Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024619/ww6126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024619/ww6126Isup2.hkl |
CCDC reference: 227780
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.
C30H33Br3O6 | F(000) = 1464 |
Mr = 729.29 | Dx = 1.609 Mg m−3 |
Monoclinic, P21/n | Melting point = 420–422 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 14.585 (3) Å | Cell parameters from 882 reflections |
b = 8.3893 (19) Å | θ = 3.1–23.7° |
c = 24.881 (6) Å | µ = 4.06 mm−1 |
β = 98.507 (4)° | T = 293 K |
V = 3010.8 (12) Å3 | Block, colorless |
Z = 4 | 0.38 × 0.32 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 6129 independent reflections |
Radiation source: fine-focus sealed tube | 3693 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
φ and ω scans | θmax = 26.4°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −17→18 |
Tmin = 0.263, Tmax = 0.666 | k = −9→10 |
18616 measured reflections | l = −31→30 |
Refinement on F2 | 80 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.164 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.69 e Å−3 |
6129 reflections | Δρmin = −0.85 e Å−3 |
383 parameters |
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 | 0.65826 (5) | 0.90148 (9) | 0.48562 (3) | 0.0711 (3) | |
Br3 | 1.11988 (4) | 0.58579 (9) | 0.14199 (3) | 0.0685 (2) | |
O1 | 0.4949 (2) | 0.7191 (4) | 0.35282 (14) | 0.0439 (9) | |
O2 | 0.3535 (2) | 0.5614 (4) | 0.30468 (14) | 0.0440 (9) | |
O3 | 0.3705 (2) | 0.1854 (4) | 0.07938 (17) | 0.0539 (11) | |
O4 | 0.5328 (2) | 0.1778 (4) | 0.04922 (14) | 0.0398 (8) | |
O5 | 0.9078 (2) | 0.6918 (4) | 0.15013 (15) | 0.0429 (9) | |
O6 | 0.8912 (2) | 0.8507 (5) | 0.24369 (16) | 0.0506 (10) | |
C1 | 0.5590 (3) | 0.9598 (5) | 0.1801 (2) | 0.0310 (11) | |
H1A | 0.5730 | 1.0574 | 0.2006 | 0.037* | |
H1B | 0.5237 | 0.9881 | 0.1452 | 0.037* | |
C2 | 0.5005 (3) | 0.8531 (5) | 0.2104 (2) | 0.0307 (11) | |
C3 | 0.5240 (3) | 0.8369 (6) | 0.2668 (2) | 0.0330 (11) | |
H3 | 0.5742 | 0.8945 | 0.2843 | 0.040* | |
C4 | 0.4765 (3) | 0.7404 (5) | 0.2973 (2) | 0.0317 (11) | |
C5 | 0.3994 (3) | 0.6529 (5) | 0.2711 (2) | 0.0330 (11) | |
C6 | 0.3760 (3) | 0.6673 (5) | 0.2160 (2) | 0.0313 (11) | |
H6 | 0.3253 | 0.6104 | 0.1988 | 0.038* | |
C7 | 0.4252 (3) | 0.7641 (5) | 0.18457 (19) | 0.0281 (10) | |
C8 | 0.3962 (3) | 0.7602 (6) | 0.12277 (19) | 0.0324 (11) | |
H8A | 0.3291 | 0.7586 | 0.1143 | 0.039* | |
H8B | 0.4185 | 0.8553 | 0.1067 | 0.039* | |
C9 | 0.4361 (3) | 0.6131 (5) | 0.09909 (19) | 0.0291 (10) | |
C10 | 0.3849 (3) | 0.4732 (6) | 0.09778 (19) | 0.0323 (11) | |
H10 | 0.3263 | 0.4765 | 0.1083 | 0.039* | |
C11 | 0.4176 (3) | 0.3299 (6) | 0.0816 (2) | 0.0342 (11) | |
C12 | 0.5057 (3) | 0.3247 (5) | 0.06471 (18) | 0.0304 (11) | |
C13 | 0.5552 (3) | 0.4641 (5) | 0.06455 (17) | 0.0262 (10) | |
H13 | 0.6129 | 0.4611 | 0.0528 | 0.031* | |
C14 | 0.5225 (3) | 0.6113 (5) | 0.08135 (17) | 0.0251 (10) | |
C15 | 0.5805 (3) | 0.7605 (6) | 0.07772 (18) | 0.0302 (10) | |
H15A | 0.5394 | 0.8520 | 0.0750 | 0.036* | |
H15B | 0.6073 | 0.7553 | 0.0443 | 0.036* | |
C16 | 0.6588 (3) | 0.7896 (5) | 0.12461 (18) | 0.0255 (10) | |
C17 | 0.7464 (3) | 0.7284 (5) | 0.11996 (19) | 0.0310 (11) | |
H17 | 0.7536 | 0.6690 | 0.0893 | 0.037* | |
C18 | 0.8226 (3) | 0.7524 (5) | 0.1590 (2) | 0.0314 (11) | |
C19 | 0.8127 (3) | 0.8368 (6) | 0.2060 (2) | 0.0331 (11) | |
C20 | 0.7271 (3) | 0.9028 (6) | 0.2107 (2) | 0.0328 (11) | |
H20 | 0.7208 | 0.9632 | 0.2413 | 0.039* | |
C21 | 0.6496 (3) | 0.8809 (5) | 0.17071 (18) | 0.0267 (10) | |
C22 | 0.5720 (3) | 0.8034 (6) | 0.3820 (2) | 0.0416 (13) | |
H22A | 0.5723 | 0.9136 | 0.3702 | 0.050* | |
H22B | 0.6301 | 0.7539 | 0.3766 | 0.050* | |
C23 | 0.5579 (4) | 0.7929 (7) | 0.4407 (2) | 0.0529 (15) | |
H23A | 0.5562 | 0.6820 | 0.4515 | 0.063* | |
H23B | 0.4992 | 0.8416 | 0.4453 | 0.063* | |
C24 | 0.2809 (4) | 0.4632 (8) | 0.2787 (3) | 0.0631 (18) | |
H24A | 0.2320 | 0.5289 | 0.2605 | 0.095* | |
H24B | 0.2573 | 0.3984 | 0.3053 | 0.095* | |
H24C | 0.3043 | 0.3959 | 0.2526 | 0.095* | |
C25 | 0.2979 (5) | 0.1643 (10) | 0.1116 (3) | 0.042 (2) | 0.696 (11) |
H25A | 0.3101 | 0.2282 | 0.1444 | 0.051* | 0.696 (11) |
H25B | 0.2941 | 0.0534 | 0.1220 | 0.051* | 0.696 (11) |
C26 | 0.2076 (5) | 0.2162 (9) | 0.0777 (3) | 0.046 (2) | 0.696 (11) |
H26A | 0.2144 | 0.3231 | 0.0640 | 0.055* | 0.696 (11) |
H26B | 0.1588 | 0.2182 | 0.1003 | 0.055* | 0.696 (11) |
Br2 | 0.1730 (3) | 0.0703 (6) | 0.0167 (2) | 0.0966 (12) | 0.696 (11) |
C25' | 0.2781 (8) | 0.212 (2) | 0.0930 (8) | 0.047 (6) | 0.304 (11) |
H25C | 0.2537 | 0.3115 | 0.0767 | 0.056* | 0.304 (11) |
H25D | 0.2818 | 0.2220 | 0.1321 | 0.056* | 0.304 (11) |
C26' | 0.2124 (11) | 0.077 (2) | 0.0729 (5) | 0.059 (6) | 0.304 (11) |
H26C | 0.1591 | 0.0784 | 0.0921 | 0.071* | 0.304 (11) |
H26D | 0.2438 | −0.0248 | 0.0803 | 0.071* | 0.304 (11) |
Br2' | 0.1716 (6) | 0.0983 (9) | −0.0043 (4) | 0.0811 (18) | 0.304 (11) |
C27 | 0.6227 (4) | 0.1648 (6) | 0.0339 (3) | 0.0506 (15) | |
H27A | 0.6287 | 0.2403 | 0.0056 | 0.076* | |
H27B | 0.6314 | 0.0589 | 0.0209 | 0.076* | |
H27C | 0.6687 | 0.1864 | 0.0647 | 0.076* | |
C28 | 0.9743 (4) | 0.8129 (7) | 0.1445 (3) | 0.0653 (19) | |
H28A | 1.0078 | 0.8405 | 0.1799 | 0.078* | |
H28B | 0.9431 | 0.9078 | 0.1288 | 0.078* | |
C29 | 1.0409 (4) | 0.7539 (8) | 0.1085 (3) | 0.0692 (19) | |
H29A | 1.0791 | 0.8420 | 0.0997 | 0.083* | |
H29B | 1.0062 | 0.7147 | 0.0748 | 0.083* | |
C30 | 0.8844 (4) | 0.9403 (8) | 0.2919 (2) | 0.0619 (17) | |
H30A | 0.8647 | 1.0470 | 0.2822 | 0.093* | |
H30B | 0.9439 | 0.9435 | 0.3143 | 0.093* | |
H30C | 0.8402 | 0.8907 | 0.3116 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0835 (5) | 0.0818 (5) | 0.0439 (4) | −0.0240 (4) | −0.0038 (3) | −0.0086 (3) |
Br3 | 0.0367 (3) | 0.0777 (5) | 0.0906 (6) | 0.0047 (3) | 0.0079 (3) | −0.0040 (4) |
O1 | 0.052 (2) | 0.047 (2) | 0.033 (2) | −0.0161 (18) | 0.0047 (16) | 0.0001 (17) |
O2 | 0.046 (2) | 0.046 (2) | 0.041 (2) | −0.0191 (17) | 0.0101 (16) | −0.0021 (17) |
O3 | 0.054 (2) | 0.039 (2) | 0.076 (3) | −0.0208 (18) | 0.035 (2) | −0.021 (2) |
O4 | 0.048 (2) | 0.0258 (18) | 0.049 (2) | −0.0005 (15) | 0.0187 (17) | −0.0040 (16) |
O5 | 0.0287 (17) | 0.0329 (19) | 0.067 (3) | −0.0020 (15) | 0.0058 (16) | −0.0119 (18) |
O6 | 0.038 (2) | 0.061 (2) | 0.047 (2) | 0.0007 (18) | −0.0083 (16) | −0.0140 (19) |
C1 | 0.037 (3) | 0.021 (2) | 0.035 (3) | −0.003 (2) | 0.005 (2) | −0.003 (2) |
C2 | 0.031 (2) | 0.019 (2) | 0.042 (3) | 0.0052 (19) | 0.008 (2) | −0.004 (2) |
C3 | 0.031 (2) | 0.031 (3) | 0.037 (3) | −0.006 (2) | 0.004 (2) | −0.006 (2) |
C4 | 0.035 (2) | 0.026 (2) | 0.034 (3) | 0.000 (2) | 0.006 (2) | −0.004 (2) |
C5 | 0.031 (2) | 0.026 (2) | 0.043 (3) | 0.002 (2) | 0.009 (2) | −0.001 (2) |
C6 | 0.024 (2) | 0.026 (2) | 0.044 (3) | 0.0019 (19) | 0.005 (2) | −0.002 (2) |
C7 | 0.023 (2) | 0.021 (2) | 0.040 (3) | 0.0070 (18) | 0.003 (2) | −0.002 (2) |
C8 | 0.025 (2) | 0.030 (3) | 0.041 (3) | 0.007 (2) | −0.001 (2) | 0.001 (2) |
C9 | 0.026 (2) | 0.030 (3) | 0.029 (3) | 0.002 (2) | −0.0040 (19) | 0.001 (2) |
C10 | 0.027 (2) | 0.038 (3) | 0.033 (3) | −0.002 (2) | 0.007 (2) | −0.005 (2) |
C11 | 0.034 (3) | 0.035 (3) | 0.034 (3) | −0.010 (2) | 0.006 (2) | −0.005 (2) |
C12 | 0.032 (2) | 0.031 (3) | 0.026 (3) | 0.003 (2) | −0.0015 (19) | 0.001 (2) |
C13 | 0.025 (2) | 0.036 (3) | 0.016 (2) | −0.005 (2) | −0.0008 (17) | 0.0029 (19) |
C14 | 0.026 (2) | 0.029 (2) | 0.017 (2) | −0.0013 (19) | −0.0050 (17) | 0.0015 (19) |
C15 | 0.035 (2) | 0.033 (3) | 0.022 (3) | −0.003 (2) | 0.0033 (19) | −0.002 (2) |
C16 | 0.031 (2) | 0.021 (2) | 0.024 (3) | −0.0051 (19) | 0.0024 (18) | 0.0015 (19) |
C17 | 0.039 (3) | 0.025 (2) | 0.030 (3) | −0.005 (2) | 0.009 (2) | −0.008 (2) |
C18 | 0.029 (2) | 0.019 (2) | 0.045 (3) | −0.0022 (19) | 0.003 (2) | −0.003 (2) |
C19 | 0.032 (2) | 0.031 (3) | 0.033 (3) | −0.005 (2) | −0.005 (2) | −0.006 (2) |
C20 | 0.038 (3) | 0.032 (3) | 0.028 (3) | −0.008 (2) | 0.004 (2) | −0.007 (2) |
C21 | 0.032 (2) | 0.018 (2) | 0.030 (3) | −0.0035 (18) | 0.0065 (19) | 0.0016 (19) |
C22 | 0.041 (3) | 0.043 (3) | 0.038 (3) | −0.005 (2) | 0.000 (2) | 0.000 (2) |
C23 | 0.059 (3) | 0.053 (4) | 0.043 (4) | −0.013 (3) | −0.004 (3) | 0.003 (3) |
C24 | 0.057 (4) | 0.062 (4) | 0.070 (5) | −0.032 (3) | 0.010 (3) | 0.000 (3) |
C25 | 0.051 (5) | 0.031 (5) | 0.049 (6) | −0.001 (4) | 0.019 (4) | 0.012 (4) |
C26 | 0.054 (5) | 0.033 (5) | 0.055 (6) | 0.005 (4) | 0.017 (4) | −0.009 (4) |
Br2 | 0.0834 (12) | 0.100 (2) | 0.109 (3) | −0.0300 (13) | 0.0213 (15) | −0.0476 (17) |
C25' | 0.060 (9) | 0.032 (9) | 0.049 (9) | −0.021 (7) | 0.012 (7) | 0.006 (7) |
C26' | 0.063 (11) | 0.058 (13) | 0.057 (13) | 0.007 (10) | 0.010 (9) | 0.009 (10) |
Br2' | 0.070 (2) | 0.071 (2) | 0.101 (4) | 0.0071 (18) | 0.008 (3) | 0.012 (3) |
C27 | 0.051 (3) | 0.036 (3) | 0.069 (4) | 0.011 (3) | 0.023 (3) | 0.003 (3) |
C28 | 0.041 (3) | 0.039 (3) | 0.121 (6) | −0.006 (3) | 0.027 (3) | −0.013 (4) |
C29 | 0.052 (4) | 0.073 (5) | 0.086 (5) | 0.000 (3) | 0.020 (3) | 0.016 (4) |
C30 | 0.057 (4) | 0.082 (5) | 0.042 (4) | −0.003 (3) | −0.009 (3) | −0.020 (3) |
Br1—C23 | 1.934 (5) | C15—H15A | 0.9700 |
Br3—C29 | 1.930 (6) | C15—H15B | 0.9700 |
O1—C4 | 1.379 (6) | C16—C17 | 1.398 (6) |
O1—C22 | 1.432 (6) | C16—C21 | 1.402 (6) |
O2—C5 | 1.379 (6) | C17—C18 | 1.379 (6) |
O2—C24 | 1.420 (6) | C17—H17 | 0.9300 |
O3—C11 | 1.389 (6) | C18—C19 | 1.393 (7) |
O3—C25 | 1.431 (7) | C19—C20 | 1.387 (6) |
O3—C25' | 1.456 (10) | C20—C21 | 1.404 (6) |
O4—C12 | 1.368 (6) | C20—H20 | 0.9300 |
O4—C27 | 1.424 (6) | C22—C23 | 1.507 (7) |
O5—C18 | 1.390 (5) | C22—H22A | 0.9700 |
O5—C28 | 1.426 (6) | C22—H22B | 0.9700 |
O6—C19 | 1.372 (5) | C23—H23A | 0.9700 |
O6—C30 | 1.432 (7) | C23—H23B | 0.9700 |
C1—C2 | 1.513 (7) | C24—H24A | 0.9600 |
C1—C21 | 1.525 (6) | C24—H24B | 0.9600 |
C1—H1A | 0.9700 | C24—H24C | 0.9600 |
C1—H1B | 0.9700 | C25—C26 | 1.519 (8) |
C2—C3 | 1.402 (7) | C25—H25A | 0.9700 |
C2—C7 | 1.403 (6) | C25—H25B | 0.9700 |
C3—C4 | 1.367 (7) | C26—Br2 | 1.958 (6) |
C3—H3 | 0.9300 | C26—H26A | 0.9700 |
C4—C5 | 1.419 (6) | C26—H26B | 0.9700 |
C5—C6 | 1.367 (7) | C25'—C26' | 1.524 (9) |
C6—C7 | 1.397 (6) | C25'—H25C | 0.9700 |
C6—H6 | 0.9300 | C25'—H25D | 0.9700 |
C7—C8 | 1.534 (6) | C26'—Br2' | 1.935 (9) |
C8—C9 | 1.520 (6) | C26'—H26C | 0.9700 |
C8—H8A | 0.9700 | C26'—H26D | 0.9700 |
C8—H8B | 0.9700 | C27—H27A | 0.9600 |
C9—C10 | 1.389 (6) | C27—H27B | 0.9600 |
C9—C14 | 1.395 (6) | C27—H27C | 0.9600 |
C10—C11 | 1.375 (7) | C28—C29 | 1.498 (9) |
C10—H10 | 0.9300 | C28—H28A | 0.9700 |
C11—C12 | 1.410 (6) | C28—H28B | 0.9700 |
C12—C13 | 1.374 (6) | C29—H29A | 0.9700 |
C13—C14 | 1.410 (6) | C29—H29B | 0.9700 |
C13—H13 | 0.9300 | C30—H30A | 0.9600 |
C14—C15 | 1.522 (6) | C30—H30B | 0.9600 |
C15—C16 | 1.526 (6) | C30—H30C | 0.9600 |
C4—O1—C22 | 117.8 (4) | C20—C19—C18 | 118.7 (4) |
C5—O2—C24 | 116.3 (4) | C19—C20—C21 | 122.0 (4) |
C11—O3—C25 | 119.2 (5) | C19—C20—H20 | 119.0 |
C11—O3—C25' | 109.0 (7) | C21—C20—H20 | 119.0 |
C25—O3—C25' | 25.9 (8) | C16—C21—C20 | 119.1 (4) |
C12—O4—C27 | 117.4 (4) | C16—C21—C1 | 123.5 (4) |
C18—O5—C28 | 113.1 (4) | C20—C21—C1 | 117.4 (4) |
C19—O6—C30 | 117.6 (4) | O1—C22—C23 | 104.6 (4) |
C2—C1—C21 | 112.6 (4) | O1—C22—H22A | 110.8 |
C2—C1—H1A | 109.1 | C23—C22—H22A | 110.8 |
C21—C1—H1A | 109.1 | O1—C22—H22B | 110.8 |
C2—C1—H1B | 109.1 | C23—C22—H22B | 110.8 |
C21—C1—H1B | 109.1 | H22A—C22—H22B | 108.9 |
H1A—C1—H1B | 107.8 | C22—C23—Br1 | 109.4 (4) |
C3—C2—C7 | 117.7 (4) | C22—C23—H23A | 109.8 |
C3—C2—C1 | 119.0 (4) | Br1—C23—H23A | 109.8 |
C7—C2—C1 | 123.2 (4) | C22—C23—H23B | 109.8 |
C4—C3—C2 | 123.0 (4) | Br1—C23—H23B | 109.8 |
C4—C3—H3 | 118.5 | H23A—C23—H23B | 108.2 |
C2—C3—H3 | 118.5 | O2—C24—H24A | 109.5 |
C3—C4—O1 | 126.4 (4) | O2—C24—H24B | 109.5 |
C3—C4—C5 | 118.9 (5) | H24A—C24—H24B | 109.5 |
O1—C4—C5 | 114.7 (4) | O2—C24—H24C | 109.5 |
C6—C5—O2 | 125.8 (4) | H24A—C24—H24C | 109.5 |
C6—C5—C4 | 118.6 (4) | H24B—C24—H24C | 109.5 |
O2—C5—C4 | 115.5 (4) | O3—C25—C26 | 107.9 (6) |
C5—C6—C7 | 122.7 (4) | O3—C25—H25A | 110.1 |
C5—C6—H6 | 118.7 | C26—C25—H25A | 110.1 |
C7—C6—H6 | 118.7 | O3—C25—H25B | 110.1 |
C6—C7—C2 | 119.0 (4) | C26—C25—H25B | 110.1 |
C6—C7—C8 | 117.5 (4) | H25A—C25—H25B | 108.4 |
C2—C7—C8 | 123.4 (4) | C25—C26—Br2 | 110.7 (5) |
C9—C8—C7 | 110.0 (3) | C25—C26—H26A | 109.5 |
C9—C8—H8A | 109.7 | Br2—C26—H26A | 109.5 |
C7—C8—H8A | 109.7 | C25—C26—H26B | 109.5 |
C9—C8—H8B | 109.7 | Br2—C26—H26B | 109.5 |
C7—C8—H8B | 109.7 | H26A—C26—H26B | 108.1 |
H8A—C8—H8B | 108.2 | O3—C25'—C26' | 111.6 (11) |
C10—C9—C14 | 119.4 (4) | O3—C25'—H25C | 109.3 |
C10—C9—C8 | 117.4 (4) | C26'—C25'—H25C | 109.3 |
C14—C9—C8 | 123.1 (4) | O3—C25'—H25D | 109.3 |
C11—C10—C9 | 122.5 (4) | C26'—C25'—H25D | 109.3 |
C11—C10—H10 | 118.7 | H25C—C25'—H25D | 108.0 |
C9—C10—H10 | 118.7 | C25'—C26'—Br2' | 109.9 (10) |
C10—C11—O3 | 125.7 (4) | C25'—C26'—H26C | 109.7 |
C10—C11—C12 | 118.9 (4) | Br2'—C26'—H26C | 109.7 |
O3—C11—C12 | 115.3 (4) | C25'—C26'—H26D | 109.7 |
O4—C12—C13 | 126.3 (4) | Br2'—C26'—H26D | 109.7 |
O4—C12—C11 | 115.2 (4) | H26C—C26'—H26D | 108.2 |
C13—C12—C11 | 118.5 (4) | O4—C27—H27A | 109.5 |
C12—C13—C14 | 122.9 (4) | O4—C27—H27B | 109.5 |
C12—C13—H13 | 118.6 | H27A—C27—H27B | 109.5 |
C14—C13—H13 | 118.6 | O4—C27—H27C | 109.5 |
C9—C14—C13 | 117.7 (4) | H27A—C27—H27C | 109.5 |
C9—C14—C15 | 123.1 (4) | H27B—C27—H27C | 109.5 |
C13—C14—C15 | 119.2 (4) | O5—C28—C29 | 109.5 (5) |
C14—C15—C16 | 116.5 (4) | O5—C28—H28A | 109.8 |
C14—C15—H15A | 108.2 | C29—C28—H28A | 109.8 |
C16—C15—H15A | 108.2 | O5—C28—H28B | 109.8 |
C14—C15—H15B | 108.2 | C29—C28—H28B | 109.8 |
C16—C15—H15B | 108.2 | H28A—C28—H28B | 108.2 |
H15A—C15—H15B | 107.3 | C28—C29—Br3 | 112.5 (5) |
C17—C16—C21 | 117.9 (4) | C28—C29—H29A | 109.1 |
C17—C16—C15 | 117.9 (4) | Br3—C29—H29A | 109.1 |
C21—C16—C15 | 124.1 (4) | C28—C29—H29B | 109.1 |
C18—C17—C16 | 122.6 (4) | Br3—C29—H29B | 109.1 |
C18—C17—H17 | 118.7 | H29A—C29—H29B | 107.8 |
C16—C17—H17 | 118.7 | O6—C30—H30A | 109.5 |
C17—C18—O5 | 118.7 (4) | O6—C30—H30B | 109.5 |
C17—C18—C19 | 119.6 (4) | H30A—C30—H30B | 109.5 |
O5—C18—C19 | 121.7 (4) | O6—C30—H30C | 109.5 |
O6—C19—C20 | 125.4 (4) | H30A—C30—H30C | 109.5 |
O6—C19—C18 | 115.9 (4) | H30B—C30—H30C | 109.5 |
C21—C1—C2—C3 | 78.3 (5) | C10—C9—C14—C13 | −2.2 (6) |
C21—C1—C2—C7 | −99.4 (5) | C8—C9—C14—C13 | 174.6 (4) |
C7—C2—C3—C4 | −0.6 (7) | C10—C9—C14—C15 | 175.8 (4) |
C1—C2—C3—C4 | −178.5 (4) | C8—C9—C14—C15 | −7.4 (6) |
C2—C3—C4—O1 | −179.6 (4) | C12—C13—C14—C9 | 0.4 (6) |
C2—C3—C4—C5 | −0.4 (7) | C12—C13—C14—C15 | −177.7 (4) |
C22—O1—C4—C3 | −1.0 (7) | C9—C14—C15—C16 | 99.3 (5) |
C22—O1—C4—C5 | 179.8 (4) | C13—C14—C15—C16 | −82.8 (5) |
C24—O2—C5—C6 | 6.0 (7) | C14—C15—C16—C17 | 91.3 (5) |
C24—O2—C5—C4 | −175.1 (5) | C14—C15—C16—C21 | −92.3 (5) |
C3—C4—C5—C6 | 0.6 (7) | C21—C16—C17—C18 | 1.0 (7) |
O1—C4—C5—C6 | 179.8 (4) | C15—C16—C17—C18 | 177.7 (4) |
C3—C4—C5—O2 | −178.4 (4) | C16—C17—C18—O5 | −177.7 (4) |
O1—C4—C5—O2 | 0.9 (6) | C16—C17—C18—C19 | 1.9 (7) |
O2—C5—C6—C7 | 179.2 (4) | C28—O5—C18—C17 | 114.5 (5) |
C4—C5—C6—C7 | 0.3 (7) | C28—O5—C18—C19 | −65.1 (6) |
C5—C6—C7—C2 | −1.4 (6) | C30—O6—C19—C20 | 0.0 (8) |
C5—C6—C7—C8 | 175.6 (4) | C30—O6—C19—C18 | 178.4 (5) |
C3—C2—C7—C6 | 1.5 (6) | C17—C18—C19—O6 | 177.8 (4) |
C1—C2—C7—C6 | 179.2 (4) | O5—C18—C19—O6 | −2.6 (7) |
C3—C2—C7—C8 | −175.3 (4) | C17—C18—C19—C20 | −3.8 (7) |
C1—C2—C7—C8 | 2.4 (6) | O5—C18—C19—C20 | 175.9 (4) |
C6—C7—C8—C9 | −79.3 (5) | O6—C19—C20—C21 | −178.9 (5) |
C2—C7—C8—C9 | 97.5 (5) | C18—C19—C20—C21 | 2.8 (7) |
C7—C8—C9—C10 | 86.7 (5) | C17—C16—C21—C20 | −2.0 (6) |
C7—C8—C9—C14 | −90.2 (5) | C15—C16—C21—C20 | −178.4 (4) |
C14—C9—C10—C11 | 2.6 (7) | C17—C16—C21—C1 | 177.8 (4) |
C8—C9—C10—C11 | −174.4 (4) | C15—C16—C21—C1 | 1.3 (7) |
C9—C10—C11—O3 | 179.8 (5) | C19—C20—C21—C16 | 0.1 (7) |
C9—C10—C11—C12 | −1.1 (7) | C19—C20—C21—C1 | −179.7 (4) |
C25—O3—C11—C10 | −21.8 (8) | C2—C1—C21—C16 | 90.2 (5) |
C25'—O3—C11—C10 | 4.4 (11) | C2—C1—C21—C20 | −90.1 (5) |
C25—O3—C11—C12 | 159.0 (5) | C4—O1—C22—C23 | 164.7 (4) |
C25'—O3—C11—C12 | −174.8 (9) | O1—C22—C23—Br1 | 179.6 (3) |
C27—O4—C12—C13 | 3.3 (7) | C11—O3—C25—C26 | 90.3 (7) |
C27—O4—C12—C11 | −177.6 (4) | C25'—O3—C25—C26 | 17.7 (13) |
C10—C11—C12—O4 | −179.9 (4) | O3—C25—C26—Br2 | 67.6 (7) |
O3—C11—C12—O4 | −0.8 (6) | C11—O3—C25'—C26' | 160.3 (11) |
C10—C11—C12—C13 | −0.8 (7) | C25—O3—C25'—C26' | −81.5 (19) |
O3—C11—C12—C13 | 178.4 (4) | O3—C25'—C26'—Br2' | −77.9 (17) |
O4—C12—C13—C14 | −179.8 (4) | C18—O5—C28—C29 | −151.0 (5) |
C11—C12—C13—C14 | 1.1 (6) | O5—C28—C29—Br3 | −68.5 (6) |