Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046575/ci2212sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046575/ci2212Isup2.hkl |
CCDC reference: 629527
Data collection: SMART (Bruker, 1998); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
C22H24Br2O2 | F(000) = 968 |
Mr = 480.23 | Dx = 1.631 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2810 reflections |
a = 9.778 (2) Å | θ = 2.1–22.1° |
b = 11.787 (2) Å | µ = 4.16 mm−1 |
c = 16.972 (3) Å | T = 295 K |
V = 1956.1 (6) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.20 × 0.12 mm |
Bruker SMART 1K area-detector diffractometer | 3842 independent reflections |
Radiation source: fine-focus sealed tube | 2505 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
φ and ω scans | θmax = 26.2°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→12 |
Tmin = 0.422, Tmax = 0.635 | k = −11→14 |
10324 measured reflections | l = −21→18 |
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)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.187 | w = 1/[σ2(Fo2) + (0.1069P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3842 reflections | Δρmax = 1.53 e Å−3 |
247 parameters | Δρmin = −0.79 e Å−3 |
44 restraints | Absolute structure: Flack (1983), 1368 Fridel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.65396 (10) | 0.34294 (9) | 0.92585 (6) | 0.0542 (3) | |
Br2 | 0.93206 (12) | −0.09272 (11) | 0.58792 (6) | 0.0652 (4) | |
O1 | 0.8123 (6) | 0.1518 (6) | 0.8544 (4) | 0.0455 (16) | |
O2 | 0.7445 (6) | 0.0599 (6) | 0.6812 (4) | 0.0491 (17) | |
C1 | 0.6275 (6) | 0.0259 (6) | 0.8284 (5) | 0.034 (2) | |
C2 | 0.6763 (7) | 0.1285 (6) | 0.8567 (5) | 0.032 (2) | |
C3 | 0.5870 (7) | 0.2081 (7) | 0.8872 (5) | 0.041 (2) | |
C4 | 0.4480 (7) | 0.1857 (6) | 0.8876 (5) | 0.046 (2) | |
H4 | 0.3872 | 0.2395 | 0.9072 | 0.055* | |
C5 | 0.3993 (6) | 0.0832 (6) | 0.8589 (5) | 0.038 (2) | |
C6 | 0.4879 (5) | 0.0027 (6) | 0.8294 (5) | 0.037 (2) | |
C7 | 0.4357 (7) | −0.1060 (6) | 0.7963 (6) | 0.052 (3) | |
H7A | 0.4558 | −0.1671 | 0.8327 | 0.062* | 0.50 |
H7B | 0.4826 | −0.1220 | 0.7472 | 0.062* | 0.50 |
H7C | 0.4923 | −0.1679 | 0.8150 | 0.062* | 0.50 |
H7D | 0.4427 | −0.1037 | 0.7393 | 0.062* | 0.50 |
C8 | 0.2850 (8) | −0.1021 (14) | 0.7816 (9) | 0.074 (7) | 0.50 |
H8A | 0.2517 | −0.1779 | 0.7705 | 0.089* | 0.50 |
H8B | 0.2665 | −0.0549 | 0.7360 | 0.089* | 0.50 |
C9 | 0.2115 (11) | −0.0552 (8) | 0.8517 (10) | 0.062 (6) | 0.50 |
H9A | 0.2369 | −0.0975 | 0.8985 | 0.075* | 0.50 |
H9B | 0.1136 | −0.0627 | 0.8443 | 0.075* | 0.50 |
C8' | 0.2904 (9) | −0.1281 (8) | 0.8189 (11) | 0.074 (7) | 0.50 |
H8'A | 0.2861 | −0.1501 | 0.8739 | 0.089* | 0.50 |
H8'B | 0.2546 | −0.1901 | 0.7875 | 0.089* | 0.50 |
C9' | 0.2051 (10) | −0.0243 (11) | 0.8060 (10) | 0.062 (6) | 0.50 |
H9'A | 0.1094 | −0.0424 | 0.8141 | 0.075* | 0.50 |
H9'B | 0.2162 | 0.0021 | 0.7522 | 0.075* | 0.50 |
C10 | 0.2478 (6) | 0.0672 (7) | 0.8622 (6) | 0.061 (3) | |
H10A | 0.2049 | 0.1119 | 0.8211 | 0.073* | 0.50 |
H10B | 0.2136 | 0.0938 | 0.9126 | 0.073* | 0.50 |
H10C | 0.2025 | 0.1377 | 0.8485 | 0.073* | 0.50 |
H10D | 0.2208 | 0.0467 | 0.9153 | 0.073* | 0.50 |
C11 | 0.7282 (8) | −0.0540 (6) | 0.7962 (4) | 0.035 (2) | |
C12 | 0.7765 (8) | −0.0370 (7) | 0.7205 (4) | 0.037 (2) | |
C13 | 0.8736 (8) | −0.1099 (7) | 0.6892 (5) | 0.049 (3) | |
C14 | 0.9188 (9) | −0.1999 (8) | 0.7343 (4) | 0.050 (3) | |
H14 | 0.9820 | −0.2504 | 0.7130 | 0.060* | |
C15 | 0.8723 (8) | −0.2166 (7) | 0.8103 (4) | 0.049 (3) | |
C16 | 0.7714 (8) | −0.1460 (7) | 0.8402 (4) | 0.048 (2) | |
C17 | 0.7134 (9) | −0.1640 (8) | 0.9207 (4) | 0.060 (3) | |
H17A | 0.6153 | −0.1516 | 0.9195 | 0.072* | 0.50 |
H17B | 0.7532 | −0.1098 | 0.9570 | 0.072* | 0.50 |
H17C | 0.6238 | −0.1988 | 0.9163 | 0.072* | 0.50 |
H17D | 0.7024 | −0.0913 | 0.9467 | 0.072* | 0.50 |
C18 | 0.7424 (18) | −0.2823 (12) | 0.9488 (10) | 0.096 (12) | 0.50 |
H18A | 0.6913 | −0.3365 | 0.9175 | 0.116* | 0.50 |
H18B | 0.7146 | −0.2903 | 1.0034 | 0.116* | 0.50 |
C19 | 0.8932 (19) | −0.3051 (18) | 0.9411 (5) | 0.092 (10) | 0.50 |
H19A | 0.9448 | −0.2437 | 0.9648 | 0.110* | 0.50 |
H19B | 0.9165 | −0.3749 | 0.9682 | 0.110* | 0.50 |
C18' | 0.804 (2) | −0.2384 (17) | 0.9694 (5) | 0.096 (12) | 0.50 |
H18C | 0.7577 | −0.2588 | 1.0179 | 0.116* | 0.50 |
H18D | 0.8869 | −0.1974 | 0.9831 | 0.116* | 0.50 |
C19' | 0.841 (2) | −0.3436 (12) | 0.9248 (10) | 0.092 (10) | 0.50 |
H19C | 0.7579 | −0.3811 | 0.9070 | 0.110* | 0.50 |
H19D | 0.8895 | −0.3955 | 0.9591 | 0.110* | 0.50 |
C20 | 0.9281 (10) | −0.3148 (8) | 0.8553 (5) | 0.062 (3) | |
H20A | 1.0267 | −0.3175 | 0.8491 | 0.075* | 0.50 |
H20B | 0.8905 | −0.3847 | 0.8343 | 0.075* | 0.50 |
H20C | 1.0198 | −0.2969 | 0.8732 | 0.075* | 0.50 |
H20D | 0.9340 | −0.3802 | 0.8207 | 0.075* | 0.50 |
C21 | 0.8865 (9) | 0.1211 (9) | 0.9202 (6) | 0.057 (3) | |
H21A | 0.9809 | 0.1409 | 0.9126 | 0.086* | |
H21B | 0.8789 | 0.0407 | 0.9282 | 0.086* | |
H21C | 0.8514 | 0.1602 | 0.9655 | 0.086* | |
C22 | 0.6226 (11) | 0.0525 (13) | 0.6377 (7) | 0.073 (4) | |
H22A | 0.6057 | 0.1234 | 0.6117 | 0.109* | |
H22B | 0.5480 | 0.0356 | 0.6725 | 0.109* | |
H22C | 0.6308 | −0.0067 | 0.5991 | 0.109* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0595 (6) | 0.0390 (5) | 0.0640 (7) | 0.0000 (5) | −0.0017 (5) | −0.0128 (5) |
Br2 | 0.0687 (7) | 0.0663 (8) | 0.0606 (7) | −0.0039 (6) | 0.0239 (5) | −0.0167 (6) |
O1 | 0.034 (3) | 0.055 (4) | 0.047 (4) | 0.002 (3) | −0.001 (3) | −0.005 (4) |
O2 | 0.049 (4) | 0.045 (4) | 0.053 (4) | −0.002 (3) | 0.006 (3) | 0.000 (3) |
C1 | 0.030 (4) | 0.025 (5) | 0.046 (5) | 0.012 (3) | 0.004 (4) | 0.001 (4) |
C2 | 0.027 (4) | 0.038 (6) | 0.031 (4) | −0.003 (3) | 0.007 (3) | 0.000 (4) |
C3 | 0.050 (6) | 0.049 (6) | 0.023 (4) | −0.003 (5) | 0.002 (4) | −0.006 (4) |
C4 | 0.037 (5) | 0.045 (7) | 0.054 (6) | 0.019 (4) | 0.003 (4) | −0.006 (4) |
C5 | 0.032 (5) | 0.032 (6) | 0.050 (5) | 0.001 (4) | −0.002 (4) | −0.007 (5) |
C6 | 0.035 (5) | 0.040 (6) | 0.035 (5) | 0.000 (4) | −0.002 (4) | −0.009 (4) |
C7 | 0.050 (6) | 0.037 (6) | 0.068 (7) | 0.000 (5) | 0.008 (5) | −0.015 (5) |
C8 | 0.059 (8) | 0.114 (18) | 0.049 (16) | −0.050 (10) | 0.026 (9) | −0.022 (13) |
C9 | 0.039 (7) | 0.030 (10) | 0.12 (2) | −0.002 (6) | −0.013 (10) | 0.010 (10) |
C8' | 0.059 (8) | 0.114 (18) | 0.049 (16) | −0.050 (10) | 0.026 (9) | −0.022 (13) |
C9' | 0.039 (7) | 0.030 (10) | 0.12 (2) | −0.002 (6) | −0.013 (10) | 0.010 (10) |
C10 | 0.047 (6) | 0.079 (10) | 0.056 (6) | 0.013 (6) | 0.001 (5) | −0.001 (6) |
C11 | 0.037 (5) | 0.029 (5) | 0.040 (5) | 0.012 (4) | −0.001 (4) | −0.011 (4) |
C12 | 0.041 (5) | 0.022 (5) | 0.049 (6) | 0.002 (4) | 0.001 (4) | −0.004 (4) |
C13 | 0.046 (6) | 0.045 (7) | 0.055 (6) | −0.004 (4) | −0.010 (4) | −0.014 (5) |
C14 | 0.031 (5) | 0.066 (8) | 0.055 (6) | 0.003 (5) | 0.004 (4) | −0.025 (5) |
C15 | 0.053 (6) | 0.033 (6) | 0.061 (7) | 0.012 (4) | −0.009 (5) | −0.017 (5) |
C16 | 0.040 (5) | 0.054 (7) | 0.050 (6) | 0.010 (5) | −0.002 (4) | −0.013 (5) |
C17 | 0.060 (6) | 0.063 (7) | 0.056 (7) | 0.011 (5) | 0.002 (5) | 0.004 (6) |
C18 | 0.16 (3) | 0.074 (18) | 0.053 (11) | 0.08 (2) | 0.014 (14) | 0.008 (12) |
C19 | 0.10 (2) | 0.076 (18) | 0.099 (15) | 0.023 (16) | −0.006 (14) | 0.032 (13) |
C18' | 0.16 (3) | 0.074 (18) | 0.053 (11) | 0.08 (2) | 0.014 (14) | 0.008 (12) |
C19' | 0.10 (2) | 0.076 (18) | 0.099 (15) | 0.023 (16) | −0.006 (14) | 0.032 (13) |
C20 | 0.072 (7) | 0.048 (8) | 0.067 (7) | 0.028 (6) | −0.004 (6) | −0.005 (5) |
C21 | 0.044 (5) | 0.055 (8) | 0.072 (7) | −0.004 (4) | −0.005 (5) | −0.003 (6) |
C22 | 0.054 (7) | 0.084 (11) | 0.079 (8) | 0.005 (6) | −0.008 (6) | 0.014 (7) |
Br1—C3 | 1.840 (8) | C11—C16 | 1.383 (5) |
Br2—C13 | 1.822 (9) | C11—C12 | 1.385 (5) |
O1—C2 | 1.358 (9) | C12—C13 | 1.386 (5) |
O1—C21 | 1.380 (11) | C13—C14 | 1.381 (5) |
O2—C12 | 1.358 (10) | C14—C15 | 1.383 (5) |
O2—C22 | 1.406 (12) | C14—H14 | 0.93 |
C1—C2 | 1.386 (5) | C15—C16 | 1.387 (5) |
C1—C6 | 1.392 (5) | C15—C20 | 1.490 (5) |
C1—C11 | 1.467 (9) | C16—C17 | 1.494 (5) |
C2—C3 | 1.383 (5) | C17—C18' | 1.496 (5) |
C3—C4 | 1.384 (5) | C17—C18 | 1.500 (5) |
C4—C5 | 1.388 (5) | C17—H17A | 0.97 |
C4—H4 | 0.93 | C17—H17B | 0.97 |
C5—C6 | 1.379 (5) | C17—H17C | 0.97 |
C5—C10 | 1.494 (5) | C17—H17D | 0.97 |
C6—C7 | 1.490 (5) | C18—C19 | 1.504 (5) |
C7—C8' | 1.494 (5) | C18—H18A | 0.97 |
C7—C8 | 1.495 (5) | C18—H18B | 0.97 |
C7—H7A | 0.97 | C19—C20 | 1.501 (5) |
C7—H7B | 0.97 | C19—H19A | 0.97 |
C7—H7C | 0.97 | C19—H19B | 0.97 |
C7—H7D | 0.97 | C18'—C19' | 1.497 (5) |
C8—C9 | 1.495 (5) | C18'—H18C | 0.97 |
C8—H8A | 0.97 | C18'—H18D | 0.97 |
C8—H8B | 0.97 | C19'—C20 | 1.496 (5) |
C9—C10 | 1.497 (5) | C19'—H19C | 0.97 |
C9—H9A | 0.97 | C19'—H19D | 0.97 |
C9—H9B | 0.97 | C20—H20A | 0.97 |
C8'—C9' | 1.497 (5) | C20—H20B | 0.97 |
C8'—H8'A | 0.97 | C20—H20C | 0.97 |
C8'—H8'B | 0.97 | C20—H20D | 0.97 |
C9'—C10 | 1.499 (5) | C21—H21A | 0.96 |
C9'—H9'A | 0.97 | C21—H21B | 0.96 |
C9'—H9'B | 0.97 | C21—H21C | 0.96 |
C10—H10A | 0.97 | C22—H22A | 0.96 |
C10—H10B | 0.97 | C22—H22B | 0.96 |
C10—H10C | 0.97 | C22—H22C | 0.96 |
C10—H10D | 0.97 | ||
C2—O1—C21 | 116.0 (7) | C11—C12—C13 | 120.0 (7) |
C12—O2—C22 | 113.6 (8) | C14—C13—C12 | 118.9 (8) |
C2—C1—C6 | 120.3 (6) | C14—C13—Br2 | 120.5 (5) |
C2—C1—C11 | 117.2 (6) | C12—C13—Br2 | 120.5 (6) |
C6—C1—C11 | 122.5 (6) | C13—C14—C15 | 121.4 (8) |
O1—C2—C3 | 119.5 (6) | C13—C14—H14 | 119.3 |
O1—C2—C1 | 120.3 (6) | C15—C14—H14 | 119.3 |
C3—C2—C1 | 120.3 (7) | C14—C15—C16 | 119.4 (6) |
C2—C3—C4 | 119.5 (7) | C14—C15—C20 | 117.9 (6) |
C2—C3—Br1 | 119.6 (5) | C16—C15—C20 | 122.7 (5) |
C4—C3—Br1 | 120.8 (5) | C11—C16—C15 | 119.4 (6) |
C3—C4—C5 | 120.1 (7) | C11—C16—C17 | 119.3 (6) |
C3—C4—H4 | 120.0 | C15—C16—C17 | 121.3 (5) |
C5—C4—H4 | 120.0 | C16—C17—C18' | 111.3 (6) |
C6—C5—C4 | 120.7 (6) | C16—C17—C18 | 110.5 (6) |
C6—C5—C10 | 123.4 (5) | C16—C17—H17A | 109.5 |
C4—C5—C10 | 115.9 (6) | C18—C17—H17A | 109.5 |
C5—C6—C1 | 119.1 (5) | C16—C17—H17B | 109.5 |
C5—C6—C7 | 120.8 (5) | C18—C17—H17B | 109.5 |
C1—C6—C7 | 120.0 (6) | H17A—C17—H17B | 108.1 |
C6—C7—C8' | 112.3 (5) | C16—C17—H17C | 109.4 |
C6—C7—C8 | 112.0 (6) | C18'—C17—H17C | 109.4 |
C6—C7—H7A | 109.2 | C16—C17—H17D | 109.4 |
C8—C7—H7A | 109.2 | C18'—C17—H17D | 109.4 |
C6—C7—H7B | 109.2 | H17C—C17—H17D | 108.0 |
C8'—C7—H7B | 129.5 | C17—C18—C19 | 108.9 (7) |
C8—C7—H7B | 109.2 | C17—C18—H18A | 109.9 |
H7A—C7—H7B | 107.9 | C19—C18—H18A | 109.9 |
C6—C7—H7C | 109.1 | C17—C18—H18B | 109.9 |
C8'—C7—H7C | 109.1 | C19—C18—H18B | 109.9 |
C8—C7—H7C | 129.9 | H18A—C18—H18B | 108.3 |
C6—C7—H7D | 109.1 | C20—C19—C18 | 108.7 (7) |
C8'—C7—H7D | 109.1 | C20—C19—H19A | 109.9 |
H7C—C7—H7D | 107.9 | C18—C19—H19A | 109.9 |
C7—C8—C9 | 110.6 (7) | C20—C19—H19B | 109.9 |
C7—C8—H8A | 109.5 | C18—C19—H19B | 109.9 |
C9—C8—H8A | 109.5 | H19A—C19—H19B | 108.3 |
C7—C8—H8B | 109.5 | C17—C18'—C19' | 110.3 (7) |
C9—C8—H8B | 109.5 | C17—C18'—H18C | 109.6 |
H8A—C8—H8B | 108.1 | C19'—C18'—H18C | 109.6 |
C8—C9—C10 | 109.7 (7) | C17—C18'—H18D | 109.6 |
C8—C9—H9A | 109.7 | C19'—C18'—H18D | 109.6 |
C10—C9—H9A | 109.7 | H18C—C18'—H18D | 108.1 |
C8—C9—H9B | 109.7 | C18'—C19'—C20 | 110.3 (7) |
C10—C9—H9B | 109.7 | C18'—C19'—H19C | 109.6 |
H9A—C9—H9B | 108.2 | C20—C19'—H19C | 109.6 |
C7—C8'—C9' | 110.5 (7) | C18'—C19'—H19D | 109.6 |
C7—C8'—H8'A | 109.6 | C20—C19'—H19D | 109.6 |
C9'—C8'—H8'A | 109.6 | H19C—C19'—H19D | 108.1 |
C7—C8'—H8'B | 109.6 | C15—C20—C19' | 111.7 (6) |
C9'—C8'—H8'B | 109.6 | C15—C20—C19 | 110.7 (6) |
H8'A—C8'—H8'B | 108.1 | C15—C20—H20A | 109.5 |
C8'—C9'—C10 | 109.9 (7) | C19'—C20—H20A | 130.2 |
C8'—C9'—H9'A | 109.7 | C19—C20—H20A | 109.5 |
C10—C9'—H9'A | 109.7 | C15—C20—H20B | 109.5 |
C8'—C9'—H9'B | 109.7 | C19—C20—H20B | 109.5 |
C10—C9'—H9'B | 109.7 | H20A—C20—H20B | 108.1 |
H9'A—C9'—H9'B | 108.2 | C15—C20—H20C | 109.3 |
C5—C10—C9 | 110.6 (6) | C19'—C20—H20C | 109.3 |
C5—C10—C9' | 110.0 (6) | C15—C20—H20D | 109.3 |
C5—C10—H10A | 109.5 | C19'—C20—H20D | 109.3 |
C9—C10—H10A | 109.5 | H20C—C20—H20D | 107.9 |
C5—C10—H10B | 109.5 | O1—C21—H21A | 109.5 |
C9—C10—H10B | 109.5 | O1—C21—H21B | 109.5 |
H10A—C10—H10B | 108.1 | H21A—C21—H21B | 109.5 |
C5—C10—H10C | 109.7 | O1—C21—H21C | 109.5 |
C9'—C10—H10C | 109.7 | H21A—C21—H21C | 109.5 |
C5—C10—H10D | 109.7 | H21B—C21—H21C | 109.5 |
C9'—C10—H10D | 109.7 | O2—C22—H22A | 109.5 |
H10C—C10—H10D | 108.2 | O2—C22—H22B | 109.5 |
C16—C11—C12 | 120.7 (6) | H22A—C22—H22B | 109.5 |
C16—C11—C1 | 120.5 (6) | O2—C22—H22C | 109.5 |
C12—C11—C1 | 118.8 (6) | H22A—C22—H22C | 109.5 |
O2—C12—C11 | 119.9 (6) | H22B—C22—H22C | 109.5 |
O2—C12—C13 | 119.4 (7) | ||
C21—O1—C2—C3 | 89.4 (10) | C2—C1—C11—C12 | −79.5 (10) |
C21—O1—C2—C1 | −90.9 (10) | C6—C1—C11—C12 | 99.1 (10) |
C6—C1—C2—O1 | −178.9 (8) | C22—O2—C12—C11 | −89.3 (10) |
C11—C1—C2—O1 | −0.2 (12) | C22—O2—C12—C13 | 100.4 (10) |
C6—C1—C2—C3 | 0.9 (13) | C16—C11—C12—O2 | −173.0 (8) |
C11—C1—C2—C3 | 179.5 (7) | C1—C11—C12—O2 | 8.5 (12) |
O1—C2—C3—C4 | 178.2 (8) | C16—C11—C12—C13 | −2.8 (13) |
C1—C2—C3—C4 | −1.5 (13) | C1—C11—C12—C13 | 178.8 (8) |
O1—C2—C3—Br1 | −1.1 (11) | O2—C12—C13—C14 | 171.3 (8) |
C1—C2—C3—Br1 | 179.2 (6) | C11—C12—C13—C14 | 1.1 (13) |
C2—C3—C4—C5 | 1.2 (14) | O2—C12—C13—Br2 | −12.7 (12) |
Br1—C3—C4—C5 | −179.4 (7) | C11—C12—C13—Br2 | 177.0 (7) |
C3—C4—C5—C6 | −0.3 (14) | C12—C13—C14—C15 | −1.9 (14) |
C3—C4—C5—C10 | 179.8 (9) | Br2—C13—C14—C15 | −177.8 (7) |
C4—C5—C6—C1 | −0.4 (14) | C13—C14—C15—C16 | 4.3 (14) |
C10—C5—C6—C1 | 179.6 (9) | C13—C14—C15—C20 | −179.0 (9) |
C4—C5—C6—C7 | −178.1 (9) | C12—C11—C16—C15 | 5.2 (14) |
C10—C5—C6—C7 | 1.8 (15) | C1—C11—C16—C15 | −176.4 (8) |
C2—C1—C6—C5 | 0.1 (13) | C12—C11—C16—C17 | −177.8 (8) |
C11—C1—C6—C5 | −178.5 (8) | C1—C11—C16—C17 | 0.6 (13) |
C2—C1—C6—C7 | 177.9 (8) | C14—C15—C16—C11 | −5.9 (14) |
C11—C1—C6—C7 | −0.7 (13) | C20—C15—C16—C11 | 177.6 (9) |
C5—C6—C7—C8' | −15.5 (14) | C14—C15—C16—C17 | 177.2 (9) |
C1—C6—C7—C8' | 166.8 (11) | C20—C15—C16—C17 | 0.7 (15) |
C5—C6—C7—C8 | 14.0 (13) | C11—C16—C17—C18' | −159.5 (13) |
C1—C6—C7—C8 | −163.7 (11) | C15—C16—C17—C18' | 17.4 (16) |
C6—C7—C8—C9 | −47.6 (13) | C11—C16—C17—C18 | 164.4 (12) |
C8'—C7—C8—C9 | 48.7 (9) | C15—C16—C17—C18 | −18.7 (15) |
C7—C8—C9—C10 | 67.1 (13) | C16—C17—C18—C19 | 52.5 (14) |
C6—C7—C8'—C9' | 47.1 (14) | C18'—C17—C18—C19 | −45.4 (10) |
C8—C7—C8'—C9' | −47.9 (10) | C17—C18—C19—C20 | −70.6 (13) |
C7—C8'—C9'—C10 | −66.9 (13) | C16—C17—C18'—C19' | −50.0 (15) |
C6—C5—C10—C9 | 16.1 (14) | C18—C17—C18'—C19' | 45.4 (9) |
C4—C5—C10—C9 | −164.0 (10) | C17—C18'—C19'—C20 | 66.6 (14) |
C6—C5—C10—C9' | −19.5 (14) | C14—C15—C20—C19' | −162.6 (13) |
C4—C5—C10—C9' | 160.4 (11) | C16—C15—C20—C19' | 14.0 (17) |
C8—C9—C10—C5 | −49.0 (13) | C14—C15—C20—C19 | 166.8 (13) |
C8—C9—C10—C9' | 46.4 (8) | C16—C15—C20—C19 | −16.7 (16) |
C8'—C9'—C10—C5 | 50.6 (13) | C18'—C19'—C20—C15 | −46.4 (15) |
C8'—C9'—C10—C9 | −46.7 (8) | C18'—C19'—C20—C19 | 47.3 (10) |
C2—C1—C11—C16 | 102.0 (10) | C18—C19—C20—C15 | 50.2 (14) |
C6—C1—C11—C16 | −79.4 (12) | C18—C19—C20—C19' | −47.5 (10) |