Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003550/ci6090sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003550/ci6090Isup2.hkl |
CCDC reference: 183774
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97.
C29H37NO4·0.46H2O | Dx = 1.167 Mg m−3 |
Mr = 471.88 | Cu Kα radiation, λ = 1.54180 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 11.493 (2) Å | θ = 20–30° |
b = 15.285 (2) Å | µ = 0.62 mm−1 |
c = 15.293 (3) Å | T = 293 K |
V = 2686.5 (8) Å3 | Rectangular, colourless |
Z = 4 | 0.35 × 0.2 × 0.2 mm |
F(000) = 1018 |
Enraf-Nonius CAD-4 diffractometer | 2064 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 67.9°, θmin = 4.1° |
ω–2θ scans | h = 0→13 |
Absorption correction: ψ scan (North et al., 1968) | k = −4→18 |
Tmin = 0.818, Tmax = 0.890 | l = 0→18 |
2530 measured reflections | 2 standard reflections every 120 min |
2472 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | Riding |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0607P)2 + 0.3741P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2472 reflections | Δρmax = 0.12 e Å−3 |
316 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0023 (3) |
Experimental. There are 284 normal collision reflections with θ > 57°, for which intensity could not be measured. |
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 | 0.3455 (3) | 0.0677 (2) | 0.4652 (2) | 0.0681 (8) | |
H1A | 0.2806 | 0.0955 | 0.4947 | 0.082* | |
H1B | 0.3259 | 0.0636 | 0.4037 | 0.082* | |
C2 | 0.3593 (3) | −0.0245 (2) | 0.5013 (2) | 0.0775 (9) | |
H2A | 0.3719 | −0.0220 | 0.5640 | 0.093* | |
H2B | 0.2889 | −0.0578 | 0.4905 | 0.093* | |
C3 | 0.4610 (3) | −0.06851 (19) | 0.4579 (2) | 0.0716 (9) | |
H3 | 0.4469 | −0.0740 | 0.3949 | 0.086* | |
C4 | 0.5709 (3) | −0.01700 (19) | 0.4740 (2) | 0.0697 (8) | |
H4A | 0.6354 | −0.0452 | 0.4444 | 0.084* | |
H4B | 0.5877 | −0.0164 | 0.5362 | 0.084* | |
C5 | 0.5590 (3) | 0.07617 (18) | 0.44129 (19) | 0.0585 (7) | |
C6 | 0.6351 (3) | 0.10944 (19) | 0.3856 (2) | 0.0622 (8) | |
H6 | 0.6958 | 0.0735 | 0.3675 | 0.075* | |
C7 | 0.6312 (2) | 0.20010 (18) | 0.34979 (19) | 0.0578 (7) | |
H7A | 0.6060 | 0.1978 | 0.2893 | 0.069* | |
H7B | 0.7090 | 0.2247 | 0.3509 | 0.069* | |
C8 | 0.5498 (2) | 0.25979 (17) | 0.40064 (17) | 0.0520 (6) | |
H8 | 0.5865 | 0.2759 | 0.4562 | 0.062* | |
C9 | 0.4357 (2) | 0.21071 (17) | 0.41926 (17) | 0.0537 (6) | |
H9 | 0.4076 | 0.1904 | 0.3623 | 0.064* | |
C10 | 0.4541 (3) | 0.12698 (18) | 0.47493 (17) | 0.0558 (7) | |
C11 | 0.3392 (3) | 0.27074 (19) | 0.4555 (2) | 0.0680 (8) | |
H11A | 0.2663 | 0.2387 | 0.4555 | 0.082* | |
H11B | 0.3575 | 0.2852 | 0.5157 | 0.082* | |
C12 | 0.3223 (3) | 0.3558 (2) | 0.4044 (2) | 0.0642 (8) | |
H12A | 0.2911 | 0.3427 | 0.3469 | 0.077* | |
H12B | 0.2667 | 0.3928 | 0.4347 | 0.077* | |
C13 | 0.4372 (2) | 0.40409 (18) | 0.39491 (17) | 0.0539 (7) | |
C14 | 0.5237 (2) | 0.34220 (17) | 0.34884 (17) | 0.0516 (6) | |
H14 | 0.4849 | 0.3227 | 0.2952 | 0.062* | |
C15 | 0.6237 (3) | 0.40108 (19) | 0.3194 (2) | 0.0592 (7) | |
H15A | 0.6849 | 0.4026 | 0.3631 | 0.071* | |
H15B | 0.6563 | 0.3807 | 0.2645 | 0.071* | |
C16 | 0.5687 (3) | 0.49046 (19) | 0.30857 (18) | 0.0560 (7) | |
C17 | 0.4401 (2) | 0.47915 (19) | 0.32853 (18) | 0.0569 (7) | |
H17 | 0.3994 | 0.4609 | 0.2752 | 0.068* | |
C18 | 0.4811 (3) | 0.4377 (2) | 0.48346 (18) | 0.0674 (8) | |
H18A | 0.5534 | 0.4680 | 0.4754 | 0.101* | |
H18B | 0.4926 | 0.3891 | 0.5223 | 0.101* | |
H18C | 0.4246 | 0.4769 | 0.5080 | 0.101* | |
C19 | 0.4752 (3) | 0.1483 (2) | 0.57238 (19) | 0.0725 (9) | |
H19A | 0.4863 | 0.0950 | 0.6044 | 0.109* | |
H19B | 0.4091 | 0.1790 | 0.5954 | 0.109* | |
H19C | 0.5433 | 0.1843 | 0.5779 | 0.109* | |
C20 | 0.6183 (3) | 0.5671 (2) | 0.29204 (19) | 0.0637 (8) | |
H20 | 0.5690 | 0.6154 | 0.2931 | 0.076* | |
C21 | 0.7404 (3) | 0.5855 (2) | 0.27241 (19) | 0.0685 (9) | |
C22 | 0.7802 (3) | 0.6708 (3) | 0.2734 (2) | 0.0845 (11) | |
H22 | 0.7300 | 0.7160 | 0.2886 | 0.101* | |
C23 | 0.8941 (4) | 0.6888 (3) | 0.2520 (3) | 0.1049 (14) | |
H23 | 0.9217 | 0.7460 | 0.2520 | 0.126* | |
C24 | 0.9654 (4) | 0.6206 (4) | 0.2308 (3) | 0.1071 (15) | |
H24 | 1.0427 | 0.6305 | 0.2157 | 0.129* | |
C25 | 0.9213 (4) | 0.5379 (4) | 0.2320 (3) | 0.1016 (14) | |
H25 | 0.9710 | 0.4920 | 0.2180 | 0.122* | |
N26 | 0.8111 (3) | 0.5186 (2) | 0.2523 (2) | 0.0870 (9) | |
O27 | 0.39089 (18) | 0.56043 (13) | 0.35918 (14) | 0.0669 (6) | |
C28 | 0.2791 (3) | 0.5774 (2) | 0.3393 (2) | 0.0714 (9) | |
O29 | 0.2194 (2) | 0.52914 (19) | 0.29822 (19) | 0.0917 (8) | |
C30 | 0.2427 (3) | 0.6634 (2) | 0.3762 (3) | 0.0942 (12) | |
H30A | 0.1630 | 0.6745 | 0.3612 | 0.141* | |
H30B | 0.2911 | 0.7088 | 0.3526 | 0.141* | |
H30C | 0.2507 | 0.6621 | 0.4387 | 0.141* | |
O31 | 0.4737 (3) | −0.15522 (14) | 0.49735 (16) | 0.0873 (8) | |
C32 | 0.5236 (5) | −0.2169 (2) | 0.4505 (3) | 0.1002 (14) | |
O33 | 0.5569 (5) | −0.2062 (2) | 0.3780 (2) | 0.1589 (18) | |
C34 | 0.5370 (5) | −0.3008 (2) | 0.5013 (3) | 0.1207 (18) | |
H34A | 0.5707 | −0.3448 | 0.4643 | 0.181* | |
H34B | 0.4621 | −0.3202 | 0.5212 | 0.181* | |
H34C | 0.5868 | −0.2910 | 0.5507 | 0.181* | |
O1W | 0.1749 (12) | 0.3897 (9) | 0.1665 (9) | 0.175 (5)* | 0.35 |
O2W | 0.871 (3) | 0.352 (2) | 0.203 (2) | 0.130 (10)* | 0.11 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0608 (19) | 0.0723 (19) | 0.0712 (18) | −0.0086 (17) | 0.0008 (15) | 0.0032 (16) |
C2 | 0.081 (2) | 0.0726 (19) | 0.079 (2) | −0.0151 (19) | −0.0008 (19) | 0.0047 (18) |
C3 | 0.092 (2) | 0.0595 (16) | 0.0631 (16) | −0.0085 (19) | −0.0080 (18) | 0.0009 (14) |
C4 | 0.075 (2) | 0.0632 (17) | 0.0706 (19) | 0.0019 (18) | −0.0027 (17) | 0.0026 (15) |
C5 | 0.0620 (17) | 0.0566 (15) | 0.0570 (15) | 0.0026 (15) | −0.0057 (15) | −0.0018 (13) |
C6 | 0.0576 (18) | 0.0598 (16) | 0.0693 (17) | 0.0083 (15) | 0.0000 (15) | −0.0058 (14) |
C7 | 0.0478 (15) | 0.0626 (16) | 0.0632 (16) | 0.0057 (14) | 0.0026 (14) | −0.0007 (14) |
C8 | 0.0483 (15) | 0.0582 (15) | 0.0495 (13) | 0.0013 (14) | 0.0004 (12) | −0.0017 (12) |
C9 | 0.0504 (15) | 0.0593 (15) | 0.0513 (13) | 0.0023 (14) | 0.0019 (13) | −0.0031 (12) |
C10 | 0.0565 (17) | 0.0588 (15) | 0.0519 (14) | −0.0025 (14) | 0.0006 (13) | −0.0027 (12) |
C11 | 0.0517 (17) | 0.0668 (18) | 0.086 (2) | 0.0013 (15) | 0.0164 (16) | 0.0004 (16) |
C12 | 0.0486 (16) | 0.0664 (17) | 0.0777 (19) | 0.0091 (15) | 0.0093 (15) | 0.0011 (16) |
C13 | 0.0473 (15) | 0.0611 (15) | 0.0534 (14) | 0.0055 (14) | 0.0020 (12) | −0.0020 (12) |
C14 | 0.0429 (14) | 0.0600 (15) | 0.0517 (13) | 0.0033 (13) | −0.0005 (12) | −0.0028 (12) |
C15 | 0.0494 (16) | 0.0666 (16) | 0.0615 (15) | 0.0068 (14) | 0.0052 (14) | 0.0045 (14) |
C16 | 0.0507 (16) | 0.0652 (17) | 0.0522 (14) | 0.0067 (15) | −0.0004 (13) | 0.0080 (13) |
C17 | 0.0507 (15) | 0.0619 (16) | 0.0581 (15) | 0.0078 (15) | 0.0000 (14) | 0.0018 (13) |
C18 | 0.079 (2) | 0.0679 (17) | 0.0548 (15) | 0.0104 (17) | 0.0050 (16) | −0.0042 (14) |
C19 | 0.088 (2) | 0.0759 (19) | 0.0539 (15) | −0.0002 (19) | −0.0009 (16) | −0.0017 (15) |
C20 | 0.0591 (18) | 0.0684 (18) | 0.0636 (16) | 0.0068 (16) | −0.0006 (15) | 0.0130 (15) |
C21 | 0.0565 (19) | 0.089 (2) | 0.0602 (17) | 0.0029 (19) | −0.0044 (15) | 0.0239 (17) |
C22 | 0.069 (2) | 0.092 (3) | 0.092 (3) | −0.012 (2) | −0.007 (2) | 0.022 (2) |
C23 | 0.082 (3) | 0.124 (3) | 0.108 (3) | −0.031 (3) | −0.005 (3) | 0.028 (3) |
C24 | 0.062 (2) | 0.161 (4) | 0.099 (3) | −0.016 (3) | −0.002 (2) | 0.036 (3) |
C25 | 0.065 (2) | 0.143 (4) | 0.097 (3) | 0.014 (3) | 0.009 (2) | 0.031 (3) |
N26 | 0.0620 (18) | 0.112 (2) | 0.087 (2) | 0.0093 (18) | 0.0112 (16) | 0.0284 (19) |
O27 | 0.0571 (12) | 0.0636 (12) | 0.0799 (13) | 0.0137 (10) | 0.0028 (11) | 0.0013 (11) |
C28 | 0.057 (2) | 0.078 (2) | 0.079 (2) | 0.0141 (18) | 0.0128 (17) | 0.0119 (18) |
O29 | 0.0560 (13) | 0.1045 (19) | 0.115 (2) | 0.0191 (14) | −0.0070 (14) | −0.0035 (18) |
C30 | 0.088 (3) | 0.080 (2) | 0.115 (3) | 0.026 (2) | 0.030 (2) | 0.009 (2) |
O31 | 0.124 (2) | 0.0588 (12) | 0.0794 (14) | −0.0063 (14) | −0.0111 (16) | 0.0011 (12) |
C32 | 0.148 (4) | 0.061 (2) | 0.092 (3) | 0.004 (2) | −0.035 (3) | −0.008 (2) |
O33 | 0.279 (5) | 0.102 (2) | 0.096 (2) | 0.066 (3) | 0.019 (3) | −0.0030 (18) |
C34 | 0.172 (5) | 0.060 (2) | 0.130 (3) | −0.011 (3) | −0.047 (4) | 0.004 (2) |
C1—C2 | 1.521 (4) | C15—C16 | 1.514 (4) |
C1—C10 | 1.550 (4) | C15—H15A | 0.97 |
C1—H1A | 0.97 | C15—H15B | 0.97 |
C1—H1B | 0.97 | C16—C20 | 1.328 (4) |
C2—C3 | 1.504 (5) | C16—C17 | 1.520 (4) |
C2—H2A | 0.97 | C17—O27 | 1.443 (3) |
C2—H2B | 0.97 | C17—H17 | 0.98 |
C3—O31 | 1.464 (4) | C18—H18A | 0.96 |
C3—C4 | 1.508 (5) | C18—H18B | 0.96 |
C3—H3 | 0.98 | C18—H18C | 0.96 |
C4—C5 | 1.516 (4) | C19—H19A | 0.96 |
C4—H4A | 0.97 | C19—H19B | 0.96 |
C4—H4B | 0.97 | C19—H19C | 0.96 |
C5—C6 | 1.323 (4) | C20—C21 | 1.463 (4) |
C5—C10 | 1.523 (4) | C20—H20 | 0.93 |
C6—C7 | 1.491 (4) | C21—N26 | 1.342 (5) |
C6—H6 | 0.93 | C21—C22 | 1.381 (5) |
C7—C8 | 1.521 (4) | C22—C23 | 1.377 (6) |
C7—H7A | 0.97 | C22—H22 | 0.93 |
C7—H7B | 0.97 | C23—C24 | 1.365 (6) |
C8—C14 | 1.518 (4) | C23—H23 | 0.93 |
C8—C9 | 1.537 (4) | C24—C25 | 1.362 (7) |
C8—H8 | 0.98 | C24—H24 | 0.93 |
C9—C11 | 1.543 (4) | C25—N26 | 1.338 (5) |
C9—C10 | 1.552 (4) | C25—H25 | 0.93 |
C9—H9 | 0.98 | O27—C28 | 1.346 (4) |
C10—C19 | 1.545 (4) | C28—O29 | 1.187 (4) |
C11—C12 | 1.530 (4) | C28—C30 | 1.490 (5) |
C11—H11A | 0.97 | C30—H30A | 0.96 |
C11—H11B | 0.97 | C30—H30B | 0.96 |
C12—C13 | 1.520 (4) | C30—H30C | 0.96 |
C12—H12A | 0.97 | O31—C32 | 1.315 (5) |
C12—H12B | 0.97 | C32—O33 | 1.185 (6) |
C13—C17 | 1.532 (4) | C32—C34 | 1.507 (5) |
C13—C18 | 1.533 (4) | C34—H34A | 0.96 |
C13—C14 | 1.543 (4) | C34—H34B | 0.96 |
C14—C15 | 1.528 (4) | C34—H34C | 0.96 |
C14—H14 | 0.98 | ||
C2—C1—C10 | 115.0 (3) | C8—C14—C15 | 119.6 (2) |
C2—C1—H1A | 108.5 | C8—C14—C13 | 113.4 (2) |
C10—C1—H1A | 108.5 | C15—C14—C13 | 105.0 (2) |
C2—C1—H1B | 108.5 | C8—C14—H14 | 105.9 |
C10—C1—H1B | 108.5 | C15—C14—H14 | 105.9 |
H1A—C1—H1B | 107.5 | C13—C14—H14 | 105.9 |
C3—C2—C1 | 109.6 (3) | C16—C15—C14 | 104.5 (2) |
C3—C2—H2A | 109.8 | C16—C15—H15A | 110.9 |
C1—C2—H2A | 109.8 | C14—C15—H15A | 110.9 |
C3—C2—H2B | 109.8 | C16—C15—H15B | 110.9 |
C1—C2—H2B | 109.8 | C14—C15—H15B | 110.9 |
H2A—C2—H2B | 108.2 | H15A—C15—H15B | 108.9 |
O31—C3—C2 | 107.5 (3) | C20—C16—C15 | 129.7 (3) |
O31—C3—C4 | 108.8 (3) | C20—C16—C17 | 123.8 (3) |
C2—C3—C4 | 110.2 (2) | C15—C16—C17 | 106.4 (2) |
O31—C3—H3 | 110.1 | O27—C17—C16 | 110.4 (2) |
C2—C3—H3 | 110.1 | O27—C17—C13 | 114.9 (2) |
C4—C3—H3 | 110.1 | C16—C17—C13 | 103.8 (2) |
C3—C4—C5 | 111.1 (3) | O27—C17—H17 | 109.2 |
C3—C4—H4A | 109.4 | C16—C17—H17 | 109.2 |
C5—C4—H4A | 109.4 | C13—C17—H17 | 109.2 |
C3—C4—H4B | 109.4 | C13—C18—H18A | 109.5 |
C5—C4—H4B | 109.4 | C13—C18—H18B | 109.5 |
H4A—C4—H4B | 108.0 | H18A—C18—H18B | 109.5 |
C6—C5—C4 | 120.9 (3) | C13—C18—H18C | 109.5 |
C6—C5—C10 | 123.0 (3) | H18A—C18—H18C | 109.5 |
C4—C5—C10 | 116.0 (3) | H18B—C18—H18C | 109.5 |
C5—C6—C7 | 125.0 (3) | C10—C19—H19A | 109.5 |
C5—C6—H6 | 117.5 | C10—C19—H19B | 109.5 |
C7—C6—H6 | 117.5 | H19A—C19—H19B | 109.5 |
C6—C7—C8 | 112.9 (2) | C10—C19—H19C | 109.5 |
C6—C7—H7A | 109.0 | H19A—C19—H19C | 109.5 |
C8—C7—H7A | 109.0 | H19B—C19—H19C | 109.5 |
C6—C7—H7B | 109.0 | C16—C20—C21 | 128.3 (3) |
C8—C7—H7B | 109.0 | C16—C20—H20 | 115.8 |
H7A—C7—H7B | 107.8 | C21—C20—H20 | 115.8 |
C14—C8—C7 | 110.6 (2) | N26—C21—C22 | 121.4 (3) |
C14—C8—C9 | 109.5 (2) | N26—C21—C20 | 118.8 (3) |
C7—C8—C9 | 109.1 (2) | C22—C21—C20 | 119.8 (3) |
C14—C8—H8 | 109.2 | C23—C22—C21 | 120.1 (4) |
C7—C8—H8 | 109.2 | C23—C22—H22 | 120.0 |
C9—C8—H8 | 109.2 | C21—C22—H22 | 120.0 |
C8—C9—C11 | 112.9 (2) | C24—C23—C22 | 118.3 (4) |
C8—C9—C10 | 112.9 (2) | C24—C23—H23 | 120.8 |
C11—C9—C10 | 113.0 (2) | C22—C23—H23 | 120.8 |
C8—C9—H9 | 105.7 | C25—C24—C23 | 118.8 (4) |
C11—C9—H9 | 105.7 | C25—C24—H24 | 120.6 |
C10—C9—H9 | 105.7 | C23—C24—H24 | 120.6 |
C5—C10—C19 | 108.0 (3) | N26—C25—C24 | 124.1 (4) |
C5—C10—C1 | 107.9 (2) | N26—C25—H25 | 118.0 |
C19—C10—C1 | 110.0 (2) | C24—C25—H25 | 118.0 |
C5—C10—C9 | 110.0 (2) | C25—N26—C21 | 117.3 (4) |
C19—C10—C9 | 112.1 (2) | C28—O27—C17 | 117.8 (3) |
C1—C10—C9 | 108.7 (2) | O29—C28—O27 | 123.5 (3) |
C12—C11—C9 | 114.4 (2) | O29—C28—C30 | 125.9 (3) |
C12—C11—H11A | 108.7 | O27—C28—C30 | 110.6 (3) |
C9—C11—H11A | 108.7 | C28—C30—H30A | 109.5 |
C12—C11—H11B | 108.7 | C28—C30—H30B | 109.5 |
C9—C11—H11B | 108.7 | H30A—C30—H30B | 109.5 |
H11A—C11—H11B | 107.6 | C28—C30—H30C | 109.5 |
C13—C12—C11 | 110.5 (3) | H30A—C30—H30C | 109.5 |
C13—C12—H12A | 109.5 | H30B—C30—H30C | 109.5 |
C11—C12—H12A | 109.5 | C32—O31—C3 | 117.9 (3) |
C13—C12—H12B | 109.5 | O33—C32—O31 | 123.5 (4) |
C11—C12—H12B | 109.5 | O33—C32—C34 | 124.5 (5) |
H12A—C12—H12B | 108.1 | O31—C32—C34 | 112.0 (4) |
C12—C13—C17 | 116.4 (2) | C32—C34—H34A | 109.5 |
C12—C13—C18 | 111.3 (2) | C32—C34—H34B | 109.5 |
C17—C13—C18 | 109.1 (2) | H34A—C34—H34B | 109.5 |
C12—C13—C14 | 107.8 (2) | C32—C34—H34C | 109.5 |
C17—C13—C14 | 98.2 (2) | H34A—C34—H34C | 109.5 |
C18—C13—C14 | 113.4 (2) | H34B—C34—H34C | 109.5 |
C10—C1—C2—C3 | −57.1 (4) | C12—C13—C14—C8 | −62.5 (3) |
C1—C2—C3—O31 | 177.6 (2) | C17—C13—C14—C8 | 176.2 (2) |
C1—C2—C3—C4 | 59.2 (4) | C18—C13—C14—C8 | 61.2 (3) |
O31—C3—C4—C5 | −175.2 (2) | C12—C13—C14—C15 | 165.1 (2) |
C2—C3—C4—C5 | −57.6 (4) | C17—C13—C14—C15 | 43.9 (3) |
C3—C4—C5—C6 | −125.4 (3) | C18—C13—C14—C15 | −71.1 (3) |
C3—C4—C5—C10 | 53.4 (4) | C8—C14—C15—C16 | −155.3 (2) |
C4—C5—C6—C7 | −179.9 (3) | C13—C14—C15—C16 | −26.6 (3) |
C10—C5—C6—C7 | 1.3 (5) | C14—C15—C16—C20 | 172.9 (3) |
C5—C6—C7—C8 | 15.2 (4) | C14—C15—C16—C17 | −2.1 (3) |
C6—C7—C8—C14 | −164.9 (2) | C20—C16—C17—O27 | −21.7 (4) |
C6—C7—C8—C9 | −44.4 (3) | C15—C16—C17—O27 | 153.7 (2) |
C14—C8—C9—C11 | −48.3 (3) | C20—C16—C17—C13 | −145.3 (3) |
C7—C8—C9—C11 | −169.5 (2) | C15—C16—C17—C13 | 30.1 (3) |
C14—C8—C9—C10 | −178.0 (2) | C12—C13—C17—O27 | 80.0 (3) |
C7—C8—C9—C10 | 60.8 (3) | C18—C13—C17—O27 | −47.0 (3) |
C6—C5—C10—C19 | −109.6 (3) | C14—C13—C17—O27 | −165.3 (2) |
C4—C5—C10—C19 | 71.6 (3) | C12—C13—C17—C16 | −159.3 (2) |
C6—C5—C10—C1 | 131.5 (3) | C18—C13—C17—C16 | 73.6 (3) |
C4—C5—C10—C1 | −47.3 (3) | C14—C13—C17—C16 | −44.7 (3) |
C6—C5—C10—C9 | 13.1 (4) | C15—C16—C20—C21 | 5.6 (5) |
C4—C5—C10—C9 | −165.7 (2) | C17—C16—C20—C21 | 179.8 (3) |
C2—C1—C10—C5 | 49.4 (3) | C16—C20—C21—N26 | 13.4 (5) |
C2—C1—C10—C19 | −68.2 (3) | C16—C20—C21—C22 | −167.6 (3) |
C2—C1—C10—C9 | 168.7 (3) | N26—C21—C22—C23 | 1.2 (5) |
C8—C9—C10—C5 | −44.1 (3) | C20—C21—C22—C23 | −177.7 (3) |
C11—C9—C10—C5 | −173.8 (2) | C21—C22—C23—C24 | −0.5 (6) |
C8—C9—C10—C19 | 76.1 (3) | C22—C23—C24—C25 | −0.3 (7) |
C11—C9—C10—C19 | −53.6 (3) | C23—C24—C25—N26 | 0.5 (7) |
C8—C9—C10—C1 | −162.0 (2) | C24—C25—N26—C21 | 0.1 (6) |
C11—C9—C10—C1 | 68.3 (3) | C22—C21—N26—C25 | −1.0 (5) |
C8—C9—C11—C12 | 47.9 (4) | C20—C21—N26—C25 | 178.0 (3) |
C10—C9—C11—C12 | 177.5 (3) | C16—C17—O27—C28 | 147.5 (3) |
C9—C11—C12—C13 | −52.8 (4) | C13—C17—O27—C28 | −95.6 (3) |
C11—C12—C13—C17 | 166.8 (2) | C17—O27—C28—O29 | 0.1 (5) |
C11—C12—C13—C18 | −67.3 (3) | C17—O27—C28—C30 | 179.8 (2) |
C11—C12—C13—C14 | 57.7 (3) | C2—C3—O31—C32 | 154.3 (4) |
C7—C8—C14—C15 | −57.7 (3) | C4—C3—O31—C32 | −86.4 (4) |
C9—C8—C14—C15 | −178.0 (2) | C3—O31—C32—O33 | −1.3 (8) |
C7—C8—C14—C13 | 177.5 (2) | C3—O31—C32—C34 | 176.6 (3) |
C9—C8—C14—C13 | 57.3 (3) |