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
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.056
- wR factor = 0.192
- Data-to-parameter ratio = 8.9
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.70 Ratio PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.92 Ratio PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C29
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C27 PLAT412_ALERT_2_B Short Intra XH3 .. XHn H22A .. H23C .. 1.71 Ang. PLAT703_ALERT_1_B Torsion Calc 174.7(5), Rep 175.8(5), Dev.. 2.20 Sigma C5 -O1 -C1 -C2 1.555 1.555 1.555 1.555
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT362_ALERT_2_C Short C(sp3)-C(sp2) Bond C27 - C28 ... 1.39 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C32 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H20A .. H22B .. 1.81 Ang. PLAT703_ALERT_1_C Torsion Calc -171.2(4), Rep -170.5(4), Dev.. 1.75 Sigma C4 -C5 -C6 -C21 1.555 1.555 1.555 1.555 PLAT703_ALERT_1_C Torsion Calc 71.9(5), Rep 72.5(5), Dev.. 1.20 Sigma C8 -C9 -C10 -C23 1.555 1.555 1.555 1.555 PLAT703_ALERT_1_C Torsion Calc -70.6(5), Rep -71.3(4), Dev.. 1.40 Sigma C4 -C3 -C12 -C22 1.555 1.555 1.555 1.555 PLAT703_ALERT_1_C Torsion Calc -148.9(6), Rep -148.2(5), Dev.. 1.17 Sigma C15 -C19 -C25 -C26 1.555 1.555 1.555 1.555 PLAT703_ALERT_1_C Torsion Calc 172.8(13), Rep 170.6(12), Dev.. 1.69 Sigma C27 -C28 -C29 -C32 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 2735 Count of symmetry unique reflns 2744 Completeness (_total/calc) 99.67% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19 = . S
3 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 9 ALERT level G = General alerts; check 15 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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) |