O2—C3—C2 | 109.2 (5) | C17—C18—H18 | 106.2 |
O2—C3—C4 | 111.0 (5) | C19—C18—H18 | 106.2 |
C2—C3—C4 | 114.6 (5) | C20—C19—C18 | 114.1 (5) |
O2—C3—H3 | 107.3 | C20—C19—H19A | 108.7 |
C2—C3—H3 | 107.3 | C18—C19—H19A | 108.7 |
C4—C3—H3 | 107.3 | C20—C19—H19B | 108.7 |
C24—C4—C3 | 113.0 (5) | C18—C19—H19B | 108.7 |
C24—C4—C23 | 108.3 (5) | H19A—C19—H19B | 107.6 |
C3—C4—C23 | 106.5 (5) | C29—C20—C21 | 111.7 (6) |
C24—C4—C5 | 116.1 (5) | C29—C20—C19 | 111.1 (5) |
C3—C4—C5 | 106.2 (4) | C21—C20—C19 | 108.3 (5) |
C23—C4—C5 | 106.2 (5) | C29—C20—C30 | 108.5 (6) |
C6—C5—C10 | 109.4 (5) | C21—C20—C30 | 108.4 (6) |
C6—C5—C4 | 115.0 (4) | C19—C20—C30 | 108.8 (6) |
C10—C5—C4 | 117.1 (5) | C22—C21—C20 | 112.9 (5) |
C6—C5—H5 | 104.6 | C22—C21—H21A | 109.0 |
C10—C5—H5 | 104.6 | C20—C21—H21A | 109.0 |
C4—C5—H5 | 104.6 | C22—C21—H21B | 109.0 |
C7—C6—C5 | 109.5 (4) | C20—C21—H21B | 109.0 |
C7—C6—H6A | 109.8 | H21A—C21—H21B | 107.8 |
C5—C6—H6A | 109.8 | C21—C22—C17 | 114.0 (5) |
C7—C6—H6B | 109.8 | C21—C22—H22A | 108.8 |
C5—C6—H6B | 109.8 | C17—C22—H22A | 108.8 |
H6A—C6—H6B | 108.2 | C21—C22—H22B | 108.8 |
C6—C7—C8 | 115.5 (5) | C17—C22—H22B | 108.8 |
C6—C7—H7A | 108.4 | H22A—C22—H22B | 107.7 |
C8—C7—H7A | 108.4 | O3—C23—C4 | 114.3 (5) |
C6—C7—H7B | 108.4 | O3—C23—H23A | 108.7 |
C8—C7—H7B | 108.4 | C4—C23—H23A | 108.7 |
H7A—C7—H7B | 107.5 | O3—C23—H23B | 108.7 |
C7—C8—C26 | 108.2 (5) | C4—C23—H23B | 108.7 |
C7—C8—C9 | 109.1 (5) | H23A—C23—H23B | 107.6 |
C26—C8—C9 | 110.6 (5) | C4—C24—H24A | 109.5 |
C7—C8—C14 | 110.7 (4) | C4—C24—H24B | 109.5 |
C26—C8—C14 | 110.6 (5) | H24A—C24—H24B | 109.5 |
C9—C8—C14 | 107.7 (4) | C4—C24—H24C | 109.5 |
C11—C9—C10 | 113.8 (4) | H24A—C24—H24C | 109.5 |
C11—C9—C8 | 109.1 (4) | H24B—C24—H24C | 109.5 |
C10—C9—C8 | 118.2 (5) | C10—C25—H25A | 109.5 |
C11—C9—H9 | 104.8 | C10—C25—H25B | 109.5 |
C10—C9—H9 | 104.8 | H25A—C25—H25B | 109.5 |
C8—C9—H9 | 104.8 | C10—C25—H25C | 109.5 |
C25—C10—C1 | 107.1 (5) | H25A—C25—H25C | 109.5 |
C25—C10—C5 | 113.9 (4) | H25B—C25—H25C | 109.5 |
C1—C10—C5 | 108.3 (5) | C8—C26—H26A | 109.5 |
C25—C10—C9 | 114.2 (5) | C8—C26—H26B | 109.5 |
C1—C10—C9 | 107.0 (4) | H26A—C26—H26B | 109.5 |
C5—C10—C9 | 105.9 (4) | C8—C26—H26C | 109.5 |
C12—C11—C9 | 112.7 (5) | H26A—C26—H26C | 109.5 |
C12—C11—H11A | 109.0 | H26B—C26—H26C | 109.5 |
C9—C11—H11A | 109.0 | C14—C27—H27A | 109.5 |
C12—C11—H11B | 109.0 | C14—C27—H27B | 109.5 |
C9—C11—H11B | 109.0 | H27A—C27—H27B | 109.5 |
H11A—C11—H11B | 107.8 | C14—C27—H27C | 109.5 |
C13—C12—C11 | 126.6 (5) | H27A—C27—H27C | 109.5 |
C13—C12—H12 | 116.7 | H27B—C27—H27C | 109.5 |
C11—C12—H12 | 116.7 | O5—C28—O4 | 121.8 (6) |
C12—C13—C18 | 117.9 (5) | O5—C28—C17 | 124.7 (6) |
C12—C13—C14 | 119.9 (5) | O4—C28—C17 | 113.4 (6) |
C18—C13—C14 | 122.0 (5) | C20—C29—H29A | 109.5 |
C13—C14—C15 | 109.2 (5) | C20—C29—H29B | 109.5 |
C13—C14—C27 | 108.0 (5) | H29A—C29—H29B | 109.5 |
C15—C14—C27 | 105.8 (5) | C20—C29—H29C | 109.5 |
C13—C14—C8 | 110.1 (4) | H29A—C29—H29C | 109.5 |
C15—C14—C8 | 110.5 (5) | H29B—C29—H29C | 109.5 |
C27—C14—C8 | 113.1 (4) | C20—C30—H30A | 109.5 |
C16—C15—C14 | 115.7 (5) | C20—C30—H30B | 109.5 |
C16—C15—H15A | 108.3 | H30A—C30—H30B | 109.5 |
C14—C15—H15A | 108.3 | C20—C30—H30C | 109.5 |
C16—C15—H15B | 108.3 | H30A—C30—H30C | 109.5 |
C14—C15—H15B | 108.3 | H30B—C30—H30C | 109.5 |
H15A—C15—H15B | 107.4 | | |
| | | |
C10—C1—C2—O1 | −173.4 (5) | C12—C13—C14—C27 | 97.1 (6) |
C10—C1—C2—C3 | −56.4 (7) | C18—C13—C14—C27 | −78.0 (6) |
O1—C2—C3—O2 | −54.8 (6) | C12—C13—C14—C8 | −26.8 (7) |
C1—C2—C3—O2 | −175.1 (5) | C18—C13—C14—C8 | 158.1 (5) |
O1—C2—C3—C4 | −180.0 (5) | C7—C8—C14—C13 | 175.3 (5) |
C1—C2—C3—C4 | 59.7 (7) | C26—C8—C14—C13 | −64.8 (6) |
O2—C3—C4—C24 | −50.9 (7) | C9—C8—C14—C13 | 56.1 (6) |
C2—C3—C4—C24 | 73.3 (6) | C7—C8—C14—C15 | −63.9 (6) |
O2—C3—C4—C23 | 67.8 (6) | C26—C8—C14—C15 | 56.0 (6) |
C2—C3—C4—C23 | −167.9 (5) | C9—C8—C14—C15 | 176.9 (5) |
O2—C3—C4—C5 | −179.3 (4) | C7—C8—C14—C27 | 54.4 (6) |
C2—C3—C4—C5 | −55.0 (7) | C26—C8—C14—C27 | 174.3 (5) |
C24—C4—C5—C6 | 55.9 (7) | C9—C8—C14—C27 | −64.8 (6) |
C3—C4—C5—C6 | −177.6 (5) | C13—C14—C15—C16 | −41.5 (7) |
C23—C4—C5—C6 | −64.6 (7) | C27—C14—C15—C16 | 74.5 (6) |
C24—C4—C5—C10 | −74.8 (7) | C8—C14—C15—C16 | −162.8 (5) |
C3—C4—C5—C10 | 51.7 (7) | C14—C15—C16—C17 | 55.9 (7) |
C23—C4—C5—C10 | 164.7 (5) | C15—C16—C17—C28 | 60.9 (7) |
C10—C5—C6—C7 | −66.0 (6) | C15—C16—C17—C18 | −60.2 (7) |
C4—C5—C6—C7 | 159.7 (5) | C15—C16—C17—C22 | 176.0 (5) |
C5—C6—C7—C8 | 56.9 (7) | C12—C13—C18—C17 | 140.9 (5) |
C6—C7—C8—C26 | 76.6 (6) | C14—C13—C18—C17 | −43.9 (7) |
C6—C7—C8—C9 | −43.8 (6) | C12—C13—C18—C19 | −90.8 (6) |
C6—C7—C8—C14 | −162.1 (5) | C14—C13—C18—C19 | 84.3 (7) |
C7—C8—C9—C11 | 175.3 (5) | C28—C17—C18—C13 | −69.7 (6) |
C26—C8—C9—C11 | 56.4 (6) | C16—C17—C18—C13 | 52.6 (7) |
C14—C8—C9—C11 | −64.5 (5) | C22—C17—C18—C13 | 175.9 (5) |
C7—C8—C9—C10 | 43.2 (6) | C28—C17—C18—C19 | 161.1 (5) |
C26—C8—C9—C10 | −75.6 (6) | C16—C17—C18—C19 | −76.6 (6) |
C14—C8—C9—C10 | 163.4 (4) | C22—C17—C18—C19 | 46.7 (7) |
C2—C1—C10—C25 | −72.7 (6) | C13—C18—C19—C20 | 178.7 (5) |
C2—C1—C10—C5 | 50.6 (6) | C17—C18—C19—C20 | −53.8 (7) |
C2—C1—C10—C9 | 164.4 (5) | C18—C19—C20—C29 | −66.2 (7) |
C6—C5—C10—C25 | −64.6 (6) | C18—C19—C20—C21 | 56.8 (7) |
C4—C5—C10—C25 | 68.7 (7) | C18—C19—C20—C30 | 174.4 (6) |
C6—C5—C10—C1 | 176.4 (5) | C29—C20—C21—C22 | 66.7 (7) |
C4—C5—C10—C1 | −50.4 (6) | C19—C20—C21—C22 | −55.9 (7) |
C6—C5—C10—C9 | 61.8 (6) | C30—C20—C21—C22 | −173.7 (5) |
C4—C5—C10—C9 | −164.9 (5) | C20—C21—C22—C17 | 53.1 (7) |
C11—C9—C10—C25 | −56.4 (7) | C28—C17—C22—C21 | −165.0 (5) |
C8—C9—C10—C25 | 73.5 (6) | C18—C17—C22—C21 | −47.3 (7) |
C11—C9—C10—C1 | 62.0 (6) | C16—C17—C22—C21 | 75.5 (7) |
C8—C9—C10—C1 | −168.1 (5) | C24—C4—C23—O3 | 62.5 (7) |
C11—C9—C10—C5 | 177.3 (5) | C3—C4—C23—O3 | −59.3 (7) |
C8—C9—C10—C5 | −52.7 (6) | C5—C4—C23—O3 | −172.2 (5) |
C10—C9—C11—C12 | 176.2 (5) | C18—C17—C28—O5 | −20.4 (8) |
C8—C9—C11—C12 | 41.8 (7) | C16—C17—C28—O5 | −141.9 (7) |
C9—C11—C12—C13 | −11.9 (9) | C22—C17—C28—O5 | 98.9 (7) |
C11—C12—C13—C18 | 179.5 (6) | C18—C17—C28—O4 | 163.8 (5) |
C11—C12—C13—C14 | 4.2 (9) | C16—C17—C28—O4 | 42.4 (7) |
C12—C13—C14—C15 | −148.3 (5) | C22—C17—C28—O4 | −76.8 (6) |
C18—C13—C14—C15 | 36.6 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O5i | 0.82 | 1.96 | 2.744 (6) | 160 |
O3—H3O···O2 | 0.82 | 1.93 | 2.665 (6) | 148 |
O4—H4O···O3ii | 0.82 | 1.82 | 2.642 (7) | 174 |
Symmetry codes: (i) −x+1/2, −y, z−1/2; (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 topBond | Arjunolic Acid | Average |
C4-C5 | 1.570 (7) | 1.563 (9) |
C5-C10 | 1.557 (8) | 1.552 (8) |
C9-C10 | 1.562 (7) | 1.570 (10) |
C7-C8 | 1.551 (8) | 1.541 (8) |
C8-C9 | 1.565 (8) | 1.553 (8) |
C8-C14 | 1.578 (8) | 1.589 (6) |
C17-C22 | 1.559 (7) | 1.546 (13) |
C2-C3-C4 | 114.6 (5) | 114.2 (12) |
C1-C2-C3 | 110.9 (5) | 111.0 (12) |
C10-C1-C2 | 113.4 (5) | 113.5 (11) |
C4-C5-C10 | 117.1 (5) | 117.0 (9) |
C4-C5-C6 | 115.0 (4) | 114.4 (5) |
C6-C7-C8 | 115.5 (5) | 114.1 (7) |
C7-C8-C14 | 110.7 (4) | 110.5 (5) |
C8-C9-C10 | 118.2 (5) | 117.5 (8) |
C10-C9-C11 | 113.8 (4) | 113.2 (6) |
C14-C15-C16 | 115.7 (5) | 114.6 (5) |
C15-C16-C17 | 110.9 (5) | 112.4 (7) |
C16-C17-C18 | 109.9 (5) | 108.7 (11) |
C16-C17-C22 | 110.8 (5) | 112.0 (13) |
C18-C17-C22 | 111.7 (5) | 110.2 (12) |
C17-C18-C13 | 110.9 (5) | 112.3 (9) |
C17-C18-C19 | 112.5 (5) | 112.8 (10) |
C13-C18-C19 | 114.2 (5) | 111.9 (15) |
C18-C19-C20 | 114.1 (5) | 113.7 (20) |
C20-C21-C22 | 112.9 (5) | 112.8 (14) |
C21-C22-C17 | 114.0 (5) | 114.4 (10) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.