Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030728/ob2039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030728/ob2039Isup2.hkl |
CCDC reference: 621446
Data collection: XSCANS (Siemens, 1993); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C24H34O4 | F(000) = 420 |
Mr = 386.51 | Dx = 1.202 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 39 reflections |
a = 9.8290 (12) Å | θ = 10.0–24.6° |
b = 6.6580 (18) Å | µ = 0.08 mm−1 |
c = 16.566 (2) Å | T = 298 K |
β = 99.910 (9)° | Plate, colorless |
V = 1067.9 (3) Å3 | 0.5 × 0.4 × 0.2 mm |
Z = 2 |
Siemens P4 diffractometer | θmax = 28°, θmin = 2.1° |
Graphite monochromator | h = −1→12 |
2θ/ω scans | k = −1→8 |
3706 measured reflections | l = −21→21 |
2756 independent reflections | 3 standard reflections every 97 reflections |
2167 reflections with I > 2σ(I) | intensity decay: 7.2% |
Rint = 0.034 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0744P)2] where P = (Fo2 + 2Fc2)/3 |
2756 reflections | (Δ/σ)max = 0.004 |
267 parameters | Δρmax = 0.18 e Å−3 |
1 restraint | Δρmin = −0.18 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.5214 (3) | 0.2800 (5) | 0.61625 (16) | 0.0543 (7) | |
H1A | 0.4486 | 0.2329 | 0.5733 | 0.065* | |
H1B | 0.4909 | 0.4056 | 0.6368 | 0.065* | |
C2 | 0.6522 (3) | 0.3198 (6) | 0.57892 (17) | 0.0637 (9) | |
H2A | 0.6784 | 0.1983 | 0.5532 | 0.076* | |
H2B | 0.6331 | 0.4231 | 0.5372 | 0.076* | |
C3 | 0.7695 (3) | 0.3867 (5) | 0.64487 (17) | 0.0518 (6) | |
H3 | 0.7476 | 0.517 | 0.6669 | 0.062* | |
C4 | 0.7982 (3) | 0.2345 (5) | 0.71310 (17) | 0.0505 (6) | |
H4A | 0.8694 | 0.2854 | 0.7561 | 0.061* | |
H4B | 0.8318 | 0.1112 | 0.6923 | 0.061* | |
C5 | 0.6692 (2) | 0.1912 (4) | 0.74790 (14) | 0.0402 (5) | |
C6 | 0.6702 (3) | 0.2066 (5) | 0.82859 (15) | 0.0469 (6) | |
H6 | 0.7499 | 0.2554 | 0.8611 | 0.056* | |
C7 | 0.5520 (3) | 0.1506 (5) | 0.86980 (14) | 0.0521 (7) | |
H7A | 0.508 | 0.2717 | 0.8852 | 0.063* | |
H7B | 0.5864 | 0.0761 | 0.9194 | 0.063* | |
C8 | 0.4458 (2) | 0.0234 (4) | 0.81426 (12) | 0.0384 (5) | |
H8 | 0.4853 | −0.1099 | 0.8085 | 0.046* | |
C9 | 0.4128 (2) | 0.1226 (4) | 0.72860 (13) | 0.0373 (5) | |
H9 | 0.3913 | 0.2635 | 0.738 | 0.045* | |
C10 | 0.5424 (2) | 0.1246 (4) | 0.68651 (12) | 0.0377 (5) | |
C11 | 0.2836 (2) | 0.0345 (5) | 0.67333 (13) | 0.0456 (6) | |
H11A | 0.2563 | 0.1244 | 0.6273 | 0.055* | |
H11B | 0.3084 | −0.0931 | 0.6516 | 0.055* | |
C12 | 0.1589 (2) | 0.0014 (5) | 0.71655 (15) | 0.0462 (6) | |
H12A | 0.1225 | 0.1304 | 0.7299 | 0.055* | |
H12B | 0.0868 | −0.0689 | 0.68 | 0.055* | |
C13 | 0.2010 (2) | −0.1216 (4) | 0.79541 (13) | 0.0383 (5) | |
C14 | 0.3144 (2) | −0.0005 (4) | 0.85007 (13) | 0.0407 (5) | |
H14 | 0.2774 | 0.1348 | 0.8549 | 0.049* | |
C15 | 0.3251 (3) | −0.0998 (5) | 0.93500 (14) | 0.0553 (7) | |
H15A | 0.3845 | −0.217 | 0.9395 | 0.066* | |
H15B | 0.3604 | −0.0061 | 0.9784 | 0.066* | |
C16 | 0.1759 (3) | −0.1585 (5) | 0.93837 (15) | 0.0500 (6) | |
H16 | 0.1384 | −0.0759 | 0.9783 | 0.06* | |
C17 | 0.0910 (3) | −0.1317 (4) | 0.85226 (14) | 0.0421 (5) | |
H17 | 0.0395 | −0.0052 | 0.8493 | 0.05* | |
C18 | 0.2492 (3) | −0.3326 (4) | 0.77581 (15) | 0.0465 (6) | |
H18A | 0.1736 | −0.4046 | 0.7442 | 0.07* | |
H18B | 0.2812 | −0.4034 | 0.826 | 0.07* | |
H18C | 0.3231 | −0.3218 | 0.745 | 0.07* | |
C19 | 0.5707 (3) | −0.0847 (5) | 0.65311 (18) | 0.0536 (7) | |
H19A | 0.6575 | −0.0831 | 0.6341 | 0.08* | |
H19B | 0.4983 | −0.1186 | 0.6085 | 0.08* | |
H19C | 0.5738 | −0.1826 | 0.6959 | 0.08* | |
C20 | −0.0091 (2) | −0.3092 (4) | 0.84406 (15) | 0.0455 (6) | |
H20 | −0.0227 | −0.363 | 0.7882 | 0.055* | |
C21 | −0.1494 (3) | −0.2582 (5) | 0.8686 (2) | 0.0626 (8) | |
H21A | −0.2044 | −0.3777 | 0.8667 | 0.094* | |
H21B | −0.1965 | −0.1606 | 0.8312 | 0.094* | |
H21C | −0.1346 | −0.2044 | 0.9232 | 0.094* | |
C22 | 0.0647 (3) | −0.4611 (5) | 0.90395 (17) | 0.0501 (6) | |
C23 | 0.9293 (3) | 0.5776 (5) | 0.58166 (18) | 0.0570 (7) | |
C25 | 1.0621 (3) | 0.5690 (6) | 0.5488 (2) | 0.0665 (9) | |
H25A | 1.0425 | 0.5482 | 0.4906 | 0.1* | |
H25B | 1.1175 | 0.4601 | 0.5743 | 0.1* | |
H25C | 1.1112 | 0.6931 | 0.5605 | 0.1* | |
O1 | 0.1660 (2) | −0.3728 (3) | 0.95721 (11) | 0.0561 (5) | |
O2 | 0.0404 (2) | −0.6371 (3) | 0.90811 (14) | 0.0669 (6) | |
O3 | 0.8980 (2) | 0.4018 (4) | 0.61093 (13) | 0.0630 (6) | |
O4A | 0.876 (3) | 0.7335 (16) | 0.594 (3) | 0.083 (6) | 0.56 (9) |
O4B | 0.834 (4) | 0.700 (6) | 0.562 (2) | 0.080 (7) | 0.44 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0480 (15) | 0.0664 (19) | 0.0486 (13) | 0.0009 (14) | 0.0084 (11) | 0.0146 (13) |
C2 | 0.0583 (16) | 0.086 (2) | 0.0490 (13) | −0.0004 (17) | 0.0163 (12) | 0.0172 (17) |
C3 | 0.0481 (13) | 0.0514 (15) | 0.0617 (15) | −0.0004 (14) | 0.0255 (12) | 0.0060 (14) |
C4 | 0.0424 (13) | 0.0522 (16) | 0.0581 (14) | −0.0034 (13) | 0.0117 (11) | 0.0027 (13) |
C5 | 0.0370 (11) | 0.0353 (11) | 0.0478 (11) | −0.0014 (10) | 0.0057 (9) | 0.0044 (11) |
C6 | 0.0430 (12) | 0.0494 (14) | 0.0456 (11) | −0.0096 (12) | 0.0004 (10) | −0.0003 (12) |
C7 | 0.0546 (14) | 0.0638 (18) | 0.0372 (11) | −0.0155 (14) | 0.0058 (10) | −0.0065 (13) |
C8 | 0.0412 (11) | 0.0408 (13) | 0.0320 (10) | −0.0019 (11) | 0.0032 (9) | 0.0001 (10) |
C9 | 0.0391 (10) | 0.0346 (11) | 0.0380 (10) | 0.0028 (10) | 0.0059 (9) | 0.0016 (10) |
C10 | 0.0353 (10) | 0.0418 (12) | 0.0366 (10) | 0.0012 (10) | 0.0074 (9) | −0.0009 (10) |
C11 | 0.0402 (12) | 0.0602 (17) | 0.0352 (10) | −0.0016 (12) | 0.0027 (9) | 0.0063 (12) |
C12 | 0.0377 (11) | 0.0551 (15) | 0.0447 (12) | 0.0011 (12) | 0.0038 (9) | 0.0094 (12) |
C13 | 0.0378 (11) | 0.0396 (12) | 0.0377 (10) | 0.0013 (11) | 0.0071 (9) | −0.0003 (10) |
C14 | 0.0448 (12) | 0.0405 (13) | 0.0375 (10) | −0.0058 (11) | 0.0090 (9) | −0.0028 (10) |
C15 | 0.0585 (15) | 0.073 (2) | 0.0343 (11) | −0.0175 (16) | 0.0075 (10) | 0.0004 (13) |
C16 | 0.0594 (15) | 0.0525 (16) | 0.0407 (11) | −0.0109 (13) | 0.0160 (11) | −0.0033 (12) |
C17 | 0.0444 (12) | 0.0368 (12) | 0.0470 (12) | −0.0010 (11) | 0.0135 (10) | −0.0017 (11) |
C18 | 0.0497 (13) | 0.0417 (14) | 0.0480 (12) | 0.0013 (12) | 0.0083 (11) | −0.0048 (12) |
C19 | 0.0504 (14) | 0.0525 (16) | 0.0601 (15) | −0.0002 (13) | 0.0156 (12) | −0.0169 (14) |
C20 | 0.0450 (13) | 0.0413 (14) | 0.0502 (12) | −0.0062 (12) | 0.0080 (10) | 0.0015 (12) |
C21 | 0.0454 (14) | 0.0569 (18) | 0.087 (2) | −0.0009 (14) | 0.0151 (14) | 0.0108 (17) |
C22 | 0.0532 (14) | 0.0452 (15) | 0.0543 (14) | −0.0046 (13) | 0.0158 (12) | 0.0033 (13) |
C23 | 0.0558 (16) | 0.0599 (19) | 0.0617 (16) | −0.0062 (15) | 0.0277 (14) | −0.0021 (15) |
C25 | 0.0667 (18) | 0.072 (2) | 0.0674 (17) | −0.0108 (17) | 0.0301 (15) | −0.0065 (17) |
O1 | 0.0597 (11) | 0.0590 (12) | 0.0486 (9) | −0.0081 (10) | 0.0061 (8) | 0.0122 (9) |
O2 | 0.0716 (13) | 0.0447 (12) | 0.0844 (13) | −0.0034 (11) | 0.0137 (11) | 0.0095 (11) |
O3 | 0.0576 (12) | 0.0587 (13) | 0.0814 (13) | 0.0007 (11) | 0.0365 (10) | 0.0048 (11) |
O4A | 0.072 (8) | 0.052 (3) | 0.140 (14) | −0.008 (4) | 0.057 (9) | −0.004 (5) |
O4B | 0.076 (9) | 0.065 (10) | 0.107 (12) | 0.003 (8) | 0.039 (9) | 0.025 (7) |
C1—C2 | 1.542 (4) | C13—C14 | 1.538 (3) |
C1—C10 | 1.545 (4) | C13—C17 | 1.552 (3) |
C1—H1A | 0.97 | C14—C15 | 1.542 (3) |
C1—H1B | 0.97 | C14—H14 | 0.98 |
C2—C3 | 1.513 (4) | C15—C16 | 1.528 (4) |
C2—H2A | 0.97 | C15—H15A | 0.97 |
C2—H2B | 0.97 | C15—H15B | 0.97 |
C3—O3 | 1.472 (3) | C16—O1 | 1.467 (4) |
C3—C4 | 1.508 (4) | C16—C17 | 1.534 (4) |
C3—H3 | 0.98 | C16—H16 | 0.98 |
C4—C5 | 1.509 (3) | C17—C20 | 1.529 (4) |
C4—H4A | 0.97 | C17—H17 | 0.98 |
C4—H4B | 0.97 | C18—H18A | 0.96 |
C5—C6 | 1.339 (3) | C18—H18B | 0.96 |
C5—C10 | 1.532 (3) | C18—H18C | 0.96 |
C6—C7 | 1.493 (3) | C19—H19A | 0.96 |
C6—H6 | 0.93 | C19—H19B | 0.96 |
C7—C8 | 1.524 (3) | C19—H19C | 0.96 |
C7—H7A | 0.97 | C20—C22 | 1.512 (4) |
C7—H7B | 0.97 | C20—C21 | 1.541 (4) |
C8—C14 | 1.519 (3) | C20—H20 | 0.98 |
C8—C9 | 1.548 (3) | C21—H21A | 0.96 |
C8—H8 | 0.98 | C21—H21B | 0.96 |
C9—C11 | 1.548 (3) | C21—H21C | 0.96 |
C9—C10 | 1.554 (3) | C22—O2 | 1.200 (4) |
C9—H9 | 0.98 | C22—O1 | 1.347 (4) |
C10—C19 | 1.542 (4) | C23—O4A | 1.195 (12) |
C11—C12 | 1.538 (3) | C23—O4B | 1.239 (16) |
C11—H11A | 0.97 | C23—O3 | 1.324 (4) |
C11—H11B | 0.97 | C23—C25 | 1.498 (4) |
C12—C13 | 1.537 (3) | C25—H25A | 0.96 |
C12—H12A | 0.97 | C25—H25B | 0.96 |
C12—H12B | 0.97 | C25—H25C | 0.96 |
C13—C18 | 1.535 (4) | ||
C2—C1—C10 | 113.9 (2) | C12—C13—C14 | 106.4 (2) |
C2—C1—H1A | 108.8 | C18—C13—C17 | 111.2 (2) |
C10—C1—H1A | 108.8 | C12—C13—C17 | 115.18 (19) |
C2—C1—H1B | 108.8 | C14—C13—C17 | 100.09 (17) |
C10—C1—H1B | 108.8 | C8—C14—C13 | 113.82 (18) |
H1A—C1—H1B | 107.7 | C8—C14—C15 | 118.2 (2) |
C3—C2—C1 | 110.2 (2) | C13—C14—C15 | 103.9 (2) |
C3—C2—H2A | 109.6 | C8—C14—H14 | 106.7 |
C1—C2—H2A | 109.6 | C13—C14—H14 | 106.7 |
C3—C2—H2B | 109.6 | C15—C14—H14 | 106.7 |
C1—C2—H2B | 109.6 | C16—C15—C14 | 103.2 (2) |
H2A—C2—H2B | 108.1 | C16—C15—H15A | 111.1 |
O3—C3—C4 | 105.7 (2) | C14—C15—H15A | 111.1 |
O3—C3—C2 | 110.0 (2) | C16—C15—H15B | 111.1 |
C4—C3—C2 | 111.4 (3) | C14—C15—H15B | 111.1 |
O3—C3—H3 | 109.9 | H15A—C15—H15B | 109.1 |
C4—C3—H3 | 109.9 | O1—C16—C15 | 110.8 (3) |
C2—C3—H3 | 109.9 | O1—C16—C17 | 105.4 (2) |
C3—C4—C5 | 110.7 (2) | C15—C16—C17 | 107.9 (2) |
C3—C4—H4A | 109.5 | O1—C16—H16 | 110.8 |
C5—C4—H4A | 109.5 | C15—C16—H16 | 110.8 |
C3—C4—H4B | 109.5 | C17—C16—H16 | 110.8 |
C5—C4—H4B | 109.5 | C20—C17—C16 | 103.4 (2) |
H4A—C4—H4B | 108.1 | C20—C17—C13 | 119.0 (2) |
C6—C5—C4 | 120.3 (2) | C16—C17—C13 | 104.22 (19) |
C6—C5—C10 | 123.4 (2) | C20—C17—H17 | 109.9 |
C4—C5—C10 | 116.3 (2) | C16—C17—H17 | 109.9 |
C5—C6—C7 | 124.4 (2) | C13—C17—H17 | 109.9 |
C5—C6—H6 | 117.8 | C13—C18—H18A | 109.5 |
C7—C6—H6 | 117.8 | C13—C18—H18B | 109.5 |
C6—C7—C8 | 111.64 (19) | H18A—C18—H18B | 109.5 |
C6—C7—H7A | 109.3 | C13—C18—H18C | 109.5 |
C8—C7—H7A | 109.3 | H18A—C18—H18C | 109.5 |
C6—C7—H7B | 109.3 | H18B—C18—H18C | 109.5 |
C8—C7—H7B | 109.3 | C10—C19—H19A | 109.5 |
H7A—C7—H7B | 108 | C10—C19—H19B | 109.5 |
C14—C8—C7 | 111.24 (19) | H19A—C19—H19B | 109.5 |
C14—C8—C9 | 110.14 (17) | C10—C19—H19C | 109.5 |
C7—C8—C9 | 109.3 (2) | H19A—C19—H19C | 109.5 |
C14—C8—H8 | 108.7 | H19B—C19—H19C | 109.5 |
C7—C8—H8 | 108.7 | C22—C20—C17 | 103.3 (2) |
C9—C8—H8 | 108.7 | C22—C20—C21 | 108.9 (2) |
C11—C9—C8 | 113.69 (19) | C17—C20—C21 | 113.4 (2) |
C11—C9—C10 | 112.98 (18) | C22—C20—H20 | 110.3 |
C8—C9—C10 | 110.86 (17) | C17—C20—H20 | 110.3 |
C11—C9—H9 | 106.2 | C21—C20—H20 | 110.3 |
C8—C9—H9 | 106.2 | C20—C21—H21A | 109.5 |
C10—C9—H9 | 106.2 | C20—C21—H21B | 109.5 |
C5—C10—C19 | 108.9 (2) | H21A—C21—H21B | 109.5 |
C5—C10—C1 | 107.1 (2) | C20—C21—H21C | 109.5 |
C19—C10—C1 | 110.1 (2) | H21A—C21—H21C | 109.5 |
C5—C10—C9 | 109.91 (17) | H21B—C21—H21C | 109.5 |
C19—C10—C9 | 111.4 (2) | O2—C22—O1 | 121.4 (3) |
C1—C10—C9 | 109.27 (19) | O2—C22—C20 | 127.8 (3) |
C12—C11—C9 | 114.66 (19) | O1—C22—C20 | 110.8 (2) |
C12—C11—H11A | 108.6 | O4A—C23—O3 | 124.8 (7) |
C9—C11—H11A | 108.6 | O4B—C23—O3 | 117.7 (18) |
C12—C11—H11B | 108.6 | O4A—C23—C25 | 121.9 (6) |
C9—C11—H11B | 108.6 | O4B—C23—C25 | 126.3 (8) |
H11A—C11—H11B | 107.6 | O3—C23—C25 | 111.8 (3) |
C13—C12—C11 | 110.67 (19) | C23—C25—H25A | 109.5 |
C13—C12—H12A | 109.5 | C23—C25—H25B | 109.5 |
C11—C12—H12A | 109.5 | H25A—C25—H25B | 109.5 |
C13—C12—H12B | 109.5 | C23—C25—H25C | 109.5 |
C11—C12—H12B | 109.5 | H25A—C25—H25C | 109.5 |
H12A—C12—H12B | 108.1 | H25B—C25—H25C | 109.5 |
C18—C13—C12 | 110.8 (2) | C22—O1—C16 | 110.7 (2) |
C18—C13—C14 | 112.6 (2) | C23—O3—C3 | 118.0 (2) |
C10—C1—C2—C3 | −56.5 (4) | C7—C8—C14—C15 | −59.6 (3) |
C1—C2—C3—O3 | 173.4 (3) | C9—C8—C14—C15 | 179.1 (2) |
C1—C2—C3—C4 | 56.6 (4) | C18—C13—C14—C8 | 57.3 (3) |
O3—C3—C4—C5 | −174.7 (2) | C12—C13—C14—C8 | −64.4 (3) |
C2—C3—C4—C5 | −55.3 (3) | C17—C13—C14—C8 | 175.4 (2) |
C3—C4—C5—C6 | −127.1 (3) | C18—C13—C14—C15 | −72.6 (2) |
C3—C4—C5—C10 | 54.6 (3) | C12—C13—C14—C15 | 165.7 (2) |
C4—C5—C6—C7 | −174.6 (3) | C17—C13—C14—C15 | 45.5 (2) |
C10—C5—C6—C7 | 3.6 (5) | C8—C14—C15—C16 | −162.6 (2) |
C5—C6—C7—C8 | 15.2 (4) | C13—C14—C15—C16 | −35.3 (3) |
C6—C7—C8—C14 | −169.5 (2) | C14—C15—C16—O1 | 125.9 (2) |
C6—C7—C8—C9 | −47.7 (3) | C14—C15—C16—C17 | 10.9 (3) |
C14—C8—C9—C11 | −44.5 (3) | O1—C16—C17—C20 | 23.6 (3) |
C7—C8—C9—C11 | −167.0 (2) | C15—C16—C17—C20 | 142.1 (2) |
C14—C8—C9—C10 | −173.1 (2) | O1—C16—C17—C13 | −101.4 (2) |
C7—C8—C9—C10 | 64.4 (3) | C15—C16—C17—C13 | 17.1 (3) |
C6—C5—C10—C19 | −110.6 (3) | C18—C13—C17—C20 | −33.1 (3) |
C4—C5—C10—C19 | 67.6 (3) | C12—C13—C17—C20 | 94.0 (3) |
C6—C5—C10—C1 | 130.3 (3) | C14—C13—C17—C20 | −152.3 (2) |
C4—C5—C10—C1 | −51.4 (3) | C18—C13—C17—C16 | 81.3 (2) |
C6—C5—C10—C9 | 11.7 (4) | C12—C13—C17—C16 | −151.6 (2) |
C4—C5—C10—C9 | −170.1 (2) | C14—C13—C17—C16 | −38.0 (2) |
C2—C1—C10—C5 | 51.7 (3) | C16—C17—C20—C22 | −24.1 (3) |
C2—C1—C10—C19 | −66.6 (3) | C13—C17—C20—C22 | 90.7 (2) |
C2—C1—C10—C9 | 170.7 (2) | C16—C17—C20—C21 | 93.6 (3) |
C11—C9—C10—C5 | −173.6 (2) | C13—C17—C20—C21 | −151.6 (2) |
C8—C9—C10—C5 | −44.7 (3) | C17—C20—C22—O2 | −164.2 (3) |
C11—C9—C10—C19 | −52.9 (3) | C21—C20—C22—O2 | 74.9 (4) |
C8—C9—C10—C19 | 76.1 (2) | C17—C20—C22—O1 | 17.1 (3) |
C11—C9—C10—C1 | 69.1 (3) | C21—C20—C22—O1 | −103.7 (3) |
C8—C9—C10—C1 | −162.0 (2) | O2—C22—O1—C16 | 179.2 (3) |
C8—C9—C11—C12 | 44.1 (3) | C20—C22—O1—C16 | −2.0 (3) |
C10—C9—C11—C12 | 171.6 (2) | C15—C16—O1—C22 | −130.5 (2) |
C9—C11—C12—C13 | −52.2 (3) | C17—C16—O1—C22 | −14.0 (3) |
C11—C12—C13—C18 | −63.3 (3) | O4A—C23—O3—C3 | 15 (3) |
C11—C12—C13—C14 | 59.5 (3) | O4B—C23—O3—C3 | −21 (3) |
C11—C12—C13—C17 | 169.4 (2) | C25—C23—O3—C3 | −179.6 (2) |
C7—C8—C14—C13 | 178.0 (2) | C4—C3—O3—C23 | −147.5 (3) |
C9—C8—C14—C13 | 56.7 (3) | C2—C3—O3—C23 | 92.2 (3) |