Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102023065/ta1401sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102023065/ta1401Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102023065/ta1401IIsup3.hkl |
CCDC references: 205306; 205307
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.
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).
2C30H46O8·CH4O·H2O | Z = 1 |
Mr = 1119.39 | F(000) = 608 |
Triclinic, P1 | Dx = 1.250 Mg m−3 |
a = 10.4353 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.4491 (5) Å | Cell parameters from 7201 reflections |
c = 14.8760 (7) Å | θ = 1.4–29.5° |
α = 92.412 (1)° | µ = 0.09 mm−1 |
β = 101.471 (1)° | T = 213 K |
γ = 109.599 (1)° | Slab, colorless |
V = 1487.1 (1) Å3 | 0.44 × 0.32 × 0.10 mm |
Siemens SMART CCD area-detector diffractometer | 6292 independent reflections |
Radiation source: fine-focus sealed tube | 4368 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.0°, θmin = 1.4° |
ω scans | h = −12→13 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −10→13 |
Tmin = 0.961, Tmax = 0.991 | l = −18→12 |
9863 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.182 | H-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 parameters | Δρmax = 0.68 e Å−3 |
3 restraints | Δρmin = −0.70 e Å−3 |
2C30H46O8·CH4O·H2O | γ = 109.599 (1)° |
Mr = 1119.39 | V = 1487.1 (1) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.4353 (5) Å | Mo Kα radiation |
b = 10.4491 (5) Å | µ = 0.09 mm−1 |
c = 14.8760 (7) Å | T = 213 K |
α = 92.412 (1)° | 0.44 × 0.32 × 0.10 mm |
β = 101.471 (1)° |
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 = 0.991 | Rint = 0.072 |
9863 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 3 restraints |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.68 e Å−3 |
6292 reflections | Δρmin = −0.70 e Å−3 |
715 parameters |
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°. |
x | y | z | Uiso*/Ueq | ||
O1A | 2.0161 (5) | −0.3352 (5) | 1.3098 (3) | 0.0426 (12) | |
O2A | 1.2261 (3) | 0.2619 (3) | 1.0060 (2) | 0.0185 (8) | |
O3A | 0.9814 (3) | 0.1861 (4) | 0.9698 (3) | 0.0220 (8) | |
O4A | 2.1558 (7) | −0.3886 (7) | 1.2351 (4) | 0.0759 (14) | |
O5A | 1.7495 (3) | −0.0856 (3) | 1.2920 (2) | 0.0169 (7) | |
H5AA | 1.7064 | −0.0747 | 1.3304 | 0.025* | |
O6A | 1.2410 (4) | 0.5050 (4) | 1.0947 (3) | 0.0315 (10) | |
H6AA | 1.2263 | 0.5414 | 1.1396 | 0.047* | |
O7A | 1.0606 (4) | 0.5924 (4) | 0.9477 (3) | 0.0299 (9) | |
O8A | 0.9493 (4) | 0.3986 (4) | 0.7860 (3) | 0.0326 (10) | |
H8AA | 0.9437 | 0.4750 | 0.7853 | 0.049* | |
C1A | 1.4814 (6) | 0.2168 (6) | 0.9897 (4) | 0.0234 (12) | |
H1A | 1.4805 | 0.3094 | 0.9909 | 0.028* | |
H1B | 1.5414 | 0.2085 | 0.9493 | 0.028* | |
C2A | 1.3339 (6) | 0.1181 (6) | 0.9484 (4) | 0.0258 (12) | |
H2A | 1.3343 | 0.0255 | 0.9420 | 0.031* | |
H2B | 1.3010 | 0.1402 | 0.8874 | 0.031* | |
C3A | 1.2356 (5) | 0.1267 (5) | 1.0097 (4) | 0.0206 (11) | |
H3A | 1.1431 | 0.0572 | 0.9849 | 0.025* | |
C4A | 1.2910 (5) | 0.1038 (5) | 1.1081 (4) | 0.0192 (11) | |
H4A | 1.2866 | 0.0097 | 1.1085 | 0.023* | |
H4B | 1.2309 | 0.1178 | 1.1467 | 0.023* | |
C5A | 1.4434 (5) | 0.2000 (5) | 1.1503 (4) | 0.0189 (11) | |
H5A | 1.4425 | 0.2935 | 1.1544 | 0.023* | |
C6A | 1.4930 (6) | 0.1722 (6) | 1.2486 (4) | 0.0222 (11) | |
H6A | 1.4216 | 0.1666 | 1.2828 | 0.027* | |
H6B | 1.5766 | 0.2479 | 1.2789 | 0.027* | |
C7A | 1.5243 (5) | 0.0396 (5) | 1.2506 (4) | 0.0205 (11) | |
H7A | 1.4378 | −0.0372 | 1.2285 | 0.025* | |
H7B | 1.5628 | 0.0301 | 1.3138 | 0.025* | |
C8A | 1.6278 (5) | 0.0347 (5) | 1.1909 (4) | 0.0169 (10) | |
H8A | 1.7142 | 0.1126 | 1.2156 | 0.020* | |
C9A | 1.5715 (5) | 0.0574 (5) | 1.0911 (4) | 0.0166 (10) | |
H9A | 1.4800 | −0.0150 | 1.0692 | 0.020* | |
C10A | 1.5455 (5) | 0.1952 (5) | 1.0880 (4) | 0.0169 (10) | |
C11A | 1.6624 (6) | 0.0387 (6) | 1.0275 (4) | 0.0251 (12) | |
H11A | 1.7515 | 0.1134 | 1.0433 | 0.030* | |
H11B | 1.6178 | 0.0423 | 0.9643 | 0.030* | |
C12A | 1.6873 (6) | −0.0972 (6) | 1.0339 (4) | 0.0220 (11) | |
H12B | 1.7465 | −0.1033 | 0.9925 | 0.026* | |
H12A | 1.5985 | −0.1715 | 1.0129 | 0.026* | |
C13A | 1.7556 (5) | −0.1159 (5) | 1.1317 (3) | 0.0161 (10) | |
C14A | 1.6652 (5) | −0.0956 (5) | 1.1996 (3) | 0.0134 (10) | |
C15A | 1.5415 (5) | −0.2312 (5) | 1.1799 (4) | 0.0184 (10) | |
H15A | 1.4976 | −0.2468 | 1.2321 | 0.022* | |
H15B | 1.4724 | −0.2306 | 1.1257 | 0.022* | |
C16A | 1.6026 (5) | −0.3418 (5) | 1.1634 (4) | 0.0250 (12) | |
H16A | 1.5374 | −0.4138 | 1.1163 | 0.030* | |
H16B | 1.6224 | −0.3818 | 1.2198 | 0.030* | |
C27A | 0.9609 (5) | 0.3633 (6) | 0.8770 (4) | 0.0205 (11) | |
H27A | 0.8768 | 0.3608 | 0.8978 | 0.025* | |
C28A | 0.9726 (5) | 0.2223 (6) | 0.8777 (4) | 0.0232 (11) | |
H28A | 1.0569 | 0.2240 | 0.8574 | 0.028* | |
C29A | 0.8465 (7) | 0.1119 (6) | 0.8178 (5) | 0.0379 (15) | |
H29A | 0.8572 | 0.0247 | 0.8232 | 0.057* | |
H29B | 0.8382 | 0.1301 | 0.7546 | 0.057* | |
H29C | 0.7640 | 0.1110 | 0.8375 | 0.057* | |
C30A | 1.1829 (8) | 0.7144 (7) | 0.9615 (7) | 0.059 (2) | |
H30A | 1.1550 | 0.7929 | 0.9555 | 0.088* | |
H30B | 1.2351 | 0.7089 | 0.9160 | 0.088* | |
H30C | 1.2400 | 0.7226 | 1.0221 | 0.088* | |
C17A | 1.7390 (5) | −0.2706 (5) | 1.1312 (4) | 0.0184 (10) | |
H17A | 1.7241 | −0.3077 | 1.0668 | 0.022* | |
C18A | 1.9056 (5) | −0.0168 (5) | 1.1586 (4) | 0.0229 (12) | |
H18A | 1.9505 | −0.0195 | 1.1085 | 0.034* | |
H18B | 1.9547 | −0.0426 | 1.2123 | 0.034* | |
H18C | 1.9063 | 0.0742 | 1.1719 | 0.034* | |
C19A | 1.6830 (6) | 0.3179 (5) | 1.1217 (5) | 0.0303 (13) | |
H19A | 1.6639 | 0.4015 | 1.1187 | 0.045* | |
H19B | 1.7463 | 0.3167 | 1.0831 | 0.045* | |
H19C | 1.7245 | 0.3118 | 1.1843 | 0.045* | |
C20A | 1.8615 (5) | −0.2999 (5) | 1.1857 (4) | 0.0181 (10) | |
C21A | 1.8942 (7) | −0.2997 (7) | 1.2870 (4) | 0.0362 (15) | |
H21A | 1.9111 | −0.2099 | 1.3177 | 0.043* | |
H21B | 1.8171 | −0.3658 | 1.3062 | 0.043* | |
C22A | 1.9578 (6) | −0.3324 (7) | 1.1527 (5) | 0.0389 (16) | |
H22A | 1.9627 | −0.3396 | 1.0910 | 0.047* | |
C23A | 2.0553 (7) | −0.3551 (7) | 1.2317 (6) | 0.0453 (19) | |
C24A | 1.1064 (5) | 0.2701 (5) | 1.0319 (4) | 0.0188 (11) | |
H24A | 1.1055 | 0.2398 | 1.0933 | 0.023* | |
C25A | 1.1127 (5) | 0.4190 (5) | 1.0378 (4) | 0.0194 (11) | |
H25A | 1.0379 | 0.4243 | 1.0668 | 0.023* | |
C26A | 1.0884 (5) | 0.4656 (5) | 0.9435 (4) | 0.0188 (11) | |
H26A | 1.1712 | 0.4791 | 0.9181 | 0.023* | |
O1B | −0.2081 (5) | 1.4189 (5) | 0.3855 (3) | 0.0403 (11) | |
O2B | 0.5356 (3) | 0.7835 (3) | 0.6799 (3) | 0.0191 (8) | |
O3B | 0.4774 (4) | 0.5622 (4) | 0.7218 (3) | 0.0216 (8) | |
O4B | −0.2250 (8) | 1.5955 (7) | 0.4611 (4) | 0.0759 (14) | |
O5B | 0.0242 (4) | 1.1472 (4) | 0.4041 (2) | 0.0213 (8) | |
H5BB | −0.0468 | 1.0837 | 0.3783 | 0.032* | |
O6B | 0.7317 (4) | 0.7457 (4) | 0.5927 (3) | 0.0291 (9) | |
H6BB | 0.7478 | 0.7056 | 0.5502 | 0.044* | |
O7B | 0.8950 (4) | 0.6504 (4) | 0.7430 (3) | 0.0281 (9) | |
O8B | 0.7876 (4) | 0.6316 (4) | 0.9060 (3) | 0.0317 (10) | |
H8BB | 0.8599 | 0.6156 | 0.9087 | 0.048* | |
C1B | 0.5004 (5) | 1.0491 (6) | 0.6986 (4) | 0.0285 (13) | |
H1C | 0.5920 | 1.0473 | 0.6963 | 0.034* | |
H1D | 0.5138 | 1.1287 | 0.7403 | 0.034* | |
C2B | 0.4221 (6) | 0.9221 (6) | 0.7372 (4) | 0.0265 (13) | |
H2C | 0.3324 | 0.9254 | 0.7432 | 0.032* | |
H2D | 0.4746 | 0.9190 | 0.7982 | 0.032* | |
C3B | 0.3996 (5) | 0.7938 (5) | 0.6748 (4) | 0.0210 (11) | |
H3B | 0.3404 | 0.7138 | 0.6979 | 0.025* | |
C4B | 0.3288 (5) | 0.8023 (5) | 0.5762 (4) | 0.0196 (11) | |
H4C | 0.2336 | 0.7963 | 0.5748 | 0.024* | |
H4D | 0.3247 | 0.7242 | 0.5366 | 0.024* | |
C5B | 0.4025 (5) | 0.9334 (5) | 0.5370 (4) | 0.0217 (11) | |
H5B | 0.4946 | 0.9322 | 0.5327 | 0.026* | |
C6B | 0.3249 (6) | 0.9373 (7) | 0.4401 (4) | 0.0280 (13) | |
H6C | 0.3056 | 0.8515 | 0.4030 | 0.034* | |
H6D | 0.3840 | 1.0100 | 0.4124 | 0.034* | |
C7B | 0.1862 (6) | 0.9609 (6) | 0.4387 (4) | 0.0246 (12) | |
H7C | 0.1437 | 0.9684 | 0.3759 | 0.029* | |
H7D | 0.1225 | 0.8829 | 0.4594 | 0.029* | |
C8B | 0.2095 (5) | 1.0912 (5) | 0.5010 (4) | 0.0179 (10) | |
H8B | 0.2715 | 1.1678 | 0.4767 | 0.022* | |
C9B | 0.2878 (5) | 1.0856 (5) | 0.6007 (4) | 0.0185 (10) | |
H9B | 0.2287 | 1.0055 | 0.6237 | 0.022* | |
C10B | 0.4269 (5) | 1.0650 (5) | 0.6015 (4) | 0.0232 (12) | |
C11B | 0.3038 (6) | 1.2124 (6) | 0.6648 (4) | 0.0254 (12) | |
H11C | 0.3444 | 1.2031 | 0.7276 | 0.031* | |
H11D | 0.3672 | 1.2931 | 0.6464 | 0.031* | |
C12B | 0.1638 (5) | 1.2313 (5) | 0.6618 (4) | 0.0207 (11) | |
H12C | 0.1789 | 1.3124 | 0.7027 | 0.025* | |
H12D | 0.1025 | 1.1533 | 0.6841 | 0.025* | |
C13B | 0.0926 (5) | 1.2455 (5) | 0.5635 (4) | 0.0160 (10) | |
C14B | 0.0740 (5) | 1.1187 (5) | 0.4973 (4) | 0.0155 (10) | |
C15B | −0.0457 (5) | 1.0058 (5) | 0.5225 (4) | 0.0188 (10) | |
H15C | −0.0126 | 0.9694 | 0.5778 | 0.023* | |
H15D | −0.0900 | 0.9318 | 0.4725 | 0.023* | |
C16B | −0.1481 (5) | 1.0768 (5) | 0.5393 (4) | 0.0214 (11) | |
H16D | −0.1928 | 1.0387 | 0.5883 | 0.026* | |
H16C | −0.2198 | 1.0637 | 0.4836 | 0.026* | |
C17B | −0.0615 (5) | 1.2327 (5) | 0.5674 (4) | 0.0175 (10) | |
H17B | −0.0621 | 1.2552 | 0.6319 | 0.021* | |
C18B | 0.1757 (6) | 1.3818 (5) | 0.5347 (4) | 0.0253 (12) | |
H18D | 0.2705 | 1.3872 | 0.5393 | 0.038* | |
H18E | 0.1742 | 1.4557 | 0.5746 | 0.038* | |
H18F | 0.1346 | 1.3882 | 0.4721 | 0.038* | |
C19B | 0.5302 (6) | 1.1889 (6) | 0.5691 (6) | 0.0438 (18) | |
H19D | 0.6158 | 1.1730 | 0.5698 | 0.066* | |
H19E | 0.5489 | 1.2699 | 0.6099 | 0.066* | |
H19F | 0.4900 | 1.2007 | 0.5075 | 0.066* | |
C20B | −0.1154 (5) | 1.3242 (5) | 0.5121 (4) | 0.0217 (12) | |
C21B | −0.1601 (8) | 1.3080 (7) | 0.4073 (5) | 0.0450 (19) | |
H21D | −0.0820 | 1.3130 | 0.3798 | 0.054* | |
H21C | −0.2344 | 1.2208 | 0.3847 | 0.054* | |
C22B | −0.1371 (7) | 1.4347 (6) | 0.5417 (5) | 0.0360 (15) | |
H22B | −0.1181 | 1.4697 | 0.6034 | 0.043* | |
C23B | −0.1954 (8) | 1.4940 (8) | 0.4631 (5) | 0.047 (2) | |
C24B | 0.5289 (5) | 0.6500 (5) | 0.6571 (4) | 0.0182 (10) | |
H24B | 0.4664 | 0.6147 | 0.5961 | 0.022* | |
C25B | 0.6755 (6) | 0.6506 (5) | 0.6528 (4) | 0.0204 (11) | |
H25B | 0.6654 | 0.5593 | 0.6264 | 0.024* | |
C26B | 0.7710 (5) | 0.6802 (5) | 0.7465 (4) | 0.0195 (11) | |
H26B | 0.7968 | 0.7767 | 0.7698 | 0.023* | |
C27B | 0.7020 (5) | 0.5895 (5) | 0.8143 (4) | 0.0193 (11) | |
H27B | 0.6880 | 0.4938 | 0.7957 | 0.023* | |
C28B | 0.5644 (5) | 0.6042 (5) | 0.8149 (4) | 0.0202 (11) | |
H28B | 0.5785 | 0.6998 | 0.8339 | 0.024* | |
C29B | 0.4848 (7) | 0.5131 (7) | 0.8759 (5) | 0.0406 (16) | |
H29D | 0.3943 | 0.5206 | 0.8689 | 0.061* | |
H29E | 0.5349 | 0.5405 | 0.9391 | 0.061* | |
H29F | 0.4745 | 0.4200 | 0.8586 | 0.061* | |
C30B | 1.0100 (7) | 0.7617 (8) | 0.7294 (7) | 0.059 (2) | |
H30D | 1.0823 | 0.7290 | 0.7192 | 0.089* | |
H30E | 1.0453 | 0.8281 | 0.7831 | 0.089* | |
H30F | 0.9804 | 0.8031 | 0.6766 | 0.089* | |
C31 | 2.3709 (10) | −0.5541 (9) | 1.3384 (6) | 0.062 (2) | |
H31A | 2.3381 | −0.6241 | 1.3767 | 0.093* | |
H31B | 2.4672 | −0.5384 | 1.3392 | 0.093* | |
H31C | 2.3164 | −0.5828 | 1.2762 | 0.093* | |
O9 | 2.3575 (5) | −0.4312 (5) | 1.3724 (4) | 0.0484 (12) | |
H9AA | 2.3044 | −0.4033 | 1.3282 | 0.073* | |
O1W | 1.5908 (4) | −0.1956 (4) | 1.4173 (3) | 0.0291 (9) | |
H1W1 | 1.5342 | −0.2778 | 1.4074 | 0.044* | |
H2W1 | 1.6350 | −0.1811 | 1.4734 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.040 (3) | 0.049 (3) | 0.038 (3) | 0.024 (2) | −0.004 (2) | 0.000 (2) |
O2A | 0.0129 (16) | 0.0214 (18) | 0.0220 (19) | 0.0071 (14) | 0.0033 (15) | 0.0046 (16) |
O3A | 0.0135 (17) | 0.0221 (19) | 0.023 (2) | −0.0012 (15) | −0.0012 (15) | 0.0052 (16) |
O4A | 0.112 (4) | 0.101 (3) | 0.057 (3) | 0.089 (3) | 0.024 (3) | 0.007 (2) |
O5A | 0.0126 (16) | 0.0232 (18) | 0.0130 (17) | 0.0064 (14) | −0.0013 (14) | 0.0001 (15) |
O6A | 0.0195 (19) | 0.035 (2) | 0.029 (2) | 0.0093 (17) | −0.0141 (17) | −0.0133 (19) |
O7A | 0.025 (2) | 0.0203 (19) | 0.039 (2) | 0.0074 (16) | −0.0040 (18) | 0.0028 (18) |
O8A | 0.045 (3) | 0.035 (2) | 0.018 (2) | 0.020 (2) | −0.0017 (19) | 0.0039 (18) |
C1A | 0.028 (3) | 0.027 (3) | 0.023 (3) | 0.017 (2) | 0.007 (2) | 0.012 (2) |
C2A | 0.035 (3) | 0.031 (3) | 0.015 (3) | 0.019 (3) | 0.001 (2) | 0.002 (2) |
C3A | 0.019 (2) | 0.020 (3) | 0.023 (3) | 0.012 (2) | −0.002 (2) | 0.004 (2) |
C4A | 0.015 (2) | 0.020 (3) | 0.024 (3) | 0.008 (2) | 0.001 (2) | 0.007 (2) |
C5A | 0.019 (2) | 0.018 (2) | 0.021 (3) | 0.009 (2) | 0.003 (2) | 0.003 (2) |
C6A | 0.024 (3) | 0.031 (3) | 0.018 (3) | 0.019 (2) | 0.003 (2) | 0.002 (2) |
C7A | 0.023 (3) | 0.029 (3) | 0.016 (3) | 0.017 (2) | 0.003 (2) | 0.006 (2) |
C8A | 0.018 (2) | 0.014 (2) | 0.017 (3) | 0.003 (2) | 0.006 (2) | 0.002 (2) |
C9A | 0.013 (2) | 0.018 (2) | 0.019 (3) | 0.0062 (19) | 0.002 (2) | 0.005 (2) |
C10A | 0.013 (2) | 0.015 (2) | 0.024 (3) | 0.007 (2) | 0.003 (2) | 0.009 (2) |
C11A | 0.035 (3) | 0.034 (3) | 0.016 (3) | 0.019 (3) | 0.013 (2) | 0.010 (2) |
C12A | 0.025 (3) | 0.030 (3) | 0.016 (3) | 0.016 (2) | 0.006 (2) | 0.005 (2) |
C13A | 0.018 (2) | 0.015 (2) | 0.016 (2) | 0.006 (2) | 0.005 (2) | 0.002 (2) |
C14A | 0.013 (2) | 0.017 (2) | 0.011 (2) | 0.008 (2) | −0.0010 (19) | 0.006 (2) |
C15A | 0.012 (2) | 0.017 (2) | 0.023 (3) | 0.003 (2) | 0.001 (2) | 0.003 (2) |
C16A | 0.012 (2) | 0.018 (3) | 0.040 (3) | 0.002 (2) | 0.002 (2) | −0.001 (2) |
C27A | 0.015 (2) | 0.029 (3) | 0.015 (3) | 0.008 (2) | −0.002 (2) | 0.004 (2) |
C28A | 0.014 (2) | 0.029 (3) | 0.022 (3) | 0.005 (2) | −0.003 (2) | −0.001 (2) |
C29A | 0.034 (3) | 0.029 (3) | 0.035 (4) | 0.000 (3) | −0.005 (3) | −0.004 (3) |
C30A | 0.045 (4) | 0.022 (3) | 0.090 (7) | −0.006 (3) | 0.000 (4) | 0.006 (4) |
C17A | 0.018 (2) | 0.020 (3) | 0.017 (3) | 0.007 (2) | 0.002 (2) | 0.000 (2) |
C18A | 0.016 (2) | 0.023 (3) | 0.028 (3) | 0.004 (2) | 0.008 (2) | 0.001 (2) |
C19A | 0.018 (3) | 0.020 (3) | 0.049 (4) | 0.003 (2) | 0.004 (3) | 0.005 (3) |
C20A | 0.018 (2) | 0.013 (2) | 0.020 (3) | 0.0045 (19) | −0.001 (2) | −0.001 (2) |
C21A | 0.034 (3) | 0.048 (4) | 0.028 (3) | 0.019 (3) | 0.002 (3) | 0.015 (3) |
C22A | 0.033 (3) | 0.052 (4) | 0.034 (4) | 0.026 (3) | −0.003 (3) | −0.017 (3) |
C23A | 0.030 (3) | 0.037 (4) | 0.062 (5) | 0.026 (3) | −0.022 (3) | −0.019 (3) |
C24A | 0.011 (2) | 0.027 (3) | 0.017 (3) | 0.007 (2) | −0.001 (2) | 0.006 (2) |
C25A | 0.013 (2) | 0.026 (3) | 0.016 (3) | 0.006 (2) | −0.004 (2) | −0.003 (2) |
C26A | 0.015 (2) | 0.019 (3) | 0.023 (3) | 0.010 (2) | 0.000 (2) | 0.004 (2) |
O1B | 0.045 (3) | 0.038 (2) | 0.040 (3) | 0.021 (2) | 0.002 (2) | 0.010 (2) |
O2B | 0.0135 (16) | 0.0148 (17) | 0.027 (2) | 0.0057 (14) | −0.0009 (15) | 0.0028 (15) |
O3B | 0.0183 (17) | 0.0172 (17) | 0.025 (2) | 0.0028 (15) | 0.0000 (16) | 0.0060 (16) |
O4B | 0.112 (4) | 0.101 (3) | 0.057 (3) | 0.089 (3) | 0.024 (3) | 0.007 (2) |
O5B | 0.0225 (18) | 0.0238 (19) | 0.0169 (19) | 0.0101 (16) | −0.0010 (15) | 0.0043 (16) |
O6B | 0.033 (2) | 0.030 (2) | 0.028 (2) | 0.0107 (18) | 0.0134 (18) | 0.0148 (18) |
O7B | 0.0199 (19) | 0.033 (2) | 0.036 (2) | 0.0126 (17) | 0.0073 (17) | 0.0139 (19) |
O8B | 0.031 (2) | 0.050 (3) | 0.018 (2) | 0.023 (2) | −0.0019 (17) | 0.0032 (19) |
C1B | 0.011 (2) | 0.025 (3) | 0.042 (4) | 0.009 (2) | −0.012 (2) | −0.012 (3) |
C2B | 0.026 (3) | 0.037 (3) | 0.020 (3) | 0.023 (3) | −0.006 (2) | −0.003 (2) |
C3B | 0.018 (2) | 0.021 (3) | 0.025 (3) | 0.008 (2) | 0.005 (2) | 0.004 (2) |
C4B | 0.015 (2) | 0.019 (3) | 0.024 (3) | 0.008 (2) | −0.001 (2) | −0.001 (2) |
C5B | 0.016 (2) | 0.023 (3) | 0.028 (3) | 0.009 (2) | 0.006 (2) | 0.004 (2) |
C6B | 0.036 (3) | 0.042 (3) | 0.022 (3) | 0.028 (3) | 0.014 (3) | 0.010 (3) |
C7B | 0.034 (3) | 0.034 (3) | 0.016 (3) | 0.027 (3) | 0.001 (2) | −0.001 (2) |
C8B | 0.018 (2) | 0.017 (2) | 0.021 (3) | 0.009 (2) | 0.006 (2) | 0.004 (2) |
C9B | 0.014 (2) | 0.016 (2) | 0.024 (3) | 0.0039 (19) | 0.003 (2) | −0.001 (2) |
C10B | 0.016 (2) | 0.020 (3) | 0.033 (3) | 0.007 (2) | 0.003 (2) | 0.002 (2) |
C11B | 0.018 (3) | 0.024 (3) | 0.028 (3) | 0.008 (2) | −0.008 (2) | −0.008 (2) |
C12B | 0.021 (3) | 0.019 (3) | 0.019 (3) | 0.009 (2) | −0.003 (2) | −0.004 (2) |
C13B | 0.013 (2) | 0.013 (2) | 0.021 (3) | 0.0044 (19) | 0.002 (2) | −0.002 (2) |
C14B | 0.017 (2) | 0.015 (2) | 0.015 (2) | 0.008 (2) | 0.001 (2) | 0.003 (2) |
C15B | 0.017 (2) | 0.016 (2) | 0.019 (3) | 0.002 (2) | 0.001 (2) | 0.000 (2) |
C16B | 0.015 (2) | 0.014 (2) | 0.033 (3) | 0.001 (2) | 0.007 (2) | 0.002 (2) |
C17B | 0.016 (2) | 0.016 (2) | 0.019 (3) | 0.004 (2) | 0.005 (2) | 0.000 (2) |
C18B | 0.020 (3) | 0.015 (3) | 0.038 (3) | 0.002 (2) | 0.007 (2) | 0.002 (2) |
C19B | 0.021 (3) | 0.028 (3) | 0.084 (6) | 0.005 (2) | 0.020 (3) | 0.014 (4) |
C20B | 0.011 (2) | 0.018 (3) | 0.035 (3) | 0.004 (2) | 0.004 (2) | 0.004 (2) |
C21B | 0.051 (4) | 0.034 (4) | 0.042 (4) | 0.023 (3) | −0.022 (3) | −0.004 (3) |
C22B | 0.053 (4) | 0.033 (3) | 0.040 (4) | 0.027 (3) | 0.029 (3) | 0.014 (3) |
C23B | 0.072 (5) | 0.049 (4) | 0.058 (5) | 0.049 (4) | 0.046 (4) | 0.036 (4) |
C24B | 0.021 (2) | 0.013 (2) | 0.018 (3) | 0.007 (2) | −0.002 (2) | 0.004 (2) |
C25B | 0.029 (3) | 0.015 (2) | 0.022 (3) | 0.010 (2) | 0.010 (2) | 0.007 (2) |
C26B | 0.016 (2) | 0.017 (2) | 0.028 (3) | 0.007 (2) | 0.005 (2) | 0.006 (2) |
C27B | 0.021 (2) | 0.021 (3) | 0.016 (3) | 0.009 (2) | 0.002 (2) | 0.001 (2) |
C28B | 0.016 (2) | 0.019 (3) | 0.023 (3) | 0.002 (2) | 0.004 (2) | 0.004 (2) |
C29B | 0.043 (4) | 0.040 (4) | 0.041 (4) | 0.010 (3) | 0.020 (3) | 0.021 (3) |
C30B | 0.023 (3) | 0.066 (5) | 0.088 (6) | 0.008 (3) | 0.017 (4) | 0.046 (5) |
C31 | 0.085 (6) | 0.059 (5) | 0.058 (5) | 0.042 (5) | 0.020 (5) | 0.012 (4) |
O9 | 0.038 (3) | 0.044 (3) | 0.056 (3) | 0.011 (2) | 0.000 (2) | 0.003 (2) |
O1W | 0.029 (2) | 0.033 (2) | 0.023 (2) | 0.0081 (18) | 0.0046 (17) | 0.0064 (18) |
O1A—C23A | 1.336 (10) | O3B—C24B | 1.416 (6) |
O1A—C21A | 1.423 (7) | O3B—C28B | 1.454 (6) |
O2A—C24A | 1.405 (6) | O4B—C23B | 1.200 (8) |
O2A—C3A | 1.452 (6) | O5B—C14B | 1.461 (6) |
O3A—C24A | 1.418 (6) | O5B—H5BB | 0.8200 |
O3A—C28A | 1.430 (6) | O6B—C25B | 1.422 (6) |
O4A—C23A | 1.204 (8) | O6B—H6BB | 0.8200 |
O5A—C14A | 1.456 (5) | O7B—C30B | 1.419 (8) |
O5A—H5AA | 0.8200 | O7B—C26B | 1.439 (6) |
O6A—C25A | 1.412 (6) | O8B—C27B | 1.433 (6) |
O6A—H6AA | 0.8200 | O8B—H8BB | 0.8200 |
O7A—C30A | 1.442 (8) | C1B—C2B | 1.512 (9) |
O7A—C26A | 1.449 (6) | C1B—C10B | 1.538 (8) |
O8A—C27A | 1.410 (6) | C1B—H1C | 0.9700 |
O8A—H8AA | 0.8200 | C1B—H1D | 0.9700 |
C1A—C2A | 1.522 (8) | C2B—C3B | 1.520 (8) |
C1A—C10A | 1.542 (7) | C2B—H2C | 0.9700 |
C1A—H1A | 0.9700 | C2B—H2D | 0.9700 |
C1A—H1B | 0.9700 | C3B—C4B | 1.526 (7) |
C2A—C3A | 1.523 (8) | C3B—H3B | 0.9800 |
C2A—H2A | 0.9700 | C4B—C5B | 1.532 (7) |
C2A—H2B | 0.9700 | C4B—H4C | 0.9700 |
C3A—C4A | 1.522 (7) | C4B—H4D | 0.9700 |
C3A—H3A | 0.9800 | C5B—C6B | 1.515 (7) |
C4A—C5A | 1.553 (7) | C5B—C10B | 1.561 (8) |
C4A—H4A | 0.9700 | C5B—H5B | 0.9800 |
C4A—H4B | 0.9700 | C6B—C7B | 1.544 (7) |
C5A—C6A | 1.525 (7) | C6B—H6C | 0.9700 |
C5A—C10A | 1.557 (7) | C6B—H6D | 0.9700 |
C5A—H5A | 0.9800 | C7B—C8B | 1.535 (7) |
C6A—C7A | 1.527 (7) | C7B—H7C | 0.9700 |
C6A—H6A | 0.9700 | C7B—H7D | 0.9700 |
C6A—H6B | 0.9700 | C8B—C14B | 1.525 (7) |
C7A—C8A | 1.540 (7) | C8B—C9B | 1.558 (7) |
C7A—H7A | 0.9700 | C8B—H8B | 0.9800 |
C7A—H7B | 0.9700 | C9B—C10B | 1.534 (7) |
C8A—C14A | 1.541 (6) | C9B—C11B | 1.541 (7) |
C8A—C9A | 1.543 (7) | C9B—H9B | 0.9800 |
C8A—H8A | 0.9800 | C10B—C19B | 1.548 (8) |
C9A—C11A | 1.517 (7) | C11B—C12B | 1.531 (7) |
C9A—C10A | 1.553 (7) | C11B—H11C | 0.9700 |
C9A—H9A | 0.9800 | C11B—H11D | 0.9700 |
C10A—C19A | 1.543 (7) | C12B—C13B | 1.541 (7) |
C11A—C12A | 1.530 (7) | C12B—H12C | 0.9700 |
C11A—H11A | 0.9700 | C12B—H12D | 0.9700 |
C11A—H11B | 0.9700 | C13B—C18B | 1.527 (7) |
C12A—C13A | 1.539 (7) | C13B—C14B | 1.552 (7) |
C12A—H12B | 0.9700 | C13B—C17B | 1.581 (7) |
C12A—H12A | 0.9700 | C14B—C15B | 1.526 (7) |
C13A—C18A | 1.520 (7) | C15B—C16B | 1.541 (7) |
C13A—C14A | 1.566 (7) | C15B—H15C | 0.9700 |
C13A—C17A | 1.567 (7) | C15B—H15D | 0.9700 |
C14A—C15A | 1.531 (7) | C16B—C17B | 1.565 (7) |
C15A—C16A | 1.529 (7) | C16B—H16D | 0.9700 |
C15A—H15A | 0.9700 | C16B—H16C | 0.9700 |
C15A—H15B | 0.9700 | C17B—C20B | 1.467 (7) |
C16A—C17A | 1.549 (7) | C17B—H17B | 0.9800 |
C16A—H16A | 0.9700 | C18B—H18D | 0.9600 |
C16A—H16B | 0.9700 | C18B—H18E | 0.9600 |
C27A—C28A | 1.519 (7) | C18B—H18F | 0.9600 |
C27A—C26A | 1.525 (7) | C19B—H19D | 0.9600 |
C27A—H27A | 0.9800 | C19B—H19E | 0.9600 |
C28A—C29A | 1.512 (8) | C19B—H19F | 0.9600 |
C28A—H28A | 0.9800 | C20B—C22B | 1.323 (8) |
C29A—H29A | 0.9600 | C20B—C21B | 1.520 (9) |
C29A—H29B | 0.9600 | C21B—H21D | 0.9700 |
C29A—H29C | 0.9600 | C21B—H21C | 0.9700 |
C30A—H30A | 0.9600 | C22B—C23B | 1.467 (9) |
C30A—H30B | 0.9600 | C22B—H22B | 0.9300 |
C30A—H30C | 0.9600 | C24B—C25B | 1.542 (7) |
C17A—C20A | 1.502 (7) | C24B—H24B | 0.9800 |
C17A—H17A | 0.9800 | C25B—C26B | 1.495 (7) |
C18A—H18A | 0.9600 | C25B—H25B | 0.9800 |
C18A—H18B | 0.9600 | C26B—C27B | 1.531 (7) |
C18A—H18C | 0.9600 | C26B—H26B | 0.9800 |
C19A—H19A | 0.9600 | C27B—C28B | 1.496 (7) |
C19A—H19B | 0.9600 | C27B—H27B | 0.9800 |
C19A—H19C | 0.9600 | C28B—C29B | 1.504 (8) |
C20A—C22A | 1.333 (8) | C28B—H28B | 0.9800 |
C20A—C21A | 1.478 (8) | C29B—H29D | 0.9600 |
C21A—H21A | 0.9700 | C29B—H29E | 0.9600 |
C21A—H21B | 0.9700 | C29B—H29F | 0.9600 |
C22A—C23A | 1.478 (9) | C30B—H30D | 0.9600 |
C22A—H22A | 0.9300 | C30B—H30E | 0.9600 |
C24A—C25A | 1.533 (7) | C30B—H30F | 0.9600 |
C24A—H24A | 0.9800 | C31—O9 | 1.421 (9) |
C25A—C26A | 1.505 (7) | C31—H31A | 0.9600 |
C25A—H25A | 0.9800 | C31—H31B | 0.9600 |
C26A—H26A | 0.9800 | C31—H31C | 0.9600 |
O1B—C23B | 1.327 (9) | O9—H9AA | 0.8967 |
O1B—C21B | 1.434 (7) | O1W—H1W1 | 0.8500 |
O2B—C24B | 1.398 (6) | O1W—H2W1 | 0.8500 |
O2B—C3B | 1.446 (6) | ||
C23A—O1A—C21A | 108.3 (5) | C25B—O6B—H6BB | 109.5 |
C24A—O2A—C3A | 112.8 (4) | C30B—O7B—C26B | 115.7 (5) |
C24A—O3A—C28A | 112.7 (4) | C27B—O8B—H8BB | 109.5 |
C14A—O5A—H5AA | 109.5 | C2B—C1B—C10B | 114.1 (4) |
C25A—O6A—H6AA | 109.5 | C2B—C1B—H1C | 108.7 |
C30A—O7A—C26A | 114.6 (5) | C10B—C1B—H1C | 108.7 |
C27A—O8A—H8AA | 109.5 | C2B—C1B—H1D | 108.7 |
C2A—C1A—C10A | 115.0 (4) | C10B—C1B—H1D | 108.7 |
C2A—C1A—H1A | 108.5 | H1C—C1B—H1D | 107.6 |
C10A—C1A—H1A | 108.5 | C1B—C2B—C3B | 111.0 (5) |
C2A—C1A—H1B | 108.5 | C1B—C2B—H2C | 109.4 |
C10A—C1A—H1B | 108.5 | C3B—C2B—H2C | 109.4 |
H1A—C1A—H1B | 107.5 | C1B—C2B—H2D | 109.4 |
C1A—C2A—C3A | 110.5 (5) | C3B—C2B—H2D | 109.4 |
C1A—C2A—H2A | 109.5 | H2C—C2B—H2D | 108.0 |
C3A—C2A—H2A | 109.5 | O2B—C3B—C2B | 106.8 (4) |
C1A—C2A—H2B | 109.5 | O2B—C3B—C4B | 111.8 (4) |
C3A—C2A—H2B | 109.5 | C2B—C3B—C4B | 110.4 (4) |
H2A—C2A—H2B | 108.1 | O2B—C3B—H3B | 109.3 |
O2A—C3A—C4A | 111.5 (4) | C2B—C3B—H3B | 109.3 |
O2A—C3A—C2A | 106.3 (4) | C4B—C3B—H3B | 109.3 |
C4A—C3A—C2A | 110.7 (4) | C3B—C4B—C5B | 114.0 (4) |
O2A—C3A—H3A | 109.4 | C3B—C4B—H4C | 108.7 |
C4A—C3A—H3A | 109.4 | C5B—C4B—H4C | 108.7 |
C2A—C3A—H3A | 109.4 | C3B—C4B—H4D | 108.7 |
C3A—C4A—C5A | 113.5 (4) | C5B—C4B—H4D | 108.7 |
C3A—C4A—H4A | 108.9 | H4C—C4B—H4D | 107.6 |
C5A—C4A—H4A | 108.9 | C6B—C5B—C4B | 111.4 (4) |
C3A—C4A—H4B | 108.9 | C6B—C5B—C10B | 111.2 (4) |
C5A—C4A—H4B | 108.9 | C4B—C5B—C10B | 112.3 (4) |
H4A—C4A—H4B | 107.7 | C6B—C5B—H5B | 107.2 |
C6A—C5A—C4A | 111.0 (4) | C4B—C5B—H5B | 107.2 |
C6A—C5A—C10A | 112.3 (4) | C10B—C5B—H5B | 107.2 |
C4A—C5A—C10A | 112.6 (4) | C5B—C6B—C7B | 112.5 (4) |
C6A—C5A—H5A | 106.8 | C5B—C6B—H6C | 109.1 |
C4A—C5A—H5A | 106.8 | C7B—C6B—H6C | 109.1 |
C10A—C5A—H5A | 106.8 | C5B—C6B—H6D | 109.1 |
C5A—C6A—C7A | 112.1 (4) | C7B—C6B—H6D | 109.1 |
C5A—C6A—H6A | 109.2 | H6C—C6B—H6D | 107.8 |
C7A—C6A—H6A | 109.2 | C8B—C7B—C6B | 111.4 (5) |
C5A—C6A—H6B | 109.2 | C8B—C7B—H7C | 109.3 |
C7A—C6A—H6B | 109.2 | C6B—C7B—H7C | 109.3 |
H6A—C6A—H6B | 107.9 | C8B—C7B—H7D | 109.3 |
C6A—C7A—C8A | 112.6 (4) | C6B—C7B—H7D | 109.3 |
C6A—C7A—H7A | 109.1 | H7C—C7B—H7D | 108.0 |
C8A—C7A—H7A | 109.1 | C14B—C8B—C7B | 111.9 (4) |
C6A—C7A—H7B | 109.1 | C14B—C8B—C9B | 113.7 (4) |
C8A—C7A—H7B | 109.1 | C7B—C8B—C9B | 110.0 (4) |
H7A—C7A—H7B | 107.8 | C14B—C8B—H8B | 106.9 |
C7A—C8A—C14A | 111.4 (4) | C7B—C8B—H8B | 106.9 |
C7A—C8A—C9A | 109.6 (4) | C9B—C8B—H8B | 106.9 |
C14A—C8A—C9A | 114.8 (4) | C10B—C9B—C11B | 113.2 (4) |
C7A—C8A—H8A | 106.9 | C10B—C9B—C8B | 111.8 (4) |
C14A—C8A—H8A | 106.9 | C11B—C9B—C8B | 110.2 (4) |
C9A—C8A—H8A | 106.9 | C10B—C9B—H9B | 107.1 |
C11A—C9A—C8A | 111.4 (4) | C11B—C9B—H9B | 107.1 |
C11A—C9A—C10A | 113.9 (4) | C8B—C9B—H9B | 107.1 |
C8A—C9A—C10A | 111.5 (4) | C9B—C10B—C1B | 112.4 (5) |
C11A—C9A—H9A | 106.5 | C9B—C10B—C19B | 111.2 (4) |
C8A—C9A—H9A | 106.5 | C1B—C10B—C19B | 106.5 (5) |
C10A—C9A—H9A | 106.5 | C9B—C10B—C5B | 110.4 (4) |
C1A—C10A—C19A | 106.3 (4) | C1B—C10B—C5B | 107.4 (4) |
C1A—C10A—C9A | 112.7 (4) | C19B—C10B—C5B | 108.8 (5) |
C19A—C10A—C9A | 111.3 (4) | C12B—C11B—C9B | 112.1 (4) |
C1A—C10A—C5A | 107.7 (4) | C12B—C11B—H11C | 109.2 |
C19A—C10A—C5A | 108.8 (4) | C9B—C11B—H11C | 109.2 |
C9A—C10A—C5A | 109.8 (4) | C12B—C11B—H11D | 109.2 |
C9A—C11A—C12A | 112.2 (4) | C9B—C11B—H11D | 109.2 |
C9A—C11A—H11A | 109.2 | H11C—C11B—H11D | 107.9 |
C12A—C11A—H11A | 109.2 | C11B—C12B—C13B | 112.0 (4) |
C9A—C11A—H11B | 109.2 | C11B—C12B—H12C | 109.2 |
C12A—C11A—H11B | 109.2 | C13B—C12B—H12C | 109.2 |
H11A—C11A—H11B | 107.9 | C11B—C12B—H12D | 109.2 |
C11A—C12A—C13A | 114.0 (4) | C13B—C12B—H12D | 109.2 |
C11A—C12A—H12B | 108.8 | H12C—C12B—H12D | 107.9 |
C13A—C12A—H12B | 108.8 | C18B—C13B—C12B | 109.5 (4) |
C11A—C12A—H12A | 108.8 | C18B—C13B—C14B | 114.1 (4) |
C13A—C12A—H12A | 108.8 | C12B—C13B—C14B | 109.3 (4) |
H12B—C12A—H12A | 107.6 | C18B—C13B—C17B | 113.3 (4) |
C18A—C13A—C12A | 109.5 (4) | C12B—C13B—C17B | 105.9 (4) |
C18A—C13A—C14A | 112.8 (4) | C14B—C13B—C17B | 104.3 (4) |
C12A—C13A—C14A | 108.6 (4) | O5B—C14B—C8B | 108.6 (4) |
C18A—C13A—C17A | 114.7 (4) | O5B—C14B—C15B | 107.8 (4) |
C12A—C13A—C17A | 107.1 (4) | C8B—C14B—C15B | 116.9 (4) |
C14A—C13A—C17A | 103.8 (4) | O5B—C14B—C13B | 106.4 (4) |
O5A—C14A—C15A | 109.3 (4) | C8B—C14B—C13B | 113.2 (4) |
O5A—C14A—C8A | 108.6 (4) | C15B—C14B—C13B | 103.3 (4) |
C15A—C14A—C8A | 115.9 (4) | C14B—C15B—C16B | 104.4 (4) |
O5A—C14A—C13A | 105.7 (3) | C14B—C15B—H15C | 110.9 |
C15A—C14A—C13A | 102.8 (4) | C16B—C15B—H15C | 110.9 |
C8A—C14A—C13A | 114.0 (4) | C14B—C15B—H15D | 110.9 |
C16A—C15A—C14A | 105.7 (4) | C16B—C15B—H15D | 110.9 |
C16A—C15A—H15A | 110.6 | H15C—C15B—H15D | 108.9 |
C14A—C15A—H15A | 110.6 | C15B—C16B—C17B | 107.4 (4) |
C16A—C15A—H15B | 110.6 | C15B—C16B—H16D | 110.2 |
C14A—C15A—H15B | 110.6 | C17B—C16B—H16D | 110.2 |
H15A—C15A—H15B | 108.7 | C15B—C16B—H16C | 110.2 |
C15A—C16A—C17A | 106.5 (4) | C17B—C16B—H16C | 110.2 |
C15A—C16A—H16A | 110.4 | H16D—C16B—H16C | 108.5 |
C17A—C16A—H16A | 110.4 | C20B—C17B—C16B | 114.6 (4) |
C15A—C16A—H16B | 110.4 | C20B—C17B—C13B | 114.3 (4) |
C17A—C16A—H16B | 110.4 | C16B—C17B—C13B | 104.2 (4) |
H16A—C16A—H16B | 108.6 | C20B—C17B—H17B | 107.8 |
O8A—C27A—C28A | 109.1 (4) | C16B—C17B—H17B | 107.8 |
O8A—C27A—C26A | 111.9 (4) | C13B—C17B—H17B | 107.8 |
C28A—C27A—C26A | 109.0 (4) | C13B—C18B—H18D | 109.5 |
O8A—C27A—H27A | 109.0 | C13B—C18B—H18E | 109.5 |
C28A—C27A—H27A | 109.0 | H18D—C18B—H18E | 109.5 |
C26A—C27A—H27A | 109.0 | C13B—C18B—H18F | 109.5 |
O3A—C28A—C29A | 106.4 (5) | H18D—C18B—H18F | 109.5 |
O3A—C28A—C27A | 108.7 (4) | H18E—C18B—H18F | 109.5 |
C29A—C28A—C27A | 112.9 (4) | C10B—C19B—H19D | 109.5 |
O3A—C28A—H28A | 109.6 | C10B—C19B—H19E | 109.5 |
C29A—C28A—H28A | 109.6 | H19D—C19B—H19E | 109.5 |
C27A—C28A—H28A | 109.6 | C10B—C19B—H19F | 109.5 |
C28A—C29A—H29A | 109.5 | H19D—C19B—H19F | 109.5 |
C28A—C29A—H29B | 109.5 | H19E—C19B—H19F | 109.5 |
H29A—C29A—H29B | 109.5 | C22B—C20B—C17B | 127.9 (6) |
C28A—C29A—H29C | 109.5 | C22B—C20B—C21B | 106.1 (5) |
H29A—C29A—H29C | 109.5 | C17B—C20B—C21B | 125.9 (5) |
H29B—C29A—H29C | 109.5 | O1B—C21B—C20B | 105.6 (5) |
O7A—C30A—H30A | 109.5 | O1B—C21B—H21D | 110.6 |
O7A—C30A—H30B | 109.5 | C20B—C21B—H21D | 110.6 |
H30A—C30A—H30B | 109.5 | O1B—C21B—H21C | 110.6 |
O7A—C30A—H30C | 109.5 | C20B—C21B—H21C | 110.6 |
H30A—C30A—H30C | 109.5 | H21D—C21B—H21C | 108.8 |
H30B—C30A—H30C | 109.5 | C20B—C22B—C23B | 110.1 (6) |
C20A—C17A—C16A | 112.6 (4) | C20B—C22B—H22B | 125.0 |
C20A—C17A—C13A | 115.9 (4) | C23B—C22B—H22B | 125.0 |
C16A—C17A—C13A | 106.2 (4) | O4B—C23B—O1B | 120.7 (7) |
C20A—C17A—H17A | 107.2 | O4B—C23B—C22B | 130.3 (8) |
C16A—C17A—H17A | 107.2 | O1B—C23B—C22B | 109.0 (5) |
C13A—C17A—H17A | 107.2 | O2B—C24B—O3B | 111.9 (4) |
C13A—C18A—H18A | 109.5 | O2B—C24B—C25B | 109.6 (4) |
C13A—C18A—H18B | 109.5 | O3B—C24B—C25B | 109.2 (4) |
H18A—C18A—H18B | 109.5 | O2B—C24B—H24B | 108.7 |
C13A—C18A—H18C | 109.5 | O3B—C24B—H24B | 108.7 |
H18A—C18A—H18C | 109.5 | C25B—C24B—H24B | 108.7 |
H18B—C18A—H18C | 109.5 | O6B—C25B—C26B | 111.5 (4) |
C10A—C19A—H19A | 109.5 | O6B—C25B—C24B | 109.5 (4) |
C10A—C19A—H19B | 109.5 | C26B—C25B—C24B | 112.1 (4) |
H19A—C19A—H19B | 109.5 | O6B—C25B—H25B | 107.9 |
C10A—C19A—H19C | 109.5 | C26B—C25B—H25B | 107.9 |
H19A—C19A—H19C | 109.5 | C24B—C25B—H25B | 107.9 |
H19B—C19A—H19C | 109.5 | O7B—C26B—C25B | 110.7 (4) |
C22A—C20A—C21A | 107.9 (5) | O7B—C26B—C27B | 106.0 (4) |
C22A—C20A—C17A | 127.1 (5) | C25B—C26B—C27B | 111.2 (4) |
C21A—C20A—C17A | 124.9 (5) | O7B—C26B—H26B | 109.6 |
O1A—C21A—C20A | 106.7 (5) | C25B—C26B—H26B | 109.6 |
O1A—C21A—H21A | 110.4 | C27B—C26B—H26B | 109.6 |
C20A—C21A—H21A | 110.4 | O8B—C27B—C28B | 107.9 (4) |
O1A—C21A—H21B | 110.4 | O8B—C27B—C26B | 110.2 (4) |
C20A—C21A—H21B | 110.4 | C28B—C27B—C26B | 109.4 (4) |
H21A—C21A—H21B | 108.6 | O8B—C27B—H27B | 109.8 |
C20A—C22A—C23A | 107.7 (6) | C28B—C27B—H27B | 109.8 |
C20A—C22A—H22A | 126.2 | C26B—C27B—H27B | 109.8 |
C23A—C22A—H22A | 126.2 | O3B—C28B—C27B | 108.1 (4) |
O4A—C23A—O1A | 119.2 (7) | O3B—C28B—C29B | 105.9 (4) |
O4A—C23A—C22A | 131.3 (8) | C27B—C28B—C29B | 113.4 (5) |
O1A—C23A—C22A | 109.4 (5) | O3B—C28B—H28B | 109.8 |
O2A—C24A—O3A | 112.2 (4) | C27B—C28B—H28B | 109.8 |
O2A—C24A—C25A | 109.7 (4) | C29B—C28B—H28B | 109.8 |
O3A—C24A—C25A | 109.7 (4) | C28B—C29B—H29D | 109.5 |
O2A—C24A—H24A | 108.4 | C28B—C29B—H29E | 109.5 |
O3A—C24A—H24A | 108.4 | H29D—C29B—H29E | 109.5 |
C25A—C24A—H24A | 108.4 | C28B—C29B—H29F | 109.5 |
O6A—C25A—C26A | 111.5 (4) | H29D—C29B—H29F | 109.5 |
O6A—C25A—C24A | 110.2 (4) | H29E—C29B—H29F | 109.5 |
C26A—C25A—C24A | 111.7 (4) | O7B—C30B—H30D | 109.5 |
O6A—C25A—H25A | 107.7 | O7B—C30B—H30E | 109.5 |
C26A—C25A—H25A | 107.7 | H30D—C30B—H30E | 109.5 |
C24A—C25A—H25A | 107.7 | O7B—C30B—H30F | 109.5 |
O7A—C26A—C25A | 111.2 (4) | H30D—C30B—H30F | 109.5 |
O7A—C26A—C27A | 105.4 (4) | H30E—C30B—H30F | 109.5 |
C25A—C26A—C27A | 112.2 (4) | O9—C31—H31A | 109.5 |
O7A—C26A—H26A | 109.3 | O9—C31—H31B | 109.5 |
C25A—C26A—H26A | 109.3 | H31A—C31—H31B | 109.5 |
C27A—C26A—H26A | 109.3 | O9—C31—H31C | 109.5 |
C23B—O1B—C21B | 109.2 (5) | H31A—C31—H31C | 109.5 |
C24B—O2B—C3B | 112.9 (4) | H31B—C31—H31C | 109.5 |
C24B—O3B—C28B | 113.2 (4) | C31—O9—H9AA | 110.1 |
C14B—O5B—H5BB | 109.5 | H1W1—O1W—H2W1 | 107.7 |
C10A—C1A—C2A—C3A | 57.9 (6) | C10B—C1B—C2B—C3B | 59.0 (6) |
C24A—O2A—C3A—C4A | −79.7 (5) | C24B—O2B—C3B—C2B | 156.6 (4) |
C24A—O2A—C3A—C2A | 159.6 (4) | C24B—O2B—C3B—C4B | −82.6 (5) |
C1A—C2A—C3A—O2A | 66.6 (5) | C1B—C2B—C3B—O2B | 67.8 (5) |
C1A—C2A—C3A—C4A | −54.6 (6) | C1B—C2B—C3B—C4B | −53.9 (6) |
O2A—C3A—C4A—C5A | −64.5 (5) | O2B—C3B—C4B—C5B | −66.3 (5) |
C2A—C3A—C4A—C5A | 53.6 (6) | C2B—C3B—C4B—C5B | 52.4 (6) |
C3A—C4A—C5A—C6A | −179.9 (4) | C3B—C4B—C5B—C6B | −178.4 (4) |
C3A—C4A—C5A—C10A | −53.0 (6) | C3B—C4B—C5B—C10B | −52.9 (6) |
C4A—C5A—C6A—C7A | 74.2 (5) | C4B—C5B—C6B—C7B | 71.4 (6) |
C10A—C5A—C6A—C7A | −52.9 (6) | C10B—C5B—C6B—C7B | −54.7 (6) |
C5A—C6A—C7A—C8A | 54.0 (6) | C5B—C6B—C7B—C8B | 55.4 (6) |
C6A—C7A—C8A—C14A | 176.1 (4) | C6B—C7B—C8B—C14B | 177.8 (4) |
C6A—C7A—C8A—C9A | −55.8 (6) | C6B—C7B—C8B—C9B | −54.8 (6) |
C7A—C8A—C9A—C11A | −174.0 (4) | C14B—C8B—C9B—C10B | −177.1 (4) |
C14A—C8A—C9A—C11A | −47.8 (6) | C7B—C8B—C9B—C10B | 56.4 (5) |
C7A—C8A—C9A—C10A | 57.5 (5) | C14B—C8B—C9B—C11B | −50.3 (6) |
C14A—C8A—C9A—C10A | −176.3 (4) | C7B—C8B—C9B—C11B | −176.7 (4) |
C2A—C1A—C10A—C19A | −171.3 (5) | C11B—C9B—C10B—C1B | 58.9 (6) |
C2A—C1A—C10A—C9A | 66.5 (6) | C8B—C9B—C10B—C1B | −176.0 (4) |
C2A—C1A—C10A—C5A | −54.8 (6) | C11B—C9B—C10B—C19B | −60.4 (7) |
C11A—C9A—C10A—C1A | 56.0 (6) | C8B—C9B—C10B—C19B | 64.8 (6) |
C8A—C9A—C10A—C1A | −176.8 (4) | C11B—C9B—C10B—C5B | 178.8 (5) |
C11A—C9A—C10A—C19A | −63.3 (6) | C8B—C9B—C10B—C5B | −56.1 (5) |
C8A—C9A—C10A—C19A | 63.9 (5) | C2B—C1B—C10B—C9B | 65.1 (6) |
C11A—C9A—C10A—C5A | 176.1 (4) | C2B—C1B—C10B—C19B | −172.9 (5) |
C8A—C9A—C10A—C5A | −56.7 (5) | C2B—C1B—C10B—C5B | −56.6 (6) |
C6A—C5A—C10A—C1A | 177.0 (4) | C6B—C5B—C10B—C9B | 54.9 (6) |
C4A—C5A—C10A—C1A | 50.8 (5) | C4B—C5B—C10B—C9B | −70.7 (5) |
C6A—C5A—C10A—C19A | −68.1 (5) | C6B—C5B—C10B—C1B | 177.7 (5) |
C4A—C5A—C10A—C19A | 165.7 (4) | C4B—C5B—C10B—C1B | 52.2 (5) |
C6A—C5A—C10A—C9A | 53.9 (5) | C6B—C5B—C10B—C19B | −67.4 (6) |
C4A—C5A—C10A—C9A | −72.3 (5) | C4B—C5B—C10B—C19B | 167.0 (5) |
C8A—C9A—C11A—C12A | 51.8 (6) | C10B—C9B—C11B—C12B | 179.4 (4) |
C10A—C9A—C11A—C12A | 179.1 (4) | C8B—C9B—C11B—C12B | 53.4 (6) |
C9A—C11A—C12A—C13A | −57.9 (6) | C9B—C11B—C12B—C13B | −58.4 (6) |
C11A—C12A—C13A—C18A | −69.1 (5) | C11B—C12B—C13B—C18B | −69.1 (5) |
C11A—C12A—C13A—C14A | 54.5 (6) | C11B—C12B—C13B—C14B | 56.5 (5) |
C11A—C12A—C13A—C17A | 166.0 (4) | C11B—C12B—C13B—C17B | 168.4 (4) |
C7A—C8A—C14A—O5A | −69.5 (5) | C7B—C8B—C14B—O5B | −65.1 (5) |
C9A—C8A—C14A—O5A | 165.2 (4) | C9B—C8B—C14B—O5B | 169.5 (4) |
C7A—C8A—C14A—C15A | 53.9 (6) | C7B—C8B—C14B—C15B | 57.1 (6) |
C9A—C8A—C14A—C15A | −71.4 (5) | C9B—C8B—C14B—C15B | −68.3 (6) |
C7A—C8A—C14A—C13A | 172.9 (4) | C7B—C8B—C14B—C13B | 177.0 (4) |
C9A—C8A—C14A—C13A | 47.7 (5) | C9B—C8B—C14B—C13B | 51.6 (5) |
C18A—C13A—C14A—O5A | −46.7 (5) | C18B—C13B—C14B—O5B | −49.5 (5) |
C12A—C13A—C14A—O5A | −168.2 (4) | C12B—C13B—C14B—O5B | −172.4 (4) |
C17A—C13A—C14A—O5A | 78.1 (4) | C17B—C13B—C14B—O5B | 74.7 (4) |
C18A—C13A—C14A—C15A | −161.2 (4) | C18B—C13B—C14B—C8B | 69.7 (5) |
C12A—C13A—C14A—C15A | 77.2 (5) | C12B—C13B—C14B—C8B | −53.2 (5) |
C17A—C13A—C14A—C15A | −36.5 (5) | C17B—C13B—C14B—C8B | −166.1 (4) |
C18A—C13A—C14A—C8A | 72.5 (5) | C18B—C13B—C14B—C15B | −162.9 (4) |
C12A—C13A—C14A—C8A | −49.1 (5) | C12B—C13B—C14B—C15B | 74.2 (5) |
C17A—C13A—C14A—C8A | −162.8 (4) | C17B—C13B—C14B—C15B | −38.7 (5) |
O5A—C14A—C15A—C16A | −74.0 (5) | O5B—C14B—C15B—C16B | −72.9 (5) |
C8A—C14A—C15A—C16A | 162.9 (4) | C8B—C14B—C15B—C16B | 164.4 (4) |
C13A—C14A—C15A—C16A | 37.9 (5) | C13B—C14B—C15B—C16B | 39.4 (5) |
C14A—C15A—C16A—C17A | −24.4 (5) | C14B—C15B—C16B—C17B | −25.2 (5) |
C24A—O3A—C28A—C29A | 171.6 (4) | C15B—C16B—C17B—C20B | 126.8 (5) |
C24A—O3A—C28A—C27A | −66.5 (5) | C15B—C16B—C17B—C13B | 1.1 (5) |
O8A—C27A—C28A—O3A | −178.8 (4) | C18B—C13B—C17B—C20B | 21.7 (6) |
C26A—C27A—C28A—O3A | 58.8 (5) | C12B—C13B—C17B—C20B | 141.7 (4) |
O8A—C27A—C28A—C29A | −61.0 (6) | C14B—C13B—C17B—C20B | −103.0 (5) |
C26A—C27A—C28A—C29A | 176.7 (5) | C18B—C13B—C17B—C16B | 147.5 (5) |
C15A—C16A—C17A—C20A | 128.9 (5) | C12B—C13B—C17B—C16B | −92.4 (5) |
C15A—C16A—C17A—C13A | 1.1 (6) | C14B—C13B—C17B—C16B | 22.8 (5) |
C18A—C13A—C17A—C20A | 19.6 (6) | C16B—C17B—C20B—C22B | 132.0 (6) |
C12A—C13A—C17A—C20A | 141.3 (5) | C13B—C17B—C20B—C22B | −107.8 (7) |
C14A—C13A—C17A—C20A | −103.9 (5) | C16B—C17B—C20B—C21B | −47.0 (7) |
C18A—C13A—C17A—C16A | 145.4 (5) | C13B—C17B—C20B—C21B | 73.2 (7) |
C12A—C13A—C17A—C16A | −92.9 (5) | C23B—O1B—C21B—C20B | 0.4 (7) |
C14A—C13A—C17A—C16A | 21.9 (5) | C22B—C20B—C21B—O1B | −0.6 (7) |
C16A—C17A—C20A—C22A | 135.7 (6) | C17B—C20B—C21B—O1B | 178.6 (5) |
C13A—C17A—C20A—C22A | −101.7 (7) | C17B—C20B—C22B—C23B | −178.6 (6) |
C16A—C17A—C20A—C21A | −43.1 (7) | C21B—C20B—C22B—C23B | 0.6 (7) |
C13A—C17A—C20A—C21A | 79.4 (7) | C21B—O1B—C23B—O4B | 177.4 (8) |
C23A—O1A—C21A—C20A | 0.1 (7) | C21B—O1B—C23B—C22B | 0.0 (8) |
C22A—C20A—C21A—O1A | −0.3 (7) | C20B—C22B—C23B—O4B | −177.5 (8) |
C17A—C20A—C21A—O1A | 178.8 (5) | C20B—C22B—C23B—O1B | −0.4 (8) |
C21A—C20A—C22A—C23A | 0.3 (7) | C3B—O2B—C24B—O3B | −65.5 (5) |
C17A—C20A—C22A—C23A | −178.7 (5) | C3B—O2B—C24B—C25B | 173.2 (4) |
C21A—O1A—C23A—O4A | −178.7 (7) | C28B—O3B—C24B—O2B | −61.0 (5) |
C21A—O1A—C23A—C22A | 0.1 (8) | C28B—O3B—C24B—C25B | 60.5 (5) |
C20A—C22A—C23A—O4A | 178.4 (8) | O2B—C24B—C25B—O6B | −53.1 (5) |
C20A—C22A—C23A—O1A | −0.3 (8) | O3B—C24B—C25B—O6B | −176.0 (4) |
C3A—O2A—C24A—O3A | −64.6 (5) | O2B—C24B—C25B—C26B | 71.1 (5) |
C3A—O2A—C24A—C25A | 173.1 (4) | O3B—C24B—C25B—C26B | −51.8 (5) |
C28A—O3A—C24A—O2A | −60.4 (5) | C30B—O7B—C26B—C25B | 92.5 (6) |
C28A—O3A—C24A—C25A | 61.9 (5) | C30B—O7B—C26B—C27B | −146.8 (6) |
O2A—C24A—C25A—O6A | −52.4 (5) | O6B—C25B—C26B—O7B | −69.8 (5) |
O3A—C24A—C25A—O6A | −176.1 (4) | C24B—C25B—C26B—O7B | 167.2 (4) |
O2A—C24A—C25A—C26A | 72.2 (5) | O6B—C25B—C26B—C27B | 172.6 (4) |
O3A—C24A—C25A—C26A | −51.5 (5) | C24B—C25B—C26B—C27B | 49.6 (5) |
C30A—O7A—C26A—C25A | 90.6 (6) | O7B—C26B—C27B—O8B | 67.1 (5) |
C30A—O7A—C26A—C27A | −147.5 (6) | C25B—C26B—C27B—O8B | −172.5 (4) |
O6A—C25A—C26A—O7A | −70.2 (5) | O7B—C26B—C27B—C28B | −174.4 (4) |
C24A—C25A—C26A—O7A | 166.0 (4) | C25B—C26B—C27B—C28B | −54.0 (5) |
O6A—C25A—C26A—C27A | 172.0 (4) | C24B—O3B—C28B—C27B | −65.9 (5) |
C24A—C25A—C26A—C27A | 48.2 (5) | C24B—O3B—C28B—C29B | 172.2 (4) |
O8A—C27A—C26A—O7A | 66.5 (5) | O8B—C27B—C28B—O3B | 179.7 (4) |
C28A—C27A—C26A—O7A | −172.8 (4) | C26B—C27B—C28B—O3B | 59.8 (5) |
O8A—C27A—C26A—C25A | −172.3 (4) | O8B—C27B—C28B—C29B | −63.1 (6) |
C28A—C27A—C26A—C25A | −51.6 (5) | C26B—C27B—C28B—C29B | 176.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5A—H5AA···O1W | 0.82 | 2.11 | 2.770 (5) | 137 |
O6A—H6AA···O4Ai | 0.82 | 1.95 | 2.756 (8) | 170 |
O8A—H8AA···O7B | 0.82 | 2.15 | 2.941 (6) | 163 |
O5B—H5BB···O5Aii | 0.82 | 2.34 | 3.161 (4) | 174 |
O6B—H6BB···O4Biii | 0.82 | 1.84 | 2.659 (8) | 173 |
O8B—H8BB···O7A | 0.82 | 2.16 | 2.961 (6) | 167 |
O9—H9AA···O4A | 0.90 | 1.92 | 2.792 (9) | 165 |
O1W—H1W1···O9iv | 0.85 | 1.95 | 2.762 (7) | 159 |
O1W—H2W1···O6Bv | 0.85 | 2.16 | 2.926 (6) | 150 |
Symmetry codes: (i) x−1, y+1, z; (ii) x−2, y+1, z−1; (iii) x+1, y−1, z; (iv) x−1, y, z; (v) x+1, y−1, z+1. |
C32H48O9 | F(000) = 624 |
Mr = 576.70 | Dx = 1.237 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3351 (3) Å | Cell parameters from 8192 reflections |
b = 21.4770 (9) Å | θ = 1.9–29.5° |
c = 9.9056 (4) Å | µ = 0.09 mm−1 |
β = 97.007 (1)° | T = 293 K |
V = 1548.8 (1) Å3 | Slab, colourless |
Z = 2 | 0.50 × 0.48 × 0.26 mm |
Siemens SMART CCD area-detector diffractometer | 3461 independent reflections |
Radiation source: fine-focus sealed tube | 3057 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.104 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.0°, θmin = 1.9° |
ω scans | h = −9→9 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −27→16 |
Tmin = 0.957, Tmax = 0.977 | l = −12→12 |
10311 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-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 reflections | Δρmax = 0.46 e Å−3 |
376 parameters | Δρmin = −0.42 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.059 (4) |
C32H48O9 | V = 1548.8 (1) Å3 |
Mr = 576.70 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.3351 (3) Å | µ = 0.09 mm−1 |
b = 21.4770 (9) Å | T = 293 K |
c = 9.9056 (4) Å | 0.50 × 0.48 × 0.26 mm |
β = 97.007 (1)° |
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 = 0.977 | Rint = 0.104 |
10311 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 1 restraint |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.46 e Å−3 |
3461 reflections | Δρmin = −0.42 e Å−3 |
376 parameters |
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°. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.8702 (3) | 0.39833 (11) | 0.22303 (19) | 0.0355 (5) | |
O2 | 0.5568 (2) | 0.80573 (8) | 1.03926 (17) | 0.0202 (4) | |
O3 | 0.5051 (2) | 0.91233 (9) | 0.99367 (17) | 0.0228 (4) | |
O4 | 0.7986 (3) | 0.31586 (10) | 0.3445 (2) | 0.0405 (6) | |
O5 | 0.7325 (2) | 0.48921 (8) | 0.65740 (17) | 0.0214 (4) | |
H5A | 0.8357 | 0.4836 | 0.6975 | 0.032* | |
O6 | 0.4333 (2) | 0.81558 (9) | 1.28906 (19) | 0.0277 (4) | |
O7 | 0.6948 (3) | 0.90537 (10) | 1.40125 (18) | 0.0339 (5) | |
O8 | 0.9400 (3) | 0.94492 (10) | 1.2060 (2) | 0.0329 (5) | |
H8A | 0.9896 | 0.9106 | 1.2110 | 0.049* | |
O9 | 0.1323 (3) | 0.83055 (12) | 1.2285 (3) | 0.0486 (6) | |
C22 | 0.6948 (4) | 0.41973 (13) | 0.3943 (3) | 0.0267 (6) | |
H22 | 0.6248 | 0.4130 | 0.4651 | 0.032* | |
C23 | 0.7865 (4) | 0.37137 (14) | 0.3234 (3) | 0.0300 (6) | |
C21 | 0.8376 (4) | 0.46436 (15) | 0.2252 (3) | 0.0319 (6) | |
H21A | 0.7696 | 0.4780 | 0.1402 | 0.038* | |
H21B | 0.9527 | 0.4870 | 0.2395 | 0.038* | |
C20 | 0.7275 (3) | 0.47484 (13) | 0.3414 (3) | 0.0227 (5) | |
C17 | 0.6733 (3) | 0.53949 (12) | 0.3791 (2) | 0.0217 (5) | |
H17 | 0.6727 | 0.5660 | 0.2985 | 0.026* | |
C16 | 0.4791 (3) | 0.54199 (14) | 0.4258 (3) | 0.0254 (5) | |
H16A | 0.4033 | 0.5721 | 0.3719 | 0.030* | |
H16B | 0.4204 | 0.5015 | 0.4144 | 0.030* | |
C15 | 0.5022 (3) | 0.56093 (12) | 0.5763 (2) | 0.0202 (5) | |
H15A | 0.4626 | 0.6036 | 0.5864 | 0.024* | |
H15B | 0.4301 | 0.5340 | 0.6279 | 0.024* | |
C14 | 0.7076 (3) | 0.55413 (11) | 0.6260 (2) | 0.0166 (5) | |
C13 | 0.8026 (3) | 0.57067 (12) | 0.4989 (2) | 0.0194 (5) | |
C12 | 0.7944 (4) | 0.64185 (13) | 0.4787 (3) | 0.0253 (6) | |
H12A | 0.8610 | 0.6527 | 0.4033 | 0.030* | |
H12B | 0.6673 | 0.6542 | 0.4547 | 0.030* | |
C11 | 0.8746 (4) | 0.67828 (12) | 0.6041 (3) | 0.0259 (6) | |
H11A | 0.8655 | 0.7225 | 0.5848 | 0.031* | |
H11B | 1.0035 | 0.6680 | 0.6258 | 0.031* | |
C9 | 0.7726 (3) | 0.66331 (11) | 0.7270 (2) | 0.0182 (5) | |
H9 | 0.6436 | 0.6746 | 0.7010 | 0.022* | |
C8 | 0.7768 (3) | 0.59223 (11) | 0.7539 (2) | 0.0181 (5) | |
H8 | 0.9056 | 0.5807 | 0.7799 | 0.022* | |
C7 | 0.6725 (4) | 0.57457 (12) | 0.8727 (2) | 0.0240 (5) | |
H7A | 0.6910 | 0.5306 | 0.8926 | 0.029* | |
H7B | 0.5422 | 0.5812 | 0.8465 | 0.029* | |
C6 | 0.7349 (4) | 0.61250 (13) | 1.0011 (3) | 0.0264 (6) | |
H6A | 0.6576 | 0.6024 | 1.0708 | 0.032* | |
H6B | 0.8602 | 0.6013 | 1.0351 | 0.032* | |
C5 | 0.7247 (3) | 0.68265 (12) | 0.9729 (2) | 0.0208 (5) | |
H5 | 0.7786 | 0.7038 | 1.0559 | 0.025* | |
C10 | 0.8399 (3) | 0.70121 (12) | 0.8579 (3) | 0.0206 (5) | |
C1 | 0.8159 (3) | 0.77213 (12) | 0.8345 (3) | 0.0235 (5) | |
H1A | 0.8707 | 0.7939 | 0.9153 | 0.028* | |
H1B | 0.8821 | 0.7843 | 0.7598 | 0.028* | |
C2 | 0.6159 (3) | 0.79280 (12) | 0.8027 (2) | 0.0211 (5) | |
H2A | 0.6112 | 0.8378 | 0.7938 | 0.025* | |
H2B | 0.5640 | 0.7749 | 0.7165 | 0.025* | |
C3 | 0.5012 (3) | 0.77273 (12) | 0.9135 (2) | 0.0195 (5) | |
H3 | 0.3714 | 0.7814 | 0.8835 | 0.023* | |
C4 | 0.5246 (3) | 0.70378 (12) | 0.9444 (2) | 0.0205 (5) | |
H4A | 0.4650 | 0.6803 | 0.8678 | 0.025* | |
H4B | 0.4627 | 0.6940 | 1.0228 | 0.025* | |
C24 | 0.4517 (3) | 0.85795 (12) | 1.0619 (2) | 0.0199 (5) | |
H24 | 0.3219 | 0.8491 | 1.0325 | 0.024* | |
C28 | 0.6959 (3) | 0.92727 (13) | 1.0249 (3) | 0.0236 (5) | |
H28 | 0.7697 | 0.8931 | 0.9949 | 0.028* | |
C27 | 0.7467 (3) | 0.93729 (12) | 1.1779 (3) | 0.0231 (5) | |
H27 | 0.6891 | 0.9762 | 1.2023 | 0.028* | |
C26 | 0.6768 (4) | 0.88529 (12) | 1.2631 (2) | 0.0216 (5) | |
H26 | 0.7513 | 0.8479 | 1.2558 | 0.026* | |
C25 | 0.4783 (3) | 0.87072 (12) | 1.2142 (2) | 0.0213 (5) | |
H25 | 0.4003 | 0.9056 | 1.2351 | 0.026* | |
C18 | 1.0015 (3) | 0.54883 (14) | 0.5079 (3) | 0.0269 (6) | |
H18A | 1.0727 | 0.5687 | 0.5835 | 0.040* | |
H18B | 1.0506 | 0.5595 | 0.4254 | 0.040* | |
H18C | 1.0064 | 0.5045 | 0.5203 | 0.040* | |
C19 | 1.0452 (4) | 0.69052 (15) | 0.9029 (3) | 0.0336 (7) | |
H19A | 1.0811 | 0.7124 | 0.9865 | 0.050* | |
H19B | 1.1152 | 0.7057 | 0.8340 | 0.050* | |
H19C | 1.0678 | 0.6468 | 0.9165 | 0.050* | |
C30 | 0.7906 (6) | 0.8647 (2) | 1.4945 (3) | 0.0538 (10) | |
H30A | 0.7997 | 0.8826 | 1.5839 | 0.081* | |
H30B | 0.9116 | 0.8579 | 1.4698 | 0.081* | |
H30C | 0.7264 | 0.8258 | 1.4938 | 0.081* | |
C29 | 0.7272 (4) | 0.98522 (16) | 0.9435 (3) | 0.0374 (7) | |
H29A | 0.7037 | 0.9760 | 0.8481 | 0.056* | |
H29B | 0.8521 | 0.9988 | 0.9650 | 0.056* | |
H29C | 0.6457 | 1.0176 | 0.9657 | 0.056* | |
C31 | 0.2567 (4) | 0.80048 (15) | 1.2863 (3) | 0.0328 (6) | |
C32 | 0.2341 (6) | 0.74137 (19) | 1.3629 (4) | 0.0565 (10) | |
H32A | 0.1169 | 0.7232 | 1.3318 | 0.085* | |
H32B | 0.2408 | 0.7503 | 1.4583 | 0.085* | |
H32C | 0.3300 | 0.7128 | 1.3475 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0362 (11) | 0.0396 (13) | 0.0315 (10) | 0.0075 (9) | 0.0078 (8) | −0.0123 (9) |
O2 | 0.0186 (8) | 0.0179 (9) | 0.0233 (8) | 0.0039 (7) | −0.0005 (6) | −0.0053 (7) |
O3 | 0.0228 (8) | 0.0219 (9) | 0.0235 (8) | 0.0032 (7) | 0.0017 (7) | 0.0049 (7) |
O4 | 0.0414 (11) | 0.0276 (12) | 0.0487 (13) | 0.0049 (9) | −0.0092 (10) | −0.0118 (10) |
O5 | 0.0242 (9) | 0.0137 (9) | 0.0252 (8) | −0.0002 (7) | −0.0017 (7) | 0.0036 (7) |
O6 | 0.0287 (9) | 0.0261 (10) | 0.0302 (10) | 0.0018 (8) | 0.0112 (8) | 0.0052 (8) |
O7 | 0.0436 (12) | 0.0350 (12) | 0.0212 (9) | 0.0085 (9) | −0.0034 (8) | −0.0045 (8) |
O8 | 0.0273 (10) | 0.0278 (11) | 0.0422 (11) | −0.0079 (8) | −0.0011 (8) | −0.0097 (9) |
O9 | 0.0288 (11) | 0.0453 (15) | 0.0741 (17) | −0.0011 (11) | 0.0152 (11) | −0.0037 (13) |
C22 | 0.0280 (13) | 0.0270 (14) | 0.0251 (12) | −0.0016 (11) | 0.0040 (10) | −0.0070 (11) |
C23 | 0.0235 (13) | 0.0345 (17) | 0.0295 (14) | 0.0020 (11) | −0.0070 (11) | −0.0115 (12) |
C21 | 0.0320 (14) | 0.0365 (16) | 0.0292 (14) | 0.0027 (12) | 0.0118 (11) | −0.0062 (12) |
C20 | 0.0180 (11) | 0.0290 (15) | 0.0206 (11) | 0.0017 (10) | 0.0012 (9) | −0.0046 (10) |
C17 | 0.0246 (12) | 0.0235 (13) | 0.0173 (11) | 0.0033 (10) | 0.0034 (9) | 0.0015 (10) |
C16 | 0.0190 (11) | 0.0322 (15) | 0.0244 (12) | 0.0051 (10) | −0.0001 (9) | −0.0025 (11) |
C15 | 0.0162 (11) | 0.0238 (13) | 0.0213 (12) | 0.0017 (10) | 0.0055 (9) | 0.0020 (10) |
C14 | 0.0167 (10) | 0.0135 (11) | 0.0198 (11) | 0.0011 (9) | 0.0026 (9) | 0.0041 (9) |
C13 | 0.0183 (11) | 0.0191 (13) | 0.0220 (12) | 0.0007 (9) | 0.0070 (9) | 0.0021 (10) |
C12 | 0.0331 (13) | 0.0201 (13) | 0.0255 (13) | 0.0001 (10) | 0.0142 (11) | 0.0055 (10) |
C11 | 0.0335 (14) | 0.0157 (12) | 0.0318 (13) | −0.0056 (11) | 0.0173 (11) | 0.0006 (11) |
C9 | 0.0171 (10) | 0.0150 (11) | 0.0235 (11) | −0.0009 (9) | 0.0069 (9) | 0.0016 (9) |
C8 | 0.0176 (10) | 0.0158 (12) | 0.0208 (11) | −0.0007 (9) | 0.0025 (9) | 0.0016 (9) |
C7 | 0.0367 (14) | 0.0153 (13) | 0.0208 (12) | −0.0031 (10) | 0.0064 (10) | 0.0032 (10) |
C6 | 0.0365 (14) | 0.0240 (14) | 0.0178 (12) | 0.0022 (11) | −0.0001 (10) | 0.0035 (10) |
C5 | 0.0228 (12) | 0.0194 (13) | 0.0192 (11) | −0.0005 (9) | −0.0020 (9) | −0.0009 (9) |
C10 | 0.0164 (11) | 0.0174 (12) | 0.0279 (13) | −0.0025 (9) | 0.0017 (9) | −0.0011 (10) |
C1 | 0.0237 (12) | 0.0172 (13) | 0.0309 (13) | −0.0053 (10) | 0.0088 (10) | −0.0039 (10) |
C2 | 0.0270 (12) | 0.0147 (12) | 0.0222 (11) | 0.0002 (10) | 0.0049 (9) | −0.0011 (9) |
C3 | 0.0172 (11) | 0.0220 (13) | 0.0190 (11) | −0.0019 (9) | 0.0011 (9) | −0.0052 (10) |
C4 | 0.0205 (11) | 0.0205 (13) | 0.0209 (11) | −0.0039 (10) | 0.0043 (9) | −0.0013 (10) |
C24 | 0.0179 (11) | 0.0174 (12) | 0.0243 (12) | 0.0032 (9) | 0.0022 (9) | −0.0023 (10) |
C28 | 0.0215 (12) | 0.0235 (14) | 0.0259 (12) | 0.0005 (10) | 0.0036 (10) | −0.0033 (10) |
C27 | 0.0250 (12) | 0.0167 (12) | 0.0270 (13) | −0.0001 (10) | 0.0007 (10) | −0.0068 (10) |
C26 | 0.0257 (12) | 0.0182 (12) | 0.0206 (11) | 0.0045 (10) | 0.0020 (9) | −0.0036 (10) |
C25 | 0.0232 (12) | 0.0198 (13) | 0.0215 (12) | 0.0042 (10) | 0.0057 (9) | 0.0008 (10) |
C18 | 0.0194 (11) | 0.0281 (15) | 0.0347 (14) | −0.0009 (10) | 0.0090 (10) | −0.0053 (11) |
C19 | 0.0209 (13) | 0.0316 (16) | 0.0475 (17) | −0.0008 (11) | 0.0008 (12) | −0.0099 (13) |
C30 | 0.063 (2) | 0.066 (3) | 0.0296 (16) | 0.021 (2) | −0.0074 (16) | 0.0073 (17) |
C29 | 0.0442 (17) | 0.0342 (17) | 0.0359 (15) | −0.0070 (14) | 0.0131 (13) | 0.0053 (13) |
C31 | 0.0321 (14) | 0.0301 (15) | 0.0390 (15) | −0.0021 (13) | 0.0151 (12) | −0.0054 (13) |
C32 | 0.068 (2) | 0.047 (2) | 0.060 (2) | −0.0168 (19) | 0.0321 (19) | 0.0040 (19) |
O1—C23 | 1.360 (4) | C7—C6 | 1.533 (4) |
O1—C21 | 1.439 (4) | C7—H7A | 0.9700 |
O2—C24 | 1.394 (3) | C7—H7B | 0.9700 |
O2—C3 | 1.448 (3) | C6—C5 | 1.533 (4) |
O3—C24 | 1.428 (3) | C6—H6A | 0.9700 |
O3—C28 | 1.432 (3) | C6—H6B | 0.9700 |
O4—C23 | 1.212 (4) | C5—C4 | 1.529 (3) |
O5—C14 | 1.435 (3) | C5—C10 | 1.551 (4) |
O5—H5A | 0.8200 | C5—H5 | 0.9800 |
O6—C31 | 1.333 (3) | C10—C19 | 1.535 (3) |
O6—C25 | 1.456 (3) | C10—C1 | 1.548 (4) |
O7—C30 | 1.397 (4) | C1—C2 | 1.528 (4) |
O7—C26 | 1.426 (3) | C1—H1A | 0.9700 |
O8—C27 | 1.420 (3) | C1—H1B | 0.9700 |
O8—H8A | 0.8200 | C2—C3 | 1.524 (4) |
O9—C31 | 1.204 (4) | C2—H2A | 0.9700 |
C22—C20 | 1.328 (4) | C2—H2B | 0.9700 |
C22—C23 | 1.463 (4) | C3—C4 | 1.518 (4) |
C22—H22 | 0.9300 | C3—H3 | 0.9800 |
C21—C20 | 1.501 (4) | C4—H4A | 0.9700 |
C21—H21A | 0.9700 | C4—H4B | 0.9700 |
C21—H21B | 0.9700 | C24—C25 | 1.523 (3) |
C20—C17 | 1.504 (4) | C24—H24 | 0.9800 |
C17—C16 | 1.551 (4) | C28—C29 | 1.516 (4) |
C17—C13 | 1.576 (3) | C28—C27 | 1.531 (3) |
C17—H17 | 0.9800 | C28—H28 | 0.9800 |
C16—C15 | 1.535 (3) | C27—C26 | 1.526 (4) |
C16—H16A | 0.9700 | C27—H27 | 0.9800 |
C16—H16B | 0.9700 | C26—C25 | 1.510 (3) |
C15—C14 | 1.534 (3) | C26—H26 | 0.9800 |
C15—H15A | 0.9700 | C25—H25 | 0.9800 |
C15—H15B | 0.9700 | C18—H18A | 0.9600 |
C14—C8 | 1.541 (3) | C18—H18B | 0.9600 |
C14—C13 | 1.552 (3) | C18—H18C | 0.9600 |
C13—C18 | 1.525 (3) | C19—H19A | 0.9600 |
C13—C12 | 1.542 (4) | C19—H19B | 0.9600 |
C12—C11 | 1.524 (4) | C19—H19C | 0.9600 |
C12—H12A | 0.9700 | C30—H30A | 0.9600 |
C12—H12B | 0.9700 | C30—H30B | 0.9600 |
C11—C9 | 1.539 (3) | C30—H30C | 0.9600 |
C11—H11A | 0.9700 | C29—H29A | 0.9600 |
C11—H11B | 0.9700 | C29—H29B | 0.9600 |
C9—C8 | 1.549 (3) | C29—H29C | 0.9600 |
C9—C10 | 1.559 (3) | C31—C32 | 1.498 (5) |
C9—H9 | 0.9800 | C32—H32A | 0.9600 |
C8—C7 | 1.527 (3) | C32—H32B | 0.9600 |
C8—H8 | 0.9800 | C32—H32C | 0.9600 |
C23—O1—C21 | 108.5 (2) | C19—C10—C1 | 106.3 (2) |
C24—O2—C3 | 115.39 (18) | C19—C10—C5 | 110.6 (2) |
C24—O3—C28 | 113.47 (18) | C1—C10—C5 | 107.5 (2) |
C14—O5—H5A | 109.5 | C19—C10—C9 | 111.3 (2) |
C31—O6—C25 | 117.9 (2) | C1—C10—C9 | 111.8 (2) |
C30—O7—C26 | 115.2 (2) | C5—C10—C9 | 109.31 (18) |
C27—O8—H8A | 109.5 | C2—C1—C10 | 113.9 (2) |
C20—C22—C23 | 109.1 (3) | C2—C1—H1A | 108.8 |
C20—C22—H22 | 125.4 | C10—C1—H1A | 108.8 |
C23—C22—H22 | 125.4 | C2—C1—H1B | 108.8 |
O4—C23—O1 | 121.0 (3) | C10—C1—H1B | 108.8 |
O4—C23—C22 | 130.1 (3) | H1A—C1—H1B | 107.7 |
O1—C23—C22 | 108.9 (3) | C3—C2—C1 | 111.7 (2) |
O1—C21—C20 | 105.4 (2) | C3—C2—H2A | 109.3 |
O1—C21—H21A | 110.7 | C1—C2—H2A | 109.3 |
C20—C21—H21A | 110.7 | C3—C2—H2B | 109.3 |
O1—C21—H21B | 110.7 | C1—C2—H2B | 109.3 |
C20—C21—H21B | 110.7 | H2A—C2—H2B | 107.9 |
H21A—C21—H21B | 108.8 | O2—C3—C4 | 106.92 (19) |
C22—C20—C21 | 108.0 (2) | O2—C3—C2 | 111.05 (19) |
C22—C20—C17 | 131.2 (2) | C4—C3—C2 | 111.2 (2) |
C21—C20—C17 | 120.8 (2) | O2—C3—H3 | 109.2 |
C20—C17—C16 | 112.7 (2) | C4—C3—H3 | 109.2 |
C20—C17—C13 | 115.3 (2) | C2—C3—H3 | 109.2 |
C16—C17—C13 | 104.53 (19) | C3—C4—C5 | 114.2 (2) |
C20—C17—H17 | 108.0 | C3—C4—H4A | 108.7 |
C16—C17—H17 | 108.0 | C5—C4—H4A | 108.7 |
C13—C17—H17 | 108.0 | C3—C4—H4B | 108.7 |
C15—C16—C17 | 107.61 (19) | C5—C4—H4B | 108.7 |
C15—C16—H16A | 110.2 | H4A—C4—H4B | 107.6 |
C17—C16—H16A | 110.2 | O2—C24—O3 | 113.1 (2) |
C15—C16—H16B | 110.2 | O2—C24—C25 | 107.30 (19) |
C17—C16—H16B | 110.2 | O3—C24—C25 | 108.2 (2) |
H16A—C16—H16B | 108.5 | O2—C24—H24 | 109.4 |
C14—C15—C16 | 105.89 (18) | O3—C24—H24 | 109.4 |
C14—C15—H15A | 110.6 | C25—C24—H24 | 109.4 |
C16—C15—H15A | 110.6 | O3—C28—C29 | 106.1 (2) |
C14—C15—H15B | 110.6 | O3—C28—C27 | 111.0 (2) |
C16—C15—H15B | 110.6 | C29—C28—C27 | 112.1 (2) |
H15A—C15—H15B | 108.7 | O3—C28—H28 | 109.2 |
O5—C14—C15 | 104.81 (18) | C29—C28—H28 | 109.2 |
O5—C14—C8 | 108.49 (18) | C27—C28—H28 | 109.2 |
C15—C14—C8 | 115.16 (19) | O8—C27—C26 | 111.8 (2) |
O5—C14—C13 | 109.91 (19) | O8—C27—C28 | 109.1 (2) |
C15—C14—C13 | 103.82 (18) | C26—C27—C28 | 112.7 (2) |
C8—C14—C13 | 114.18 (19) | O8—C27—H27 | 107.7 |
C18—C13—C12 | 109.6 (2) | C26—C27—H27 | 107.7 |
C18—C13—C14 | 113.8 (2) | C28—C27—H27 | 107.7 |
C12—C13—C14 | 108.5 (2) | O7—C26—C25 | 110.1 (2) |
C18—C13—C17 | 113.4 (2) | O7—C26—C27 | 108.1 (2) |
C12—C13—C17 | 108.2 (2) | C25—C26—C27 | 110.5 (2) |
C14—C13—C17 | 103.00 (18) | O7—C26—H26 | 109.4 |
C11—C12—C13 | 113.5 (2) | C25—C26—H26 | 109.4 |
C11—C12—H12A | 108.9 | C27—C26—H26 | 109.4 |
C13—C12—H12A | 108.9 | O6—C25—C26 | 105.96 (19) |
C11—C12—H12B | 108.9 | O6—C25—C24 | 110.4 (2) |
C13—C12—H12B | 108.9 | C26—C25—C24 | 110.9 (2) |
H12A—C12—H12B | 107.7 | O6—C25—H25 | 109.8 |
C12—C11—C9 | 111.2 (2) | C26—C25—H25 | 109.8 |
C12—C11—H11A | 109.4 | C24—C25—H25 | 109.8 |
C9—C11—H11A | 109.4 | C13—C18—H18A | 109.5 |
C12—C11—H11B | 109.4 | C13—C18—H18B | 109.5 |
C9—C11—H11B | 109.4 | H18A—C18—H18B | 109.5 |
H11A—C11—H11B | 108.0 | C13—C18—H18C | 109.5 |
C11—C9—C8 | 109.9 (2) | H18A—C18—H18C | 109.5 |
C11—C9—C10 | 114.43 (19) | H18B—C18—H18C | 109.5 |
C8—C9—C10 | 111.97 (19) | C10—C19—H19A | 109.5 |
C11—C9—H9 | 106.7 | C10—C19—H19B | 109.5 |
C8—C9—H9 | 106.7 | H19A—C19—H19B | 109.5 |
C10—C9—H9 | 106.7 | C10—C19—H19C | 109.5 |
C7—C8—C14 | 110.84 (19) | H19A—C19—H19C | 109.5 |
C7—C8—C9 | 112.1 (2) | H19B—C19—H19C | 109.5 |
C14—C8—C9 | 112.60 (18) | O7—C30—H30A | 109.5 |
C7—C8—H8 | 107.0 | O7—C30—H30B | 109.5 |
C14—C8—H8 | 107.0 | H30A—C30—H30B | 109.5 |
C9—C8—H8 | 107.0 | O7—C30—H30C | 109.5 |
C8—C7—C6 | 112.4 (2) | H30A—C30—H30C | 109.5 |
C8—C7—H7A | 109.1 | H30B—C30—H30C | 109.5 |
C6—C7—H7A | 109.1 | C28—C29—H29A | 109.5 |
C8—C7—H7B | 109.1 | C28—C29—H29B | 109.5 |
C6—C7—H7B | 109.1 | H29A—C29—H29B | 109.5 |
H7A—C7—H7B | 107.9 | C28—C29—H29C | 109.5 |
C5—C6—C7 | 111.6 (2) | H29A—C29—H29C | 109.5 |
C5—C6—H6A | 109.3 | H29B—C29—H29C | 109.5 |
C7—C6—H6A | 109.3 | O9—C31—O6 | 123.9 (3) |
C5—C6—H6B | 109.3 | O9—C31—C32 | 124.8 (3) |
C7—C6—H6B | 109.3 | O6—C31—C32 | 111.3 (3) |
H6A—C6—H6B | 108.0 | C31—C32—H32A | 109.5 |
C4—C5—C6 | 110.5 (2) | C31—C32—H32B | 109.5 |
C4—C5—C10 | 112.63 (19) | H32A—C32—H32B | 109.5 |
C6—C5—C10 | 111.6 (2) | C31—C32—H32C | 109.5 |
C4—C5—H5 | 107.3 | H32A—C32—H32C | 109.5 |
C6—C5—H5 | 107.3 | H32B—C32—H32C | 109.5 |
C10—C5—H5 | 107.3 | ||
C21—O1—C23—O4 | −177.9 (2) | C7—C6—C5—C10 | −56.7 (3) |
C21—O1—C23—C22 | 0.3 (3) | C4—C5—C10—C19 | 169.0 (2) |
C20—C22—C23—O4 | 175.9 (3) | C6—C5—C10—C19 | −66.0 (3) |
C20—C22—C23—O1 | −2.1 (3) | C4—C5—C10—C1 | 53.4 (3) |
C23—O1—C21—C20 | 1.3 (3) | C6—C5—C10—C1 | 178.33 (19) |
C23—C22—C20—C21 | 2.9 (3) | C4—C5—C10—C9 | −68.1 (3) |
C23—C22—C20—C17 | −177.3 (2) | C6—C5—C10—C9 | 56.8 (2) |
O1—C21—C20—C22 | −2.7 (3) | C11—C9—C10—C19 | −58.5 (3) |
O1—C21—C20—C17 | 177.5 (2) | C8—C9—C10—C19 | 67.4 (3) |
C22—C20—C17—C16 | −36.5 (4) | C11—C9—C10—C1 | 60.2 (3) |
C21—C20—C17—C16 | 143.3 (2) | C8—C9—C10—C1 | −173.89 (19) |
C22—C20—C17—C13 | 83.4 (3) | C11—C9—C10—C5 | 179.1 (2) |
C21—C20—C17—C13 | −96.8 (3) | C8—C9—C10—C5 | −55.0 (3) |
C20—C17—C16—C15 | 114.8 (2) | C19—C10—C1—C2 | −174.1 (2) |
C13—C17—C16—C15 | −11.1 (3) | C5—C10—C1—C2 | −55.7 (3) |
C17—C16—C15—C14 | −13.3 (3) | C9—C10—C1—C2 | 64.2 (3) |
C16—C15—C14—O5 | −82.5 (2) | C10—C1—C2—C3 | 56.2 (3) |
C16—C15—C14—C8 | 158.3 (2) | C24—O2—C3—C4 | −141.8 (2) |
C16—C15—C14—C13 | 32.8 (3) | C24—O2—C3—C2 | 96.7 (2) |
O5—C14—C13—C18 | −50.8 (3) | C1—C2—C3—O2 | 67.6 (3) |
C15—C14—C13—C18 | −162.4 (2) | C1—C2—C3—C4 | −51.4 (3) |
C8—C14—C13—C18 | 71.4 (3) | O2—C3—C4—C5 | −70.2 (2) |
O5—C14—C13—C12 | −173.03 (18) | C2—C3—C4—C5 | 51.2 (3) |
C15—C14—C13—C12 | 75.3 (2) | C6—C5—C4—C3 | −179.3 (2) |
C8—C14—C13—C12 | −50.9 (3) | C10—C5—C4—C3 | −53.7 (3) |
O5—C14—C13—C17 | 72.4 (2) | C3—O2—C24—O3 | −82.4 (2) |
C15—C14—C13—C17 | −39.3 (2) | C3—O2—C24—C25 | 158.4 (2) |
C8—C14—C13—C17 | −165.46 (19) | C28—O3—C24—O2 | −54.8 (3) |
C20—C17—C13—C18 | 30.0 (3) | C28—O3—C24—C25 | 64.0 (2) |
C16—C17—C13—C18 | 154.3 (2) | C24—O3—C28—C29 | 179.5 (2) |
C20—C17—C13—C12 | 151.8 (2) | C24—O3—C28—C27 | −58.4 (3) |
C16—C17—C13—C12 | −83.9 (2) | O3—C28—C27—O8 | 173.4 (2) |
C20—C17—C13—C14 | −93.4 (2) | C29—C28—C27—O8 | −68.1 (3) |
C16—C17—C13—C14 | 30.9 (2) | O3—C28—C27—C26 | 48.6 (3) |
C18—C13—C12—C11 | −70.1 (3) | C29—C28—C27—C26 | 167.1 (2) |
C14—C13—C12—C11 | 54.7 (3) | C30—O7—C26—C25 | 112.4 (3) |
C17—C13—C12—C11 | 165.8 (2) | C30—O7—C26—C27 | −126.8 (3) |
C13—C12—C11—C9 | −59.2 (3) | O8—C27—C26—O7 | 69.3 (3) |
C12—C11—C9—C8 | 55.9 (3) | C28—C27—C26—O7 | −167.4 (2) |
C12—C11—C9—C10 | −177.1 (2) | O8—C27—C26—C25 | −170.1 (2) |
O5—C14—C8—C7 | −58.8 (2) | C28—C27—C26—C25 | −46.8 (3) |
C15—C14—C8—C7 | 58.2 (3) | C31—O6—C25—C26 | 166.2 (2) |
C13—C14—C8—C7 | 178.2 (2) | C31—O6—C25—C24 | −73.6 (3) |
O5—C14—C8—C9 | 174.77 (19) | O7—C26—C25—O6 | −68.1 (2) |
C15—C14—C8—C9 | −68.2 (2) | C27—C26—C25—O6 | 172.51 (19) |
C13—C14—C8—C9 | 51.8 (3) | O7—C26—C25—C24 | 172.1 (2) |
C11—C9—C8—C7 | −178.4 (2) | C27—C26—C25—C24 | 52.7 (3) |
C10—C9—C8—C7 | 53.3 (3) | O2—C24—C25—O6 | −55.1 (2) |
C11—C9—C8—C14 | −52.6 (2) | O3—C24—C25—O6 | −177.51 (17) |
C10—C9—C8—C14 | 179.07 (18) | O2—C24—C25—C26 | 62.0 (3) |
C14—C8—C7—C6 | −178.8 (2) | O3—C24—C25—C26 | −60.4 (3) |
C9—C8—C7—C6 | −52.1 (3) | C25—O6—C31—O9 | −1.9 (4) |
C8—C7—C6—C5 | 53.9 (3) | C25—O6—C31—C32 | 177.5 (2) |
C7—C6—C5—C4 | 69.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O8i | 0.82 | 1.98 | 2.777 (3) | 163 |
O8—H8A···O9ii | 0.82 | 2.01 | 2.828 (3) | 175 |
C3—H3···O4iii | 0.98 | 2.55 | 3.295 (3) | 132 |
C25—H25···O5iv | 0.98 | 2.36 | 3.311 (3) | 164 |
C32—H32B···O4iv | 0.96 | 2.45 | 3.345 (4) | 154 |
Symmetry codes: (i) −x+2, y−1/2, −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 formula | 2C30H46O8·CH4O·H2O | C32H48O9 |
Mr | 1119.39 | 576.70 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21 |
Temperature (K) | 213 | 293 |
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 |
V (Å3) | 1487.1 (1) | 1548.8 (1) |
Z | 1 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 |
Crystal size (mm) | 0.44 × 0.32 × 0.10 | 0.50 × 0.48 × 0.26 |
Data collection | ||
Diffractometer | Siemens SMART CCD area-detector diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.961, 0.991 | 0.957, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9863, 6292, 4368 | 10311, 3461, 3057 |
Rint | 0.072 | 0.104 |
(sin θ/λ)max (Å−1) | 0.639 | 0.639 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.182, 0.97 | 0.045, 0.106, 1.01 |
No. of reflections | 6292 | 3461 |
No. of parameters | 715 | 376 |
No. of restraints | 3 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.68, −0.70 | 0.46, −0.42 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
O2A—C24A | 1.405 (6) | O2B—C24B | 1.398 (6) |
O2A—C3A | 1.452 (6) | O2B—C3B | 1.446 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5A—H5AA···O1W | 0.82 | 2.11 | 2.770 (5) | 137 |
O6A—H6AA···O4Ai | 0.82 | 1.95 | 2.756 (8) | 170 |
O8A—H8AA···O7B | 0.82 | 2.15 | 2.941 (6) | 163 |
O5B—H5BB···O5Aii | 0.82 | 2.34 | 3.161 (4) | 174 |
O6B—H6BB···O4Biii | 0.82 | 1.84 | 2.659 (8) | 173 |
O8B—H8BB···O7A | 0.82 | 2.16 | 2.961 (6) | 167 |
O9—H9AA···O4A | 0.90 | 1.92 | 2.792 (9) | 165 |
O1W—H1W1···O9iv | 0.85 | 1.95 | 2.762 (7) | 159 |
O1W—H2W1···O6Bv | 0.85 | 2.16 | 2.926 (6) | 150 |
Symmetry codes: (i) x−1, y+1, z; (ii) x−2, y+1, z−1; (iii) x+1, y−1, z; (iv) x−1, y, z; (v) x+1, y−1, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O8i | 0.82 | 1.98 | 2.777 (3) | 163 |
O8—H8A···O9ii | 0.82 | 2.01 | 2.828 (3) | 175 |
C3—H3···O4iii | 0.98 | 2.55 | 3.295 (3) | 132 |
C25—H25···O5iv | 0.98 | 2.36 | 3.311 (3) | 164 |
C32—H32B···O4iv | 0.96 | 2.45 | 3.345 (4) | 154 |
Symmetry codes: (i) −x+2, y−1/2, −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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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 C═C and C═O 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.