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
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 |