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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803000965/lh6025sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803000965/lh60252sup2.hkl
Contains datablock 2

CCDC reference: 204691

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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.

Comment top

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 C7C8 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: C1O1 = 1.213 (7) Å and C27O2 = 1.197 (5) Å. On the other hand, the two C—O bonds differ from each other by 0.1 Å; C27O3 = 1.356 (5) Å and C28O3 = 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 O2C27O3.

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.

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. View of (2) (50% probability displacement ellipsoids).
[Figure 2] Fig. 2. Packing of (2), showing the weak hydrogen-bond contacts with dotted lines.
3-oxo-olean-12-en-20-alpha-methylcarboxylate top
Crystal data top
C31H48O3F(000) = 1032
Mr = 468.69Dx = 1.19 Mg m3
Monoclinic, C2Melting point = 158–159 K
Hall symbol: C 2yMo Kα radiation, λ = 0.71070 Å
a = 12.0144 (4) ÅCell parameters from 2486 reflections
b = 7.2750 (4) Åθ = 2.0–25.1°
c = 30.364 (2) ŵ = 0.07 mm1
β = 99.565 (2)°T = 100 K
V = 2617.1 (2) Å3Prism, colorless
Z = 40.1 × 0.05 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
1679 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Horizonally mounted graphite crystal monochromatorθmax = 25.1°, θmin = 2.0°
Detector resolution: 9 pixels mm-1h = 1314
ϕ scans and ω scans winth κ offsetsk = 88
4283 measured reflectionsl = 3535
2486 independent reflections
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH-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 = 1.09Δρmax = 0.26 e Å3
2486 reflectionsΔρmin = 0.26 e Å3
315 parameters
Crystal data top
C31H48O3V = 2617.1 (2) Å3
Mr = 468.69Z = 4
Monoclinic, C2Mo Kα radiation
a = 12.0144 (4) ŵ = 0.07 mm1
b = 7.2750 (4) ÅT = 100 K
c = 30.364 (2) Å0.1 × 0.05 × 0.05 mm
β = 99.565 (2)°
Data collection top
Nonius KappaCCD
diffractometer
1679 reflections with I > 2σ(I)
4283 measured reflectionsRint = 0.049
2486 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.159H-atom parameters constrained
S = 1.09Δρmax = 0.26 e Å3
2486 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
O10.5667 (3)0.2258 (8)0.04821 (11)0.0761 (14)
O20.7052 (3)0.2735 (6)0.41372 (11)0.0600 (11)
O30.6856 (2)0.0910 (5)0.47063 (10)0.0417 (9)
C10.4828 (5)0.1682 (11)0.06096 (18)0.0616 (18)
C20.4714 (5)0.0271 (11)0.07388 (17)0.0617 (19)
H2A0.53650.0990.06720.074*
H2B0.40160.08010.05660.074*
C30.4667 (4)0.0368 (9)0.12447 (16)0.0541 (15)
H3A0.45880.16670.13310.065*
H3B0.53860.01040.14140.065*
C40.3674 (4)0.0761 (8)0.13708 (15)0.0414 (13)
C50.3888 (3)0.1005 (8)0.18953 (15)0.0380 (12)
H50.46610.15480.19680.046*
C60.3959 (4)0.0836 (7)0.21568 (16)0.0443 (13)
H6A0.33020.16070.20340.053*
H6B0.46490.14990.21090.053*
C70.3983 (4)0.0603 (7)0.26503 (15)0.0371 (12)
H70.41160.16770.28290.045*
C80.3836 (3)0.0960 (6)0.28608 (14)0.0304 (10)
C280.8004 (3)0.1374 (7)0.49112 (16)0.0441 (13)
H28A0.85310.09580.47180.066*
H28B0.81850.07680.52030.066*
H28C0.8070.27090.49510.066*
C90.3918 (3)0.0936 (7)0.33661 (14)0.0300 (10)
H90.370.0330.34480.036*
C100.5142 (3)0.1236 (7)0.36022 (13)0.0330 (11)
H10A0.56310.02880.34980.04*
H10B0.54050.24520.35150.04*
C110.5277 (3)0.1147 (6)0.41125 (14)0.0326 (11)
C120.4493 (4)0.2618 (7)0.42627 (15)0.0395 (12)
H12A0.45440.25620.45910.047*
H12B0.47480.38530.41850.047*
C130.3265 (3)0.2333 (7)0.40411 (14)0.0361 (11)
H13A0.28040.33430.41350.043*
H13B0.29890.11690.41530.043*
C140.3072 (3)0.2263 (6)0.35261 (14)0.0325 (11)
C150.3214 (4)0.4166 (6)0.33309 (14)0.0343 (11)
H15A0.26980.50370.34460.041*
H15B0.39970.45950.34330.041*
C160.2971 (4)0.4180 (6)0.28240 (14)0.0340 (11)
H16A0.31170.5430.27180.041*
H16B0.21610.39070.27250.041*
C170.3683 (4)0.2783 (6)0.26028 (14)0.0308 (11)
C180.3106 (4)0.2368 (6)0.21021 (14)0.0334 (11)
C190.2971 (4)0.4174 (7)0.18297 (15)0.0388 (12)
H19A0.36580.49280.19170.047*
H19B0.23260.4870.19110.047*
C200.2776 (4)0.3910 (7)0.13173 (15)0.0423 (13)
H20A0.20380.33030.1220.051*
H20B0.27550.51250.1170.051*
C210.3712 (4)0.2743 (7)0.11763 (15)0.0420 (13)
H210.44220.32820.13450.05*
C220.3849 (4)0.2948 (9)0.06757 (16)0.0521 (16)
C230.4156 (5)0.4930 (10)0.05789 (19)0.0650 (18)
H23A0.48150.53130.07940.097*
H23B0.35170.57380.06050.097*
H23C0.43320.50110.02760.097*
C240.2775 (4)0.2435 (10)0.03406 (15)0.0569 (16)
H24A0.29330.2530.00350.085*
H24B0.21610.32790.03780.085*
H24C0.25510.11720.03970.085*
C250.2574 (4)0.0292 (8)0.11874 (17)0.0481 (14)
H25A0.26450.08610.09010.072*
H25B0.19370.05680.11450.072*
H25C0.24440.12470.14010.072*
C260.5002 (4)0.0785 (7)0.42727 (15)0.0391 (12)
H26A0.42310.11210.41380.059*
H26B0.50680.07850.45990.059*
H26C0.55340.16770.41830.059*
C270.6473 (4)0.1695 (7)0.43046 (15)0.0354 (11)
C290.1869 (3)0.1527 (6)0.33732 (16)0.0375 (12)
H29A0.17780.03580.35240.056*
H29B0.17440.13340.30490.056*
H29C0.13210.24190.34490.056*
C300.4877 (4)0.3646 (6)0.26344 (15)0.0360 (12)
H30A0.48450.46820.24260.054*
H30B0.54040.27190.25570.054*
H30C0.51360.40820.2940.054*
C310.1925 (3)0.1531 (7)0.20870 (15)0.0381 (12)
H31A0.14510.23880.22230.057*
H31B0.19890.0370.22530.057*
H31C0.15830.13010.17760.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.035 (2)0.147 (4)0.047 (2)0.002 (2)0.0088 (17)0.006 (3)
O20.050 (2)0.069 (3)0.055 (2)0.027 (2)0.0095 (17)0.024 (2)
O30.0346 (17)0.047 (2)0.040 (2)0.0084 (17)0.0035 (14)0.0043 (18)
C10.037 (3)0.113 (6)0.032 (3)0.007 (3)0.004 (2)0.007 (3)
C20.042 (3)0.106 (6)0.037 (3)0.022 (4)0.004 (2)0.018 (3)
C30.042 (3)0.075 (4)0.044 (3)0.014 (3)0.002 (2)0.013 (3)
C40.030 (2)0.060 (4)0.033 (3)0.007 (3)0.002 (2)0.005 (3)
C50.028 (2)0.050 (3)0.035 (3)0.009 (3)0.0026 (19)0.005 (3)
C60.048 (3)0.038 (3)0.046 (3)0.009 (3)0.003 (2)0.006 (3)
C70.038 (3)0.034 (3)0.039 (3)0.005 (2)0.003 (2)0.000 (2)
C80.027 (2)0.028 (3)0.035 (3)0.000 (2)0.0013 (18)0.004 (2)
C280.038 (3)0.045 (3)0.046 (3)0.001 (2)0.004 (2)0.002 (3)
C90.031 (2)0.028 (2)0.032 (2)0.000 (2)0.0060 (18)0.000 (2)
C100.033 (2)0.030 (3)0.036 (3)0.003 (2)0.0040 (19)0.003 (2)
C110.029 (2)0.031 (3)0.037 (3)0.001 (2)0.0012 (19)0.002 (2)
C120.039 (3)0.044 (3)0.036 (3)0.003 (2)0.007 (2)0.001 (3)
C130.034 (2)0.041 (3)0.035 (3)0.004 (2)0.008 (2)0.003 (2)
C140.029 (2)0.033 (3)0.036 (3)0.001 (2)0.005 (2)0.001 (2)
C150.037 (3)0.028 (3)0.038 (3)0.002 (2)0.007 (2)0.002 (2)
C160.033 (2)0.027 (3)0.042 (3)0.003 (2)0.005 (2)0.004 (2)
C170.028 (2)0.030 (3)0.033 (3)0.001 (2)0.0017 (19)0.002 (2)
C180.029 (2)0.034 (3)0.037 (3)0.001 (2)0.006 (2)0.005 (2)
C190.037 (3)0.042 (3)0.036 (3)0.004 (2)0.003 (2)0.003 (2)
C200.037 (3)0.054 (3)0.036 (3)0.007 (2)0.005 (2)0.006 (3)
C210.030 (2)0.065 (4)0.029 (3)0.007 (3)0.000 (2)0.006 (3)
C220.032 (3)0.089 (5)0.034 (3)0.006 (3)0.005 (2)0.001 (3)
C230.051 (3)0.097 (5)0.045 (4)0.010 (3)0.004 (3)0.010 (3)
C240.034 (3)0.098 (5)0.036 (3)0.004 (3)0.001 (2)0.006 (3)
C250.040 (3)0.057 (4)0.045 (3)0.007 (3)0.003 (2)0.011 (3)
C260.038 (3)0.043 (3)0.035 (3)0.005 (2)0.001 (2)0.003 (2)
C270.035 (3)0.036 (3)0.036 (3)0.001 (2)0.006 (2)0.001 (2)
C290.036 (2)0.031 (3)0.046 (3)0.000 (2)0.009 (2)0.001 (2)
C300.037 (3)0.035 (3)0.036 (3)0.004 (2)0.004 (2)0.004 (2)
C310.034 (2)0.042 (3)0.038 (3)0.000 (2)0.005 (2)0.007 (2)
Geometric parameters (Å, º) top
O1—C11.213 (7)C14—C151.527 (7)
O2—C271.197 (5)C14—C291.538 (6)
O3—C271.356 (5)C15—C161.518 (6)
O3—C281.456 (5)C15—H15A0.9900
C1—C21.486 (10)C15—H15B0.9900
C1—C221.534 (8)C16—C171.551 (6)
C2—C31.548 (7)C16—H16A0.9900
C2—H2A0.9900C16—H16B0.9900
C2—H2B0.9900C17—C301.555 (6)
C3—C41.548 (6)C17—C181.591 (6)
C3—H3A0.9900C18—C311.538 (6)
C3—H3B0.9900C18—C191.546 (7)
C4—C251.549 (7)C19—C201.546 (6)
C4—C211.562 (7)C19—H19A0.9900
C4—C51.580 (6)C19—H19B0.9900
C5—C61.552 (7)C20—C211.526 (7)
C5—C181.567 (6)C20—H20A0.9900
C5—H51.0000C20—H20B0.9900
C6—C71.504 (6)C21—C221.563 (7)
C6—H6A0.9900C21—H211.0000
C6—H6B0.9900C22—C231.529 (9)
C7—C81.331 (6)C22—C241.550 (7)
C7—H70.9500C23—H23A0.9800
C8—C91.521 (6)C23—H23B0.9800
C8—C171.536 (7)C23—H23C0.9800
C28—H28A0.9800C24—H24A0.9800
C28—H28B0.9800C24—H24B0.9800
C28—H28C0.9800C24—H24C0.9800
C9—C141.538 (6)C25—H25A0.9800
C9—C101.541 (6)C25—H25B0.9800
C9—H91.0000C25—H25C0.9800
C10—C111.532 (6)C26—H26A0.9800
C10—H10A0.9900C26—H26B0.9800
C10—H10B0.9900C26—H26C0.9800
C11—C271.512 (6)C29—H29A0.9800
C11—C261.541 (7)C29—H29B0.9800
C11—C121.543 (6)C29—H29C0.9800
C12—C131.531 (6)C30—H30A0.9800
C12—H12A0.9900C30—H30B0.9800
C12—H12B0.9900C30—H30C0.9800
C13—C141.543 (6)C31—H31A0.9800
C13—H13A0.9900C31—H31B0.9800
C13—H13B0.9900C31—H31C0.9800
O1···C1i3.296 (6)H12B···H15B2.3738
O1···C24i3.364 (6)H13A···H15A2.4124
O1···O1i3.095 (5)H13A···H29C2.5932
O1···C25ii3.374 (7)H13A···O3viii2.9083
O1···H23C2.5772H13A···C27viii3.0071
O1···H24Ai2.4926H13B···C262.7765
O1···H23A2.6848H13B···H26A2.2420
O1···H25Aii2.8513H13B···H29A2.2791
O2···H10B2.5074H13B···O2vii2.7366
O2···H12B2.9118H15A···H13A2.4124
O2···H28A2.6266H15A···H29C2.5242
O2···H28C2.5685H15A···H10Aviii2.5215
O2···H13Bii2.7366H15B···C102.8098
O2···H26Aii2.7463H15B···C122.8768
O2···H29Aii2.6483H15B···C302.8850
O3···H26B2.4499H15B···H10B2.2841
O3···H26C2.7834H15B···H12B2.3738
O3···H13Aiii2.9083H15B···H30C2.2217
O3···H28Civ2.5461H16A···C7vi3.0860
C1···O1i3.296 (6)H16A···C192.8258
C2···C23v3.573 (11)H16A···H7vi2.4188
C7···C313.169 (6)H16A···H19B2.5111
C10···C303.391 (6)H16A···H30A2.4498
C17···C293.571 (6)H16A···H30C2.5990
C23···C2vi3.573 (11)H16B···C193.0404
C24···O1i3.364 (6)H16B···C292.6892
C24···C253.288 (8)H16B···C312.5756
C25···C243.288 (8)H16B···H29B2.2122
C25···C313.246 (7)H16B···H31A1.9595
C25···O1vii3.374 (7)H19A···C163.0522
C29···C173.571 (6)H19A···C302.5882
C30···C103.391 (6)H19A···H6Avi2.5912
C31···C73.169 (6)H19A···H212.4122
C31···C253.246 (7)H19A···H30A1.9297
C2···H25A2.6487H19B···C162.7982
C2···H24C2.8347H19B···H16A2.5111
C3···H20Aiii3.0208H19B···H31A2.3648
C3···H6B2.7544H19B···H3Bviii2.5630
C4···H31C3.0008H20A···C243.0172
C4···H24C3.0538H20A···C252.6992
C5···H30B2.7741H20A···C312.9537
C6···H25C2.6992H20A···H24B2.5863
C6···H3A2.8016H20A···H25B2.0044
C6···H31B2.5859H20A···H31C2.3603
C7···H31B2.5953H20A···C3viii3.0208
C7···H10A3.0461H20A···H2Aviii2.4426
C7···H30B2.9993H20A···H3Bviii2.5287
C7···H16Av3.0860H20B···C232.6591
C8···H53.0662H20B···H23B2.1213
C8···H29B2.6833H21···C183.0702
C8···H31B2.6746H21···H3B2.5782
C9···H26A2.7537H21···H52.2513
C10···H30C2.8864H21···H19A2.4122
C10···H15B2.8098H21···H23A2.3388
C12···H15B2.8768H23A···O12.6848
C13···H26A2.7630H23A···H212.3388
C15···H10B2.8824H23B···C202.8080
C15···H12B2.9292H23B···H2Bvi2.5954
C15···H30C2.7675H23B···H20B2.1213
C16···H19B2.7982H23B···H24B2.4407
C16···H31A2.6943H23C···O12.5772
C16···H29B2.6953H23C···H24A2.4918
C16···H19A3.0522H23C···H23Ci2.5049
C17···H29B3.0706H24A···H23C2.4918
C18···H213.0702H24A···O1i2.4926
C19···H16A2.8258H24B···C202.8620
C19···H30A2.6707H24B···H20A2.5863
C19···H16B3.0404H24B···H23B2.4407
C20···H24B2.8620H24B···H2Aviii2.5250
C20···H23B2.8080H24C···C22.8347
C20···H31C2.8735H24C···C43.0538
C20···H3Bviii3.0612H24C···C252.6215
C20···H25B2.6510H24C···H2B2.2633
C23···H20B2.6591H24C···H25A2.1178
C24···H2B2.8097H24C···H25B2.5392
C24···H25A2.9595H25A···C22.6487
C24···H20A3.0172H25A···C242.9595
C25···H20A2.6992H25A···H2B2.0750
C25···H2B2.7895H25A···H3A2.5473
C25···H6A2.7449H25A···H24C2.1178
C25···H31C2.5809H25A···O1vii2.8513
C25···H24C2.6215H25B···C202.6510
C26···H92.7442H25B···C312.9481
C26···H13B2.7765H25B···H20A2.0044
C27···H13Aiii3.0071H25B···H24C2.5392
C28···H28Civ3.0212H25B···H31C2.0998
C29···H16B2.6892H25C···C62.6992
C29···H30Cvii2.8846H25C···C313.0409
C30···H10B2.7822H25C···H6A2.0411
C30···H52.5125H25C···H31C2.4892
C30···H29Bii3.0824H26A···C92.7537
C30···H15B2.8850H26A···C132.7630
C30···H19A2.5882H26A···H92.1654
C31···H6A2.8393H26A···H13B2.2420
C31···H16B2.5756H26A···O2vii2.7463
C31···H20A2.9537H26B···O32.4499
C31···H25B2.9481H26B···H12A2.5141
C31···H25C3.0409H26B···H26Bix2.4690
C31···H29B2.9695H26C···O32.7834
C31···H6Bviii3.0979H26C···H10A2.5419
H2A···H20Aiii2.4426H28A···O22.6266
H2A···H24Biii2.5250H28C···O22.5685
H2B···C242.8097H28C···O3x2.5461
H2B···C252.7895H28C···C28x3.0212
H2B···H23Bv2.5954H29A···H92.4101
H2B···H24C2.2633H29A···H13B2.2791
H2B···H25A2.0750H29A···O2vii2.6483
H3A···C62.8016H29A···H30Cvii2.5957
H3A···H6B2.3541H29B···C82.6833
H3A···H25A2.5473H29B···C162.6953
H3B···H52.2756H29B···C173.0706
H3B···H212.5782H29B···C312.9695
H3B···C20iii3.0612H29B···H16B2.2122
H3B···H19Biii2.5630H29B···H31A2.5922
H3B···H20Aiii2.5287H29B···H31B2.5811
H5···C83.0662H29B···C30vii3.0824
H5···C302.5125H29B···H30Cvii2.5122
H5···H3B2.2756H29C···H13A2.5932
H5···H212.2513H29C···H15A2.5242
H5···H30B2.0469H29C···H10Aviii2.2599
H6A···C252.7449H30A···C192.6707
H6A···C312.8393H30A···H16A2.4498
H6A···H19Av2.5912H30A···H19A1.9297
H6A···H25C2.0411H30B···C52.7741
H6A···H31B2.3127H30B···C72.9993
H6B···C32.7544H30B···H52.0469
H6B···H3A2.3541H30C···C102.8864
H6B···C31iii3.0979H30C···C152.7675
H6B···H31Aiii2.2837H30C···H10B2.0917
H7···H92.2470H30C···H15B2.2217
H7···H16Av2.4188H30C···H16A2.5990
H9···C262.7442H30C···C29ii2.8846
H9···H72.2470H30C···H29Aii2.5957
H9···H26A2.1654H30C···H29Bii2.5122
H9···H29A2.4101H31A···C162.6943
H10A···C73.0461H31A···H16B1.9595
H10A···H26C2.5419H31A···H19B2.3648
H10A···H15Aiii2.5215H31A···H29B2.5922
H10A···H29Ciii2.2599H31A···H6Bviii2.2837
H10B···O22.5074H31B···C62.5859
H10B···C152.8824H31B···C72.5953
H10B···C302.7822H31B···C82.6746
H10B···H12B2.5168H31B···H6A2.3127
H10B···H15B2.2841H31B···H29B2.5811
H10B···H30C2.0917H31C···C43.0008
H12A···H26B2.5141H31C···C202.8735
H12A···H12Aix2.5414H31C···C252.5809
H12B···O22.9118H31C···H20A2.3603
H12B···C152.9292H31C···H25B2.0998
H12B···H10B2.5168H31C···H25C2.4892
C27—O3—C28116.2 (3)C15—C16—C17114.1 (4)
O1—C1—C2122.2 (6)C15—C16—H16A108.7
O1—C1—C22122.1 (7)C17—C16—H16A108.7
C2—C1—C22115.6 (5)C15—C16—H16B108.7
C1—C2—C3109.0 (5)C17—C16—H16B108.7
C1—C2—H2A109.9H16A—C16—H16B107.6
C3—C2—H2A109.9C8—C17—C16111.9 (3)
C1—C2—H2B109.9C8—C17—C30106.6 (3)
C3—C2—H2B109.9C16—C17—C30106.1 (4)
H2A—C2—H2B108.3C8—C17—C18108.7 (4)
C4—C3—C2112.2 (4)C16—C17—C18110.7 (3)
C4—C3—H3A109.2C30—C17—C18112.7 (3)
C2—C3—H3A109.2C31—C18—C19107.8 (4)
C4—C3—H3B109.2C31—C18—C5110.4 (4)
C2—C3—H3B109.2C19—C18—C5109.9 (4)
H3A—C3—H3B107.9C31—C18—C17110.9 (3)
C3—C4—C25107.2 (4)C19—C18—C17109.9 (4)
C3—C4—C21108.9 (4)C5—C18—C17107.9 (3)
C25—C4—C21113.4 (4)C18—C19—C20114.7 (4)
C3—C4—C5107.8 (4)C18—C19—H19A108.6
C25—C4—C5113.8 (4)C20—C19—H19A108.6
C21—C4—C5105.5 (4)C18—C19—H19B108.6
C6—C5—C18109.1 (4)C20—C19—H19B108.6
C6—C5—C4113.9 (4)H19A—C19—H19B107.6
C18—C5—C4117.9 (4)C21—C20—C19110.8 (4)
C6—C5—H5104.9C21—C20—H20A109.5
C18—C5—H5104.9C19—C20—H20A109.5
C4—C5—H5104.9C21—C20—H20B109.5
C7—C6—C5113.8 (4)C19—C20—H20B109.5
C7—C6—H6A108.8H20A—C20—H20B108.1
C5—C6—H6A108.8C20—C21—C4109.8 (4)
C7—C6—H6B108.8C20—C21—C22114.9 (4)
C5—C6—H6B108.8C4—C21—C22118.1 (4)
H6A—C6—H6B107.7C20—C21—H21104.1
C8—C7—C6126.4 (5)C4—C21—H21104.1
C8—C7—H7116.8C22—C21—H21104.1
C6—C7—H7116.8C23—C22—C1109.0 (5)
C7—C8—C9118.9 (4)C23—C22—C24107.6 (5)
C7—C8—C17120.5 (4)C1—C22—C24110.0 (5)
C9—C8—C17120.5 (4)C23—C22—C21110.2 (5)
O3—C28—H28A109.5C1—C22—C21106.1 (4)
O3—C28—H28B109.5C24—C22—C21113.9 (4)
H28A—C28—H28B109.5C22—C23—H23A109.5
O3—C28—H28C109.5C22—C23—H23B109.5
H28A—C28—H28C109.5H23A—C23—H23B109.5
H28B—C28—H28C109.5C22—C23—H23C109.5
C8—C9—C14112.1 (3)H23A—C23—H23C109.5
C8—C9—C10111.4 (3)H23B—C23—H23C109.5
C14—C9—C10113.2 (4)C22—C24—H24A109.5
C8—C9—H9106.6C22—C24—H24B109.5
C14—C9—H9106.6H24A—C24—H24B109.5
C10—C9—H9106.6C22—C24—H24C109.5
C11—C10—C9113.4 (3)H24A—C24—H24C109.5
C11—C10—H10A108.9H24B—C24—H24C109.5
C9—C10—H10A108.9C4—C25—H25A109.5
C11—C10—H10B108.9C4—C25—H25B109.5
C9—C10—H10B108.9H25A—C25—H25B109.5
H10A—C10—H10B107.7C4—C25—H25C109.5
C27—C11—C10108.2 (3)H25A—C25—H25C109.5
C27—C11—C26111.0 (4)H25B—C25—H25C109.5
C10—C11—C26111.4 (4)C11—C26—H26A109.5
C27—C11—C12106.9 (4)C11—C26—H26B109.5
C10—C11—C12107.6 (4)H26A—C26—H26B109.5
C26—C11—C12111.5 (3)C11—C26—H26C109.5
C13—C12—C11111.5 (4)H26A—C26—H26C109.5
C13—C12—H12A109.3H26B—C26—H26C109.5
C11—C12—H12A109.3O2—C27—O3121.0 (4)
C13—C12—H12B109.3O2—C27—C11125.8 (4)
C11—C12—H12B109.3O3—C27—C11113.2 (4)
H12A—C12—H12B108.0C14—C29—H29A109.5
C12—C13—C14114.9 (3)C14—C29—H29B109.5
C12—C13—H13A108.5H29A—C29—H29B109.5
C14—C13—H13A108.5C14—C29—H29C109.5
C12—C13—H13B108.5H29A—C29—H29C109.5
C14—C13—H13B108.5H29B—C29—H29C109.5
H13A—C13—H13B107.5C17—C30—H30A109.5
C15—C14—C29111.0 (4)C17—C30—H30B109.5
C15—C14—C9108.9 (3)H30A—C30—H30B109.5
C29—C14—C9108.9 (4)C17—C30—H30C109.5
C15—C14—C13110.8 (4)H30A—C30—H30C109.5
C29—C14—C13107.0 (3)H30B—C30—H30C109.5
C9—C14—C13110.2 (4)C18—C31—H31A109.5
C16—C15—C14112.6 (4)C18—C31—H31B109.5
C16—C15—H15A109.1H31A—C31—H31B109.5
C14—C15—H15A109.1C18—C31—H31C109.5
C16—C15—H15B109.1H31A—C31—H31C109.5
C14—C15—H15B109.1H31B—C31—H31C109.5
H15A—C15—H15B107.8
O1—C1—C2—C3114.2 (5)C15—C16—C17—C3077.3 (4)
C22—C1—C2—C362.1 (6)C15—C16—C17—C18160.0 (4)
C1—C2—C3—C458.6 (6)C6—C5—C18—C3158.1 (5)
C2—C3—C4—C2571.8 (6)C4—C5—C18—C3173.8 (5)
C2—C3—C4—C2151.3 (6)C6—C5—C18—C19176.9 (4)
C2—C3—C4—C5165.3 (5)C4—C5—C18—C1945.0 (5)
C3—C4—C5—C660.1 (5)C6—C5—C18—C1763.3 (5)
C25—C4—C5—C658.7 (5)C4—C5—C18—C17164.9 (4)
C21—C4—C5—C6176.3 (4)C8—C17—C18—C3162.5 (4)
C3—C4—C5—C18170.3 (4)C16—C17—C18—C3160.8 (5)
C25—C4—C5—C1870.9 (6)C30—C17—C18—C31179.6 (4)
C21—C4—C5—C1854.0 (5)C8—C17—C18—C19178.4 (3)
C18—C5—C6—C737.2 (5)C16—C17—C18—C1958.3 (4)
C4—C5—C6—C7171.1 (3)C30—C17—C18—C1960.4 (4)
C5—C6—C7—C87.2 (7)C8—C17—C18—C558.6 (4)
C6—C7—C8—C9178.5 (4)C16—C17—C18—C5178.1 (4)
C6—C7—C8—C173.5 (7)C30—C17—C18—C559.4 (5)
C7—C8—C9—C14143.7 (4)C31—C18—C19—C2077.2 (5)
C17—C8—C9—C1441.2 (5)C5—C18—C19—C2043.2 (5)
C7—C8—C9—C1088.3 (5)C17—C18—C19—C20161.8 (3)
C17—C8—C9—C1086.8 (5)C18—C19—C20—C2154.9 (5)
C8—C9—C10—C11177.7 (4)C19—C20—C21—C464.6 (5)
C14—C9—C10—C1154.9 (5)C19—C20—C21—C22159.5 (4)
C9—C10—C11—C27173.0 (4)C3—C4—C21—C20177.1 (4)
C9—C10—C11—C2664.7 (5)C25—C4—C21—C2063.6 (5)
C9—C10—C11—C1257.8 (5)C5—C4—C21—C2061.5 (4)
C27—C11—C12—C13173.1 (4)C3—C4—C21—C2248.6 (5)
C10—C11—C12—C1357.1 (5)C25—C4—C21—C2270.7 (5)
C26—C11—C12—C1365.4 (5)C5—C4—C21—C22164.1 (3)
C11—C12—C13—C1455.3 (6)O1—C1—C22—C232.7 (7)
C8—C9—C14—C1552.7 (5)C2—C1—C22—C23173.6 (5)
C10—C9—C14—C1574.3 (4)O1—C1—C22—C24115.0 (6)
C8—C9—C14—C2968.5 (5)C2—C1—C22—C2468.6 (6)
C10—C9—C14—C29164.5 (4)O1—C1—C22—C21121.4 (5)
C8—C9—C14—C13174.5 (4)C2—C1—C22—C2155.0 (6)
C10—C9—C14—C1347.5 (5)C20—C21—C22—C2361.7 (5)
C12—C13—C14—C1571.8 (5)C4—C21—C22—C23166.2 (4)
C12—C13—C14—C29167.0 (4)C20—C21—C22—C1179.6 (5)
C12—C13—C14—C948.8 (6)C4—C21—C22—C148.3 (6)
C29—C14—C15—C1658.2 (5)C20—C21—C22—C2459.2 (7)
C9—C14—C15—C1661.7 (5)C4—C21—C22—C2472.9 (6)
C13—C14—C15—C16177.0 (3)C28—O3—C27—O21.4 (6)
C14—C15—C16—C1755.5 (5)C28—O3—C27—C11179.9 (4)
C7—C8—C17—C16151.9 (4)C10—C11—C27—O229.8 (6)
C9—C8—C17—C1633.1 (5)C26—C11—C27—O2152.4 (5)
C7—C8—C17—C3092.4 (5)C12—C11—C27—O285.8 (5)
C9—C8—C17—C3082.6 (4)C10—C11—C27—O3151.5 (4)
C7—C8—C17—C1829.3 (5)C26—C11—C27—O328.9 (5)
C9—C8—C17—C18155.7 (3)C12—C11—C27—O392.9 (4)
C15—C16—C17—C838.6 (5)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z; (iv) x+3/2, y1/2, z+1; (v) x, y1, z; (vi) x, y+1, z; (vii) x1/2, y1/2, z; (viii) x1/2, 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···AD—HH···AD···AD—H···A
C24—H24A···O1i0.982.493.364 (6)148
C28—H28C···O3x0.982.553.493 (6)162
C29—H29A···O2vii0.982.653.587 (6)160
Symmetry codes: (i) x+1, y, z; (vii) x1/2, y1/2, z; (x) x+3/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC31H48O3
Mr468.69
Crystal system, space groupMonoclinic, C2
Temperature (K)100
a, b, c (Å)12.0144 (4), 7.2750 (4), 30.364 (2)
β (°) 99.565 (2)
V3)2617.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.1 × 0.05 × 0.05
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4283, 2486, 1679
Rint0.049
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.159, 1.09
No. of reflections2486
No. of parameters315
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.26

Computer programs: COLLECT (Nonius BV, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
O1—C11.213 (7)O3—C271.356 (5)
O2—C271.197 (5)O3—C281.456 (5)
C27—O3—C28116.2 (3)O2—C27—O3121.0 (4)
O1—C1—C2122.2 (6)O2—C27—C11125.8 (4)
O1—C1—C22122.1 (7)O3—C27—C11113.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24A···O1i0.982.493.364 (6)148
C28—H28C···O3ii0.982.553.493 (6)162
C29—H29A···O2iii0.982.653.587 (6)160
Symmetry codes: (i) x+1, y, z; (ii) x+3/2, y+1/2, z+1; (iii) x1/2, y1/2, z.
 

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