Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014406/hk6003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014406/hk6003Isup2.hkl |
CCDC reference: 274434
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C36H42O3 | Z = 2 |
Mr = 522.70 | F(000) = 564 |
Triclinic, P1 | Dx = 1.119 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3172 (7) Å | Cell parameters from 17053 reflections |
b = 11.5055 (9) Å | θ = 1.4–27.1° |
c = 16.3424 (13) Å | µ = 0.07 mm−1 |
α = 104.677 (6)° | T = 298 K |
β = 105.307 (6)° | Prism, colorless |
γ = 103.098 (6)° | 0.71 × 0.34 × 0.14 mm |
V = 1551.6 (2) Å3 |
Stoe IPDS-II diffractometer | 6830 independent reflections |
Radiation source: sealed X-ray tube | 2985 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.050 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.2°, θmin = 1.4° |
φ and ω scans | h = −10→11 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.970, Tmax = 0.992 | l = −20→20 |
21653 measured reflections |
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)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.076P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.85 | (Δ/σ)max = 0.001 |
6830 reflections | Δρmax = 0.35 e Å−3 |
461 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.010 (2) |
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 | ||
C1 | 0.8503 (2) | 0.14738 (16) | 0.12785 (11) | 0.0629 (5) | |
C2 | 0.7323 (2) | 0.04886 (17) | 0.12689 (12) | 0.0639 (5) | |
C3 | 0.6513 (2) | −0.05593 (16) | 0.04974 (10) | 0.0593 (4) | |
C4 | 0.6908 (2) | −0.06000 (17) | −0.02668 (11) | 0.0609 (5) | |
C5 | 0.8079 (2) | 0.03686 (16) | −0.02767 (11) | 0.0597 (4) | |
C6 | 0.8871 (2) | 0.14096 (18) | 0.05046 (12) | 0.0642 (5) | |
C7 | 0.9372 (3) | 0.25842 (18) | 0.21294 (13) | 0.0714 (5) | |
C8 | 0.5212 (3) | −0.16488 (19) | 0.04454 (12) | 0.0663 (5) | |
C9 | 0.8516 (3) | 0.03352 (19) | −0.11030 (12) | 0.0665 (5) | |
C10 | 0.9403 (2) | 0.47067 (17) | 0.27775 (11) | 0.0659 (5) | |
C11 | 1.0338 (3) | 0.4788 (2) | 0.36142 (13) | 0.0827 (6) | |
C12 | 1.0870 (3) | 0.5943 (3) | 0.43145 (16) | 0.1045 (8) | |
C13 | 1.0497 (3) | 0.6968 (3) | 0.41715 (19) | 0.1113 (9) | |
C14 | 0.9578 (3) | 0.6867 (2) | 0.33357 (19) | 0.0998 (8) | |
C15 | 0.9003 (2) | 0.57443 (18) | 0.26146 (13) | 0.0746 (5) | |
C16 | 0.7996 (3) | 0.5620 (2) | 0.16871 (15) | 0.0879 (7) | |
C17 | 0.6270 (4) | 0.5066 (4) | 0.1534 (2) | 0.1165 (9) | |
C18 | 0.8331 (4) | 0.6846 (2) | 0.14677 (19) | 0.1309 (10) | |
H18A | 0.7653 | 0.6704 | 0.0872 | 0.196* | |
H18B | 0.9404 | 0.7116 | 0.1500 | 0.196* | |
H18C | 0.8145 | 0.7489 | 0.1893 | 0.196* | |
C19 | 0.3998 (2) | −0.24510 (19) | 0.13888 (12) | 0.0698 (5) | |
C20 | 0.3032 (3) | −0.3511 (2) | 0.06754 (15) | 0.0839 (6) | |
C21 | 0.2073 (3) | −0.4487 (3) | 0.0820 (2) | 0.1071 (8) | |
C22 | 0.2054 (4) | −0.4390 (3) | 0.1664 (2) | 0.1145 (9) | |
C23 | 0.2979 (4) | −0.3310 (3) | 0.2366 (2) | 0.1020 (8) | |
C24 | 0.3971 (3) | −0.2307 (2) | 0.22584 (13) | 0.0781 (6) | |
C25 | 0.4965 (4) | −0.1099 (3) | 0.30162 (15) | 0.1016 (8) | |
C26 | 0.4353 (4) | −0.0784 (3) | 0.37942 (19) | 0.1487 (12) | |
H26A | 0.3279 | −0.0814 | 0.3566 | 0.223* | |
H26B | 0.4971 | 0.0050 | 0.4205 | 0.223* | |
H26C | 0.4422 | −0.1388 | 0.4102 | 0.223* | |
C27 | 0.6588 (4) | −0.1065 (4) | 0.3332 (2) | 0.1625 (14) | |
H27A | 0.7192 | −0.0286 | 0.3815 | 0.244* | |
H27B | 0.6997 | −0.1120 | 0.2847 | 0.244* | |
H27C | 0.6649 | −0.1765 | 0.3542 | 0.244* | |
C28 | 0.7833 (2) | −0.11112 (18) | −0.25990 (12) | 0.0677 (5) | |
C29 | 0.8972 (3) | −0.0335 (2) | −0.27834 (15) | 0.0822 (6) | |
C30 | 0.9105 (4) | −0.0682 (3) | −0.36294 (17) | 0.1025 (8) | |
C31 | 0.8127 (4) | −0.1782 (3) | −0.42676 (18) | 0.1121 (9) | |
C32 | 0.6993 (3) | −0.2555 (3) | −0.40804 (15) | 0.0970 (7) | |
C33 | 0.6806 (2) | −0.22584 (19) | −0.32476 (12) | 0.0738 (5) | |
C34 | 0.5563 (3) | −0.3091 (2) | −0.30311 (16) | 0.0888 (7) | |
C35 | 0.4206 (3) | −0.2567 (3) | −0.3041 (2) | 0.1298 (10) | |
H35A | 0.3433 | −0.3111 | −0.2899 | 0.195* | |
H35B | 0.3745 | −0.2525 | −0.3628 | 0.195* | |
H35C | 0.4582 | −0.1735 | −0.2603 | 0.195* | |
C36 | 0.4934 (4) | −0.4469 (2) | −0.3645 (2) | 0.1393 (12) | |
H36A | 0.4151 | −0.4938 | −0.3467 | 0.209* | |
H36B | 0.5778 | −0.4825 | −0.3600 | 0.209* | |
H36C | 0.4478 | −0.4510 | −0.4256 | 0.209* | |
O1 | 0.88017 (15) | 0.36085 (11) | 0.20461 (7) | 0.0700 (4) | |
O2 | 0.50156 (17) | −0.14682 (12) | 0.12942 (8) | 0.0805 (4) | |
O3 | 0.76306 (16) | −0.08589 (12) | −0.17808 (8) | 0.0791 (4) | |
H2 | 0.703 (2) | 0.0498 (16) | 0.1771 (13) | 0.073 (5)* | |
H4 | 0.638 (2) | −0.1301 (17) | −0.0799 (12) | 0.071 (5)* | |
H6 | 0.971 (2) | 0.2097 (16) | 0.0546 (11) | 0.066 (5)* | |
H7A | 1.055 (3) | 0.2897 (17) | 0.2242 (12) | 0.080 (6)* | |
H7B | 0.917 (2) | 0.2365 (17) | 0.2630 (13) | 0.078 (6)* | |
H8A | 0.547 (2) | −0.2462 (17) | 0.0246 (11) | 0.065 (5)* | |
H8B | 0.421 (2) | −0.1703 (16) | 0.0013 (12) | 0.068 (5)* | |
H9A | 0.828 (2) | 0.1009 (19) | −0.1317 (12) | 0.087 (6)* | |
H9B | 0.965 (2) | 0.0431 (16) | −0.0952 (11) | 0.070 (5)* | |
H11 | 1.065 (2) | 0.408 (2) | 0.3716 (13) | 0.089 (7)* | |
H12 | 1.151 (3) | 0.588 (2) | 0.4877 (17) | 0.118 (8)* | |
H13 | 1.088 (3) | 0.779 (2) | 0.4655 (17) | 0.126 (8)* | |
H14 | 0.927 (3) | 0.759 (3) | 0.3245 (17) | 0.125 (9)* | |
H16 | 0.832 (2) | 0.5040 (19) | 0.1251 (13) | 0.083 (6)* | |
H17A | 0.599 (3) | 0.570 (3) | 0.200 (2) | 0.144 (10)* | |
H17B | 0.564 (4) | 0.498 (3) | 0.091 (2) | 0.155 (12)* | |
H17C | 0.603 (4) | 0.421 (3) | 0.1638 (19) | 0.148 (12)* | |
H20 | 0.305 (3) | −0.3590 (19) | 0.0040 (15) | 0.105 (7)* | |
H21 | 0.138 (3) | −0.523 (3) | 0.0327 (19) | 0.137 (10)* | |
H22 | 0.140 (4) | −0.513 (3) | 0.175 (2) | 0.159 (11)* | |
H23 | 0.304 (3) | −0.315 (2) | 0.2963 (17) | 0.116 (8)* | |
H25 | 0.501 (3) | −0.023 (2) | 0.2938 (16) | 0.118 (9)* | |
H29 | 0.969 (3) | 0.046 (2) | −0.2311 (16) | 0.110 (8)* | |
H30 | 0.995 (3) | −0.009 (2) | −0.3778 (16) | 0.118 (8)* | |
H31 | 0.818 (3) | −0.206 (2) | −0.4860 (17) | 0.117 (8)* | |
H32 | 0.630 (3) | −0.332 (2) | −0.4533 (17) | 0.115 (8)* | |
H34 | 0.603 (2) | −0.3132 (18) | −0.2441 (14) | 0.086 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0741 (12) | 0.0556 (10) | 0.0520 (10) | 0.0279 (9) | 0.0099 (8) | 0.0117 (8) |
C2 | 0.0816 (13) | 0.0632 (11) | 0.0488 (10) | 0.0329 (10) | 0.0190 (9) | 0.0159 (9) |
C3 | 0.0712 (12) | 0.0567 (10) | 0.0489 (9) | 0.0263 (9) | 0.0143 (8) | 0.0167 (8) |
C4 | 0.0719 (12) | 0.0575 (11) | 0.0472 (9) | 0.0250 (10) | 0.0134 (9) | 0.0108 (8) |
C5 | 0.0656 (11) | 0.0564 (10) | 0.0552 (10) | 0.0248 (9) | 0.0158 (8) | 0.0153 (8) |
C6 | 0.0686 (12) | 0.0557 (11) | 0.0602 (11) | 0.0202 (10) | 0.0134 (9) | 0.0144 (9) |
C7 | 0.0886 (16) | 0.0584 (11) | 0.0559 (11) | 0.0282 (11) | 0.0105 (10) | 0.0105 (9) |
C8 | 0.0826 (14) | 0.0649 (12) | 0.0492 (10) | 0.0248 (11) | 0.0196 (10) | 0.0170 (9) |
C9 | 0.0761 (15) | 0.0608 (12) | 0.0575 (10) | 0.0230 (11) | 0.0203 (10) | 0.0126 (9) |
C10 | 0.0699 (12) | 0.0610 (11) | 0.0527 (10) | 0.0155 (9) | 0.0194 (9) | 0.0017 (8) |
C11 | 0.0910 (16) | 0.0782 (14) | 0.0594 (12) | 0.0216 (12) | 0.0150 (11) | 0.0062 (10) |
C12 | 0.108 (2) | 0.104 (2) | 0.0627 (14) | 0.0214 (16) | 0.0107 (13) | −0.0066 (13) |
C13 | 0.118 (2) | 0.0869 (18) | 0.0890 (18) | 0.0252 (16) | 0.0262 (16) | −0.0217 (15) |
C14 | 0.110 (2) | 0.0724 (15) | 0.0951 (18) | 0.0308 (14) | 0.0309 (15) | −0.0048 (13) |
C15 | 0.0814 (14) | 0.0609 (11) | 0.0703 (12) | 0.0237 (10) | 0.0244 (10) | 0.0035 (9) |
C16 | 0.1076 (19) | 0.0711 (13) | 0.0821 (14) | 0.0431 (13) | 0.0253 (13) | 0.0150 (11) |
C17 | 0.102 (2) | 0.119 (3) | 0.107 (2) | 0.0457 (19) | 0.0137 (17) | 0.0168 (19) |
C18 | 0.185 (3) | 0.0916 (18) | 0.125 (2) | 0.0668 (19) | 0.044 (2) | 0.0408 (16) |
C19 | 0.0779 (13) | 0.0764 (13) | 0.0642 (11) | 0.0317 (11) | 0.0263 (10) | 0.0293 (10) |
C20 | 0.0832 (15) | 0.0860 (15) | 0.0708 (13) | 0.0140 (12) | 0.0245 (11) | 0.0198 (12) |
C21 | 0.0966 (18) | 0.104 (2) | 0.110 (2) | 0.0110 (16) | 0.0459 (16) | 0.0244 (17) |
C22 | 0.123 (2) | 0.107 (2) | 0.128 (2) | 0.0261 (18) | 0.072 (2) | 0.0415 (19) |
C23 | 0.128 (2) | 0.117 (2) | 0.0955 (18) | 0.0502 (18) | 0.0656 (17) | 0.0528 (17) |
C24 | 0.0932 (15) | 0.0873 (14) | 0.0681 (12) | 0.0401 (12) | 0.0342 (11) | 0.0319 (11) |
C25 | 0.125 (2) | 0.119 (2) | 0.0645 (13) | 0.0385 (17) | 0.0391 (14) | 0.0291 (14) |
C26 | 0.188 (3) | 0.184 (3) | 0.0922 (18) | 0.095 (3) | 0.064 (2) | 0.0265 (19) |
C27 | 0.115 (3) | 0.198 (4) | 0.116 (2) | 0.040 (2) | 0.023 (2) | −0.018 (2) |
C28 | 0.0758 (13) | 0.0746 (12) | 0.0568 (10) | 0.0312 (10) | 0.0266 (10) | 0.0176 (9) |
C29 | 0.0897 (16) | 0.0850 (15) | 0.0747 (13) | 0.0276 (13) | 0.0348 (12) | 0.0239 (12) |
C30 | 0.116 (2) | 0.117 (2) | 0.0911 (17) | 0.0377 (17) | 0.0590 (16) | 0.0349 (16) |
C31 | 0.138 (2) | 0.132 (2) | 0.0722 (16) | 0.045 (2) | 0.0547 (17) | 0.0210 (16) |
C32 | 0.110 (2) | 0.1035 (18) | 0.0654 (14) | 0.0325 (16) | 0.0317 (14) | 0.0069 (13) |
C33 | 0.0781 (13) | 0.0795 (13) | 0.0581 (11) | 0.0289 (11) | 0.0219 (10) | 0.0115 (10) |
C34 | 0.0962 (17) | 0.0799 (14) | 0.0694 (14) | 0.0168 (13) | 0.0262 (12) | 0.0021 (11) |
C35 | 0.0973 (19) | 0.118 (2) | 0.150 (3) | 0.0136 (17) | 0.0533 (18) | 0.0107 (18) |
C36 | 0.182 (3) | 0.0810 (17) | 0.120 (2) | 0.0114 (18) | 0.055 (2) | −0.0015 (15) |
O1 | 0.0836 (9) | 0.0553 (7) | 0.0561 (7) | 0.0252 (6) | 0.0103 (6) | 0.0051 (5) |
O2 | 0.1072 (10) | 0.0741 (8) | 0.0523 (7) | 0.0165 (8) | 0.0291 (7) | 0.0168 (6) |
O3 | 0.0921 (10) | 0.0735 (8) | 0.0558 (7) | 0.0096 (7) | 0.0289 (7) | 0.0062 (6) |
C1—C2 | 1.382 (3) | C19—O2 | 1.372 (2) |
C1—C6 | 1.384 (2) | C19—C20 | 1.373 (3) |
C1—C7 | 1.503 (2) | C19—C24 | 1.396 (3) |
C2—C3 | 1.388 (2) | C20—C21 | 1.380 (3) |
C2—H2 | 0.929 (18) | C20—H20 | 1.02 (2) |
C3—C4 | 1.385 (2) | C21—C22 | 1.360 (4) |
C3—C8 | 1.500 (3) | C21—H21 | 0.96 (3) |
C4—C5 | 1.379 (2) | C22—C23 | 1.369 (4) |
C4—H4 | 0.942 (18) | C22—H22 | 1.00 (3) |
C5—C6 | 1.391 (2) | C23—C24 | 1.386 (3) |
C5—C9 | 1.504 (2) | C23—H23 | 0.93 (3) |
C6—H6 | 0.950 (17) | C24—C25 | 1.504 (3) |
C7—O1 | 1.420 (2) | C25—C27 | 1.451 (4) |
C7—H7A | 1.03 (2) | C25—C26 | 1.522 (3) |
C7—H7B | 0.965 (18) | C25—H25 | 1.03 (3) |
C8—O2 | 1.416 (2) | C26—H26A | 0.9600 |
C8—H8A | 1.012 (18) | C26—H26B | 0.9600 |
C8—H8B | 0.987 (19) | C26—H26C | 0.9600 |
C9—O3 | 1.424 (2) | C27—H27A | 0.9600 |
C9—H9A | 0.97 (2) | C27—H27B | 0.9600 |
C9—H9B | 0.997 (19) | C27—H27C | 0.9600 |
C10—O1 | 1.3783 (19) | C28—O3 | 1.367 (2) |
C10—C11 | 1.381 (3) | C28—C29 | 1.375 (3) |
C10—C15 | 1.395 (3) | C28—C33 | 1.402 (3) |
C11—C12 | 1.397 (3) | C29—C30 | 1.385 (3) |
C11—H11 | 0.97 (2) | C29—H29 | 0.99 (2) |
C12—C13 | 1.360 (4) | C30—C31 | 1.352 (4) |
C12—H12 | 0.99 (2) | C30—H30 | 1.04 (2) |
C13—C14 | 1.367 (4) | C31—C32 | 1.372 (4) |
C13—H13 | 0.98 (3) | C31—H31 | 0.96 (2) |
C14—C15 | 1.388 (3) | C32—C33 | 1.384 (3) |
C14—H14 | 0.96 (3) | C32—H32 | 0.95 (3) |
C15—C16 | 1.509 (3) | C33—C34 | 1.507 (3) |
C16—C17 | 1.516 (4) | C34—C35 | 1.516 (4) |
C16—C18 | 1.528 (3) | C34—C36 | 1.525 (3) |
C16—H16 | 1.01 (2) | C34—H34 | 0.97 (2) |
C17—H17A | 1.04 (3) | C35—H35A | 0.9600 |
C17—H17B | 1.00 (3) | C35—H35B | 0.9600 |
C17—H17C | 1.03 (3) | C35—H35C | 0.9600 |
C18—H18A | 0.9600 | C36—H36A | 0.9600 |
C18—H18B | 0.9600 | C36—H36B | 0.9600 |
C18—H18C | 0.9600 | C36—H36C | 0.9600 |
C2—C1—C6 | 119.17 (16) | C20—C19—C24 | 121.1 (2) |
C2—C1—C7 | 119.50 (17) | C19—C20—C21 | 119.9 (2) |
C6—C1—C7 | 121.32 (19) | C19—C20—H20 | 120.0 (12) |
C1—C2—C3 | 120.94 (17) | C21—C20—H20 | 120.1 (12) |
C1—C2—H2 | 122.0 (11) | C22—C21—C20 | 120.3 (3) |
C3—C2—H2 | 117.1 (11) | C22—C21—H21 | 118.8 (17) |
C4—C3—C2 | 118.67 (18) | C20—C21—H21 | 120.9 (17) |
C4—C3—C8 | 118.10 (15) | C21—C22—C23 | 119.4 (3) |
C2—C3—C8 | 123.23 (16) | C21—C22—H22 | 118.3 (18) |
C5—C4—C3 | 121.66 (17) | C23—C22—H22 | 122.2 (18) |
C5—C4—H4 | 117.7 (10) | C22—C23—C24 | 122.6 (2) |
C3—C4—H4 | 120.6 (10) | C22—C23—H23 | 125.8 (15) |
C4—C5—C6 | 118.53 (17) | C24—C23—H23 | 111.6 (15) |
C4—C5—C9 | 122.10 (16) | C23—C24—C19 | 116.6 (2) |
C6—C5—C9 | 119.37 (17) | C23—C24—C25 | 123.4 (2) |
C1—C6—C5 | 121.03 (18) | C19—C24—C25 | 119.94 (19) |
C1—C6—H6 | 116.4 (10) | C27—C25—C24 | 111.4 (3) |
C5—C6—H6 | 122.6 (10) | C27—C25—C26 | 111.3 (2) |
O1—C7—C1 | 108.48 (15) | C24—C25—C26 | 115.0 (2) |
O1—C7—H7A | 106.5 (11) | C27—C25—H25 | 105.3 (15) |
C1—C7—H7A | 112.6 (10) | C24—C25—H25 | 120.8 (14) |
O1—C7—H7B | 108.6 (11) | C26—C25—H25 | 91.4 (14) |
C1—C7—H7B | 109.5 (11) | C25—C26—H26A | 109.5 |
H7A—C7—H7B | 111.0 (15) | C25—C26—H26B | 109.5 |
O2—C8—C3 | 110.19 (15) | H26A—C26—H26B | 109.5 |
O2—C8—H8A | 110.2 (9) | C25—C26—H26C | 109.5 |
C3—C8—H8A | 109.3 (9) | H26A—C26—H26C | 109.5 |
O2—C8—H8B | 107.3 (10) | H26B—C26—H26C | 109.5 |
C3—C8—H8B | 110.3 (10) | C25—C27—H27A | 109.5 |
H8A—C8—H8B | 109.5 (14) | C25—C27—H27B | 109.5 |
O3—C9—C5 | 108.42 (16) | H27A—C27—H27B | 109.5 |
O3—C9—H9A | 109.7 (11) | C25—C27—H27C | 109.5 |
C5—C9—H9A | 110.2 (12) | H27A—C27—H27C | 109.5 |
O3—C9—H9B | 109.2 (10) | H27B—C27—H27C | 109.5 |
C5—C9—H9B | 108.9 (10) | O3—C28—C29 | 123.80 (18) |
H9A—C9—H9B | 110.4 (15) | O3—C28—C33 | 114.79 (16) |
O1—C10—C11 | 122.97 (19) | C29—C28—C33 | 121.39 (17) |
O1—C10—C15 | 115.17 (16) | C28—C29—C30 | 119.6 (2) |
C11—C10—C15 | 121.86 (18) | C28—C29—H29 | 119.7 (13) |
C10—C11—C12 | 118.4 (3) | C30—C29—H29 | 120.6 (13) |
C10—C11—H11 | 121.5 (12) | C31—C30—C29 | 120.1 (3) |
C12—C11—H11 | 120.0 (12) | C31—C30—H30 | 119.7 (13) |
C13—C12—C11 | 120.8 (3) | C29—C30—H30 | 120.1 (13) |
C13—C12—H12 | 128.5 (15) | C30—C31—C32 | 120.0 (2) |
C11—C12—H12 | 110.7 (15) | C30—C31—H31 | 123.0 (14) |
C12—C13—C14 | 119.8 (2) | C32—C31—H31 | 117.0 (14) |
C12—C13—H13 | 121.6 (15) | C31—C32—C33 | 122.4 (2) |
C14—C13—H13 | 118.6 (15) | C31—C32—H32 | 119.8 (14) |
C13—C14—C15 | 122.2 (3) | C33—C32—H32 | 117.8 (15) |
C13—C14—H14 | 119.4 (15) | C32—C33—C28 | 116.4 (2) |
C15—C14—H14 | 118.3 (16) | C32—C33—C34 | 123.1 (2) |
C14—C15—C10 | 117.0 (2) | C28—C33—C34 | 120.43 (16) |
C14—C15—C16 | 122.9 (2) | C33—C34—C35 | 111.1 (2) |
C10—C15—C16 | 120.17 (16) | C33—C34—C36 | 114.26 (19) |
C15—C16—C17 | 111.4 (2) | C35—C34—C36 | 109.3 (2) |
C15—C16—C18 | 113.6 (2) | C33—C34—H34 | 108.2 (12) |
C17—C16—C18 | 111.6 (3) | C35—C34—H34 | 109.7 (12) |
C15—C16—H16 | 106.1 (11) | C36—C34—H34 | 104.1 (12) |
C17—C16—H16 | 110.2 (11) | C34—C35—H35A | 109.5 |
C18—C16—H16 | 103.5 (11) | C34—C35—H35B | 109.5 |
C16—C17—H17A | 107.2 (16) | H35A—C35—H35B | 109.5 |
C16—C17—H17B | 109.4 (18) | C34—C35—H35C | 109.5 |
H17A—C17—H17B | 109 (3) | H35A—C35—H35C | 109.5 |
C16—C17—H17C | 111.7 (18) | H35B—C35—H35C | 109.5 |
H17A—C17—H17C | 108 (2) | C34—C36—H36A | 109.5 |
H17B—C17—H17C | 111 (2) | C34—C36—H36B | 109.5 |
C16—C18—H18A | 109.5 | H36A—C36—H36B | 109.5 |
C16—C18—H18B | 109.5 | C34—C36—H36C | 109.5 |
H18A—C18—H18B | 109.5 | H36A—C36—H36C | 109.5 |
C16—C18—H18C | 109.5 | H36B—C36—H36C | 109.5 |
H18A—C18—H18C | 109.5 | C10—O1—C7 | 117.57 (14) |
H18B—C18—H18C | 109.5 | C19—O2—C8 | 117.42 (14) |
O2—C19—C20 | 122.73 (17) | C28—O3—C9 | 119.07 (15) |
O2—C19—C24 | 116.12 (18) | ||
C6—C1—C2—C3 | 0.2 (3) | C20—C21—C22—C23 | 0.9 (5) |
C7—C1—C2—C3 | −179.07 (18) | C21—C22—C23—C24 | −1.4 (5) |
C1—C2—C3—C4 | −0.1 (3) | C22—C23—C24—C19 | −0.5 (4) |
C1—C2—C3—C8 | −179.33 (18) | C22—C23—C24—C25 | 178.4 (3) |
C2—C3—C4—C5 | 0.1 (3) | O2—C19—C24—C23 | −178.23 (19) |
C8—C3—C4—C5 | 179.37 (17) | C20—C19—C24—C23 | 2.9 (3) |
C3—C4—C5—C6 | −0.2 (3) | O2—C19—C24—C25 | 2.9 (3) |
C3—C4—C5—C9 | −179.89 (18) | C20—C19—C24—C25 | −176.0 (2) |
C2—C1—C6—C5 | −0.4 (3) | C23—C24—C25—C27 | 102.6 (3) |
C7—C1—C6—C5 | 178.90 (17) | C19—C24—C25—C27 | −78.6 (3) |
C4—C5—C6—C1 | 0.4 (3) | C23—C24—C25—C26 | −25.2 (4) |
C9—C5—C6—C1 | −179.95 (18) | C19—C24—C25—C26 | 153.6 (2) |
C2—C1—C7—O1 | −102.9 (2) | O3—C28—C29—C30 | 178.9 (2) |
C6—C1—C7—O1 | 77.8 (2) | C33—C28—C29—C30 | 0.6 (3) |
C4—C3—C8—O2 | 177.66 (16) | C28—C29—C30—C31 | −0.5 (4) |
C2—C3—C8—O2 | −3.1 (3) | C29—C30—C31—C32 | 0.5 (4) |
C4—C5—C9—O3 | −4.8 (3) | C30—C31—C32—C33 | −0.5 (4) |
C6—C5—C9—O3 | 175.51 (17) | C31—C32—C33—C28 | 0.6 (4) |
O1—C10—C11—C12 | −179.2 (2) | C31—C32—C33—C34 | 179.6 (3) |
C15—C10—C11—C12 | 1.0 (3) | O3—C28—C33—C32 | −179.05 (19) |
C10—C11—C12—C13 | −1.1 (4) | C29—C28—C33—C32 | −0.7 (3) |
C11—C12—C13—C14 | 0.6 (4) | O3—C28—C33—C34 | 1.9 (3) |
C12—C13—C14—C15 | −0.1 (4) | C29—C28—C33—C34 | −179.7 (2) |
C13—C14—C15—C10 | 0.1 (4) | C32—C33—C34—C35 | −102.7 (3) |
C13—C14—C15—C16 | −179.6 (2) | C28—C33—C34—C35 | 76.3 (3) |
O1—C10—C15—C14 | 179.63 (19) | C32—C33—C34—C36 | 21.5 (4) |
C11—C10—C15—C14 | −0.6 (3) | C28—C33—C34—C36 | −159.5 (2) |
O1—C10—C15—C16 | −0.6 (3) | C11—C10—O1—C7 | −9.9 (3) |
C11—C10—C15—C16 | 179.2 (2) | C15—C10—O1—C7 | 169.90 (18) |
C14—C15—C16—C17 | −97.2 (3) | C1—C7—O1—C10 | 177.07 (16) |
C10—C15—C16—C17 | 83.1 (3) | C20—C19—O2—C8 | −8.7 (3) |
C14—C15—C16—C18 | 29.8 (3) | C24—C19—O2—C8 | 172.43 (18) |
C10—C15—C16—C18 | −149.9 (2) | C3—C8—O2—C19 | −172.44 (16) |
O2—C19—C20—C21 | 177.7 (2) | C29—C28—O3—C9 | 7.5 (3) |
C24—C19—C20—C21 | −3.5 (3) | C33—C28—O3—C9 | −174.19 (18) |
C19—C20—C21—C22 | 1.5 (4) | C5—C9—O3—C28 | −179.86 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2 | 0.929 (18) | 2.379 (17) | 2.756 (2) | 104.1 (13) |
C4—H4···O3 | 0.942 (18) | 2.305 (17) | 2.695 (2) | 104.2 (12) |