Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014705/fl2115sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014705/fl2115Isup2.hkl |
CCDC reference: 647210
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: PLATON (Spek, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
C29H50O4 | F(000) = 512 |
Mr = 462.69 | Dx = 1.088 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.5418 Å |
a = 12.5293 (13) Å | Cell parameters from 22 reflections |
b = 8.6751 (5) Å | θ = 14.9–23.8° |
c = 14.0660 (16) Å | µ = 0.55 mm−1 |
β = 112.578 (12)° | T = 293 K |
V = 1411.7 (2) Å3 | Block, colourless |
Z = 2 | 0.37 × 0.29 × 0.22 mm |
Enraf–Nonius MACH3 diffractometer | 1490 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 74.6°, θmin = 3.4° |
ω–2θ scans | h = −15→15 |
Absorption correction: ψ scan (North et al., 1968) | k = −5→10 |
Tmin = 0.768, Tmax = 0.882 | l = −17→17 |
9973 measured reflections | 3 standard reflections every 180 min |
3074 independent reflections | intensity decay: 1% |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0837P)2] where P = (Fo2 + 2Fc2)/3 |
3074 reflections | (Δ/σ)max < 0.001 |
306 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
Experimental. IR (ATR, cm-1): 3485, 3407, 2938, 2875, 1707, 1471, 1380, 1360, 1264, 1027; 1H NMR (300 MHz, CDCl3): δ 0.67 (s, 3H, 18-H3), 1.18 (s, 3H, 19-H3), 2.02 (s, 3H, CH3CO), 3.54 (br s, 1H, 6α-H), 5.15 (m, 1H, 3α-H); 13C NMR (75.5 MHz, CDCl3): δ 71.2 (C3), 75.6 (C5), 76.1 (C6), 170.9 (COO). |
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 | ||
C10 | 0.3880 (3) | 0.5924 (5) | 0.7835 (3) | 0.0566 (10) | |
C9 | 0.2596 (3) | 0.6440 (5) | 0.7277 (3) | 0.0579 (11) | |
H9 | 0.2612 | 0.7548 | 0.7147 | 0.069* | |
C5 | 0.4407 (3) | 0.6848 (5) | 0.8859 (3) | 0.0565 (11) | |
C14 | 0.0661 (3) | 0.6753 (5) | 0.7377 (3) | 0.0581 (11) | |
H14 | 0.0698 | 0.7827 | 0.7175 | 0.070* | |
C4 | 0.5692 (3) | 0.6444 (5) | 0.9435 (3) | 0.0633 (12) | |
H4A | 0.6004 | 0.7045 | 1.0064 | 0.076* | |
H4B | 0.5762 | 0.5362 | 0.9624 | 0.076* | |
O3 | 0.4327 (2) | 0.8441 (4) | 0.8559 (2) | 0.0734 (9) | |
H31 | 0.4767 | 0.8956 | 0.9038 | 0.110* | |
C3 | 0.6378 (3) | 0.6760 (6) | 0.8788 (3) | 0.0683 (12) | |
H3 | 0.6400 | 0.7873 | 0.8679 | 0.082* | |
C13 | 0.0044 (3) | 0.5839 (6) | 0.6363 (3) | 0.0575 (11) | |
C6 | 0.3728 (3) | 0.6698 (5) | 0.9546 (3) | 0.0621 (12) | |
H6 | 0.4055 | 0.7438 | 1.0111 | 0.075* | |
O1 | 0.7560 (2) | 0.6181 (4) | 0.9323 (2) | 0.0817 (10) | |
C8 | 0.1903 (3) | 0.6242 (5) | 0.7962 (3) | 0.0591 (11) | |
H8 | 0.1898 | 0.5144 | 0.8124 | 0.071* | |
C1 | 0.4602 (3) | 0.6307 (6) | 0.7192 (3) | 0.0740 (14) | |
H1A | 0.4512 | 0.7393 | 0.7014 | 0.089* | |
H1B | 0.4306 | 0.5721 | 0.6556 | 0.089* | |
O4 | 0.3847 (3) | 0.5199 (4) | 0.9995 (2) | 0.0692 (9) | |
H41 | 0.3745 | 0.4544 | 0.9548 | 0.104* | |
C15 | −0.0182 (3) | 0.6720 (7) | 0.7907 (3) | 0.0721 (13) | |
H15A | −0.0088 | 0.7622 | 0.8338 | 0.087* | |
H15B | −0.0070 | 0.5804 | 0.8329 | 0.087* | |
C17 | −0.1188 (3) | 0.6588 (6) | 0.6004 (3) | 0.0634 (12) | |
H17 | −0.1124 | 0.7641 | 0.5779 | 0.076* | |
C18 | −0.0013 (4) | 0.4125 (5) | 0.6577 (3) | 0.0701 (13) | |
H18A | 0.0756 | 0.3718 | 0.6886 | 0.105* | |
H18B | −0.0425 | 0.3595 | 0.5942 | 0.105* | |
H18C | −0.0407 | 0.3983 | 0.7037 | 0.105* | |
O2 | 0.8132 (3) | 0.8428 (6) | 1.0146 (3) | 0.1182 (16) | |
C11 | 0.2003 (3) | 0.5675 (7) | 0.6228 (3) | 0.0723 (13) | |
H11A | 0.2065 | 0.4565 | 0.6315 | 0.087* | |
H11B | 0.2406 | 0.5968 | 0.5788 | 0.087* | |
C7 | 0.2468 (3) | 0.7125 (6) | 0.8972 (3) | 0.0636 (12) | |
H7A | 0.2413 | 0.8221 | 0.8827 | 0.076* | |
H7B | 0.2046 | 0.6915 | 0.9409 | 0.076* | |
C12 | 0.0710 (3) | 0.6116 (6) | 0.5688 (3) | 0.0713 (14) | |
H12A | 0.0652 | 0.7196 | 0.5497 | 0.086* | |
H12B | 0.0367 | 0.5516 | 0.5062 | 0.086* | |
C19 | 0.3929 (4) | 0.4166 (5) | 0.8005 (3) | 0.0694 (13) | |
H19A | 0.3848 | 0.3652 | 0.7377 | 0.104* | |
H19B | 0.3313 | 0.3858 | 0.8209 | 0.104* | |
H19C | 0.4658 | 0.3894 | 0.8535 | 0.104* | |
C2 | 0.5899 (3) | 0.5947 (8) | 0.7759 (3) | 0.0818 (15) | |
H2A | 0.6005 | 0.4844 | 0.7864 | 0.098* | |
H2B | 0.6317 | 0.6278 | 0.7341 | 0.098* | |
C29 | 0.9459 (3) | 0.6315 (8) | 1.0524 (4) | 0.113 (2) | |
H29A | 0.9445 | 0.5782 | 1.1117 | 0.170* | |
H29B | 1.0071 | 0.7061 | 1.0736 | 0.170* | |
H29C | 0.9585 | 0.5588 | 1.0063 | 0.170* | |
C16 | −0.1390 (3) | 0.6709 (7) | 0.7022 (3) | 0.0810 (14) | |
H16A | −0.1806 | 0.7649 | 0.7031 | 0.097* | |
H16B | −0.1838 | 0.5837 | 0.7093 | 0.097* | |
C20 | −0.2195 (3) | 0.5809 (6) | 0.5137 (3) | 0.0694 (12) | |
H20 | −0.2275 | 0.4764 | 0.5366 | 0.083* | |
C28 | 0.8315 (4) | 0.7125 (9) | 0.9981 (4) | 0.0876 (17) | |
C22 | −0.3336 (3) | 0.6665 (7) | 0.4935 (3) | 0.0789 (14) | |
H22A | −0.3434 | 0.6783 | 0.5582 | 0.095* | |
H22B | −0.3285 | 0.7689 | 0.4678 | 0.095* | |
C24 | −0.5528 (3) | 0.6619 (8) | 0.4070 (4) | 0.0977 (19) | |
H24A | −0.5520 | 0.7682 | 0.3858 | 0.117* | |
H24B | −0.5580 | 0.6627 | 0.4740 | 0.117* | |
C21 | −0.1986 (4) | 0.5667 (8) | 0.4137 (3) | 0.0850 (16) | |
H21A | −0.1325 | 0.5022 | 0.4251 | 0.127* | |
H21B | −0.1848 | 0.6670 | 0.3920 | 0.127* | |
H21C | −0.2653 | 0.5218 | 0.3612 | 0.127* | |
C25 | −0.6606 (3) | 0.5814 (8) | 0.3294 (4) | 0.0902 (16) | |
H25 | −0.6522 | 0.4705 | 0.3438 | 0.108* | |
C23 | −0.4400 (3) | 0.5856 (7) | 0.4167 (4) | 0.0916 (16) | |
H23A | −0.4347 | 0.5846 | 0.3497 | 0.110* | |
H23B | −0.4405 | 0.4795 | 0.4382 | 0.110* | |
C27 | −0.6714 (5) | 0.6042 (11) | 0.2227 (5) | 0.141 (3) | |
H27A | −0.6929 | 0.7091 | 0.2027 | 0.211* | |
H27B | −0.7297 | 0.5362 | 0.1782 | 0.211* | |
H27C | −0.5988 | 0.5822 | 0.2175 | 0.211* | |
C26 | −0.7649 (4) | 0.6335 (13) | 0.3437 (5) | 0.159 (4) | |
H26A | −0.8290 | 0.5691 | 0.3044 | 0.239* | |
H26B | −0.7814 | 0.7383 | 0.3208 | 0.239* | |
H26C | −0.7526 | 0.6272 | 0.4153 | 0.239* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C10 | 0.051 (2) | 0.060 (3) | 0.054 (2) | 0.001 (2) | 0.0143 (18) | −0.002 (2) |
C9 | 0.054 (2) | 0.061 (3) | 0.052 (2) | −0.002 (2) | 0.0142 (18) | 0.002 (2) |
C5 | 0.051 (2) | 0.049 (3) | 0.061 (2) | −0.001 (2) | 0.0118 (18) | 0.003 (2) |
C14 | 0.054 (2) | 0.054 (3) | 0.057 (2) | 0.001 (2) | 0.0108 (18) | 0.002 (2) |
C4 | 0.050 (2) | 0.057 (3) | 0.070 (2) | 0.001 (2) | 0.0092 (19) | −0.003 (2) |
O3 | 0.0610 (17) | 0.054 (2) | 0.087 (2) | −0.0057 (15) | 0.0080 (14) | 0.0021 (17) |
C3 | 0.048 (2) | 0.072 (3) | 0.079 (3) | 0.005 (2) | 0.0173 (19) | 0.006 (3) |
C13 | 0.053 (2) | 0.059 (3) | 0.052 (2) | 0.000 (2) | 0.0108 (18) | 0.003 (2) |
C6 | 0.056 (2) | 0.057 (3) | 0.059 (2) | 0.002 (2) | 0.0073 (18) | −0.008 (2) |
O1 | 0.0483 (15) | 0.093 (3) | 0.092 (2) | 0.0044 (17) | 0.0135 (15) | −0.001 (2) |
C8 | 0.0491 (19) | 0.064 (3) | 0.053 (2) | 0.003 (2) | 0.0063 (17) | −0.002 (2) |
C1 | 0.054 (2) | 0.095 (4) | 0.072 (3) | −0.003 (3) | 0.023 (2) | 0.004 (3) |
O4 | 0.0654 (17) | 0.068 (2) | 0.0649 (17) | 0.0034 (17) | 0.0151 (15) | 0.0075 (16) |
C15 | 0.054 (2) | 0.086 (4) | 0.069 (3) | −0.001 (2) | 0.015 (2) | −0.012 (3) |
C17 | 0.054 (2) | 0.054 (3) | 0.066 (2) | 0.002 (2) | 0.0057 (19) | 0.001 (2) |
C18 | 0.063 (2) | 0.063 (3) | 0.072 (3) | −0.003 (2) | 0.014 (2) | −0.004 (3) |
O2 | 0.070 (2) | 0.105 (3) | 0.143 (3) | 0.011 (2) | 0.000 (2) | −0.039 (3) |
C11 | 0.055 (2) | 0.101 (4) | 0.056 (2) | −0.008 (3) | 0.0166 (19) | −0.006 (3) |
C7 | 0.051 (2) | 0.070 (3) | 0.062 (2) | 0.006 (2) | 0.0128 (18) | −0.003 (2) |
C12 | 0.060 (2) | 0.085 (4) | 0.055 (2) | −0.005 (3) | 0.0072 (19) | 0.004 (2) |
C19 | 0.065 (3) | 0.062 (3) | 0.068 (3) | 0.000 (2) | 0.011 (2) | −0.008 (2) |
C2 | 0.056 (2) | 0.110 (4) | 0.079 (3) | −0.005 (3) | 0.025 (2) | −0.001 (3) |
C29 | 0.054 (2) | 0.158 (7) | 0.107 (4) | 0.025 (4) | 0.008 (3) | 0.006 (4) |
C16 | 0.058 (2) | 0.093 (4) | 0.078 (3) | 0.009 (3) | 0.011 (2) | −0.014 (3) |
C20 | 0.056 (2) | 0.062 (3) | 0.072 (3) | −0.002 (2) | 0.004 (2) | −0.006 (3) |
C28 | 0.051 (3) | 0.108 (5) | 0.092 (4) | 0.004 (3) | 0.015 (2) | −0.007 (4) |
C22 | 0.051 (2) | 0.091 (4) | 0.079 (3) | 0.003 (3) | 0.006 (2) | −0.002 (3) |
C24 | 0.056 (2) | 0.133 (5) | 0.087 (3) | 0.009 (3) | 0.008 (2) | −0.019 (4) |
C21 | 0.065 (3) | 0.091 (4) | 0.078 (3) | 0.002 (3) | 0.004 (2) | −0.014 (3) |
C25 | 0.051 (2) | 0.101 (4) | 0.103 (4) | 0.010 (3) | 0.011 (2) | 0.004 (4) |
C23 | 0.056 (2) | 0.087 (4) | 0.108 (3) | −0.003 (3) | 0.005 (2) | −0.006 (4) |
C27 | 0.103 (4) | 0.203 (8) | 0.100 (4) | −0.027 (6) | 0.021 (3) | −0.049 (5) |
C26 | 0.072 (3) | 0.266 (11) | 0.135 (5) | 0.007 (6) | 0.034 (3) | −0.027 (7) |
C10—C1 | 1.540 (5) | O2—C28 | 1.194 (7) |
C10—C19 | 1.541 (6) | C11—C12 | 1.550 (6) |
C10—C5 | 1.558 (5) | C11—H11A | 0.9700 |
C10—C9 | 1.561 (5) | C11—H11B | 0.9700 |
C9—C11 | 1.526 (5) | C7—H7A | 0.9700 |
C9—C8 | 1.534 (5) | C7—H7B | 0.9700 |
C9—H9 | 0.9800 | C12—H12A | 0.9700 |
C5—O3 | 1.437 (5) | C12—H12B | 0.9700 |
C5—C6 | 1.518 (6) | C19—H19A | 0.9600 |
C5—C4 | 1.539 (5) | C19—H19B | 0.9600 |
C14—C15 | 1.508 (5) | C19—H19C | 0.9600 |
C14—C8 | 1.521 (5) | C2—H2A | 0.9700 |
C14—C13 | 1.554 (5) | C2—H2B | 0.9700 |
C14—H14 | 0.9800 | C29—C28 | 1.513 (7) |
C4—C3 | 1.497 (5) | C29—H29A | 0.9600 |
C4—H4A | 0.9700 | C29—H29B | 0.9600 |
C4—H4B | 0.9700 | C29—H29C | 0.9600 |
O3—H31 | 0.8200 | C16—H16A | 0.9700 |
C3—O1 | 1.468 (5) | C16—H16B | 0.9700 |
C3—C2 | 1.512 (6) | C20—C21 | 1.532 (6) |
C3—H3 | 0.9800 | C20—C22 | 1.538 (6) |
C13—C12 | 1.505 (5) | C20—H20 | 0.9800 |
C13—C18 | 1.524 (7) | C22—C23 | 1.526 (6) |
C13—C17 | 1.569 (5) | C22—H22A | 0.9700 |
C6—O4 | 1.428 (5) | C22—H22B | 0.9700 |
C6—C7 | 1.518 (5) | C24—C23 | 1.518 (7) |
C6—H6 | 0.9800 | C24—C25 | 1.540 (7) |
O1—C28 | 1.323 (7) | C24—H24A | 0.9700 |
C8—C7 | 1.528 (5) | C24—H24B | 0.9700 |
C8—H8 | 0.9800 | C21—H21A | 0.9600 |
C1—C2 | 1.542 (5) | C21—H21B | 0.9600 |
C1—H1A | 0.9700 | C21—H21C | 0.9600 |
C1—H1B | 0.9700 | C25—C27 | 1.468 (7) |
O4—H41 | 0.8200 | C25—C26 | 1.468 (7) |
C15—C16 | 1.547 (5) | C25—H25 | 0.9800 |
C15—H15A | 0.9700 | C23—H23A | 0.9700 |
C15—H15B | 0.9700 | C23—H23B | 0.9700 |
C17—C20 | 1.534 (5) | C27—H27A | 0.9600 |
C17—C16 | 1.550 (6) | C27—H27B | 0.9600 |
C17—H17 | 0.9800 | C27—H27C | 0.9600 |
C18—H18A | 0.9600 | C26—H26A | 0.9600 |
C18—H18B | 0.9600 | C26—H26B | 0.9600 |
C18—H18C | 0.9600 | C26—H26C | 0.9600 |
C1—C10—C19 | 107.9 (4) | C6—C7—C8 | 112.8 (3) |
C1—C10—C5 | 107.2 (3) | C6—C7—H7A | 109.0 |
C19—C10—C5 | 112.8 (3) | C8—C7—H7A | 109.0 |
C1—C10—C9 | 111.6 (3) | C6—C7—H7B | 109.0 |
C19—C10—C9 | 109.5 (4) | C8—C7—H7B | 109.0 |
C5—C10—C9 | 107.8 (3) | H7A—C7—H7B | 107.8 |
C11—C9—C8 | 112.1 (3) | C13—C12—C11 | 112.3 (3) |
C11—C9—C10 | 112.7 (3) | C13—C12—H12A | 109.1 |
C8—C9—C10 | 112.0 (3) | C11—C12—H12A | 109.1 |
C11—C9—H9 | 106.5 | C13—C12—H12B | 109.1 |
C8—C9—H9 | 106.5 | C11—C12—H12B | 109.1 |
C10—C9—H9 | 106.5 | H12A—C12—H12B | 107.9 |
O3—C5—C6 | 106.1 (3) | C10—C19—H19A | 109.5 |
O3—C5—C4 | 108.4 (3) | C10—C19—H19B | 109.5 |
C6—C5—C4 | 112.0 (3) | H19A—C19—H19B | 109.5 |
O3—C5—C10 | 105.4 (3) | C10—C19—H19C | 109.5 |
C6—C5—C10 | 113.7 (3) | H19A—C19—H19C | 109.5 |
C4—C5—C10 | 110.8 (3) | H19B—C19—H19C | 109.5 |
C15—C14—C8 | 119.5 (3) | C3—C2—C1 | 110.7 (4) |
C15—C14—C13 | 104.4 (3) | C3—C2—H2A | 109.5 |
C8—C14—C13 | 113.1 (3) | C1—C2—H2A | 109.5 |
C15—C14—H14 | 106.3 | C3—C2—H2B | 109.5 |
C8—C14—H14 | 106.3 | C1—C2—H2B | 109.5 |
C13—C14—H14 | 106.3 | H2A—C2—H2B | 108.1 |
C3—C4—C5 | 111.5 (3) | C28—C29—H29A | 109.5 |
C3—C4—H4A | 109.3 | C28—C29—H29B | 109.5 |
C5—C4—H4A | 109.3 | H29A—C29—H29B | 109.5 |
C3—C4—H4B | 109.3 | C28—C29—H29C | 109.5 |
C5—C4—H4B | 109.3 | H29A—C29—H29C | 109.5 |
H4A—C4—H4B | 108.0 | H29B—C29—H29C | 109.5 |
C5—O3—H31 | 109.5 | C15—C16—C17 | 106.7 (3) |
O1—C3—C4 | 109.1 (3) | C15—C16—H16A | 110.4 |
O1—C3—C2 | 106.4 (4) | C17—C16—H16A | 110.4 |
C4—C3—C2 | 112.8 (4) | C15—C16—H16B | 110.4 |
O1—C3—H3 | 109.5 | C17—C16—H16B | 110.4 |
C4—C3—H3 | 109.5 | H16A—C16—H16B | 108.6 |
C2—C3—H3 | 109.5 | C21—C20—C17 | 112.8 (4) |
C12—C13—C18 | 111.1 (4) | C21—C20—C22 | 110.1 (4) |
C12—C13—C14 | 107.3 (3) | C17—C20—C22 | 110.9 (4) |
C18—C13—C14 | 111.2 (3) | C21—C20—H20 | 107.6 |
C12—C13—C17 | 116.5 (3) | C17—C20—H20 | 107.6 |
C18—C13—C17 | 110.6 (4) | C22—C20—H20 | 107.6 |
C14—C13—C17 | 99.5 (3) | O2—C28—O1 | 125.7 (5) |
O4—C6—C5 | 111.7 (4) | O2—C28—C29 | 123.8 (6) |
O4—C6—C7 | 111.6 (4) | O1—C28—C29 | 110.5 (6) |
C5—C6—C7 | 111.3 (3) | C23—C22—C20 | 114.0 (4) |
O4—C6—H6 | 107.3 | C23—C22—H22A | 108.8 |
C5—C6—H6 | 107.3 | C20—C22—H22A | 108.8 |
C7—C6—H6 | 107.3 | C23—C22—H22B | 108.8 |
C28—O1—C3 | 117.1 (4) | C20—C22—H22B | 108.8 |
C14—C8—C7 | 111.6 (3) | H22A—C22—H22B | 107.7 |
C14—C8—C9 | 109.6 (3) | C23—C24—C25 | 113.5 (5) |
C7—C8—C9 | 110.9 (3) | C23—C24—H24A | 108.9 |
C14—C8—H8 | 108.2 | C25—C24—H24A | 108.9 |
C7—C8—H8 | 108.2 | C23—C24—H24B | 108.9 |
C9—C8—H8 | 108.2 | C25—C24—H24B | 108.9 |
C10—C1—C2 | 113.1 (3) | H24A—C24—H24B | 107.7 |
C10—C1—H1A | 109.0 | C20—C21—H21A | 109.5 |
C2—C1—H1A | 109.0 | C20—C21—H21B | 109.5 |
C10—C1—H1B | 109.0 | H21A—C21—H21B | 109.5 |
C2—C1—H1B | 109.0 | C20—C21—H21C | 109.5 |
H1A—C1—H1B | 107.8 | H21A—C21—H21C | 109.5 |
C6—O4—H41 | 109.5 | H21B—C21—H21C | 109.5 |
C14—C15—C16 | 104.9 (3) | C27—C25—C26 | 111.1 (5) |
C14—C15—H15A | 110.8 | C27—C25—C24 | 112.0 (5) |
C16—C15—H15A | 110.8 | C26—C25—C24 | 110.4 (5) |
C14—C15—H15B | 110.8 | C27—C25—H25 | 107.7 |
C16—C15—H15B | 110.8 | C26—C25—H25 | 107.7 |
H15A—C15—H15B | 108.8 | C24—C25—H25 | 107.7 |
C20—C17—C16 | 112.8 (3) | C24—C23—C22 | 113.2 (5) |
C20—C17—C13 | 118.7 (4) | C24—C23—H23A | 108.9 |
C16—C17—C13 | 102.7 (3) | C22—C23—H23A | 108.9 |
C20—C17—H17 | 107.3 | C24—C23—H23B | 108.9 |
C16—C17—H17 | 107.3 | C22—C23—H23B | 108.9 |
C13—C17—H17 | 107.3 | H23A—C23—H23B | 107.8 |
C13—C18—H18A | 109.5 | C25—C27—H27A | 109.5 |
C13—C18—H18B | 109.5 | C25—C27—H27B | 109.5 |
H18A—C18—H18B | 109.5 | H27A—C27—H27B | 109.5 |
C13—C18—H18C | 109.5 | C25—C27—H27C | 109.5 |
H18A—C18—H18C | 109.5 | H27A—C27—H27C | 109.5 |
H18B—C18—H18C | 109.5 | H27B—C27—H27C | 109.5 |
C9—C11—C12 | 113.3 (4) | C25—C26—H26A | 109.5 |
C9—C11—H11A | 108.9 | C25—C26—H26B | 109.5 |
C12—C11—H11A | 108.9 | H26A—C26—H26B | 109.5 |
C9—C11—H11B | 108.9 | C25—C26—H26C | 109.5 |
C12—C11—H11B | 108.9 | H26A—C26—H26C | 109.5 |
H11A—C11—H11B | 107.7 | H26B—C26—H26C | 109.5 |
C1—C10—C9—C11 | 59.3 (5) | C10—C9—C8—C7 | 56.6 (5) |
C19—C10—C9—C11 | −60.1 (5) | C19—C10—C1—C2 | −64.8 (5) |
C5—C10—C9—C11 | 176.8 (4) | C5—C10—C1—C2 | 57.0 (5) |
C1—C10—C9—C8 | −173.2 (4) | C9—C10—C1—C2 | 174.9 (4) |
C19—C10—C9—C8 | 67.4 (5) | C8—C14—C15—C16 | −159.7 (4) |
C5—C10—C9—C8 | −55.7 (4) | C13—C14—C15—C16 | −32.1 (5) |
C1—C10—C5—O3 | 59.5 (4) | C12—C13—C17—C20 | 78.3 (5) |
C19—C10—C5—O3 | 178.1 (4) | C18—C13—C17—C20 | −49.9 (5) |
C9—C10—C5—O3 | −60.8 (4) | C14—C13—C17—C20 | −166.9 (4) |
C1—C10—C5—C6 | 175.2 (4) | C12—C13—C17—C16 | −156.5 (4) |
C19—C10—C5—C6 | −66.1 (4) | C18—C13—C17—C16 | 75.4 (4) |
C9—C10—C5—C6 | 54.9 (4) | C14—C13—C17—C16 | −41.7 (4) |
C1—C10—C5—C4 | −57.6 (4) | C8—C9—C11—C12 | 49.7 (5) |
C19—C10—C5—C4 | 61.1 (5) | C10—C9—C11—C12 | 177.2 (4) |
C9—C10—C5—C4 | −177.9 (4) | O4—C6—C7—C8 | −72.7 (5) |
O3—C5—C4—C3 | −57.2 (5) | C5—C6—C7—C8 | 52.9 (5) |
C6—C5—C4—C3 | −173.8 (4) | C14—C8—C7—C6 | −177.0 (4) |
C10—C5—C4—C3 | 58.0 (5) | C9—C8—C7—C6 | −54.4 (5) |
C5—C4—C3—O1 | −173.2 (4) | C18—C13—C12—C11 | −65.7 (5) |
C5—C4—C3—C2 | −55.2 (5) | C14—C13—C12—C11 | 56.0 (5) |
C15—C14—C13—C12 | 167.8 (4) | C17—C13—C12—C11 | 166.3 (4) |
C8—C14—C13—C12 | −60.7 (5) | C9—C11—C12—C13 | −53.2 (6) |
C15—C14—C13—C18 | −70.6 (4) | O1—C3—C2—C1 | 172.4 (4) |
C8—C14—C13—C18 | 60.9 (5) | C4—C3—C2—C1 | 52.8 (6) |
C15—C14—C13—C17 | 46.1 (4) | C10—C1—C2—C3 | −55.1 (6) |
C8—C14—C13—C17 | 177.5 (4) | C14—C15—C16—C17 | 5.0 (6) |
O3—C5—C6—O4 | −173.4 (3) | C20—C17—C16—C15 | 152.4 (4) |
C4—C5—C6—O4 | −55.4 (4) | C13—C17—C16—C15 | 23.4 (5) |
C10—C5—C6—O4 | 71.2 (4) | C16—C17—C20—C21 | −179.1 (5) |
O3—C5—C6—C7 | 61.1 (4) | C13—C17—C20—C21 | −58.9 (6) |
C4—C5—C6—C7 | 179.1 (4) | C16—C17—C20—C22 | 56.9 (5) |
C10—C5—C6—C7 | −54.3 (5) | C13—C17—C20—C22 | 177.1 (4) |
C4—C3—O1—C28 | −87.4 (5) | C3—O1—C28—O2 | −3.4 (8) |
C2—C3—O1—C28 | 150.7 (4) | C3—O1—C28—C29 | 175.6 (4) |
C15—C14—C8—C7 | −54.5 (6) | C21—C20—C22—C23 | 61.0 (6) |
C13—C14—C8—C7 | −178.0 (4) | C17—C20—C22—C23 | −173.4 (4) |
C15—C14—C8—C9 | −177.8 (4) | C23—C24—C25—C27 | −70.7 (8) |
C13—C14—C8—C9 | 58.8 (5) | C23—C24—C25—C26 | 164.9 (6) |
C11—C9—C8—C14 | −51.9 (5) | C25—C24—C23—C22 | 179.8 (5) |
C10—C9—C8—C14 | −179.7 (4) | C20—C22—C23—C24 | 173.5 (5) |
C11—C9—C8—C7 | −175.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H31···O4i | 0.82 | 2.05 | 2.850 (4) | 164 |
Symmetry code: (i) −x+1, y+1/2, −z+2. |