Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013273/bt6446sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013273/bt6446Isup2.hkl |
CCDC reference: 245292
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C36H45Br3O6 | F(000) = 828 |
Mr = 813.45 | Dx = 1.511 Mg m−3 |
Triclinic, P1 | Melting point = 122–124 K |
a = 9.328 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.393 (3) Å | Cell parameters from 1024 reflections |
c = 15.694 (4) Å | θ = 3.7–24.4° |
α = 76.951 (4)° | µ = 3.43 mm−1 |
β = 75.162 (4)° | T = 293 K |
γ = 72.894 (4)° | Block, colorless |
V = 1787.4 (8) Å3 | 0.24 × 0.20 × 0.16 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 7248 independent reflections |
Radiation source: fine-focus sealed tube | 3984 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→7 |
Tmin = 0.432, Tmax = 0.578 | k = −16→12 |
10436 measured reflections | l = −18→19 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.163 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0696P)2 + 1.5971P] where P = (Fo2 + 2Fc2)/3 |
7248 reflections | (Δ/σ)max = 0.001 |
428 parameters | Δρmax = 0.85 e Å−3 |
35 restraints | Δρmin = −0.92 e Å−3 |
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) | |
Br1 | 0.49899 (8) | 1.31459 (6) | 0.13754 (5) | 0.0915 (3) | |
Br2 | −0.34456 (9) | 0.81617 (6) | 1.26869 (4) | 0.1008 (3) | |
O1 | 0.3157 (3) | 1.0687 (2) | 0.46375 (19) | 0.0443 (7) | |
O2 | 0.0820 (4) | 1.1105 (2) | 0.5941 (2) | 0.0521 (8) | |
O3 | −0.1151 (3) | 0.7527 (2) | 0.96094 (19) | 0.0463 (8) | |
O4 | 0.1023 (3) | 0.5818 (2) | 0.98408 (19) | 0.0461 (8) | |
O5 | 0.7522 (3) | 0.4243 (2) | 0.67976 (19) | 0.0416 (7) | |
O6 | 0.8267 (3) | 0.5689 (2) | 0.5355 (2) | 0.0509 (8) | |
C1 | 0.2225 (4) | 0.8072 (3) | 0.5264 (3) | 0.0336 (9) | |
C2 | 0.2996 (5) | 0.8865 (3) | 0.4845 (3) | 0.0359 (10) | |
H2 | 0.3874 | 0.8705 | 0.4406 | 0.043* | |
C3 | 0.2504 (5) | 0.9875 (3) | 0.5056 (3) | 0.0359 (10) | |
C4 | 0.1212 (5) | 1.0097 (3) | 0.5742 (3) | 0.0381 (10) | |
C5 | 0.0433 (5) | 0.9342 (3) | 0.6134 (3) | 0.0373 (10) | |
H5 | −0.0441 | 0.9507 | 0.6574 | 0.045* | |
C6 | 0.0892 (4) | 0.8322 (3) | 0.5904 (3) | 0.0321 (9) | |
C7 | −0.0111 (4) | 0.7573 (3) | 0.6354 (3) | 0.0361 (10) | |
H7A | 0.0061 | 0.7050 | 0.5976 | 0.043* | |
H7B | −0.1175 | 0.7968 | 0.6413 | 0.043* | |
C8 | 0.0176 (4) | 0.7003 (3) | 0.7273 (3) | 0.0317 (9) | |
C9 | −0.0629 (4) | 0.7504 (3) | 0.8007 (3) | 0.0356 (10) | |
H9 | −0.1367 | 0.8138 | 0.7918 | 0.043* | |
C10 | −0.0370 (5) | 0.7093 (3) | 0.8856 (3) | 0.0361 (10) | |
C11 | 0.0778 (5) | 0.6150 (3) | 0.8986 (3) | 0.0355 (10) | |
C12 | 0.1507 (4) | 0.5634 (3) | 0.8275 (3) | 0.0345 (10) | |
H12 | 0.2218 | 0.4988 | 0.8368 | 0.041* | |
C13 | 0.1229 (4) | 0.6037 (3) | 0.7414 (3) | 0.0313 (9) | |
C14 | 0.2112 (4) | 0.5392 (3) | 0.6673 (3) | 0.0359 (10) | |
H14A | 0.2184 | 0.4648 | 0.6909 | 0.043* | |
H14B | 0.1536 | 0.5587 | 0.6200 | 0.043* | |
C15 | 0.3716 (4) | 0.5536 (3) | 0.6272 (3) | 0.0322 (9) | |
C16 | 0.4901 (5) | 0.4898 (3) | 0.6691 (3) | 0.0364 (10) | |
H16 | 0.4670 | 0.4410 | 0.7196 | 0.044* | |
C17 | 0.6399 (4) | 0.4961 (3) | 0.6387 (3) | 0.0352 (10) | |
C18 | 0.6757 (5) | 0.5693 (3) | 0.5629 (3) | 0.0363 (10) | |
C19 | 0.5600 (5) | 0.6326 (3) | 0.5209 (3) | 0.0356 (10) | |
H19 | 0.5839 | 0.6813 | 0.4705 | 0.043* | |
C20 | 0.4077 (4) | 0.6264 (3) | 0.5511 (3) | 0.0316 (9) | |
C21 | 0.2897 (5) | 0.6987 (3) | 0.4990 (3) | 0.0358 (10) | |
H21A | 0.2072 | 0.6651 | 0.5069 | 0.043* | |
H21B | 0.3370 | 0.7073 | 0.4360 | 0.043* | |
C22 | 0.4332 (5) | 1.0515 (3) | 0.3860 (3) | 0.0425 (11) | |
H22A | 0.3980 | 1.0240 | 0.3451 | 0.051* | |
H22B | 0.5232 | 0.9998 | 0.4026 | 0.051* | |
C23 | 0.4729 (5) | 1.1540 (4) | 0.3414 (3) | 0.0520 (12) | |
H23A | 0.4969 | 1.1851 | 0.3845 | 0.062* | |
H23B | 0.3854 | 1.2029 | 0.3195 | 0.062* | |
C24 | 0.6094 (5) | 1.1367 (4) | 0.2639 (4) | 0.0631 (15) | |
H24A | 0.6982 | 1.0925 | 0.2873 | 0.076* | |
H24B | 0.5885 | 1.0985 | 0.2247 | 0.076* | |
C25 | 0.6476 (7) | 1.2367 (5) | 0.2099 (4) | 0.0784 (18) | |
H25A | 0.7480 | 1.2193 | 0.1716 | 0.094* | |
H25B | 0.6517 | 1.2810 | 0.2499 | 0.094* | |
C26 | −0.2423 (6) | 0.8422 (4) | 0.9520 (3) | 0.0559 (13) | |
H26A | −0.3139 | 0.8262 | 0.9249 | 0.067* | |
H26B | −0.2077 | 0.9023 | 0.9143 | 0.067* | |
C27 | −0.3192 (6) | 0.8676 (4) | 1.0449 (3) | 0.0625 (14) | |
H27A | −0.3988 | 0.9330 | 1.0400 | 0.075* | |
H27B | −0.2442 | 0.8788 | 1.0722 | 0.075* | |
C28 | −0.3897 (7) | 0.7808 (5) | 1.1055 (4) | 0.0772 (18) | |
H28A | −0.3090 | 0.7168 | 1.1144 | 0.093* | |
H28B | −0.4592 | 0.7657 | 1.0763 | 0.093* | |
C29 | −0.4775 (7) | 0.8114 (5) | 1.1970 (4) | 0.086 (2) | |
H29A | −0.5364 | 0.7603 | 1.2281 | 0.103* | |
H29B | −0.5488 | 0.8802 | 1.1880 | 0.103* | |
C30 | 0.8129 (6) | 0.4675 (4) | 0.7343 (3) | 0.0522 (12) | |
H30A | 0.7300 | 0.5115 | 0.7713 | 0.063* | |
H30B | 0.8792 | 0.5111 | 0.6967 | 0.063* | |
C31 | 0.9008 (6) | 0.3798 (4) | 0.7914 (3) | 0.0538 (12) | |
H31A | 0.9428 | 0.4095 | 0.8276 | 0.065* | |
H31B | 0.9862 | 0.3386 | 0.7534 | 0.065* | |
C34 | −0.0462 (6) | 1.1352 (4) | 0.6638 (3) | 0.0615 (14) | |
H34A | −0.1336 | 1.1223 | 0.6508 | 0.092* | |
H34B | −0.0671 | 1.2084 | 0.6690 | 0.092* | |
H34C | −0.0248 | 1.0916 | 0.7190 | 0.092* | |
C35 | 0.2230 (5) | 0.4898 (4) | 0.9976 (3) | 0.0529 (12) | |
H35A | 0.2027 | 0.4313 | 0.9811 | 0.079* | |
H35B | 0.2300 | 0.4736 | 1.0594 | 0.079* | |
H35C | 0.3180 | 0.5024 | 0.9615 | 0.079* | |
C36 | 0.8667 (5) | 0.6481 (4) | 0.4637 (3) | 0.0500 (12) | |
H36A | 0.8328 | 0.6433 | 0.4123 | 0.075* | |
H36B | 0.9759 | 0.6380 | 0.4497 | 0.075* | |
H36C | 0.8185 | 0.7167 | 0.4805 | 0.075* | |
C32 | 0.8084 (7) | 0.3072 (4) | 0.8519 (4) | 0.0666 (15) | |
H32A | 0.7601 | 0.2807 | 0.8169 | 0.080* | 0.805 (7) |
H32B | 0.7284 | 0.3460 | 0.8942 | 0.080* | 0.805 (7) |
H32C | 0.8225 | 0.2519 | 0.8177 | 0.080* | 0.195 (7) |
H32D | 0.7030 | 0.3479 | 0.8543 | 0.080* | 0.195 (7) |
C33 | 0.9104 (8) | 0.2148 (5) | 0.9022 (4) | 0.064 (2) | 0.805 (7) |
H33A | 0.9519 | 0.2412 | 0.9408 | 0.077* | 0.805 (7) |
H33B | 0.9955 | 0.1801 | 0.8598 | 0.077* | 0.805 (7) |
Br3 | 0.7988 (2) | 0.11246 (12) | 0.97373 (17) | 0.1112 (7) | 0.805 (7) |
C33' | 0.813 (4) | 0.2485 (9) | 0.9471 (9) | 0.084 (10) | 0.195 (7) |
H33C | 0.7147 | 0.2648 | 0.9874 | 0.101* | 0.195 (7) |
H33D | 0.8913 | 0.2613 | 0.9709 | 0.101* | 0.195 (7) |
Br3' | 0.8668 (15) | 0.1078 (5) | 0.9192 (10) | 0.140 (4) | 0.195 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0899 (5) | 0.0847 (5) | 0.0746 (4) | −0.0008 (4) | −0.0171 (4) | 0.0093 (3) |
Br2 | 0.1028 (6) | 0.1119 (6) | 0.0555 (4) | 0.0031 (4) | 0.0042 (4) | −0.0127 (4) |
O1 | 0.0460 (18) | 0.0381 (17) | 0.0436 (17) | −0.0143 (14) | −0.0007 (14) | −0.0007 (14) |
O2 | 0.065 (2) | 0.0346 (17) | 0.0501 (19) | −0.0107 (15) | 0.0037 (16) | −0.0141 (15) |
O3 | 0.0450 (18) | 0.0458 (18) | 0.0387 (17) | 0.0000 (14) | −0.0016 (14) | −0.0114 (14) |
O4 | 0.0500 (18) | 0.0432 (17) | 0.0381 (17) | −0.0023 (14) | −0.0126 (14) | −0.0012 (14) |
O5 | 0.0401 (16) | 0.0382 (16) | 0.0437 (17) | −0.0014 (13) | −0.0122 (14) | −0.0084 (13) |
O6 | 0.0287 (16) | 0.055 (2) | 0.054 (2) | −0.0058 (14) | 0.0000 (14) | 0.0043 (16) |
C1 | 0.033 (2) | 0.038 (2) | 0.028 (2) | −0.0033 (18) | −0.0097 (17) | −0.0056 (18) |
C2 | 0.029 (2) | 0.041 (3) | 0.030 (2) | −0.0040 (19) | −0.0011 (17) | −0.0033 (18) |
C3 | 0.036 (2) | 0.035 (2) | 0.035 (2) | −0.0036 (19) | −0.0131 (19) | −0.0022 (19) |
C4 | 0.044 (2) | 0.036 (2) | 0.032 (2) | −0.006 (2) | −0.0086 (19) | −0.0063 (19) |
C5 | 0.035 (2) | 0.040 (2) | 0.030 (2) | −0.002 (2) | −0.0041 (18) | −0.0050 (19) |
C6 | 0.029 (2) | 0.035 (2) | 0.031 (2) | −0.0062 (18) | −0.0092 (17) | −0.0022 (18) |
C7 | 0.030 (2) | 0.041 (2) | 0.036 (2) | −0.0045 (18) | −0.0103 (18) | −0.0032 (18) |
C8 | 0.0229 (19) | 0.038 (2) | 0.035 (2) | −0.0169 (18) | −0.0002 (17) | −0.0037 (18) |
C9 | 0.029 (2) | 0.032 (2) | 0.040 (2) | −0.0051 (17) | −0.0032 (18) | −0.0020 (18) |
C10 | 0.034 (2) | 0.037 (2) | 0.037 (2) | −0.0137 (19) | −0.0016 (18) | −0.0045 (19) |
C11 | 0.034 (2) | 0.036 (2) | 0.035 (2) | −0.0143 (19) | −0.0049 (18) | 0.0035 (18) |
C12 | 0.027 (2) | 0.029 (2) | 0.040 (2) | −0.0073 (17) | −0.0007 (18) | 0.0025 (18) |
C13 | 0.025 (2) | 0.031 (2) | 0.039 (2) | −0.0126 (17) | −0.0025 (17) | −0.0044 (18) |
C14 | 0.037 (2) | 0.030 (2) | 0.042 (2) | −0.0138 (18) | −0.0046 (19) | −0.0035 (18) |
C15 | 0.031 (2) | 0.027 (2) | 0.037 (2) | −0.0035 (17) | −0.0034 (18) | −0.0117 (18) |
C16 | 0.041 (2) | 0.029 (2) | 0.034 (2) | −0.0089 (18) | 0.0013 (19) | −0.0056 (17) |
C17 | 0.033 (2) | 0.031 (2) | 0.039 (2) | −0.0021 (18) | −0.0057 (19) | −0.0090 (18) |
C18 | 0.032 (2) | 0.034 (2) | 0.037 (2) | −0.0039 (18) | 0.0027 (18) | −0.0097 (18) |
C19 | 0.036 (2) | 0.031 (2) | 0.033 (2) | −0.0074 (18) | 0.0000 (18) | −0.0015 (17) |
C20 | 0.035 (2) | 0.027 (2) | 0.031 (2) | −0.0037 (17) | −0.0003 (17) | −0.0118 (17) |
C21 | 0.039 (2) | 0.033 (2) | 0.034 (2) | −0.0080 (18) | −0.0043 (18) | −0.0067 (18) |
C22 | 0.039 (2) | 0.043 (3) | 0.044 (3) | −0.012 (2) | −0.008 (2) | −0.002 (2) |
C23 | 0.045 (3) | 0.052 (3) | 0.056 (3) | −0.018 (2) | −0.008 (2) | 0.004 (2) |
C24 | 0.035 (3) | 0.065 (3) | 0.075 (4) | −0.014 (2) | −0.006 (3) | 0.014 (3) |
C25 | 0.068 (4) | 0.084 (4) | 0.086 (4) | −0.042 (3) | −0.020 (3) | 0.016 (3) |
C26 | 0.058 (3) | 0.049 (3) | 0.046 (3) | 0.007 (2) | −0.006 (2) | −0.010 (2) |
C27 | 0.065 (3) | 0.049 (3) | 0.055 (3) | 0.010 (3) | −0.005 (3) | −0.013 (2) |
C28 | 0.076 (4) | 0.086 (4) | 0.068 (4) | −0.030 (3) | 0.015 (3) | −0.029 (3) |
C29 | 0.070 (4) | 0.089 (5) | 0.082 (4) | −0.017 (3) | 0.015 (3) | −0.021 (4) |
C30 | 0.052 (3) | 0.048 (3) | 0.063 (3) | −0.015 (2) | −0.018 (2) | −0.011 (2) |
C31 | 0.048 (3) | 0.063 (3) | 0.054 (3) | −0.014 (2) | −0.014 (2) | −0.014 (2) |
C34 | 0.076 (4) | 0.046 (3) | 0.055 (3) | −0.008 (3) | 0.004 (3) | −0.024 (2) |
C35 | 0.049 (3) | 0.054 (3) | 0.048 (3) | −0.004 (2) | −0.015 (2) | 0.000 (2) |
C36 | 0.038 (3) | 0.056 (3) | 0.050 (3) | −0.016 (2) | 0.002 (2) | −0.005 (2) |
C32 | 0.076 (4) | 0.070 (3) | 0.062 (3) | −0.027 (3) | −0.022 (3) | −0.006 (3) |
C33 | 0.077 (4) | 0.064 (4) | 0.056 (4) | −0.012 (3) | −0.026 (3) | −0.013 (3) |
Br3 | 0.1409 (12) | 0.0680 (8) | 0.1052 (13) | −0.0274 (7) | −0.0157 (10) | 0.0155 (7) |
C33' | 0.087 (13) | 0.088 (13) | 0.086 (13) | −0.024 (9) | −0.022 (9) | −0.023 (9) |
Br3' | 0.182 (7) | 0.099 (4) | 0.141 (7) | −0.004 (4) | −0.054 (6) | −0.042 (4) |
Br1—C25 | 1.929 (6) | C22—C23 | 1.498 (6) |
Br2—C29 | 1.898 (7) | C22—H22A | 0.9700 |
O1—C3 | 1.360 (5) | C22—H22B | 0.9700 |
O1—C22 | 1.427 (5) | C23—C24 | 1.521 (7) |
O2—C4 | 1.376 (5) | C23—H23A | 0.9700 |
O2—C34 | 1.413 (6) | C23—H23B | 0.9700 |
O3—C10 | 1.374 (5) | C24—C25 | 1.501 (7) |
O3—C26 | 1.428 (5) | C24—H24A | 0.9700 |
O4—C11 | 1.370 (5) | C24—H24B | 0.9700 |
O4—C35 | 1.422 (5) | C25—H25A | 0.9700 |
O5—C17 | 1.382 (5) | C25—H25B | 0.9700 |
O5—C30 | 1.433 (5) | C26—C27 | 1.518 (7) |
O6—C18 | 1.362 (5) | C26—H26A | 0.9700 |
O6—C36 | 1.418 (5) | C26—H26B | 0.9700 |
C1—C6 | 1.391 (5) | C27—C28 | 1.522 (8) |
C1—C2 | 1.403 (6) | C27—H27A | 0.9700 |
C1—C21 | 1.515 (6) | C27—H27B | 0.9700 |
C2—C3 | 1.381 (6) | C28—C29 | 1.538 (8) |
C2—H2 | 0.9300 | C28—H28A | 0.9700 |
C3—C4 | 1.404 (6) | C28—H28B | 0.9700 |
C4—C5 | 1.361 (6) | C29—H29A | 0.9700 |
C5—C6 | 1.407 (6) | C29—H29B | 0.9700 |
C5—H5 | 0.9300 | C30—C31 | 1.480 (7) |
C6—C7 | 1.508 (6) | C30—H30A | 0.9700 |
C7—C8 | 1.520 (6) | C30—H30B | 0.9700 |
C7—H7A | 0.9700 | C31—C32 | 1.499 (7) |
C7—H7B | 0.9700 | C31—H31A | 0.9700 |
C8—C13 | 1.387 (5) | C31—H31B | 0.9700 |
C8—C9 | 1.397 (5) | C34—H34A | 0.9600 |
C9—C10 | 1.376 (6) | C34—H34B | 0.9600 |
C9—H9 | 0.9300 | C34—H34C | 0.9600 |
C10—C11 | 1.409 (6) | C35—H35A | 0.9600 |
C11—C12 | 1.367 (6) | C35—H35B | 0.9600 |
C12—C13 | 1.397 (6) | C35—H35C | 0.9600 |
C12—H12 | 0.9300 | C36—H36A | 0.9600 |
C13—C14 | 1.524 (5) | C36—H36B | 0.9600 |
C14—C15 | 1.518 (5) | C36—H36C | 0.9600 |
C14—H14A | 0.9700 | C32—C33 | 1.520 (7) |
C14—H14B | 0.9700 | C32—C33' | 1.527 (10) |
C15—C16 | 1.395 (6) | C32—H32A | 0.9700 |
C15—C20 | 1.397 (6) | C32—H32B | 0.9700 |
C16—C17 | 1.377 (6) | C32—H32C | 0.9700 |
C16—H16 | 0.9300 | C32—H32D | 0.9700 |
C17—C18 | 1.397 (6) | C33—Br3 | 1.941 (6) |
C18—C19 | 1.375 (6) | C33—H33A | 0.9700 |
C19—C20 | 1.398 (6) | C33—H33B | 0.9700 |
C19—H19 | 0.9300 | C33'—Br3' | 1.923 (10) |
C20—C21 | 1.514 (5) | C33'—H32B | 1.5036 |
C21—H21A | 0.9700 | C33'—H33C | 0.9700 |
C21—H21B | 0.9700 | C33'—H33D | 0.9700 |
C3—O1—C22 | 117.2 (3) | C24—C25—H25A | 109.2 |
C4—O2—C34 | 116.7 (4) | Br1—C25—H25A | 109.2 |
C10—O3—C26 | 117.4 (3) | C24—C25—H25B | 109.2 |
C11—O4—C35 | 116.3 (3) | Br1—C25—H25B | 109.2 |
C17—O5—C30 | 114.7 (3) | H25A—C25—H25B | 107.9 |
C18—O6—C36 | 117.6 (3) | O3—C26—C27 | 107.4 (4) |
C6—C1—C2 | 118.5 (4) | O3—C26—H26A | 110.2 |
C6—C1—C21 | 123.6 (4) | C27—C26—H26A | 110.2 |
C2—C1—C21 | 117.9 (4) | O3—C26—H26B | 110.2 |
C3—C2—C1 | 122.7 (4) | C27—C26—H26B | 110.2 |
C3—C2—H2 | 118.6 | H26A—C26—H26B | 108.5 |
C1—C2—H2 | 118.6 | C26—C27—C28 | 113.3 (4) |
O1—C3—C2 | 125.1 (4) | C26—C27—H27A | 108.9 |
O1—C3—C4 | 116.7 (4) | C28—C27—H27A | 108.9 |
C2—C3—C4 | 118.2 (4) | C26—C27—H27B | 108.9 |
C5—C4—O2 | 125.5 (4) | C28—C27—H27B | 108.9 |
C5—C4—C3 | 119.4 (4) | H27A—C27—H27B | 107.7 |
O2—C4—C3 | 115.1 (4) | C27—C28—C29 | 112.5 (5) |
C4—C5—C6 | 122.9 (4) | C27—C28—H28A | 109.1 |
C4—C5—H5 | 118.5 | C29—C28—H28A | 109.1 |
C6—C5—H5 | 118.5 | C27—C28—H28B | 109.1 |
C1—C6—C5 | 118.1 (4) | C29—C28—H28B | 109.1 |
C1—C6—C7 | 124.0 (4) | H28A—C28—H28B | 107.8 |
C5—C6—C7 | 117.9 (4) | C28—C29—Br2 | 112.2 (4) |
C6—C7—C8 | 113.7 (3) | C28—C29—H29A | 109.2 |
C6—C7—H7A | 108.8 | Br2—C29—H29A | 109.2 |
C8—C7—H7A | 108.8 | C28—C29—H29B | 109.2 |
C6—C7—H7B | 108.8 | Br2—C29—H29B | 109.2 |
C8—C7—H7B | 108.8 | H29A—C29—H29B | 107.9 |
H7A—C7—H7B | 107.7 | O5—C30—C31 | 109.2 (4) |
C13—C8—C9 | 118.6 (4) | O5—C30—H30A | 109.8 |
C13—C8—C7 | 123.6 (4) | C31—C30—H30A | 109.8 |
C9—C8—C7 | 117.8 (4) | O5—C30—H30B | 109.8 |
C10—C9—C8 | 122.3 (4) | C31—C30—H30B | 109.8 |
C10—C9—H9 | 118.9 | H30A—C30—H30B | 108.3 |
C8—C9—H9 | 118.9 | C30—C31—C32 | 114.0 (4) |
O3—C10—C9 | 125.3 (4) | C30—C31—H31A | 108.7 |
O3—C10—C11 | 115.8 (4) | C32—C31—H31A | 108.7 |
C9—C10—C11 | 118.9 (4) | C30—C31—H31B | 108.7 |
C12—C11—O4 | 126.0 (4) | C32—C31—H31B | 108.7 |
C12—C11—C10 | 118.5 (4) | H31A—C31—H31B | 107.6 |
O4—C11—C10 | 115.5 (4) | O2—C34—H34A | 109.5 |
C11—C12—C13 | 122.8 (4) | O2—C34—H34B | 109.5 |
C11—C12—H12 | 118.6 | H34A—C34—H34B | 109.5 |
C13—C12—H12 | 118.6 | O2—C34—H34C | 109.5 |
C8—C13—C12 | 118.7 (4) | H34A—C34—H34C | 109.5 |
C8—C13—C14 | 123.2 (4) | H34B—C34—H34C | 109.5 |
C12—C13—C14 | 118.1 (3) | O4—C35—H35A | 109.5 |
C15—C14—C13 | 114.4 (3) | O4—C35—H35B | 109.5 |
C15—C14—H14A | 108.7 | H35A—C35—H35B | 109.5 |
C13—C14—H14A | 108.7 | O4—C35—H35C | 109.5 |
C15—C14—H14B | 108.7 | H35A—C35—H35C | 109.5 |
C13—C14—H14B | 108.7 | H35B—C35—H35C | 109.5 |
H14A—C14—H14B | 107.6 | O6—C36—H36A | 109.5 |
C16—C15—C20 | 118.1 (4) | O6—C36—H36B | 109.5 |
C16—C15—C14 | 117.8 (4) | H36A—C36—H36B | 109.5 |
C20—C15—C14 | 124.1 (4) | O6—C36—H36C | 109.5 |
C17—C16—C15 | 122.8 (4) | H36A—C36—H36C | 109.5 |
C17—C16—H16 | 118.6 | H36B—C36—H36C | 109.5 |
C15—C16—H16 | 118.6 | C31—C32—C33 | 110.4 (5) |
C16—C17—O5 | 119.1 (4) | C31—C32—C33' | 131.4 (14) |
C16—C17—C18 | 119.0 (4) | C33—C32—C33' | 40.2 (11) |
O5—C17—C18 | 121.7 (4) | C31—C32—H32A | 109.6 |
O6—C18—C19 | 125.5 (4) | C33—C32—H32A | 109.5 |
O6—C18—C17 | 115.6 (4) | C33'—C32—H32A | 116.6 |
C19—C18—C17 | 118.8 (4) | C31—C32—H32B | 109.6 |
C18—C19—C20 | 122.6 (4) | C33—C32—H32B | 109.6 |
C18—C19—H19 | 118.7 | C33'—C32—H32B | 70.0 |
C20—C19—H19 | 118.7 | H32A—C32—H32B | 108.1 |
C15—C20—C19 | 118.7 (4) | C31—C32—H32C | 104.2 |
C15—C20—C21 | 123.1 (3) | C33—C32—H32C | 79.2 |
C19—C20—C21 | 118.2 (3) | C33'—C32—H32C | 104.3 |
C20—C21—C1 | 114.0 (3) | H32A—C32—H32C | 35.9 |
C20—C21—H21A | 108.8 | H32B—C32—H32C | 138.5 |
C1—C21—H21A | 108.8 | C31—C32—H32D | 104.2 |
C20—C21—H21B | 108.8 | C33—C32—H32D | 142.7 |
C1—C21—H21B | 108.8 | C33'—C32—H32D | 104.9 |
H21A—C21—H21B | 107.6 | H32A—C32—H32D | 69.8 |
O1—C22—C23 | 109.3 (4) | H32B—C32—H32D | 43.4 |
O1—C22—H22A | 109.8 | H32C—C32—H32D | 105.5 |
C23—C22—H22A | 109.8 | C32—C33—Br3 | 111.7 (4) |
O1—C22—H22B | 109.8 | C32—C33—H33A | 109.3 |
C23—C22—H22B | 109.8 | Br3—C33—H33A | 109.3 |
H22A—C22—H22B | 108.3 | C32—C33—H33B | 109.3 |
C22—C23—C24 | 110.8 (4) | Br3—C33—H33B | 109.3 |
C22—C23—H23A | 109.5 | H33A—C33—H33B | 107.9 |
C24—C23—H23A | 109.5 | C32—C33'—Br3' | 96.6 (8) |
C22—C23—H23B | 109.5 | C32—C33'—H32B | 37.3 |
C24—C23—H23B | 109.5 | Br3'—C33'—H32B | 124.9 |
H23A—C23—H23B | 108.1 | C32—C33'—H33C | 112.4 |
C25—C24—C23 | 114.3 (5) | Br3'—C33'—H33C | 112.4 |
C25—C24—H24A | 108.7 | H32B—C33'—H33C | 78.3 |
C23—C24—H24A | 108.7 | C32—C33'—H33D | 112.4 |
C25—C24—H24B | 108.7 | Br3'—C33'—H33D | 112.4 |
C23—C24—H24B | 108.7 | H32B—C33'—H33D | 113.3 |
H24A—C24—H24B | 107.6 | H33C—C33'—H33D | 110.0 |
C24—C25—Br1 | 111.9 (4) | ||
C6—C1—C2—C3 | 1.5 (6) | C8—C13—C14—C15 | 97.5 (5) |
C21—C1—C2—C3 | −178.5 (4) | C12—C13—C14—C15 | −82.0 (4) |
C22—O1—C3—C2 | 7.2 (6) | C13—C14—C15—C16 | 86.4 (4) |
C22—O1—C3—C4 | −171.4 (4) | C13—C14—C15—C20 | −93.8 (5) |
C1—C2—C3—O1 | −176.2 (4) | C20—C15—C16—C17 | 0.3 (6) |
C1—C2—C3—C4 | 2.4 (6) | C14—C15—C16—C17 | −179.9 (4) |
C34—O2—C4—C5 | 2.8 (6) | C15—C16—C17—O5 | −174.8 (4) |
C34—O2—C4—C3 | −179.0 (4) | C15—C16—C17—C18 | 0.0 (6) |
O1—C3—C4—C5 | 174.5 (4) | C30—O5—C17—C16 | −107.7 (4) |
C2—C3—C4—C5 | −4.2 (6) | C30—O5—C17—C18 | 77.6 (5) |
O1—C3—C4—O2 | −3.7 (5) | C36—O6—C18—C19 | 7.5 (6) |
C2—C3—C4—O2 | 177.6 (4) | C36—O6—C18—C17 | −174.4 (4) |
O2—C4—C5—C6 | −179.8 (4) | C16—C17—C18—O6 | −178.3 (4) |
C3—C4—C5—C6 | 2.1 (6) | O5—C17—C18—O6 | −3.6 (6) |
C2—C1—C6—C5 | −3.5 (6) | C16—C17—C18—C19 | −0.1 (6) |
C21—C1—C6—C5 | 176.5 (4) | O5—C17—C18—C19 | 174.6 (4) |
C2—C1—C6—C7 | 175.2 (4) | O6—C18—C19—C20 | 177.9 (4) |
C21—C1—C6—C7 | −4.8 (6) | C17—C18—C19—C20 | −0.1 (6) |
C4—C5—C6—C1 | 1.8 (6) | C16—C15—C20—C19 | −0.5 (5) |
C4—C5—C6—C7 | −177.0 (4) | C14—C15—C20—C19 | 179.8 (4) |
C1—C6—C7—C8 | 98.5 (5) | C16—C15—C20—C21 | 179.0 (3) |
C5—C6—C7—C8 | −82.8 (4) | C14—C15—C20—C21 | −0.8 (6) |
C6—C7—C8—C13 | −90.2 (5) | C18—C19—C20—C15 | 0.4 (6) |
C6—C7—C8—C9 | 87.3 (4) | C18—C19—C20—C21 | −179.1 (4) |
C13—C8—C9—C10 | 2.6 (6) | C15—C20—C21—C1 | 94.2 (5) |
C7—C8—C9—C10 | −175.1 (4) | C19—C20—C21—C1 | −86.3 (4) |
C26—O3—C10—C9 | 5.9 (6) | C6—C1—C21—C20 | −92.5 (5) |
C26—O3—C10—C11 | −173.8 (4) | C2—C1—C21—C20 | 87.6 (4) |
C8—C9—C10—O3 | −177.9 (4) | C3—O1—C22—C23 | 171.0 (4) |
C8—C9—C10—C11 | 1.9 (6) | O1—C22—C23—C24 | 173.9 (4) |
C35—O4—C11—C12 | 5.3 (6) | C22—C23—C24—C25 | 174.4 (4) |
C35—O4—C11—C10 | −176.8 (4) | C23—C24—C25—Br1 | −72.2 (6) |
O3—C10—C11—C12 | 174.6 (3) | C10—O3—C26—C27 | 173.9 (4) |
C9—C10—C11—C12 | −5.1 (6) | O3—C26—C27—C28 | −65.1 (6) |
O3—C10—C11—O4 | −3.4 (5) | C26—C27—C28—C29 | −175.7 (5) |
C9—C10—C11—O4 | 176.8 (4) | C27—C28—C29—Br2 | −70.0 (6) |
O4—C11—C12—C13 | −178.1 (4) | C17—O5—C30—C31 | 165.8 (4) |
C10—C11—C12—C13 | 4.1 (6) | O5—C30—C31—C32 | −59.2 (6) |
C9—C8—C13—C12 | −3.7 (5) | C30—C31—C32—C33 | 175.3 (5) |
C7—C8—C13—C12 | 173.8 (4) | C30—C31—C32—C33' | −144.1 (12) |
C9—C8—C13—C14 | 176.8 (3) | C31—C32—C33—Br3 | −175.1 (4) |
C7—C8—C13—C14 | −5.7 (6) | C33'—C32—C33—Br3 | 54.1 (16) |
C11—C12—C13—C8 | 0.4 (6) | C31—C32—C33'—Br3' | −118.1 (11) |
C11—C12—C13—C14 | 179.9 (3) | C33—C32—C33'—Br3' | −47.1 (7) |