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The title compound, epoxy­azadiradione or 17-(3-fur­yl)-4,4,10,13-tetra­methyl-3,16-dioxo-3,4,5,6,7,8,9,10,11,12,13,15,-16,17-tetra­deca­hydro-20-oxacyclo­propa[14,15]cyclo­penta­[a]phen­athren-7-yl acetate, C28H34O6, was isolated from the fruit of Aza­dirachta indica (neem) and found to have anti­feedant activity. The three fused six-membered rings adopt half-chair, chair and boat conformations, with the cyclopentane ring in an envelope conformation. In the crystal structure, C—H...O hydrogen bonds generate an R21(7) ring motif and link the mol­ecules into chains along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016923/sj2261sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016923/sj2261Isup2.hkl
Contains datablock I

CCDC reference: 647333

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.052
  • wR factor = 0.152
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT412_ALERT_2_B Short Intra XH3 .. XHn H9 .. H18A .. 1.77 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.50 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O21B PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H19A .. H30C .. 1.83 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H19B .. H28C .. 1.87 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 27.98 From the CIF: _reflns_number_total 3064 Count of symmetry unique reflns 3138 Completeness (_total/calc) 97.64% 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 C5 = . 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 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 12 ALERT level G = General alerts; check 12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 1999); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST97 (Nardelli, 1995).

17-(3-furyl)-4,4,10,13-tetramethyl-3,16-dioxo- 3,4,5,6,7,8,9,10,11,12,13,15,16,17-tetradecahydro-20- oxacyclopropa[14,15]cyclopenta[a]phenathren-7-yl acetate top
Crystal data top
C28H34O6F(000) = 500
Mr = 466.55Dx = 1.243 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2500 reflections
a = 9.6532 (7) Åθ = 2.0–28.0°
b = 12.6550 (9) ŵ = 0.09 mm1
c = 10.5710 (8) ÅT = 293 K
β = 105.096 (1)°Needle, colourless
V = 1246.80 (16) Å30.25 × 0.18 × 0.10 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3064 independent reflections
Radiation source: fine-focus sealed tube2854 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.979, Tmax = 0.991k = 1616
14353 measured reflectionsl = 1313
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.1098P)2 + 0.0395P]
where P = (Fo2 + 2Fc2)/3
3064 reflections(Δ/σ)max = 0.003
336 parametersΔρmax = 0.23 e Å3
66 restraintsΔρmin = 0.16 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*/UeqOcc. (<1)
C10.0095 (3)1.0245 (2)0.8774 (2)0.0546 (5)
H10.00860.95260.88200.066*
C20.0044 (3)1.0855 (2)0.9784 (3)0.0582 (5)
H20.01401.05371.05160.070*
C30.0260 (3)1.1997 (2)0.9806 (3)0.0593 (6)
C40.0819 (2)1.2524 (2)0.8739 (2)0.0529 (5)
C50.1412 (2)1.16530 (17)0.79850 (19)0.0443 (4)
H50.22451.13720.86380.053*
C60.2044 (3)1.2068 (2)0.6891 (2)0.0547 (5)
H6A0.12721.22610.61370.066*
H6B0.26101.26960.71920.066*
C70.2984 (3)1.1233 (2)0.6494 (2)0.0519 (5)
H70.33801.15060.57940.062*
C80.2163 (2)1.02059 (19)0.60536 (19)0.0472 (4)
C90.1396 (2)0.98271 (17)0.71039 (19)0.0426 (4)
H90.21790.96930.78880.051*
C100.0438 (2)1.06713 (17)0.7549 (2)0.0448 (4)
C110.0720 (3)0.8732 (2)0.6713 (2)0.0557 (5)
H11A0.01490.85380.73090.067*
H11B0.00820.87730.58380.067*
C120.1837 (3)0.7874 (2)0.6740 (4)0.0725 (8)
H12A0.15040.74250.59770.087*
H12B0.19160.74380.75110.087*
C130.3331 (3)0.8298 (2)0.6757 (2)0.0524 (5)
C140.3152 (2)0.9287 (2)0.58797 (18)0.0501 (5)
C150.4365 (4)0.9318 (3)0.5260 (3)0.0753 (8)
H150.47930.99850.50800.090*
C160.5250 (3)0.8357 (3)0.5710 (3)0.0758 (8)
C170.4262 (3)0.7559 (3)0.6104 (2)0.0638 (6)
H170.36220.72880.52920.077*
C180.4269 (4)0.8522 (2)0.8153 (2)0.0674 (7)
H18A0.37510.89650.86080.101*
H18B0.51350.88720.81010.101*
H18C0.45060.78670.86180.101*
C190.1016 (3)1.0866 (3)0.6536 (3)0.0647 (6)
H19A0.08491.11330.57390.097*
H19B0.15641.13720.68810.097*
H19C0.15391.02130.63610.097*
C200.4949 (5)0.6623 (3)0.6877 (3)0.0838 (10)
C220.4219 (7)0.5709 (4)0.7098 (5)0.1032 (13)
H220.32560.55210.68350.124*
C21A0.6411 (14)0.657 (2)0.740 (2)0.098 (4)0.50 (4)
H21A0.70720.70900.73490.117*0.50 (4)
C23A0.541 (2)0.5187 (17)0.7831 (19)0.114 (5)0.50 (4)
H23A0.53030.45340.81990.137*0.50 (4)
O21A0.672 (2)0.5622 (18)0.8019 (16)0.108 (4)0.50 (4)
C21B0.6287 (19)0.630 (2)0.761 (3)0.107 (5)0.50 (4)
H21B0.71090.67140.77180.128*0.50 (4)
C23B0.491 (3)0.4915 (12)0.778 (2)0.106 (4)0.50 (4)
H23B0.45680.42600.79650.127*0.50 (4)
O21B0.628 (3)0.5338 (18)0.815 (2)0.128 (4)0.50 (4)
C240.5332 (3)1.1562 (3)0.7919 (3)0.0679 (7)
C250.6328 (3)1.1268 (4)0.9178 (4)0.0864 (10)
H25A0.59211.07020.95690.130*
H25B0.64881.18680.97550.130*
H25C0.72231.10420.90330.130*
C280.0404 (4)1.3198 (3)0.7908 (4)0.0841 (9)
H28A0.00841.35440.72270.126*
H28B0.06841.37200.84530.126*
H28C0.12091.27530.75240.126*
C290.2045 (3)1.3253 (3)0.9437 (4)0.0739 (7)
H29A0.24291.36050.87990.111*
H29B0.27861.28421.00080.111*
H29C0.16891.37680.99400.111*
C300.1116 (3)1.0445 (3)0.4700 (2)0.0661 (7)
H30A0.05690.98220.43770.099*
H30B0.16531.06550.40950.099*
H30C0.04771.10050.47900.099*
O30.0044 (4)1.2513 (2)1.0673 (3)0.1075 (11)
O70.41462 (18)1.09773 (15)0.76450 (16)0.0550 (4)
O150.2972 (2)0.8989 (2)0.45239 (15)0.0770 (6)
O160.6515 (3)0.8264 (3)0.5795 (4)0.1098 (10)
O240.5543 (4)1.2244 (4)0.7189 (4)0.1373 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0585 (12)0.0458 (11)0.0672 (13)0.0021 (9)0.0302 (10)0.0048 (10)
C20.0630 (12)0.0590 (13)0.0591 (13)0.0051 (11)0.0279 (10)0.0056 (10)
C30.0622 (13)0.0563 (13)0.0616 (12)0.0027 (10)0.0199 (10)0.0090 (11)
C40.0541 (11)0.0432 (10)0.0610 (12)0.0041 (9)0.0140 (9)0.0021 (9)
C50.0464 (9)0.0383 (9)0.0473 (9)0.0008 (8)0.0103 (7)0.0020 (7)
C60.0634 (12)0.0441 (10)0.0586 (11)0.0031 (9)0.0193 (10)0.0096 (9)
C70.0560 (11)0.0531 (12)0.0493 (10)0.0067 (9)0.0185 (9)0.0075 (8)
C80.0496 (10)0.0514 (11)0.0418 (9)0.0014 (9)0.0143 (8)0.0022 (8)
C90.0432 (9)0.0412 (9)0.0434 (9)0.0038 (7)0.0112 (7)0.0013 (7)
C100.0438 (9)0.0412 (9)0.0495 (9)0.0007 (7)0.0124 (8)0.0020 (8)
C110.0540 (11)0.0516 (12)0.0629 (12)0.0108 (9)0.0175 (9)0.0109 (10)
C120.0752 (16)0.0476 (12)0.104 (2)0.0086 (12)0.0409 (15)0.0177 (13)
C130.0591 (11)0.0486 (11)0.0513 (10)0.0025 (9)0.0178 (9)0.0090 (9)
C140.0508 (10)0.0605 (13)0.0398 (8)0.0029 (9)0.0133 (8)0.0054 (9)
C150.0762 (17)0.085 (2)0.0783 (17)0.0059 (15)0.0444 (14)0.0061 (16)
C160.0645 (14)0.097 (2)0.0707 (15)0.0104 (15)0.0259 (12)0.0165 (15)
C170.0681 (14)0.0661 (15)0.0559 (12)0.0117 (12)0.0134 (10)0.0159 (11)
C180.0888 (18)0.0593 (15)0.0491 (11)0.0210 (13)0.0090 (11)0.0055 (10)
C190.0470 (11)0.0715 (16)0.0711 (14)0.0020 (11)0.0070 (10)0.0033 (13)
C200.104 (2)0.078 (2)0.0664 (15)0.0301 (18)0.0176 (15)0.0204 (15)
C220.146 (4)0.068 (2)0.109 (3)0.018 (2)0.056 (3)0.003 (2)
C21A0.116 (6)0.088 (9)0.077 (6)0.058 (5)0.004 (5)0.010 (6)
C23A0.180 (12)0.067 (8)0.101 (7)0.027 (9)0.048 (9)0.007 (6)
O21A0.142 (7)0.083 (8)0.092 (4)0.044 (6)0.016 (5)0.007 (5)
C21B0.125 (7)0.084 (10)0.093 (9)0.043 (6)0.005 (6)0.020 (7)
C23B0.170 (11)0.050 (6)0.114 (6)0.026 (6)0.068 (7)0.010 (5)
O21B0.170 (9)0.083 (7)0.121 (7)0.054 (7)0.023 (7)0.002 (6)
C240.0519 (13)0.0685 (16)0.0881 (17)0.0158 (11)0.0269 (12)0.0096 (14)
C250.0547 (14)0.106 (3)0.093 (2)0.0126 (16)0.0085 (13)0.019 (2)
C280.091 (2)0.0629 (18)0.0911 (19)0.0323 (16)0.0105 (16)0.0028 (15)
C290.0724 (15)0.0561 (14)0.0970 (19)0.0136 (13)0.0288 (14)0.0232 (14)
C300.0674 (14)0.0810 (18)0.0471 (10)0.0101 (13)0.0097 (10)0.0027 (12)
O30.162 (3)0.0747 (15)0.114 (2)0.0165 (18)0.086 (2)0.0340 (15)
O70.0479 (8)0.0587 (9)0.0592 (9)0.0092 (7)0.0155 (6)0.0023 (7)
O150.0816 (12)0.1083 (18)0.0425 (8)0.0205 (12)0.0187 (8)0.0086 (9)
O160.0646 (12)0.134 (3)0.138 (2)0.0127 (16)0.0398 (14)0.023 (2)
O240.094 (2)0.151 (3)0.156 (3)0.064 (2)0.0115 (19)0.051 (3)
Geometric parameters (Å, º) top
C1—C21.329 (4)C16—O161.207 (4)
C1—C101.516 (3)C16—C171.519 (5)
C1—H10.9300C17—C201.493 (5)
C2—C31.459 (4)C17—H170.9800
C2—H20.9300C18—H18A0.9600
C3—O31.221 (3)C18—H18B0.9600
C3—C41.525 (4)C18—H18C0.9600
C4—C291.530 (4)C19—H19A0.9600
C4—C281.534 (4)C19—H19B0.9600
C4—C51.554 (3)C19—H19C0.9600
C5—C61.534 (3)C20—C21B1.382 (13)
C5—C101.554 (3)C20—C21A1.377 (12)
C5—H50.9800C20—C221.405 (7)
C6—C71.521 (4)C22—C23B1.311 (13)
C6—H6A0.9700C22—C23A1.374 (14)
C6—H6B0.9700C22—H220.9300
C7—O71.460 (3)C21A—O21A1.360 (14)
C7—C81.531 (3)C21A—H21A0.9300
C7—H70.9800C23A—O21A1.351 (5)
C8—C141.546 (3)C23A—H23A0.9300
C8—C301.551 (3)C21B—O21B1.349 (16)
C8—C91.561 (3)C21B—H21B0.9300
C9—C111.542 (3)C23B—O21B1.392 (16)
C9—C101.564 (3)C23B—H23B0.9300
C9—H90.9800C24—O241.209 (5)
C10—C191.548 (3)C24—O71.330 (3)
C11—C121.526 (4)C24—C251.472 (5)
C11—H11A0.9700C25—H25A0.9600
C11—H11B0.9700C25—H25B0.9600
C12—C131.535 (4)C25—H25C0.9600
C12—H12A0.9700C28—H28A0.9600
C12—H12B0.9700C28—H28B0.9600
C13—C141.541 (4)C28—H28C0.9600
C13—C181.543 (3)C29—H29A0.9600
C13—C171.576 (3)C29—H29B0.9600
C14—O151.448 (2)C29—H29C0.9600
C14—C151.483 (3)C30—H30A0.9600
C15—O151.429 (4)C30—H30B0.9600
C15—C161.491 (5)C30—H30C0.9600
C15—H150.9800
C2—C1—C10122.7 (2)O15—C15—H15122.0
C2—C1—H1118.6C14—C15—H15122.0
C10—C1—H1118.6C16—C15—H15122.0
C1—C2—C3123.6 (2)O16—C16—C15126.0 (4)
C1—C2—H2118.2O16—C16—C17127.6 (4)
C3—C2—H2118.2C15—C16—C17106.3 (2)
O3—C3—C2118.7 (3)C20—C17—C16117.2 (3)
O3—C3—C4121.4 (3)C20—C17—C13117.0 (2)
C2—C3—C4119.8 (2)C16—C17—C13101.3 (2)
C3—C4—C29106.6 (2)C20—C17—H17106.9
C3—C4—C28107.4 (2)C16—C17—H17106.9
C29—C4—C28108.9 (3)C13—C17—H17106.9
C3—C4—C5108.51 (19)C13—C18—H18A109.5
C29—C4—C5109.4 (2)C13—C18—H18B109.5
C28—C4—C5115.6 (2)H18A—C18—H18B109.5
C6—C5—C4114.57 (18)C13—C18—H18C109.5
C6—C5—C10112.29 (17)H18A—C18—H18C109.5
C4—C5—C10116.36 (17)H18B—C18—H18C109.5
C6—C5—H5103.9C10—C19—H19A109.5
C4—C5—H5103.9C10—C19—H19B109.5
C10—C5—H5103.9H19A—C19—H19B109.5
C7—C6—C5110.67 (18)C10—C19—H19C109.5
C7—C6—H6A109.5H19A—C19—H19C109.5
C5—C6—H6A109.5H19B—C19—H19C109.5
C7—C6—H6B109.5C21B—C20—C2295.9 (13)
C5—C6—H6B109.5C21A—C20—C22113.4 (12)
H6A—C6—H6B108.1C21B—C20—C17139.1 (13)
O7—C7—C6107.96 (18)C21A—C20—C17121.5 (12)
O7—C7—C8106.85 (18)C22—C20—C17125.0 (4)
C6—C7—C8112.01 (18)C23B—C22—C20121.3 (14)
O7—C7—H7110.0C23A—C22—C2096.3 (12)
C6—C7—H7110.0C23B—C22—H22106.9
C8—C7—H7110.0C23A—C22—H22131.9
C7—C8—C14112.81 (17)C20—C22—H22131.9
C7—C8—C30106.1 (2)O21A—C21A—C20108.2 (15)
C14—C8—C30108.13 (18)O21A—C21A—H21A125.9
C7—C8—C9110.38 (16)C20—C21A—H21A125.9
C14—C8—C9106.00 (17)C22—C23A—O21A120.1 (14)
C30—C8—C9113.59 (19)C22—C23A—H23A119.9
C11—C9—C8109.36 (17)O21A—C23A—H23A119.9
C11—C9—C10116.89 (17)C21A—O21A—C23A101.9 (13)
C8—C9—C10115.56 (17)O21B—C21B—C20113.4 (16)
C11—C9—H9104.5O21B—C21B—H21B123.3
C8—C9—H9104.5C20—C21B—H21B123.3
C10—C9—H9104.5C22—C23B—O21B99.7 (13)
C1—C10—C19106.69 (19)C22—C23B—H23B130.2
C1—C10—C5106.35 (18)O21B—C23B—H23B130.2
C19—C10—C5116.6 (2)C21B—O21B—C23B109.7 (14)
C1—C10—C9106.94 (17)O24—C24—O7122.4 (3)
C19—C10—C9113.66 (18)O24—C24—C25125.3 (3)
C5—C10—C9106.01 (15)O7—C24—C25112.2 (3)
C12—C11—C9112.77 (19)C24—C25—H25A109.5
C12—C11—H11A109.0C24—C25—H25B109.5
C9—C11—H11A109.0H25A—C25—H25B109.5
C12—C11—H11B109.0C24—C25—H25C109.5
C9—C11—H11B109.0H25A—C25—H25C109.5
H11A—C11—H11B107.8H25B—C25—H25C109.5
C11—C12—C13114.1 (2)C4—C28—H28A109.5
C11—C12—H12A108.7C4—C28—H28B109.5
C13—C12—H12A108.7H28A—C28—H28B109.5
C11—C12—H12B108.7C4—C28—H28C109.5
C13—C12—H12B108.7H28A—C28—H28C109.5
H12A—C12—H12B107.6H28B—C28—H28C109.5
C12—C13—C14108.7 (2)C4—C29—H29A109.5
C12—C13—C18113.0 (2)C4—C29—H29B109.5
C14—C13—C18111.8 (2)H29A—C29—H29B109.5
C12—C13—C17115.4 (2)C4—C29—H29C109.5
C14—C13—C17101.88 (19)H29A—C29—H29C109.5
C18—C13—C17105.5 (2)H29B—C29—H29C109.5
O15—C14—C1558.35 (18)C8—C30—H30A109.5
O15—C14—C13110.5 (2)C8—C30—H30B109.5
C15—C14—C13108.0 (2)H30A—C30—H30B109.5
O15—C14—C8113.26 (18)C8—C30—H30C109.5
C15—C14—C8128.0 (2)H30A—C30—H30C109.5
C13—C14—C8121.02 (16)H30B—C30—H30C109.5
O15—C15—C1459.59 (16)C24—O7—C7119.3 (2)
O15—C15—C16108.4 (3)C15—O15—C1462.06 (15)
C14—C15—C16106.9 (3)
C10—C1—C2—C32.2 (4)C7—C8—C14—O15109.9 (2)
C1—C2—C3—O3167.8 (3)C30—C8—C14—O157.0 (3)
C1—C2—C3—C410.7 (4)C9—C8—C14—O15129.2 (2)
O3—C3—C4—C2950.0 (4)C7—C8—C14—C1542.8 (3)
C2—C3—C4—C29131.6 (3)C30—C8—C14—C1574.1 (3)
O3—C3—C4—C2866.6 (4)C9—C8—C14—C15163.7 (2)
C2—C3—C4—C28111.8 (3)C7—C8—C14—C13115.4 (2)
O3—C3—C4—C5167.8 (3)C30—C8—C14—C13127.6 (2)
C2—C3—C4—C513.8 (3)C9—C8—C14—C135.5 (2)
C3—C4—C5—C6178.81 (19)C13—C14—C15—O15103.4 (2)
C29—C4—C5—C662.9 (3)C8—C14—C15—O1596.1 (3)
C28—C4—C5—C660.5 (3)O15—C14—C15—C16101.8 (3)
C3—C4—C5—C1047.4 (2)C13—C14—C15—C161.6 (3)
C29—C4—C5—C10163.4 (2)C8—C14—C15—C16162.1 (2)
C28—C4—C5—C1073.3 (3)O15—C15—C16—O16143.5 (3)
C4—C5—C6—C7162.83 (19)C14—C15—C16—O16153.6 (3)
C10—C5—C6—C761.5 (2)O15—C15—C16—C1739.6 (3)
C5—C6—C7—O760.2 (2)C14—C15—C16—C1723.2 (3)
C5—C6—C7—C857.2 (2)O16—C16—C17—C2010.6 (5)
O7—C7—C8—C1451.9 (2)C15—C16—C17—C20166.2 (2)
C6—C7—C8—C14169.92 (16)O16—C16—C17—C13139.1 (3)
O7—C7—C8—C30170.07 (18)C15—C16—C17—C1337.7 (3)
C6—C7—C8—C3071.9 (2)C12—C13—C17—C2076.8 (3)
O7—C7—C8—C966.5 (2)C14—C13—C17—C20165.7 (3)
C6—C7—C8—C951.5 (2)C18—C13—C17—C2048.8 (3)
C7—C8—C9—C11173.71 (17)C12—C13—C17—C16154.6 (3)
C14—C8—C9—C1151.2 (2)C14—C13—C17—C1637.1 (2)
C30—C8—C9—C1167.3 (2)C18—C13—C17—C1679.9 (3)
C7—C8—C9—C1051.9 (2)C16—C17—C20—C21B16 (2)
C14—C8—C9—C10174.36 (16)C13—C17—C20—C21B104 (2)
C30—C8—C9—C1067.1 (3)C16—C17—C20—C21A10.8 (13)
C2—C1—C10—C1996.5 (3)C13—C17—C20—C21A109.8 (13)
C2—C1—C10—C528.6 (3)C16—C17—C20—C22166.3 (3)
C2—C1—C10—C9141.6 (2)C13—C17—C20—C2273.1 (4)
C6—C5—C10—C1170.88 (18)C21B—C20—C22—C23B2.4 (17)
C4—C5—C10—C154.3 (2)C21A—C20—C22—C23B2.0 (17)
C6—C5—C10—C1970.3 (2)C17—C20—C22—C23B179.4 (11)
C4—C5—C10—C1964.5 (2)C21B—C20—C22—C23A2.0 (16)
C6—C5—C10—C957.3 (2)C21A—C20—C22—C23A2.5 (15)
C4—C5—C10—C9167.90 (16)C17—C20—C22—C23A179.8 (10)
C11—C9—C10—C162.4 (2)C21B—C20—C21A—O21A14 (6)
C8—C9—C10—C1166.65 (18)C22—C20—C21A—O21A1.0 (19)
C11—C9—C10—C1955.0 (3)C17—C20—C21A—O21A178.4 (10)
C8—C9—C10—C1975.9 (2)C23B—C22—C23A—O21A176 (5)
C11—C9—C10—C5175.63 (17)C20—C22—C23A—O21A3.5 (18)
C8—C9—C10—C553.5 (2)C20—C21A—O21A—C23A1.1 (19)
C8—C9—C11—C1265.6 (3)C22—C23A—O21A—C21A3 (2)
C10—C9—C11—C12160.7 (2)C21A—C20—C21B—O21B166 (9)
C9—C11—C12—C1316.5 (4)C22—C20—C21B—O21B0 (2)
C11—C12—C13—C1437.2 (3)C17—C20—C21B—O21B178.1 (11)
C11—C12—C13—C1887.5 (3)C23A—C22—C23B—O21B2 (3)
C11—C12—C13—C17150.9 (2)C20—C22—C23B—O21B3.3 (19)
C12—C13—C14—O1584.5 (2)C20—C21B—O21B—C23B1 (3)
C18—C13—C14—O15150.0 (2)C22—C23B—O21B—C21B3 (2)
C17—C13—C14—O1537.8 (2)O24—C24—O7—C76.7 (5)
C12—C13—C14—C15146.6 (2)C25—C24—O7—C7174.1 (3)
C18—C13—C14—C1587.9 (3)C6—C7—O7—C2486.1 (2)
C17—C13—C14—C1524.4 (3)C8—C7—O7—C24153.2 (2)
C12—C13—C14—C851.2 (3)C16—C15—O15—C1499.2 (3)
C18—C13—C14—C874.2 (3)C13—C14—O15—C1599.1 (3)
C17—C13—C14—C8173.51 (19)C8—C14—O15—C15121.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···O3i0.972.523.374 (3)147
C1—H1···O3i0.932.603.509 (4)166
Symmetry code: (i) x, y1/2, z+2.
 

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