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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.051
- wR factor = 0.153
- Data-to-parameter ratio = 10.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C25 PLAT414_ALERT_2_B Short Intra D-H..H-X H19B .. H41 .. 1.85 Ang. PLAT420_ALERT_2_B D-H Without Acceptor O4 - H41 ... ?
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.81 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.46 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 74.56 From the CIF: _reflns_number_total 3074 Count of symmetry unique reflns 3095 Completeness (_total/calc) 99.32% 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 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . R
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 13 ALERT level G = General alerts; check 13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: 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. |
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