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The title compound, (I), 3β,15α,25-trihydr­oxy-16,23-dioxo-6α,19α-epidi­oxy-9,10-seco-9,19-cyclo­lanost-5(10),9(11)-diene 3-O-α-L-arabinopyran­oside, crystallizes as the monohydrate, C35H52O11·H2O. It has an endo-epoxide rather than two OH groups on its seven-membered ring. The O—O distance is 1.473 (3) Å, and the C—O—O—C torsion angle is −30.4 (3)°. O...O distances in hydrogen bonds are in the range 2.679 (3)–3.015 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014018/fl2114sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014018/fl2114Isup2.hkl
Contains datablock I

CCDC reference: 647209

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.081
  • Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 3870 Count of symmetry unique reflns 4009 Completeness (_total/calc) 96.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C34 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 14 ALERT level G = General alerts; check 13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL018_ALERT_1_A The author field is longer than 65 characters. Please check that the author/address loop has been completed according to the CIF specification. Author = USA, National Center for Natural Products Research University of issippi University MS 38677 USA and Department of Pharmacognosy School of Pharmacy University of Mississippi University MS 38677 PUBL019_ALERT_1_A The author field is longer than 8 words. Please check that the author/address loop has been completed according to the CIF specification. Author = USA, National Center for Natural Products Research University of issippi University MS 38677 USA and Department of Pharmacognosy School of Pharmacy University of Mississippi University MS 38677
2 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3β,15α,25-Trihydroxy-6α,19α-epidioxy- 16,23-dione-9,10-seco-9,19-cyclolanost-5(10),9(11)-diene 3-O-α-L-arabinopyranoside top
Crystal data top
C35H52O11·H2OF(000) = 1440
Mr = 666.78Dx = 1.288 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3458 reflections
a = 7.6672 (15) Åθ = 2.5–26.3°
b = 15.324 (3) ŵ = 0.10 mm1
c = 29.260 (6) ÅT = 100 K
V = 3437.8 (12) Å3Needle, colourless
Z = 40.42 × 0.05 × 0.05 mm
Data collection top
Nonius KappaCCD (with Oxford Cryostream)
diffractometer
2917 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 26.4°, θmin = 2.7°
ω scans with κ offsetsh = 99
11976 measured reflectionsk = 1818
3870 independent reflectionsl = 3636
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0264P)2 + 0.7561P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3870 reflectionsΔρmax = 0.21 e Å3
443 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (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
O10.5938 (2)0.54869 (12)0.55642 (6)0.0179 (5)
O20.9810 (3)0.72012 (14)0.67590 (7)0.0302 (6)
O30.8662 (3)0.68290 (14)0.71125 (7)0.0303 (6)
O41.2345 (3)0.38793 (15)0.62527 (7)0.0242 (5)
H41.24420.39110.59670.036*
O51.1745 (3)0.21578 (14)0.65149 (8)0.0350 (6)
O60.9700 (3)0.06553 (14)0.61060 (7)0.0304 (6)
O71.3166 (3)0.02478 (14)0.58416 (7)0.0345 (6)
H71.21960.04160.57420.052*
O80.3311 (2)0.52353 (12)0.52308 (6)0.0196 (5)
O90.7286 (2)0.39408 (13)0.52032 (9)0.0304 (6)
H90.74950.34050.51770.046*
O100.4532 (3)0.26318 (12)0.49890 (7)0.0217 (5)
H100.43940.25230.52680.033*
O110.1704 (3)0.35883 (13)0.53364 (6)0.0236 (5)
H110.10030.31770.52890.035*
C10.4852 (4)0.6541 (2)0.63134 (10)0.0221 (7)
H1A0.41900.69390.65160.027*
H1B0.43880.59440.63570.027*
C20.4585 (4)0.68180 (19)0.58176 (10)0.0209 (7)
H2A0.34200.66240.57120.025*
H2B0.46290.74620.57960.025*
C30.5978 (4)0.64263 (18)0.55121 (10)0.0170 (7)
H30.57270.65810.51870.020*
C40.7823 (4)0.67447 (19)0.56395 (9)0.0171 (7)
C50.8050 (4)0.66532 (18)0.61505 (9)0.0182 (7)
C60.9835 (4)0.6636 (2)0.63668 (10)0.0229 (7)
H61.06800.68850.61420.027*
C71.0470 (4)0.57050 (19)0.64930 (10)0.0214 (7)
H7A1.11860.54790.62370.026*
H7B1.12370.57480.67640.026*
C80.9025 (4)0.50382 (18)0.65960 (10)0.0173 (7)
H80.83700.49520.63040.021*
C90.7700 (4)0.5358 (2)0.69453 (9)0.0192 (7)
C100.6744 (4)0.65584 (18)0.64454 (10)0.0178 (7)
C110.6909 (4)0.48231 (19)0.72402 (10)0.0204 (7)
H11A0.60840.50740.74440.024*
C120.7217 (4)0.38508 (19)0.72761 (9)0.0214 (7)
H12A0.60870.35470.73150.026*
H12B0.79460.37260.75480.026*
C130.8127 (4)0.35079 (19)0.68487 (9)0.0169 (7)
C140.9709 (4)0.41340 (19)0.67377 (9)0.0167 (7)
C151.0648 (4)0.36076 (19)0.63658 (10)0.0192 (7)
H150.99170.36110.60830.023*
C161.0609 (4)0.2700 (2)0.65704 (10)0.0205 (7)
C170.9045 (4)0.25988 (18)0.68912 (10)0.0186 (7)
H170.95350.25730.72080.022*
C180.6780 (4)0.3488 (2)0.64580 (10)0.0223 (7)
H18A0.58520.30720.65330.033*
H18B0.73540.33080.61740.033*
H18C0.62760.40710.64180.033*
C190.7238 (4)0.63203 (19)0.69266 (10)0.0216 (7)
H190.61940.64150.71250.026*
C200.8014 (4)0.17491 (19)0.68247 (10)0.0212 (7)
H200.75330.17350.65070.025*
C210.6501 (4)0.1692 (2)0.71656 (11)0.0310 (8)
H21A0.59090.11290.71310.047*
H21B0.56720.21660.71060.047*
H21C0.69540.17450.74780.047*
C220.9189 (4)0.0942 (2)0.68969 (10)0.0245 (8)
H22A1.00060.10760.71490.029*
H22B0.84370.04560.70010.029*
C231.0250 (4)0.06180 (19)0.64969 (10)0.0251 (8)
C241.1969 (4)0.0197 (2)0.66146 (10)0.0259 (8)
H24A1.17700.02090.68730.031*
H24B1.27680.06590.67240.031*
C251.2900 (4)0.03084 (19)0.62352 (10)0.0258 (8)
C261.1852 (5)0.1109 (2)0.60965 (12)0.0399 (9)
H26A1.06680.09320.60110.060*
H26B1.17970.15180.63540.060*
H26C1.24150.13930.58350.060*
C271.4730 (4)0.0559 (2)0.63875 (12)0.0402 (9)
H27A1.53210.08710.61400.060*
H27B1.46580.09370.66570.060*
H27C1.53880.00310.64640.060*
C281.0967 (4)0.42256 (19)0.71508 (9)0.0202 (7)
H28A1.20900.44550.70450.030*
H28B1.11430.36530.72920.030*
H28C1.04620.46270.73750.030*
C290.8033 (4)0.77048 (19)0.54924 (10)0.0255 (8)
H29A0.71620.80640.56500.038*
H29B0.78650.77520.51610.038*
H29C0.92050.79090.55720.038*
C300.9160 (4)0.6196 (2)0.53750 (10)0.0249 (8)
H30A1.03370.64150.54370.037*
H30B0.89200.62380.50470.037*
H30C0.90760.55850.54720.037*
C310.5128 (4)0.50448 (18)0.52093 (10)0.0171 (7)
H310.56120.52470.49100.021*
C320.5458 (4)0.40691 (19)0.52657 (10)0.0195 (7)
H320.51180.38840.55810.023*
C330.4400 (4)0.35558 (18)0.49153 (10)0.0180 (7)
H330.48920.36850.46060.022*
C340.2492 (4)0.38399 (19)0.49156 (10)0.0196 (7)
H340.18660.35540.46560.023*
C350.2384 (4)0.48186 (18)0.48652 (10)0.0213 (7)
H35A0.28940.49960.45690.026*
H35B0.11470.50040.48700.026*
O1W0.4361 (3)0.20066 (15)0.58443 (8)0.0291 (6)
H1W0.411 (5)0.145 (2)0.5843 (12)0.044*
H2W0.360 (5)0.225 (2)0.6079 (11)0.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0188 (11)0.0131 (10)0.0218 (10)0.0007 (10)0.0028 (9)0.0004 (9)
O20.0317 (13)0.0283 (12)0.0306 (12)0.0065 (12)0.0038 (12)0.0027 (11)
O30.0361 (14)0.0288 (13)0.0261 (12)0.0081 (12)0.0007 (11)0.0011 (11)
O40.0158 (11)0.0325 (12)0.0244 (11)0.0031 (11)0.0059 (10)0.0022 (11)
O50.0334 (13)0.0234 (12)0.0481 (15)0.0073 (13)0.0195 (12)0.0010 (11)
O60.0413 (14)0.0304 (13)0.0194 (11)0.0047 (12)0.0064 (11)0.0007 (10)
O70.0472 (15)0.0300 (13)0.0261 (12)0.0034 (14)0.0034 (12)0.0036 (11)
O80.0139 (10)0.0201 (11)0.0248 (11)0.0027 (10)0.0029 (9)0.0059 (10)
O90.0132 (11)0.0182 (11)0.0597 (15)0.0038 (10)0.0039 (11)0.0044 (12)
O100.0304 (12)0.0154 (11)0.0194 (10)0.0019 (10)0.0026 (11)0.0003 (9)
O110.0197 (11)0.0291 (13)0.0220 (11)0.0090 (11)0.0050 (10)0.0066 (10)
C10.0199 (16)0.0214 (17)0.0251 (17)0.0055 (15)0.0039 (14)0.0026 (15)
C20.0149 (15)0.0171 (16)0.0306 (17)0.0016 (15)0.0030 (14)0.0001 (15)
C30.0184 (16)0.0118 (15)0.0208 (16)0.0012 (14)0.0022 (14)0.0023 (13)
C40.0137 (16)0.0169 (16)0.0207 (15)0.0023 (15)0.0009 (13)0.0014 (14)
C50.0202 (16)0.0106 (15)0.0240 (16)0.0015 (15)0.0028 (14)0.0021 (14)
C60.0197 (16)0.0250 (18)0.0240 (17)0.0009 (16)0.0016 (14)0.0055 (15)
C70.0137 (15)0.0254 (17)0.0250 (16)0.0038 (16)0.0015 (14)0.0002 (14)
C80.0172 (16)0.0183 (16)0.0165 (15)0.0022 (15)0.0012 (13)0.0003 (14)
C90.0161 (16)0.0256 (17)0.0160 (15)0.0007 (16)0.0010 (13)0.0024 (14)
C100.0205 (16)0.0117 (15)0.0211 (16)0.0012 (15)0.0021 (15)0.0018 (14)
C110.0191 (16)0.0229 (17)0.0191 (16)0.0067 (16)0.0035 (14)0.0044 (14)
C120.0199 (17)0.0274 (18)0.0167 (15)0.0016 (16)0.0021 (14)0.0004 (14)
C130.0158 (15)0.0196 (16)0.0154 (15)0.0033 (15)0.0009 (14)0.0003 (13)
C140.0172 (15)0.0218 (17)0.0112 (14)0.0035 (15)0.0007 (13)0.0009 (13)
C150.0131 (15)0.0260 (18)0.0185 (16)0.0002 (15)0.0012 (14)0.0005 (14)
C160.0181 (17)0.0233 (18)0.0201 (16)0.0019 (16)0.0003 (14)0.0053 (14)
C170.0210 (16)0.0203 (17)0.0146 (15)0.0015 (16)0.0003 (14)0.0005 (14)
C180.0167 (15)0.0262 (18)0.0241 (16)0.0020 (16)0.0003 (15)0.0006 (15)
C190.0211 (17)0.0200 (17)0.0238 (16)0.0005 (16)0.0018 (15)0.0008 (14)
C200.0269 (18)0.0202 (17)0.0164 (15)0.0038 (16)0.0017 (14)0.0000 (14)
C210.0294 (19)0.0303 (19)0.0334 (19)0.0083 (18)0.0066 (16)0.0029 (17)
C220.0314 (19)0.0210 (17)0.0210 (16)0.0040 (17)0.0014 (15)0.0060 (14)
C230.0351 (19)0.0141 (16)0.0260 (18)0.0045 (17)0.0036 (16)0.0018 (15)
C240.037 (2)0.0191 (17)0.0219 (16)0.0001 (17)0.0055 (16)0.0037 (14)
C250.034 (2)0.0177 (16)0.0257 (17)0.0019 (16)0.0053 (16)0.0052 (14)
C260.044 (2)0.0242 (19)0.051 (2)0.002 (2)0.000 (2)0.0050 (18)
C270.040 (2)0.041 (2)0.040 (2)0.007 (2)0.0036 (18)0.0021 (19)
C280.0224 (17)0.0190 (17)0.0193 (15)0.0002 (15)0.0026 (14)0.0005 (14)
C290.0241 (17)0.0230 (17)0.0294 (18)0.0057 (16)0.0011 (16)0.0056 (15)
C300.0193 (16)0.0292 (18)0.0262 (17)0.0000 (16)0.0039 (15)0.0013 (15)
C310.0169 (15)0.0177 (16)0.0167 (15)0.0004 (14)0.0020 (13)0.0014 (14)
C320.0114 (15)0.0220 (17)0.0249 (16)0.0029 (14)0.0040 (14)0.0006 (15)
C330.0214 (16)0.0136 (15)0.0190 (15)0.0011 (15)0.0037 (14)0.0027 (13)
C340.0211 (16)0.0221 (17)0.0155 (15)0.0002 (15)0.0020 (14)0.0025 (14)
C350.0185 (16)0.0250 (17)0.0204 (16)0.0046 (15)0.0049 (14)0.0057 (14)
O1W0.0323 (14)0.0260 (13)0.0291 (12)0.0003 (12)0.0090 (11)0.0007 (11)
Geometric parameters (Å, º) top
O1—C311.387 (3)C14—C281.553 (4)
O1—C31.448 (3)C15—C161.514 (4)
O2—C61.438 (3)C15—H151.0000
O2—O31.473 (3)C16—C171.530 (4)
O3—C191.447 (4)C17—C201.536 (4)
O4—C151.406 (3)C17—H171.0000
O4—H40.8400C18—H18A0.9800
O5—C161.215 (3)C18—H18B0.9800
O6—C231.220 (3)C18—H18C0.9800
O7—C251.447 (3)C19—H191.0000
O7—H70.8400C20—C211.532 (4)
O8—C311.425 (3)C20—C221.544 (4)
O8—C351.434 (3)C20—H201.0000
O9—C321.427 (3)C21—H21A0.9800
O9—H90.8400C21—H21B0.9800
O10—C331.436 (3)C21—H21C0.9800
O10—H100.8400C22—C231.510 (4)
O11—C341.424 (3)C22—H22A0.9900
O11—H110.8400C22—H22B0.9900
C1—C101.502 (4)C23—C241.508 (4)
C1—C21.525 (4)C24—C251.530 (4)
C1—H1A0.9900C24—H24A0.9900
C1—H1B0.9900C24—H24B0.9900
C2—C31.517 (4)C25—C271.521 (5)
C2—H2A0.9900C25—C261.522 (5)
C2—H2B0.9900C26—H26A0.9800
C3—C41.542 (4)C26—H26B0.9800
C3—H31.0000C26—H26C0.9800
C4—C51.512 (4)C27—H27A0.9800
C4—C301.535 (4)C27—H27B0.9800
C4—C291.541 (4)C27—H27C0.9800
C5—C101.330 (4)C28—H28A0.9800
C5—C61.508 (4)C28—H28B0.9800
C6—C71.552 (4)C28—H28C0.9800
C6—H61.0000C29—H29A0.9800
C7—C81.537 (4)C29—H29B0.9800
C7—H7A0.9900C29—H29C0.9800
C7—H7B0.9900C30—H30A0.9800
C8—C91.522 (4)C30—H30B0.9800
C8—C141.539 (4)C30—H30C0.9800
C8—H81.0000C31—C321.525 (4)
C9—C111.336 (4)C31—H311.0000
C9—C191.517 (4)C32—C331.526 (4)
C10—C191.503 (4)C32—H321.0000
C11—C121.512 (4)C33—C341.526 (4)
C11—H11A0.9500C33—H331.0000
C12—C131.525 (4)C34—C351.509 (4)
C12—H12A0.9900C34—H341.0000
C12—H12B0.9900C35—H35A0.9900
C13—C181.541 (4)C35—H35B0.9900
C13—C171.566 (4)O1W—H1W0.87 (3)
C13—C141.580 (4)O1W—H2W0.97 (4)
C14—C151.534 (4)
C31—O1—C3114.6 (2)H18B—C18—H18C109.5
C6—O2—O3109.6 (2)O3—C19—C10114.3 (2)
C19—O3—O2113.29 (19)O3—C19—C9109.5 (2)
C15—O4—H4109.5C10—C19—C9109.2 (2)
C25—O7—H7109.5O3—C19—H19107.9
C31—O8—C35111.1 (2)C10—C19—H19107.9
C32—O9—H9109.5C9—C19—H19107.9
C33—O10—H10109.5C21—C20—C17110.8 (2)
C34—O11—H11109.5C21—C20—C22107.9 (2)
C10—C1—C2111.7 (2)C17—C20—C22111.2 (2)
C10—C1—H1A109.3C21—C20—H20109.0
C2—C1—H1A109.3C17—C20—H20109.0
C10—C1—H1B109.3C22—C20—H20109.0
C2—C1—H1B109.3C20—C21—H21A109.5
H1A—C1—H1B107.9C20—C21—H21B109.5
C3—C2—C1110.9 (2)H21A—C21—H21B109.5
C3—C2—H2A109.5C20—C21—H21C109.5
C1—C2—H2A109.5H21A—C21—H21C109.5
C3—C2—H2B109.5H21B—C21—H21C109.5
C1—C2—H2B109.5C23—C22—C20118.2 (2)
H2A—C2—H2B108.1C23—C22—H22A107.8
O1—C3—C2108.4 (2)C20—C22—H22A107.8
O1—C3—C4108.0 (2)C23—C22—H22B107.8
C2—C3—C4112.2 (2)C20—C22—H22B107.8
O1—C3—H3109.4H22A—C22—H22B107.1
C2—C3—H3109.4O6—C23—C24122.4 (3)
C4—C3—H3109.4O6—C23—C22121.7 (3)
C5—C4—C30111.8 (2)C24—C23—C22115.8 (3)
C5—C4—C29110.7 (2)C23—C24—C25117.3 (3)
C30—C4—C29108.2 (2)C23—C24—H24A108.0
C5—C4—C3108.4 (2)C25—C24—H24A108.0
C30—C4—C3108.5 (2)C23—C24—H24B108.0
C29—C4—C3109.3 (2)C25—C24—H24B108.0
C10—C5—C6114.2 (2)H24A—C24—H24B107.2
C10—C5—C4124.4 (3)O7—C25—C27104.6 (3)
C6—C5—C4121.4 (3)O7—C25—C26109.7 (2)
O2—C6—C5108.2 (2)C27—C25—C26111.2 (3)
O2—C6—C7111.6 (2)O7—C25—C24110.2 (2)
C5—C6—C7113.6 (3)C27—C25—C24110.2 (3)
O2—C6—H6107.7C26—C25—C24110.8 (3)
C5—C6—H6107.7C25—C26—H26A109.5
C7—C6—H6107.7C25—C26—H26B109.5
C8—C7—C6115.6 (2)H26A—C26—H26B109.5
C8—C7—H7A108.4C25—C26—H26C109.5
C6—C7—H7A108.4H26A—C26—H26C109.5
C8—C7—H7B108.4H26B—C26—H26C109.5
C6—C7—H7B108.4C25—C27—H27A109.5
H7A—C7—H7B107.4C25—C27—H27B109.5
C9—C8—C7113.5 (2)H27A—C27—H27B109.5
C9—C8—C14109.7 (2)C25—C27—H27C109.5
C7—C8—C14113.9 (2)H27A—C27—H27C109.5
C9—C8—H8106.4H27B—C27—H27C109.5
C7—C8—H8106.4C14—C28—H28A109.5
C14—C8—H8106.4C14—C28—H28B109.5
C11—C9—C19120.9 (3)H28A—C28—H28B109.5
C11—C9—C8122.6 (3)C14—C28—H28C109.5
C19—C9—C8116.4 (3)H28A—C28—H28C109.5
C5—C10—C1124.2 (3)H28B—C28—H28C109.5
C5—C10—C19116.4 (3)C4—C29—H29A109.5
C1—C10—C19118.7 (3)C4—C29—H29B109.5
C9—C11—C12125.3 (3)H29A—C29—H29B109.5
C9—C11—H11A117.3C4—C29—H29C109.5
C12—C11—H11A117.3H29A—C29—H29C109.5
C11—C12—C13110.7 (2)H29B—C29—H29C109.5
C11—C12—H12A109.5C4—C30—H30A109.5
C13—C12—H12A109.5C4—C30—H30B109.5
C11—C12—H12B109.5H30A—C30—H30B109.5
C13—C12—H12B109.5C4—C30—H30C109.5
H12A—C12—H12B108.1H30A—C30—H30C109.5
C12—C13—C18108.0 (2)H30B—C30—H30C109.5
C12—C13—C17116.5 (2)O1—C31—O8107.7 (2)
C18—C13—C17110.0 (2)O1—C31—C32108.9 (2)
C12—C13—C14108.1 (2)O8—C31—C32111.0 (2)
C18—C13—C14112.0 (2)O1—C31—H31109.7
C17—C13—C14102.2 (2)O8—C31—H31109.7
C15—C14—C8116.3 (2)C32—C31—H31109.7
C15—C14—C28108.0 (2)O9—C32—C31106.5 (2)
C8—C14—C28109.9 (2)O9—C32—C33111.4 (2)
C15—C14—C13100.8 (2)C31—C32—C33110.2 (2)
C8—C14—C13109.9 (2)O9—C32—H32109.6
C28—C14—C13111.8 (2)C31—C32—H32109.6
O4—C15—C16112.5 (2)C33—C32—H32109.6
O4—C15—C14116.5 (2)O10—C33—C32111.7 (2)
C16—C15—C14101.1 (2)O10—C33—C34110.4 (2)
O4—C15—H15108.8C32—C33—C34111.2 (2)
C16—C15—H15108.8O10—C33—H33107.8
C14—C15—H15108.8C32—C33—H33107.8
O5—C16—C15124.1 (3)C34—C33—H33107.8
O5—C16—C17125.0 (3)O11—C34—C35109.3 (2)
C15—C16—C17110.6 (3)O11—C34—C33109.2 (2)
C16—C17—C20114.3 (2)C35—C34—C33109.6 (3)
C16—C17—C13102.3 (2)O11—C34—H34109.6
C20—C17—C13120.8 (2)C35—C34—H34109.6
C16—C17—H17106.1C33—C34—H34109.6
C20—C17—H17106.1O8—C35—C34110.0 (2)
C13—C17—H17106.1O8—C35—H35A109.7
C13—C18—H18A109.5C34—C35—H35A109.7
C13—C18—H18B109.5O8—C35—H35B109.7
H18A—C18—H18B109.5C34—C35—H35B109.7
C13—C18—H18C109.5H35A—C35—H35B108.2
H18A—C18—H18C109.5H1W—O1W—H2W104 (3)
C6—O2—O3—C1930.4 (3)C13—C14—C15—O4166.6 (2)
C10—C1—C2—C341.2 (3)C8—C14—C15—C16163.0 (2)
C31—O1—C3—C2102.6 (3)C28—C14—C15—C1673.1 (3)
C31—O1—C3—C4135.6 (2)C13—C14—C15—C1644.3 (3)
C1—C2—C3—O156.7 (3)O4—C15—C16—O522.2 (4)
C1—C2—C3—C462.5 (3)C14—C15—C16—O5147.2 (3)
O1—C3—C4—C571.2 (3)O4—C15—C16—C17152.2 (2)
C2—C3—C4—C548.3 (3)C14—C15—C16—C1727.2 (3)
O1—C3—C4—C3050.4 (3)O5—C16—C17—C2051.6 (4)
C2—C3—C4—C30169.9 (2)C15—C16—C17—C20134.1 (3)
O1—C3—C4—C29168.2 (2)O5—C16—C17—C13176.0 (3)
C2—C3—C4—C2972.4 (3)C15—C16—C17—C131.7 (3)
C30—C4—C5—C10137.0 (3)C12—C13—C17—C16146.8 (2)
C29—C4—C5—C10102.3 (3)C18—C13—C17—C1690.0 (3)
C3—C4—C5—C1017.5 (4)C14—C13—C17—C1629.2 (3)
C30—C4—C5—C641.1 (4)C12—C13—C17—C2084.9 (3)
C29—C4—C5—C679.6 (3)C18—C13—C17—C2038.4 (3)
C3—C4—C5—C6160.6 (3)C14—C13—C17—C20157.5 (2)
O3—O2—C6—C567.3 (3)O2—O3—C19—C1024.2 (3)
O3—O2—C6—C758.4 (3)O2—O3—C19—C998.6 (3)
C10—C5—C6—O247.1 (3)C5—C10—C19—O346.1 (3)
C4—C5—C6—O2134.6 (3)C1—C10—C19—O3142.8 (3)
C10—C5—C6—C777.4 (3)C5—C10—C19—C976.9 (3)
C4—C5—C6—C7100.9 (3)C1—C10—C19—C994.2 (3)
O2—C6—C7—C895.1 (3)C11—C9—C19—O3108.7 (3)
C5—C6—C7—C827.5 (4)C8—C9—C19—O374.5 (3)
C6—C7—C8—C951.3 (3)C11—C9—C19—C10125.5 (3)
C6—C7—C8—C14177.8 (2)C8—C9—C19—C1051.3 (3)
C7—C8—C9—C11146.9 (3)C16—C17—C20—C21178.8 (3)
C14—C8—C9—C1118.2 (4)C13—C17—C20—C2158.4 (3)
C7—C8—C9—C1936.3 (3)C16—C17—C20—C2258.8 (3)
C14—C8—C9—C19165.0 (2)C13—C17—C20—C22178.4 (2)
C6—C5—C10—C1179.2 (3)C21—C20—C22—C23153.2 (3)
C4—C5—C10—C10.9 (5)C17—C20—C22—C2385.1 (3)
C6—C5—C10—C198.7 (4)C20—C22—C23—O634.9 (4)
C4—C5—C10—C19169.6 (3)C20—C22—C23—C24148.8 (3)
C2—C1—C10—C510.9 (4)O6—C23—C24—C258.8 (4)
C2—C1—C10—C19178.8 (2)C22—C23—C24—C25167.5 (3)
C19—C9—C11—C12177.6 (3)C23—C24—C25—O755.8 (4)
C8—C9—C11—C121.0 (5)C23—C24—C25—C27170.7 (3)
C9—C11—C12—C1316.7 (4)C23—C24—C25—C2665.8 (3)
C11—C12—C13—C1874.0 (3)C3—O1—C31—O869.4 (3)
C11—C12—C13—C17161.7 (2)C3—O1—C31—C32170.2 (2)
C11—C12—C13—C1447.4 (3)C35—O8—C31—O1178.4 (2)
C9—C8—C14—C15163.6 (2)C35—O8—C31—C3262.5 (3)
C7—C8—C14—C1568.0 (3)O1—C31—C32—O966.0 (3)
C9—C8—C14—C2873.5 (3)O8—C31—C32—O9175.5 (2)
C7—C8—C14—C2855.0 (3)O1—C31—C32—C33173.0 (2)
C9—C8—C14—C1350.0 (3)O8—C31—C32—C3354.6 (3)
C7—C8—C14—C13178.4 (2)O9—C32—C33—O1068.2 (3)
C12—C13—C14—C15169.9 (2)C31—C32—C33—O10173.8 (2)
C18—C13—C14—C1571.3 (3)O9—C32—C33—C34167.9 (2)
C17—C13—C14—C1546.4 (2)C31—C32—C33—C3449.9 (3)
C12—C13—C14—C866.9 (3)O10—C33—C34—O1157.0 (3)
C18—C13—C14—C851.9 (3)C32—C33—C34—O1167.6 (3)
C17—C13—C14—C8169.6 (2)O10—C33—C34—C35176.7 (2)
C12—C13—C14—C2855.4 (3)C32—C33—C34—C3552.1 (3)
C18—C13—C14—C28174.2 (2)C31—O8—C35—C3464.6 (3)
C17—C13—C14—C2868.0 (3)O11—C34—C35—O861.2 (3)
C8—C14—C15—O474.7 (3)C33—C34—C35—O858.5 (3)
C28—C14—C15—O449.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O11i0.841.992.762 (3)152
O7—H7···O60.842.222.838 (3)130
O9—H9···O10ii0.842.283.015 (3)146
O10—H10···O1W0.841.862.683 (3)165
O11—H11···O10iii0.841.862.679 (3)163
O1W—H2W···O5iv0.97 (4)1.92 (4)2.815 (3)153 (3)
O1W—H1W···O7iv0.87 (3)1.99 (3)2.847 (3)171 (3)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z+1; (iii) x1/2, y+1/2, z+1; (iv) x1, y, z.
 

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