The title compound, C31H48O3, was obtained by methylation of 3-oxoolean-12-en-20-α-oic acid, isolated from the root bark of Austroplenckia populnea (Celastraceae). Rings A, B, D and E are in chair conformations and ring C is in an envelope conformation.
Supporting information
CCDC reference: 204691
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.007 Å
- R factor = 0.055
- wR factor = 0.159
- Data-to-parameter ratio = 7.9
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 25.08
From the CIF: _reflns_number_total 2486
Count of symmetry unique reflns 2531
Completeness (_total/calc) 98.22%
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.
The bark wood of Austroplenckia populnea (a voucher specimen, number 10473, deposited at the Herbarium of the Natural History Museum of The Universidade Federal de Minas Gerais) was reduced to a powder and extracted with methanol at room temperature. Further extraction was carried out using hexane, benzene and ethylacetate. The extract from hexane was purified by coloumn chromatography (silica gel) using increasing proportions of CH2Cl2 in hexane and ethylacetate in CHCl3 as solvent. The benzene extract was purified by column chromatography (silica gel). 3-oxoolean-12-en-20-α-carboxylic acid [katononic acid, (1)], was isolated, in both extracts, by elution with CHCl3 and crystallized from methanol/CHCl3. 3-Oxoolean-12-en-20-α-methylcarboxylate [methylkatononate,(2)] was obtained from (1) by treatment with CH2N2 in (C2H5)2O over aperiod of 36 h (Coxon & Wells, 1980). The pure methylkatononate was obtained as lustrous plates crystallized from CH3OH/CHCl3. MS, 13C, 1H NMR and X-ray data gave the formula C31H48O3. The MS showed the molecular ion at m/z 468 and fragment at m/z 262, associated with a retro-Diels–Alder fragmentation, indicating (2) was a member of an olean-12-ene system (Doddrell et al., 1974). The 1H NMR spectrum revealed the presence of seven methyl groups, one methoxy group, and one methine proton attached to the double bond. Unequivocal proof of the structure and complete stereochemistry of (2) was obtained by the single-crystal X-ray analysis.
Since the X-ray data do not allow the determination the enantiomer present in the structure, intensities of the Friedel pair reflections were averaged before refinement. All H atoms were included in calculated positions with C—H distances ranging from 0.98 to 1.00 Å and then included in the refinement in riding motion approximation with Uiso = 1.2Ueq (1.5Ueq for methyl groups) of the carrier atom.
Data collection: COLLECT (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-oxo-olean-12-en-20-alpha-methylcarboxylate
top
Crystal data top
C31H48O3 | F(000) = 1032 |
Mr = 468.69 | Dx = 1.19 Mg m−3 |
Monoclinic, C2 | Melting point = 158–159 K |
Hall symbol: C 2y | Mo Kα radiation, λ = 0.71070 Å |
a = 12.0144 (4) Å | Cell parameters from 2486 reflections |
b = 7.2750 (4) Å | θ = 2.0–25.1° |
c = 30.364 (2) Å | µ = 0.07 mm−1 |
β = 99.565 (2)° | T = 100 K |
V = 2617.1 (2) Å3 | Prism, colorless |
Z = 4 | 0.1 × 0.05 × 0.05 mm |
Data collection top
Nonius KappaCCD diffractometer | 1679 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.049 |
Horizonally mounted graphite crystal monochromator | θmax = 25.1°, θmin = 2.0° |
Detector resolution: 9 pixels mm-1 | h = −13→14 |
ϕ scans and ω scans winth κ offsets | k = −8→8 |
4283 measured reflections | l = −35→35 |
2486 independent reflections | |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.1561P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.159 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.26 e Å−3 |
2486 reflections | Δρmin = −0.26 e Å−3 |
315 parameters | |
Crystal data top
C31H48O3 | V = 2617.1 (2) Å3 |
Mr = 468.69 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 12.0144 (4) Å | µ = 0.07 mm−1 |
b = 7.2750 (4) Å | T = 100 K |
c = 30.364 (2) Å | 0.1 × 0.05 × 0.05 mm |
β = 99.565 (2)° | |
Data collection top
Nonius KappaCCD diffractometer | 1679 reflections with I > 2σ(I) |
4283 measured reflections | Rint = 0.049 |
2486 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.055 | 1 restraint |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.26 e Å−3 |
2486 reflections | Δρmin = −0.26 e Å−3 |
315 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.5667 (3) | 0.2258 (8) | 0.04821 (11) | 0.0761 (14) | |
O2 | 0.7052 (3) | 0.2735 (6) | 0.41372 (11) | 0.0600 (11) | |
O3 | 0.6856 (2) | 0.0910 (5) | 0.47063 (10) | 0.0417 (9) | |
C1 | 0.4828 (5) | 0.1682 (11) | 0.06096 (18) | 0.0616 (18) | |
C2 | 0.4714 (5) | −0.0271 (11) | 0.07388 (17) | 0.0617 (19) | |
H2A | 0.5365 | −0.099 | 0.0672 | 0.074* | |
H2B | 0.4016 | −0.0801 | 0.0566 | 0.074* | |
C3 | 0.4667 (4) | −0.0368 (9) | 0.12447 (16) | 0.0541 (15) | |
H3A | 0.4588 | −0.1667 | 0.1331 | 0.065* | |
H3B | 0.5386 | 0.0104 | 0.1414 | 0.065* | |
C4 | 0.3674 (4) | 0.0761 (8) | 0.13708 (15) | 0.0414 (13) | |
C5 | 0.3888 (3) | 0.1005 (8) | 0.18953 (15) | 0.0380 (12) | |
H5 | 0.4661 | 0.1548 | 0.1968 | 0.046* | |
C6 | 0.3959 (4) | −0.0836 (7) | 0.21568 (16) | 0.0443 (13) | |
H6A | 0.3302 | −0.1607 | 0.2034 | 0.053* | |
H6B | 0.4649 | −0.1499 | 0.2109 | 0.053* | |
C7 | 0.3983 (4) | −0.0603 (7) | 0.26503 (15) | 0.0371 (12) | |
H7 | 0.4116 | −0.1677 | 0.2829 | 0.045* | |
C8 | 0.3836 (3) | 0.0960 (6) | 0.28608 (14) | 0.0304 (10) | |
C28 | 0.8004 (3) | 0.1374 (7) | 0.49112 (16) | 0.0441 (13) | |
H28A | 0.8531 | 0.0958 | 0.4718 | 0.066* | |
H28B | 0.8185 | 0.0768 | 0.5203 | 0.066* | |
H28C | 0.807 | 0.2709 | 0.4951 | 0.066* | |
C9 | 0.3918 (3) | 0.0936 (7) | 0.33661 (14) | 0.0300 (10) | |
H9 | 0.37 | −0.033 | 0.3448 | 0.036* | |
C10 | 0.5142 (3) | 0.1236 (7) | 0.36022 (13) | 0.0330 (11) | |
H10A | 0.5631 | 0.0288 | 0.3498 | 0.04* | |
H10B | 0.5405 | 0.2452 | 0.3515 | 0.04* | |
C11 | 0.5277 (3) | 0.1147 (6) | 0.41125 (14) | 0.0326 (11) | |
C12 | 0.4493 (4) | 0.2618 (7) | 0.42627 (15) | 0.0395 (12) | |
H12A | 0.4544 | 0.2562 | 0.4591 | 0.047* | |
H12B | 0.4748 | 0.3853 | 0.4185 | 0.047* | |
C13 | 0.3265 (3) | 0.2333 (7) | 0.40411 (14) | 0.0361 (11) | |
H13A | 0.2804 | 0.3343 | 0.4135 | 0.043* | |
H13B | 0.2989 | 0.1169 | 0.4153 | 0.043* | |
C14 | 0.3072 (3) | 0.2263 (6) | 0.35261 (14) | 0.0325 (11) | |
C15 | 0.3214 (4) | 0.4166 (6) | 0.33309 (14) | 0.0343 (11) | |
H15A | 0.2698 | 0.5037 | 0.3446 | 0.041* | |
H15B | 0.3997 | 0.4595 | 0.3433 | 0.041* | |
C16 | 0.2971 (4) | 0.4180 (6) | 0.28240 (14) | 0.0340 (11) | |
H16A | 0.3117 | 0.543 | 0.2718 | 0.041* | |
H16B | 0.2161 | 0.3907 | 0.2725 | 0.041* | |
C17 | 0.3683 (4) | 0.2783 (6) | 0.26028 (14) | 0.0308 (11) | |
C18 | 0.3106 (4) | 0.2368 (6) | 0.21021 (14) | 0.0334 (11) | |
C19 | 0.2971 (4) | 0.4174 (7) | 0.18297 (15) | 0.0388 (12) | |
H19A | 0.3658 | 0.4928 | 0.1917 | 0.047* | |
H19B | 0.2326 | 0.487 | 0.1911 | 0.047* | |
C20 | 0.2776 (4) | 0.3910 (7) | 0.13173 (15) | 0.0423 (13) | |
H20A | 0.2038 | 0.3303 | 0.122 | 0.051* | |
H20B | 0.2755 | 0.5125 | 0.117 | 0.051* | |
C21 | 0.3712 (4) | 0.2743 (7) | 0.11763 (15) | 0.0420 (13) | |
H21 | 0.4422 | 0.3282 | 0.1345 | 0.05* | |
C22 | 0.3849 (4) | 0.2948 (9) | 0.06757 (16) | 0.0521 (16) | |
C23 | 0.4156 (5) | 0.4930 (10) | 0.05789 (19) | 0.0650 (18) | |
H23A | 0.4815 | 0.5313 | 0.0794 | 0.097* | |
H23B | 0.3517 | 0.5738 | 0.0605 | 0.097* | |
H23C | 0.4332 | 0.5011 | 0.0276 | 0.097* | |
C24 | 0.2775 (4) | 0.2435 (10) | 0.03406 (15) | 0.0569 (16) | |
H24A | 0.2933 | 0.253 | 0.0035 | 0.085* | |
H24B | 0.2161 | 0.3279 | 0.0378 | 0.085* | |
H24C | 0.2551 | 0.1172 | 0.0397 | 0.085* | |
C25 | 0.2574 (4) | −0.0292 (8) | 0.11874 (17) | 0.0481 (14) | |
H25A | 0.2645 | −0.0861 | 0.0901 | 0.072* | |
H25B | 0.1937 | 0.0568 | 0.1145 | 0.072* | |
H25C | 0.2444 | −0.1247 | 0.1401 | 0.072* | |
C26 | 0.5002 (4) | −0.0785 (7) | 0.42727 (15) | 0.0391 (12) | |
H26A | 0.4231 | −0.1121 | 0.4138 | 0.059* | |
H26B | 0.5068 | −0.0785 | 0.4599 | 0.059* | |
H26C | 0.5534 | −0.1677 | 0.4183 | 0.059* | |
C27 | 0.6473 (4) | 0.1695 (7) | 0.43046 (15) | 0.0354 (11) | |
C29 | 0.1869 (3) | 0.1527 (6) | 0.33732 (16) | 0.0375 (12) | |
H29A | 0.1778 | 0.0358 | 0.3524 | 0.056* | |
H29B | 0.1744 | 0.1334 | 0.3049 | 0.056* | |
H29C | 0.1321 | 0.2419 | 0.3449 | 0.056* | |
C30 | 0.4877 (4) | 0.3646 (6) | 0.26344 (15) | 0.0360 (12) | |
H30A | 0.4845 | 0.4682 | 0.2426 | 0.054* | |
H30B | 0.5404 | 0.2719 | 0.2557 | 0.054* | |
H30C | 0.5136 | 0.4082 | 0.294 | 0.054* | |
C31 | 0.1925 (3) | 0.1531 (7) | 0.20870 (15) | 0.0381 (12) | |
H31A | 0.1451 | 0.2388 | 0.2223 | 0.057* | |
H31B | 0.1989 | 0.037 | 0.2253 | 0.057* | |
H31C | 0.1583 | 0.1301 | 0.1776 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.035 (2) | 0.147 (4) | 0.047 (2) | −0.002 (2) | 0.0088 (17) | −0.006 (3) |
O2 | 0.050 (2) | 0.069 (3) | 0.055 (2) | −0.027 (2) | −0.0095 (17) | 0.024 (2) |
O3 | 0.0346 (17) | 0.047 (2) | 0.040 (2) | −0.0084 (17) | −0.0035 (14) | 0.0043 (18) |
C1 | 0.037 (3) | 0.113 (6) | 0.032 (3) | 0.007 (3) | −0.004 (2) | −0.007 (3) |
C2 | 0.042 (3) | 0.106 (6) | 0.037 (3) | 0.022 (4) | 0.004 (2) | −0.018 (3) |
C3 | 0.042 (3) | 0.075 (4) | 0.044 (3) | 0.014 (3) | 0.002 (2) | −0.013 (3) |
C4 | 0.030 (2) | 0.060 (4) | 0.033 (3) | 0.007 (3) | 0.002 (2) | −0.005 (3) |
C5 | 0.028 (2) | 0.050 (3) | 0.035 (3) | 0.009 (3) | 0.0026 (19) | −0.005 (3) |
C6 | 0.048 (3) | 0.038 (3) | 0.046 (3) | 0.009 (3) | 0.003 (2) | −0.006 (3) |
C7 | 0.038 (3) | 0.034 (3) | 0.039 (3) | 0.005 (2) | 0.003 (2) | 0.000 (2) |
C8 | 0.027 (2) | 0.028 (3) | 0.035 (3) | 0.000 (2) | 0.0013 (18) | −0.004 (2) |
C28 | 0.038 (3) | 0.045 (3) | 0.046 (3) | 0.001 (2) | −0.004 (2) | 0.002 (3) |
C9 | 0.031 (2) | 0.028 (2) | 0.032 (2) | 0.000 (2) | 0.0060 (18) | 0.000 (2) |
C10 | 0.033 (2) | 0.030 (3) | 0.036 (3) | 0.003 (2) | 0.0040 (19) | 0.003 (2) |
C11 | 0.029 (2) | 0.031 (3) | 0.037 (3) | −0.001 (2) | 0.0012 (19) | −0.002 (2) |
C12 | 0.039 (3) | 0.044 (3) | 0.036 (3) | 0.003 (2) | 0.007 (2) | −0.001 (3) |
C13 | 0.034 (2) | 0.041 (3) | 0.035 (3) | 0.004 (2) | 0.008 (2) | 0.003 (2) |
C14 | 0.029 (2) | 0.033 (3) | 0.036 (3) | 0.001 (2) | 0.005 (2) | −0.001 (2) |
C15 | 0.037 (3) | 0.028 (3) | 0.038 (3) | 0.002 (2) | 0.007 (2) | −0.002 (2) |
C16 | 0.033 (2) | 0.027 (3) | 0.042 (3) | −0.003 (2) | 0.005 (2) | −0.004 (2) |
C17 | 0.028 (2) | 0.030 (3) | 0.033 (3) | 0.001 (2) | 0.0017 (19) | −0.002 (2) |
C18 | 0.029 (2) | 0.034 (3) | 0.037 (3) | 0.001 (2) | 0.006 (2) | −0.005 (2) |
C19 | 0.037 (3) | 0.042 (3) | 0.036 (3) | 0.004 (2) | 0.003 (2) | 0.003 (2) |
C20 | 0.037 (3) | 0.054 (3) | 0.036 (3) | 0.007 (2) | 0.005 (2) | 0.006 (3) |
C21 | 0.030 (2) | 0.065 (4) | 0.029 (3) | −0.007 (3) | 0.000 (2) | −0.006 (3) |
C22 | 0.032 (3) | 0.089 (5) | 0.034 (3) | 0.006 (3) | 0.005 (2) | −0.001 (3) |
C23 | 0.051 (3) | 0.097 (5) | 0.045 (4) | −0.010 (3) | 0.004 (3) | 0.010 (3) |
C24 | 0.034 (3) | 0.098 (5) | 0.036 (3) | 0.004 (3) | −0.001 (2) | −0.006 (3) |
C25 | 0.040 (3) | 0.057 (4) | 0.045 (3) | 0.007 (3) | −0.003 (2) | −0.011 (3) |
C26 | 0.038 (3) | 0.043 (3) | 0.035 (3) | −0.005 (2) | 0.001 (2) | 0.003 (2) |
C27 | 0.035 (3) | 0.036 (3) | 0.036 (3) | −0.001 (2) | 0.006 (2) | −0.001 (2) |
C29 | 0.036 (2) | 0.031 (3) | 0.046 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C30 | 0.037 (3) | 0.035 (3) | 0.036 (3) | −0.004 (2) | 0.004 (2) | 0.004 (2) |
C31 | 0.034 (2) | 0.042 (3) | 0.038 (3) | 0.000 (2) | 0.005 (2) | −0.007 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.213 (7) | C14—C15 | 1.527 (7) |
O2—C27 | 1.197 (5) | C14—C29 | 1.538 (6) |
O3—C27 | 1.356 (5) | C15—C16 | 1.518 (6) |
O3—C28 | 1.456 (5) | C15—H15A | 0.9900 |
C1—C2 | 1.486 (10) | C15—H15B | 0.9900 |
C1—C22 | 1.534 (8) | C16—C17 | 1.551 (6) |
C2—C3 | 1.548 (7) | C16—H16A | 0.9900 |
C2—H2A | 0.9900 | C16—H16B | 0.9900 |
C2—H2B | 0.9900 | C17—C30 | 1.555 (6) |
C3—C4 | 1.548 (6) | C17—C18 | 1.591 (6) |
C3—H3A | 0.9900 | C18—C31 | 1.538 (6) |
C3—H3B | 0.9900 | C18—C19 | 1.546 (7) |
C4—C25 | 1.549 (7) | C19—C20 | 1.546 (6) |
C4—C21 | 1.562 (7) | C19—H19A | 0.9900 |
C4—C5 | 1.580 (6) | C19—H19B | 0.9900 |
C5—C6 | 1.552 (7) | C20—C21 | 1.526 (7) |
C5—C18 | 1.567 (6) | C20—H20A | 0.9900 |
C5—H5 | 1.0000 | C20—H20B | 0.9900 |
C6—C7 | 1.504 (6) | C21—C22 | 1.563 (7) |
C6—H6A | 0.9900 | C21—H21 | 1.0000 |
C6—H6B | 0.9900 | C22—C23 | 1.529 (9) |
C7—C8 | 1.331 (6) | C22—C24 | 1.550 (7) |
C7—H7 | 0.9500 | C23—H23A | 0.9800 |
C8—C9 | 1.521 (6) | C23—H23B | 0.9800 |
C8—C17 | 1.536 (7) | C23—H23C | 0.9800 |
C28—H28A | 0.9800 | C24—H24A | 0.9800 |
C28—H28B | 0.9800 | C24—H24B | 0.9800 |
C28—H28C | 0.9800 | C24—H24C | 0.9800 |
C9—C14 | 1.538 (6) | C25—H25A | 0.9800 |
C9—C10 | 1.541 (6) | C25—H25B | 0.9800 |
C9—H9 | 1.0000 | C25—H25C | 0.9800 |
C10—C11 | 1.532 (6) | C26—H26A | 0.9800 |
C10—H10A | 0.9900 | C26—H26B | 0.9800 |
C10—H10B | 0.9900 | C26—H26C | 0.9800 |
C11—C27 | 1.512 (6) | C29—H29A | 0.9800 |
C11—C26 | 1.541 (7) | C29—H29B | 0.9800 |
C11—C12 | 1.543 (6) | C29—H29C | 0.9800 |
C12—C13 | 1.531 (6) | C30—H30A | 0.9800 |
C12—H12A | 0.9900 | C30—H30B | 0.9800 |
C12—H12B | 0.9900 | C30—H30C | 0.9800 |
C13—C14 | 1.543 (6) | C31—H31A | 0.9800 |
C13—H13A | 0.9900 | C31—H31B | 0.9800 |
C13—H13B | 0.9900 | C31—H31C | 0.9800 |
| | | |
O1···C1i | 3.296 (6) | H12B···H15B | 2.3738 |
O1···C24i | 3.364 (6) | H13A···H15A | 2.4124 |
O1···O1i | 3.095 (5) | H13A···H29C | 2.5932 |
O1···C25ii | 3.374 (7) | H13A···O3viii | 2.9083 |
O1···H23C | 2.5772 | H13A···C27viii | 3.0071 |
O1···H24Ai | 2.4926 | H13B···C26 | 2.7765 |
O1···H23A | 2.6848 | H13B···H26A | 2.2420 |
O1···H25Aii | 2.8513 | H13B···H29A | 2.2791 |
O2···H10B | 2.5074 | H13B···O2vii | 2.7366 |
O2···H12B | 2.9118 | H15A···H13A | 2.4124 |
O2···H28A | 2.6266 | H15A···H29C | 2.5242 |
O2···H28C | 2.5685 | H15A···H10Aviii | 2.5215 |
O2···H13Bii | 2.7366 | H15B···C10 | 2.8098 |
O2···H26Aii | 2.7463 | H15B···C12 | 2.8768 |
O2···H29Aii | 2.6483 | H15B···C30 | 2.8850 |
O3···H26B | 2.4499 | H15B···H10B | 2.2841 |
O3···H26C | 2.7834 | H15B···H12B | 2.3738 |
O3···H13Aiii | 2.9083 | H15B···H30C | 2.2217 |
O3···H28Civ | 2.5461 | H16A···C7vi | 3.0860 |
C1···O1i | 3.296 (6) | H16A···C19 | 2.8258 |
C2···C23v | 3.573 (11) | H16A···H7vi | 2.4188 |
C7···C31 | 3.169 (6) | H16A···H19B | 2.5111 |
C10···C30 | 3.391 (6) | H16A···H30A | 2.4498 |
C17···C29 | 3.571 (6) | H16A···H30C | 2.5990 |
C23···C2vi | 3.573 (11) | H16B···C19 | 3.0404 |
C24···O1i | 3.364 (6) | H16B···C29 | 2.6892 |
C24···C25 | 3.288 (8) | H16B···C31 | 2.5756 |
C25···C24 | 3.288 (8) | H16B···H29B | 2.2122 |
C25···C31 | 3.246 (7) | H16B···H31A | 1.9595 |
C25···O1vii | 3.374 (7) | H19A···C16 | 3.0522 |
C29···C17 | 3.571 (6) | H19A···C30 | 2.5882 |
C30···C10 | 3.391 (6) | H19A···H6Avi | 2.5912 |
C31···C7 | 3.169 (6) | H19A···H21 | 2.4122 |
C31···C25 | 3.246 (7) | H19A···H30A | 1.9297 |
C2···H25A | 2.6487 | H19B···C16 | 2.7982 |
C2···H24C | 2.8347 | H19B···H16A | 2.5111 |
C3···H20Aiii | 3.0208 | H19B···H31A | 2.3648 |
C3···H6B | 2.7544 | H19B···H3Bviii | 2.5630 |
C4···H31C | 3.0008 | H20A···C24 | 3.0172 |
C4···H24C | 3.0538 | H20A···C25 | 2.6992 |
C5···H30B | 2.7741 | H20A···C31 | 2.9537 |
C6···H25C | 2.6992 | H20A···H24B | 2.5863 |
C6···H3A | 2.8016 | H20A···H25B | 2.0044 |
C6···H31B | 2.5859 | H20A···H31C | 2.3603 |
C7···H31B | 2.5953 | H20A···C3viii | 3.0208 |
C7···H10A | 3.0461 | H20A···H2Aviii | 2.4426 |
C7···H30B | 2.9993 | H20A···H3Bviii | 2.5287 |
C7···H16Av | 3.0860 | H20B···C23 | 2.6591 |
C8···H5 | 3.0662 | H20B···H23B | 2.1213 |
C8···H29B | 2.6833 | H21···C18 | 3.0702 |
C8···H31B | 2.6746 | H21···H3B | 2.5782 |
C9···H26A | 2.7537 | H21···H5 | 2.2513 |
C10···H30C | 2.8864 | H21···H19A | 2.4122 |
C10···H15B | 2.8098 | H21···H23A | 2.3388 |
C12···H15B | 2.8768 | H23A···O1 | 2.6848 |
C13···H26A | 2.7630 | H23A···H21 | 2.3388 |
C15···H10B | 2.8824 | H23B···C20 | 2.8080 |
C15···H12B | 2.9292 | H23B···H2Bvi | 2.5954 |
C15···H30C | 2.7675 | H23B···H20B | 2.1213 |
C16···H19B | 2.7982 | H23B···H24B | 2.4407 |
C16···H31A | 2.6943 | H23C···O1 | 2.5772 |
C16···H29B | 2.6953 | H23C···H24A | 2.4918 |
C16···H19A | 3.0522 | H23C···H23Ci | 2.5049 |
C17···H29B | 3.0706 | H24A···H23C | 2.4918 |
C18···H21 | 3.0702 | H24A···O1i | 2.4926 |
C19···H16A | 2.8258 | H24B···C20 | 2.8620 |
C19···H30A | 2.6707 | H24B···H20A | 2.5863 |
C19···H16B | 3.0404 | H24B···H23B | 2.4407 |
C20···H24B | 2.8620 | H24B···H2Aviii | 2.5250 |
C20···H23B | 2.8080 | H24C···C2 | 2.8347 |
C20···H31C | 2.8735 | H24C···C4 | 3.0538 |
C20···H3Bviii | 3.0612 | H24C···C25 | 2.6215 |
C20···H25B | 2.6510 | H24C···H2B | 2.2633 |
C23···H20B | 2.6591 | H24C···H25A | 2.1178 |
C24···H2B | 2.8097 | H24C···H25B | 2.5392 |
C24···H25A | 2.9595 | H25A···C2 | 2.6487 |
C24···H20A | 3.0172 | H25A···C24 | 2.9595 |
C25···H20A | 2.6992 | H25A···H2B | 2.0750 |
C25···H2B | 2.7895 | H25A···H3A | 2.5473 |
C25···H6A | 2.7449 | H25A···H24C | 2.1178 |
C25···H31C | 2.5809 | H25A···O1vii | 2.8513 |
C25···H24C | 2.6215 | H25B···C20 | 2.6510 |
C26···H9 | 2.7442 | H25B···C31 | 2.9481 |
C26···H13B | 2.7765 | H25B···H20A | 2.0044 |
C27···H13Aiii | 3.0071 | H25B···H24C | 2.5392 |
C28···H28Civ | 3.0212 | H25B···H31C | 2.0998 |
C29···H16B | 2.6892 | H25C···C6 | 2.6992 |
C29···H30Cvii | 2.8846 | H25C···C31 | 3.0409 |
C30···H10B | 2.7822 | H25C···H6A | 2.0411 |
C30···H5 | 2.5125 | H25C···H31C | 2.4892 |
C30···H29Bii | 3.0824 | H26A···C9 | 2.7537 |
C30···H15B | 2.8850 | H26A···C13 | 2.7630 |
C30···H19A | 2.5882 | H26A···H9 | 2.1654 |
C31···H6A | 2.8393 | H26A···H13B | 2.2420 |
C31···H16B | 2.5756 | H26A···O2vii | 2.7463 |
C31···H20A | 2.9537 | H26B···O3 | 2.4499 |
C31···H25B | 2.9481 | H26B···H12A | 2.5141 |
C31···H25C | 3.0409 | H26B···H26Bix | 2.4690 |
C31···H29B | 2.9695 | H26C···O3 | 2.7834 |
C31···H6Bviii | 3.0979 | H26C···H10A | 2.5419 |
H2A···H20Aiii | 2.4426 | H28A···O2 | 2.6266 |
H2A···H24Biii | 2.5250 | H28C···O2 | 2.5685 |
H2B···C24 | 2.8097 | H28C···O3x | 2.5461 |
H2B···C25 | 2.7895 | H28C···C28x | 3.0212 |
H2B···H23Bv | 2.5954 | H29A···H9 | 2.4101 |
H2B···H24C | 2.2633 | H29A···H13B | 2.2791 |
H2B···H25A | 2.0750 | H29A···O2vii | 2.6483 |
H3A···C6 | 2.8016 | H29A···H30Cvii | 2.5957 |
H3A···H6B | 2.3541 | H29B···C8 | 2.6833 |
H3A···H25A | 2.5473 | H29B···C16 | 2.6953 |
H3B···H5 | 2.2756 | H29B···C17 | 3.0706 |
H3B···H21 | 2.5782 | H29B···C31 | 2.9695 |
H3B···C20iii | 3.0612 | H29B···H16B | 2.2122 |
H3B···H19Biii | 2.5630 | H29B···H31A | 2.5922 |
H3B···H20Aiii | 2.5287 | H29B···H31B | 2.5811 |
H5···C8 | 3.0662 | H29B···C30vii | 3.0824 |
H5···C30 | 2.5125 | H29B···H30Cvii | 2.5122 |
H5···H3B | 2.2756 | H29C···H13A | 2.5932 |
H5···H21 | 2.2513 | H29C···H15A | 2.5242 |
H5···H30B | 2.0469 | H29C···H10Aviii | 2.2599 |
H6A···C25 | 2.7449 | H30A···C19 | 2.6707 |
H6A···C31 | 2.8393 | H30A···H16A | 2.4498 |
H6A···H19Av | 2.5912 | H30A···H19A | 1.9297 |
H6A···H25C | 2.0411 | H30B···C5 | 2.7741 |
H6A···H31B | 2.3127 | H30B···C7 | 2.9993 |
H6B···C3 | 2.7544 | H30B···H5 | 2.0469 |
H6B···H3A | 2.3541 | H30C···C10 | 2.8864 |
H6B···C31iii | 3.0979 | H30C···C15 | 2.7675 |
H6B···H31Aiii | 2.2837 | H30C···H10B | 2.0917 |
H7···H9 | 2.2470 | H30C···H15B | 2.2217 |
H7···H16Av | 2.4188 | H30C···H16A | 2.5990 |
H9···C26 | 2.7442 | H30C···C29ii | 2.8846 |
H9···H7 | 2.2470 | H30C···H29Aii | 2.5957 |
H9···H26A | 2.1654 | H30C···H29Bii | 2.5122 |
H9···H29A | 2.4101 | H31A···C16 | 2.6943 |
H10A···C7 | 3.0461 | H31A···H16B | 1.9595 |
H10A···H26C | 2.5419 | H31A···H19B | 2.3648 |
H10A···H15Aiii | 2.5215 | H31A···H29B | 2.5922 |
H10A···H29Ciii | 2.2599 | H31A···H6Bviii | 2.2837 |
H10B···O2 | 2.5074 | H31B···C6 | 2.5859 |
H10B···C15 | 2.8824 | H31B···C7 | 2.5953 |
H10B···C30 | 2.7822 | H31B···C8 | 2.6746 |
H10B···H12B | 2.5168 | H31B···H6A | 2.3127 |
H10B···H15B | 2.2841 | H31B···H29B | 2.5811 |
H10B···H30C | 2.0917 | H31C···C4 | 3.0008 |
H12A···H26B | 2.5141 | H31C···C20 | 2.8735 |
H12A···H12Aix | 2.5414 | H31C···C25 | 2.5809 |
H12B···O2 | 2.9118 | H31C···H20A | 2.3603 |
H12B···C15 | 2.9292 | H31C···H25B | 2.0998 |
H12B···H10B | 2.5168 | H31C···H25C | 2.4892 |
| | | |
C27—O3—C28 | 116.2 (3) | C15—C16—C17 | 114.1 (4) |
O1—C1—C2 | 122.2 (6) | C15—C16—H16A | 108.7 |
O1—C1—C22 | 122.1 (7) | C17—C16—H16A | 108.7 |
C2—C1—C22 | 115.6 (5) | C15—C16—H16B | 108.7 |
C1—C2—C3 | 109.0 (5) | C17—C16—H16B | 108.7 |
C1—C2—H2A | 109.9 | H16A—C16—H16B | 107.6 |
C3—C2—H2A | 109.9 | C8—C17—C16 | 111.9 (3) |
C1—C2—H2B | 109.9 | C8—C17—C30 | 106.6 (3) |
C3—C2—H2B | 109.9 | C16—C17—C30 | 106.1 (4) |
H2A—C2—H2B | 108.3 | C8—C17—C18 | 108.7 (4) |
C4—C3—C2 | 112.2 (4) | C16—C17—C18 | 110.7 (3) |
C4—C3—H3A | 109.2 | C30—C17—C18 | 112.7 (3) |
C2—C3—H3A | 109.2 | C31—C18—C19 | 107.8 (4) |
C4—C3—H3B | 109.2 | C31—C18—C5 | 110.4 (4) |
C2—C3—H3B | 109.2 | C19—C18—C5 | 109.9 (4) |
H3A—C3—H3B | 107.9 | C31—C18—C17 | 110.9 (3) |
C3—C4—C25 | 107.2 (4) | C19—C18—C17 | 109.9 (4) |
C3—C4—C21 | 108.9 (4) | C5—C18—C17 | 107.9 (3) |
C25—C4—C21 | 113.4 (4) | C18—C19—C20 | 114.7 (4) |
C3—C4—C5 | 107.8 (4) | C18—C19—H19A | 108.6 |
C25—C4—C5 | 113.8 (4) | C20—C19—H19A | 108.6 |
C21—C4—C5 | 105.5 (4) | C18—C19—H19B | 108.6 |
C6—C5—C18 | 109.1 (4) | C20—C19—H19B | 108.6 |
C6—C5—C4 | 113.9 (4) | H19A—C19—H19B | 107.6 |
C18—C5—C4 | 117.9 (4) | C21—C20—C19 | 110.8 (4) |
C6—C5—H5 | 104.9 | C21—C20—H20A | 109.5 |
C18—C5—H5 | 104.9 | C19—C20—H20A | 109.5 |
C4—C5—H5 | 104.9 | C21—C20—H20B | 109.5 |
C7—C6—C5 | 113.8 (4) | C19—C20—H20B | 109.5 |
C7—C6—H6A | 108.8 | H20A—C20—H20B | 108.1 |
C5—C6—H6A | 108.8 | C20—C21—C4 | 109.8 (4) |
C7—C6—H6B | 108.8 | C20—C21—C22 | 114.9 (4) |
C5—C6—H6B | 108.8 | C4—C21—C22 | 118.1 (4) |
H6A—C6—H6B | 107.7 | C20—C21—H21 | 104.1 |
C8—C7—C6 | 126.4 (5) | C4—C21—H21 | 104.1 |
C8—C7—H7 | 116.8 | C22—C21—H21 | 104.1 |
C6—C7—H7 | 116.8 | C23—C22—C1 | 109.0 (5) |
C7—C8—C9 | 118.9 (4) | C23—C22—C24 | 107.6 (5) |
C7—C8—C17 | 120.5 (4) | C1—C22—C24 | 110.0 (5) |
C9—C8—C17 | 120.5 (4) | C23—C22—C21 | 110.2 (5) |
O3—C28—H28A | 109.5 | C1—C22—C21 | 106.1 (4) |
O3—C28—H28B | 109.5 | C24—C22—C21 | 113.9 (4) |
H28A—C28—H28B | 109.5 | C22—C23—H23A | 109.5 |
O3—C28—H28C | 109.5 | C22—C23—H23B | 109.5 |
H28A—C28—H28C | 109.5 | H23A—C23—H23B | 109.5 |
H28B—C28—H28C | 109.5 | C22—C23—H23C | 109.5 |
C8—C9—C14 | 112.1 (3) | H23A—C23—H23C | 109.5 |
C8—C9—C10 | 111.4 (3) | H23B—C23—H23C | 109.5 |
C14—C9—C10 | 113.2 (4) | C22—C24—H24A | 109.5 |
C8—C9—H9 | 106.6 | C22—C24—H24B | 109.5 |
C14—C9—H9 | 106.6 | H24A—C24—H24B | 109.5 |
C10—C9—H9 | 106.6 | C22—C24—H24C | 109.5 |
C11—C10—C9 | 113.4 (3) | H24A—C24—H24C | 109.5 |
C11—C10—H10A | 108.9 | H24B—C24—H24C | 109.5 |
C9—C10—H10A | 108.9 | C4—C25—H25A | 109.5 |
C11—C10—H10B | 108.9 | C4—C25—H25B | 109.5 |
C9—C10—H10B | 108.9 | H25A—C25—H25B | 109.5 |
H10A—C10—H10B | 107.7 | C4—C25—H25C | 109.5 |
C27—C11—C10 | 108.2 (3) | H25A—C25—H25C | 109.5 |
C27—C11—C26 | 111.0 (4) | H25B—C25—H25C | 109.5 |
C10—C11—C26 | 111.4 (4) | C11—C26—H26A | 109.5 |
C27—C11—C12 | 106.9 (4) | C11—C26—H26B | 109.5 |
C10—C11—C12 | 107.6 (4) | H26A—C26—H26B | 109.5 |
C26—C11—C12 | 111.5 (3) | C11—C26—H26C | 109.5 |
C13—C12—C11 | 111.5 (4) | H26A—C26—H26C | 109.5 |
C13—C12—H12A | 109.3 | H26B—C26—H26C | 109.5 |
C11—C12—H12A | 109.3 | O2—C27—O3 | 121.0 (4) |
C13—C12—H12B | 109.3 | O2—C27—C11 | 125.8 (4) |
C11—C12—H12B | 109.3 | O3—C27—C11 | 113.2 (4) |
H12A—C12—H12B | 108.0 | C14—C29—H29A | 109.5 |
C12—C13—C14 | 114.9 (3) | C14—C29—H29B | 109.5 |
C12—C13—H13A | 108.5 | H29A—C29—H29B | 109.5 |
C14—C13—H13A | 108.5 | C14—C29—H29C | 109.5 |
C12—C13—H13B | 108.5 | H29A—C29—H29C | 109.5 |
C14—C13—H13B | 108.5 | H29B—C29—H29C | 109.5 |
H13A—C13—H13B | 107.5 | C17—C30—H30A | 109.5 |
C15—C14—C29 | 111.0 (4) | C17—C30—H30B | 109.5 |
C15—C14—C9 | 108.9 (3) | H30A—C30—H30B | 109.5 |
C29—C14—C9 | 108.9 (4) | C17—C30—H30C | 109.5 |
C15—C14—C13 | 110.8 (4) | H30A—C30—H30C | 109.5 |
C29—C14—C13 | 107.0 (3) | H30B—C30—H30C | 109.5 |
C9—C14—C13 | 110.2 (4) | C18—C31—H31A | 109.5 |
C16—C15—C14 | 112.6 (4) | C18—C31—H31B | 109.5 |
C16—C15—H15A | 109.1 | H31A—C31—H31B | 109.5 |
C14—C15—H15A | 109.1 | C18—C31—H31C | 109.5 |
C16—C15—H15B | 109.1 | H31A—C31—H31C | 109.5 |
C14—C15—H15B | 109.1 | H31B—C31—H31C | 109.5 |
H15A—C15—H15B | 107.8 | | |
| | | |
O1—C1—C2—C3 | 114.2 (5) | C15—C16—C17—C30 | −77.3 (4) |
C22—C1—C2—C3 | −62.1 (6) | C15—C16—C17—C18 | 160.0 (4) |
C1—C2—C3—C4 | 58.6 (6) | C6—C5—C18—C31 | −58.1 (5) |
C2—C3—C4—C25 | 71.8 (6) | C4—C5—C18—C31 | 73.8 (5) |
C2—C3—C4—C21 | −51.3 (6) | C6—C5—C18—C19 | −176.9 (4) |
C2—C3—C4—C5 | −165.3 (5) | C4—C5—C18—C19 | −45.0 (5) |
C3—C4—C5—C6 | −60.1 (5) | C6—C5—C18—C17 | 63.3 (5) |
C25—C4—C5—C6 | 58.7 (5) | C4—C5—C18—C17 | −164.9 (4) |
C21—C4—C5—C6 | −176.3 (4) | C8—C17—C18—C31 | 62.5 (4) |
C3—C4—C5—C18 | 170.3 (4) | C16—C17—C18—C31 | −60.8 (5) |
C25—C4—C5—C18 | −70.9 (6) | C30—C17—C18—C31 | −179.6 (4) |
C21—C4—C5—C18 | 54.0 (5) | C8—C17—C18—C19 | −178.4 (3) |
C18—C5—C6—C7 | −37.2 (5) | C16—C17—C18—C19 | 58.3 (4) |
C4—C5—C6—C7 | −171.1 (3) | C30—C17—C18—C19 | −60.4 (4) |
C5—C6—C7—C8 | 7.2 (7) | C8—C17—C18—C5 | −58.6 (4) |
C6—C7—C8—C9 | −178.5 (4) | C16—C17—C18—C5 | 178.1 (4) |
C6—C7—C8—C17 | −3.5 (7) | C30—C17—C18—C5 | 59.4 (5) |
C7—C8—C9—C14 | −143.7 (4) | C31—C18—C19—C20 | −77.2 (5) |
C17—C8—C9—C14 | 41.2 (5) | C5—C18—C19—C20 | 43.2 (5) |
C7—C8—C9—C10 | 88.3 (5) | C17—C18—C19—C20 | 161.8 (3) |
C17—C8—C9—C10 | −86.8 (5) | C18—C19—C20—C21 | −54.9 (5) |
C8—C9—C10—C11 | −177.7 (4) | C19—C20—C21—C4 | 64.6 (5) |
C14—C9—C10—C11 | 54.9 (5) | C19—C20—C21—C22 | −159.5 (4) |
C9—C10—C11—C27 | −173.0 (4) | C3—C4—C21—C20 | −177.1 (4) |
C9—C10—C11—C26 | 64.7 (5) | C25—C4—C21—C20 | 63.6 (5) |
C9—C10—C11—C12 | −57.8 (5) | C5—C4—C21—C20 | −61.5 (4) |
C27—C11—C12—C13 | 173.1 (4) | C3—C4—C21—C22 | 48.6 (5) |
C10—C11—C12—C13 | 57.1 (5) | C25—C4—C21—C22 | −70.7 (5) |
C26—C11—C12—C13 | −65.4 (5) | C5—C4—C21—C22 | 164.1 (3) |
C11—C12—C13—C14 | −55.3 (6) | O1—C1—C22—C23 | −2.7 (7) |
C8—C9—C14—C15 | −52.7 (5) | C2—C1—C22—C23 | 173.6 (5) |
C10—C9—C14—C15 | 74.3 (4) | O1—C1—C22—C24 | 115.0 (6) |
C8—C9—C14—C29 | 68.5 (5) | C2—C1—C22—C24 | −68.6 (6) |
C10—C9—C14—C29 | −164.5 (4) | O1—C1—C22—C21 | −121.4 (5) |
C8—C9—C14—C13 | −174.5 (4) | C2—C1—C22—C21 | 55.0 (6) |
C10—C9—C14—C13 | −47.5 (5) | C20—C21—C22—C23 | 61.7 (5) |
C12—C13—C14—C15 | −71.8 (5) | C4—C21—C22—C23 | −166.2 (4) |
C12—C13—C14—C29 | 167.0 (4) | C20—C21—C22—C1 | 179.6 (5) |
C12—C13—C14—C9 | 48.8 (6) | C4—C21—C22—C1 | −48.3 (6) |
C29—C14—C15—C16 | −58.2 (5) | C20—C21—C22—C24 | −59.2 (7) |
C9—C14—C15—C16 | 61.7 (5) | C4—C21—C22—C24 | 72.9 (6) |
C13—C14—C15—C16 | −177.0 (3) | C28—O3—C27—O2 | −1.4 (6) |
C14—C15—C16—C17 | −55.5 (5) | C28—O3—C27—C11 | 179.9 (4) |
C7—C8—C17—C16 | 151.9 (4) | C10—C11—C27—O2 | 29.8 (6) |
C9—C8—C17—C16 | −33.1 (5) | C26—C11—C27—O2 | 152.4 (5) |
C7—C8—C17—C30 | −92.4 (5) | C12—C11—C27—O2 | −85.8 (5) |
C9—C8—C17—C30 | 82.6 (4) | C10—C11—C27—O3 | −151.5 (4) |
C7—C8—C17—C18 | 29.3 (5) | C26—C11—C27—O3 | −28.9 (5) |
C9—C8—C17—C18 | −155.7 (3) | C12—C11—C27—O3 | 92.9 (4) |
C15—C16—C17—C8 | 38.6 (5) | | |
Symmetry codes: (i) −x+1, y, −z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y−1/2, z; (iv) −x+3/2, y−1/2, −z+1; (v) x, y−1, z; (vi) x, y+1, z; (vii) x−1/2, y−1/2, z; (viii) x−1/2, y+1/2, z; (ix) −x+1, y, −z+1; (x) −x+3/2, y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24A···O1i | 0.98 | 2.49 | 3.364 (6) | 148 |
C28—H28C···O3x | 0.98 | 2.55 | 3.493 (6) | 162 |
C29—H29A···O2vii | 0.98 | 2.65 | 3.587 (6) | 160 |
Symmetry codes: (i) −x+1, y, −z; (vii) x−1/2, y−1/2, z; (x) −x+3/2, y+1/2, −z+1. |
Experimental details
Crystal data |
Chemical formula | C31H48O3 |
Mr | 468.69 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 100 |
a, b, c (Å) | 12.0144 (4), 7.2750 (4), 30.364 (2) |
β (°) | 99.565 (2) |
V (Å3) | 2617.1 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.1 × 0.05 × 0.05 |
|
Data collection |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4283, 2486, 1679 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.596 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.159, 1.09 |
No. of reflections | 2486 |
No. of parameters | 315 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.26 |
Selected geometric parameters (Å, º) topO1—C1 | 1.213 (7) | O3—C27 | 1.356 (5) |
O2—C27 | 1.197 (5) | O3—C28 | 1.456 (5) |
| | | |
C27—O3—C28 | 116.2 (3) | O2—C27—O3 | 121.0 (4) |
O1—C1—C2 | 122.2 (6) | O2—C27—C11 | 125.8 (4) |
O1—C1—C22 | 122.1 (7) | O3—C27—C11 | 113.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24A···O1i | 0.98 | 2.49 | 3.364 (6) | 148 |
C28—H28C···O3ii | 0.98 | 2.55 | 3.493 (6) | 162 |
C29—H29A···O2iii | 0.98 | 2.65 | 3.587 (6) | 160 |
Symmetry codes: (i) −x+1, y, −z; (ii) −x+3/2, y+1/2, −z+1; (iii) x−1/2, y−1/2, z. |
Considerable attention has arisen from the investigation of chemical constituents of plants of the Celastraceae family, on account of the antitumoral and antileukemic activities found in maytansinoids and quinonemethide triterpenes isolated from plants of that family (Marine-Bettolo, 1974). In previous papers, we described the chemical constitution of the root bark (Sousa et al., 1988), bark wood (Sousa, Silva, Pedersoli & Alves, 1990) and root wood (Sousa, Silva & Pedersoli, 1990) of Austroplenckia populnea (Reiss) Lundell, specimen of the Celastraceae family. The plant is popularly known in the state of Minas Gerais (Brazil) as `mangabeira-brava', and the decoction of its branches is used as a traditional antidysenteric medicine (Corrêa, 1978).
The title compound, (I), was isolated according to the the procedure described in the Experimental section. Fig 1 shows an ORTEP-3 (Farrugia, 1997) view of (I) with the atom-numbering scheme. All rings adopt chair conformations, except for the alkene ring C, which is in an envelope conformation, with C18 in the flap position. The ring junctions A/B, B/C, and D/E are trans, trans, and cis, respectively. Selected bond lengths and angles are given in Table 1. The mean length of C—C single bonds is 1.52 (2) Å and the C7═C8 bond length is 1.331 (6) Å, which agree well with the range expected for formal single and double bonds, respectively. The two carbonyls have very similar bond lengths: C1═O1 = 1.213 (7) Å and C27═O2 = 1.197 (5) Å. On the other hand, the two C—O bonds differ from each other by 0.1 Å; C27═O3 = 1.356 (5) Å and C28═O3 = 1.456 (5) Å. This difference, which is comparable to other similar triterpenes (Cota et al., 1990a,b), is probably due to resonance involving the carboxyl group O2═C27═O3.
In the crystal structure, molecules are connected by weak C—H···O hydrogen bonds. The crystal packing and the intermolecular interactions of (I) are shown in Fig 2.