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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- H-atom completeness 98%
- Disorder in solvent or counterion
- R factor = 0.040
- wR factor = 0.113
- Data-to-parameter ratio = 7.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.89 From the CIF: _reflns_number_total 2472 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2758 Completeness (_total/calc) 89.63% Alert B: < 90% complete (theta max?)
Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 23.00 Perc. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C29 H37.92 N1 O4.46 Atom count from the _atom_site data: C29 H37 N1 O4.46 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C29 H37.92 N O4.46 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 116.00 116.00 0.00 H 151.68 148.00 3.68 N 4.00 4.00 0.00 O 17.84 17.84 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional? REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.89 From the CIF: _reflns_number_total 2472 Count of symmetry unique reflns 2758 Completeness (_total/calc) 89.63% 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 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.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
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) |