Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018289/bh2018sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018289/bh2018Isup2.hkl |
CCDC reference: 602003
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.073
- wR factor = 0.239
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc. PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.84 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.49 Ratio PLAT420_ALERT_2_B D-H Without Acceptor >O6 - >H1 ... ?
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.676 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.90 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.68 e/A 3 PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 6179.00 Ang-3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C23
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 6 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 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C34H33NO5·0.5H2O | F(000) = 2312 |
Mr = 544.62 | Dx = 1.171 Mg m−3 |
Monoclinic, C2/c | Melting point = 471–473 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 25.094 (6) Å | Cell parameters from 1509 reflections |
b = 12.755 (3) Å | θ = 2.2–20.2° |
c = 19.891 (5) Å | µ = 0.08 mm−1 |
β = 103.926 (4)° | T = 298 K |
V = 6179 (3) Å3 | Block, red |
Z = 8 | 0.50 × 0.46 × 0.26 mm |
Bruker CCD area-detector diffractometer | 5381 independent reflections |
Radiation source: fine-focus sealed tube | 2112 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
φ and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→29 |
Tmin = 0.962, Tmax = 0.980 | k = −15→15 |
15711 measured reflections | l = −23→21 |
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)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.239 | w = 1/[σ2(Fo2) + (0.1027P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
5381 reflections | Δρmax = 0.68 e Å−3 |
378 parameters | Δρmin = −0.23 e Å−3 |
180 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0011 (3) |
Experimental. 1H NMR (DMSO-d6): δ 7.48–7.54 (m, 4H, ArH), 7.27 (d, 1H, ArH, J = 6.8 Hz), 7.18 (t, 1H, ArH, J = 7.4 Hz), 7.01 (t, 1H, ArH, J = 7.6 Hz), 6.59 (s, 2H, ArH), 5.19 (d, 1H, ArH, J = 7.6 Hz), 4.82 (s, 1H, CH), 3.76 (s, 6H, CH3), 3.61 (s, 3H, CH3), 2.50 (s, 3H, CH3), 2.48 (d, 1H, CH2, J = 16.4 Hz), 2.31 (d, 1H, CH2, J = 17.6 Hz), 2.10 (d, 1H, CH2, J = 16.4 Hz), 2.03 (d, 1H, CH2, J = 17.6 Hz), 0.97 (s, 3H, CH3) and 0.93 (s, 3H, CH3) |
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) | |
N1 | 0.80371 (13) | 0.5195 (3) | 0.35946 (16) | 0.0425 (9) | |
O1 | 0.61153 (13) | 0.5437 (3) | 0.33095 (16) | 0.0755 (11) | |
O2 | 0.72996 (12) | 0.7576 (3) | 0.18020 (15) | 0.0601 (9) | |
O3 | 0.71910 (19) | 0.3102 (3) | 0.08801 (19) | 0.0872 (12) | |
O4 | 0.61106 (17) | 0.2947 (3) | 0.05068 (18) | 0.0925 (13) | |
O5 | 0.54590 (18) | 0.4247 (4) | 0.1004 (2) | 0.1112 (15) | |
O6 | 1.0000 | 0.3007 (10) | 0.2500 | 0.210 (6) | 0.725 (10) |
H1 | 1.0087 | 0.3411 | 0.2204 | 0.252* | 0.725 (10) |
O6' | 1.0000 | 0.448 (3) | 0.2500 | 0.210 (6) | 0.275 (10) |
H2 | 1.0025 | 0.4884 | 0.2169 | 0.252* | 0.275 (10) |
C1 | 0.75220 (17) | 0.5035 (3) | 0.3699 (2) | 0.0411 (11) | |
C2 | 0.73784 (17) | 0.4512 (3) | 0.43060 (19) | 0.0411 (11) | |
C3 | 0.76821 (19) | 0.4018 (4) | 0.4890 (2) | 0.0535 (13) | |
H3 | 0.8061 | 0.3951 | 0.4968 | 0.064* | |
C4 | 0.7399 (2) | 0.3622 (4) | 0.5360 (2) | 0.0585 (13) | |
H4 | 0.7598 | 0.3287 | 0.5756 | 0.070* | |
C5 | 0.6847 (2) | 0.3704 (4) | 0.5265 (2) | 0.0599 (13) | |
H5 | 0.6673 | 0.3440 | 0.5591 | 0.072* | |
C6 | 0.6550 (2) | 0.4191 (4) | 0.4670 (2) | 0.0608 (14) | |
H6 | 0.6170 | 0.4240 | 0.4588 | 0.073* | |
C7 | 0.68140 (17) | 0.4599 (3) | 0.4207 (2) | 0.0445 (11) | |
C8 | 0.65950 (19) | 0.5183 (4) | 0.3545 (2) | 0.0496 (12) | |
C9 | 0.70627 (16) | 0.5402 (3) | 0.32543 (19) | 0.0411 (11) | |
C10 | 0.70595 (15) | 0.5906 (3) | 0.25808 (19) | 0.0412 (11) | |
H10 | 0.6823 | 0.6526 | 0.2534 | 0.049* | |
C11 | 0.76404 (16) | 0.6276 (3) | 0.26144 (19) | 0.0405 (11) | |
C12 | 0.77045 (18) | 0.7143 (3) | 0.2165 (2) | 0.0421 (11) | |
C13 | 0.82681 (16) | 0.7531 (3) | 0.2176 (2) | 0.0463 (12) | |
H13A | 0.8352 | 0.8117 | 0.2495 | 0.056* | |
H13B | 0.8271 | 0.7790 | 0.1718 | 0.056* | |
C14 | 0.87172 (17) | 0.6709 (4) | 0.2387 (2) | 0.0476 (12) | |
C15 | 0.86603 (16) | 0.6208 (4) | 0.3067 (2) | 0.0491 (12) | |
H15A | 0.8896 | 0.5596 | 0.3159 | 0.059* | |
H15B | 0.8790 | 0.6703 | 0.3441 | 0.059* | |
C16 | 0.80873 (16) | 0.5887 (3) | 0.30684 (19) | 0.0382 (10) | |
C17 | 0.85150 (16) | 0.4813 (4) | 0.4101 (2) | 0.0474 (12) | |
C18 | 0.87370 (19) | 0.5419 (4) | 0.4674 (2) | 0.0610 (13) | |
H18 | 0.8596 | 0.6081 | 0.4725 | 0.073* | |
C19 | 0.9173 (2) | 0.5022 (5) | 0.5170 (2) | 0.0726 (16) | |
H19 | 0.9325 | 0.5430 | 0.5556 | 0.087* | |
C20 | 0.9386 (2) | 0.4061 (5) | 0.5116 (3) | 0.0705 (15) | |
C21 | 0.91634 (19) | 0.3479 (4) | 0.4535 (3) | 0.0732 (15) | |
H21 | 0.9310 | 0.2822 | 0.4484 | 0.088* | |
C22 | 0.87260 (17) | 0.3842 (4) | 0.4021 (2) | 0.0588 (13) | |
H22 | 0.8580 | 0.3437 | 0.3631 | 0.071* | |
C23 | 0.9854 (2) | 0.3631 (6) | 0.5680 (3) | 0.109 (2) | |
H23A | 0.9958 | 0.4142 | 0.6042 | 0.163* | |
H23B | 1.0162 | 0.3478 | 0.5489 | 0.163* | |
H23C | 0.9736 | 0.3001 | 0.5866 | 0.163* | |
C24 | 0.68206 (17) | 0.5171 (3) | 0.1977 (2) | 0.0423 (11) | |
C25 | 0.71465 (19) | 0.4507 (4) | 0.1701 (2) | 0.0502 (12) | |
H25 | 0.7527 | 0.4537 | 0.1857 | 0.060* | |
C26 | 0.6907 (2) | 0.3792 (4) | 0.1188 (2) | 0.0577 (13) | |
C27 | 0.6344 (2) | 0.3732 (4) | 0.0966 (2) | 0.0666 (15) | |
C28 | 0.6018 (2) | 0.4398 (5) | 0.1250 (3) | 0.0708 (16) | |
C29 | 0.62586 (18) | 0.5123 (4) | 0.1736 (2) | 0.0580 (13) | |
H29 | 0.6039 | 0.5592 | 0.1905 | 0.070* | |
C30 | 0.7762 (3) | 0.3193 (5) | 0.1032 (4) | 0.109 (2) | |
H30A | 0.7909 | 0.2672 | 0.0778 | 0.164* | |
H30B | 0.7910 | 0.3091 | 0.1519 | 0.164* | |
H30C | 0.7860 | 0.3878 | 0.0902 | 0.164* | |
C31 | 0.6057 (18) | 0.3174 (16) | −0.0213 (10) | 0.087 (6) | 0.56 (6) |
H31A | 0.5894 | 0.2584 | −0.0487 | 0.130* | 0.56 (6) |
H31B | 0.6413 | 0.3311 | −0.0293 | 0.130* | 0.56 (6) |
H31C | 0.5827 | 0.3778 | −0.0341 | 0.130* | 0.56 (6) |
C31' | 0.5779 (19) | 0.333 (3) | −0.0163 (14) | 0.087 (7) | 0.44 (6) |
H31D | 0.5632 | 0.2749 | −0.0452 | 0.131* | 0.44 (6) |
H31E | 0.6007 | 0.3746 | −0.0386 | 0.131* | 0.44 (6) |
H31F | 0.5484 | 0.3759 | −0.0086 | 0.131* | 0.44 (6) |
C32 | 0.5112 (3) | 0.4824 (7) | 0.1355 (4) | 0.146 (3) | |
H32A | 0.4734 | 0.4668 | 0.1146 | 0.220* | |
H32B | 0.5175 | 0.5562 | 0.1318 | 0.220* | |
H32C | 0.5197 | 0.4626 | 0.1835 | 0.220* | |
C33 | 0.86638 (19) | 0.5878 (4) | 0.1818 (2) | 0.0673 (15) | |
H33A | 0.8310 | 0.5549 | 0.1740 | 0.101* | |
H33B | 0.8946 | 0.5359 | 0.1959 | 0.101* | |
H33C | 0.8702 | 0.6206 | 0.1397 | 0.101* | |
C34 | 0.92793 (18) | 0.7216 (4) | 0.2511 (3) | 0.0712 (15) | |
H34A | 0.9316 | 0.7735 | 0.2869 | 0.107* | |
H34B | 0.9320 | 0.7545 | 0.2092 | 0.107* | |
H34C | 0.9558 | 0.6691 | 0.2650 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.030 (2) | 0.056 (2) | 0.0381 (19) | 0.0003 (17) | 0.0034 (16) | 0.0114 (18) |
O1 | 0.035 (2) | 0.120 (3) | 0.073 (2) | 0.0171 (19) | 0.0162 (16) | 0.019 (2) |
O2 | 0.054 (2) | 0.071 (2) | 0.0538 (19) | 0.0135 (17) | 0.0104 (16) | 0.0178 (17) |
O3 | 0.110 (3) | 0.074 (3) | 0.086 (3) | −0.007 (2) | 0.038 (2) | −0.024 (2) |
O4 | 0.126 (3) | 0.075 (3) | 0.058 (2) | −0.034 (2) | −0.016 (2) | −0.001 (2) |
O5 | 0.063 (3) | 0.138 (4) | 0.109 (3) | −0.022 (3) | −0.026 (2) | −0.016 (3) |
O6 | 0.187 (11) | 0.159 (10) | 0.256 (13) | 0.000 | 0.001 (10) | 0.000 |
O6' | 0.187 (11) | 0.159 (10) | 0.256 (13) | 0.000 | 0.001 (10) | 0.000 |
C1 | 0.040 (3) | 0.043 (3) | 0.039 (2) | 0.002 (2) | 0.007 (2) | −0.003 (2) |
C2 | 0.050 (3) | 0.043 (3) | 0.032 (2) | −0.007 (2) | 0.012 (2) | −0.003 (2) |
C3 | 0.051 (3) | 0.063 (3) | 0.046 (3) | −0.006 (2) | 0.010 (2) | 0.007 (2) |
C4 | 0.071 (4) | 0.063 (4) | 0.042 (3) | −0.006 (3) | 0.015 (3) | 0.001 (2) |
C5 | 0.074 (4) | 0.063 (4) | 0.049 (3) | −0.009 (3) | 0.028 (3) | 0.000 (3) |
C6 | 0.054 (3) | 0.076 (4) | 0.058 (3) | 0.000 (3) | 0.026 (3) | −0.004 (3) |
C7 | 0.040 (3) | 0.054 (3) | 0.041 (3) | −0.001 (2) | 0.014 (2) | −0.006 (2) |
C8 | 0.039 (3) | 0.062 (3) | 0.047 (3) | 0.004 (2) | 0.011 (2) | −0.006 (2) |
C9 | 0.033 (2) | 0.053 (3) | 0.037 (2) | 0.005 (2) | 0.009 (2) | 0.002 (2) |
C10 | 0.030 (2) | 0.049 (3) | 0.043 (2) | 0.008 (2) | 0.0059 (19) | 0.004 (2) |
C11 | 0.036 (3) | 0.048 (3) | 0.037 (2) | 0.003 (2) | 0.0078 (19) | 0.002 (2) |
C12 | 0.047 (3) | 0.043 (3) | 0.036 (2) | 0.006 (2) | 0.010 (2) | −0.001 (2) |
C13 | 0.048 (3) | 0.049 (3) | 0.043 (2) | −0.001 (2) | 0.014 (2) | 0.007 (2) |
C14 | 0.042 (3) | 0.059 (3) | 0.043 (3) | −0.007 (2) | 0.014 (2) | 0.002 (2) |
C15 | 0.036 (3) | 0.062 (3) | 0.049 (3) | 0.002 (2) | 0.009 (2) | 0.008 (2) |
C16 | 0.037 (3) | 0.044 (3) | 0.033 (2) | 0.001 (2) | 0.0084 (19) | 0.003 (2) |
C17 | 0.031 (2) | 0.062 (3) | 0.046 (3) | −0.003 (2) | 0.003 (2) | 0.015 (2) |
C18 | 0.054 (3) | 0.072 (3) | 0.049 (3) | −0.008 (3) | −0.004 (2) | 0.006 (3) |
C19 | 0.061 (3) | 0.093 (4) | 0.053 (3) | −0.014 (3) | −0.007 (3) | 0.011 (3) |
C20 | 0.041 (3) | 0.095 (4) | 0.070 (3) | −0.002 (3) | 0.001 (3) | 0.034 (3) |
C21 | 0.046 (3) | 0.079 (4) | 0.092 (4) | 0.015 (3) | 0.010 (3) | 0.033 (3) |
C22 | 0.038 (3) | 0.063 (3) | 0.070 (3) | 0.005 (2) | 0.002 (2) | 0.013 (3) |
C23 | 0.059 (4) | 0.160 (6) | 0.096 (4) | 0.005 (4) | −0.005 (3) | 0.063 (4) |
C24 | 0.036 (3) | 0.050 (3) | 0.040 (2) | 0.002 (2) | 0.008 (2) | 0.006 (2) |
C25 | 0.047 (3) | 0.057 (3) | 0.045 (3) | −0.006 (3) | 0.008 (2) | 0.009 (2) |
C26 | 0.071 (4) | 0.055 (3) | 0.048 (3) | −0.004 (3) | 0.018 (3) | 0.002 (3) |
C27 | 0.078 (4) | 0.064 (4) | 0.046 (3) | −0.024 (3) | −0.006 (3) | 0.001 (3) |
C28 | 0.047 (3) | 0.085 (4) | 0.067 (3) | −0.011 (3) | −0.015 (3) | 0.007 (3) |
C29 | 0.036 (3) | 0.073 (4) | 0.057 (3) | 0.001 (2) | −0.004 (2) | 0.003 (3) |
C30 | 0.119 (6) | 0.083 (5) | 0.145 (6) | 0.004 (4) | 0.069 (5) | −0.025 (4) |
C31 | 0.111 (14) | 0.078 (9) | 0.057 (7) | 0.005 (10) | −0.009 (10) | −0.006 (6) |
C31' | 0.086 (15) | 0.106 (13) | 0.059 (9) | −0.009 (12) | −0.005 (11) | 0.021 (9) |
C32 | 0.057 (5) | 0.157 (8) | 0.202 (8) | 0.015 (5) | −0.014 (5) | −0.027 (7) |
C33 | 0.064 (3) | 0.079 (4) | 0.063 (3) | 0.008 (3) | 0.024 (3) | −0.006 (3) |
C34 | 0.046 (3) | 0.096 (4) | 0.074 (3) | −0.015 (3) | 0.019 (3) | 0.010 (3) |
N1—C1 | 1.373 (5) | C15—H15A | 0.9700 |
N1—C16 | 1.398 (5) | C15—H15B | 0.9700 |
N1—C17 | 1.452 (5) | C17—C22 | 1.371 (6) |
O1—C8 | 1.225 (5) | C17—C18 | 1.378 (6) |
O2—C12 | 1.227 (4) | C18—C19 | 1.381 (6) |
O3—C26 | 1.367 (6) | C18—H18 | 0.9300 |
O3—C30 | 1.396 (7) | C19—C20 | 1.353 (7) |
O4—C27 | 1.387 (5) | C19—H19 | 0.9300 |
O4—C31 | 1.43 (2) | C20—C21 | 1.374 (7) |
O4—C31' | 1.47 (3) | C20—C23 | 1.517 (6) |
O5—C28 | 1.383 (6) | C21—C22 | 1.387 (6) |
O5—C32 | 1.442 (8) | C21—H21 | 0.9300 |
O6—H1 | 0.8500 | C22—H22 | 0.9300 |
O6'—H2 | 0.8500 | C23—H23A | 0.9600 |
C1—C9 | 1.356 (5) | C23—H23B | 0.9600 |
C1—C2 | 1.497 (5) | C23—H23C | 0.9600 |
C2—C3 | 1.378 (5) | C24—C29 | 1.377 (5) |
C2—C7 | 1.387 (6) | C24—C25 | 1.380 (6) |
C3—C4 | 1.398 (6) | C25—C26 | 1.392 (6) |
C3—H3 | 0.9300 | C25—H25 | 0.9300 |
C4—C5 | 1.355 (6) | C26—C27 | 1.377 (7) |
C4—H4 | 0.9300 | C27—C28 | 1.390 (7) |
C5—C6 | 1.384 (6) | C28—C29 | 1.369 (7) |
C5—H5 | 0.9300 | C29—H29 | 0.9300 |
C6—C7 | 1.361 (6) | C30—H30A | 0.9600 |
C6—H6 | 0.9300 | C30—H30B | 0.9600 |
C7—C8 | 1.498 (6) | C30—H30C | 0.9600 |
C8—C9 | 1.454 (6) | C31—H31A | 0.9600 |
C9—C10 | 1.484 (5) | C31—H31B | 0.9600 |
C10—C11 | 1.518 (5) | C31—H31C | 0.9600 |
C10—C24 | 1.528 (6) | C31'—H31D | 0.9600 |
C10—H10 | 0.9800 | C31'—H31E | 0.9600 |
C11—C16 | 1.354 (5) | C31'—H31F | 0.9600 |
C11—C12 | 1.455 (6) | C32—H32A | 0.9600 |
C12—C13 | 1.494 (6) | C32—H32B | 0.9600 |
C13—C14 | 1.523 (6) | C32—H32C | 0.9600 |
C13—H13A | 0.9700 | C33—H33A | 0.9600 |
C13—H13B | 0.9700 | C33—H33B | 0.9600 |
C14—C34 | 1.517 (6) | C33—H33C | 0.9600 |
C14—C15 | 1.533 (6) | C34—H34A | 0.9600 |
C14—C33 | 1.534 (6) | C34—H34B | 0.9600 |
C15—C16 | 1.496 (5) | C34—H34C | 0.9600 |
C1—N1—C16 | 117.7 (3) | C20—C19—C18 | 122.3 (5) |
C1—N1—C17 | 119.7 (3) | C20—C19—H19 | 118.8 |
C16—N1—C17 | 121.5 (3) | C18—C19—H19 | 118.8 |
C26—O3—C30 | 118.0 (4) | C19—C20—C21 | 118.0 (5) |
C27—O4—C31 | 115.8 (9) | C19—C20—C23 | 121.2 (6) |
C27—O4—C31' | 114.2 (12) | C21—C20—C23 | 120.8 (6) |
C28—O5—C32 | 115.8 (5) | C20—C21—C22 | 121.9 (5) |
C9—C1—N1 | 122.2 (4) | C20—C21—H21 | 119.1 |
C9—C1—C2 | 110.4 (4) | C22—C21—H21 | 119.1 |
N1—C1—C2 | 127.3 (3) | C17—C22—C21 | 118.4 (5) |
C3—C2—C7 | 119.7 (4) | C17—C22—H22 | 120.8 |
C3—C2—C1 | 133.7 (4) | C21—C22—H22 | 120.8 |
C7—C2—C1 | 106.6 (3) | C20—C23—H23A | 109.5 |
C2—C3—C4 | 117.5 (4) | C20—C23—H23B | 109.5 |
C2—C3—H3 | 121.3 | H23A—C23—H23B | 109.5 |
C4—C3—H3 | 121.3 | C20—C23—H23C | 109.5 |
C5—C4—C3 | 123.0 (4) | H23A—C23—H23C | 109.5 |
C5—C4—H4 | 118.5 | H23B—C23—H23C | 109.5 |
C3—C4—H4 | 118.5 | C29—C24—C25 | 119.3 (4) |
C4—C5—C6 | 118.4 (4) | C29—C24—C10 | 118.4 (4) |
C4—C5—H5 | 120.8 | C25—C24—C10 | 122.1 (4) |
C6—C5—H5 | 120.8 | C24—C25—C26 | 120.0 (4) |
C7—C6—C5 | 120.0 (5) | C24—C25—H25 | 120.0 |
C7—C6—H6 | 120.0 | C26—C25—H25 | 120.0 |
C5—C6—H6 | 120.0 | O3—C26—C27 | 115.2 (5) |
C6—C7—C2 | 121.3 (4) | O3—C26—C25 | 124.7 (5) |
C6—C7—C8 | 130.6 (4) | C27—C26—C25 | 120.0 (5) |
C2—C7—C8 | 108.1 (4) | C26—C27—O4 | 119.3 (6) |
O1—C8—C9 | 127.6 (4) | C26—C27—C28 | 119.6 (5) |
O1—C8—C7 | 125.9 (4) | O4—C27—C28 | 120.8 (5) |
C9—C8—C7 | 106.5 (4) | C29—C28—O5 | 125.6 (6) |
C1—C9—C8 | 108.4 (4) | C29—C28—C27 | 119.8 (5) |
C1—C9—C10 | 123.9 (4) | O5—C28—C27 | 114.6 (5) |
C8—C9—C10 | 127.7 (4) | C28—C29—C24 | 121.1 (5) |
C9—C10—C11 | 107.4 (3) | C28—C29—H29 | 119.4 |
C9—C10—C24 | 111.1 (3) | C24—C29—H29 | 119.4 |
C11—C10—C24 | 114.6 (3) | O3—C30—H30A | 109.5 |
C9—C10—H10 | 107.9 | O3—C30—H30B | 109.5 |
C11—C10—H10 | 107.9 | H30A—C30—H30B | 109.5 |
C24—C10—H10 | 107.9 | O3—C30—H30C | 109.5 |
C16—C11—C12 | 119.5 (4) | H30A—C30—H30C | 109.5 |
C16—C11—C10 | 123.2 (4) | H30B—C30—H30C | 109.5 |
C12—C11—C10 | 117.2 (3) | O4—C31—H31A | 109.5 |
O2—C12—C11 | 120.3 (4) | O4—C31—H31B | 109.5 |
O2—C12—C13 | 120.4 (4) | H31A—C31—H31B | 109.5 |
C11—C12—C13 | 119.2 (4) | O4—C31—H31C | 109.5 |
C12—C13—C14 | 114.3 (4) | H31A—C31—H31C | 109.5 |
C12—C13—H13A | 108.7 | H31B—C31—H31C | 109.5 |
C14—C13—H13A | 108.7 | O4—C31'—H31D | 109.5 |
C12—C13—H13B | 108.7 | O4—C31'—H31E | 109.5 |
C14—C13—H13B | 108.7 | H31D—C31'—H31E | 109.5 |
H13A—C13—H13B | 107.6 | O4—C31'—H31F | 109.5 |
C34—C14—C13 | 110.4 (4) | H31D—C31'—H31F | 109.5 |
C34—C14—C15 | 108.3 (3) | H31E—C31'—H31F | 109.5 |
C13—C14—C15 | 108.1 (3) | O5—C32—H32A | 109.5 |
C34—C14—C33 | 109.1 (4) | O5—C32—H32B | 109.5 |
C13—C14—C33 | 110.2 (3) | H32A—C32—H32B | 109.5 |
C15—C14—C33 | 110.7 (4) | O5—C32—H32C | 109.5 |
C16—C15—C14 | 114.2 (3) | H32A—C32—H32C | 109.5 |
C16—C15—H15A | 108.7 | H32B—C32—H32C | 109.5 |
C14—C15—H15A | 108.7 | C14—C33—H33A | 109.5 |
C16—C15—H15B | 108.7 | C14—C33—H33B | 109.5 |
C14—C15—H15B | 108.7 | H33A—C33—H33B | 109.5 |
H15A—C15—H15B | 107.6 | C14—C33—H33C | 109.5 |
C11—C16—N1 | 121.5 (4) | H33A—C33—H33C | 109.5 |
C11—C16—C15 | 122.7 (4) | H33B—C33—H33C | 109.5 |
N1—C16—C15 | 115.7 (3) | C14—C34—H34A | 109.5 |
C22—C17—C18 | 120.8 (4) | C14—C34—H34B | 109.5 |
C22—C17—N1 | 120.0 (4) | H34A—C34—H34B | 109.5 |
C18—C17—N1 | 119.2 (4) | C14—C34—H34C | 109.5 |
C17—C18—C19 | 118.6 (5) | H34A—C34—H34C | 109.5 |
C17—C18—H18 | 120.7 | H34B—C34—H34C | 109.5 |
C19—C18—H18 | 120.7 |