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The crystal structure of a per­acetyl­ated glu­cosyl ester of kaurenic acid, (4α)-kaur-16-en-18-carbonyl 2,3,4,6-tetra-O-acetyl-α-D-gluco­pyran­oside, C34H48O11, is reported. The synchrotron X-ray diffraction experiment showed that the glu­cosyl moiety adopts an α-perpendicular orientation with respect to the plane of the kaurenic acid. This conformation would allow the sugar hydroxyl groups, one unprotected, to interact with solvent or with biological membranes, enhancing its in vitro activity against murine melanoma in mice.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002181/om6204sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002181/om6204Isup2.hkl
Contains datablock I

CCDC reference: 236062

Key indicators

  • Single-crystal synchrotron study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.046
  • wR factor = 0.125
  • Data-to-parameter ratio = 5.8

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_1_A Reflection count < 85% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 18.08 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 2336 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3056 Completeness (_total/calc) 76.44%
Author Response: ... The compound experienced a first order irreversible transition at temperatures under 173 K making the collection of data difficult during the time allocated at beam line ID11, ESRF. Data was collected from 1 to 19.5 degrees, but unreliable data were discarded using the SHELX command SHEL.

PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.76
Author Response: ... IDEM
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.08 Deg.
Author Response: ... IDEM
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.76
Author Response: ... IDEM

Alert level B REFNR01_ALERT_3_B Ratio of reflections to parameters is < 6 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5814 Proportion of unique data used 1.0000 Ratio reflections to parameters 5.7537 PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 5.75
Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5814 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 18.08 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.97 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.60 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C26 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C28 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C27
Alert level G ABSMU_01 Radiation type not identified. Calculation of _exptl_absorpt_correction_mu not performed. 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 18.08 From the CIF: _reflns_number_total 2336 Count of symmetry unique reflns 3056 Completeness (_total/calc) 76.44% 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
Author Response: ... The compound experienced a first order irreversible transition at temperatures under 173 K making the collection of data difficult during the time allocated at beam line ID11, ESRF. Data was collected from 1 to 19.5 degrees, but unreliable data were discarded using the SHELX command SHEL.


4 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 9 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Speck, 2000).

(4α)-Kaur-16-en-18-carbonyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside top
Crystal data top
C34H48O11F(000) = 680
Mr = 632.72Dx = 1.236 Mg m3
Monoclinic, P21Synchrotron radiation, λ = 0.53378 Å
Hall symbol: P 2ybCell parameters from 1024 reflections
a = 15.3738 (8) Åθ = 2.4–19.3°
b = 7.2254 (2) ŵ = 0.06 mm1
c = 15.9661 (9) ÅT = 173 K
β = 106.578 (2)°Needle, colourless
V = 1699.82 (14) Å30.15 × 0.03 × 0.03 mm
Z = 2
Data collection top
Bruker fixed kappa goniometer
diffractometer
2240 reflections with I > 2σ(I)
Radiation source: Beamline ID-11 ESRFRint = 0.057
Double crystal Si monochromatorθmax = 18.1°, θmin = 10.3°
Detector resolution: 0.70 pixels mm-1h = 1717
φ scan 0.1° intervalk = 78
8193 measured reflectionsl = 1818
2336 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0866P)2 + 0.2167P]
where P = (Fo2 + 2Fc2)/3
2336 reflections(Δ/σ)max < 0.001
406 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.18 e Å3
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
O10.15717 (15)0.4151 (4)0.34328 (18)0.0517 (7)
O20.11242 (14)0.1960 (4)0.24137 (13)0.0441 (6)
O30.00812 (17)0.4872 (4)0.14644 (14)0.0479 (6)
O40.0774 (3)0.4190 (8)0.0582 (4)0.1058 (18)
O50.18295 (15)0.3512 (4)0.05705 (13)0.0440 (6)
O60.2517 (4)0.5713 (10)0.1126 (2)0.127 (3)
O70.25293 (15)0.0944 (4)0.16372 (15)0.0480 (6)
O80.3051 (2)0.0004 (8)0.0244 (2)0.0836 (12)
O90.05559 (18)0.1936 (4)0.35920 (15)0.0506 (6)
O100.07349 (17)0.4984 (4)0.34740 (16)0.0509 (6)
O110.00857 (14)0.0371 (4)0.24671 (14)0.0428 (6)
C10.2917 (2)0.1345 (5)0.4280 (2)0.0472 (8)
H1A0.26590.22570.46050.057*
H1B0.35420.17460.43150.057*
C20.2348 (2)0.1359 (5)0.3317 (2)0.0495 (8)
H2A0.23880.25940.30630.059*
H2B0.17040.11250.32810.059*
C30.2675 (2)0.0103 (6)0.2796 (2)0.0457 (8)
H3A0.22710.01010.21900.055*
H3B0.32920.02320.27730.055*
C40.27010 (18)0.2062 (5)0.31713 (19)0.0388 (7)
C50.32695 (16)0.2014 (5)0.41536 (18)0.0354 (7)
H5A0.38810.15720.41380.042*
C60.34584 (19)0.3883 (5)0.4613 (2)0.0398 (7)
H6A0.36210.47990.42210.048*
H6B0.29070.43270.47520.048*
C70.4232 (2)0.3700 (6)0.5449 (2)0.0450 (8)
H7A0.47890.33260.52980.054*
H7B0.43480.49230.57380.054*
C80.40454 (18)0.2304 (5)0.60854 (19)0.0413 (8)
C90.37266 (18)0.0446 (5)0.5623 (2)0.0407 (7)
H9A0.42700.00320.54650.049*
C100.29612 (18)0.0547 (5)0.47248 (19)0.0373 (7)
C110.3563 (2)0.0994 (6)0.6279 (2)0.0525 (9)
H11A0.31620.19780.59460.063*
H11B0.41510.15750.65840.063*
C120.3135 (3)0.0230 (7)0.6971 (3)0.0594 (11)
H12A0.24760.00470.67030.071*
H12B0.32150.11420.74500.071*
C130.3565 (2)0.1602 (7)0.7346 (2)0.0565 (10)
H13A0.33300.20480.78330.068*
C140.3399 (2)0.3006 (6)0.6603 (2)0.0460 (8)
H14A0.35590.42750.68280.055*
H14B0.27580.29860.62390.055*
C150.4914 (2)0.2005 (7)0.6857 (2)0.0549 (9)
H15A0.52980.10270.67120.066*
H15B0.52710.31630.69890.066*
C160.4589 (3)0.1429 (8)0.7628 (3)0.0596 (10)
C170.5094 (3)0.0892 (10)0.8405 (3)0.0784 (15)
H17A0.57360.08380.85250.094*
H17B0.48160.05600.88440.094*
C180.17505 (19)0.2847 (5)0.30522 (19)0.0369 (7)
C190.3139 (2)0.3340 (6)0.2638 (2)0.0491 (8)
H19A0.27710.33430.20260.074*
H19B0.37510.28940.26760.074*
H19C0.31760.46000.28730.074*
C200.20100 (19)0.0949 (5)0.4832 (2)0.0424 (7)
H20A0.15630.09940.42550.064*
H20B0.20190.21410.51270.064*
H20C0.18450.00340.51810.064*
C210.02061 (19)0.2181 (5)0.23823 (18)0.0385 (7)
H21A0.01420.29820.28720.046*
C220.0330 (2)0.2975 (5)0.14946 (19)0.0401 (7)
H22A0.02000.22620.10070.048*
C230.1337 (2)0.2897 (5)0.14314 (17)0.0393 (7)
H23A0.14650.37480.18760.047*
C240.1613 (2)0.0933 (5)0.15930 (18)0.0401 (7)
H24A0.15500.00860.11180.048*
C250.10006 (19)0.0282 (5)0.24883 (18)0.0390 (7)
H25A0.10860.11210.29570.047*
C260.0503 (3)0.5329 (8)0.1005 (2)0.0584 (11)
C270.0771 (4)0.7266 (9)0.1124 (3)0.0729 (13)
H27A0.11940.75460.07840.109*
H27B0.10670.75040.17440.109*
H27C0.02310.80510.09240.109*
C280.2405 (3)0.4936 (8)0.0504 (2)0.0666 (13)
C290.2843 (5)0.5410 (12)0.0429 (3)0.101 (2)
H29A0.32490.64710.04620.151*
H29B0.31930.43470.07260.151*
H29C0.23750.57260.07120.151*
C300.3190 (2)0.0444 (7)0.0906 (3)0.0568 (10)
C310.4111 (3)0.0675 (10)0.1055 (3)0.0777 (15)
H31A0.45840.03210.05240.116*
H31B0.41950.19700.11960.116*
H31C0.41500.01180.15410.116*
C320.1155 (2)0.1676 (6)0.2710 (2)0.0460 (8)
H32A0.17970.18740.26940.055*
H32B0.09970.25430.22960.055*
C330.0371 (2)0.3666 (5)0.3866 (2)0.0415 (7)
C340.0355 (3)0.3722 (7)0.4725 (2)0.0580 (9)
H34A0.04720.50100.49170.087*
H34B0.01550.30230.51620.087*
H34C0.09130.31690.46560.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0391 (11)0.0441 (15)0.0674 (14)0.0033 (10)0.0078 (9)0.0113 (12)
O20.0344 (10)0.0580 (16)0.0405 (10)0.0010 (10)0.0116 (8)0.0094 (10)
O30.0511 (12)0.0528 (16)0.0426 (11)0.0035 (10)0.0179 (9)0.0057 (10)
O40.112 (3)0.119 (4)0.119 (3)0.055 (3)0.086 (3)0.042 (3)
O50.0469 (11)0.0556 (16)0.0292 (9)0.0080 (10)0.0104 (8)0.0044 (9)
O60.168 (4)0.173 (6)0.0466 (15)0.121 (5)0.042 (2)0.027 (2)
O70.0357 (10)0.0640 (17)0.0409 (10)0.0063 (10)0.0052 (8)0.0047 (10)
O80.0662 (17)0.116 (3)0.0536 (17)0.0047 (19)0.0072 (13)0.0135 (18)
O90.0675 (15)0.0424 (15)0.0347 (11)0.0016 (11)0.0029 (9)0.0018 (10)
O100.0547 (13)0.0492 (16)0.0517 (12)0.0019 (11)0.0198 (10)0.0001 (11)
O110.0372 (10)0.0433 (14)0.0457 (10)0.0026 (9)0.0082 (8)0.0024 (9)
C10.0415 (15)0.039 (2)0.0588 (18)0.0030 (13)0.0108 (13)0.0002 (15)
C20.0503 (16)0.0354 (19)0.0601 (18)0.0028 (14)0.0113 (14)0.0072 (15)
C30.0412 (14)0.049 (2)0.0495 (16)0.0017 (14)0.0174 (12)0.0094 (15)
C40.0336 (13)0.0436 (19)0.0425 (15)0.0031 (13)0.0162 (11)0.0038 (13)
C50.0261 (11)0.0400 (18)0.0433 (14)0.0000 (12)0.0152 (10)0.0024 (12)
C60.0379 (13)0.0412 (18)0.0432 (14)0.0054 (12)0.0163 (12)0.0002 (13)
C70.0355 (13)0.055 (2)0.0459 (15)0.0100 (13)0.0131 (11)0.0053 (15)
C80.0303 (13)0.053 (2)0.0424 (15)0.0038 (13)0.0139 (11)0.0012 (14)
C90.0306 (12)0.047 (2)0.0467 (15)0.0086 (12)0.0150 (12)0.0047 (13)
C100.0286 (12)0.0383 (18)0.0459 (14)0.0012 (11)0.0120 (11)0.0025 (13)
C110.0478 (16)0.050 (2)0.0583 (18)0.0073 (15)0.0129 (14)0.0125 (16)
C120.0509 (17)0.076 (3)0.0551 (18)0.0052 (18)0.0210 (14)0.023 (2)
C130.0468 (17)0.082 (3)0.0442 (15)0.0100 (18)0.0183 (13)0.0073 (18)
C140.0381 (14)0.060 (2)0.0435 (15)0.0070 (15)0.0175 (12)0.0020 (14)
C150.0358 (14)0.077 (3)0.0508 (17)0.0046 (17)0.0111 (12)0.0004 (18)
C160.0510 (18)0.078 (3)0.0486 (17)0.0103 (18)0.0128 (14)0.0032 (18)
C170.067 (2)0.108 (4)0.054 (2)0.018 (3)0.0065 (17)0.005 (2)
C180.0360 (14)0.0359 (19)0.0392 (14)0.0025 (12)0.0113 (11)0.0020 (12)
C190.0485 (16)0.056 (2)0.0484 (15)0.0080 (15)0.0224 (12)0.0018 (15)
C200.0323 (13)0.048 (2)0.0508 (15)0.0002 (12)0.0174 (11)0.0055 (14)
C210.0351 (13)0.0449 (19)0.0355 (13)0.0003 (13)0.0099 (10)0.0007 (12)
C220.0427 (14)0.0437 (19)0.0353 (13)0.0006 (13)0.0134 (11)0.0008 (12)
C230.0400 (14)0.051 (2)0.0263 (12)0.0009 (13)0.0078 (10)0.0013 (12)
C240.0361 (14)0.050 (2)0.0320 (13)0.0015 (13)0.0058 (10)0.0003 (12)
C250.0355 (13)0.048 (2)0.0322 (12)0.0030 (13)0.0069 (10)0.0002 (12)
C260.0554 (18)0.087 (3)0.0376 (15)0.023 (2)0.0206 (14)0.0106 (18)
C270.085 (3)0.080 (3)0.056 (2)0.032 (3)0.0235 (18)0.003 (2)
C280.071 (2)0.093 (3)0.0394 (17)0.035 (2)0.0226 (15)0.017 (2)
C290.123 (4)0.135 (6)0.0428 (19)0.076 (4)0.020 (2)0.025 (3)
C300.0434 (16)0.065 (3)0.050 (2)0.0050 (17)0.0055 (14)0.0090 (17)
C310.0421 (18)0.101 (4)0.079 (2)0.008 (2)0.0008 (17)0.020 (3)
C320.0444 (15)0.053 (2)0.0363 (14)0.0050 (14)0.0050 (11)0.0008 (14)
C330.0440 (15)0.044 (2)0.0404 (14)0.0038 (14)0.0182 (12)0.0015 (14)
C340.066 (2)0.057 (3)0.0451 (16)0.0044 (17)0.0067 (14)0.0118 (16)
Geometric parameters (Å, º) top
O1—C181.195 (4)C12—C131.523 (8)
O2—C181.348 (4)C12—H12A0.9900
O2—C211.407 (4)C12—H12B0.9900
O3—C261.353 (5)C13—C161.513 (5)
O3—C221.427 (5)C13—C141.527 (6)
O4—C261.211 (7)C13—H13A1.0000
O5—C281.341 (6)C14—H14A0.9900
O5—C231.437 (4)C14—H14B0.9900
O6—C281.194 (6)C15—C161.513 (5)
O7—C301.360 (5)C15—H15A0.9900
O7—C241.431 (4)C15—H15B0.9900
O8—C301.180 (6)C16—C171.321 (7)
O9—C331.328 (5)C17—H17A0.9500
O9—C321.459 (4)C17—H17B0.9500
O10—C331.189 (5)C19—H19A0.9800
O11—C211.402 (5)C19—H19B0.9800
O11—C251.418 (4)C19—H19C0.9800
C1—C101.533 (5)C20—H20A0.9800
C1—C21.536 (5)C20—H20B0.9800
C1—H1A0.9900C20—H20C0.9800
C1—H1B0.9900C21—C221.533 (4)
C2—C31.517 (6)C21—H21A1.0000
C2—H2A0.9900C22—C231.524 (4)
C2—H2B0.9900C22—H22A1.0000
C3—C41.533 (5)C23—C241.523 (5)
C3—H3A0.9900C23—H23A1.0000
C3—H3B0.9900C24—C251.544 (4)
C4—C181.528 (4)C24—H24A1.0000
C4—C191.536 (5)C25—C321.494 (6)
C4—C51.563 (4)C25—H25A1.0000
C5—C61.524 (5)C26—C271.456 (8)
C5—C101.558 (4)C27—H27A0.9800
C5—H5A1.0000C27—H27B0.9800
C6—C71.520 (4)C27—H27C0.9800
C6—H6A0.9900C28—C291.489 (5)
C6—H6B0.9900C29—H29A0.9800
C7—C81.516 (5)C29—H29B0.9800
C7—H7A0.9900C29—H29C0.9800
C7—H7B0.9900C30—C311.510 (7)
C8—C91.543 (5)C31—H31A0.9800
C8—C141.548 (4)C31—H31B0.9800
C8—C151.552 (4)C31—H31C0.9800
C9—C111.547 (5)C32—H32A0.9900
C9—C101.576 (4)C32—H32B0.9900
C9—H9A1.0000C33—C341.501 (5)
C10—C201.547 (4)C34—H34A0.9800
C11—C121.541 (6)C34—H34B0.9800
C11—H11A0.9900C34—H34C0.9800
C11—H11B0.9900
C18—O2—C21117.8 (2)H15A—C15—H15B108.7
C26—O3—C22118.6 (3)C17—C16—C15127.1 (4)
C28—O5—C23117.9 (3)C17—C16—C13125.9 (4)
C30—O7—C24117.4 (3)C15—C16—C13107.0 (3)
C33—O9—C32117.2 (3)C16—C17—H17A120.0
C21—O11—C25113.0 (2)C16—C17—H17B120.0
C10—C1—C2114.0 (3)H17A—C17—H17B120.0
C10—C1—H1A108.8O1—C18—O2122.8 (3)
C2—C1—H1A108.8O1—C18—C4125.5 (3)
C10—C1—H1B108.8O2—C18—C4111.6 (3)
C2—C1—H1B108.8C4—C19—H19A109.5
H1A—C1—H1B107.6C4—C19—H19B109.5
C3—C2—C1111.1 (3)H19A—C19—H19B109.5
C3—C2—H2A109.4C4—C19—H19C109.5
C1—C2—H2A109.4H19A—C19—H19C109.5
C3—C2—H2B109.4H19B—C19—H19C109.5
C1—C2—H2B109.4C10—C20—H20A109.5
H2A—C2—H2B108.0C10—C20—H20B109.5
C2—C3—C4113.8 (3)H20A—C20—H20B109.5
C2—C3—H3A108.8C10—C20—H20C109.5
C4—C3—H3A108.8H20A—C20—H20C109.5
C2—C3—H3B108.8H20B—C20—H20C109.5
C4—C3—H3B108.8O11—C21—O2103.7 (3)
H3A—C3—H3B107.7O11—C21—C22109.6 (3)
C18—C4—C3112.2 (3)O2—C21—C22110.1 (2)
C18—C4—C19105.2 (3)O11—C21—H21A111.1
C3—C4—C19107.8 (2)O2—C21—H21A111.1
C18—C4—C5112.0 (2)C22—C21—H21A111.1
C3—C4—C5108.4 (3)O3—C22—C23108.1 (3)
C19—C4—C5111.2 (2)O3—C22—C21108.2 (3)
C6—C5—C10111.7 (2)C23—C22—C21108.4 (2)
C6—C5—C4116.0 (3)O3—C22—H22A110.7
C10—C5—C4115.2 (2)C23—C22—H22A110.7
C6—C5—H5A104.1C21—C22—H22A110.7
C10—C5—H5A104.1O5—C23—C24110.7 (3)
C4—C5—H5A104.1O5—C23—C22107.4 (2)
C7—C6—C5109.8 (3)C24—C23—C22110.5 (3)
C7—C6—H6A109.7O5—C23—H23A109.4
C5—C6—H6A109.7C24—C23—H23A109.4
C7—C6—H6B109.7C22—C23—H23A109.4
C5—C6—H6B109.7O7—C24—C23109.2 (3)
H6A—C6—H6B108.2O7—C24—C25107.7 (2)
C8—C7—C6113.3 (2)C23—C24—C25108.4 (2)
C8—C7—H7A108.9O7—C24—H24A110.5
C6—C7—H7A108.9C23—C24—H24A110.5
C8—C7—H7B108.9C25—C24—H24A110.5
C6—C7—H7B108.9O11—C25—C32105.9 (3)
H7A—C7—H7B107.7O11—C25—C24108.1 (2)
C7—C8—C9110.7 (3)C32—C25—C24114.3 (3)
C7—C8—C14114.4 (3)O11—C25—H25A109.5
C9—C8—C14112.1 (3)C32—C25—H25A109.5
C7—C8—C15109.9 (3)C24—C25—H25A109.5
C9—C8—C15110.0 (3)O4—C26—O3121.6 (5)
C14—C8—C1599.2 (2)O4—C26—C27126.7 (4)
C8—C9—C11110.6 (3)O3—C26—C27111.7 (4)
C8—C9—C10116.6 (3)C26—C27—H27A109.5
C11—C9—C10115.0 (3)C26—C27—H27B109.5
C8—C9—H9A104.3H27A—C27—H27B109.5
C11—C9—H9A104.3C26—C27—H27C109.5
C10—C9—H9A104.3H27A—C27—H27C109.5
C1—C10—C20107.5 (3)H27B—C27—H27C109.5
C1—C10—C5108.4 (2)O6—C28—O5122.9 (3)
C20—C10—C5113.1 (3)O6—C28—C29126.3 (4)
C1—C10—C9107.7 (3)O5—C28—C29110.8 (4)
C20—C10—C9113.1 (2)C28—C29—H29A109.5
C5—C10—C9106.9 (2)C28—C29—H29B109.5
C12—C11—C9115.5 (4)H29A—C29—H29B109.5
C12—C11—H11A108.4C28—C29—H29C109.5
C9—C11—H11A108.4H29A—C29—H29C109.5
C12—C11—H11B108.4H29B—C29—H29C109.5
C9—C11—H11B108.4O8—C30—O7124.0 (4)
H11A—C11—H11B107.5O8—C30—C31126.0 (3)
C13—C12—C11111.5 (3)O7—C30—C31109.8 (4)
C13—C12—H12A109.3C30—C31—H31A109.5
C11—C12—H12A109.3C30—C31—H31B109.5
C13—C12—H12B109.3H31A—C31—H31B109.5
C11—C12—H12B109.3C30—C31—H31C109.5
H12A—C12—H12B108.0H31A—C31—H31C109.5
C16—C13—C12110.1 (4)H31B—C31—H31C109.5
C16—C13—C14102.4 (3)O9—C32—C25104.6 (3)
C12—C13—C14108.3 (3)O9—C32—H32A110.8
C16—C13—H13A111.9C25—C32—H32A110.8
C12—C13—H13A111.9O9—C32—H32B110.8
C14—C13—H13A111.9C25—C32—H32B110.8
C13—C14—C8101.9 (3)H32A—C32—H32B108.9
C13—C14—H14A111.4O10—C33—O9123.8 (3)
C8—C14—H14A111.4O10—C33—C34125.1 (3)
C13—C14—H14B111.4O9—C33—C34111.1 (3)
C8—C14—H14B111.4C33—C34—H34A109.5
H14A—C14—H14B109.3C33—C34—H34B109.5
C16—C15—C8106.0 (3)H34A—C34—H34B109.5
C16—C15—H15A110.5C33—C34—H34C109.5
C8—C15—H15A110.5H34A—C34—H34C109.5
C16—C15—H15B110.5H34B—C34—H34C109.5
C8—C15—H15B110.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···O6i1.002.543.348 (5)138
C21—H21A···O10ii1.002.383.281 (4)150
C27—H27C···O4iii0.982.593.361 (8)135
Symmetry codes: (i) x, y1/2, z+1; (ii) x, y+1, z; (iii) x, y+1/2, z.
 

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