Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028340/hg2064sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028340/hg2064Isup2.hkl |
CCDC reference: 618219
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C32H52O2 | F(000) = 520 |
Mr = 468.74 | Dx = 1.085 Mg m−3 |
Monoclinic, P21 | Melting point: 422 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 11.660 (4) Å | Cell parameters from 1389 reflections |
b = 7.400 (3) Å | θ = 2.5–20.3° |
c = 16.632 (6) Å | µ = 0.07 mm−1 |
β = 91.654 (6)° | T = 298 K |
V = 1434.5 (9) Å3 | Prism, colourless |
Z = 2 | 0.58 × 0.41 × 0.19 mm |
Bruker SMART CCD area-detector diffractometer | 2735 independent reflections |
Radiation source: fine-focus sealed tube | 1529 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→13 |
Tmin = 0.963, Tmax = 0.988 | k = −8→8 |
7593 measured reflections | l = −19→17 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.192 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1093P)2] where P = (Fo2 + 2Fc2)/3 |
2735 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
Experimental. Spectroscopic analysis: 1H NMR (500 MHz, CDCl3, δ, p.p.m.): 5.13 (1H, t sept, J = 1.4 and 7.0 Hz, H24), 4.74 (1H, s, H21), 4.70 (1H, s, J = 1.5 Hz, H21), 4.49 (1H, dd, J = 5.5 and 11.3 Hz, H3), 2.04, 1.63, 1.61 (each 3H, s, –COCH3, H26 and H27), 0.98, 0.88, 0.87,0.86, 0.85 (each 3H, s), 0.83 (1H, m, H5); 13C NMR (125 MHz, CDCl3, δ, p.p.m.): 170.9 (–COCH3), 152.7 (C20), 131.3 (C25), 124.5 (C24), 107.5 (C21), 80.9 (C3), 55.9 (C5), 50.9 (C9), 49.4 (C14), 47.8 (C17), 45.3 (C13), 40.5 (C8), 38.8 (C22), 37.9 (C4), 37.1 (C10), 35.4 (C7), 34.2 (C1), 31.4 (C15), 28.9 (C23), 27.9 (C28), 27.1 (C2), 25.7 (C26), 24.9 (C16), 23.7 (C2), 21.4 (C11), 21.3 (–COCH3), 18.2 (C6), 17.7 (C27), 16.5 (C30), 16.3 (C19), 15.9 (C18), 15.6 (C29). |
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 | ||
O1 | 0.5647 (3) | 0.5536 (6) | 0.8636 (2) | 0.0684 (11) | |
O2 | 0.4546 (4) | 0.7930 (7) | 0.8332 (3) | 0.0951 (15) | |
C1 | 0.4915 (6) | 0.6872 (9) | 0.8819 (4) | 0.0706 (17) | |
C2 | 0.4648 (7) | 0.6839 (12) | 0.9690 (4) | 0.118 (3) | |
H2A | 0.5037 | 0.5840 | 0.9946 | 0.177* | |
H2B | 0.3835 | 0.6709 | 0.9748 | 0.177* | |
H2C | 0.4900 | 0.7947 | 0.9938 | 0.177* | |
C3 | 0.7177 (4) | 0.6243 (7) | 0.6692 (3) | 0.0523 (14) | |
H3A | 0.7826 | 0.7003 | 0.6566 | 0.063* | |
H3B | 0.6523 | 0.6654 | 0.6367 | 0.063* | |
C4 | 0.6911 (5) | 0.6477 (7) | 0.7579 (3) | 0.0575 (14) | |
H4A | 0.7577 | 0.6146 | 0.7909 | 0.069* | |
H4B | 0.6730 | 0.7732 | 0.7686 | 0.069* | |
C5 | 0.5909 (4) | 0.5300 (7) | 0.7787 (3) | 0.0512 (13) | |
H5 | 0.5240 | 0.5686 | 0.7461 | 0.061* | |
C6 | 0.6101 (4) | 0.3251 (8) | 0.7641 (3) | 0.0506 (13) | |
C7 | 0.6454 (4) | 0.3082 (7) | 0.6752 (3) | 0.0436 (12) | |
H7 | 0.5781 | 0.3513 | 0.6442 | 0.052* | |
C8 | 0.6594 (4) | 0.1125 (7) | 0.6482 (3) | 0.0510 (13) | |
H8A | 0.7321 | 0.0655 | 0.6688 | 0.061* | |
H8B | 0.5985 | 0.0393 | 0.6697 | 0.061* | |
C9 | 0.6553 (4) | 0.1014 (7) | 0.5571 (3) | 0.0511 (13) | |
H9A | 0.5798 | 0.1387 | 0.5375 | 0.061* | |
H9B | 0.6662 | −0.0235 | 0.5413 | 0.061* | |
C10 | 0.7468 (4) | 0.2195 (7) | 0.5167 (3) | 0.0431 (12) | |
C11 | 0.7429 (4) | 0.4135 (7) | 0.5526 (3) | 0.0412 (12) | |
H11 | 0.6670 | 0.4592 | 0.5359 | 0.049* | |
C12 | 0.7451 (4) | 0.4295 (7) | 0.6464 (3) | 0.0425 (12) | |
C13 | 0.8272 (4) | 0.5408 (8) | 0.5112 (3) | 0.0547 (14) | |
H13A | 0.8167 | 0.6625 | 0.5314 | 0.066* | |
H13B | 0.9050 | 0.5039 | 0.5255 | 0.066* | |
C14 | 0.8123 (4) | 0.5430 (7) | 0.4192 (3) | 0.0542 (14) | |
H14A | 0.7400 | 0.6002 | 0.4041 | 0.065* | |
H14B | 0.8737 | 0.6128 | 0.3962 | 0.065* | |
C15 | 0.8142 (4) | 0.3538 (7) | 0.3864 (3) | 0.0471 (13) | |
H15 | 0.8889 | 0.3021 | 0.4021 | 0.057* | |
C16 | 0.7222 (4) | 0.2327 (7) | 0.4236 (3) | 0.0446 (12) | |
C17 | 0.7350 (5) | 0.0577 (9) | 0.3742 (3) | 0.0664 (16) | |
H17A | 0.7921 | −0.0211 | 0.3993 | 0.080* | |
H17B | 0.6625 | −0.0065 | 0.3701 | 0.080* | |
C18 | 0.7729 (5) | 0.1186 (9) | 0.2908 (3) | 0.0710 (17) | |
H18A | 0.7128 | 0.0945 | 0.2507 | 0.085* | |
H18B | 0.8413 | 0.0535 | 0.2759 | 0.085* | |
C19 | 0.7980 (4) | 0.3242 (8) | 0.2952 (3) | 0.0563 (14) | |
H19 | 0.7294 | 0.3899 | 0.2764 | 0.068* | |
C20 | 0.6972 (5) | 0.2468 (8) | 0.8254 (3) | 0.0712 (17) | |
H20A | 0.7702 | 0.3046 | 0.8193 | 0.107* | |
H20B | 0.7050 | 0.1193 | 0.8166 | 0.107* | |
H20C | 0.6711 | 0.2675 | 0.8789 | 0.107* | |
C21 | 0.4943 (5) | 0.2331 (9) | 0.7756 (3) | 0.0729 (17) | |
H21A | 0.5020 | 0.1055 | 0.7670 | 0.109* | |
H21B | 0.4388 | 0.2815 | 0.7377 | 0.109* | |
H21C | 0.4695 | 0.2547 | 0.8293 | 0.109* | |
C22 | 0.8634 (4) | 0.3825 (9) | 0.6849 (3) | 0.0631 (16) | |
H22A | 0.8829 | 0.2601 | 0.6718 | 0.095* | |
H22B | 0.8606 | 0.3953 | 0.7422 | 0.095* | |
H22C | 0.9203 | 0.4627 | 0.6645 | 0.095* | |
C23 | 0.8653 (4) | 0.1265 (8) | 0.5334 (3) | 0.0599 (15) | |
H23A | 0.9247 | 0.1966 | 0.5095 | 0.090* | |
H23B | 0.8643 | 0.0074 | 0.5105 | 0.090* | |
H23C | 0.8799 | 0.1183 | 0.5903 | 0.090* | |
C24 | 0.6006 (4) | 0.3036 (9) | 0.4033 (3) | 0.0620 (15) | |
H24A | 0.5451 | 0.2269 | 0.4277 | 0.093* | |
H24B | 0.5878 | 0.3036 | 0.3460 | 0.093* | |
H24C | 0.5931 | 0.4244 | 0.4234 | 0.093* | |
C25 | 0.8967 (5) | 0.3793 (8) | 0.2451 (3) | 0.0618 (15) | |
C26 | 0.8634 (7) | 0.4438 (15) | 0.1623 (4) | 0.115 (3) | |
H26A | 0.8020 | 0.3686 | 0.1403 | 0.138* | |
H26B | 0.9285 | 0.4326 | 0.1276 | 0.138* | |
C27 | 0.8242 (10) | 0.6382 (19) | 0.1635 (7) | 0.181 (6) | |
H27A | 0.7542 | 0.6435 | 0.1935 | 0.218* | |
H27B | 0.8818 | 0.7074 | 0.1935 | 0.218* | |
C28 | 0.8037 (8) | 0.7249 (19) | 0.0903 (6) | 0.161 (5) | |
H28 | 0.7347 | 0.6907 | 0.0654 | 0.193* | |
C29 | 0.8598 (8) | 0.8431 (15) | 0.0489 (5) | 0.117 (3) | |
C30 | 0.9619 (11) | 0.941 (2) | 0.0785 (6) | 0.178 (5) | |
H30A | 0.9867 | 1.0228 | 0.0378 | 0.266* | |
H30B | 1.0221 | 0.8560 | 0.0911 | 0.266* | |
H30C | 0.9437 | 1.0074 | 0.1260 | 0.266* | |
C31 | 1.0030 (5) | 0.3742 (10) | 0.2672 (4) | 0.084 (2) | |
H31A | 1.0241 | 0.3337 | 0.3185 | 0.101* | |
H31B | 1.0589 | 0.4111 | 0.2320 | 0.101* | |
C32 | 0.8214 (8) | 0.895 (2) | −0.0327 (5) | 0.194 (6) | |
H32A | 0.8732 | 0.9829 | −0.0536 | 0.290* | |
H32B | 0.7457 | 0.9456 | −0.0312 | 0.290* | |
H32C | 0.8202 | 0.7902 | −0.0668 | 0.290* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.088 (2) | 0.066 (3) | 0.051 (2) | 0.004 (2) | 0.0175 (18) | −0.004 (2) |
O2 | 0.129 (4) | 0.069 (3) | 0.089 (3) | 0.021 (3) | 0.029 (3) | 0.004 (3) |
C1 | 0.097 (4) | 0.049 (4) | 0.067 (4) | −0.006 (4) | 0.028 (3) | −0.010 (3) |
C2 | 0.190 (8) | 0.086 (6) | 0.081 (5) | 0.014 (6) | 0.064 (5) | −0.012 (4) |
C3 | 0.053 (3) | 0.043 (3) | 0.061 (3) | −0.006 (3) | 0.005 (2) | −0.001 (3) |
C4 | 0.074 (3) | 0.047 (4) | 0.051 (3) | −0.002 (3) | 0.013 (3) | −0.002 (3) |
C5 | 0.063 (3) | 0.047 (4) | 0.044 (3) | −0.003 (3) | 0.005 (2) | 0.008 (3) |
C6 | 0.056 (3) | 0.045 (3) | 0.051 (3) | −0.002 (3) | 0.008 (2) | 0.010 (3) |
C7 | 0.046 (3) | 0.033 (3) | 0.052 (3) | −0.004 (2) | 0.004 (2) | 0.007 (2) |
C8 | 0.057 (3) | 0.042 (3) | 0.054 (3) | −0.003 (3) | 0.008 (2) | 0.007 (3) |
C9 | 0.064 (3) | 0.031 (3) | 0.059 (3) | −0.008 (3) | 0.008 (2) | 0.000 (3) |
C10 | 0.048 (3) | 0.034 (3) | 0.048 (3) | −0.002 (2) | 0.002 (2) | 0.003 (2) |
C11 | 0.036 (2) | 0.035 (3) | 0.053 (3) | −0.003 (2) | 0.002 (2) | 0.006 (2) |
C12 | 0.042 (3) | 0.037 (3) | 0.048 (3) | 0.000 (3) | 0.002 (2) | 0.002 (2) |
C13 | 0.063 (3) | 0.041 (3) | 0.061 (3) | −0.012 (3) | 0.018 (2) | 0.002 (3) |
C14 | 0.063 (3) | 0.038 (3) | 0.062 (3) | −0.008 (3) | 0.018 (2) | 0.001 (3) |
C15 | 0.049 (3) | 0.037 (3) | 0.055 (3) | −0.004 (2) | 0.009 (2) | 0.000 (2) |
C16 | 0.044 (3) | 0.037 (3) | 0.053 (3) | −0.003 (2) | 0.009 (2) | 0.004 (2) |
C17 | 0.079 (4) | 0.058 (4) | 0.063 (4) | −0.003 (3) | 0.007 (3) | −0.010 (3) |
C18 | 0.087 (4) | 0.060 (4) | 0.067 (4) | −0.007 (3) | 0.019 (3) | −0.008 (3) |
C19 | 0.055 (3) | 0.056 (4) | 0.059 (3) | 0.007 (3) | 0.013 (2) | 0.006 (3) |
C20 | 0.093 (4) | 0.056 (4) | 0.064 (4) | 0.011 (4) | 0.006 (3) | 0.020 (3) |
C21 | 0.081 (4) | 0.067 (4) | 0.072 (4) | −0.013 (4) | 0.030 (3) | 0.002 (3) |
C22 | 0.048 (3) | 0.074 (4) | 0.067 (3) | 0.001 (3) | 0.000 (2) | −0.002 (3) |
C23 | 0.064 (3) | 0.047 (4) | 0.069 (3) | 0.015 (3) | 0.010 (3) | 0.007 (3) |
C24 | 0.044 (3) | 0.080 (4) | 0.062 (3) | −0.003 (3) | 0.000 (2) | 0.003 (3) |
C25 | 0.060 (3) | 0.061 (4) | 0.065 (4) | 0.007 (3) | 0.013 (3) | 0.006 (3) |
C26 | 0.092 (5) | 0.163 (9) | 0.092 (5) | 0.020 (6) | 0.027 (4) | 0.054 (6) |
C27 | 0.185 (10) | 0.178 (12) | 0.184 (11) | 0.099 (10) | 0.069 (8) | 0.098 (9) |
C28 | 0.138 (8) | 0.226 (14) | 0.120 (7) | 0.036 (10) | 0.021 (6) | 0.067 (9) |
C29 | 0.119 (6) | 0.138 (9) | 0.098 (6) | 0.030 (6) | 0.041 (5) | 0.046 (6) |
C30 | 0.225 (12) | 0.152 (11) | 0.155 (10) | −0.027 (11) | −0.001 (9) | 0.030 (8) |
C31 | 0.073 (4) | 0.100 (6) | 0.081 (4) | 0.004 (4) | 0.026 (3) | 0.009 (4) |
C32 | 0.147 (7) | 0.317 (19) | 0.118 (8) | 0.024 (11) | 0.008 (6) | 0.084 (10) |
O1—C1 | 1.346 (7) | C16—C17 | 1.542 (8) |
O1—C5 | 1.462 (5) | C17—C18 | 1.537 (8) |
O2—C1 | 1.197 (7) | C17—H17A | 0.9700 |
C1—C2 | 1.492 (8) | C17—H17B | 0.9700 |
C2—H2A | 0.9600 | C18—C19 | 1.550 (9) |
C2—H2B | 0.9600 | C18—H18A | 0.9700 |
C2—H2C | 0.9600 | C18—H18B | 0.9700 |
C3—C4 | 1.526 (6) | C19—C25 | 1.498 (7) |
C3—C12 | 1.527 (7) | C19—H19 | 0.9800 |
C3—H3A | 0.9700 | C20—H20A | 0.9600 |
C3—H3B | 0.9700 | C20—H20B | 0.9600 |
C4—C5 | 1.506 (7) | C20—H20C | 0.9600 |
C4—H4A | 0.9700 | C21—H21A | 0.9600 |
C4—H4B | 0.9700 | C21—H21B | 0.9600 |
C5—C6 | 1.553 (8) | C21—H21C | 0.9600 |
C5—H5 | 0.9800 | C22—H22A | 0.9600 |
C6—C21 | 1.529 (7) | C22—H22B | 0.9600 |
C6—C20 | 1.532 (7) | C22—H22C | 0.9600 |
C6—C7 | 1.551 (6) | C23—H23A | 0.9600 |
C7—C8 | 1.526 (7) | C23—H23B | 0.9600 |
C7—C12 | 1.555 (6) | C23—H23C | 0.9600 |
C7—H7 | 0.9800 | C24—H24A | 0.9600 |
C8—C9 | 1.516 (6) | C24—H24B | 0.9600 |
C8—H8A | 0.9700 | C24—H24C | 0.9600 |
C8—H8B | 0.9700 | C25—C31 | 1.283 (7) |
C9—C10 | 1.548 (6) | C25—C26 | 1.498 (9) |
C9—H9A | 0.9700 | C26—C27 | 1.509 (15) |
C9—H9B | 0.9700 | C26—H26A | 0.9700 |
C10—C11 | 1.556 (7) | C26—H26B | 0.9700 |
C10—C23 | 1.561 (7) | C27—C28 | 1.391 (12) |
C10—C16 | 1.571 (6) | C27—H27A | 0.9700 |
C11—C13 | 1.539 (7) | C27—H27B | 0.9700 |
C11—C12 | 1.564 (6) | C28—C29 | 1.301 (13) |
C11—H11 | 0.9800 | C28—H28 | 0.9300 |
C12—C22 | 1.544 (6) | C29—C30 | 1.465 (13) |
C13—C14 | 1.536 (7) | C29—C32 | 1.468 (10) |
C13—H13A | 0.9700 | C30—H30A | 0.9600 |
C13—H13B | 0.9700 | C30—H30B | 0.9600 |
C14—C15 | 1.502 (7) | C30—H30C | 0.9600 |
C14—H14A | 0.9700 | C31—H31A | 0.9300 |
C14—H14B | 0.9700 | C31—H31B | 0.9300 |
C15—C19 | 1.539 (7) | C32—H32A | 0.9600 |
C15—C16 | 1.541 (6) | C32—H32B | 0.9600 |
C15—H15 | 0.9800 | C32—H32C | 0.9600 |
C16—C24 | 1.539 (6) | ||
C1—O1—C5 | 117.2 (4) | C24—C16—C17 | 105.8 (4) |
O2—C1—O1 | 123.1 (5) | C15—C16—C17 | 101.3 (4) |
O2—C1—C2 | 125.9 (7) | C24—C16—C10 | 112.2 (3) |
O1—C1—C2 | 111.1 (6) | C15—C16—C10 | 108.8 (4) |
C1—C2—H2A | 109.5 | C17—C16—C10 | 117.0 (4) |
C1—C2—H2B | 109.5 | C18—C17—C16 | 105.6 (5) |
H2A—C2—H2B | 109.5 | C18—C17—H17A | 110.6 |
C1—C2—H2C | 109.5 | C16—C17—H17A | 110.6 |
H2A—C2—H2C | 109.5 | C18—C17—H17B | 110.6 |
H2B—C2—H2C | 109.5 | C16—C17—H17B | 110.6 |
C4—C3—C12 | 113.4 (4) | H17A—C17—H17B | 108.8 |
C4—C3—H3A | 108.9 | C17—C18—C19 | 107.7 (5) |
C12—C3—H3A | 108.9 | C17—C18—H18A | 110.2 |
C4—C3—H3B | 108.9 | C19—C18—H18A | 110.2 |
C12—C3—H3B | 108.9 | C17—C18—H18B | 110.2 |
H3A—C3—H3B | 107.7 | C19—C18—H18B | 110.2 |
C5—C4—C3 | 109.8 (4) | H18A—C18—H18B | 108.5 |
C5—C4—H4A | 109.7 | C25—C19—C15 | 115.8 (5) |
C3—C4—H4A | 109.7 | C25—C19—C18 | 112.8 (5) |
C5—C4—H4B | 109.7 | C15—C19—C18 | 101.8 (4) |
C3—C4—H4B | 109.7 | C25—C19—H19 | 108.7 |
H4A—C4—H4B | 108.2 | C15—C19—H19 | 108.7 |
O1—C5—C4 | 109.8 (4) | C18—C19—H19 | 108.7 |
O1—C5—C6 | 107.6 (4) | C6—C20—H20A | 109.5 |
C4—C5—C6 | 114.3 (4) | C6—C20—H20B | 109.5 |
O1—C5—H5 | 108.3 | H20A—C20—H20B | 109.5 |
C4—C5—H5 | 108.3 | C6—C20—H20C | 109.5 |
C6—C5—H5 | 108.3 | H20A—C20—H20C | 109.5 |
C21—C6—C20 | 108.6 (5) | H20B—C20—H20C | 109.5 |
C21—C6—C7 | 110.0 (4) | C6—C21—H21A | 109.5 |
C20—C6—C7 | 114.5 (4) | C6—C21—H21B | 109.5 |
C21—C6—C5 | 106.4 (4) | H21A—C21—H21B | 109.5 |
C20—C6—C5 | 111.2 (4) | C6—C21—H21C | 109.5 |
C7—C6—C5 | 105.8 (4) | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 113.0 (4) | H21B—C21—H21C | 109.5 |
C8—C7—C12 | 111.7 (4) | C12—C22—H22A | 109.5 |
C6—C7—C12 | 117.9 (4) | C12—C22—H22B | 109.5 |
C8—C7—H7 | 104.2 | H22A—C22—H22B | 109.5 |
C6—C7—H7 | 104.2 | C12—C22—H22C | 109.5 |
C12—C7—H7 | 104.2 | H22A—C22—H22C | 109.5 |
C9—C8—C7 | 110.2 (4) | H22B—C22—H22C | 109.5 |
C9—C8—H8A | 109.6 | C10—C23—H23A | 109.5 |
C7—C8—H8A | 109.6 | C10—C23—H23B | 109.5 |
C9—C8—H8B | 109.6 | H23A—C23—H23B | 109.5 |
C7—C8—H8B | 109.6 | C10—C23—H23C | 109.5 |
H8A—C8—H8B | 108.1 | H23A—C23—H23C | 109.5 |
C8—C9—C10 | 113.6 (4) | H23B—C23—H23C | 109.5 |
C8—C9—H9A | 108.8 | C16—C24—H24A | 109.5 |
C10—C9—H9A | 108.8 | C16—C24—H24B | 109.5 |
C8—C9—H9B | 108.8 | H24A—C24—H24B | 109.5 |
C10—C9—H9B | 108.8 | C16—C24—H24C | 109.5 |
H9A—C9—H9B | 107.7 | H24A—C24—H24C | 109.5 |
C9—C10—C11 | 109.1 (4) | H24B—C24—H24C | 109.5 |
C9—C10—C23 | 107.0 (4) | C31—C25—C19 | 125.7 (5) |
C11—C10—C23 | 112.0 (4) | C31—C25—C26 | 119.7 (5) |
C9—C10—C16 | 110.8 (4) | C19—C25—C26 | 114.5 (5) |
C11—C10—C16 | 108.3 (4) | C25—C26—C27 | 111.2 (8) |
C23—C10—C16 | 109.8 (4) | C25—C26—H26A | 109.4 |
C13—C11—C10 | 111.5 (4) | C27—C26—H26A | 109.4 |
C13—C11—C12 | 114.0 (4) | C25—C26—H26B | 109.4 |
C10—C11—C12 | 116.9 (4) | C27—C26—H26B | 109.4 |
C13—C11—H11 | 104.2 | H26A—C26—H26B | 108.0 |
C10—C11—H11 | 104.2 | C28—C27—C26 | 118.1 (11) |
C12—C11—H11 | 104.2 | C28—C27—H27A | 107.8 |
C3—C12—C22 | 107.5 (4) | C26—C27—H27A | 107.8 |
C3—C12—C7 | 107.8 (4) | C28—C27—H27B | 107.8 |
C22—C12—C7 | 114.2 (4) | C26—C27—H27B | 107.8 |
C3—C12—C11 | 108.7 (4) | H27A—C27—H27B | 107.1 |
C22—C12—C11 | 112.7 (4) | C29—C28—C27 | 134.2 (12) |
C7—C12—C11 | 105.8 (3) | C29—C28—H28 | 112.9 |
C14—C13—C11 | 113.3 (4) | C27—C28—H28 | 112.9 |
C14—C13—H13A | 108.9 | C28—C29—C30 | 124.7 (10) |
C11—C13—H13A | 108.9 | C28—C29—C32 | 121.4 (11) |
C14—C13—H13B | 108.9 | C30—C29—C32 | 113.9 (9) |
C11—C13—H13B | 108.9 | C29—C30—H30A | 109.5 |
H13A—C13—H13B | 107.7 | C29—C30—H30B | 109.5 |
C15—C14—C13 | 110.4 (4) | H30A—C30—H30B | 109.5 |
C15—C14—H14A | 109.6 | C29—C30—H30C | 109.5 |
C13—C14—H14A | 109.6 | H30A—C30—H30C | 109.5 |
C15—C14—H14B | 109.6 | H30B—C30—H30C | 109.5 |
C13—C14—H14B | 109.6 | C25—C31—H31A | 120.0 |
H14A—C14—H14B | 108.1 | C25—C31—H31B | 120.0 |
C14—C15—C19 | 119.2 (4) | H31A—C31—H31B | 120.0 |
C14—C15—C16 | 112.3 (4) | C29—C32—H32A | 109.5 |
C19—C15—C16 | 104.2 (4) | C29—C32—H32B | 109.5 |
C14—C15—H15 | 106.9 | H32A—C32—H32B | 109.5 |
C19—C15—H15 | 106.9 | C29—C32—H32C | 109.5 |
C16—C15—H15 | 106.9 | H32A—C32—H32C | 109.5 |
C24—C16—C15 | 111.2 (4) | H32B—C32—H32C | 109.5 |
C5—O1—C1—O2 | −5.4 (8) | C10—C11—C12—C22 | 72.0 (5) |
C5—O1—C1—C2 | 175.8 (5) | C13—C11—C12—C7 | 173.5 (4) |
C12—C3—C4—C5 | −57.8 (5) | C10—C11—C12—C7 | −53.5 (4) |
C1—O1—C5—C4 | 87.7 (5) | C10—C11—C13—C14 | 53.1 (5) |
C1—O1—C5—C6 | −146.9 (4) | C12—C11—C13—C14 | −171.6 (4) |
C3—C4—C5—O1 | −179.6 (4) | C11—C13—C14—C15 | −51.8 (5) |
C3—C4—C5—C6 | 59.0 (5) | C13—C14—C15—C19 | 178.8 (3) |
O1—C5—C6—C21 | 66.7 (5) | C13—C14—C15—C16 | 56.4 (5) |
C4—C5—C6—C21 | −170.5 (4) | C14—C15—C16—C24 | 62.7 (5) |
O1—C5—C6—C20 | −51.6 (5) | C19—C15—C16—C24 | −68.0 (4) |
C4—C5—C6—C20 | 71.2 (5) | C14—C15—C16—C17 | 174.5 (4) |
O1—C5—C6—C7 | −176.5 (3) | C19—C15—C16—C17 | 43.8 (4) |
C4—C5—C6—C7 | −53.7 (5) | C14—C15—C16—C10 | −61.5 (5) |
C21—C6—C7—C8 | −61.0 (5) | C19—C15—C16—C10 | 167.8 (3) |
C20—C6—C7—C8 | 61.2 (5) | C9—C10—C16—C24 | 55.9 (5) |
C5—C6—C7—C8 | −175.7 (4) | C11—C10—C16—C24 | −63.8 (5) |
C21—C6—C7—C12 | 166.0 (4) | C23—C10—C16—C24 | 173.4 (4) |
C20—C6—C7—C12 | −71.9 (5) | C9—C10—C16—C15 | 179.2 (4) |
C5—C6—C7—C12 | 51.2 (5) | C11—C10—C16—C15 | 59.5 (4) |
C6—C7—C8—C9 | 161.8 (3) | C23—C10—C16—C15 | −63.3 (5) |
C12—C7—C8—C9 | −62.3 (5) | C9—C10—C16—C17 | −66.7 (5) |
C7—C8—C9—C10 | 56.8 (5) | C11—C10—C16—C17 | 173.5 (4) |
C8—C9—C10—C11 | −49.0 (5) | C23—C10—C16—C17 | 50.7 (5) |
C8—C9—C10—C23 | 72.5 (5) | C24—C16—C17—C18 | 84.5 (4) |
C8—C9—C10—C16 | −168.1 (4) | C15—C16—C17—C18 | −31.2 (5) |
C9—C10—C11—C13 | −176.9 (3) | C10—C16—C17—C18 | −149.5 (4) |
C23—C10—C11—C13 | 65.1 (5) | C16—C17—C18—C19 | 7.8 (5) |
C16—C10—C11—C13 | −56.1 (4) | C14—C15—C19—C25 | 71.4 (6) |
C9—C10—C11—C12 | 49.2 (5) | C16—C15—C19—C25 | −162.3 (4) |
C23—C10—C11—C12 | −68.7 (4) | C14—C15—C19—C18 | −165.2 (4) |
C16—C10—C11—C12 | 170.1 (3) | C16—C15—C19—C18 | −38.9 (5) |
C4—C3—C12—C22 | −71.3 (4) | C17—C18—C19—C25 | 144.3 (4) |
C4—C3—C12—C7 | 52.6 (5) | C17—C18—C19—C15 | 18.9 (5) |
C4—C3—C12—C11 | 167.1 (3) | C15—C19—C25—C31 | 32.0 (8) |
C8—C7—C12—C3 | 174.7 (4) | C18—C19—C25—C31 | −85.6 (7) |
C6—C7—C12—C3 | −51.5 (5) | C15—C19—C25—C26 | −148.2 (5) |
C8—C7—C12—C22 | −65.8 (5) | C18—C19—C25—C26 | 94.2 (7) |
C6—C7—C12—C22 | 68.0 (5) | C31—C25—C26—C27 | −99.4 (8) |
C8—C7—C12—C11 | 58.3 (4) | C19—C25—C26—C27 | 80.9 (8) |
C6—C7—C12—C11 | −167.9 (4) | C25—C26—C27—C28 | 172.1 (8) |
C13—C11—C12—C3 | 57.9 (5) | C26—C27—C28—C29 | −102.1 (18) |
C10—C11—C12—C3 | −169.2 (3) | C27—C28—C29—C30 | −10 (2) |
C13—C11—C12—C22 | −60.9 (5) | C27—C28—C29—C32 | 170.6 (12) |