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In order to study the in vivo protective effect on myocardial ischemia, (20S,24R)-ep­oxy­dammarane-12β,25-diol, (V), and (20S,24S)-ep­oxy­dammarane-12β,25-diol, (VI), were synthesized through a novel synthetic route. Two key inter­mediates, namely (20S,24R)-3-acetyl-20,24-ep­oxy­dammarane-3β,12β,25-triol, (III) [obtained as the hemihydrate, C32H54O5·0.5H2O, (IIIa), and the ethanol hemisolvate, C32H54O5·0.5C2H5OH, (IIIb), with identical conformations but different crystal packings], and (20S,24S)-3-acetyl-20,24-ep­oxy­dammarane-3β,12β,25-triol, C32H54O5, (IV), were obtained during the synthesis. The structures were confirmed by 1H NMR, 13C NMR and HRMS analyses, and single-crystal X-ray diffraction. Mol­ecules of (IIIa) are extended into a two-dimensional network constructed with water mol­ecules linked alternately through inter­molecular O—H...O hydrogen bonds, which are further stacked into a three-dimensional network. Compound (IIIb) contains two completely asymmetric mol­ecules, which are linked in a disordered manner through inter­molecular C—H...O hydrogen bonds. While the crystal stacks in compound (IV) are linked via weak C—H...O hydrogen bonds, the hydrogen-bonded chains extend helically along the crystallographic b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617006507/lf3050sup1.cif
Contains datablocks global, IIIa, IIIb, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006507/lf3050IIIasup2.hkl
Contains datablock IIIa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006507/lf3050IIIbsup4.hkl
Contains datablock IIIb

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617006507/lf3050IVsup3.hkl
Contains datablock IV

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229617006507/lf3050sup5.pdf
NMR spectra

CCDC references: 1502487; 1502485; 1502486

Computing details top

Data collection: FRAMBO (Bruker, 2004) for (IIIa), (IIIb); XSCANS (Bruker, 1997) for (IV). Cell refinement: FRAMBO (Bruker, 2004) for (IIIa), (IIIb); XSCANS (Bruker, 1997) for (IV). For all structures, data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

(20S,24R)-3-Acetyl-20,24-epoxydammarane-3β,12β,25-triol hemihydrate (IIIa) top
Crystal data top
C32H54O5·0.5H2OF(000) = 2328
Mr = 527.76Dx = 1.147 Mg m3
Monoclinic, C2Cu Kα radiation, λ = 1.54178 Å
a = 29.0091 (18) ÅCell parameters from 4093 reflections
b = 7.7205 (3) Åθ = 3.6–70.3°
c = 29.9984 (18) ŵ = 0.60 mm1
β = 114.524 (3)°T = 293 K
V = 6112.5 (6) Å3Block, colourless
Z = 80.47 × 0.40 × 0.38 mm
Data collection top
Bruker FRAMBO CCD area detector
diffractometer
8185 independent reflections
Radiation source: fine-focus sealed tube6202 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
phi and ω scansθmax = 66.4°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 3432
Tmin = 0.766, Tmax = 0.804k = 69
19762 measured reflectionsl = 3535
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.0959P)2 + 1.5622P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.185(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.36 e Å3
8185 reflectionsΔρmin = 0.40 e Å3
695 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00059 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), ???? Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.1 (3)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.96255 (11)0.4741 (5)0.87772 (11)0.0753 (8)
O2A0.69874 (12)0.4108 (5)0.58675 (11)0.0869 (10)
H2A0.67650.35840.56430.130*
O3A0.63663 (9)0.1821 (4)0.51817 (10)0.0635 (7)
O4A0.73073 (11)0.2374 (7)0.51518 (13)0.1082 (15)
H4A0.72370.24140.53900.162*
O5A0.93564 (17)0.7289 (6)0.89312 (17)0.1103 (13)
O1B0.85436 (12)0.9349 (5)0.97186 (13)0.0903 (11)
O2B0.54938 (14)0.7127 (5)0.73251 (13)0.1033 (13)
H2B0.53130.63980.71330.124*
O3B0.49477 (10)0.4447 (4)0.67772 (9)0.0615 (7)
O4B0.5175 (2)0.4484 (10)0.56510 (16)0.150 (2)
H4B0.48850.41480.54870.225*
O5B0.82853 (15)1.1280 (5)1.01257 (12)0.0904 (10)
O60.4259 (3)0.4871 (14)0.4858 (4)0.269 (5)
H6A0.40830.39680.48380.322*
H6B0.44340.47040.46940.322*
C1A0.85422 (15)0.4717 (6)0.75228 (15)0.0642 (10)
H1A10.85120.52770.72230.077*
H1A20.82740.51630.76050.077*
C2A0.90512 (16)0.5188 (6)0.79309 (15)0.0700 (11)
H2A10.93210.48400.78380.084*
H2A20.90710.64340.79770.084*
C3A0.91251 (15)0.4324 (6)0.84027 (15)0.0618 (10)
H3A0.88710.47810.85080.074*
C4A0.90774 (16)0.2350 (6)0.83745 (15)0.0621 (10)
C5A0.85707 (15)0.1891 (5)0.79341 (14)0.0579 (9)
H5A0.83090.23670.80250.069*
C6A0.84588 (18)0.0058 (6)0.78778 (15)0.0698 (11)
H6A10.86670.06070.77350.084*
H6A20.85430.05690.81980.084*
C7A0.79003 (18)0.0373 (6)0.75507 (15)0.0706 (11)
H7A10.76970.00960.77100.085*
H7A20.78400.16110.75150.085*
C8A0.77264 (16)0.0444 (5)0.70391 (14)0.0571 (9)
C9A0.78915 (14)0.2385 (5)0.70940 (13)0.0535 (8)
H9A0.77070.29150.72690.064*
C10A0.84664 (15)0.2760 (5)0.74322 (14)0.0562 (9)
C11A0.76883 (16)0.3328 (6)0.65971 (15)0.0642 (10)
H11A0.77800.45420.66520.077*
H11B0.78500.28480.63990.077*
C12A0.71152 (16)0.3185 (6)0.63133 (15)0.0648 (10)
H12A0.69510.37460.65030.078*
C13A0.69678 (14)0.1283 (5)0.62480 (14)0.0566 (9)
H13A0.71630.07350.60870.068*
C14A0.71328 (16)0.0402 (6)0.67585 (15)0.0629 (10)
C15A0.6869 (2)0.1360 (7)0.66050 (18)0.0803 (14)
H15A0.70490.20910.64660.096*
H15B0.68520.19510.68830.096*
C16A0.63393 (18)0.0920 (7)0.62208 (18)0.0828 (14)
H16A0.61110.06970.63760.099*
H16B0.62040.18660.59900.099*
C17A0.64062 (16)0.0739 (7)0.59557 (17)0.0702 (12)
H17A0.61890.16530.59900.084*
C18A0.79606 (17)0.0640 (6)0.67477 (16)0.0704 (11)
H18A0.83100.08820.69530.106*
H18B0.79390.00010.64650.106*
H18C0.77780.17100.66450.106*
C19A0.88221 (16)0.2175 (7)0.71910 (16)0.0722 (12)
H19A0.86470.22730.68410.108*
H19B0.89210.09920.72770.108*
H19C0.91180.28970.73050.108*
C20A0.62381 (16)0.0366 (6)0.54051 (17)0.0674 (11)
C21A0.56611 (17)0.0129 (8)0.5158 (2)0.0903 (16)
H21A0.55000.11030.52330.135*
H21B0.55700.09130.52770.135*
H21C0.55520.00490.48090.135*
C22A0.65044 (18)0.1164 (7)0.52922 (18)0.0755 (12)
H22A0.68240.14050.55680.091*
H22B0.62940.21920.52220.091*
C23A0.6591 (3)0.0643 (9)0.4858 (3)0.113 (2)
H23A0.63780.13170.45740.135*
H23B0.69430.08330.49170.135*
C24A0.64605 (16)0.1263 (7)0.47708 (16)0.0693 (11)
H24A0.61440.13690.44750.083*
C25A0.68540 (16)0.2463 (8)0.47138 (17)0.0812 (14)
C26A0.6663 (2)0.4298 (9)0.4607 (2)0.1052 (19)
H26A0.65980.47330.48750.158*
H26B0.63560.43230.43130.158*
H26C0.69140.50080.45650.158*
C27A0.6988 (2)0.1788 (11)0.4301 (2)0.111 (2)
H27A0.71730.26610.42160.166*
H27B0.66820.15150.40200.166*
H27C0.71920.07650.44100.166*
C28A0.9056 (2)0.1732 (7)0.88543 (15)0.0781 (13)
H28A0.93540.21110.91290.117*
H28B0.90380.04900.88550.117*
H28C0.87610.22090.88780.117*
C29A0.95502 (17)0.1508 (7)0.83454 (18)0.0823 (14)
H29A0.96030.20010.80760.123*
H29B0.94980.02820.82970.123*
H29C0.98430.17210.86450.123*
C30A0.68727 (18)0.1321 (8)0.70589 (17)0.0793 (14)
H30A0.65330.16360.68430.119*
H30B0.70600.23430.72110.119*
H30C0.68660.05470.73060.119*
C31A0.9686 (2)0.6238 (7)0.90139 (19)0.0803 (13)
C32A1.0224 (2)0.6432 (10)0.9391 (2)0.113 (2)
H32A1.02570.74910.95690.169*
H32B1.04490.64560.92300.169*
H32C1.03100.54700.96140.169*
C1B0.72790 (19)0.8628 (6)0.8661 (2)0.0860 (15)
H1B10.70580.89920.88130.103*
H1B20.71470.91100.83330.103*
C2B0.7809 (2)0.9353 (7)0.8955 (2)0.0934 (16)
H2B10.80270.90560.87930.112*
H2B20.77931.06060.89680.112*
C3B0.80307 (16)0.8639 (6)0.94664 (18)0.0749 (13)
H3B0.78240.90180.96370.090*
C4B0.80730 (15)0.6658 (6)0.94893 (15)0.0618 (10)
C5B0.75339 (15)0.5939 (5)0.91598 (13)0.0543 (9)
H5B0.73190.63300.93200.065*
C6B0.75042 (15)0.3965 (5)0.91642 (14)0.0570 (9)
H6B10.76640.34830.89650.068*
H6B20.76860.35440.94970.068*
C7B0.69562 (14)0.3374 (5)0.89669 (12)0.0541 (9)
H7B10.68080.37860.91840.065*
H7B20.69480.21180.89690.065*
C8B0.66320 (14)0.4021 (5)0.84438 (12)0.0485 (8)
C9B0.67050 (15)0.6025 (5)0.84302 (14)0.0564 (9)
H9B0.65810.64930.86640.068*
C10B0.72710 (15)0.6664 (5)0.86266 (14)0.0579 (9)
C11B0.63430 (17)0.6781 (6)0.79300 (15)0.0745 (13)
H11C0.63790.80310.79410.089*
H11D0.64420.63490.76790.089*
C12B0.57848 (17)0.6328 (6)0.77870 (16)0.0720 (12)
H12B0.56800.68060.80330.086*
C13B0.57364 (14)0.4368 (5)0.77826 (13)0.0564 (9)
H13B0.58930.39300.75720.068*
C14B0.60575 (15)0.3649 (6)0.83042 (13)0.0561 (9)
C15B0.58811 (16)0.1765 (6)0.82462 (15)0.0699 (11)
H15C0.60400.10990.80750.084*
H15D0.59620.12370.85630.084*
C16B0.53149 (18)0.1847 (7)0.79518 (16)0.0787 (13)
H16C0.51430.19680.81670.094*
H16D0.51940.08040.77580.094*
C17B0.52159 (16)0.3474 (6)0.76109 (14)0.0642 (11)
H17B0.49840.42520.76760.077*
C18B0.68009 (16)0.3033 (5)0.80896 (13)0.0556 (9)
H18D0.71620.28890.82390.083*
H18E0.67050.36780.77910.083*
H18F0.66410.19160.80190.083*
C19B0.75317 (18)0.6137 (7)0.82875 (15)0.0736 (12)
H19D0.72890.61760.79520.110*
H19E0.76640.49830.83670.110*
H19F0.78040.69260.83340.110*
C20B0.49652 (15)0.2927 (6)0.70699 (14)0.0593 (10)
C21B0.44211 (18)0.2332 (9)0.69276 (18)0.0894 (16)
H21D0.42410.31980.70220.134*
H21E0.44220.12630.70910.134*
H21F0.42570.21610.65800.134*
C22B0.52551 (17)0.1625 (6)0.69079 (14)0.0666 (10)
H22C0.56150.16910.71160.080*
H22D0.51390.04580.69230.080*
C23B0.5156 (3)0.2083 (9)0.6401 (2)0.110 (2)
H23C0.49180.12720.61740.132*
H23D0.54670.20550.63550.132*
C24B0.49352 (16)0.3891 (6)0.63154 (14)0.0656 (11)
H24B0.45800.38210.60780.079*
C25B0.5208 (2)0.5194 (9)0.61236 (18)0.0933 (17)
C26B0.5733 (2)0.5341 (11)0.6443 (2)0.123 (3)
H26D0.58580.42400.65940.185*
H26E0.57760.61850.66920.185*
H26F0.59190.56960.62590.185*
C27B0.4952 (3)0.6909 (10)0.6050 (2)0.132 (3)
H27D0.51560.76880.63050.198*
H27E0.46270.67710.60600.198*
H27F0.49060.73720.57380.198*
C28B0.82150 (18)0.6089 (8)1.00239 (15)0.0789 (13)
H28D0.85000.67521.02400.118*
H28E0.83010.48811.00580.118*
H28F0.79320.62811.01060.118*
C29B0.84958 (17)0.6027 (7)0.93416 (18)0.0754 (12)
H29D0.84270.64290.90170.113*
H29E0.85070.47840.93480.113*
H29F0.88160.64770.95680.113*
C30B0.58783 (17)0.4460 (8)0.86835 (15)0.0801 (14)
H30D0.55160.45810.85360.120*
H30E0.60320.55770.87830.120*
H30F0.59770.37180.89650.120*
C31B0.86103 (19)1.0718 (6)1.00185 (15)0.0703 (12)
C32B0.9141 (2)1.1389 (8)1.0201 (2)0.0969 (17)
H32D0.91741.21010.99540.145*
H32E0.93721.04331.02750.145*
H32F0.92161.20631.04920.145*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0637 (17)0.076 (2)0.0750 (18)0.0038 (15)0.0178 (14)0.0036 (17)
O2A0.092 (2)0.068 (2)0.0756 (19)0.0171 (18)0.0104 (16)0.0116 (16)
O3A0.0516 (14)0.0654 (18)0.0708 (16)0.0016 (13)0.0228 (12)0.0043 (14)
O4A0.0494 (16)0.175 (5)0.088 (2)0.007 (2)0.0163 (15)0.025 (3)
O5A0.109 (3)0.071 (2)0.143 (4)0.009 (2)0.045 (3)0.028 (2)
O1B0.076 (2)0.075 (2)0.110 (3)0.0165 (18)0.0284 (19)0.032 (2)
O2B0.108 (3)0.059 (2)0.088 (2)0.0012 (19)0.0138 (19)0.0097 (17)
O3B0.0643 (15)0.0540 (16)0.0560 (14)0.0051 (13)0.0147 (12)0.0002 (12)
O4B0.172 (5)0.186 (6)0.102 (3)0.015 (4)0.067 (3)0.004 (4)
O5B0.107 (3)0.077 (2)0.076 (2)0.007 (2)0.0264 (19)0.0188 (18)
O60.280 (11)0.203 (10)0.392 (13)0.013 (9)0.209 (10)0.050 (10)
C1A0.063 (2)0.051 (2)0.070 (2)0.0054 (19)0.0198 (19)0.0075 (19)
C2A0.065 (2)0.061 (3)0.076 (3)0.006 (2)0.022 (2)0.005 (2)
C3A0.057 (2)0.059 (2)0.068 (2)0.0044 (19)0.0238 (19)0.004 (2)
C4A0.066 (2)0.057 (2)0.062 (2)0.012 (2)0.0262 (18)0.0034 (19)
C5A0.069 (2)0.046 (2)0.063 (2)0.0083 (18)0.0306 (18)0.0030 (17)
C6A0.093 (3)0.051 (2)0.062 (2)0.005 (2)0.029 (2)0.0063 (19)
C7A0.095 (3)0.051 (2)0.071 (3)0.009 (2)0.039 (2)0.005 (2)
C8A0.073 (2)0.049 (2)0.057 (2)0.0007 (18)0.0350 (19)0.0012 (17)
C9A0.060 (2)0.048 (2)0.060 (2)0.0004 (17)0.0322 (17)0.0020 (17)
C10A0.062 (2)0.051 (2)0.061 (2)0.0013 (17)0.0307 (18)0.0027 (17)
C11A0.072 (3)0.050 (2)0.069 (2)0.007 (2)0.028 (2)0.005 (2)
C12A0.066 (2)0.061 (3)0.063 (2)0.003 (2)0.0231 (19)0.003 (2)
C13A0.052 (2)0.058 (2)0.067 (2)0.0056 (17)0.0325 (18)0.0062 (19)
C14A0.074 (3)0.062 (3)0.067 (2)0.011 (2)0.044 (2)0.004 (2)
C15A0.097 (3)0.075 (3)0.080 (3)0.025 (3)0.048 (3)0.001 (2)
C16A0.087 (3)0.089 (4)0.082 (3)0.032 (3)0.045 (3)0.009 (3)
C17A0.061 (2)0.076 (3)0.081 (3)0.008 (2)0.037 (2)0.009 (2)
C18A0.083 (3)0.061 (3)0.074 (3)0.003 (2)0.039 (2)0.011 (2)
C19A0.067 (2)0.088 (3)0.070 (2)0.001 (2)0.036 (2)0.000 (2)
C20A0.057 (2)0.069 (3)0.079 (3)0.010 (2)0.031 (2)0.008 (2)
C21A0.054 (2)0.110 (4)0.100 (4)0.025 (3)0.025 (2)0.020 (3)
C22A0.074 (3)0.068 (3)0.084 (3)0.006 (2)0.032 (2)0.011 (2)
C23A0.152 (6)0.085 (4)0.145 (5)0.023 (4)0.106 (5)0.016 (4)
C24A0.061 (2)0.080 (3)0.066 (2)0.006 (2)0.0258 (19)0.000 (2)
C25A0.050 (2)0.111 (4)0.073 (3)0.002 (3)0.016 (2)0.017 (3)
C26A0.099 (4)0.099 (5)0.116 (4)0.012 (4)0.043 (3)0.020 (4)
C27A0.097 (4)0.155 (7)0.096 (4)0.008 (4)0.056 (3)0.022 (4)
C28A0.103 (3)0.068 (3)0.061 (2)0.006 (3)0.032 (2)0.007 (2)
C29A0.070 (3)0.084 (4)0.085 (3)0.021 (3)0.024 (2)0.004 (3)
C30A0.076 (3)0.100 (4)0.080 (3)0.008 (3)0.051 (2)0.014 (3)
C31A0.087 (3)0.068 (3)0.084 (3)0.014 (3)0.034 (3)0.002 (3)
C32A0.096 (4)0.119 (5)0.095 (4)0.027 (4)0.012 (3)0.015 (4)
C1B0.084 (3)0.042 (2)0.099 (3)0.002 (2)0.004 (3)0.001 (2)
C2B0.089 (3)0.045 (2)0.116 (4)0.007 (2)0.012 (3)0.004 (3)
C3B0.062 (2)0.059 (3)0.094 (3)0.005 (2)0.022 (2)0.027 (2)
C4B0.064 (2)0.056 (2)0.064 (2)0.0012 (19)0.0246 (19)0.0121 (19)
C5B0.062 (2)0.047 (2)0.055 (2)0.0012 (17)0.0257 (17)0.0086 (16)
C6B0.065 (2)0.051 (2)0.052 (2)0.0087 (18)0.0220 (17)0.0054 (17)
C7B0.067 (2)0.049 (2)0.0447 (18)0.0001 (18)0.0216 (16)0.0043 (16)
C8B0.062 (2)0.0408 (19)0.0439 (17)0.0036 (16)0.0229 (16)0.0006 (14)
C9B0.069 (2)0.0371 (19)0.057 (2)0.0058 (17)0.0193 (18)0.0019 (16)
C10B0.071 (2)0.038 (2)0.061 (2)0.0002 (17)0.0235 (18)0.0026 (17)
C11B0.084 (3)0.040 (2)0.069 (3)0.003 (2)0.001 (2)0.0096 (19)
C12B0.075 (3)0.048 (2)0.066 (2)0.008 (2)0.003 (2)0.0021 (19)
C13B0.061 (2)0.051 (2)0.0498 (19)0.0049 (18)0.0162 (16)0.0033 (17)
C14B0.063 (2)0.061 (2)0.0454 (18)0.0011 (18)0.0229 (17)0.0006 (16)
C15B0.077 (3)0.072 (3)0.056 (2)0.015 (2)0.0229 (19)0.008 (2)
C16B0.081 (3)0.092 (4)0.064 (2)0.020 (3)0.030 (2)0.007 (2)
C17B0.064 (2)0.078 (3)0.055 (2)0.002 (2)0.0278 (19)0.003 (2)
C18B0.073 (2)0.0421 (19)0.0531 (19)0.0041 (17)0.0273 (17)0.0022 (16)
C19B0.092 (3)0.072 (3)0.063 (2)0.019 (2)0.039 (2)0.002 (2)
C20B0.061 (2)0.062 (3)0.052 (2)0.0036 (19)0.0203 (17)0.0002 (18)
C21B0.074 (3)0.113 (4)0.077 (3)0.024 (3)0.028 (2)0.001 (3)
C22B0.077 (3)0.054 (2)0.060 (2)0.002 (2)0.0189 (19)0.0013 (19)
C23B0.168 (6)0.092 (4)0.084 (3)0.036 (4)0.067 (4)0.010 (3)
C24B0.070 (2)0.068 (3)0.051 (2)0.010 (2)0.0166 (18)0.0017 (19)
C25B0.110 (4)0.102 (4)0.061 (3)0.017 (3)0.029 (3)0.010 (3)
C26B0.110 (4)0.165 (7)0.093 (4)0.057 (5)0.040 (3)0.018 (4)
C27B0.170 (7)0.098 (5)0.096 (4)0.015 (5)0.022 (4)0.023 (4)
C28B0.074 (3)0.089 (4)0.060 (2)0.003 (3)0.015 (2)0.015 (2)
C29B0.064 (2)0.078 (3)0.085 (3)0.003 (2)0.032 (2)0.018 (2)
C30B0.068 (3)0.119 (4)0.056 (2)0.003 (3)0.028 (2)0.015 (3)
C31B0.087 (3)0.052 (3)0.054 (2)0.012 (2)0.011 (2)0.0058 (19)
C32B0.096 (4)0.088 (4)0.086 (3)0.030 (3)0.017 (3)0.003 (3)
Geometric parameters (Å, º) top
O1A—C31A1.330 (7)C29A—H29A0.9600
O1A—C3A1.456 (5)C29A—H29B0.9600
O2A—C12A1.422 (5)C29A—H29C0.9600
O2A—H2A0.8200C30A—H30A0.9600
O3A—C20A1.433 (5)C30A—H30B0.9600
O3A—C24A1.435 (5)C30A—H30C0.9600
O4A—C25A1.423 (5)C31A—C32A1.509 (7)
O4A—H4A0.8200C32A—H32A0.9600
O5A—C31A1.198 (7)C32A—H32B0.9600
O1B—C31B1.349 (6)C32A—H32C0.9600
O1B—C3B1.467 (5)C1B—C10B1.519 (6)
O2B—C12B1.429 (5)C1B—C2B1.527 (7)
O2B—H2B0.8200C1B—H1B10.9700
O3B—C24B1.436 (5)C1B—H1B20.9700
O3B—C20B1.454 (5)C2B—C3B1.500 (7)
O4B—C25B1.485 (7)C2B—H2B10.9700
O4B—H4B0.8200C2B—H2B20.9700
O5B—C31B1.197 (6)C3B—C4B1.534 (6)
O6—H6A0.8499C3B—H3B0.9800
O6—H6B0.8500C4B—C28B1.544 (6)
C1A—C2A1.520 (6)C4B—C29B1.546 (6)
C1A—C10A1.535 (6)C4B—C5B1.564 (5)
C1A—H1A10.9700C5B—C6B1.527 (5)
C1A—H1A20.9700C5B—C10B1.562 (5)
C2A—C3A1.497 (6)C5B—H5B0.9800
C2A—H2A10.9700C6B—C7B1.518 (5)
C2A—H2A20.9700C6B—H6B10.9700
C3A—C4A1.530 (6)C6B—H6B20.9700
C3A—H3A0.9800C7B—C8B1.540 (5)
C4A—C28A1.542 (6)C7B—H7B10.9700
C4A—C29A1.553 (6)C7B—H7B20.9700
C4A—C5A1.556 (6)C8B—C18B1.544 (5)
C5A—C6A1.533 (6)C8B—C9B1.564 (5)
C5A—C10A1.559 (5)C8B—C14B1.567 (5)
C5A—H5A0.9800C9B—C11B1.545 (5)
C6A—C7A1.526 (6)C9B—C10B1.576 (5)
C6A—H6A10.9700C9B—H9B0.9800
C6A—H6A20.9700C10B—C19B1.553 (6)
C7A—C8A1.538 (5)C11B—C12B1.533 (6)
C7A—H7A10.9700C11B—H11C0.9700
C7A—H7A20.9700C11B—H11D0.9700
C8A—C18A1.556 (5)C12B—C13B1.519 (6)
C8A—C9A1.561 (6)C12B—H12B0.9800
C8A—C14A1.572 (6)C13B—C17B1.541 (6)
C9A—C11A1.539 (5)C13B—C14B1.554 (5)
C9A—C10A1.578 (5)C13B—H13B0.9800
C9A—H9A0.9800C14B—C15B1.528 (6)
C10A—C19A1.553 (5)C14B—C30B1.565 (5)
C11A—C12A1.525 (6)C15B—C16B1.509 (6)
C11A—H11A0.9700C15B—H15C0.9700
C11A—H11B0.9700C15B—H15D0.9700
C12A—C13A1.520 (6)C16B—C17B1.569 (7)
C12A—H12A0.9800C16B—H16C0.9700
C13A—C17A1.554 (6)C16B—H16D0.9700
C13A—C14A1.558 (6)C17B—C20B1.537 (5)
C13A—H13A0.9800C17B—H17B0.9800
C14A—C15A1.534 (6)C18B—H18D0.9600
C14A—C30A1.565 (6)C18B—H18E0.9600
C15A—C16A1.529 (7)C18B—H18F0.9600
C15A—H15A0.9700C19B—H19D0.9600
C15A—H15B0.9700C19B—H19E0.9600
C16A—C17A1.562 (7)C19B—H19F0.9600
C16A—H16A0.9700C20B—C22B1.515 (6)
C16A—H16B0.9700C20B—C21B1.525 (6)
C17A—C20A1.543 (6)C21B—H21D0.9600
C17A—H17A0.9800C21B—H21E0.9600
C18A—H18A0.9600C21B—H21F0.9600
C18A—H18B0.9600C22B—C23B1.468 (6)
C18A—H18C0.9600C22B—H22C0.9700
C19A—H19A0.9600C22B—H22D0.9700
C19A—H19B0.9600C23B—C24B1.513 (8)
C19A—H19C0.9600C23B—H23C0.9700
C20A—C22A1.525 (6)C23B—H23D0.9700
C20A—C21A1.535 (6)C24B—C25B1.532 (7)
C21A—H21A0.9600C24B—H24B0.9800
C21A—H21B0.9600C25B—C26B1.428 (8)
C21A—H21C0.9600C25B—C27B1.490 (10)
C22A—C23A1.483 (7)C26B—H26D0.9600
C22A—H22A0.9700C26B—H26E0.9600
C22A—H22B0.9700C26B—H26F0.9600
C23A—C24A1.515 (8)C27B—H27D0.9600
C23A—H23A0.9700C27B—H27E0.9600
C23A—H23B0.9700C27B—H27F0.9600
C24A—C25A1.534 (7)C28B—H28D0.9600
C24A—H24A0.9800C28B—H28E0.9600
C25A—C26A1.506 (9)C28B—H28F0.9600
C25A—C27A1.534 (7)C29B—H29D0.9600
C26A—H26A0.9600C29B—H29E0.9600
C26A—H26B0.9600C29B—H29F0.9600
C26A—H26C0.9600C30B—H30D0.9600
C27A—H27A0.9600C30B—H30E0.9600
C27A—H27B0.9600C30B—H30F0.9600
C27A—H27C0.9600C31B—C32B1.495 (7)
C28A—H28A0.9600C32B—H32D0.9600
C28A—H28B0.9600C32B—H32E0.9600
C28A—H28C0.9600C32B—H32F0.9600
C31A—O1A—C3A118.2 (4)C31A—C32A—H32B109.5
C12A—O2A—H2A109.5H32A—C32A—H32B109.5
C20A—O3A—C24A110.2 (3)C31A—C32A—H32C109.5
C25A—O4A—H4A109.5H32A—C32A—H32C109.5
C31B—O1B—C3B118.1 (4)H32B—C32A—H32C109.5
C12B—O2B—H2B109.5C10B—C1B—C2B112.8 (4)
C24B—O3B—C20B108.8 (3)C10B—C1B—H1B1109.0
C25B—O4B—H4B109.5C2B—C1B—H1B1109.0
C25B—O6—H6A107.5C10B—C1B—H1B2109.0
C25B—O6—H6B103.7C2B—C1B—H1B2109.0
H6A—O6—H6B108.5H1B1—C1B—H1B2107.8
C2A—C1A—C10A113.5 (4)C3B—C2B—C1B110.9 (5)
C2A—C1A—H1A1108.9C3B—C2B—H2B1109.5
C10A—C1A—H1A1108.9C1B—C2B—H2B1109.5
C2A—C1A—H1A2108.9C3B—C2B—H2B2109.5
C10A—C1A—H1A2108.9C1B—C2B—H2B2109.5
H1A1—C1A—H1A2107.7H2B1—C2B—H2B2108.0
C3A—C2A—C1A111.4 (4)O1B—C3B—C2B107.6 (4)
C3A—C2A—H2A1109.4O1B—C3B—C4B107.7 (4)
C1A—C2A—H2A1109.4C2B—C3B—C4B113.9 (4)
C3A—C2A—H2A2109.4O1B—C3B—H3B109.2
C1A—C2A—H2A2109.4C2B—C3B—H3B109.2
H2A1—C2A—H2A2108.0C4B—C3B—H3B109.2
O1A—C3A—C2A109.7 (3)C3B—C4B—C28B108.2 (4)
O1A—C3A—C4A107.5 (3)C3B—C4B—C29B111.1 (4)
C2A—C3A—C4A114.7 (4)C28B—C4B—C29B107.9 (4)
O1A—C3A—H3A108.3C3B—C4B—C5B106.6 (3)
C2A—C3A—H3A108.3C28B—C4B—C5B108.7 (3)
C4A—C3A—H3A108.3C29B—C4B—C5B114.3 (3)
C3A—C4A—C28A107.1 (4)C6B—C5B—C10B111.2 (3)
C3A—C4A—C29A111.0 (4)C6B—C5B—C4B113.2 (3)
C28A—C4A—C29A107.6 (4)C10B—C5B—C4B117.1 (3)
C3A—C4A—C5A107.8 (3)C6B—C5B—H5B104.7
C28A—C4A—C5A109.4 (4)C10B—C5B—H5B104.7
C29A—C4A—C5A113.7 (4)C4B—C5B—H5B104.7
C6A—C5A—C4A113.5 (3)C7B—C6B—C5B110.5 (3)
C6A—C5A—C10A111.6 (3)C7B—C6B—H6B1109.5
C4A—C5A—C10A117.3 (3)C5B—C6B—H6B1109.5
C6A—C5A—H5A104.2C7B—C6B—H6B2109.5
C4A—C5A—H5A104.2C5B—C6B—H6B2109.5
C10A—C5A—H5A104.2H6B1—C6B—H6B2108.1
C7A—C6A—C5A110.3 (4)C6B—C7B—C8B113.4 (3)
C7A—C6A—H6A1109.6C6B—C7B—H7B1108.9
C5A—C6A—H6A1109.6C8B—C7B—H7B1108.9
C7A—C6A—H6A2109.6C6B—C7B—H7B2108.9
C5A—C6A—H6A2109.6C8B—C7B—H7B2108.9
H6A1—C6A—H6A2108.1H7B1—C7B—H7B2107.7
C6A—C7A—C8A113.4 (3)C7B—C8B—C18B107.9 (3)
C6A—C7A—H7A1108.9C7B—C8B—C9B108.4 (3)
C8A—C7A—H7A1108.9C18B—C8B—C9B112.7 (3)
C6A—C7A—H7A2108.9C7B—C8B—C14B110.2 (3)
C8A—C7A—H7A2108.9C18B—C8B—C14B109.4 (3)
H7A1—C7A—H7A2107.7C9B—C8B—C14B108.4 (3)
C7A—C8A—C18A107.5 (4)C11B—C9B—C8B110.7 (3)
C7A—C8A—C9A109.2 (3)C11B—C9B—C10B115.3 (3)
C18A—C8A—C9A112.9 (3)C8B—C9B—C10B115.6 (3)
C7A—C8A—C14A111.0 (3)C11B—C9B—H9B104.6
C18A—C8A—C14A109.0 (3)C8B—C9B—H9B104.6
C9A—C8A—C14A107.2 (3)C10B—C9B—H9B104.6
C11A—C9A—C8A112.0 (3)C1B—C10B—C19B107.9 (4)
C11A—C9A—C10A114.4 (3)C1B—C10B—C5B107.5 (4)
C8A—C9A—C10A116.1 (3)C19B—C10B—C5B114.4 (3)
C11A—C9A—H9A104.2C1B—C10B—C9B108.8 (3)
C8A—C9A—H9A104.2C19B—C10B—C9B112.8 (3)
C10A—C9A—H9A104.2C5B—C10B—C9B105.1 (3)
C1A—C10A—C19A107.2 (4)C12B—C11B—C9B113.5 (4)
C1A—C10A—C5A107.3 (3)C12B—C11B—H11C108.9
C19A—C10A—C5A115.1 (3)C9B—C11B—H11C108.9
C1A—C10A—C9A109.3 (3)C12B—C11B—H11D108.9
C19A—C10A—C9A112.1 (3)C9B—C11B—H11D108.9
C5A—C10A—C9A105.8 (3)H11C—C11B—H11D107.7
C12A—C11A—C9A113.4 (3)O2B—C12B—C13B114.0 (3)
C12A—C11A—H11A108.9O2B—C12B—C11B107.7 (4)
C9A—C11A—H11A108.9C13B—C12B—C11B108.2 (4)
C12A—C11A—H11B108.9O2B—C12B—H12B109.0
C9A—C11A—H11B108.9C13B—C12B—H12B109.0
H11A—C11A—H11B107.7C11B—C12B—H12B109.0
O2A—C12A—C13A114.4 (4)C12B—C13B—C17B121.5 (4)
O2A—C12A—C11A106.7 (3)C12B—C13B—C14B109.4 (3)
C13A—C12A—C11A108.9 (4)C17B—C13B—C14B105.7 (3)
O2A—C12A—H12A108.9C12B—C13B—H13B106.4
C13A—C12A—H12A108.9C17B—C13B—H13B106.4
C11A—C12A—H12A108.9C14B—C13B—H13B106.4
C12A—C13A—C17A120.5 (4)C15B—C14B—C13B101.1 (3)
C12A—C13A—C14A109.9 (3)C15B—C14B—C30B105.5 (4)
C17A—C13A—C14A105.0 (3)C13B—C14B—C30B110.4 (3)
C12A—C13A—H13A106.9C15B—C14B—C8B118.3 (3)
C17A—C13A—H13A106.9C13B—C14B—C8B109.3 (3)
C14A—C13A—H13A106.9C30B—C14B—C8B111.7 (3)
C15A—C14A—C13A100.4 (3)C16B—C15B—C14B105.0 (4)
C15A—C14A—C30A106.0 (4)C16B—C15B—H15C110.8
C13A—C14A—C30A110.1 (4)C14B—C15B—H15C110.8
C15A—C14A—C8A118.5 (4)C16B—C15B—H15D110.8
C13A—C14A—C8A109.8 (3)C14B—C15B—H15D110.8
C30A—C14A—C8A111.4 (3)H15C—C15B—H15D108.8
C16A—C15A—C14A104.4 (4)C15B—C16B—C17B106.0 (4)
C16A—C15A—H15A110.9C15B—C16B—H16C110.5
C14A—C15A—H15A110.9C17B—C16B—H16C110.5
C16A—C15A—H15B110.9C15B—C16B—H16D110.5
C14A—C15A—H15B110.9C17B—C16B—H16D110.5
H15A—C15A—H15B108.9H16C—C16B—H16D108.7
C15A—C16A—C17A105.5 (4)C20B—C17B—C13B116.4 (3)
C15A—C16A—H16A110.6C20B—C17B—C16B110.3 (4)
C17A—C16A—H16A110.6C13B—C17B—C16B104.6 (3)
C15A—C16A—H16B110.6C20B—C17B—H17B108.4
C17A—C16A—H16B110.6C13B—C17B—H17B108.4
H16A—C16A—H16B108.8C16B—C17B—H17B108.4
C20A—C17A—C13A116.5 (3)C8B—C18B—H18D109.5
C20A—C17A—C16A110.0 (4)C8B—C18B—H18E109.5
C13A—C17A—C16A104.9 (4)H18D—C18B—H18E109.5
C20A—C17A—H17A108.4C8B—C18B—H18F109.5
C13A—C17A—H17A108.4H18D—C18B—H18F109.5
C16A—C17A—H17A108.4H18E—C18B—H18F109.5
C8A—C18A—H18A109.5C10B—C19B—H19D109.5
C8A—C18A—H18B109.5C10B—C19B—H19E109.5
H18A—C18A—H18B109.5H19D—C19B—H19E109.5
C8A—C18A—H18C109.5C10B—C19B—H19F109.5
H18A—C18A—H18C109.5H19D—C19B—H19F109.5
H18B—C18A—H18C109.5H19E—C19B—H19F109.5
C10A—C19A—H19A109.5O3B—C20B—C22B103.1 (3)
C10A—C19A—H19B109.5O3B—C20B—C21B107.6 (4)
H19A—C19A—H19B109.5C22B—C20B—C21B111.0 (4)
C10A—C19A—H19C109.5O3B—C20B—C17B107.4 (3)
H19A—C19A—H19C109.5C22B—C20B—C17B116.0 (3)
H19B—C19A—H19C109.5C21B—C20B—C17B111.1 (3)
O3A—C20A—C22A104.5 (3)C20B—C21B—H21D109.5
O3A—C20A—C21A108.1 (4)C20B—C21B—H21E109.5
C22A—C20A—C21A110.6 (4)H21D—C21B—H21E109.5
O3A—C20A—C17A109.0 (4)C20B—C21B—H21F109.5
C22A—C20A—C17A114.7 (4)H21D—C21B—H21F109.5
C21A—C20A—C17A109.6 (4)H21E—C21B—H21F109.5
C20A—C21A—H21A109.5C23B—C22B—C20B106.0 (4)
C20A—C21A—H21B109.5C23B—C22B—H22C110.5
H21A—C21A—H21B109.5C20B—C22B—H22C110.5
C20A—C21A—H21C109.5C23B—C22B—H22D110.5
H21A—C21A—H21C109.5C20B—C22B—H22D110.5
H21B—C21A—H21C109.5H22C—C22B—H22D108.7
C23A—C22A—C20A105.8 (4)C22B—C23B—C24B106.6 (4)
C23A—C22A—H22A110.6C22B—C23B—H23C110.4
C20A—C22A—H22A110.6C24B—C23B—H23C110.4
C23A—C22A—H22B110.6C22B—C23B—H23D110.4
C20A—C22A—H22B110.6C24B—C23B—H23D110.4
H22A—C22A—H22B108.7H23C—C23B—H23D108.6
C22A—C23A—C24A107.0 (5)O3B—C24B—C23B105.8 (4)
C22A—C23A—H23A110.3O3B—C24B—C25B110.9 (4)
C24A—C23A—H23A110.3C23B—C24B—C25B114.9 (5)
C22A—C23A—H23B110.3O3B—C24B—H24B108.4
C24A—C23A—H23B110.3C23B—C24B—H24B108.4
H23A—C23A—H23B108.6C25B—C24B—H24B108.4
O3A—C24A—C23A105.5 (4)C26B—C25B—O4B107.5 (5)
O3A—C24A—C25A109.3 (4)C26B—C25B—C27B110.9 (6)
C23A—C24A—C25A117.5 (4)O4B—C25B—C27B110.8 (5)
O3A—C24A—H24A108.1C26B—C25B—C24B111.9 (5)
C23A—C24A—H24A108.1O4B—C25B—C24B106.1 (5)
C25A—C24A—H24A108.1C27B—C25B—C24B109.5 (5)
O4A—C25A—C26A111.0 (5)C25B—C26B—H26D109.5
O4A—C25A—C27A106.4 (4)C25B—C26B—H26E109.5
C26A—C25A—C27A110.0 (5)H26D—C26B—H26E109.5
O4A—C25A—C24A108.2 (4)C25B—C26B—H26F109.5
C26A—C25A—C24A111.5 (4)H26D—C26B—H26F109.5
C27A—C25A—C24A109.5 (5)H26E—C26B—H26F109.5
C25A—C26A—H26A109.5C25B—C27B—H27D109.5
C25A—C26A—H26B109.5C25B—C27B—H27E109.5
H26A—C26A—H26B109.5H27D—C27B—H27E109.5
C25A—C26A—H26C109.5C25B—C27B—H27F109.5
H26A—C26A—H26C109.5H27D—C27B—H27F109.5
H26B—C26A—H26C109.5H27E—C27B—H27F109.5
C25A—C27A—H27A109.5C4B—C28B—H28D109.5
C25A—C27A—H27B109.5C4B—C28B—H28E109.5
H27A—C27A—H27B109.5H28D—C28B—H28E109.5
C25A—C27A—H27C109.5C4B—C28B—H28F109.5
H27A—C27A—H27C109.5H28D—C28B—H28F109.5
H27B—C27A—H27C109.5H28E—C28B—H28F109.5
C4A—C28A—H28A109.5C4B—C29B—H29D109.5
C4A—C28A—H28B109.5C4B—C29B—H29E109.5
H28A—C28A—H28B109.5H29D—C29B—H29E109.5
C4A—C28A—H28C109.5C4B—C29B—H29F109.5
H28A—C28A—H28C109.5H29D—C29B—H29F109.5
H28B—C28A—H28C109.5H29E—C29B—H29F109.5
C4A—C29A—H29A109.5C14B—C30B—H30D109.5
C4A—C29A—H29B109.5C14B—C30B—H30E109.5
H29A—C29A—H29B109.5H30D—C30B—H30E109.5
C4A—C29A—H29C109.5C14B—C30B—H30F109.5
H29A—C29A—H29C109.5H30D—C30B—H30F109.5
H29B—C29A—H29C109.5H30E—C30B—H30F109.5
C14A—C30A—H30A109.5O5B—C31B—O1B123.5 (4)
C14A—C30A—H30B109.5O5B—C31B—C32B125.6 (5)
H30A—C30A—H30B109.5O1B—C31B—C32B110.9 (5)
C14A—C30A—H30C109.5C31B—C32B—H32D109.5
H30A—C30A—H30C109.5C31B—C32B—H32E109.5
H30B—C30A—H30C109.5H32D—C32B—H32E109.5
O5A—C31A—O1A124.2 (5)C31B—C32B—H32F109.5
O5A—C31A—C32A125.3 (6)H32D—C32B—H32F109.5
O1A—C31A—C32A110.6 (5)H32E—C32B—H32F109.5
C31A—C32A—H32A109.5
C10A—C1A—C2A—C3A57.2 (5)C31B—O1B—C3B—C2B99.2 (5)
C31A—O1A—C3A—C2A82.7 (5)C31B—O1B—C3B—C4B137.7 (4)
C31A—O1A—C3A—C4A152.0 (4)C1B—C2B—C3B—O1B178.2 (4)
C1A—C2A—C3A—O1A177.3 (4)C1B—C2B—C3B—C4B58.9 (6)
C1A—C2A—C3A—C4A56.2 (5)O1B—C3B—C4B—C28B70.6 (5)
O1A—C3A—C4A—C28A69.0 (4)C2B—C3B—C4B—C28B170.2 (4)
C2A—C3A—C4A—C28A168.7 (3)O1B—C3B—C4B—C29B47.6 (5)
O1A—C3A—C4A—C29A48.2 (5)C2B—C3B—C4B—C29B71.6 (5)
C2A—C3A—C4A—C29A74.0 (4)O1B—C3B—C4B—C5B172.6 (3)
O1A—C3A—C4A—C5A173.4 (3)C2B—C3B—C4B—C5B53.4 (5)
C2A—C3A—C4A—C5A51.1 (5)C3B—C4B—C5B—C6B177.0 (4)
C3A—C4A—C5A—C6A177.0 (4)C28B—C4B—C5B—C6B60.6 (4)
C28A—C4A—C5A—C6A60.8 (5)C29B—C4B—C5B—C6B60.0 (5)
C29A—C4A—C5A—C6A59.5 (5)C3B—C4B—C5B—C10B51.7 (5)
C3A—C4A—C5A—C10A50.4 (4)C28B—C4B—C5B—C10B168.1 (4)
C28A—C4A—C5A—C10A166.6 (3)C29B—C4B—C5B—C10B71.4 (5)
C29A—C4A—C5A—C10A73.1 (5)C10B—C5B—C6B—C7B62.4 (4)
C4A—C5A—C6A—C7A162.7 (3)C4B—C5B—C6B—C7B163.5 (3)
C10A—C5A—C6A—C7A62.0 (4)C5B—C6B—C7B—C8B57.7 (4)
C5A—C6A—C7A—C8A57.4 (5)C6B—C7B—C8B—C18B70.9 (4)
C6A—C7A—C8A—C18A72.2 (5)C6B—C7B—C8B—C9B51.4 (4)
C6A—C7A—C8A—C9A50.7 (5)C6B—C7B—C8B—C14B169.8 (3)
C6A—C7A—C8A—C14A168.7 (4)C7B—C8B—C9B—C11B173.6 (3)
C7A—C8A—C9A—C11A174.9 (3)C18B—C8B—C9B—C11B67.1 (4)
C18A—C8A—C9A—C11A65.5 (4)C14B—C8B—C9B—C11B54.1 (4)
C14A—C8A—C9A—C11A54.6 (4)C7B—C8B—C9B—C10B52.9 (4)
C7A—C8A—C9A—C10A51.1 (4)C18B—C8B—C9B—C10B66.4 (4)
C18A—C8A—C9A—C10A68.5 (4)C14B—C8B—C9B—C10B172.4 (3)
C14A—C8A—C9A—C10A171.5 (3)C2B—C1B—C10B—C19B70.5 (6)
C2A—C1A—C10A—C19A71.1 (5)C2B—C1B—C10B—C5B53.4 (6)
C2A—C1A—C10A—C5A53.0 (5)C2B—C1B—C10B—C9B166.7 (4)
C2A—C1A—C10A—C9A167.2 (3)C6B—C5B—C10B—C1B175.3 (4)
C6A—C5A—C10A—C1A174.8 (3)C4B—C5B—C10B—C1B52.5 (5)
C4A—C5A—C10A—C1A51.7 (4)C6B—C5B—C10B—C19B64.9 (5)
C6A—C5A—C10A—C19A66.0 (5)C4B—C5B—C10B—C19B67.4 (5)
C4A—C5A—C10A—C19A67.4 (5)C6B—C5B—C10B—C9B59.5 (4)
C6A—C5A—C10A—C9A58.3 (4)C4B—C5B—C10B—C9B168.3 (3)
C4A—C5A—C10A—C9A168.2 (3)C11B—C9B—C10B—C1B57.2 (5)
C11A—C9A—C10A—C1A57.6 (4)C8B—C9B—C10B—C1B171.5 (4)
C8A—C9A—C10A—C1A169.6 (3)C11B—C9B—C10B—C19B62.6 (5)
C11A—C9A—C10A—C19A61.1 (5)C8B—C9B—C10B—C19B68.7 (4)
C8A—C9A—C10A—C19A71.8 (4)C11B—C9B—C10B—C5B172.1 (3)
C11A—C9A—C10A—C5A172.7 (3)C8B—C9B—C10B—C5B56.6 (4)
C8A—C9A—C10A—C5A54.4 (4)C8B—C9B—C11B—C12B54.5 (5)
C8A—C9A—C11A—C12A54.7 (5)C10B—C9B—C11B—C12B171.9 (3)
C10A—C9A—C11A—C12A170.5 (3)C9B—C11B—C12B—O2B179.0 (4)
C9A—C11A—C12A—O2A179.9 (4)C9B—C11B—C12B—C13B57.4 (5)
C9A—C11A—C12A—C13A55.9 (5)O2B—C12B—C13B—C17B55.1 (6)
O2A—C12A—C13A—C17A58.7 (5)C11B—C12B—C13B—C17B174.8 (3)
C11A—C12A—C13A—C17A178.0 (3)O2B—C12B—C13B—C14B178.7 (4)
O2A—C12A—C13A—C14A179.2 (3)C11B—C12B—C13B—C14B61.6 (5)
C11A—C12A—C13A—C14A59.9 (4)C12B—C13B—C14B—C15B169.7 (4)
C12A—C13A—C14A—C15A170.7 (4)C17B—C13B—C14B—C15B37.2 (4)
C17A—C13A—C14A—C15A39.7 (4)C12B—C13B—C14B—C30B58.4 (5)
C12A—C13A—C14A—C30A59.2 (4)C17B—C13B—C14B—C30B74.1 (4)
C17A—C13A—C14A—C30A71.7 (4)C12B—C13B—C14B—C8B64.8 (4)
C12A—C13A—C14A—C8A63.8 (4)C17B—C13B—C14B—C8B162.7 (3)
C17A—C13A—C14A—C8A165.3 (3)C7B—C8B—C14B—C15B67.1 (4)
C7A—C8A—C14A—C15A67.1 (5)C18B—C8B—C14B—C15B51.3 (4)
C18A—C8A—C14A—C15A51.1 (5)C9B—C8B—C14B—C15B174.5 (3)
C9A—C8A—C14A—C15A173.6 (3)C7B—C8B—C14B—C13B178.1 (3)
C7A—C8A—C14A—C13A178.5 (3)C18B—C8B—C14B—C13B63.5 (4)
C18A—C8A—C14A—C13A63.3 (4)C9B—C8B—C14B—C13B59.7 (4)
C9A—C8A—C14A—C13A59.2 (4)C7B—C8B—C14B—C30B55.7 (4)
C7A—C8A—C14A—C30A56.3 (5)C18B—C8B—C14B—C30B174.0 (4)
C18A—C8A—C14A—C30A174.5 (4)C9B—C8B—C14B—C30B62.7 (4)
C9A—C8A—C14A—C30A63.0 (4)C13B—C14B—C15B—C16B41.8 (4)
C13A—C14A—C15A—C16A44.0 (4)C30B—C14B—C15B—C16B73.2 (4)
C30A—C14A—C15A—C16A70.6 (4)C8B—C14B—C15B—C16B161.0 (3)
C8A—C14A—C15A—C16A163.4 (3)C14B—C15B—C16B—C17B30.9 (4)
C14A—C15A—C16A—C17A31.9 (5)C12B—C13B—C17B—C20B93.9 (5)
C12A—C13A—C17A—C20A92.9 (5)C14B—C13B—C17B—C20B140.8 (4)
C14A—C13A—C17A—C20A142.6 (4)C12B—C13B—C17B—C16B144.2 (4)
C12A—C13A—C17A—C16A145.3 (4)C14B—C13B—C17B—C16B18.8 (4)
C14A—C13A—C17A—C16A20.8 (4)C15B—C16B—C17B—C20B118.8 (4)
C15A—C16A—C17A—C20A119.5 (4)C15B—C16B—C17B—C13B7.1 (5)
C15A—C16A—C17A—C13A6.5 (5)C24B—O3B—C20B—C22B31.5 (4)
C24A—O3A—C20A—C22A27.8 (4)C24B—O3B—C20B—C21B85.8 (4)
C24A—O3A—C20A—C21A90.0 (4)C24B—O3B—C20B—C17B154.6 (3)
C24A—O3A—C20A—C17A150.8 (3)C13B—C17B—C20B—O3B53.5 (5)
C13A—C17A—C20A—O3A53.1 (5)C16B—C17B—C20B—O3B172.4 (3)
C16A—C17A—C20A—O3A172.2 (4)C13B—C17B—C20B—C22B61.2 (5)
C13A—C17A—C20A—C22A63.6 (5)C16B—C17B—C20B—C22B57.7 (5)
C16A—C17A—C20A—C22A55.5 (5)C13B—C17B—C20B—C21B170.8 (4)
C13A—C17A—C20A—C21A171.2 (4)C16B—C17B—C20B—C21B70.3 (5)
C16A—C17A—C20A—C21A69.7 (5)O3B—C20B—C22B—C23B28.2 (5)
O3A—C20A—C22A—C23A22.1 (5)C21B—C20B—C22B—C23B86.7 (5)
C21A—C20A—C22A—C23A93.9 (5)C17B—C20B—C22B—C23B145.3 (5)
C17A—C20A—C22A—C23A141.5 (5)C20B—C22B—C23B—C24B15.2 (6)
C20A—C22A—C23A—C24A9.3 (6)C20B—O3B—C24B—C23B22.5 (5)
C20A—O3A—C24A—C23A22.0 (5)C20B—O3B—C24B—C25B147.7 (4)
C20A—O3A—C24A—C25A149.2 (4)C22B—C23B—C24B—O3B3.8 (6)
C22A—C23A—C24A—O3A6.9 (6)C22B—C23B—C24B—C25B126.4 (5)
C22A—C23A—C24A—C25A128.9 (5)O3B—C24B—C25B—C26B62.7 (7)
O3A—C24A—C25A—O4A59.9 (5)C23B—C24B—C25B—C26B57.2 (7)
C23A—C24A—C25A—O4A60.2 (6)O3B—C24B—C25B—O4B179.6 (4)
O3A—C24A—C25A—C26A62.5 (5)C23B—C24B—C25B—O4B59.7 (6)
C23A—C24A—C25A—C26A177.4 (5)O3B—C24B—C25B—C27B60.7 (5)
O3A—C24A—C25A—C27A175.5 (4)C23B—C24B—C25B—C27B179.4 (5)
C23A—C24A—C25A—C27A55.4 (6)O3B—C24B—C25B—O6139.2 (3)
C3A—O1A—C31A—O5A1.8 (8)C23B—C24B—C25B—O6100.9 (4)
C3A—O1A—C31A—C32A179.2 (4)C3B—O1B—C31B—O5B7.3 (7)
C10B—C1B—C2B—C3B58.6 (6)C3B—O1B—C31B—C32B173.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···O3A0.821.942.742 (4)164
O2B—H2B···O3B0.821.902.707 (4)170
O4A—H4A···O2A0.822.272.986 (6)146
O4B—H4B···O60.822.082.750 (11)139
O6—H6A···O3Ai0.852.102.944 (11)176
C22Ai—H22i···O60.851.842.685 (9)176
Symmetry code: (i) x, y+1, z.
(20S,24R)-3-Acetyl-20,24-epoxydammarane-3β,12β,25-triol ethanol hemisolvate (IIIb) top
Crystal data top
C32H54O5·0.5C2H6OF(000) = 1196
Mr = 541.79Dx = 1.115 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 17.9895 (11) ÅCell parameters from 2108 reflections
b = 8.2912 (4) Åθ = 5.9–51.2°
c = 22.7981 (18) ŵ = 0.58 mm1
β = 108.343 (2)°T = 293 K
V = 3227.7 (4) Å3Bolck, colourless
Z = 40.48 × 0.40 × 0.26 mm
Data collection top
Bruker FRAMBO CCD area detector
diffractometer
7805 independent reflections
Radiation source: fine-focus sealed tube5421 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
phi and ω scansθmax = 66.0°, θmin = 3.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2120
Tmin = 0.768, Tmax = 0.864k = 79
11562 measured reflectionsl = 2627
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0694P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.153(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.30 e Å3
7805 reflectionsΔρmin = 0.18 e Å3
715 parametersExtinction correction: (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0030 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), ??? Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.0 (3)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.9301 (2)0.0001 (5)0.33120 (17)0.0941 (11)
O2A0.60401 (17)0.0850 (3)0.55463 (13)0.0660 (8)
H2A0.58260.13220.57660.099*
O3A0.57955 (16)0.2645 (3)0.64354 (12)0.0564 (7)
O4A0.69646 (18)0.0103 (4)0.67556 (15)0.0822 (10)
H4A0.67160.02860.63930.123*
O5A0.8463 (3)0.0379 (7)0.2379 (2)0.1280 (18)
O1B1.01126 (19)0.1275 (6)1.11617 (15)0.1051 (14)
O2B0.55129 (17)0.2790 (4)0.82613 (15)0.0732 (9)
H2B0.51270.33090.80660.110*
O3B0.42518 (16)0.4557 (3)0.77903 (12)0.0567 (7)
O4B0.40567 (18)0.1235 (4)0.82069 (14)0.0775 (9)
H4B0.45030.15430.82460.116*
O5B1.0809 (3)0.1057 (10)1.0529 (2)0.181 (3)
O60.8204 (6)0.7670 (10)0.7036 (4)0.241 (4)
H60.78260.82690.69830.289*
C1A0.7894 (3)0.0139 (6)0.4232 (2)0.0733 (13)
H1A10.77850.06740.45000.088*
H1A20.74100.03560.39040.088*
C2A0.8497 (3)0.0524 (6)0.3951 (2)0.0832 (14)
H2A10.89670.08260.42790.100*
H2A20.82890.14840.37120.100*
C3A0.8698 (3)0.0699 (6)0.3541 (2)0.0767 (14)
H3A0.82300.09070.31880.092*
C4A0.9002 (3)0.2307 (6)0.3853 (2)0.0677 (12)
C5A0.8400 (2)0.2892 (5)0.4170 (2)0.0593 (10)
H5A0.79150.30480.38270.071*
C6A0.8585 (3)0.4564 (6)0.4463 (2)0.0719 (13)
H6A10.87310.52790.41810.086*
H6A20.90260.44880.48390.086*
C7A0.7875 (3)0.5272 (5)0.4614 (2)0.0663 (12)
H7A10.80190.63130.48120.080*
H7A20.74540.54460.42320.080*
C8A0.7575 (2)0.4200 (5)0.50359 (19)0.0529 (9)
C9A0.7457 (2)0.2452 (5)0.47592 (19)0.0522 (10)
H9A0.70550.25760.43560.063*
C10A0.8168 (2)0.1696 (5)0.46074 (19)0.0579 (10)
C11A0.7075 (2)0.1343 (5)0.51256 (19)0.0590 (10)
H11A0.69660.03060.49190.071*
H11B0.74450.11650.55340.071*
C12A0.6319 (2)0.2011 (5)0.51947 (18)0.0543 (10)
H12A0.59310.21090.47830.065*
C13A0.6474 (2)0.3676 (5)0.54869 (18)0.0511 (9)
H13A0.69070.35640.58730.061*
C14A0.6760 (2)0.4812 (5)0.50630 (18)0.0543 (10)
C15A0.6731 (3)0.6443 (5)0.5373 (2)0.0664 (12)
H15A0.67400.73270.50960.080*
H15B0.71700.65570.57490.080*
C16A0.5952 (3)0.6401 (5)0.5516 (2)0.0681 (12)
H16A0.55290.68050.51680.082*
H16B0.59840.70550.58760.082*
C17A0.5811 (2)0.4584 (5)0.56424 (19)0.0571 (10)
H17A0.53060.42400.53560.068*
C18A0.8185 (2)0.4248 (6)0.5691 (2)0.0705 (12)
H18A0.87040.42470.56580.106*
H18B0.81190.33190.59210.106*
H18C0.81090.52090.59010.106*
C19A0.8842 (3)0.1251 (7)0.5199 (2)0.0799 (14)
H19A0.86280.09360.55180.120*
H19B0.91780.21670.53350.120*
H19C0.91380.03720.51110.120*
C20A0.5798 (2)0.4373 (5)0.63125 (19)0.0587 (10)
C21A0.5037 (3)0.5058 (6)0.6375 (2)0.0741 (13)
H21A0.45990.45890.60660.111*
H21B0.50300.62070.63220.111*
H21C0.50060.48080.67780.111*
C22A0.6527 (3)0.5026 (5)0.6814 (2)0.0708 (12)
H22A0.68660.56000.66280.085*
H22B0.63760.57530.70900.085*
C23A0.6941 (3)0.3547 (6)0.7163 (2)0.0720 (13)
H23A0.73390.31570.69930.086*
H23B0.71820.37810.75990.086*
C24A0.6284 (2)0.2341 (5)0.70643 (19)0.0591 (10)
H24A0.59850.26100.73430.071*
C25A0.6505 (3)0.0567 (6)0.7145 (2)0.0684 (12)
C26A0.7043 (3)0.0300 (7)0.7807 (2)0.0945 (17)
H26A0.72230.07960.78540.142*
H26B0.67590.05160.80910.142*
H26C0.74840.10150.78900.142*
C27A0.5783 (3)0.0476 (6)0.7008 (2)0.0827 (14)
H27A0.54710.03380.65840.124*
H27B0.54840.01670.72720.124*
H27C0.59360.15860.70810.124*
C28A0.9028 (3)0.3506 (7)0.3343 (2)0.0914 (17)
H28A0.93130.30360.30940.137*
H28B0.92830.44810.35290.137*
H28C0.85040.37470.30880.137*
C29A0.9846 (2)0.2126 (7)0.4305 (2)0.0891 (16)
H29A0.98640.12410.45810.134*
H29B0.99950.31010.45400.134*
H29C1.02010.19250.40750.134*
C30A0.6143 (2)0.4919 (6)0.44091 (19)0.0685 (12)
H30A0.56260.48930.44460.103*
H30B0.62080.40220.41640.103*
H30C0.62130.59080.42140.103*
C31A0.9103 (4)0.0519 (8)0.2728 (3)0.0951 (18)
C32A0.9783 (4)0.1233 (9)0.2582 (3)0.134 (3)
H32A0.99120.22560.27860.201*
H32B1.02240.05210.27220.201*
H32C0.96510.13820.21430.201*
C1B0.8170 (3)0.1674 (7)0.9912 (2)0.0805 (14)
H1B10.77930.08470.97140.097*
H1B20.83360.22030.95960.097*
C2B0.8879 (3)0.0879 (8)1.0379 (3)0.0962 (18)
H2B10.87090.02871.06810.115*
H2B20.91140.01191.01670.115*
C3B0.9473 (3)0.2112 (8)1.0701 (2)0.0894 (17)
H3B0.96820.26151.03970.107*
C4B0.9178 (3)0.3439 (8)1.1037 (2)0.0856 (16)
C5B0.8418 (3)0.4145 (7)1.0566 (2)0.0751 (14)
H5B0.85940.46451.02440.090*
C6B0.8061 (3)0.5541 (7)1.0834 (2)0.0906 (16)
H6B10.77870.51141.11040.109*
H6B20.84750.62451.10750.109*
C7B0.7490 (3)0.6505 (7)1.0309 (2)0.0860 (15)
H7B10.77770.69851.00580.103*
H7B20.72700.73751.04870.103*
C8B0.6811 (3)0.5470 (6)0.9888 (2)0.0658 (12)
C9B0.7172 (2)0.3922 (5)0.96911 (19)0.0600 (11)
H9B0.74850.43400.94430.072*
C10B0.7772 (3)0.2911 (7)1.0213 (2)0.0679 (12)
C11B0.6532 (3)0.2911 (6)0.92312 (19)0.0629 (11)
H11C0.67730.19800.91070.075*
H11D0.61690.25200.94360.075*
C12B0.6079 (2)0.3852 (5)0.86590 (19)0.0589 (10)
H12B0.64440.42000.84430.071*
C13B0.5717 (2)0.5336 (5)0.88482 (18)0.0552 (10)
H13B0.53860.49610.90900.066*
C14B0.6375 (3)0.6416 (5)0.9287 (2)0.0630 (11)
C15B0.5885 (3)0.7876 (6)0.9347 (2)0.0806 (14)
H15C0.62180.88000.95080.097*
H15D0.55790.76390.96180.097*
C16B0.5351 (3)0.8200 (5)0.8687 (2)0.0781 (14)
H16C0.55980.89460.84780.094*
H16D0.48570.86570.86920.094*
C17B0.5218 (2)0.6524 (5)0.8354 (2)0.0604 (11)
H17B0.54500.65750.80190.072*
C18B0.6244 (3)0.5045 (7)1.0259 (2)0.0844 (16)
H18D0.65400.46651.06620.127*
H18E0.58870.42191.00450.127*
H18F0.59540.59891.02980.127*
C19B0.7375 (3)0.2024 (7)1.0623 (2)0.0929 (17)
H19D0.68660.16611.03760.139*
H19E0.73220.27431.09380.139*
H19F0.76870.11131.08130.139*
C20B0.4349 (3)0.6167 (5)0.8065 (2)0.0608 (11)
C21B0.3981 (3)0.7351 (6)0.7544 (2)0.0833 (15)
H21D0.42360.72600.72330.125*
H21E0.40410.84300.77050.125*
H21F0.34340.71090.73650.125*
C22B0.3882 (3)0.6090 (6)0.8529 (2)0.0697 (12)
H22C0.42280.62450.89480.084*
H22D0.34830.69230.84380.084*
C23B0.3507 (3)0.4434 (6)0.8461 (2)0.0784 (14)
H23C0.29740.44960.84730.094*
H23D0.38050.37100.87840.094*
C24B0.3526 (2)0.3881 (5)0.7829 (2)0.0600 (11)
H24B0.30880.43850.75120.072*
C25B0.3512 (3)0.2079 (5)0.7704 (2)0.0631 (11)
C26B0.3681 (3)0.1761 (6)0.7103 (2)0.0796 (14)
H26D0.42130.20550.71480.119*
H26E0.33320.23900.67780.119*
H26F0.36060.06360.70010.119*
C27B0.2708 (3)0.1415 (7)0.7685 (3)0.0936 (16)
H27D0.26990.02680.76260.140*
H27E0.23090.19070.73490.140*
H27F0.26150.16560.80670.140*
C28B0.9814 (3)0.4759 (10)1.1194 (3)0.117 (2)
H28D1.03080.42931.14250.175*
H28E0.96760.55861.14360.175*
H28F0.98550.52191.08190.175*
C29B0.9065 (3)0.2828 (10)1.1638 (2)0.109 (2)
H29D0.87420.18801.15540.164*
H29E0.88160.36511.18070.164*
H29F0.95650.25711.19300.164*
C30B0.6943 (3)0.7039 (6)0.8946 (2)0.0782 (14)
H30D0.66590.71900.85160.117*
H30E0.73530.62640.89870.117*
H30F0.71660.80470.91230.117*
C31B1.0714 (4)0.0792 (11)1.1008 (3)0.124 (3)
C32B1.1291 (4)0.0131 (13)1.1526 (3)0.158 (4)
H32D1.18000.00901.14740.237*
H32E1.11250.12341.15170.237*
H32F1.13140.03441.19150.237*
C330.8766 (5)0.843 (2)0.6824 (6)0.215 (6)
H33A0.86420.82430.63830.258*
H33B0.92760.79610.70280.258*
C340.8799 (7)1.0225 (16)0.6945 (5)0.220 (6)
H34A0.83431.07310.66680.330*
H34B0.92601.06670.68800.330*
H34C0.88151.04180.73640.330*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.085 (2)0.109 (3)0.095 (3)0.023 (2)0.038 (2)0.009 (2)
O2A0.088 (2)0.0454 (15)0.0740 (18)0.0128 (15)0.0388 (16)0.0035 (15)
O3A0.0676 (17)0.0480 (15)0.0527 (15)0.0030 (14)0.0177 (14)0.0011 (13)
O4A0.084 (2)0.089 (2)0.082 (2)0.031 (2)0.0379 (18)0.0143 (19)
O5A0.122 (3)0.162 (5)0.114 (3)0.040 (4)0.058 (3)0.048 (4)
O1B0.074 (2)0.165 (4)0.075 (2)0.035 (3)0.0224 (18)0.020 (3)
O2B0.0685 (18)0.0580 (17)0.085 (2)0.0118 (16)0.0128 (16)0.0168 (17)
O3B0.0667 (17)0.0457 (14)0.0618 (16)0.0088 (14)0.0261 (14)0.0008 (14)
O4B0.091 (2)0.0582 (18)0.076 (2)0.0058 (18)0.0148 (17)0.0138 (17)
O5B0.131 (4)0.321 (10)0.105 (3)0.088 (5)0.056 (3)0.027 (5)
O60.304 (10)0.142 (6)0.291 (10)0.045 (7)0.115 (8)0.030 (7)
C1A0.087 (3)0.058 (3)0.085 (3)0.000 (3)0.041 (3)0.008 (3)
C2A0.097 (4)0.067 (3)0.096 (4)0.003 (3)0.045 (3)0.011 (3)
C3A0.071 (3)0.083 (3)0.085 (3)0.011 (3)0.037 (3)0.005 (3)
C4A0.060 (3)0.070 (3)0.077 (3)0.005 (2)0.027 (2)0.007 (3)
C5A0.056 (2)0.058 (2)0.067 (3)0.003 (2)0.022 (2)0.007 (2)
C6A0.074 (3)0.060 (3)0.089 (3)0.008 (3)0.035 (3)0.005 (3)
C7A0.076 (3)0.045 (2)0.083 (3)0.007 (2)0.033 (3)0.007 (2)
C8A0.058 (2)0.041 (2)0.059 (2)0.0052 (19)0.0172 (19)0.0011 (19)
C9A0.061 (2)0.040 (2)0.058 (2)0.0006 (19)0.022 (2)0.0042 (19)
C10A0.066 (2)0.048 (2)0.060 (2)0.006 (2)0.021 (2)0.006 (2)
C11A0.079 (3)0.038 (2)0.065 (2)0.001 (2)0.030 (2)0.001 (2)
C12A0.068 (2)0.044 (2)0.054 (2)0.009 (2)0.023 (2)0.0002 (19)
C13A0.058 (2)0.041 (2)0.054 (2)0.0004 (19)0.0169 (18)0.0027 (18)
C14A0.062 (2)0.043 (2)0.058 (2)0.002 (2)0.0183 (19)0.006 (2)
C15A0.080 (3)0.040 (2)0.083 (3)0.001 (2)0.032 (2)0.008 (2)
C16A0.084 (3)0.049 (2)0.076 (3)0.009 (2)0.032 (2)0.012 (2)
C17A0.060 (2)0.048 (2)0.061 (2)0.000 (2)0.016 (2)0.005 (2)
C18A0.061 (3)0.069 (3)0.076 (3)0.004 (2)0.014 (2)0.013 (3)
C19A0.086 (3)0.087 (4)0.068 (3)0.032 (3)0.025 (3)0.020 (3)
C20A0.068 (3)0.044 (2)0.066 (3)0.003 (2)0.023 (2)0.000 (2)
C21A0.086 (3)0.066 (3)0.082 (3)0.012 (3)0.043 (3)0.003 (3)
C22A0.085 (3)0.052 (3)0.073 (3)0.006 (2)0.022 (3)0.011 (2)
C23A0.073 (3)0.073 (3)0.063 (3)0.007 (3)0.011 (2)0.000 (2)
C24A0.065 (3)0.060 (3)0.053 (2)0.003 (2)0.020 (2)0.003 (2)
C25A0.083 (3)0.061 (3)0.070 (3)0.010 (3)0.035 (3)0.011 (2)
C26A0.109 (4)0.095 (4)0.075 (3)0.026 (4)0.022 (3)0.032 (3)
C27A0.104 (4)0.053 (3)0.097 (4)0.003 (3)0.039 (3)0.010 (3)
C28A0.088 (3)0.104 (4)0.092 (4)0.018 (3)0.042 (3)0.021 (3)
C29A0.062 (3)0.108 (4)0.093 (4)0.012 (3)0.018 (3)0.004 (3)
C30A0.065 (3)0.074 (3)0.066 (3)0.011 (3)0.020 (2)0.019 (3)
C31A0.107 (4)0.092 (4)0.102 (5)0.017 (4)0.055 (4)0.019 (4)
C32A0.164 (6)0.120 (6)0.152 (6)0.015 (5)0.100 (5)0.024 (5)
C1B0.074 (3)0.089 (4)0.076 (3)0.021 (3)0.022 (2)0.003 (3)
C2B0.076 (3)0.119 (5)0.089 (4)0.029 (4)0.019 (3)0.006 (4)
C3B0.071 (3)0.130 (5)0.066 (3)0.016 (4)0.019 (3)0.016 (3)
C4B0.074 (3)0.122 (5)0.058 (3)0.008 (3)0.016 (2)0.007 (3)
C5B0.077 (3)0.096 (4)0.054 (2)0.008 (3)0.022 (2)0.004 (3)
C6B0.095 (4)0.106 (4)0.061 (3)0.009 (4)0.012 (3)0.012 (3)
C7B0.094 (3)0.080 (3)0.073 (3)0.004 (3)0.011 (3)0.016 (3)
C8B0.078 (3)0.063 (3)0.061 (3)0.006 (2)0.029 (2)0.004 (2)
C9B0.070 (3)0.061 (3)0.057 (2)0.002 (2)0.031 (2)0.002 (2)
C10B0.071 (3)0.082 (3)0.057 (3)0.009 (3)0.029 (2)0.009 (3)
C11B0.071 (3)0.055 (2)0.067 (3)0.006 (2)0.028 (2)0.002 (2)
C12B0.067 (3)0.052 (2)0.059 (2)0.004 (2)0.023 (2)0.003 (2)
C13B0.066 (2)0.047 (2)0.058 (2)0.002 (2)0.028 (2)0.002 (2)
C14B0.074 (3)0.046 (2)0.067 (3)0.001 (2)0.021 (2)0.001 (2)
C15B0.091 (3)0.053 (3)0.089 (4)0.008 (3)0.015 (3)0.011 (3)
C16B0.091 (3)0.045 (2)0.095 (4)0.003 (2)0.025 (3)0.003 (3)
C17B0.072 (3)0.045 (2)0.069 (3)0.001 (2)0.029 (2)0.004 (2)
C18B0.094 (3)0.105 (4)0.067 (3)0.025 (3)0.043 (3)0.008 (3)
C19B0.085 (3)0.110 (4)0.092 (4)0.007 (3)0.041 (3)0.037 (4)
C20B0.072 (3)0.046 (2)0.068 (3)0.009 (2)0.027 (2)0.000 (2)
C21B0.091 (3)0.054 (3)0.094 (4)0.008 (3)0.013 (3)0.011 (3)
C22B0.072 (3)0.059 (3)0.081 (3)0.012 (2)0.028 (2)0.015 (3)
C23B0.090 (3)0.077 (3)0.084 (3)0.001 (3)0.049 (3)0.008 (3)
C24B0.058 (2)0.054 (2)0.067 (3)0.006 (2)0.020 (2)0.001 (2)
C25B0.065 (3)0.049 (2)0.072 (3)0.004 (2)0.016 (2)0.005 (2)
C26B0.100 (3)0.063 (3)0.070 (3)0.010 (3)0.020 (3)0.008 (3)
C27B0.086 (3)0.071 (3)0.121 (4)0.009 (3)0.028 (3)0.005 (3)
C28B0.086 (4)0.159 (7)0.090 (4)0.007 (5)0.006 (3)0.007 (5)
C29B0.103 (4)0.163 (6)0.059 (3)0.030 (5)0.023 (3)0.021 (4)
C30B0.080 (3)0.065 (3)0.084 (3)0.014 (3)0.017 (3)0.010 (3)
C31B0.088 (4)0.203 (9)0.080 (4)0.038 (5)0.024 (3)0.003 (5)
C32B0.103 (4)0.254 (11)0.110 (5)0.078 (6)0.023 (4)0.028 (6)
C330.092 (6)0.279 (18)0.293 (15)0.004 (8)0.087 (7)0.058 (14)
C340.251 (12)0.241 (14)0.180 (9)0.161 (11)0.085 (9)0.022 (9)
Geometric parameters (Å, º) top
O1A—C31A1.337 (7)C30A—H30A0.9600
O1A—C3A1.464 (5)C30A—H30B0.9600
O2A—C12A1.440 (4)C30A—H30C0.9600
O2A—H2A0.8200C31A—C32A1.488 (8)
O3A—C24A1.449 (5)C32A—H32A0.9600
O3A—C20A1.460 (5)C32A—H32B0.9600
O4A—C25A1.443 (5)C32A—H32C0.9600
O4A—H4A0.8200C1B—C2B1.529 (6)
O5A—C31A1.182 (7)C1B—C10B1.530 (6)
O1B—C31B1.302 (6)C1B—H1B10.9700
O1B—C3B1.465 (6)C1B—H1B20.9700
O2B—C12B1.433 (5)C2B—C3B1.494 (8)
O2B—H2B0.8200C2B—H2B10.9700
O3B—C24B1.450 (5)C2B—H2B20.9700
O3B—C20B1.462 (5)C3B—C4B1.527 (7)
O4B—C25B1.434 (5)C3B—H3B0.9800
O4B—H4B0.8200C4B—C29B1.535 (6)
O5B—C31B1.177 (7)C4B—C28B1.541 (8)
O6—C331.400 (11)C4B—C5B1.562 (6)
O6—H60.8200C5B—C6B1.539 (7)
C1A—C2A1.526 (6)C5B—C10B1.567 (7)
C1A—C10A1.541 (6)C5B—H5B0.9800
C1A—H1A10.9700C6B—C7B1.533 (7)
C1A—H1A20.9700C6B—H6B10.9700
C2A—C3A1.498 (7)C6B—H6B20.9700
C2A—H2A10.9700C7B—C8B1.553 (6)
C2A—H2A20.9700C7B—H7B10.9700
C3A—C4A1.528 (7)C7B—H7B20.9700
C3A—H3A0.9800C8B—C18B1.555 (6)
C4A—C28A1.542 (7)C8B—C14B1.560 (6)
C4A—C29A1.552 (6)C8B—C9B1.567 (6)
C4A—C5A1.557 (6)C9B—C11B1.539 (6)
C5A—C6A1.529 (6)C9B—C10B1.574 (6)
C5A—C10A1.553 (6)C9B—H9B0.9800
C5A—H5A0.9800C10B—C19B1.532 (6)
C6A—C7A1.541 (6)C11B—C12B1.518 (6)
C6A—H6A10.9700C11B—H11C0.9700
C6A—H6A20.9700C11B—H11D0.9700
C7A—C8A1.526 (5)C12B—C13B1.517 (5)
C7A—H7A10.9700C12B—H12B0.9800
C7A—H7A20.9700C13B—C17B1.552 (5)
C8A—C18A1.551 (5)C13B—C14B1.568 (6)
C8A—C9A1.568 (5)C13B—H13B0.9800
C8A—C14A1.573 (5)C14B—C15B1.529 (6)
C9A—C11A1.542 (5)C14B—C30B1.554 (6)
C9A—C10A1.558 (5)C15B—C16B1.532 (6)
C9A—H9A0.9800C15B—H15C0.9700
C10A—C19A1.548 (5)C15B—H15D0.9700
C11A—C12A1.522 (5)C16B—C17B1.565 (6)
C11A—H11A0.9700C16B—H16C0.9700
C11A—H11B0.9700C16B—H16D0.9700
C12A—C13A1.520 (5)C17B—C20B1.522 (6)
C12A—H12A0.9800C17B—H17B0.9800
C13A—C17A1.543 (5)C18B—H18D0.9600
C13A—C14A1.548 (5)C18B—H18E0.9600
C13A—H13A0.9800C18B—H18F0.9600
C14A—C15A1.533 (6)C19B—H19D0.9600
C14A—C30A1.556 (5)C19B—H19E0.9600
C15A—C16A1.536 (6)C19B—H19F0.9600
C15A—H15A0.9700C20B—C21B1.523 (6)
C15A—H15B0.9700C20B—C22B1.546 (6)
C16A—C17A1.569 (6)C21B—H21D0.9600
C16A—H16A0.9700C21B—H21E0.9600
C16A—H16B0.9700C21B—H21F0.9600
C17A—C20A1.545 (5)C22B—C23B1.516 (7)
C17A—H17A0.9800C22B—H22C0.9700
C18A—H18A0.9600C22B—H22D0.9700
C18A—H18B0.9600C23B—C24B1.521 (6)
C18A—H18C0.9600C23B—H23C0.9700
C19A—H19A0.9600C23B—H23D0.9700
C19A—H19B0.9600C24B—C25B1.520 (6)
C19A—H19C0.9600C24B—H24B0.9800
C20A—C21A1.529 (5)C25B—C26B1.517 (6)
C20A—C22A1.542 (6)C25B—C27B1.535 (6)
C21A—H21A0.9600C26B—H26D0.9600
C21A—H21B0.9600C26B—H26E0.9600
C21A—H21C0.9600C26B—H26F0.9600
C22A—C23A1.523 (6)C27B—H27D0.9600
C22A—H22A0.9700C27B—H27E0.9600
C22A—H22B0.9700C27B—H27F0.9600
C23A—C24A1.510 (6)C28B—H28D0.9600
C23A—H23A0.9700C28B—H28E0.9600
C23A—H23B0.9700C28B—H28F0.9600
C24A—C25A1.520 (6)C29B—H29D0.9600
C24A—H24A0.9800C29B—H29E0.9600
C25A—C27A1.508 (6)C29B—H29F0.9600
C25A—C26A1.530 (6)C30B—H30D0.9600
C26A—H26A0.9600C30B—H30E0.9600
C26A—H26B0.9600C30B—H30F0.9600
C26A—H26C0.9600C31B—C32B1.512 (9)
C27A—H27A0.9600C32B—H32D0.9600
C27A—H27B0.9600C32B—H32E0.9600
C27A—H27C0.9600C32B—H32F0.9600
C28A—H28A0.9600C33—C341.512 (15)
C28A—H28B0.9600C33—H33A0.9700
C28A—H28C0.9600C33—H33B0.9700
C29A—H29A0.9600C34—H34A0.9600
C29A—H29B0.9600C34—H34B0.9600
C29A—H29C0.9600C34—H34C0.9600
C31A—O1A—C3A119.2 (4)C10B—C1B—H1B1109.1
C12A—O2A—H2A109.5C2B—C1B—H1B2109.1
C24A—O3A—C20A108.8 (3)C10B—C1B—H1B2109.1
C25A—O4A—H4A109.5H1B1—C1B—H1B2107.8
C31B—O1B—C3B119.0 (4)C3B—C2B—C1B111.0 (5)
C12B—O2B—H2B109.5C3B—C2B—H2B1109.4
C24B—O3B—C20B108.4 (3)C1B—C2B—H2B1109.4
C25B—O4B—H4B109.5C3B—C2B—H2B2109.4
C33—O6—H6109.5C1B—C2B—H2B2109.4
C2A—C1A—C10A112.9 (4)H2B1—C2B—H2B2108.0
C2A—C1A—H1A1109.0O1B—C3B—C2B107.9 (5)
C10A—C1A—H1A1109.0O1B—C3B—C4B107.5 (4)
C2A—C1A—H1A2109.0C2B—C3B—C4B115.6 (4)
C10A—C1A—H1A2109.0O1B—C3B—H3B108.5
H1A1—C1A—H1A2107.8C2B—C3B—H3B108.5
C3A—C2A—C1A111.2 (4)C4B—C3B—H3B108.5
C3A—C2A—H2A1109.4C3B—C4B—C29B112.0 (5)
C1A—C2A—H2A1109.4C3B—C4B—C28B106.2 (5)
C3A—C2A—H2A2109.4C29B—C4B—C28B108.9 (5)
C1A—C2A—H2A2109.4C3B—C4B—C5B107.0 (4)
H2A1—C2A—H2A2108.0C29B—C4B—C5B113.7 (4)
O1A—C3A—C2A107.8 (4)C28B—C4B—C5B108.6 (5)
O1A—C3A—C4A108.3 (4)C6B—C5B—C4B113.2 (4)
C2A—C3A—C4A114.9 (4)C6B—C5B—C10B111.1 (4)
O1A—C3A—H3A108.5C4B—C5B—C10B117.1 (5)
C2A—C3A—H3A108.5C6B—C5B—H5B104.6
C4A—C3A—H3A108.5C4B—C5B—H5B104.6
C3A—C4A—C28A107.7 (4)C10B—C5B—H5B104.6
C3A—C4A—C29A110.9 (4)C7B—C6B—C5B110.1 (4)
C28A—C4A—C29A107.9 (4)C7B—C6B—H6B1109.6
C3A—C4A—C5A106.8 (4)C5B—C6B—H6B1109.6
C28A—C4A—C5A109.9 (4)C7B—C6B—H6B2109.6
C29A—C4A—C5A113.5 (4)C5B—C6B—H6B2109.6
C6A—C5A—C10A111.4 (4)H6B1—C6B—H6B2108.1
C6A—C5A—C4A113.4 (4)C6B—C7B—C8B113.4 (5)
C10A—C5A—C4A117.8 (4)C6B—C7B—H7B1108.9
C6A—C5A—H5A104.2C8B—C7B—H7B1108.9
C10A—C5A—H5A104.2C6B—C7B—H7B2108.9
C4A—C5A—H5A104.2C8B—C7B—H7B2108.9
C5A—C6A—C7A111.2 (4)H7B1—C7B—H7B2107.7
C5A—C6A—H6A1109.4C7B—C8B—C18B108.2 (4)
C7A—C6A—H6A1109.4C7B—C8B—C14B110.2 (4)
C5A—C6A—H6A2109.4C18B—C8B—C14B111.0 (4)
C7A—C6A—H6A2109.4C7B—C8B—C9B108.3 (4)
H6A1—C6A—H6A2108.0C18B—C8B—C9B111.9 (4)
C8A—C7A—C6A113.6 (4)C14B—C8B—C9B107.4 (3)
C8A—C7A—H7A1108.8C11B—C9B—C8B110.7 (3)
C6A—C7A—H7A1108.8C11B—C9B—C10B114.4 (4)
C8A—C7A—H7A2108.8C8B—C9B—C10B117.9 (4)
C6A—C7A—H7A2108.8C11B—C9B—H9B104.0
H7A1—C7A—H7A2107.7C8B—C9B—H9B104.0
C7A—C8A—C18A108.0 (3)C10B—C9B—H9B104.0
C7A—C8A—C9A108.4 (3)C1B—C10B—C19B109.0 (5)
C18A—C8A—C9A112.2 (3)C1B—C10B—C5B107.0 (4)
C7A—C8A—C14A110.8 (3)C19B—C10B—C5B114.3 (4)
C18A—C8A—C14A109.8 (3)C1B—C10B—C9B109.0 (3)
C9A—C8A—C14A107.7 (3)C19B—C10B—C9B112.1 (4)
C11A—C9A—C10A114.6 (3)C5B—C10B—C9B105.2 (4)
C11A—C9A—C8A111.1 (3)C12B—C11B—C9B112.9 (4)
C10A—C9A—C8A116.4 (3)C12B—C11B—H11C109.0
C11A—C9A—H9A104.4C9B—C11B—H11C109.0
C10A—C9A—H9A104.4C12B—C11B—H11D109.0
C8A—C9A—H9A104.4C9B—C11B—H11D109.0
C1A—C10A—C19A108.0 (4)H11C—C11B—H11D107.8
C1A—C10A—C5A106.4 (3)O2B—C12B—C13B113.3 (3)
C19A—C10A—C5A114.6 (4)O2B—C12B—C11B108.1 (4)
C1A—C10A—C9A108.6 (3)C13B—C12B—C11B109.6 (3)
C19A—C10A—C9A112.0 (3)O2B—C12B—H12B108.6
C5A—C10A—C9A106.9 (3)C13B—C12B—H12B108.6
C12A—C11A—C9A113.8 (3)C11B—C12B—H12B108.6
C12A—C11A—H11A108.8C12B—C13B—C17B120.7 (3)
C9A—C11A—H11A108.8C12B—C13B—C14B109.8 (3)
C12A—C11A—H11B108.8C17B—C13B—C14B104.4 (3)
C9A—C11A—H11B108.8C12B—C13B—H13B107.1
H11A—C11A—H11B107.7C17B—C13B—H13B107.1
O2A—C12A—C13A114.3 (3)C14B—C13B—H13B107.1
O2A—C12A—C11A107.1 (3)C15B—C14B—C30B105.6 (4)
C13A—C12A—C11A109.2 (3)C15B—C14B—C8B117.6 (4)
O2A—C12A—H12A108.7C30B—C14B—C8B112.4 (3)
C13A—C12A—H12A108.7C15B—C14B—C13B99.7 (3)
C11A—C12A—H12A108.7C30B—C14B—C13B110.7 (4)
C12A—C13A—C17A119.7 (3)C8B—C14B—C13B110.1 (4)
C12A—C13A—C14A109.3 (3)C14B—C15B—C16B104.6 (4)
C17A—C13A—C14A106.2 (3)C14B—C15B—H15C110.8
C12A—C13A—H13A107.0C16B—C15B—H15C110.8
C17A—C13A—H13A107.0C14B—C15B—H15D110.8
C14A—C13A—H13A107.0C16B—C15B—H15D110.8
C15A—C14A—C13A100.6 (3)H15C—C15B—H15D108.9
C15A—C14A—C30A105.9 (4)C15B—C16B—C17B105.8 (4)
C13A—C14A—C30A110.8 (3)C15B—C16B—H16C110.6
C15A—C14A—C8A118.0 (4)C17B—C16B—H16C110.6
C13A—C14A—C8A109.0 (3)C15B—C16B—H16D110.6
C30A—C14A—C8A112.0 (3)C17B—C16B—H16D110.6
C14A—C15A—C16A104.1 (4)H16C—C16B—H16D108.7
C14A—C15A—H15A110.9C20B—C17B—C13B118.2 (3)
C16A—C15A—H15A110.9C20B—C17B—C16B111.2 (4)
C14A—C15A—H15B110.9C13B—C17B—C16B104.3 (3)
C16A—C15A—H15B110.9C20B—C17B—H17B107.6
H15A—C15A—H15B109.0C13B—C17B—H17B107.6
C15A—C16A—C17A105.8 (3)C16B—C17B—H17B107.6
C15A—C16A—H16A110.6C8B—C18B—H18D109.5
C17A—C16A—H16A110.6C8B—C18B—H18E109.5
C15A—C16A—H16B110.6H18D—C18B—H18E109.5
C17A—C16A—H16B110.6C8B—C18B—H18F109.5
H16A—C16A—H16B108.7H18D—C18B—H18F109.5
C13A—C17A—C20A115.2 (3)H18E—C18B—H18F109.5
C13A—C17A—C16A104.2 (3)C10B—C19B—H19D109.5
C20A—C17A—C16A110.1 (4)C10B—C19B—H19E109.5
C13A—C17A—H17A109.0H19D—C19B—H19E109.5
C20A—C17A—H17A109.0C10B—C19B—H19F109.5
C16A—C17A—H17A109.0H19D—C19B—H19F109.5
C8A—C18A—H18A109.5H19E—C19B—H19F109.5
C8A—C18A—H18B109.5O3B—C20B—C17B109.4 (3)
H18A—C18A—H18B109.5O3B—C20B—C21B106.8 (3)
C8A—C18A—H18C109.5C17B—C20B—C21B110.4 (4)
H18A—C18A—H18C109.5O3B—C20B—C22B103.8 (3)
H18B—C18A—H18C109.5C17B—C20B—C22B114.7 (4)
C10A—C19A—H19A109.5C21B—C20B—C22B111.3 (4)
C10A—C19A—H19B109.5C20B—C21B—H21D109.5
H19A—C19A—H19B109.5C20B—C21B—H21E109.5
C10A—C19A—H19C109.5H21D—C21B—H21E109.5
H19A—C19A—H19C109.5C20B—C21B—H21F109.5
H19B—C19A—H19C109.5H21D—C21B—H21F109.5
O3A—C20A—C21A106.8 (3)H21E—C21B—H21F109.5
O3A—C20A—C22A104.8 (3)C23B—C22B—C20B106.7 (3)
C21A—C20A—C22A112.2 (4)C23B—C22B—H22C110.4
O3A—C20A—C17A107.6 (3)C20B—C22B—H22C110.4
C21A—C20A—C17A110.1 (4)C23B—C22B—H22D110.4
C22A—C20A—C17A114.8 (4)C20B—C22B—H22D110.4
C20A—C21A—H21A109.5H22C—C22B—H22D108.6
C20A—C21A—H21B109.5C22B—C23B—C24B103.2 (4)
H21A—C21A—H21B109.5C22B—C23B—H23C111.1
C20A—C21A—H21C109.5C24B—C23B—H23C111.1
H21A—C21A—H21C109.5C22B—C23B—H23D111.1
H21B—C21A—H21C109.5C24B—C23B—H23D111.1
C23A—C22A—C20A105.5 (4)H23C—C23B—H23D109.1
C23A—C22A—H22A110.6O3B—C24B—C25B109.3 (3)
C20A—C22A—H22A110.6O3B—C24B—C23B103.3 (3)
C23A—C22A—H22B110.6C25B—C24B—C23B118.1 (4)
C20A—C22A—H22B110.6O3B—C24B—H24B108.6
H22A—C22A—H22B108.8C25B—C24B—H24B108.6
C24A—C23A—C22A102.9 (3)C23B—C24B—H24B108.6
C24A—C23A—H23A111.2O4B—C25B—C26B110.9 (4)
C22A—C23A—H23A111.2O4B—C25B—C24B111.3 (4)
C24A—C23A—H23B111.2C26B—C25B—C24B110.2 (4)
C22A—C23A—H23B111.2O4B—C25B—C27B104.4 (4)
H23A—C23A—H23B109.1C26B—C25B—C27B111.5 (4)
O3A—C24A—C23A103.6 (3)C24B—C25B—C27B108.5 (4)
O3A—C24A—C25A110.0 (4)C25B—C26B—H26D109.5
C23A—C24A—C25A117.4 (4)C25B—C26B—H26E109.5
O3A—C24A—H24A108.5H26D—C26B—H26E109.5
C23A—C24A—H24A108.5C25B—C26B—H26F109.5
C25A—C24A—H24A108.5H26D—C26B—H26F109.5
O4A—C25A—C27A110.0 (4)H26E—C26B—H26F109.5
O4A—C25A—C24A111.2 (4)C25B—C27B—H27D109.5
C27A—C25A—C24A110.8 (4)C25B—C27B—H27E109.5
O4A—C25A—C26A105.1 (4)H27D—C27B—H27E109.5
C27A—C25A—C26A110.9 (4)C25B—C27B—H27F109.5
C24A—C25A—C26A108.6 (4)H27D—C27B—H27F109.5
C25A—C26A—H26A109.5H27E—C27B—H27F109.5
C25A—C26A—H26B109.5C4B—C28B—H28D109.5
H26A—C26A—H26B109.5C4B—C28B—H28E109.5
C25A—C26A—H26C109.5H28D—C28B—H28E109.5
H26A—C26A—H26C109.5C4B—C28B—H28F109.5
H26B—C26A—H26C109.5H28D—C28B—H28F109.5
C25A—C27A—H27A109.5H28E—C28B—H28F109.5
C25A—C27A—H27B109.5C4B—C29B—H29D109.5
H27A—C27A—H27B109.5C4B—C29B—H29E109.5
C25A—C27A—H27C109.5H29D—C29B—H29E109.5
H27A—C27A—H27C109.5C4B—C29B—H29F109.5
H27B—C27A—H27C109.5H29D—C29B—H29F109.5
C4A—C28A—H28A109.5H29E—C29B—H29F109.5
C4A—C28A—H28B109.5C14B—C30B—H30D109.5
H28A—C28A—H28B109.5C14B—C30B—H30E109.5
C4A—C28A—H28C109.5H30D—C30B—H30E109.5
H28A—C28A—H28C109.5C14B—C30B—H30F109.5
H28B—C28A—H28C109.5H30D—C30B—H30F109.5
C4A—C29A—H29A109.5H30E—C30B—H30F109.5
C4A—C29A—H29B109.5O5B—C31B—O1B124.6 (7)
H29A—C29A—H29B109.5O5B—C31B—C32B123.7 (6)
C4A—C29A—H29C109.5O1B—C31B—C32B111.7 (5)
H29A—C29A—H29C109.5C31B—C32B—H32D109.5
H29B—C29A—H29C109.5C31B—C32B—H32E109.5
C14A—C30A—H30A109.5H32D—C32B—H32E109.5
C14A—C30A—H30B109.5C31B—C32B—H32F109.5
H30A—C30A—H30B109.5H32D—C32B—H32F109.5
C14A—C30A—H30C109.5H32E—C32B—H32F109.5
H30A—C30A—H30C109.5O6—C33—C34111.8 (10)
H30B—C30A—H30C109.5O6—C33—H33A109.3
O5A—C31A—O1A122.5 (6)C34—C33—H33A109.3
O5A—C31A—C32A125.7 (6)O6—C33—H33B109.3
O1A—C31A—C32A111.8 (6)C34—C33—H33B109.3
C31A—C32A—H32A109.5H33A—C33—H33B107.9
C31A—C32A—H32B109.5C33—C34—H34A109.5
H32A—C32A—H32B109.5C33—C34—H34B109.5
C31A—C32A—H32C109.5H34A—C34—H34B109.5
H32A—C32A—H32C109.5C33—C34—H34C109.5
H32B—C32A—H32C109.5H34A—C34—H34C109.5
C2B—C1B—C10B112.5 (4)H34B—C34—H34C109.5
C2B—C1B—H1B1109.1
C10A—C1A—C2A—C3A57.6 (6)C10B—C1B—C2B—C3B58.3 (6)
C31A—O1A—C3A—C2A104.8 (6)C31B—O1B—C3B—C2B92.4 (7)
C31A—O1A—C3A—C4A130.3 (5)C31B—O1B—C3B—C4B142.3 (6)
C1A—C2A—C3A—O1A177.5 (4)C1B—C2B—C3B—O1B177.1 (4)
C1A—C2A—C3A—C4A56.6 (6)C1B—C2B—C3B—C4B56.7 (6)
O1A—C3A—C4A—C28A69.9 (5)O1B—C3B—C4B—C29B46.1 (6)
C2A—C3A—C4A—C28A169.5 (4)C2B—C3B—C4B—C29B74.5 (6)
O1A—C3A—C4A—C29A48.0 (5)O1B—C3B—C4B—C28B72.7 (5)
C2A—C3A—C4A—C29A72.7 (5)C2B—C3B—C4B—C28B166.7 (5)
O1A—C3A—C4A—C5A172.1 (4)O1B—C3B—C4B—C5B171.4 (4)
C2A—C3A—C4A—C5A51.5 (5)C2B—C3B—C4B—C5B50.8 (6)
C3A—C4A—C5A—C6A175.4 (4)C3B—C4B—C5B—C6B178.4 (4)
C28A—C4A—C5A—C6A58.9 (5)C29B—C4B—C5B—C6B57.4 (7)
C29A—C4A—C5A—C6A62.1 (5)C28B—C4B—C5B—C6B64.1 (6)
C3A—C4A—C5A—C10A52.0 (5)C3B—C4B—C5B—C10B50.3 (5)
C28A—C4A—C5A—C10A168.4 (4)C29B—C4B—C5B—C10B74.0 (6)
C29A—C4A—C5A—C10A70.6 (5)C28B—C4B—C5B—C10B164.6 (4)
C10A—C5A—C6A—C7A59.4 (5)C4B—C5B—C6B—C7B162.3 (4)
C4A—C5A—C6A—C7A164.9 (4)C10B—C5B—C6B—C7B63.5 (6)
C5A—C6A—C7A—C8A56.6 (5)C5B—C6B—C7B—C8B58.4 (6)
C6A—C7A—C8A—C18A71.1 (5)C6B—C7B—C8B—C18B71.8 (5)
C6A—C7A—C8A—C9A50.6 (5)C6B—C7B—C8B—C14B166.8 (4)
C6A—C7A—C8A—C14A168.6 (4)C6B—C7B—C8B—C9B49.6 (5)
C7A—C8A—C9A—C11A174.2 (3)C7B—C8B—C9B—C11B175.6 (4)
C18A—C8A—C9A—C11A66.7 (4)C18B—C8B—C9B—C11B65.3 (5)
C14A—C8A—C9A—C11A54.3 (4)C14B—C8B—C9B—C11B56.6 (4)
C7A—C8A—C9A—C10A52.1 (4)C7B—C8B—C9B—C10B50.1 (5)
C18A—C8A—C9A—C10A67.0 (4)C18B—C8B—C9B—C10B69.0 (5)
C14A—C8A—C9A—C10A172.0 (3)C14B—C8B—C9B—C10B169.0 (4)
C2A—C1A—C10A—C19A69.6 (5)C2B—C1B—C10B—C19B69.4 (6)
C2A—C1A—C10A—C5A53.9 (5)C2B—C1B—C10B—C5B54.8 (6)
C2A—C1A—C10A—C9A168.7 (4)C2B—C1B—C10B—C9B168.1 (4)
C6A—C5A—C10A—C1A172.8 (4)C6B—C5B—C10B—C1B174.4 (4)
C4A—C5A—C10A—C1A53.7 (5)C4B—C5B—C10B—C1B53.3 (5)
C6A—C5A—C10A—C19A67.9 (5)C6B—C5B—C10B—C19B64.8 (5)
C4A—C5A—C10A—C19A65.6 (5)C4B—C5B—C10B—C19B67.5 (5)
C6A—C5A—C10A—C9A56.9 (4)C6B—C5B—C10B—C9B58.6 (4)
C4A—C5A—C10A—C9A169.6 (4)C4B—C5B—C10B—C9B169.1 (4)
C11A—C9A—C10A—C1A58.4 (4)C11B—C9B—C10B—C1B58.5 (5)
C8A—C9A—C10A—C1A169.5 (3)C8B—C9B—C10B—C1B168.8 (4)
C11A—C9A—C10A—C19A60.9 (5)C11B—C9B—C10B—C19B62.2 (5)
C8A—C9A—C10A—C19A71.3 (5)C8B—C9B—C10B—C19B70.5 (5)
C11A—C9A—C10A—C5A172.8 (3)C11B—C9B—C10B—C5B173.0 (3)
C8A—C9A—C10A—C5A55.1 (4)C8B—C9B—C10B—C5B54.3 (4)
C10A—C9A—C11A—C12A172.2 (3)C8B—C9B—C11B—C12B56.9 (4)
C8A—C9A—C11A—C12A53.2 (5)C10B—C9B—C11B—C12B167.1 (3)
C9A—C11A—C12A—O2A179.7 (3)C9B—C11B—C12B—O2B179.0 (3)
C9A—C11A—C12A—C13A55.5 (4)C9B—C11B—C12B—C13B57.2 (4)
O2A—C12A—C13A—C17A56.7 (5)O2B—C12B—C13B—C17B59.2 (5)
C11A—C12A—C13A—C17A176.5 (3)C11B—C12B—C13B—C17B179.9 (4)
O2A—C12A—C13A—C14A179.3 (3)O2B—C12B—C13B—C14B179.4 (3)
C11A—C12A—C13A—C14A60.8 (4)C11B—C12B—C13B—C14B58.6 (4)
C12A—C13A—C14A—C15A170.0 (4)C7B—C8B—C14B—C15B69.6 (5)
C17A—C13A—C14A—C15A39.6 (4)C18B—C8B—C14B—C15B50.2 (5)
C12A—C13A—C14A—C30A58.3 (4)C9B—C8B—C14B—C15B172.7 (4)
C17A—C13A—C14A—C30A72.1 (4)C7B—C8B—C14B—C30B53.3 (5)
C12A—C13A—C14A—C8A65.3 (4)C18B—C8B—C14B—C30B173.1 (4)
C17A—C13A—C14A—C8A164.3 (3)C9B—C8B—C14B—C30B64.4 (5)
C7A—C8A—C14A—C15A67.1 (5)C7B—C8B—C14B—C13B177.2 (3)
C18A—C8A—C14A—C15A52.1 (5)C18B—C8B—C14B—C13B63.0 (5)
C9A—C8A—C14A—C15A174.5 (3)C9B—C8B—C14B—C13B59.5 (4)
C7A—C8A—C14A—C13A179.2 (3)C12B—C13B—C14B—C15B173.8 (3)
C18A—C8A—C14A—C13A61.6 (4)C17B—C13B—C14B—C15B43.0 (4)
C9A—C8A—C14A—C13A60.8 (4)C12B—C13B—C14B—C30B62.9 (4)
C7A—C8A—C14A—C30A56.2 (4)C17B—C13B—C14B—C30B67.9 (4)
C18A—C8A—C14A—C30A175.4 (4)C12B—C13B—C14B—C8B61.9 (4)
C9A—C8A—C14A—C30A62.2 (4)C17B—C13B—C14B—C8B167.3 (3)
C13A—C14A—C15A—C16A43.2 (4)C30B—C14B—C15B—C16B70.6 (4)
C30A—C14A—C15A—C16A72.2 (4)C8B—C14B—C15B—C16B163.1 (4)
C8A—C14A—C15A—C16A161.5 (3)C13B—C14B—C15B—C16B44.3 (4)
C14A—C15A—C16A—C17A31.4 (5)C14B—C15B—C16B—C17B29.4 (5)
C12A—C13A—C17A—C20A94.5 (4)C12B—C13B—C17B—C20B86.4 (5)
C14A—C13A—C17A—C20A141.3 (4)C14B—C13B—C17B—C20B149.5 (4)
C12A—C13A—C17A—C16A144.8 (4)C12B—C13B—C17B—C16B149.6 (4)
C14A—C13A—C17A—C16A20.6 (4)C14B—C13B—C17B—C16B25.5 (4)
C15A—C16A—C17A—C13A6.5 (5)C15B—C16B—C17B—C20B126.5 (4)
C15A—C16A—C17A—C20A117.6 (4)C15B—C16B—C17B—C13B1.9 (5)
C24A—O3A—C20A—C21A100.2 (4)C24B—O3B—C20B—C17B148.9 (3)
C24A—O3A—C20A—C22A19.0 (4)C24B—O3B—C20B—C21B91.7 (4)
C24A—O3A—C20A—C17A141.6 (3)C24B—O3B—C20B—C22B26.1 (4)
C13A—C17A—C20A—O3A53.4 (5)C13B—C17B—C20B—O3B56.3 (5)
C16A—C17A—C20A—O3A170.8 (3)C16B—C17B—C20B—O3B176.9 (3)
C13A—C17A—C20A—C21A169.5 (4)C13B—C17B—C20B—C21B173.6 (4)
C16A—C17A—C20A—C21A73.1 (4)C16B—C17B—C20B—C21B65.9 (5)
C13A—C17A—C20A—C22A62.8 (5)C13B—C17B—C20B—C22B59.7 (5)
C16A—C17A—C20A—C22A54.6 (5)C16B—C17B—C20B—C22B60.9 (5)
O3A—C20A—C22A—C23A5.1 (5)O3B—C20B—C22B—C23B2.9 (5)
C21A—C20A—C22A—C23A120.6 (4)C17B—C20B—C22B—C23B122.2 (4)
C17A—C20A—C22A—C23A112.8 (4)C21B—C20B—C22B—C23B111.6 (4)
C20A—C22A—C23A—C24A25.7 (5)C20B—C22B—C23B—C24B19.4 (5)
C20A—O3A—C24A—C23A35.8 (4)C20B—O3B—C24B—C25B165.4 (3)
C20A—O3A—C24A—C25A162.1 (3)C20B—O3B—C24B—C23B38.9 (4)
C22A—C23A—C24A—O3A37.2 (4)C22B—C23B—C24B—O3B34.9 (4)
C22A—C23A—C24A—C25A158.7 (4)C22B—C23B—C24B—C25B155.6 (4)
O3A—C24A—C25A—O4A62.8 (5)O3B—C24B—C25B—O4B71.2 (4)
C23A—C24A—C25A—O4A55.2 (5)C23B—C24B—C25B—O4B46.4 (5)
O3A—C24A—C25A—C27A59.9 (5)O3B—C24B—C25B—C26B52.3 (5)
C23A—C24A—C25A—C27A177.9 (4)C23B—C24B—C25B—C26B169.8 (4)
O3A—C24A—C25A—C26A178.1 (4)O3B—C24B—C25B—C27B174.6 (4)
C23A—C24A—C25A—C26A60.0 (5)C23B—C24B—C25B—C27B67.9 (5)
C3A—O1A—C31A—O5A3.2 (10)C3B—O1B—C31B—O5B4.5 (13)
C3A—O1A—C31A—C32A178.3 (5)C3B—O1B—C31B—C32B176.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A···O3A0.821.892.660 (3)155
02B—H2B···O3B0.821.822.629 (3)168
O4A—H4A···O2A0.821.992.805 (3)174
O4B—H4B···O2B0.822.082.887 (3)167
O6—H6···O4Ai0.822.122.924 (6)169
Symmetry code: (i) x, y+1, z.
(20S,24S)-3-Acetyl-20,24-epoxydammarane-3,12,25-triol (IV) top
Crystal data top
C32H54O5F(000) = 572
Mr = 518.75Dx = 1.156 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54187 Å
a = 10.910 (2) ÅCell parameters from 2872 reflections
b = 8.0370 (16) Åθ = 1.6–47.8°
c = 17.018 (3) ŵ = 0.60 mm1
β = 92.50 (3)°T = 153 K
V = 1490.8 (5) Å3Block, colourless
Z = 20.32 × 0.3 × 0.26 mm
Data collection top
Bruker P4
diffractometer
4294 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 74.5°, θmin = 6.7°
Absorption correction: multi-scan
(SADABS;Sheldrick, 2003)
h = 1313
Tmin = 0.762, Tmax = 0.870k = 109
31738 measured reflectionsl = 2121
5480 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068 w = 1/[σ2(Fo2) + (0.0862P)2 + 0.7202P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.208(Δ/σ)max = 0.001
S = 1.19Δρmax = 0.26 e Å3
5480 reflectionsΔρmin = 0.23 e Å3
345 parametersAbsolute structure: Flack (1983), ???? Friedel pairs
1 restraintAbsolute structure parameter: 0.19 (16)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7310 (5)0.4431 (7)0.6140 (3)0.0573 (13)
H1A0.68040.49830.65320.069*
H1B0.81820.46430.62910.069*
C20.7016 (6)0.5188 (7)0.5332 (3)0.0628 (14)
H2A0.61330.50360.51920.075*
H2B0.71870.63980.53500.075*
C30.7771 (5)0.4384 (7)0.4714 (3)0.0515 (11)
H30.86580.46150.48400.062*
C40.7587 (4)0.2498 (7)0.4639 (3)0.0499 (11)
C50.7796 (4)0.1762 (6)0.5484 (2)0.0424 (10)
H50.86730.20290.56290.051*
C60.7746 (5)0.0149 (7)0.5500 (3)0.0557 (12)
H6A0.81820.06050.50500.067*
H6B0.68810.05240.54530.067*
C70.8353 (5)0.0797 (7)0.6282 (3)0.0528 (12)
H7A0.83170.20280.62870.063*
H7B0.92280.04660.63110.063*
C80.7730 (4)0.0124 (6)0.7007 (3)0.0417 (10)
C90.7659 (4)0.1819 (6)0.6951 (2)0.0412 (9)
H90.85330.21960.69600.049*
C100.7069 (4)0.2536 (6)0.6160 (3)0.0435 (10)
C110.7139 (5)0.2550 (7)0.7700 (3)0.0509 (11)
H11A0.71400.37790.76590.061*
H11B0.62760.21850.77340.061*
C120.7854 (5)0.2045 (6)0.8459 (3)0.0513 (12)
H120.87020.25140.84520.062*
C130.7930 (4)0.0152 (6)0.8507 (3)0.0448 (10)
H130.70710.02820.84980.054*
C140.8542 (4)0.0551 (6)0.7773 (3)0.0448 (10)
C150.8632 (6)0.2419 (8)0.7990 (3)0.0644 (14)
H15A0.78240.29720.79200.077*
H15B0.92300.29990.76660.077*
C160.9069 (6)0.2395 (8)0.8862 (3)0.0637 (14)
H16A0.99730.24950.89120.076*
H16B0.87020.33310.91470.076*
C170.8646 (5)0.0694 (7)0.9206 (3)0.0531 (11)
H170.94030.00180.93170.064*
C180.6463 (5)0.0956 (7)0.7046 (3)0.0574 (13)
H18A0.60150.08380.65380.086*
H18B0.59990.04190.74560.086*
H18C0.65690.21390.71710.086*
C190.5678 (4)0.2249 (9)0.6088 (3)0.0632 (14)
H19A0.53040.30630.57220.095*
H19B0.53300.23780.66050.095*
H19C0.55130.11220.58900.095*
C200.8054 (5)0.0974 (6)0.9996 (3)0.0517 (12)
C210.9006 (6)0.1664 (10)1.0589 (3)0.0770 (18)
H21A0.96880.08751.06540.115*
H21B0.93140.27291.03980.115*
H21C0.86300.18311.10950.115*
C220.6884 (5)0.2033 (8)0.9967 (3)0.0643 (15)
H22A0.64030.18660.94670.077*
H22B0.70790.32301.00290.077*
C230.6192 (6)0.1385 (9)1.0664 (3)0.0690 (16)
H23A0.53020.16121.05970.083*
H23B0.65100.18821.11650.083*
C240.6458 (5)0.0474 (8)1.0634 (3)0.0589 (14)
H240.58240.10221.02800.071*
C250.6523 (6)0.1390 (9)1.1433 (3)0.0725 (17)
C260.6660 (9)0.3256 (11)1.1288 (5)0.103 (3)
H26A0.66940.38461.17920.154*
H26B0.59560.36571.09640.154*
H26C0.74180.34621.10150.154*
C270.5384 (7)0.1009 (13)1.1873 (4)0.103 (3)
H27A0.54080.01521.20490.155*
H27B0.46560.11871.15260.155*
H27C0.53490.17451.23310.155*
C280.8597 (6)0.1843 (8)0.4113 (3)0.0677 (15)
H28A0.86310.25390.36420.102*
H28B0.84110.06930.39590.102*
H28C0.93910.18810.44060.102*
C290.6337 (5)0.2079 (9)0.4243 (3)0.0649 (15)
H29A0.56880.26400.45220.097*
H29B0.62060.08730.42580.097*
H29C0.63170.24550.36940.097*
C300.9863 (4)0.0085 (8)0.7719 (3)0.0576 (13)
H30A0.98490.12640.75730.086*
H30B1.02820.05550.73210.086*
H30C1.03000.00480.82310.086*
C310.8041 (5)0.6493 (7)0.3741 (3)0.0558 (13)
C320.7493 (6)0.7211 (10)0.2996 (4)0.0800 (19)
H32A0.80860.79610.27640.120*
H32B0.67490.78320.31100.120*
H32C0.72860.63100.26260.120*
O10.7424 (4)0.5138 (5)0.3955 (2)0.0634 (10)
O20.7222 (5)0.2788 (6)0.9088 (2)0.0804 (14)
H20.75190.24320.95200.121*
O30.7642 (3)0.0628 (5)1.02883 (18)0.0533 (8)
O40.7541 (4)0.0799 (8)1.1907 (2)0.0894 (15)
H40.81360.06171.16220.134*
O50.8912 (4)0.7059 (6)0.4104 (3)0.0756 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.093 (4)0.036 (3)0.041 (2)0.001 (2)0.006 (2)0.003 (2)
C20.106 (4)0.038 (3)0.043 (3)0.002 (3)0.002 (3)0.002 (2)
C30.075 (3)0.043 (3)0.035 (2)0.007 (2)0.0066 (19)0.006 (2)
C40.063 (3)0.046 (3)0.040 (2)0.008 (2)0.0027 (19)0.000 (2)
C50.052 (2)0.040 (3)0.035 (2)0.0035 (18)0.0024 (17)0.0013 (19)
C60.087 (4)0.039 (3)0.042 (2)0.002 (2)0.007 (2)0.002 (2)
C70.079 (3)0.038 (3)0.042 (2)0.007 (2)0.007 (2)0.006 (2)
C80.052 (2)0.034 (2)0.039 (2)0.0027 (17)0.0017 (17)0.0004 (18)
C90.050 (2)0.035 (2)0.038 (2)0.0012 (17)0.0010 (17)0.0019 (19)
C100.050 (2)0.042 (3)0.038 (2)0.0006 (19)0.0011 (17)0.002 (2)
C110.072 (3)0.041 (3)0.040 (2)0.012 (2)0.002 (2)0.001 (2)
C120.080 (3)0.042 (3)0.032 (2)0.006 (2)0.004 (2)0.001 (2)
C130.055 (2)0.040 (2)0.039 (2)0.0060 (19)0.0043 (18)0.004 (2)
C140.052 (2)0.042 (3)0.041 (2)0.0047 (19)0.0057 (17)0.001 (2)
C150.091 (4)0.045 (3)0.058 (3)0.013 (3)0.011 (3)0.009 (3)
C160.082 (3)0.056 (3)0.053 (3)0.018 (3)0.008 (2)0.009 (3)
C170.062 (3)0.055 (3)0.043 (2)0.006 (2)0.0022 (19)0.007 (2)
C180.062 (3)0.057 (3)0.053 (3)0.018 (2)0.001 (2)0.007 (3)
C190.050 (3)0.081 (4)0.060 (3)0.005 (3)0.005 (2)0.009 (3)
C200.072 (3)0.043 (3)0.041 (2)0.002 (2)0.002 (2)0.007 (2)
C210.099 (4)0.082 (5)0.050 (3)0.021 (3)0.004 (3)0.021 (3)
C220.082 (4)0.060 (4)0.051 (3)0.015 (3)0.006 (2)0.002 (3)
C230.079 (4)0.075 (4)0.054 (3)0.014 (3)0.012 (3)0.005 (3)
C240.061 (3)0.072 (4)0.043 (2)0.005 (2)0.003 (2)0.010 (3)
C250.083 (4)0.087 (5)0.048 (3)0.018 (3)0.003 (2)0.003 (3)
C260.153 (8)0.074 (5)0.082 (5)0.009 (5)0.001 (5)0.013 (4)
C270.100 (5)0.139 (8)0.073 (4)0.016 (5)0.031 (4)0.010 (5)
C280.097 (4)0.063 (4)0.045 (3)0.002 (3)0.021 (3)0.005 (3)
C290.078 (3)0.073 (4)0.043 (3)0.016 (3)0.013 (2)0.007 (3)
C300.050 (2)0.071 (4)0.052 (3)0.005 (2)0.005 (2)0.008 (3)
C310.070 (3)0.046 (3)0.053 (3)0.009 (2)0.016 (2)0.012 (2)
C320.092 (4)0.085 (5)0.065 (4)0.021 (4)0.019 (3)0.034 (4)
O10.086 (2)0.056 (2)0.0473 (19)0.0093 (18)0.0097 (17)0.0172 (18)
O20.137 (4)0.065 (3)0.0395 (18)0.038 (3)0.014 (2)0.002 (2)
O30.068 (2)0.052 (2)0.0407 (16)0.0001 (15)0.0023 (13)0.0044 (16)
O40.105 (3)0.114 (4)0.048 (2)0.018 (3)0.011 (2)0.003 (3)
O50.082 (3)0.067 (3)0.078 (3)0.012 (2)0.010 (2)0.011 (2)
Geometric parameters (Å, º) top
C1—H1A0.9900C18—H18A0.9800
C1—H1B0.9900C18—H18B0.9800
C1—C21.525 (7)C18—H18C0.9800
C1—C101.546 (7)C19—H19A0.9800
C2—H2A0.9900C19—H19B0.9800
C2—H2B0.9900C19—H19C0.9800
C2—C31.510 (7)C20—C211.521 (7)
C3—H31.0000C20—C221.533 (7)
C3—C41.533 (7)C20—O31.459 (6)
C3—O11.461 (5)C21—H21A0.9800
C4—C51.563 (6)C21—H21B0.9800
C4—C281.542 (7)C21—H21C0.9800
C4—C291.532 (7)C22—H22A0.9900
C5—H51.0000C22—H22B0.9900
C5—C61.537 (7)C22—C231.524 (8)
C5—C101.556 (6)C23—H23A0.9900
C6—H6A0.9900C23—H23B0.9900
C6—H6B0.9900C23—C241.523 (9)
C6—C71.550 (7)C24—H241.0000
C7—H7A0.9900C24—C251.545 (8)
C7—H7B0.9900C24—O31.447 (6)
C7—C81.532 (6)C25—C261.528 (11)
C8—C91.566 (6)C25—C271.510 (9)
C8—C141.582 (6)C25—O41.426 (7)
C8—C181.539 (6)C26—H26A0.9800
C9—H91.0000C26—H26B0.9800
C9—C101.575 (6)C26—H26C0.9800
C9—C111.536 (6)C27—H27A0.9800
C10—C191.535 (6)C27—H27B0.9800
C11—H11A0.9900C27—H27C0.9800
C11—H11B0.9900C28—H28A0.9800
C11—C121.533 (6)C28—H28B0.9800
C12—H121.0000C28—H28C0.9800
C12—C131.526 (7)C29—H29A0.9800
C12—O21.429 (6)C29—H29B0.9800
C13—H131.0000C29—H29C0.9800
C13—C141.549 (6)C30—H30A0.9800
C13—C171.551 (6)C30—H30B0.9800
C14—C151.548 (8)C30—H30C0.9800
C14—C301.535 (7)C31—C321.494 (7)
C15—H15A0.9900C31—O11.339 (7)
C15—H15B0.9900C31—O51.200 (7)
C15—C161.538 (8)C32—H32A0.9800
C16—H16A0.9900C32—H32B0.9800
C16—H16B0.9900C32—H32C0.9800
C16—C171.565 (8)O2—H20.8400
C17—H171.0000O4—H40.8400
C17—C201.533 (7)
H1A—C1—H1B107.8C13—C17—H17106.9
C2—C1—H1A109.1C16—C17—H17106.9
C2—C1—H1B109.1C20—C17—C13121.3 (4)
C2—C1—C10112.6 (4)C20—C17—C16110.0 (4)
C10—C1—H1A109.1C20—C17—H17106.9
C10—C1—H1B109.1C8—C18—H18A109.5
C1—C2—H2A109.4C8—C18—H18B109.5
C1—C2—H2B109.4C8—C18—H18C109.5
H2A—C2—H2B108.0H18A—C18—H18B109.5
C3—C2—C1111.0 (4)H18A—C18—H18C109.5
C3—C2—H2A109.4H18B—C18—H18C109.5
C3—C2—H2B109.4C10—C19—H19A109.5
C2—C3—H3108.9C10—C19—H19B109.5
C2—C3—C4114.1 (4)C10—C19—H19C109.5
C4—C3—H3108.9H19A—C19—H19B109.5
O1—C3—C2108.1 (4)H19A—C19—H19C109.5
O1—C3—H3108.9H19B—C19—H19C109.5
O1—C3—C4108.0 (4)C21—C20—C17109.5 (4)
C3—C4—C5106.5 (4)C21—C20—C22111.3 (5)
C3—C4—C28107.0 (4)C22—C20—C17115.8 (4)
C28—C4—C5108.9 (4)O3—C20—C17108.5 (4)
C29—C4—C3111.4 (5)O3—C20—C21107.9 (4)
C29—C4—C5114.4 (4)O3—C20—C22103.4 (4)
C29—C4—C28108.4 (5)C20—C21—H21A109.5
C4—C5—H5104.2C20—C21—H21B109.5
C6—C5—C4113.0 (4)C20—C21—H21C109.5
C6—C5—H5104.2H21A—C21—H21B109.5
C6—C5—C10111.5 (4)H21A—C21—H21C109.5
C10—C5—C4118.1 (4)H21B—C21—H21C109.5
C10—C5—H5104.2C20—C22—H22A111.2
C5—C6—H6A109.7C20—C22—H22B111.2
C5—C6—H6B109.7H22A—C22—H22B109.1
C5—C6—C7109.7 (4)C23—C22—C20103.0 (5)
H6A—C6—H6B108.2C23—C22—H22A111.2
C7—C6—H6A109.7C23—C22—H22B111.2
C7—C6—H6B109.7C22—C23—H23A111.4
C6—C7—H7A109.1C22—C23—H23B111.4
C6—C7—H7B109.1H23A—C23—H23B109.2
H7A—C7—H7B107.8C24—C23—C22102.0 (5)
C8—C7—C6112.6 (4)C24—C23—H23A111.4
C8—C7—H7A109.1C24—C23—H23B111.4
C8—C7—H7B109.1C23—C24—H24108.9
C7—C8—C9109.0 (4)C23—C24—C25116.1 (5)
C7—C8—C14109.5 (4)C25—C24—H24108.9
C7—C8—C18108.3 (4)O3—C24—C23105.8 (4)
C9—C8—C14106.9 (4)O3—C24—H24108.9
C18—C8—C9113.2 (4)O3—C24—C25108.1 (4)
C18—C8—C14110.0 (4)C26—C25—C24109.1 (5)
C8—C9—H9104.9C27—C25—C24109.5 (6)
C8—C9—C10115.7 (4)C27—C25—C26111.6 (7)
C10—C9—H9104.9O4—C25—C24110.1 (5)
C11—C9—C8110.5 (4)O4—C25—C26109.8 (7)
C11—C9—H9104.9O4—C25—C27106.8 (6)
C11—C9—C10114.7 (4)C25—C26—H26A109.5
C1—C10—C5106.6 (4)C25—C26—H26B109.5
C1—C10—C9108.4 (4)C25—C26—H26C109.5
C5—C10—C9106.4 (3)H26A—C26—H26B109.5
C19—C10—C1108.3 (4)H26A—C26—H26C109.5
C19—C10—C5114.5 (4)H26B—C26—H26C109.5
C19—C10—C9112.3 (4)C25—C27—H27A109.5
C9—C11—H11A108.8C25—C27—H27B109.5
C9—C11—H11B108.8C25—C27—H27C109.5
H11A—C11—H11B107.7H27A—C27—H27B109.5
C12—C11—C9113.9 (4)H27A—C27—H27C109.5
C12—C11—H11A108.8H27B—C27—H27C109.5
C12—C11—H11B108.8C4—C28—H28A109.5
C11—C12—H12109.1C4—C28—H28B109.5
C13—C12—C11109.5 (4)C4—C28—H28C109.5
C13—C12—H12109.1H28A—C28—H28B109.5
O2—C12—C11106.0 (4)H28A—C28—H28C109.5
O2—C12—H12109.1H28B—C28—H28C109.5
O2—C12—C13113.8 (4)C4—C29—H29A109.5
C12—C13—H13107.3C4—C29—H29B109.5
C12—C13—C14110.2 (4)C4—C29—H29C109.5
C12—C13—C17120.2 (4)H29A—C29—H29B109.5
C14—C13—H13107.3H29A—C29—H29C109.5
C14—C13—C17103.8 (4)H29B—C29—H29C109.5
C17—C13—H13107.3C14—C30—H30A109.5
C13—C14—C8109.9 (3)C14—C30—H30B109.5
C15—C14—C8115.7 (4)C14—C30—H30C109.5
C15—C14—C13100.7 (4)H30A—C30—H30B109.5
C30—C14—C8111.9 (4)H30A—C30—H30C109.5
C30—C14—C13111.4 (4)H30B—C30—H30C109.5
C30—C14—C15106.7 (4)O1—C31—C32111.0 (5)
C14—C15—H15A111.1O5—C31—C32124.7 (5)
C14—C15—H15B111.1O5—C31—O1124.3 (5)
H15A—C15—H15B109.0C31—C32—H32A109.5
C16—C15—C14103.4 (5)C31—C32—H32B109.5
C16—C15—H15A111.1C31—C32—H32C109.5
C16—C15—H15B111.1H32A—C32—H32B109.5
C15—C16—H16A110.4H32A—C32—H32C109.5
C15—C16—H16B110.4H32B—C32—H32C109.5
C15—C16—C17106.7 (4)C31—O1—C3117.6 (4)
H16A—C16—H16B108.6C12—O2—H2109.5
C17—C16—H16A110.4C24—O3—C20110.9 (4)
C17—C16—H16B110.4C25—O4—H4109.5
C13—C17—C16104.0 (4)
C1—C2—C3—C458.6 (6)C13—C14—C15—C1643.0 (5)
C1—C2—C3—O1178.7 (4)C13—C17—C20—C21174.4 (5)
C2—C1—C10—C553.8 (5)C13—C17—C20—C2258.9 (7)
C2—C1—C10—C9168.0 (4)C13—C17—C20—O356.9 (6)
C2—C1—C10—C1969.9 (6)C14—C8—C9—C10170.7 (3)
C2—C3—C4—C552.5 (5)C14—C8—C9—C1156.9 (5)
C2—C3—C4—C28168.9 (4)C14—C13—C17—C1629.1 (5)
C2—C3—C4—C2972.9 (5)C14—C13—C17—C20153.5 (5)
C2—C3—O1—C3189.6 (5)C14—C15—C16—C1725.5 (6)
C3—C4—C5—C6175.4 (4)C15—C16—C17—C132.2 (6)
C3—C4—C5—C1051.9 (5)C15—C16—C17—C20133.6 (5)
C4—C3—O1—C31146.6 (4)C16—C17—C20—C2164.0 (6)
C4—C5—C6—C7162.2 (4)C16—C17—C20—C2262.8 (6)
C4—C5—C10—C153.0 (5)C16—C17—C20—O3178.5 (4)
C4—C5—C10—C9168.5 (4)C17—C13—C14—C8167.4 (4)
C4—C5—C10—C1966.8 (6)C17—C13—C14—C1544.8 (5)
C5—C6—C7—C858.8 (6)C17—C13—C14—C3068.1 (5)
C6—C5—C10—C1173.7 (4)C17—C20—C22—C23152.1 (5)
C6—C5—C10—C958.1 (5)C17—C20—O3—C24139.4 (4)
C6—C5—C10—C1966.5 (5)C18—C8—C9—C1068.1 (5)
C6—C7—C8—C952.6 (5)C18—C8—C9—C1164.3 (5)
C6—C7—C8—C14169.2 (4)C18—C8—C14—C1362.2 (5)
C6—C7—C8—C1870.9 (6)C18—C8—C14—C1551.0 (5)
C7—C8—C9—C1052.4 (5)C18—C8—C14—C30173.6 (4)
C7—C8—C9—C11175.2 (4)C20—C22—C23—C2438.1 (6)
C7—C8—C14—C13179.0 (4)C21—C20—C22—C2382.0 (6)
C7—C8—C14—C1567.8 (5)C21—C20—O3—C24102.0 (5)
C7—C8—C14—C3054.7 (5)C22—C20—O3—C2415.9 (5)
C8—C9—C10—C1168.8 (4)C22—C23—C24—C25148.7 (5)
C8—C9—C10—C554.5 (5)C22—C23—C24—O328.9 (6)
C8—C9—C10—C1971.5 (5)C23—C24—C25—C26174.1 (6)
C8—C9—C11—C1256.0 (5)C23—C24—C25—C2751.8 (7)
C8—C14—C15—C16161.4 (4)C23—C24—C25—O465.4 (7)
C9—C8—C14—C1361.1 (5)C23—C24—O3—C208.2 (5)
C9—C8—C14—C15174.3 (4)C25—C24—O3—C20133.1 (4)
C9—C8—C14—C3063.2 (5)C28—C4—C5—C660.4 (6)
C9—C11—C12—C1355.0 (6)C28—C4—C5—C10167.0 (4)
C9—C11—C12—O2178.2 (4)C29—C4—C5—C661.1 (6)
C10—C1—C2—C358.9 (6)C29—C4—C5—C1071.6 (6)
C10—C5—C6—C762.0 (5)C30—C14—C15—C1673.4 (5)
C10—C9—C11—C12171.0 (4)C32—C31—O1—C3174.1 (5)
C11—C9—C10—C160.7 (5)O1—C3—C4—C5172.6 (4)
C11—C9—C10—C5175.0 (4)O1—C3—C4—C2871.0 (5)
C11—C9—C10—C1958.9 (6)O1—C3—C4—C2947.2 (5)
C11—C12—C13—C1457.4 (5)O2—C12—C13—C14175.9 (4)
C11—C12—C13—C17177.9 (4)O2—C12—C13—C1763.6 (6)
C12—C13—C14—C862.7 (5)O3—C20—C22—C2333.5 (5)
C12—C13—C14—C15174.7 (4)O3—C24—C25—C2667.3 (7)
C12—C13—C14—C3061.9 (5)O3—C24—C25—C27170.3 (6)
C12—C13—C17—C16152.7 (5)O3—C24—C25—O453.2 (7)
C12—C13—C17—C2082.8 (6)O5—C31—O1—C35.4 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.841.952.705 (5)148
O4—H4···O30.842.312.765 (5)115
 

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