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In the title compound, C26H38O10, the acafarnane skeleton consists of three cis-fused rings, of which the five-membered ring is in an envelope conformation and the two six-membered rings adopt twist-boat and chair conformations. The lactone ring is in an envelope conformation. The D-glucose, in the β position with respect to the acafarnane skeleton, adopts a chair conformation. The mol­ecular structure and the crystal packing are stabilized by O—H...O inter­actions including a bifurcated hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031722/bt2140sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031722/bt2140Isup2.hkl
Contains datablock I

CCDC reference: 620674

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.085
  • Data-to-parameter ratio = 6.8

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.71 Ratio
Author Response: Due to poor quality of the crystal, data collected was not sufficient. Therefore the hydrogen positions could not be found precisely.

Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.75 PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.56 Ratio PLAT245_ALERT_2_C U(iso) H22 Smaller than U(eq) C22 by ... 0.01 AngSq PLAT410_ALERT_2_C Short Intra H...H Contact H5 .. H14A .. 1.96 Ang.
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 70.08 From the CIF: _reflns_number_total 2483 Count of symmetry unique reflns 2486 Completeness (_total/calc) 99.88% 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 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C22 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C24 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25 = . S
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 18 ALERT level G = General alerts; check 17 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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

Computing details top

Data collection: AED Software (Belletti et al., 1993); cell refinement: AED Software; data reduction: AED Software; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(1S,3aR,5aR,6S,6aR,7S,9R,11aS,11bR,11cS)-7- (beta-D-glucopyranosyloxy)dodecahydro-1,6- dihydroxy-3a,11b-dimethyl-8-methylene-1H- 6a,9-Methanocyclohept[2,3]indeno[4,5-c] furan-3(3aH)-one top
Crystal data top
C26H38O10F(000) = 548
Mr = 510.56Dx = 1.384 Mg m3
Monoclinic, P21Melting point: 110-112/% K
Hall symbol: P 2ybCu Kα radiation, λ = 1.54178 Å
a = 11.691 (2) ÅCell parameters from 44 reflections
b = 9.336 (3) Åθ = 11.4–20.1°
c = 12.370 (2) ŵ = 0.88 mm1
β = 114.82 (3)°T = 293 K
V = 1225.4 (6) Å3Prism, pale yellow
Z = 20.21 × 0.16 × 0.13 mm
Data collection top
Siemens AED
diffractometer
Rint = 0.038
Radiation source: fine-focus sealed tubeθmax = 70.1°, θmin = 3.9°
Graphite monochromatorh = 1411
θ – 2θ scansk = 511
2585 measured reflectionsl = 1415
2483 independent reflections1 standard reflections every 100 reflections
2446 reflections with I > 2σ(I) intensity decay: none
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)] = 0.030H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0669P)2 + 0.1111P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.004
2511 reflectionsΔρmax = 0.21 e Å3
372 parametersΔρmin = 0.17 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0058 (7)
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
C10.84069 (19)0.3137 (2)0.04432 (17)0.0307 (4)
C20.8089 (2)0.4429 (3)0.1017 (2)0.0452 (6)
C30.9290 (2)0.5194 (3)0.1817 (2)0.0449 (6)
C41.0024 (2)0.4252 (2)0.29099 (18)0.0335 (4)
C50.99885 (17)0.2623 (2)0.26492 (16)0.0256 (4)
C61.13382 (18)0.2133 (3)0.34700 (18)0.0327 (4)
C70.72650 (18)0.2144 (2)0.02009 (16)0.0286 (4)
C80.75578 (16)0.0788 (2)0.05580 (15)0.0238 (4)
C90.90080 (17)0.0645 (2)0.10313 (15)0.0241 (4)
C100.95464 (17)0.2194 (2)0.13098 (15)0.0246 (4)
C110.95394 (18)0.0563 (2)0.19622 (17)0.0309 (4)
C120.8875 (2)0.0747 (2)0.27903 (17)0.0346 (4)
C130.74353 (19)0.0568 (3)0.21344 (17)0.0327 (4)
C140.71415 (18)0.0930 (2)0.15894 (17)0.0293 (4)
C150.69608 (17)0.0667 (2)0.00044 (15)0.0251 (4)
C160.68443 (18)0.1478 (2)0.10209 (17)0.0299 (4)
C170.6225 (2)0.2691 (3)0.0914 (2)0.0412 (5)
C181.1411 (2)0.4599 (3)0.3412 (2)0.0418 (5)
C190.9584 (3)0.4550 (4)0.3893 (2)0.0546 (6)
C201.0647 (2)0.2346 (3)0.09394 (18)0.0368 (5)
C210.56711 (18)0.1102 (2)0.20594 (16)0.0263 (4)
C220.54675 (18)0.3324 (2)0.30547 (17)0.0280 (4)
C230.42753 (18)0.2829 (2)0.41210 (17)0.0293 (4)
C240.43031 (18)0.1204 (2)0.42344 (17)0.0277 (4)
C250.45274 (18)0.0452 (2)0.30748 (17)0.0285 (4)
C260.5528 (2)0.4942 (2)0.2830 (2)0.0365 (5)
O11.21256 (14)0.3422 (2)0.36876 (15)0.0427 (4)
O21.14018 (15)0.1622 (2)0.45396 (13)0.0437 (4)
O31.1867 (2)0.5792 (3)0.3562 (2)0.0725 (7)
O40.71632 (16)0.19158 (19)0.13861 (12)0.0406 (4)
O50.57420 (12)0.04957 (16)0.10035 (11)0.0282 (3)
O60.55316 (14)0.26130 (16)0.20032 (12)0.0315 (3)
O70.67420 (15)0.54557 (19)0.26418 (14)0.0400 (3)
O80.42630 (14)0.34697 (18)0.51700 (13)0.0391 (4)
O90.31556 (14)0.0664 (2)0.51304 (12)0.0397 (4)
O100.47394 (17)0.10494 (17)0.31335 (13)0.0392 (4)
H10.86520.35110.01690.048 (8)*
H2A0.75480.50790.04030.063 (10)*
H2B0.76400.41190.14800.055 (9)*
H3A0.90870.61060.20710.097 (14)*
H3B0.98010.53780.13850.051 (8)*
H50.94110.21760.29380.027 (6)*
H61.16230.13990.30730.032 (6)*
H70.64950.25930.02310.035 (6)*
H90.91590.03330.03460.025 (5)*
H11A0.94830.14590.15460.039 (7)*
H11B1.04250.03740.24450.038 (7)*
H12A0.92030.00450.34260.037 (7)*
H12B0.90630.16910.31490.035 (6)*
H130.70270.07350.26720.040 (7)*
H14A0.76250.16580.21570.025 (5)*
H14B0.62510.11500.12940.044 (7)*
H150.75330.11830.02630.019 (5)*
H17A0.61190.30630.15640.074 (11)*
H17B0.58950.31740.01900.044 (7)*
H19A0.86900.44070.35860.075 (10)*
H19B0.97830.55210.41620.092 (13)*
H19C1.00040.39080.45480.082 (12)*
H20A1.12500.15980.13040.046 (8)*
H20B1.10450.32610.11950.048 (8)*
H20C1.03310.22750.00890.048 (8)*
H210.64380.08830.21650.022 (5)*
H220.62040.30430.31920.017 (5)*
H230.35250.31190.40120.033 (6)*
H240.49920.09540.44530.023 (5)*
H250.37860.05860.29080.031 (6)*
H26A0.53680.51420.21370.044 (8)*
H26B0.48880.54230.35110.051 (8)*
H2O1.19930.10620.48270.061 (10)*
H4O0.65000.15020.17830.054 (9)*
H7O0.69170.61580.22040.073 (11)*
H8O0.35380.36870.56190.054 (9)*
H9O0.31550.07800.57880.052 (8)*
H10O0.49140.12100.36980.054 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0379 (9)0.0206 (9)0.0254 (9)0.0029 (8)0.0053 (8)0.0015 (8)
C20.0470 (12)0.0224 (10)0.0439 (11)0.0074 (10)0.0031 (10)0.0034 (10)
C30.0550 (14)0.0199 (10)0.0410 (11)0.0005 (10)0.0018 (10)0.0039 (10)
C40.0382 (10)0.0268 (10)0.0296 (9)0.0021 (9)0.0085 (8)0.0054 (8)
C50.0269 (9)0.0262 (10)0.0228 (8)0.0016 (7)0.0097 (7)0.0010 (7)
C60.0305 (9)0.0339 (11)0.0301 (9)0.0008 (8)0.0091 (8)0.0016 (8)
C70.0319 (9)0.0227 (10)0.0248 (9)0.0011 (8)0.0055 (7)0.0018 (8)
C80.0266 (8)0.0206 (9)0.0224 (8)0.0009 (7)0.0085 (7)0.0008 (7)
C90.0278 (8)0.0210 (9)0.0229 (8)0.0002 (7)0.0100 (7)0.0022 (7)
C100.0296 (8)0.0203 (9)0.0226 (8)0.0018 (7)0.0096 (7)0.0004 (7)
C110.0326 (9)0.0208 (9)0.0332 (9)0.0032 (8)0.0077 (8)0.0017 (8)
C120.0443 (11)0.0270 (10)0.0240 (8)0.0015 (9)0.0060 (8)0.0049 (8)
C130.0412 (10)0.0331 (11)0.0255 (8)0.0042 (9)0.0155 (8)0.0027 (9)
C140.0287 (9)0.0312 (10)0.0276 (9)0.0006 (8)0.0116 (7)0.0037 (8)
C150.0274 (8)0.0228 (9)0.0222 (8)0.0026 (7)0.0075 (7)0.0013 (7)
C160.0317 (9)0.0269 (10)0.0289 (9)0.0024 (8)0.0106 (8)0.0030 (8)
C170.0424 (11)0.0362 (12)0.0410 (11)0.0096 (10)0.0136 (9)0.0058 (10)
C180.0422 (12)0.0345 (12)0.0370 (10)0.0087 (10)0.0052 (9)0.0067 (10)
C190.0702 (16)0.0498 (15)0.0472 (13)0.0053 (14)0.0279 (12)0.0157 (13)
C200.0409 (10)0.0404 (12)0.0338 (10)0.0098 (10)0.0204 (9)0.0048 (10)
C210.0304 (9)0.0218 (9)0.0260 (9)0.0051 (7)0.0112 (7)0.0030 (7)
C220.0311 (8)0.0210 (9)0.0307 (9)0.0035 (8)0.0119 (7)0.0027 (8)
C230.0290 (9)0.0266 (10)0.0308 (10)0.0036 (8)0.0110 (7)0.0071 (8)
C240.0283 (8)0.0266 (10)0.0240 (9)0.0024 (7)0.0070 (7)0.0009 (8)
C250.0334 (9)0.0229 (9)0.0280 (9)0.0006 (8)0.0116 (7)0.0031 (8)
C260.0425 (11)0.0236 (10)0.0427 (11)0.0029 (9)0.0172 (9)0.0014 (9)
O10.0305 (7)0.0411 (9)0.0481 (9)0.0068 (7)0.0081 (6)0.0039 (7)
O20.0432 (8)0.0516 (11)0.0287 (7)0.0082 (8)0.0077 (6)0.0100 (7)
O30.0576 (12)0.0420 (11)0.0850 (16)0.0213 (10)0.0024 (11)0.0066 (11)
O40.0567 (9)0.0328 (8)0.0232 (7)0.0135 (7)0.0079 (6)0.0010 (6)
O50.0277 (6)0.0301 (7)0.0234 (6)0.0016 (6)0.0072 (5)0.0053 (6)
O60.0417 (8)0.0218 (7)0.0276 (7)0.0032 (6)0.0114 (6)0.0012 (5)
O70.0464 (8)0.0283 (8)0.0431 (8)0.0072 (7)0.0168 (7)0.0111 (7)
O80.0401 (8)0.0377 (9)0.0339 (7)0.0006 (7)0.0102 (6)0.0127 (7)
O90.0384 (7)0.0438 (9)0.0267 (7)0.0114 (7)0.0037 (6)0.0017 (7)
O100.0594 (9)0.0230 (7)0.0315 (7)0.0019 (7)0.0154 (7)0.0029 (6)
Geometric parameters (Å, º) top
C1—C21.523 (3)C15—O51.451 (2)
C1—C71.544 (3)C15—C161.532 (3)
C1—C101.581 (3)C15—H150.9800
C1—H10.9800C16—C171.321 (3)
C2—C31.515 (3)C17—H17A0.9300
C2—H2A0.9700C17—H17B0.9300
C2—H2B0.9700C18—O31.214 (3)
C3—C41.537 (3)C18—O11.335 (3)
C3—H3A0.9700C19—H19A0.9600
C3—H3B0.9700C19—H19B0.9600
C4—C181.508 (3)C19—H19C0.9600
C4—C191.532 (3)C20—H20A0.9600
C4—C51.552 (3)C20—H20B0.9600
C5—C61.544 (3)C20—H20C0.9600
C5—C101.566 (2)C21—O51.394 (2)
C5—H50.9800C21—O61.425 (2)
C6—O21.379 (3)C21—C251.524 (3)
C6—O11.470 (3)C21—H210.9800
C6—H60.9800C22—O61.434 (2)
C7—O41.436 (2)C22—C261.532 (3)
C7—C81.527 (3)C22—C231.534 (3)
C7—H70.9800C22—H220.9800
C8—C91.550 (2)C23—O81.423 (2)
C8—C141.550 (2)C23—C241.525 (3)
C8—C151.552 (3)C23—H230.9800
C9—C111.544 (3)C24—O91.426 (2)
C9—C101.557 (3)C24—C251.518 (3)
C9—H90.9800C24—H240.9800
C10—C201.543 (3)C25—O101.431 (3)
C11—C121.533 (3)C25—H250.9800
C11—H11A0.9700C26—O71.422 (3)
C11—H11B0.9700C26—H26A0.9700
C12—C131.540 (3)C26—H26B0.9700
C12—H12A0.9700O2—H2O0.8200
C12—H12B0.9700O4—H4O0.8200
C13—C161.516 (3)O7—H7O0.8200
C13—C141.528 (3)O8—H8O0.8200
C13—H130.9800O9—H9O0.8200
C14—H14A0.9700O10—H10O0.8200
C14—H14B0.9700
C2—C1—C7112.88 (18)C13—C14—C8101.23 (15)
C2—C1—C10115.23 (16)C13—C14—H14A111.5
C7—C1—C10108.41 (16)C8—C14—H14A111.5
C2—C1—H1106.6C13—C14—H14B111.5
C7—C1—H1106.6C8—C14—H14B111.5
C10—C1—H1106.6H14A—C14—H14B109.3
C3—C2—C1109.7 (2)O5—C15—C16111.28 (15)
C3—C2—H2A109.7O5—C15—C8112.44 (16)
C1—C2—H2A109.7C16—C15—C8103.95 (14)
C3—C2—H2B109.7O5—C15—H15109.7
C1—C2—H2B109.7C16—C15—H15109.7
H2A—C2—H2B108.2C8—C15—H15109.7
C2—C3—C4109.1 (2)C17—C16—C13126.4 (2)
C2—C3—H3A109.9C17—C16—C15125.24 (19)
C4—C3—H3A109.9C13—C16—C15108.09 (17)
C2—C3—H3B109.9C16—C17—H17A120.0
C4—C3—H3B109.9C16—C17—H17B120.0
H3A—C3—H3B108.3H17A—C17—H17B120.0
C18—C4—C19107.19 (19)O3—C18—O1121.9 (2)
C18—C4—C3110.3 (2)O3—C18—C4125.9 (2)
C19—C4—C3110.2 (2)O1—C18—C4112.2 (2)
C18—C4—C5103.08 (18)C4—C19—H19A109.5
C19—C4—C5110.7 (2)C4—C19—H19B109.5
C3—C4—C5114.94 (17)H19A—C19—H19B109.5
C6—C5—C4102.87 (16)C4—C19—H19C109.5
C6—C5—C10114.34 (15)H19A—C19—H19C109.5
C4—C5—C10116.01 (16)H19B—C19—H19C109.5
C6—C5—H5107.7C10—C20—H20A109.5
C4—C5—H5107.7C10—C20—H20B109.5
C10—C5—H5107.7H20A—C20—H20B109.5
O2—C6—O1109.29 (17)C10—C20—H20C109.5
O2—C6—C5111.22 (16)H20A—C20—H20C109.5
O1—C6—C5105.45 (17)H20B—C20—H20C109.5
O2—C6—H6110.3O5—C21—O6108.62 (16)
O1—C6—H6110.3O5—C21—C25107.28 (15)
C5—C6—H6110.3O6—C21—C25110.82 (16)
O4—C7—C8113.96 (16)O5—C21—H21110.0
O4—C7—C1107.39 (16)O6—C21—H21110.0
C8—C7—C1104.98 (14)C25—C21—H21110.0
O4—C7—H7110.1O6—C22—C26108.12 (17)
C8—C7—H7110.1O6—C22—C23108.87 (16)
C1—C7—H7110.1C26—C22—C23114.12 (17)
C7—C8—C9103.34 (15)O6—C22—H22108.5
C7—C8—C14111.61 (16)C26—C22—H22108.5
C9—C8—C14111.60 (14)C23—C22—H22108.5
C7—C8—C15120.49 (14)O8—C23—C24109.05 (17)
C9—C8—C15108.01 (15)O8—C23—C22108.38 (16)
C14—C8—C15101.91 (15)C24—C23—C22109.37 (16)
C11—C9—C8112.23 (15)O8—C23—H23110.0
C11—C9—C10120.99 (15)C24—C23—H23110.0
C8—C9—C10106.29 (14)C22—C23—H23110.0
C11—C9—H9105.4O9—C24—C25107.68 (16)
C8—C9—H9105.4O9—C24—C23111.96 (17)
C10—C9—H9105.4C25—C24—C23112.04 (17)
C20—C10—C9109.26 (16)O9—C24—H24108.3
C20—C10—C5110.15 (15)C25—C24—H24108.3
C9—C10—C5113.25 (15)C23—C24—H24108.3
C20—C10—C1108.53 (16)O10—C25—C24111.74 (17)
C9—C10—C1102.68 (14)O10—C25—C21108.73 (16)
C5—C10—C1112.64 (15)C24—C25—C21109.77 (16)
C12—C11—C9114.97 (16)O10—C25—H25108.9
C12—C11—H11A108.5C24—C25—H25108.9
C9—C11—H11A108.5C21—C25—H25108.9
C12—C11—H11B108.5O7—C26—C22109.25 (18)
C9—C11—H11B108.5O7—C26—H26A109.8
H11A—C11—H11B107.5C22—C26—H26A109.8
C11—C12—C13112.59 (15)O7—C26—H26B109.8
C11—C12—H12A109.1C22—C26—H26B109.8
C13—C12—H12A109.1H26A—C26—H26B108.3
C11—C12—H12B109.1C18—O1—C6110.53 (16)
C13—C12—H12B109.1C6—O2—H2O109.5
H12A—C12—H12B107.8C7—O4—H4O109.5
C16—C13—C14100.35 (15)C21—O5—C15113.86 (15)
C16—C13—C12113.49 (18)C21—O6—C22112.16 (15)
C14—C13—C12108.97 (17)C26—O7—H7O109.5
C16—C13—H13111.2C23—O8—H8O109.5
C14—C13—H13111.2C24—O9—H9O109.5
C12—C13—H13111.2C25—O10—H10O109.5
C7—C1—C2—C3169.46 (19)C16—C13—C14—C847.65 (17)
C10—C1—C2—C344.2 (3)C12—C13—C14—C871.76 (18)
C1—C2—C3—C469.6 (3)C7—C8—C14—C13175.78 (14)
C2—C3—C4—C18154.2 (2)C9—C8—C14—C1369.15 (19)
C2—C3—C4—C1987.7 (3)C15—C8—C14—C1345.89 (17)
C2—C3—C4—C538.3 (3)C7—C8—C15—O529.2 (2)
C18—C4—C5—C621.6 (2)C9—C8—C15—O5147.43 (14)
C19—C4—C5—C692.7 (2)C14—C8—C15—O594.91 (16)
C3—C4—C5—C6141.6 (2)C7—C8—C15—C16149.68 (17)
C18—C4—C5—C10103.97 (19)C9—C8—C15—C1692.10 (16)
C19—C4—C5—C10141.67 (18)C14—C8—C15—C1625.56 (17)
C3—C4—C5—C1016.0 (3)C14—C13—C16—C17141.8 (2)
C4—C5—C6—O294.6 (2)C12—C13—C16—C17102.2 (2)
C10—C5—C6—O2138.72 (18)C14—C13—C16—C1532.10 (19)
C4—C5—C6—O123.74 (19)C12—C13—C16—C1584.0 (2)
C10—C5—C6—O1102.92 (18)O5—C15—C16—C1748.8 (3)
C2—C1—C7—O4128.29 (18)C8—C15—C16—C17170.1 (2)
C10—C1—C7—O4102.80 (17)O5—C15—C16—C13125.15 (18)
C2—C1—C7—C8110.08 (19)C8—C15—C16—C133.90 (19)
C10—C1—C7—C818.8 (2)C19—C4—C18—O375.8 (3)
O4—C7—C8—C982.76 (18)C3—C4—C18—O344.1 (4)
C1—C7—C8—C934.47 (18)C5—C4—C18—O3167.3 (3)
O4—C7—C8—C14157.19 (16)C19—C4—C18—O1104.2 (2)
C1—C7—C8—C1485.59 (18)C3—C4—C18—O1135.9 (2)
O4—C7—C8—C1537.8 (2)C5—C4—C18—O112.7 (2)
C1—C7—C8—C15155.01 (16)O6—C22—C23—O8176.33 (16)
C7—C8—C9—C11172.61 (15)C26—C22—C23—O862.8 (2)
C14—C8—C9—C1152.5 (2)O6—C22—C23—C2457.5 (2)
C15—C8—C9—C1158.69 (18)C26—C22—C23—C24178.42 (18)
C7—C8—C9—C1038.27 (17)O8—C23—C24—O968.0 (2)
C14—C8—C9—C1081.79 (18)C22—C23—C24—O9173.62 (14)
C15—C8—C9—C10166.98 (14)O8—C23—C24—C25170.89 (14)
C11—C9—C10—C2089.6 (2)C22—C23—C24—C2552.5 (2)
C8—C9—C10—C20140.97 (15)O9—C24—C25—O1065.1 (2)
C11—C9—C10—C533.6 (2)C23—C24—C25—O10171.32 (16)
C8—C9—C10—C595.85 (16)O9—C24—C25—C21174.15 (16)
C11—C9—C10—C1155.33 (16)C23—C24—C25—C2150.6 (2)
C8—C9—C10—C125.90 (18)O5—C21—C25—O1064.51 (19)
C6—C5—C10—C2038.6 (2)O6—C21—C25—O10177.06 (15)
C4—C5—C10—C2081.0 (2)O5—C21—C25—C24172.98 (15)
C6—C5—C10—C984.13 (19)O6—C21—C25—C2454.5 (2)
C4—C5—C10—C9156.35 (16)O6—C22—C26—O7105.27 (19)
C6—C5—C10—C1159.89 (16)C23—C22—C26—O7133.43 (18)
C4—C5—C10—C140.4 (2)O3—C18—O1—C6177.3 (3)
C2—C1—C10—C20112.4 (2)C4—C18—O1—C62.7 (3)
C7—C1—C10—C20120.01 (18)O2—C6—O1—C18102.4 (2)
C2—C1—C10—C9131.99 (19)C5—C6—O1—C1817.2 (2)
C7—C1—C10—C94.41 (19)O6—C21—O5—C1577.48 (19)
C2—C1—C10—C59.8 (2)C25—C21—O5—C15162.68 (15)
C7—C1—C10—C5117.74 (17)C16—C15—O5—C21120.89 (17)
C8—C9—C11—C1236.1 (2)C8—C15—O5—C21122.96 (16)
C10—C9—C11—C1290.7 (2)O5—C21—O6—C22179.25 (14)
C9—C11—C12—C1339.9 (3)C25—C21—O6—C2263.1 (2)
C11—C12—C13—C1651.1 (2)C26—C22—O6—C21171.24 (16)
C11—C12—C13—C1459.8 (2)C23—C22—O6—C2164.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O50.822.432.952 (2)122
O4—H4O···O100.822.082.866 (3)161
O2—H2O···O9i0.822.092.868 (3)157
O8—H8O···O3ii0.821.852.664 (3)172
O9—H9O···O7iii0.822.022.815 (2)164
O10—H10O···O8iii0.822.032.832 (2)168
O7—H7O···O4iv0.822.022.835 (2)170
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y1, z1; (iii) x+1, y+1/2, z1; (iv) x, y1, z.
Ring-puckering parameters (Å, °) for five rings top
Ringq2q3QTθ
A(C1-C2-C3-C4-C5-C10)0.672 (2)-0.133 (2)0.685 (2)101.2 (2)
B(C1-C7-C8-C9-C10)0.372 (2)
C(C8-C9-C11-C12-C13-C14)0.260 (2)-0.570 (2)0.627 (2)155.5 (2)
D(C4-C5-C6-O1-C18)0.242 (2)
E(C21-O6-C22-C23-C24-C25)0.056 (2)-0.572 (2)0.574 (2)174.4 (2)
 

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