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The title compounds, 2C30H46O8·CH3OH·H2O, (I), and C32H48O9, (II), respectively, are cardenolide glycosides which were isolated from the seeds of Cerbera odollam. There are two crystallographically independent cardenolide mol­ecules in (I), together with one methanol and one water solvate mol­ecule. In both (I) and (II), the steroid nuclei are in cis/trans/cis configurations, with the cyclo­pentane rings showing conformational flexibility, viz. an envelope conformation in (I) and a twisted conformation in (II). In both compounds, the lactone ring is nearly orthogonal to the cyclo­pentane ring. The packing of (I) is composed of molecular layers stabilized by five O-H...O hydrogen bonds. In the packing of (II), the mol­ecules are packed into columns by one O-H...O hydrogen bond, and are further interconnected into a three-dimensional network by one O-H...O and three C-H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102023065/ta1401sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102023065/ta1401Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102023065/ta1401IIsup3.hkl
Contains datablock II

CCDC references: 205306; 205307

Comment top

Cerbera odollam gearnth (Apocynaceae) are widely distributed in the South-East Asian and Indian Ocean regions. It has been reported that the leaves and fruits of this plant possess cadiotonic activity and have effects on the central nervous system (Chen & Steldt, 1942; Hien et al., 1991; Lasserre et al., 1992). We have isolated cerbinal from the bark of this plant and it exhibited moderate bioactivity against mycobacterium tuberculosis and breast-cancer cells from the preliminary testing (Laphookhieo, 2001). The compounds in this study, (I) and (II), were isolated from the seeds of cerbera odollam and showed the characteristics of cardinolide glycoside. Preliminary testing of these componds show that both compounds have strong activities against human breast-cancer cells, human small cells lung cancer and oral human epidermoid carcinoma. As part of these studies, we have undertaken the X-ray crystal structure analyses of compounds (I) and (II) in order to establish their molecular structures.

The bond lengths and angles in (I) and (II) show normal values (Allen et al., 1987). In both compounds, the steroid nucleus has a cis/trans/cis conformation for the A—B/B—C/C—D rings. In all cases, the cylohexane A, B and C rings have a standard chair conformation, whereas the cyclopentane D ring shows some conformational flexibility. Attempted refinement of a Flack (1983) parameter was unsuccessful so the absolute configurations could not be determined.

In the crystal structure of (I) (Fig. 1), there are two crystallographically independent molecules, (IA) and (IB), in the asymmetric unit having chiralities, bond lengths and angles which agree with each other. Molecules (IA) and (IB) are related by a local rotation axis.

In molecules (IA) and (IB), the cyclopentane D ring (C13–C17) adopts an envelope conformation, with atom C14 displaced from the C13/C15/C16/C17 plane by 0.586 (8) and 0.605 (4) Å in molecules (IA) and (IB), respectively. The lactone ring (O1/C20—C23) attached at atom C17 is essentially planar, which is mainly due to the conjugation of CC and CO bonds. This ring is approximately orthogonal to the mean plane of the D ring, corresponding to a dihedral angle of 83.2 (3)° in molecule (IA) and 88.3 (4)° in molecule (IB). The orientation of the lactone is also determined by the torsion angle of C13—C17—C20—C22; that is −101.7 (7) in molecule (IA) and −107.8 (7)° in molecule (IB).

The relative orientations of the glycosidic linkage (O3/C24—C28) is determined by C2—C3—O2—C24 (ϕ1) and C3—O2—C24—C25 (ϕ2) torsion angles; ϕ1 and ϕ2 are 159.6 (4) and 173.1 (4)°, respectively, in molecule (IA), and 156.6 (4) and 173.2 (4)° in molecule (IB).

In the crystal of (I), there are one methanol and one water molecule solvate molecule which are incorporated during the recrystallization. Within the asymmetric unit, both the water and the methanol solvate molecules are linked to molecule (IA) by O5A—H5AA···O1W and O9—H9AA···O4A hydrogen bonds, while molecules (IA) and (IB) are interconnected almost symmetrically by O8A—H8AA···O7B and O8B—H8BB···O7A hydrogen bonds. In the packing, there are five O—H···O hydrogen bonds [O6A—H6AA···O4Ai, O5B—H5BB···O5Aii, O6B—H6BB···O4Biii, O1W—H1W1···O9iv and O1W—H2W1···O6Bv; see Table 2 for symmetry codes] interconnecting the molecules into molecular ribbons perpendicular to the c direction (Fig. 2).

In compound (II) (Fig. 3), the cyclopentane D ring adopts a twisted conformation, with atoms C13 and C14 displaced on opposite sides of the C15/C16/C17 plane by 0.294 (2) and 0.339 (2) Å, respectively. The planar lactone ring is also nearly orthogonal to the D ring, with a dihedral angle of 85.2 (1)°. The C13—C17—C20—C22 torsion angle is −96.6 (3)°. The ϕ1 and ϕ2 values are 96.7 (2) and 158.4 (2)°, respectively, which are much smaller than those in compound (I).

In the packing of compound (II), the molecules are linked by O8—H8A···O9ii hydrogen bonds into columns parallel to the a direction. Two adjacent molecular columns are interconnected by O5—H5A···O8i, C25—H25···O5iv and C32—H32B···O4iv hydrogen bonds (Fig. 4), and are further interconnected by C3—H3···O4iii into a three-dimensional network.

Experimental top

Fresh seeds (940 g) of cerbera odollam were extracted twice with methylene chloride (2.5 l), over a period of 5 d each at room temperature. The mixture was filtered and concentrated under reduced pressure. Some white solids (0.3085 g) which precipitated were filtered and purified by PLC (define) using 2% methanol in ether as eluant to yield two compounds, viz. (I) (RF = 0.19, 30% acetone–hexane) and (II) (RF = 0.38, 30% acetone–hexane). Both compounds recrystallized from chloroform/methanol as colorless slab-shaped single crystals. The melting points of (I) and (II) are 475 479 and 493–497 K, respectively.

Computing details top

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Packing diagram of compound (I), showing the molecular ribbons. H atoms have been omitted, except for those involved in hydrogen-bond interactions (dashed lines).
[Figure 3] Fig. 3. The structure of compound (II), showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
[Figure 4] Fig. 4. Packing diagram of compound (II), showing the interconnections of two adjacent molecular columns. H atoms have been omitted, except for those involved in hydrogen-bond interactions (dashed lines).
(I) 3β-o-(L-thevetoyl)-14β-hydroxy-5β-card-20 (22)-enolide methanol solvate monohydrate top
Crystal data top
2C30H46O8·CH4O·H2OZ = 1
Mr = 1119.39F(000) = 608
Triclinic, P1Dx = 1.250 Mg m3
a = 10.4353 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4491 (5) ÅCell parameters from 7201 reflections
c = 14.8760 (7) Åθ = 1.4–29.5°
α = 92.412 (1)°µ = 0.09 mm1
β = 101.471 (1)°T = 213 K
γ = 109.599 (1)°Slab, colorless
V = 1487.1 (1) Å30.44 × 0.32 × 0.10 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
6292 independent reflections
Radiation source: fine-focus sealed tube4368 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
Detector resolution: 8.33 pixels mm-1θmax = 27.0°, θmin = 1.4°
ω scansh = 1213
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1013
Tmin = 0.961, Tmax = 0.991l = 1812
9863 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0841P)2]
where P = (Fo2 + 2Fc2)/3
6292 reflections(Δ/σ)max < 0.001
715 parametersΔρmax = 0.68 e Å3
3 restraintsΔρmin = 0.70 e Å3
Crystal data top
2C30H46O8·CH4O·H2Oγ = 109.599 (1)°
Mr = 1119.39V = 1487.1 (1) Å3
Triclinic, P1Z = 1
a = 10.4353 (5) ÅMo Kα radiation
b = 10.4491 (5) ŵ = 0.09 mm1
c = 14.8760 (7) ÅT = 213 K
α = 92.412 (1)°0.44 × 0.32 × 0.10 mm
β = 101.471 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
6292 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
4368 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.991Rint = 0.072
9863 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0663 restraints
wR(F2) = 0.182H-atom parameters constrained
S = 0.97Δρmax = 0.68 e Å3
6292 reflectionsΔρmin = 0.70 e Å3
715 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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.

All H atoms in (I) and (II) were fixed geometrically with ideal bond lengths and angles, and were treated as riding atoms with displacement parameters Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O). Due to a large fraction of weak data at higher angles, the 2θ maximum is limited to 54°.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A2.0161 (5)0.3352 (5)1.3098 (3)0.0426 (12)
O2A1.2261 (3)0.2619 (3)1.0060 (2)0.0185 (8)
O3A0.9814 (3)0.1861 (4)0.9698 (3)0.0220 (8)
O4A2.1558 (7)0.3886 (7)1.2351 (4)0.0759 (14)
O5A1.7495 (3)0.0856 (3)1.2920 (2)0.0169 (7)
H5AA1.70640.07471.33040.025*
O6A1.2410 (4)0.5050 (4)1.0947 (3)0.0315 (10)
H6AA1.22630.54141.13960.047*
O7A1.0606 (4)0.5924 (4)0.9477 (3)0.0299 (9)
O8A0.9493 (4)0.3986 (4)0.7860 (3)0.0326 (10)
H8AA0.94370.47500.78530.049*
C1A1.4814 (6)0.2168 (6)0.9897 (4)0.0234 (12)
H1A1.48050.30940.99090.028*
H1B1.54140.20850.94930.028*
C2A1.3339 (6)0.1181 (6)0.9484 (4)0.0258 (12)
H2A1.33430.02550.94200.031*
H2B1.30100.14020.88740.031*
C3A1.2356 (5)0.1267 (5)1.0097 (4)0.0206 (11)
H3A1.14310.05720.98490.025*
C4A1.2910 (5)0.1038 (5)1.1081 (4)0.0192 (11)
H4A1.28660.00971.10850.023*
H4B1.23090.11781.14670.023*
C5A1.4434 (5)0.2000 (5)1.1503 (4)0.0189 (11)
H5A1.44250.29351.15440.023*
C6A1.4930 (6)0.1722 (6)1.2486 (4)0.0222 (11)
H6A1.42160.16661.28280.027*
H6B1.57660.24791.27890.027*
C7A1.5243 (5)0.0396 (5)1.2506 (4)0.0205 (11)
H7A1.43780.03721.22850.025*
H7B1.56280.03011.31380.025*
C8A1.6278 (5)0.0347 (5)1.1909 (4)0.0169 (10)
H8A1.71420.11261.21560.020*
C9A1.5715 (5)0.0574 (5)1.0911 (4)0.0166 (10)
H9A1.48000.01501.06920.020*
C10A1.5455 (5)0.1952 (5)1.0880 (4)0.0169 (10)
C11A1.6624 (6)0.0387 (6)1.0275 (4)0.0251 (12)
H11A1.75150.11341.04330.030*
H11B1.61780.04230.96430.030*
C12A1.6873 (6)0.0972 (6)1.0339 (4)0.0220 (11)
H12B1.74650.10330.99250.026*
H12A1.59850.17151.01290.026*
C13A1.7556 (5)0.1159 (5)1.1317 (3)0.0161 (10)
C14A1.6652 (5)0.0956 (5)1.1996 (3)0.0134 (10)
C15A1.5415 (5)0.2312 (5)1.1799 (4)0.0184 (10)
H15A1.49760.24681.23210.022*
H15B1.47240.23061.12570.022*
C16A1.6026 (5)0.3418 (5)1.1634 (4)0.0250 (12)
H16A1.53740.41381.11630.030*
H16B1.62240.38181.21980.030*
C27A0.9609 (5)0.3633 (6)0.8770 (4)0.0205 (11)
H27A0.87680.36080.89780.025*
C28A0.9726 (5)0.2223 (6)0.8777 (4)0.0232 (11)
H28A1.05690.22400.85740.028*
C29A0.8465 (7)0.1119 (6)0.8178 (5)0.0379 (15)
H29A0.85720.02470.82320.057*
H29B0.83820.13010.75460.057*
H29C0.76400.11100.83750.057*
C30A1.1829 (8)0.7144 (7)0.9615 (7)0.059 (2)
H30A1.15500.79290.95550.088*
H30B1.23510.70890.91600.088*
H30C1.24000.72261.02210.088*
C17A1.7390 (5)0.2706 (5)1.1312 (4)0.0184 (10)
H17A1.72410.30771.06680.022*
C18A1.9056 (5)0.0168 (5)1.1586 (4)0.0229 (12)
H18A1.95050.01951.10850.034*
H18B1.95470.04261.21230.034*
H18C1.90630.07421.17190.034*
C19A1.6830 (6)0.3179 (5)1.1217 (5)0.0303 (13)
H19A1.66390.40151.11870.045*
H19B1.74630.31671.08310.045*
H19C1.72450.31181.18430.045*
C20A1.8615 (5)0.2999 (5)1.1857 (4)0.0181 (10)
C21A1.8942 (7)0.2997 (7)1.2870 (4)0.0362 (15)
H21A1.91110.20991.31770.043*
H21B1.81710.36581.30620.043*
C22A1.9578 (6)0.3324 (7)1.1527 (5)0.0389 (16)
H22A1.96270.33961.09100.047*
C23A2.0553 (7)0.3551 (7)1.2317 (6)0.0453 (19)
C24A1.1064 (5)0.2701 (5)1.0319 (4)0.0188 (11)
H24A1.10550.23981.09330.023*
C25A1.1127 (5)0.4190 (5)1.0378 (4)0.0194 (11)
H25A1.03790.42431.06680.023*
C26A1.0884 (5)0.4656 (5)0.9435 (4)0.0188 (11)
H26A1.17120.47910.91810.023*
O1B0.2081 (5)1.4189 (5)0.3855 (3)0.0403 (11)
O2B0.5356 (3)0.7835 (3)0.6799 (3)0.0191 (8)
O3B0.4774 (4)0.5622 (4)0.7218 (3)0.0216 (8)
O4B0.2250 (8)1.5955 (7)0.4611 (4)0.0759 (14)
O5B0.0242 (4)1.1472 (4)0.4041 (2)0.0213 (8)
H5BB0.04681.08370.37830.032*
O6B0.7317 (4)0.7457 (4)0.5927 (3)0.0291 (9)
H6BB0.74780.70560.55020.044*
O7B0.8950 (4)0.6504 (4)0.7430 (3)0.0281 (9)
O8B0.7876 (4)0.6316 (4)0.9060 (3)0.0317 (10)
H8BB0.85990.61560.90870.048*
C1B0.5004 (5)1.0491 (6)0.6986 (4)0.0285 (13)
H1C0.59201.04730.69630.034*
H1D0.51381.12870.74030.034*
C2B0.4221 (6)0.9221 (6)0.7372 (4)0.0265 (13)
H2C0.33240.92540.74320.032*
H2D0.47460.91900.79820.032*
C3B0.3996 (5)0.7938 (5)0.6748 (4)0.0210 (11)
H3B0.34040.71380.69790.025*
C4B0.3288 (5)0.8023 (5)0.5762 (4)0.0196 (11)
H4C0.23360.79630.57480.024*
H4D0.32470.72420.53660.024*
C5B0.4025 (5)0.9334 (5)0.5370 (4)0.0217 (11)
H5B0.49460.93220.53270.026*
C6B0.3249 (6)0.9373 (7)0.4401 (4)0.0280 (13)
H6C0.30560.85150.40300.034*
H6D0.38401.01000.41240.034*
C7B0.1862 (6)0.9609 (6)0.4387 (4)0.0246 (12)
H7C0.14370.96840.37590.029*
H7D0.12250.88290.45940.029*
C8B0.2095 (5)1.0912 (5)0.5010 (4)0.0179 (10)
H8B0.27151.16780.47670.022*
C9B0.2878 (5)1.0856 (5)0.6007 (4)0.0185 (10)
H9B0.22871.00550.62370.022*
C10B0.4269 (5)1.0650 (5)0.6015 (4)0.0232 (12)
C11B0.3038 (6)1.2124 (6)0.6648 (4)0.0254 (12)
H11C0.34441.20310.72760.031*
H11D0.36721.29310.64640.031*
C12B0.1638 (5)1.2313 (5)0.6618 (4)0.0207 (11)
H12C0.17891.31240.70270.025*
H12D0.10251.15330.68410.025*
C13B0.0926 (5)1.2455 (5)0.5635 (4)0.0160 (10)
C14B0.0740 (5)1.1187 (5)0.4973 (4)0.0155 (10)
C15B0.0457 (5)1.0058 (5)0.5225 (4)0.0188 (10)
H15C0.01260.96940.57780.023*
H15D0.09000.93180.47250.023*
C16B0.1481 (5)1.0768 (5)0.5393 (4)0.0214 (11)
H16D0.19281.03870.58830.026*
H16C0.21981.06370.48360.026*
C17B0.0615 (5)1.2327 (5)0.5674 (4)0.0175 (10)
H17B0.06211.25520.63190.021*
C18B0.1757 (6)1.3818 (5)0.5347 (4)0.0253 (12)
H18D0.27051.38720.53930.038*
H18E0.17421.45570.57460.038*
H18F0.13461.38820.47210.038*
C19B0.5302 (6)1.1889 (6)0.5691 (6)0.0438 (18)
H19D0.61581.17300.56980.066*
H19E0.54891.26990.60990.066*
H19F0.49001.20070.50750.066*
C20B0.1154 (5)1.3242 (5)0.5121 (4)0.0217 (12)
C21B0.1601 (8)1.3080 (7)0.4073 (5)0.0450 (19)
H21D0.08201.31300.37980.054*
H21C0.23441.22080.38470.054*
C22B0.1371 (7)1.4347 (6)0.5417 (5)0.0360 (15)
H22B0.11811.46970.60340.043*
C23B0.1954 (8)1.4940 (8)0.4631 (5)0.047 (2)
C24B0.5289 (5)0.6500 (5)0.6571 (4)0.0182 (10)
H24B0.46640.61470.59610.022*
C25B0.6755 (6)0.6506 (5)0.6528 (4)0.0204 (11)
H25B0.66540.55930.62640.024*
C26B0.7710 (5)0.6802 (5)0.7465 (4)0.0195 (11)
H26B0.79680.77670.76980.023*
C27B0.7020 (5)0.5895 (5)0.8143 (4)0.0193 (11)
H27B0.68800.49380.79570.023*
C28B0.5644 (5)0.6042 (5)0.8149 (4)0.0202 (11)
H28B0.57850.69980.83390.024*
C29B0.4848 (7)0.5131 (7)0.8759 (5)0.0406 (16)
H29D0.39430.52060.86890.061*
H29E0.53490.54050.93910.061*
H29F0.47450.42000.85860.061*
C30B1.0100 (7)0.7617 (8)0.7294 (7)0.059 (2)
H30D1.08230.72900.71920.089*
H30E1.04530.82810.78310.089*
H30F0.98040.80310.67660.089*
C312.3709 (10)0.5541 (9)1.3384 (6)0.062 (2)
H31A2.33810.62411.37670.093*
H31B2.46720.53841.33920.093*
H31C2.31640.58281.27620.093*
O92.3575 (5)0.4312 (5)1.3724 (4)0.0484 (12)
H9AA2.30440.40331.32820.073*
O1W1.5908 (4)0.1956 (4)1.4173 (3)0.0291 (9)
H1W11.53420.27781.40740.044*
H2W11.63500.18111.47340.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.040 (3)0.049 (3)0.038 (3)0.024 (2)0.004 (2)0.000 (2)
O2A0.0129 (16)0.0214 (18)0.0220 (19)0.0071 (14)0.0033 (15)0.0046 (16)
O3A0.0135 (17)0.0221 (19)0.023 (2)0.0012 (15)0.0012 (15)0.0052 (16)
O4A0.112 (4)0.101 (3)0.057 (3)0.089 (3)0.024 (3)0.007 (2)
O5A0.0126 (16)0.0232 (18)0.0130 (17)0.0064 (14)0.0013 (14)0.0001 (15)
O6A0.0195 (19)0.035 (2)0.029 (2)0.0093 (17)0.0141 (17)0.0133 (19)
O7A0.025 (2)0.0203 (19)0.039 (2)0.0074 (16)0.0040 (18)0.0028 (18)
O8A0.045 (3)0.035 (2)0.018 (2)0.020 (2)0.0017 (19)0.0039 (18)
C1A0.028 (3)0.027 (3)0.023 (3)0.017 (2)0.007 (2)0.012 (2)
C2A0.035 (3)0.031 (3)0.015 (3)0.019 (3)0.001 (2)0.002 (2)
C3A0.019 (2)0.020 (3)0.023 (3)0.012 (2)0.002 (2)0.004 (2)
C4A0.015 (2)0.020 (3)0.024 (3)0.008 (2)0.001 (2)0.007 (2)
C5A0.019 (2)0.018 (2)0.021 (3)0.009 (2)0.003 (2)0.003 (2)
C6A0.024 (3)0.031 (3)0.018 (3)0.019 (2)0.003 (2)0.002 (2)
C7A0.023 (3)0.029 (3)0.016 (3)0.017 (2)0.003 (2)0.006 (2)
C8A0.018 (2)0.014 (2)0.017 (3)0.003 (2)0.006 (2)0.002 (2)
C9A0.013 (2)0.018 (2)0.019 (3)0.0062 (19)0.002 (2)0.005 (2)
C10A0.013 (2)0.015 (2)0.024 (3)0.007 (2)0.003 (2)0.009 (2)
C11A0.035 (3)0.034 (3)0.016 (3)0.019 (3)0.013 (2)0.010 (2)
C12A0.025 (3)0.030 (3)0.016 (3)0.016 (2)0.006 (2)0.005 (2)
C13A0.018 (2)0.015 (2)0.016 (2)0.006 (2)0.005 (2)0.002 (2)
C14A0.013 (2)0.017 (2)0.011 (2)0.008 (2)0.0010 (19)0.006 (2)
C15A0.012 (2)0.017 (2)0.023 (3)0.003 (2)0.001 (2)0.003 (2)
C16A0.012 (2)0.018 (3)0.040 (3)0.002 (2)0.002 (2)0.001 (2)
C27A0.015 (2)0.029 (3)0.015 (3)0.008 (2)0.002 (2)0.004 (2)
C28A0.014 (2)0.029 (3)0.022 (3)0.005 (2)0.003 (2)0.001 (2)
C29A0.034 (3)0.029 (3)0.035 (4)0.000 (3)0.005 (3)0.004 (3)
C30A0.045 (4)0.022 (3)0.090 (7)0.006 (3)0.000 (4)0.006 (4)
C17A0.018 (2)0.020 (3)0.017 (3)0.007 (2)0.002 (2)0.000 (2)
C18A0.016 (2)0.023 (3)0.028 (3)0.004 (2)0.008 (2)0.001 (2)
C19A0.018 (3)0.020 (3)0.049 (4)0.003 (2)0.004 (3)0.005 (3)
C20A0.018 (2)0.013 (2)0.020 (3)0.0045 (19)0.001 (2)0.001 (2)
C21A0.034 (3)0.048 (4)0.028 (3)0.019 (3)0.002 (3)0.015 (3)
C22A0.033 (3)0.052 (4)0.034 (4)0.026 (3)0.003 (3)0.017 (3)
C23A0.030 (3)0.037 (4)0.062 (5)0.026 (3)0.022 (3)0.019 (3)
C24A0.011 (2)0.027 (3)0.017 (3)0.007 (2)0.001 (2)0.006 (2)
C25A0.013 (2)0.026 (3)0.016 (3)0.006 (2)0.004 (2)0.003 (2)
C26A0.015 (2)0.019 (3)0.023 (3)0.010 (2)0.000 (2)0.004 (2)
O1B0.045 (3)0.038 (2)0.040 (3)0.021 (2)0.002 (2)0.010 (2)
O2B0.0135 (16)0.0148 (17)0.027 (2)0.0057 (14)0.0009 (15)0.0028 (15)
O3B0.0183 (17)0.0172 (17)0.025 (2)0.0028 (15)0.0000 (16)0.0060 (16)
O4B0.112 (4)0.101 (3)0.057 (3)0.089 (3)0.024 (3)0.007 (2)
O5B0.0225 (18)0.0238 (19)0.0169 (19)0.0101 (16)0.0010 (15)0.0043 (16)
O6B0.033 (2)0.030 (2)0.028 (2)0.0107 (18)0.0134 (18)0.0148 (18)
O7B0.0199 (19)0.033 (2)0.036 (2)0.0126 (17)0.0073 (17)0.0139 (19)
O8B0.031 (2)0.050 (3)0.018 (2)0.023 (2)0.0019 (17)0.0032 (19)
C1B0.011 (2)0.025 (3)0.042 (4)0.009 (2)0.012 (2)0.012 (3)
C2B0.026 (3)0.037 (3)0.020 (3)0.023 (3)0.006 (2)0.003 (2)
C3B0.018 (2)0.021 (3)0.025 (3)0.008 (2)0.005 (2)0.004 (2)
C4B0.015 (2)0.019 (3)0.024 (3)0.008 (2)0.001 (2)0.001 (2)
C5B0.016 (2)0.023 (3)0.028 (3)0.009 (2)0.006 (2)0.004 (2)
C6B0.036 (3)0.042 (3)0.022 (3)0.028 (3)0.014 (3)0.010 (3)
C7B0.034 (3)0.034 (3)0.016 (3)0.027 (3)0.001 (2)0.001 (2)
C8B0.018 (2)0.017 (2)0.021 (3)0.009 (2)0.006 (2)0.004 (2)
C9B0.014 (2)0.016 (2)0.024 (3)0.0039 (19)0.003 (2)0.001 (2)
C10B0.016 (2)0.020 (3)0.033 (3)0.007 (2)0.003 (2)0.002 (2)
C11B0.018 (3)0.024 (3)0.028 (3)0.008 (2)0.008 (2)0.008 (2)
C12B0.021 (3)0.019 (3)0.019 (3)0.009 (2)0.003 (2)0.004 (2)
C13B0.013 (2)0.013 (2)0.021 (3)0.0044 (19)0.002 (2)0.002 (2)
C14B0.017 (2)0.015 (2)0.015 (2)0.008 (2)0.001 (2)0.003 (2)
C15B0.017 (2)0.016 (2)0.019 (3)0.002 (2)0.001 (2)0.000 (2)
C16B0.015 (2)0.014 (2)0.033 (3)0.001 (2)0.007 (2)0.002 (2)
C17B0.016 (2)0.016 (2)0.019 (3)0.004 (2)0.005 (2)0.000 (2)
C18B0.020 (3)0.015 (3)0.038 (3)0.002 (2)0.007 (2)0.002 (2)
C19B0.021 (3)0.028 (3)0.084 (6)0.005 (2)0.020 (3)0.014 (4)
C20B0.011 (2)0.018 (3)0.035 (3)0.004 (2)0.004 (2)0.004 (2)
C21B0.051 (4)0.034 (4)0.042 (4)0.023 (3)0.022 (3)0.004 (3)
C22B0.053 (4)0.033 (3)0.040 (4)0.027 (3)0.029 (3)0.014 (3)
C23B0.072 (5)0.049 (4)0.058 (5)0.049 (4)0.046 (4)0.036 (4)
C24B0.021 (2)0.013 (2)0.018 (3)0.007 (2)0.002 (2)0.004 (2)
C25B0.029 (3)0.015 (2)0.022 (3)0.010 (2)0.010 (2)0.007 (2)
C26B0.016 (2)0.017 (2)0.028 (3)0.007 (2)0.005 (2)0.006 (2)
C27B0.021 (2)0.021 (3)0.016 (3)0.009 (2)0.002 (2)0.001 (2)
C28B0.016 (2)0.019 (3)0.023 (3)0.002 (2)0.004 (2)0.004 (2)
C29B0.043 (4)0.040 (4)0.041 (4)0.010 (3)0.020 (3)0.021 (3)
C30B0.023 (3)0.066 (5)0.088 (6)0.008 (3)0.017 (4)0.046 (5)
C310.085 (6)0.059 (5)0.058 (5)0.042 (5)0.020 (5)0.012 (4)
O90.038 (3)0.044 (3)0.056 (3)0.011 (2)0.000 (2)0.003 (2)
O1W0.029 (2)0.033 (2)0.023 (2)0.0081 (18)0.0046 (17)0.0064 (18)
Geometric parameters (Å, º) top
O1A—C23A1.336 (10)O3B—C24B1.416 (6)
O1A—C21A1.423 (7)O3B—C28B1.454 (6)
O2A—C24A1.405 (6)O4B—C23B1.200 (8)
O2A—C3A1.452 (6)O5B—C14B1.461 (6)
O3A—C24A1.418 (6)O5B—H5BB0.8200
O3A—C28A1.430 (6)O6B—C25B1.422 (6)
O4A—C23A1.204 (8)O6B—H6BB0.8200
O5A—C14A1.456 (5)O7B—C30B1.419 (8)
O5A—H5AA0.8200O7B—C26B1.439 (6)
O6A—C25A1.412 (6)O8B—C27B1.433 (6)
O6A—H6AA0.8200O8B—H8BB0.8200
O7A—C30A1.442 (8)C1B—C2B1.512 (9)
O7A—C26A1.449 (6)C1B—C10B1.538 (8)
O8A—C27A1.410 (6)C1B—H1C0.9700
O8A—H8AA0.8200C1B—H1D0.9700
C1A—C2A1.522 (8)C2B—C3B1.520 (8)
C1A—C10A1.542 (7)C2B—H2C0.9700
C1A—H1A0.9700C2B—H2D0.9700
C1A—H1B0.9700C3B—C4B1.526 (7)
C2A—C3A1.523 (8)C3B—H3B0.9800
C2A—H2A0.9700C4B—C5B1.532 (7)
C2A—H2B0.9700C4B—H4C0.9700
C3A—C4A1.522 (7)C4B—H4D0.9700
C3A—H3A0.9800C5B—C6B1.515 (7)
C4A—C5A1.553 (7)C5B—C10B1.561 (8)
C4A—H4A0.9700C5B—H5B0.9800
C4A—H4B0.9700C6B—C7B1.544 (7)
C5A—C6A1.525 (7)C6B—H6C0.9700
C5A—C10A1.557 (7)C6B—H6D0.9700
C5A—H5A0.9800C7B—C8B1.535 (7)
C6A—C7A1.527 (7)C7B—H7C0.9700
C6A—H6A0.9700C7B—H7D0.9700
C6A—H6B0.9700C8B—C14B1.525 (7)
C7A—C8A1.540 (7)C8B—C9B1.558 (7)
C7A—H7A0.9700C8B—H8B0.9800
C7A—H7B0.9700C9B—C10B1.534 (7)
C8A—C14A1.541 (6)C9B—C11B1.541 (7)
C8A—C9A1.543 (7)C9B—H9B0.9800
C8A—H8A0.9800C10B—C19B1.548 (8)
C9A—C11A1.517 (7)C11B—C12B1.531 (7)
C9A—C10A1.553 (7)C11B—H11C0.9700
C9A—H9A0.9800C11B—H11D0.9700
C10A—C19A1.543 (7)C12B—C13B1.541 (7)
C11A—C12A1.530 (7)C12B—H12C0.9700
C11A—H11A0.9700C12B—H12D0.9700
C11A—H11B0.9700C13B—C18B1.527 (7)
C12A—C13A1.539 (7)C13B—C14B1.552 (7)
C12A—H12B0.9700C13B—C17B1.581 (7)
C12A—H12A0.9700C14B—C15B1.526 (7)
C13A—C18A1.520 (7)C15B—C16B1.541 (7)
C13A—C14A1.566 (7)C15B—H15C0.9700
C13A—C17A1.567 (7)C15B—H15D0.9700
C14A—C15A1.531 (7)C16B—C17B1.565 (7)
C15A—C16A1.529 (7)C16B—H16D0.9700
C15A—H15A0.9700C16B—H16C0.9700
C15A—H15B0.9700C17B—C20B1.467 (7)
C16A—C17A1.549 (7)C17B—H17B0.9800
C16A—H16A0.9700C18B—H18D0.9600
C16A—H16B0.9700C18B—H18E0.9600
C27A—C28A1.519 (7)C18B—H18F0.9600
C27A—C26A1.525 (7)C19B—H19D0.9600
C27A—H27A0.9800C19B—H19E0.9600
C28A—C29A1.512 (8)C19B—H19F0.9600
C28A—H28A0.9800C20B—C22B1.323 (8)
C29A—H29A0.9600C20B—C21B1.520 (9)
C29A—H29B0.9600C21B—H21D0.9700
C29A—H29C0.9600C21B—H21C0.9700
C30A—H30A0.9600C22B—C23B1.467 (9)
C30A—H30B0.9600C22B—H22B0.9300
C30A—H30C0.9600C24B—C25B1.542 (7)
C17A—C20A1.502 (7)C24B—H24B0.9800
C17A—H17A0.9800C25B—C26B1.495 (7)
C18A—H18A0.9600C25B—H25B0.9800
C18A—H18B0.9600C26B—C27B1.531 (7)
C18A—H18C0.9600C26B—H26B0.9800
C19A—H19A0.9600C27B—C28B1.496 (7)
C19A—H19B0.9600C27B—H27B0.9800
C19A—H19C0.9600C28B—C29B1.504 (8)
C20A—C22A1.333 (8)C28B—H28B0.9800
C20A—C21A1.478 (8)C29B—H29D0.9600
C21A—H21A0.9700C29B—H29E0.9600
C21A—H21B0.9700C29B—H29F0.9600
C22A—C23A1.478 (9)C30B—H30D0.9600
C22A—H22A0.9300C30B—H30E0.9600
C24A—C25A1.533 (7)C30B—H30F0.9600
C24A—H24A0.9800C31—O91.421 (9)
C25A—C26A1.505 (7)C31—H31A0.9600
C25A—H25A0.9800C31—H31B0.9600
C26A—H26A0.9800C31—H31C0.9600
O1B—C23B1.327 (9)O9—H9AA0.8967
O1B—C21B1.434 (7)O1W—H1W10.8500
O2B—C24B1.398 (6)O1W—H2W10.8500
O2B—C3B1.446 (6)
C23A—O1A—C21A108.3 (5)C25B—O6B—H6BB109.5
C24A—O2A—C3A112.8 (4)C30B—O7B—C26B115.7 (5)
C24A—O3A—C28A112.7 (4)C27B—O8B—H8BB109.5
C14A—O5A—H5AA109.5C2B—C1B—C10B114.1 (4)
C25A—O6A—H6AA109.5C2B—C1B—H1C108.7
C30A—O7A—C26A114.6 (5)C10B—C1B—H1C108.7
C27A—O8A—H8AA109.5C2B—C1B—H1D108.7
C2A—C1A—C10A115.0 (4)C10B—C1B—H1D108.7
C2A—C1A—H1A108.5H1C—C1B—H1D107.6
C10A—C1A—H1A108.5C1B—C2B—C3B111.0 (5)
C2A—C1A—H1B108.5C1B—C2B—H2C109.4
C10A—C1A—H1B108.5C3B—C2B—H2C109.4
H1A—C1A—H1B107.5C1B—C2B—H2D109.4
C1A—C2A—C3A110.5 (5)C3B—C2B—H2D109.4
C1A—C2A—H2A109.5H2C—C2B—H2D108.0
C3A—C2A—H2A109.5O2B—C3B—C2B106.8 (4)
C1A—C2A—H2B109.5O2B—C3B—C4B111.8 (4)
C3A—C2A—H2B109.5C2B—C3B—C4B110.4 (4)
H2A—C2A—H2B108.1O2B—C3B—H3B109.3
O2A—C3A—C4A111.5 (4)C2B—C3B—H3B109.3
O2A—C3A—C2A106.3 (4)C4B—C3B—H3B109.3
C4A—C3A—C2A110.7 (4)C3B—C4B—C5B114.0 (4)
O2A—C3A—H3A109.4C3B—C4B—H4C108.7
C4A—C3A—H3A109.4C5B—C4B—H4C108.7
C2A—C3A—H3A109.4C3B—C4B—H4D108.7
C3A—C4A—C5A113.5 (4)C5B—C4B—H4D108.7
C3A—C4A—H4A108.9H4C—C4B—H4D107.6
C5A—C4A—H4A108.9C6B—C5B—C4B111.4 (4)
C3A—C4A—H4B108.9C6B—C5B—C10B111.2 (4)
C5A—C4A—H4B108.9C4B—C5B—C10B112.3 (4)
H4A—C4A—H4B107.7C6B—C5B—H5B107.2
C6A—C5A—C4A111.0 (4)C4B—C5B—H5B107.2
C6A—C5A—C10A112.3 (4)C10B—C5B—H5B107.2
C4A—C5A—C10A112.6 (4)C5B—C6B—C7B112.5 (4)
C6A—C5A—H5A106.8C5B—C6B—H6C109.1
C4A—C5A—H5A106.8C7B—C6B—H6C109.1
C10A—C5A—H5A106.8C5B—C6B—H6D109.1
C5A—C6A—C7A112.1 (4)C7B—C6B—H6D109.1
C5A—C6A—H6A109.2H6C—C6B—H6D107.8
C7A—C6A—H6A109.2C8B—C7B—C6B111.4 (5)
C5A—C6A—H6B109.2C8B—C7B—H7C109.3
C7A—C6A—H6B109.2C6B—C7B—H7C109.3
H6A—C6A—H6B107.9C8B—C7B—H7D109.3
C6A—C7A—C8A112.6 (4)C6B—C7B—H7D109.3
C6A—C7A—H7A109.1H7C—C7B—H7D108.0
C8A—C7A—H7A109.1C14B—C8B—C7B111.9 (4)
C6A—C7A—H7B109.1C14B—C8B—C9B113.7 (4)
C8A—C7A—H7B109.1C7B—C8B—C9B110.0 (4)
H7A—C7A—H7B107.8C14B—C8B—H8B106.9
C7A—C8A—C14A111.4 (4)C7B—C8B—H8B106.9
C7A—C8A—C9A109.6 (4)C9B—C8B—H8B106.9
C14A—C8A—C9A114.8 (4)C10B—C9B—C11B113.2 (4)
C7A—C8A—H8A106.9C10B—C9B—C8B111.8 (4)
C14A—C8A—H8A106.9C11B—C9B—C8B110.2 (4)
C9A—C8A—H8A106.9C10B—C9B—H9B107.1
C11A—C9A—C8A111.4 (4)C11B—C9B—H9B107.1
C11A—C9A—C10A113.9 (4)C8B—C9B—H9B107.1
C8A—C9A—C10A111.5 (4)C9B—C10B—C1B112.4 (5)
C11A—C9A—H9A106.5C9B—C10B—C19B111.2 (4)
C8A—C9A—H9A106.5C1B—C10B—C19B106.5 (5)
C10A—C9A—H9A106.5C9B—C10B—C5B110.4 (4)
C1A—C10A—C19A106.3 (4)C1B—C10B—C5B107.4 (4)
C1A—C10A—C9A112.7 (4)C19B—C10B—C5B108.8 (5)
C19A—C10A—C9A111.3 (4)C12B—C11B—C9B112.1 (4)
C1A—C10A—C5A107.7 (4)C12B—C11B—H11C109.2
C19A—C10A—C5A108.8 (4)C9B—C11B—H11C109.2
C9A—C10A—C5A109.8 (4)C12B—C11B—H11D109.2
C9A—C11A—C12A112.2 (4)C9B—C11B—H11D109.2
C9A—C11A—H11A109.2H11C—C11B—H11D107.9
C12A—C11A—H11A109.2C11B—C12B—C13B112.0 (4)
C9A—C11A—H11B109.2C11B—C12B—H12C109.2
C12A—C11A—H11B109.2C13B—C12B—H12C109.2
H11A—C11A—H11B107.9C11B—C12B—H12D109.2
C11A—C12A—C13A114.0 (4)C13B—C12B—H12D109.2
C11A—C12A—H12B108.8H12C—C12B—H12D107.9
C13A—C12A—H12B108.8C18B—C13B—C12B109.5 (4)
C11A—C12A—H12A108.8C18B—C13B—C14B114.1 (4)
C13A—C12A—H12A108.8C12B—C13B—C14B109.3 (4)
H12B—C12A—H12A107.6C18B—C13B—C17B113.3 (4)
C18A—C13A—C12A109.5 (4)C12B—C13B—C17B105.9 (4)
C18A—C13A—C14A112.8 (4)C14B—C13B—C17B104.3 (4)
C12A—C13A—C14A108.6 (4)O5B—C14B—C8B108.6 (4)
C18A—C13A—C17A114.7 (4)O5B—C14B—C15B107.8 (4)
C12A—C13A—C17A107.1 (4)C8B—C14B—C15B116.9 (4)
C14A—C13A—C17A103.8 (4)O5B—C14B—C13B106.4 (4)
O5A—C14A—C15A109.3 (4)C8B—C14B—C13B113.2 (4)
O5A—C14A—C8A108.6 (4)C15B—C14B—C13B103.3 (4)
C15A—C14A—C8A115.9 (4)C14B—C15B—C16B104.4 (4)
O5A—C14A—C13A105.7 (3)C14B—C15B—H15C110.9
C15A—C14A—C13A102.8 (4)C16B—C15B—H15C110.9
C8A—C14A—C13A114.0 (4)C14B—C15B—H15D110.9
C16A—C15A—C14A105.7 (4)C16B—C15B—H15D110.9
C16A—C15A—H15A110.6H15C—C15B—H15D108.9
C14A—C15A—H15A110.6C15B—C16B—C17B107.4 (4)
C16A—C15A—H15B110.6C15B—C16B—H16D110.2
C14A—C15A—H15B110.6C17B—C16B—H16D110.2
H15A—C15A—H15B108.7C15B—C16B—H16C110.2
C15A—C16A—C17A106.5 (4)C17B—C16B—H16C110.2
C15A—C16A—H16A110.4H16D—C16B—H16C108.5
C17A—C16A—H16A110.4C20B—C17B—C16B114.6 (4)
C15A—C16A—H16B110.4C20B—C17B—C13B114.3 (4)
C17A—C16A—H16B110.4C16B—C17B—C13B104.2 (4)
H16A—C16A—H16B108.6C20B—C17B—H17B107.8
O8A—C27A—C28A109.1 (4)C16B—C17B—H17B107.8
O8A—C27A—C26A111.9 (4)C13B—C17B—H17B107.8
C28A—C27A—C26A109.0 (4)C13B—C18B—H18D109.5
O8A—C27A—H27A109.0C13B—C18B—H18E109.5
C28A—C27A—H27A109.0H18D—C18B—H18E109.5
C26A—C27A—H27A109.0C13B—C18B—H18F109.5
O3A—C28A—C29A106.4 (5)H18D—C18B—H18F109.5
O3A—C28A—C27A108.7 (4)H18E—C18B—H18F109.5
C29A—C28A—C27A112.9 (4)C10B—C19B—H19D109.5
O3A—C28A—H28A109.6C10B—C19B—H19E109.5
C29A—C28A—H28A109.6H19D—C19B—H19E109.5
C27A—C28A—H28A109.6C10B—C19B—H19F109.5
C28A—C29A—H29A109.5H19D—C19B—H19F109.5
C28A—C29A—H29B109.5H19E—C19B—H19F109.5
H29A—C29A—H29B109.5C22B—C20B—C17B127.9 (6)
C28A—C29A—H29C109.5C22B—C20B—C21B106.1 (5)
H29A—C29A—H29C109.5C17B—C20B—C21B125.9 (5)
H29B—C29A—H29C109.5O1B—C21B—C20B105.6 (5)
O7A—C30A—H30A109.5O1B—C21B—H21D110.6
O7A—C30A—H30B109.5C20B—C21B—H21D110.6
H30A—C30A—H30B109.5O1B—C21B—H21C110.6
O7A—C30A—H30C109.5C20B—C21B—H21C110.6
H30A—C30A—H30C109.5H21D—C21B—H21C108.8
H30B—C30A—H30C109.5C20B—C22B—C23B110.1 (6)
C20A—C17A—C16A112.6 (4)C20B—C22B—H22B125.0
C20A—C17A—C13A115.9 (4)C23B—C22B—H22B125.0
C16A—C17A—C13A106.2 (4)O4B—C23B—O1B120.7 (7)
C20A—C17A—H17A107.2O4B—C23B—C22B130.3 (8)
C16A—C17A—H17A107.2O1B—C23B—C22B109.0 (5)
C13A—C17A—H17A107.2O2B—C24B—O3B111.9 (4)
C13A—C18A—H18A109.5O2B—C24B—C25B109.6 (4)
C13A—C18A—H18B109.5O3B—C24B—C25B109.2 (4)
H18A—C18A—H18B109.5O2B—C24B—H24B108.7
C13A—C18A—H18C109.5O3B—C24B—H24B108.7
H18A—C18A—H18C109.5C25B—C24B—H24B108.7
H18B—C18A—H18C109.5O6B—C25B—C26B111.5 (4)
C10A—C19A—H19A109.5O6B—C25B—C24B109.5 (4)
C10A—C19A—H19B109.5C26B—C25B—C24B112.1 (4)
H19A—C19A—H19B109.5O6B—C25B—H25B107.9
C10A—C19A—H19C109.5C26B—C25B—H25B107.9
H19A—C19A—H19C109.5C24B—C25B—H25B107.9
H19B—C19A—H19C109.5O7B—C26B—C25B110.7 (4)
C22A—C20A—C21A107.9 (5)O7B—C26B—C27B106.0 (4)
C22A—C20A—C17A127.1 (5)C25B—C26B—C27B111.2 (4)
C21A—C20A—C17A124.9 (5)O7B—C26B—H26B109.6
O1A—C21A—C20A106.7 (5)C25B—C26B—H26B109.6
O1A—C21A—H21A110.4C27B—C26B—H26B109.6
C20A—C21A—H21A110.4O8B—C27B—C28B107.9 (4)
O1A—C21A—H21B110.4O8B—C27B—C26B110.2 (4)
C20A—C21A—H21B110.4C28B—C27B—C26B109.4 (4)
H21A—C21A—H21B108.6O8B—C27B—H27B109.8
C20A—C22A—C23A107.7 (6)C28B—C27B—H27B109.8
C20A—C22A—H22A126.2C26B—C27B—H27B109.8
C23A—C22A—H22A126.2O3B—C28B—C27B108.1 (4)
O4A—C23A—O1A119.2 (7)O3B—C28B—C29B105.9 (4)
O4A—C23A—C22A131.3 (8)C27B—C28B—C29B113.4 (5)
O1A—C23A—C22A109.4 (5)O3B—C28B—H28B109.8
O2A—C24A—O3A112.2 (4)C27B—C28B—H28B109.8
O2A—C24A—C25A109.7 (4)C29B—C28B—H28B109.8
O3A—C24A—C25A109.7 (4)C28B—C29B—H29D109.5
O2A—C24A—H24A108.4C28B—C29B—H29E109.5
O3A—C24A—H24A108.4H29D—C29B—H29E109.5
C25A—C24A—H24A108.4C28B—C29B—H29F109.5
O6A—C25A—C26A111.5 (4)H29D—C29B—H29F109.5
O6A—C25A—C24A110.2 (4)H29E—C29B—H29F109.5
C26A—C25A—C24A111.7 (4)O7B—C30B—H30D109.5
O6A—C25A—H25A107.7O7B—C30B—H30E109.5
C26A—C25A—H25A107.7H30D—C30B—H30E109.5
C24A—C25A—H25A107.7O7B—C30B—H30F109.5
O7A—C26A—C25A111.2 (4)H30D—C30B—H30F109.5
O7A—C26A—C27A105.4 (4)H30E—C30B—H30F109.5
C25A—C26A—C27A112.2 (4)O9—C31—H31A109.5
O7A—C26A—H26A109.3O9—C31—H31B109.5
C25A—C26A—H26A109.3H31A—C31—H31B109.5
C27A—C26A—H26A109.3O9—C31—H31C109.5
C23B—O1B—C21B109.2 (5)H31A—C31—H31C109.5
C24B—O2B—C3B112.9 (4)H31B—C31—H31C109.5
C24B—O3B—C28B113.2 (4)C31—O9—H9AA110.1
C14B—O5B—H5BB109.5H1W1—O1W—H2W1107.7
C10A—C1A—C2A—C3A57.9 (6)C10B—C1B—C2B—C3B59.0 (6)
C24A—O2A—C3A—C4A79.7 (5)C24B—O2B—C3B—C2B156.6 (4)
C24A—O2A—C3A—C2A159.6 (4)C24B—O2B—C3B—C4B82.6 (5)
C1A—C2A—C3A—O2A66.6 (5)C1B—C2B—C3B—O2B67.8 (5)
C1A—C2A—C3A—C4A54.6 (6)C1B—C2B—C3B—C4B53.9 (6)
O2A—C3A—C4A—C5A64.5 (5)O2B—C3B—C4B—C5B66.3 (5)
C2A—C3A—C4A—C5A53.6 (6)C2B—C3B—C4B—C5B52.4 (6)
C3A—C4A—C5A—C6A179.9 (4)C3B—C4B—C5B—C6B178.4 (4)
C3A—C4A—C5A—C10A53.0 (6)C3B—C4B—C5B—C10B52.9 (6)
C4A—C5A—C6A—C7A74.2 (5)C4B—C5B—C6B—C7B71.4 (6)
C10A—C5A—C6A—C7A52.9 (6)C10B—C5B—C6B—C7B54.7 (6)
C5A—C6A—C7A—C8A54.0 (6)C5B—C6B—C7B—C8B55.4 (6)
C6A—C7A—C8A—C14A176.1 (4)C6B—C7B—C8B—C14B177.8 (4)
C6A—C7A—C8A—C9A55.8 (6)C6B—C7B—C8B—C9B54.8 (6)
C7A—C8A—C9A—C11A174.0 (4)C14B—C8B—C9B—C10B177.1 (4)
C14A—C8A—C9A—C11A47.8 (6)C7B—C8B—C9B—C10B56.4 (5)
C7A—C8A—C9A—C10A57.5 (5)C14B—C8B—C9B—C11B50.3 (6)
C14A—C8A—C9A—C10A176.3 (4)C7B—C8B—C9B—C11B176.7 (4)
C2A—C1A—C10A—C19A171.3 (5)C11B—C9B—C10B—C1B58.9 (6)
C2A—C1A—C10A—C9A66.5 (6)C8B—C9B—C10B—C1B176.0 (4)
C2A—C1A—C10A—C5A54.8 (6)C11B—C9B—C10B—C19B60.4 (7)
C11A—C9A—C10A—C1A56.0 (6)C8B—C9B—C10B—C19B64.8 (6)
C8A—C9A—C10A—C1A176.8 (4)C11B—C9B—C10B—C5B178.8 (5)
C11A—C9A—C10A—C19A63.3 (6)C8B—C9B—C10B—C5B56.1 (5)
C8A—C9A—C10A—C19A63.9 (5)C2B—C1B—C10B—C9B65.1 (6)
C11A—C9A—C10A—C5A176.1 (4)C2B—C1B—C10B—C19B172.9 (5)
C8A—C9A—C10A—C5A56.7 (5)C2B—C1B—C10B—C5B56.6 (6)
C6A—C5A—C10A—C1A177.0 (4)C6B—C5B—C10B—C9B54.9 (6)
C4A—C5A—C10A—C1A50.8 (5)C4B—C5B—C10B—C9B70.7 (5)
C6A—C5A—C10A—C19A68.1 (5)C6B—C5B—C10B—C1B177.7 (5)
C4A—C5A—C10A—C19A165.7 (4)C4B—C5B—C10B—C1B52.2 (5)
C6A—C5A—C10A—C9A53.9 (5)C6B—C5B—C10B—C19B67.4 (6)
C4A—C5A—C10A—C9A72.3 (5)C4B—C5B—C10B—C19B167.0 (5)
C8A—C9A—C11A—C12A51.8 (6)C10B—C9B—C11B—C12B179.4 (4)
C10A—C9A—C11A—C12A179.1 (4)C8B—C9B—C11B—C12B53.4 (6)
C9A—C11A—C12A—C13A57.9 (6)C9B—C11B—C12B—C13B58.4 (6)
C11A—C12A—C13A—C18A69.1 (5)C11B—C12B—C13B—C18B69.1 (5)
C11A—C12A—C13A—C14A54.5 (6)C11B—C12B—C13B—C14B56.5 (5)
C11A—C12A—C13A—C17A166.0 (4)C11B—C12B—C13B—C17B168.4 (4)
C7A—C8A—C14A—O5A69.5 (5)C7B—C8B—C14B—O5B65.1 (5)
C9A—C8A—C14A—O5A165.2 (4)C9B—C8B—C14B—O5B169.5 (4)
C7A—C8A—C14A—C15A53.9 (6)C7B—C8B—C14B—C15B57.1 (6)
C9A—C8A—C14A—C15A71.4 (5)C9B—C8B—C14B—C15B68.3 (6)
C7A—C8A—C14A—C13A172.9 (4)C7B—C8B—C14B—C13B177.0 (4)
C9A—C8A—C14A—C13A47.7 (5)C9B—C8B—C14B—C13B51.6 (5)
C18A—C13A—C14A—O5A46.7 (5)C18B—C13B—C14B—O5B49.5 (5)
C12A—C13A—C14A—O5A168.2 (4)C12B—C13B—C14B—O5B172.4 (4)
C17A—C13A—C14A—O5A78.1 (4)C17B—C13B—C14B—O5B74.7 (4)
C18A—C13A—C14A—C15A161.2 (4)C18B—C13B—C14B—C8B69.7 (5)
C12A—C13A—C14A—C15A77.2 (5)C12B—C13B—C14B—C8B53.2 (5)
C17A—C13A—C14A—C15A36.5 (5)C17B—C13B—C14B—C8B166.1 (4)
C18A—C13A—C14A—C8A72.5 (5)C18B—C13B—C14B—C15B162.9 (4)
C12A—C13A—C14A—C8A49.1 (5)C12B—C13B—C14B—C15B74.2 (5)
C17A—C13A—C14A—C8A162.8 (4)C17B—C13B—C14B—C15B38.7 (5)
O5A—C14A—C15A—C16A74.0 (5)O5B—C14B—C15B—C16B72.9 (5)
C8A—C14A—C15A—C16A162.9 (4)C8B—C14B—C15B—C16B164.4 (4)
C13A—C14A—C15A—C16A37.9 (5)C13B—C14B—C15B—C16B39.4 (5)
C14A—C15A—C16A—C17A24.4 (5)C14B—C15B—C16B—C17B25.2 (5)
C24A—O3A—C28A—C29A171.6 (4)C15B—C16B—C17B—C20B126.8 (5)
C24A—O3A—C28A—C27A66.5 (5)C15B—C16B—C17B—C13B1.1 (5)
O8A—C27A—C28A—O3A178.8 (4)C18B—C13B—C17B—C20B21.7 (6)
C26A—C27A—C28A—O3A58.8 (5)C12B—C13B—C17B—C20B141.7 (4)
O8A—C27A—C28A—C29A61.0 (6)C14B—C13B—C17B—C20B103.0 (5)
C26A—C27A—C28A—C29A176.7 (5)C18B—C13B—C17B—C16B147.5 (5)
C15A—C16A—C17A—C20A128.9 (5)C12B—C13B—C17B—C16B92.4 (5)
C15A—C16A—C17A—C13A1.1 (6)C14B—C13B—C17B—C16B22.8 (5)
C18A—C13A—C17A—C20A19.6 (6)C16B—C17B—C20B—C22B132.0 (6)
C12A—C13A—C17A—C20A141.3 (5)C13B—C17B—C20B—C22B107.8 (7)
C14A—C13A—C17A—C20A103.9 (5)C16B—C17B—C20B—C21B47.0 (7)
C18A—C13A—C17A—C16A145.4 (5)C13B—C17B—C20B—C21B73.2 (7)
C12A—C13A—C17A—C16A92.9 (5)C23B—O1B—C21B—C20B0.4 (7)
C14A—C13A—C17A—C16A21.9 (5)C22B—C20B—C21B—O1B0.6 (7)
C16A—C17A—C20A—C22A135.7 (6)C17B—C20B—C21B—O1B178.6 (5)
C13A—C17A—C20A—C22A101.7 (7)C17B—C20B—C22B—C23B178.6 (6)
C16A—C17A—C20A—C21A43.1 (7)C21B—C20B—C22B—C23B0.6 (7)
C13A—C17A—C20A—C21A79.4 (7)C21B—O1B—C23B—O4B177.4 (8)
C23A—O1A—C21A—C20A0.1 (7)C21B—O1B—C23B—C22B0.0 (8)
C22A—C20A—C21A—O1A0.3 (7)C20B—C22B—C23B—O4B177.5 (8)
C17A—C20A—C21A—O1A178.8 (5)C20B—C22B—C23B—O1B0.4 (8)
C21A—C20A—C22A—C23A0.3 (7)C3B—O2B—C24B—O3B65.5 (5)
C17A—C20A—C22A—C23A178.7 (5)C3B—O2B—C24B—C25B173.2 (4)
C21A—O1A—C23A—O4A178.7 (7)C28B—O3B—C24B—O2B61.0 (5)
C21A—O1A—C23A—C22A0.1 (8)C28B—O3B—C24B—C25B60.5 (5)
C20A—C22A—C23A—O4A178.4 (8)O2B—C24B—C25B—O6B53.1 (5)
C20A—C22A—C23A—O1A0.3 (8)O3B—C24B—C25B—O6B176.0 (4)
C3A—O2A—C24A—O3A64.6 (5)O2B—C24B—C25B—C26B71.1 (5)
C3A—O2A—C24A—C25A173.1 (4)O3B—C24B—C25B—C26B51.8 (5)
C28A—O3A—C24A—O2A60.4 (5)C30B—O7B—C26B—C25B92.5 (6)
C28A—O3A—C24A—C25A61.9 (5)C30B—O7B—C26B—C27B146.8 (6)
O2A—C24A—C25A—O6A52.4 (5)O6B—C25B—C26B—O7B69.8 (5)
O3A—C24A—C25A—O6A176.1 (4)C24B—C25B—C26B—O7B167.2 (4)
O2A—C24A—C25A—C26A72.2 (5)O6B—C25B—C26B—C27B172.6 (4)
O3A—C24A—C25A—C26A51.5 (5)C24B—C25B—C26B—C27B49.6 (5)
C30A—O7A—C26A—C25A90.6 (6)O7B—C26B—C27B—O8B67.1 (5)
C30A—O7A—C26A—C27A147.5 (6)C25B—C26B—C27B—O8B172.5 (4)
O6A—C25A—C26A—O7A70.2 (5)O7B—C26B—C27B—C28B174.4 (4)
C24A—C25A—C26A—O7A166.0 (4)C25B—C26B—C27B—C28B54.0 (5)
O6A—C25A—C26A—C27A172.0 (4)C24B—O3B—C28B—C27B65.9 (5)
C24A—C25A—C26A—C27A48.2 (5)C24B—O3B—C28B—C29B172.2 (4)
O8A—C27A—C26A—O7A66.5 (5)O8B—C27B—C28B—O3B179.7 (4)
C28A—C27A—C26A—O7A172.8 (4)C26B—C27B—C28B—O3B59.8 (5)
O8A—C27A—C26A—C25A172.3 (4)O8B—C27B—C28B—C29B63.1 (6)
C28A—C27A—C26A—C25A51.6 (5)C26B—C27B—C28B—C29B176.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5A—H5AA···O1W0.822.112.770 (5)137
O6A—H6AA···O4Ai0.821.952.756 (8)170
O8A—H8AA···O7B0.822.152.941 (6)163
O5B—H5BB···O5Aii0.822.343.161 (4)174
O6B—H6BB···O4Biii0.821.842.659 (8)173
O8B—H8BB···O7A0.822.162.961 (6)167
O9—H9AA···O4A0.901.922.792 (9)165
O1W—H1W1···O9iv0.851.952.762 (7)159
O1W—H2W1···O6Bv0.852.162.926 (6)150
Symmetry codes: (i) x1, y+1, z; (ii) x2, y+1, z1; (iii) x+1, y1, z; (iv) x1, y, z; (v) x+1, y1, z+1.
(II) 3β-o-(L-2'-o-acetyl thevetoyl)-14β-hydroxy-5β-card-20 (22)-enolide top
Crystal data top
C32H48O9F(000) = 624
Mr = 576.70Dx = 1.237 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.3351 (3) ÅCell parameters from 8192 reflections
b = 21.4770 (9) Åθ = 1.9–29.5°
c = 9.9056 (4) ŵ = 0.09 mm1
β = 97.007 (1)°T = 293 K
V = 1548.8 (1) Å3Slab, colourless
Z = 20.50 × 0.48 × 0.26 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3461 independent reflections
Radiation source: fine-focus sealed tube3057 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.104
Detector resolution: 8.33 pixels mm-1θmax = 27.0°, θmin = 1.9°
ω scansh = 99
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 2716
Tmin = 0.957, Tmax = 0.977l = 1212
10311 measured reflections
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0277P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3461 reflectionsΔρmax = 0.46 e Å3
376 parametersΔρmin = 0.42 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.059 (4)
Crystal data top
C32H48O9V = 1548.8 (1) Å3
Mr = 576.70Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.3351 (3) ŵ = 0.09 mm1
b = 21.4770 (9) ÅT = 293 K
c = 9.9056 (4) Å0.50 × 0.48 × 0.26 mm
β = 97.007 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
3461 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
3057 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.977Rint = 0.104
10311 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.106H-atom parameters constrained
S = 1.01Δρmax = 0.46 e Å3
3461 reflectionsΔρmin = 0.42 e Å3
376 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.

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.

All H atoms in (I) and (II) were fixed geometrically with ideal bond lengths and angles, and were treated as riding atoms with displacement parameters Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O). Due to a large fraction of weak data at higher angles, the 2θ maximum is limited to 54°.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8702 (3)0.39833 (11)0.22303 (19)0.0355 (5)
O20.5568 (2)0.80573 (8)1.03926 (17)0.0202 (4)
O30.5051 (2)0.91233 (9)0.99367 (17)0.0228 (4)
O40.7986 (3)0.31586 (10)0.3445 (2)0.0405 (6)
O50.7325 (2)0.48921 (8)0.65740 (17)0.0214 (4)
H5A0.83570.48360.69750.032*
O60.4333 (2)0.81558 (9)1.28906 (19)0.0277 (4)
O70.6948 (3)0.90537 (10)1.40125 (18)0.0339 (5)
O80.9400 (3)0.94492 (10)1.2060 (2)0.0329 (5)
H8A0.98960.91061.21100.049*
O90.1323 (3)0.83055 (12)1.2285 (3)0.0486 (6)
C220.6948 (4)0.41973 (13)0.3943 (3)0.0267 (6)
H220.62480.41300.46510.032*
C230.7865 (4)0.37137 (14)0.3234 (3)0.0300 (6)
C210.8376 (4)0.46436 (15)0.2252 (3)0.0319 (6)
H21A0.76960.47800.14020.038*
H21B0.95270.48700.23950.038*
C200.7275 (3)0.47484 (13)0.3414 (3)0.0227 (5)
C170.6733 (3)0.53949 (12)0.3791 (2)0.0217 (5)
H170.67270.56600.29850.026*
C160.4791 (3)0.54199 (14)0.4258 (3)0.0254 (5)
H16A0.40330.57210.37190.030*
H16B0.42040.50150.41440.030*
C150.5022 (3)0.56093 (12)0.5763 (2)0.0202 (5)
H15A0.46260.60360.58640.024*
H15B0.43010.53400.62790.024*
C140.7076 (3)0.55413 (11)0.6260 (2)0.0166 (5)
C130.8026 (3)0.57067 (12)0.4989 (2)0.0194 (5)
C120.7944 (4)0.64185 (13)0.4787 (3)0.0253 (6)
H12A0.86100.65270.40330.030*
H12B0.66730.65420.45470.030*
C110.8746 (4)0.67828 (12)0.6041 (3)0.0259 (6)
H11A0.86550.72250.58480.031*
H11B1.00350.66800.62580.031*
C90.7726 (3)0.66331 (11)0.7270 (2)0.0182 (5)
H90.64360.67460.70100.022*
C80.7768 (3)0.59223 (11)0.7539 (2)0.0181 (5)
H80.90560.58070.77990.022*
C70.6725 (4)0.57457 (12)0.8727 (2)0.0240 (5)
H7A0.69100.53060.89260.029*
H7B0.54220.58120.84650.029*
C60.7349 (4)0.61250 (13)1.0011 (3)0.0264 (6)
H6A0.65760.60241.07080.032*
H6B0.86020.60131.03510.032*
C50.7247 (3)0.68265 (12)0.9729 (2)0.0208 (5)
H50.77860.70381.05590.025*
C100.8399 (3)0.70121 (12)0.8579 (3)0.0206 (5)
C10.8159 (3)0.77213 (12)0.8345 (3)0.0235 (5)
H1A0.87070.79390.91530.028*
H1B0.88210.78430.75980.028*
C20.6159 (3)0.79280 (12)0.8027 (2)0.0211 (5)
H2A0.61120.83780.79380.025*
H2B0.56400.77490.71650.025*
C30.5012 (3)0.77273 (12)0.9135 (2)0.0195 (5)
H30.37140.78140.88350.023*
C40.5246 (3)0.70378 (12)0.9444 (2)0.0205 (5)
H4A0.46500.68030.86780.025*
H4B0.46270.69401.02280.025*
C240.4517 (3)0.85795 (12)1.0619 (2)0.0199 (5)
H240.32190.84911.03250.024*
C280.6959 (3)0.92727 (13)1.0249 (3)0.0236 (5)
H280.76970.89310.99490.028*
C270.7467 (3)0.93729 (12)1.1779 (3)0.0231 (5)
H270.68910.97621.20230.028*
C260.6768 (4)0.88529 (12)1.2631 (2)0.0216 (5)
H260.75130.84791.25580.026*
C250.4783 (3)0.87072 (12)1.2142 (2)0.0213 (5)
H250.40030.90561.23510.026*
C181.0015 (3)0.54883 (14)0.5079 (3)0.0269 (6)
H18A1.07270.56870.58350.040*
H18B1.05060.55950.42540.040*
H18C1.00640.50450.52030.040*
C191.0452 (4)0.69052 (15)0.9029 (3)0.0336 (7)
H19A1.08110.71240.98650.050*
H19B1.11520.70570.83400.050*
H19C1.06780.64680.91650.050*
C300.7906 (6)0.8647 (2)1.4945 (3)0.0538 (10)
H30A0.79970.88261.58390.081*
H30B0.91160.85791.46980.081*
H30C0.72640.82581.49380.081*
C290.7272 (4)0.98522 (16)0.9435 (3)0.0374 (7)
H29A0.70370.97600.84810.056*
H29B0.85210.99880.96500.056*
H29C0.64571.01760.96570.056*
C310.2567 (4)0.80048 (15)1.2863 (3)0.0328 (6)
C320.2341 (6)0.74137 (19)1.3629 (4)0.0565 (10)
H32A0.11690.72321.33180.085*
H32B0.24080.75031.45830.085*
H32C0.33000.71281.34750.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0362 (11)0.0396 (13)0.0315 (10)0.0075 (9)0.0078 (8)0.0123 (9)
O20.0186 (8)0.0179 (9)0.0233 (8)0.0039 (7)0.0005 (6)0.0053 (7)
O30.0228 (8)0.0219 (9)0.0235 (8)0.0032 (7)0.0017 (7)0.0049 (7)
O40.0414 (11)0.0276 (12)0.0487 (13)0.0049 (9)0.0092 (10)0.0118 (10)
O50.0242 (9)0.0137 (9)0.0252 (8)0.0002 (7)0.0017 (7)0.0036 (7)
O60.0287 (9)0.0261 (10)0.0302 (10)0.0018 (8)0.0112 (8)0.0052 (8)
O70.0436 (12)0.0350 (12)0.0212 (9)0.0085 (9)0.0034 (8)0.0045 (8)
O80.0273 (10)0.0278 (11)0.0422 (11)0.0079 (8)0.0011 (8)0.0097 (9)
O90.0288 (11)0.0453 (15)0.0741 (17)0.0011 (11)0.0152 (11)0.0037 (13)
C220.0280 (13)0.0270 (14)0.0251 (12)0.0016 (11)0.0040 (10)0.0070 (11)
C230.0235 (13)0.0345 (17)0.0295 (14)0.0020 (11)0.0070 (11)0.0115 (12)
C210.0320 (14)0.0365 (16)0.0292 (14)0.0027 (12)0.0118 (11)0.0062 (12)
C200.0180 (11)0.0290 (15)0.0206 (11)0.0017 (10)0.0012 (9)0.0046 (10)
C170.0246 (12)0.0235 (13)0.0173 (11)0.0033 (10)0.0034 (9)0.0015 (10)
C160.0190 (11)0.0322 (15)0.0244 (12)0.0051 (10)0.0001 (9)0.0025 (11)
C150.0162 (11)0.0238 (13)0.0213 (12)0.0017 (10)0.0055 (9)0.0020 (10)
C140.0167 (10)0.0135 (11)0.0198 (11)0.0011 (9)0.0026 (9)0.0041 (9)
C130.0183 (11)0.0191 (13)0.0220 (12)0.0007 (9)0.0070 (9)0.0021 (10)
C120.0331 (13)0.0201 (13)0.0255 (13)0.0001 (10)0.0142 (11)0.0055 (10)
C110.0335 (14)0.0157 (12)0.0318 (13)0.0056 (11)0.0173 (11)0.0006 (11)
C90.0171 (10)0.0150 (11)0.0235 (11)0.0009 (9)0.0069 (9)0.0016 (9)
C80.0176 (10)0.0158 (12)0.0208 (11)0.0007 (9)0.0025 (9)0.0016 (9)
C70.0367 (14)0.0153 (13)0.0208 (12)0.0031 (10)0.0064 (10)0.0032 (10)
C60.0365 (14)0.0240 (14)0.0178 (12)0.0022 (11)0.0001 (10)0.0035 (10)
C50.0228 (12)0.0194 (13)0.0192 (11)0.0005 (9)0.0020 (9)0.0009 (9)
C100.0164 (11)0.0174 (12)0.0279 (13)0.0025 (9)0.0017 (9)0.0011 (10)
C10.0237 (12)0.0172 (13)0.0309 (13)0.0053 (10)0.0088 (10)0.0039 (10)
C20.0270 (12)0.0147 (12)0.0222 (11)0.0002 (10)0.0049 (9)0.0011 (9)
C30.0172 (11)0.0220 (13)0.0190 (11)0.0019 (9)0.0011 (9)0.0052 (10)
C40.0205 (11)0.0205 (13)0.0209 (11)0.0039 (10)0.0043 (9)0.0013 (10)
C240.0179 (11)0.0174 (12)0.0243 (12)0.0032 (9)0.0022 (9)0.0023 (10)
C280.0215 (12)0.0235 (14)0.0259 (12)0.0005 (10)0.0036 (10)0.0033 (10)
C270.0250 (12)0.0167 (12)0.0270 (13)0.0001 (10)0.0007 (10)0.0068 (10)
C260.0257 (12)0.0182 (12)0.0206 (11)0.0045 (10)0.0020 (9)0.0036 (10)
C250.0232 (12)0.0198 (13)0.0215 (12)0.0042 (10)0.0057 (9)0.0008 (10)
C180.0194 (11)0.0281 (15)0.0347 (14)0.0009 (10)0.0090 (10)0.0053 (11)
C190.0209 (13)0.0316 (16)0.0475 (17)0.0008 (11)0.0008 (12)0.0099 (13)
C300.063 (2)0.066 (3)0.0296 (16)0.021 (2)0.0074 (16)0.0073 (17)
C290.0442 (17)0.0342 (17)0.0359 (15)0.0070 (14)0.0131 (13)0.0053 (13)
C310.0321 (14)0.0301 (15)0.0390 (15)0.0021 (13)0.0151 (12)0.0054 (13)
C320.068 (2)0.047 (2)0.060 (2)0.0168 (19)0.0321 (19)0.0040 (19)
Geometric parameters (Å, º) top
O1—C231.360 (4)C7—C61.533 (4)
O1—C211.439 (4)C7—H7A0.9700
O2—C241.394 (3)C7—H7B0.9700
O2—C31.448 (3)C6—C51.533 (4)
O3—C241.428 (3)C6—H6A0.9700
O3—C281.432 (3)C6—H6B0.9700
O4—C231.212 (4)C5—C41.529 (3)
O5—C141.435 (3)C5—C101.551 (4)
O5—H5A0.8200C5—H50.9800
O6—C311.333 (3)C10—C191.535 (3)
O6—C251.456 (3)C10—C11.548 (4)
O7—C301.397 (4)C1—C21.528 (4)
O7—C261.426 (3)C1—H1A0.9700
O8—C271.420 (3)C1—H1B0.9700
O8—H8A0.8200C2—C31.524 (4)
O9—C311.204 (4)C2—H2A0.9700
C22—C201.328 (4)C2—H2B0.9700
C22—C231.463 (4)C3—C41.518 (4)
C22—H220.9300C3—H30.9800
C21—C201.501 (4)C4—H4A0.9700
C21—H21A0.9700C4—H4B0.9700
C21—H21B0.9700C24—C251.523 (3)
C20—C171.504 (4)C24—H240.9800
C17—C161.551 (4)C28—C291.516 (4)
C17—C131.576 (3)C28—C271.531 (3)
C17—H170.9800C28—H280.9800
C16—C151.535 (3)C27—C261.526 (4)
C16—H16A0.9700C27—H270.9800
C16—H16B0.9700C26—C251.510 (3)
C15—C141.534 (3)C26—H260.9800
C15—H15A0.9700C25—H250.9800
C15—H15B0.9700C18—H18A0.9600
C14—C81.541 (3)C18—H18B0.9600
C14—C131.552 (3)C18—H18C0.9600
C13—C181.525 (3)C19—H19A0.9600
C13—C121.542 (4)C19—H19B0.9600
C12—C111.524 (4)C19—H19C0.9600
C12—H12A0.9700C30—H30A0.9600
C12—H12B0.9700C30—H30B0.9600
C11—C91.539 (3)C30—H30C0.9600
C11—H11A0.9700C29—H29A0.9600
C11—H11B0.9700C29—H29B0.9600
C9—C81.549 (3)C29—H29C0.9600
C9—C101.559 (3)C31—C321.498 (5)
C9—H90.9800C32—H32A0.9600
C8—C71.527 (3)C32—H32B0.9600
C8—H80.9800C32—H32C0.9600
C23—O1—C21108.5 (2)C19—C10—C1106.3 (2)
C24—O2—C3115.39 (18)C19—C10—C5110.6 (2)
C24—O3—C28113.47 (18)C1—C10—C5107.5 (2)
C14—O5—H5A109.5C19—C10—C9111.3 (2)
C31—O6—C25117.9 (2)C1—C10—C9111.8 (2)
C30—O7—C26115.2 (2)C5—C10—C9109.31 (18)
C27—O8—H8A109.5C2—C1—C10113.9 (2)
C20—C22—C23109.1 (3)C2—C1—H1A108.8
C20—C22—H22125.4C10—C1—H1A108.8
C23—C22—H22125.4C2—C1—H1B108.8
O4—C23—O1121.0 (3)C10—C1—H1B108.8
O4—C23—C22130.1 (3)H1A—C1—H1B107.7
O1—C23—C22108.9 (3)C3—C2—C1111.7 (2)
O1—C21—C20105.4 (2)C3—C2—H2A109.3
O1—C21—H21A110.7C1—C2—H2A109.3
C20—C21—H21A110.7C3—C2—H2B109.3
O1—C21—H21B110.7C1—C2—H2B109.3
C20—C21—H21B110.7H2A—C2—H2B107.9
H21A—C21—H21B108.8O2—C3—C4106.92 (19)
C22—C20—C21108.0 (2)O2—C3—C2111.05 (19)
C22—C20—C17131.2 (2)C4—C3—C2111.2 (2)
C21—C20—C17120.8 (2)O2—C3—H3109.2
C20—C17—C16112.7 (2)C4—C3—H3109.2
C20—C17—C13115.3 (2)C2—C3—H3109.2
C16—C17—C13104.53 (19)C3—C4—C5114.2 (2)
C20—C17—H17108.0C3—C4—H4A108.7
C16—C17—H17108.0C5—C4—H4A108.7
C13—C17—H17108.0C3—C4—H4B108.7
C15—C16—C17107.61 (19)C5—C4—H4B108.7
C15—C16—H16A110.2H4A—C4—H4B107.6
C17—C16—H16A110.2O2—C24—O3113.1 (2)
C15—C16—H16B110.2O2—C24—C25107.30 (19)
C17—C16—H16B110.2O3—C24—C25108.2 (2)
H16A—C16—H16B108.5O2—C24—H24109.4
C14—C15—C16105.89 (18)O3—C24—H24109.4
C14—C15—H15A110.6C25—C24—H24109.4
C16—C15—H15A110.6O3—C28—C29106.1 (2)
C14—C15—H15B110.6O3—C28—C27111.0 (2)
C16—C15—H15B110.6C29—C28—C27112.1 (2)
H15A—C15—H15B108.7O3—C28—H28109.2
O5—C14—C15104.81 (18)C29—C28—H28109.2
O5—C14—C8108.49 (18)C27—C28—H28109.2
C15—C14—C8115.16 (19)O8—C27—C26111.8 (2)
O5—C14—C13109.91 (19)O8—C27—C28109.1 (2)
C15—C14—C13103.82 (18)C26—C27—C28112.7 (2)
C8—C14—C13114.18 (19)O8—C27—H27107.7
C18—C13—C12109.6 (2)C26—C27—H27107.7
C18—C13—C14113.8 (2)C28—C27—H27107.7
C12—C13—C14108.5 (2)O7—C26—C25110.1 (2)
C18—C13—C17113.4 (2)O7—C26—C27108.1 (2)
C12—C13—C17108.2 (2)C25—C26—C27110.5 (2)
C14—C13—C17103.00 (18)O7—C26—H26109.4
C11—C12—C13113.5 (2)C25—C26—H26109.4
C11—C12—H12A108.9C27—C26—H26109.4
C13—C12—H12A108.9O6—C25—C26105.96 (19)
C11—C12—H12B108.9O6—C25—C24110.4 (2)
C13—C12—H12B108.9C26—C25—C24110.9 (2)
H12A—C12—H12B107.7O6—C25—H25109.8
C12—C11—C9111.2 (2)C26—C25—H25109.8
C12—C11—H11A109.4C24—C25—H25109.8
C9—C11—H11A109.4C13—C18—H18A109.5
C12—C11—H11B109.4C13—C18—H18B109.5
C9—C11—H11B109.4H18A—C18—H18B109.5
H11A—C11—H11B108.0C13—C18—H18C109.5
C11—C9—C8109.9 (2)H18A—C18—H18C109.5
C11—C9—C10114.43 (19)H18B—C18—H18C109.5
C8—C9—C10111.97 (19)C10—C19—H19A109.5
C11—C9—H9106.7C10—C19—H19B109.5
C8—C9—H9106.7H19A—C19—H19B109.5
C10—C9—H9106.7C10—C19—H19C109.5
C7—C8—C14110.84 (19)H19A—C19—H19C109.5
C7—C8—C9112.1 (2)H19B—C19—H19C109.5
C14—C8—C9112.60 (18)O7—C30—H30A109.5
C7—C8—H8107.0O7—C30—H30B109.5
C14—C8—H8107.0H30A—C30—H30B109.5
C9—C8—H8107.0O7—C30—H30C109.5
C8—C7—C6112.4 (2)H30A—C30—H30C109.5
C8—C7—H7A109.1H30B—C30—H30C109.5
C6—C7—H7A109.1C28—C29—H29A109.5
C8—C7—H7B109.1C28—C29—H29B109.5
C6—C7—H7B109.1H29A—C29—H29B109.5
H7A—C7—H7B107.9C28—C29—H29C109.5
C5—C6—C7111.6 (2)H29A—C29—H29C109.5
C5—C6—H6A109.3H29B—C29—H29C109.5
C7—C6—H6A109.3O9—C31—O6123.9 (3)
C5—C6—H6B109.3O9—C31—C32124.8 (3)
C7—C6—H6B109.3O6—C31—C32111.3 (3)
H6A—C6—H6B108.0C31—C32—H32A109.5
C4—C5—C6110.5 (2)C31—C32—H32B109.5
C4—C5—C10112.63 (19)H32A—C32—H32B109.5
C6—C5—C10111.6 (2)C31—C32—H32C109.5
C4—C5—H5107.3H32A—C32—H32C109.5
C6—C5—H5107.3H32B—C32—H32C109.5
C10—C5—H5107.3
C21—O1—C23—O4177.9 (2)C7—C6—C5—C1056.7 (3)
C21—O1—C23—C220.3 (3)C4—C5—C10—C19169.0 (2)
C20—C22—C23—O4175.9 (3)C6—C5—C10—C1966.0 (3)
C20—C22—C23—O12.1 (3)C4—C5—C10—C153.4 (3)
C23—O1—C21—C201.3 (3)C6—C5—C10—C1178.33 (19)
C23—C22—C20—C212.9 (3)C4—C5—C10—C968.1 (3)
C23—C22—C20—C17177.3 (2)C6—C5—C10—C956.8 (2)
O1—C21—C20—C222.7 (3)C11—C9—C10—C1958.5 (3)
O1—C21—C20—C17177.5 (2)C8—C9—C10—C1967.4 (3)
C22—C20—C17—C1636.5 (4)C11—C9—C10—C160.2 (3)
C21—C20—C17—C16143.3 (2)C8—C9—C10—C1173.89 (19)
C22—C20—C17—C1383.4 (3)C11—C9—C10—C5179.1 (2)
C21—C20—C17—C1396.8 (3)C8—C9—C10—C555.0 (3)
C20—C17—C16—C15114.8 (2)C19—C10—C1—C2174.1 (2)
C13—C17—C16—C1511.1 (3)C5—C10—C1—C255.7 (3)
C17—C16—C15—C1413.3 (3)C9—C10—C1—C264.2 (3)
C16—C15—C14—O582.5 (2)C10—C1—C2—C356.2 (3)
C16—C15—C14—C8158.3 (2)C24—O2—C3—C4141.8 (2)
C16—C15—C14—C1332.8 (3)C24—O2—C3—C296.7 (2)
O5—C14—C13—C1850.8 (3)C1—C2—C3—O267.6 (3)
C15—C14—C13—C18162.4 (2)C1—C2—C3—C451.4 (3)
C8—C14—C13—C1871.4 (3)O2—C3—C4—C570.2 (2)
O5—C14—C13—C12173.03 (18)C2—C3—C4—C551.2 (3)
C15—C14—C13—C1275.3 (2)C6—C5—C4—C3179.3 (2)
C8—C14—C13—C1250.9 (3)C10—C5—C4—C353.7 (3)
O5—C14—C13—C1772.4 (2)C3—O2—C24—O382.4 (2)
C15—C14—C13—C1739.3 (2)C3—O2—C24—C25158.4 (2)
C8—C14—C13—C17165.46 (19)C28—O3—C24—O254.8 (3)
C20—C17—C13—C1830.0 (3)C28—O3—C24—C2564.0 (2)
C16—C17—C13—C18154.3 (2)C24—O3—C28—C29179.5 (2)
C20—C17—C13—C12151.8 (2)C24—O3—C28—C2758.4 (3)
C16—C17—C13—C1283.9 (2)O3—C28—C27—O8173.4 (2)
C20—C17—C13—C1493.4 (2)C29—C28—C27—O868.1 (3)
C16—C17—C13—C1430.9 (2)O3—C28—C27—C2648.6 (3)
C18—C13—C12—C1170.1 (3)C29—C28—C27—C26167.1 (2)
C14—C13—C12—C1154.7 (3)C30—O7—C26—C25112.4 (3)
C17—C13—C12—C11165.8 (2)C30—O7—C26—C27126.8 (3)
C13—C12—C11—C959.2 (3)O8—C27—C26—O769.3 (3)
C12—C11—C9—C855.9 (3)C28—C27—C26—O7167.4 (2)
C12—C11—C9—C10177.1 (2)O8—C27—C26—C25170.1 (2)
O5—C14—C8—C758.8 (2)C28—C27—C26—C2546.8 (3)
C15—C14—C8—C758.2 (3)C31—O6—C25—C26166.2 (2)
C13—C14—C8—C7178.2 (2)C31—O6—C25—C2473.6 (3)
O5—C14—C8—C9174.77 (19)O7—C26—C25—O668.1 (2)
C15—C14—C8—C968.2 (2)C27—C26—C25—O6172.51 (19)
C13—C14—C8—C951.8 (3)O7—C26—C25—C24172.1 (2)
C11—C9—C8—C7178.4 (2)C27—C26—C25—C2452.7 (3)
C10—C9—C8—C753.3 (3)O2—C24—C25—O655.1 (2)
C11—C9—C8—C1452.6 (2)O3—C24—C25—O6177.51 (17)
C10—C9—C8—C14179.07 (18)O2—C24—C25—C2662.0 (3)
C14—C8—C7—C6178.8 (2)O3—C24—C25—C2660.4 (3)
C9—C8—C7—C652.1 (3)C25—O6—C31—O91.9 (4)
C8—C7—C6—C553.9 (3)C25—O6—C31—C32177.5 (2)
C7—C6—C5—C469.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O8i0.821.982.777 (3)163
O8—H8A···O9ii0.822.012.828 (3)175
C3—H3···O4iii0.982.553.295 (3)132
C25—H25···O5iv0.982.363.311 (3)164
C32—H32B···O4iv0.962.453.345 (4)154
Symmetry codes: (i) x+2, y1/2, z+2; (ii) x+1, y, z; (iii) x+1, y+1/2, z+1; (iv) x+1, y+1/2, z+2.

Experimental details

(I)(II)
Crystal data
Chemical formula2C30H46O8·CH4O·H2OC32H48O9
Mr1119.39576.70
Crystal system, space groupTriclinic, P1Monoclinic, P21
Temperature (K)213293
a, b, c (Å)10.4353 (5), 10.4491 (5), 14.8760 (7)7.3351 (3), 21.4770 (9), 9.9056 (4)
α, β, γ (°)92.412 (1), 101.471 (1), 109.599 (1)90, 97.007 (1), 90
V3)1487.1 (1)1548.8 (1)
Z12
Radiation typeMo KαMo Kα
µ (mm1)0.090.09
Crystal size (mm)0.44 × 0.32 × 0.100.50 × 0.48 × 0.26
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Siemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.961, 0.9910.957, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
9863, 6292, 4368 10311, 3461, 3057
Rint0.0720.104
(sin θ/λ)max1)0.6390.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.182, 0.97 0.045, 0.106, 1.01
No. of reflections62923461
No. of parameters715376
No. of restraints31
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.700.46, 0.42

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected bond lengths (Å) for (I) top
O2A—C24A1.405 (6)O2B—C24B1.398 (6)
O2A—C3A1.452 (6)O2B—C3B1.446 (6)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O5A—H5AA···O1W0.822.112.770 (5)137
O6A—H6AA···O4Ai0.821.952.756 (8)170
O8A—H8AA···O7B0.822.152.941 (6)163
O5B—H5BB···O5Aii0.822.343.161 (4)174
O6B—H6BB···O4Biii0.821.842.659 (8)173
O8B—H8BB···O7A0.822.162.961 (6)167
O9—H9AA···O4A0.901.922.792 (9)165
O1W—H1W1···O9iv0.851.952.762 (7)159
O1W—H2W1···O6Bv0.852.162.926 (6)150
Symmetry codes: (i) x1, y+1, z; (ii) x2, y+1, z1; (iii) x+1, y1, z; (iv) x1, y, z; (v) x+1, y1, z+1.
Selected bond lengths (Å) for (II) top
O2—C241.394 (3)O2—C31.448 (3)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O8i0.821.982.777 (3)163
O8—H8A···O9ii0.822.012.828 (3)175
C3—H3···O4iii0.982.553.295 (3)132
C25—H25···O5iv0.982.363.311 (3)164
C32—H32B···O4iv0.962.453.345 (4)154
Symmetry codes: (i) x+2, y1/2, z+2; (ii) x+1, y, z; (iii) x+1, y+1/2, z+1; (iv) x+1, y+1/2, z+2.
 

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