Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017357/ci2332sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017357/ci2332Isup2.hkl |
CCDC reference: 647155
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek,2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
C15H8Br2Cl3FO | F(000) = 1888 |
Mr = 489.38 | Dx = 1.910 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2547 reflections |
a = 10.5292 (10) Å | θ = 4–27° |
b = 10.5897 (10) Å | µ = 5.24 mm−1 |
c = 30.534 (3) Å | T = 293 K |
β = 91.111 (2)° | Block, colourless |
V = 3403.9 (6) Å3 | 0.23 × 0.22 × 0.21 mm |
Z = 8 |
Bruker SMART APEX CCD area-detector diffractometer | 4658 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 28.0°, θmin = 1.9° |
ω scans | h = −13→13 |
38185 measured reflections | k = −13→13 |
8041 independent reflections | l = −39→40 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0649P)2 + 2.8825P] where P = (Fo2 + 2Fc2)/3 |
8041 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.82 e Å−3 |
4 restraints | Δρmin = −0.43 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 | ||
C1 | 0.1634 (5) | 0.1958 (4) | −0.07685 (14) | 0.0715 (13) | |
C2 | 0.2360 (4) | 0.1443 (4) | −0.04381 (15) | 0.0675 (11) | |
H2 | 0.3048 | 0.0927 | −0.0500 | 0.081* | |
C3 | 0.2050 (4) | 0.1704 (4) | −0.00099 (14) | 0.0647 (11) | |
H3 | 0.2540 | 0.1363 | 0.0218 | 0.078* | |
C4 | 0.1030 (4) | 0.2461 (4) | 0.00858 (13) | 0.0595 (10) | |
C5 | 0.0336 (4) | 0.2989 (5) | −0.02573 (16) | 0.0711 (12) | |
H5 | −0.0337 | 0.3528 | −0.0198 | 0.085* | |
C6 | 0.0628 (5) | 0.2727 (5) | −0.06870 (16) | 0.0797 (14) | |
H6 | 0.0147 | 0.3069 | −0.0916 | 0.096* | |
C7 | 0.0624 (4) | 0.2688 (4) | 0.05502 (14) | 0.0606 (10) | |
H7 | −0.0038 | 0.3339 | 0.0548 | 0.073* | |
C8 | 0.1643 (3) | 0.3063 (4) | 0.08694 (13) | 0.0544 (9) | |
H8 | 0.2270 | 0.2387 | 0.0908 | 0.065* | |
C9 | 0.1151 (4) | 0.3507 (4) | 0.13080 (13) | 0.0610 (10) | |
C10 | 0.2100 (4) | 0.3610 (4) | 0.16804 (13) | 0.0578 (10) | |
C11 | 0.2720 (4) | 0.2584 (4) | 0.18700 (13) | 0.0650 (11) | |
C12 | 0.3588 (4) | 0.2740 (5) | 0.22104 (14) | 0.0739 (13) | |
H12 | 0.4002 | 0.2044 | 0.2332 | 0.089* | |
C13 | 0.3835 (4) | 0.3933 (6) | 0.23680 (14) | 0.0748 (13) | |
C14 | 0.3234 (5) | 0.4952 (5) | 0.21762 (15) | 0.0745 (13) | |
C15 | 0.2365 (4) | 0.4798 (5) | 0.18444 (14) | 0.0705 (12) | |
H15 | 0.1948 | 0.5498 | 0.1727 | 0.085* | |
O1 | 0.0092 (3) | 0.3911 (3) | 0.13397 (10) | 0.0799 (10) | |
F1 | 0.3510 (3) | 0.6117 (3) | 0.23230 (10) | 0.1027 (9) | |
Cl1 | 0.2018 (2) | 0.15682 (16) | −0.13060 (4) | 0.1212 (6) | |
Cl2 | 0.23857 (14) | 0.10621 (12) | 0.16901 (4) | 0.0880 (4) | |
Cl3 | 0.48968 (15) | 0.41525 (18) | 0.27969 (5) | 0.1128 (5) | |
Br1 | −0.00960 (4) | 0.10932 (4) | 0.080122 (17) | 0.07036 (15) | |
Br2 | 0.24410 (4) | 0.46180 (4) | 0.062615 (13) | 0.05633 (13) | |
C16 | 0.6532 (5) | 0.2192 (4) | −0.08118 (14) | 0.0697 (12) | |
C17 | 0.7294 (5) | 0.1616 (4) | −0.04981 (15) | 0.0692 (12) | |
H17 | 0.7990 | 0.1132 | −0.0578 | 0.083* | |
C18 | 0.7000 (4) | 0.1776 (4) | −0.00648 (14) | 0.0638 (11) | |
H18 | 0.7508 | 0.1399 | 0.0151 | 0.077* | |
C19 | 0.5972 (4) | 0.2482 (4) | 0.00550 (13) | 0.0586 (10) | |
C20 | 0.5230 (4) | 0.3054 (4) | −0.02688 (15) | 0.0674 (11) | |
H20 | 0.4537 | 0.3543 | −0.0190 | 0.081* | |
C21 | 0.5504 (5) | 0.2908 (5) | −0.07012 (15) | 0.0735 (13) | |
H21 | 0.5000 | 0.3288 | −0.0917 | 0.088* | |
C22 | 0.5616 (4) | 0.2649 (4) | 0.05230 (14) | 0.0629 (10) | |
H22 | 0.4943 | 0.3287 | 0.0537 | 0.076* | |
C23 | 0.6665 (4) | 0.3016 (4) | 0.08345 (13) | 0.0562 (9) | |
H23 | 0.7306 | 0.2346 | 0.0853 | 0.067* | |
C24 | 0.6207 (4) | 0.3362 (5) | 0.12960 (14) | 0.0656 (11) | |
C25 | 0.7153 (4) | 0.3188 (4) | 0.16580 (12) | 0.0577 (10) | |
C26 | 0.7708 (4) | 0.2014 (4) | 0.17204 (13) | 0.0605 (10) | |
H26 | 0.7491 | 0.1346 | 0.1536 | 0.073* | |
C27 | 0.8583 (4) | 0.1840 (4) | 0.20570 (14) | 0.0659 (11) | |
C28 | 0.8918 (4) | 0.2801 (5) | 0.23322 (14) | 0.0712 (12) | |
C29 | 0.8381 (5) | 0.3962 (5) | 0.22766 (15) | 0.0771 (13) | |
H29 | 0.8603 | 0.4622 | 0.2464 | 0.093* | |
C30 | 0.7509 (5) | 0.4155 (4) | 0.19428 (14) | 0.0685 (12) | |
O2 | 0.5167 (3) | 0.3810 (4) | 0.13436 (11) | 0.0916 (11) | |
F2 | 0.9088 (3) | 0.0688 (3) | 0.21181 (9) | 0.0949 (9) | |
Cl4 | 0.6942 (2) | 0.20255 (16) | −0.13589 (4) | 0.1234 (6) | |
Cl5 | 0.68819 (19) | 0.56600 (14) | 0.18690 (5) | 0.1132 (5) | |
Cl6 | 1.00148 (15) | 0.25293 (17) | 0.27512 (5) | 0.1122 (5) | |
Br3 | 0.49677 (4) | 0.10307 (5) | 0.078207 (18) | 0.07911 (17) | |
Br4 | 0.74319 (4) | 0.46030 (4) | 0.062079 (13) | 0.05910 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.100 (4) | 0.059 (3) | 0.055 (3) | −0.028 (3) | −0.005 (2) | −0.001 (2) |
C2 | 0.075 (3) | 0.065 (3) | 0.063 (3) | −0.002 (2) | 0.005 (2) | −0.008 (2) |
C3 | 0.059 (2) | 0.075 (3) | 0.060 (3) | 0.012 (2) | −0.013 (2) | 0.000 (2) |
C4 | 0.052 (2) | 0.067 (3) | 0.059 (2) | 0.0036 (19) | −0.0113 (19) | 0.003 (2) |
C5 | 0.059 (2) | 0.075 (3) | 0.078 (3) | 0.002 (2) | −0.017 (2) | 0.013 (2) |
C6 | 0.092 (4) | 0.085 (3) | 0.062 (3) | −0.012 (3) | −0.025 (3) | 0.016 (3) |
C7 | 0.051 (2) | 0.058 (2) | 0.073 (3) | 0.0032 (16) | 0.0011 (19) | 0.0126 (18) |
C8 | 0.048 (2) | 0.0569 (19) | 0.059 (2) | 0.0024 (15) | 0.0020 (17) | 0.0139 (17) |
C9 | 0.053 (2) | 0.076 (3) | 0.055 (2) | 0.012 (2) | 0.0068 (19) | 0.007 (2) |
C10 | 0.050 (2) | 0.077 (3) | 0.047 (2) | 0.010 (2) | 0.0086 (17) | 0.008 (2) |
C11 | 0.063 (2) | 0.078 (3) | 0.055 (2) | 0.002 (2) | 0.007 (2) | 0.019 (2) |
C12 | 0.069 (3) | 0.096 (4) | 0.056 (3) | −0.004 (3) | −0.006 (2) | 0.031 (3) |
C13 | 0.065 (3) | 0.108 (4) | 0.051 (2) | −0.008 (3) | −0.002 (2) | 0.012 (3) |
C14 | 0.079 (3) | 0.086 (4) | 0.058 (3) | 0.001 (3) | 0.009 (2) | −0.009 (3) |
C15 | 0.072 (3) | 0.086 (3) | 0.054 (2) | 0.022 (3) | 0.008 (2) | 0.001 (2) |
O1 | 0.0494 (16) | 0.120 (3) | 0.070 (2) | 0.0228 (17) | 0.0094 (14) | −0.0030 (19) |
F1 | 0.118 (2) | 0.102 (2) | 0.088 (2) | 0.0098 (18) | −0.0042 (17) | −0.0267 (17) |
Cl1 | 0.2025 (19) | 0.1038 (11) | 0.0576 (8) | −0.0199 (12) | 0.0096 (9) | −0.0057 (7) |
Cl2 | 0.1054 (9) | 0.0758 (8) | 0.0823 (8) | −0.0079 (7) | −0.0174 (7) | 0.0231 (6) |
Cl3 | 0.1140 (11) | 0.1493 (14) | 0.0738 (9) | −0.0139 (10) | −0.0320 (8) | 0.0064 (9) |
Br1 | 0.0548 (2) | 0.0668 (3) | 0.0897 (3) | −0.0123 (2) | 0.0066 (2) | 0.0137 (2) |
Br2 | 0.0573 (2) | 0.0539 (2) | 0.0578 (2) | −0.00651 (17) | 0.00270 (18) | 0.00819 (18) |
C16 | 0.105 (4) | 0.055 (2) | 0.049 (2) | −0.024 (3) | −0.011 (2) | −0.003 (2) |
C17 | 0.081 (3) | 0.065 (3) | 0.062 (3) | −0.004 (2) | 0.003 (2) | −0.006 (2) |
C18 | 0.061 (2) | 0.074 (3) | 0.057 (3) | 0.010 (2) | −0.005 (2) | 0.007 (2) |
C19 | 0.050 (2) | 0.067 (3) | 0.058 (2) | 0.0040 (19) | −0.0081 (18) | 0.009 (2) |
C20 | 0.057 (2) | 0.075 (3) | 0.070 (3) | 0.003 (2) | −0.015 (2) | 0.016 (2) |
C21 | 0.085 (3) | 0.071 (3) | 0.064 (3) | −0.007 (3) | −0.026 (2) | 0.017 (2) |
C22 | 0.048 (2) | 0.067 (2) | 0.073 (3) | 0.0080 (17) | 0.0023 (19) | 0.018 (2) |
C23 | 0.052 (2) | 0.0621 (19) | 0.055 (2) | 0.0079 (16) | 0.0063 (18) | 0.0105 (18) |
C24 | 0.058 (2) | 0.082 (3) | 0.058 (3) | 0.019 (2) | 0.007 (2) | 0.000 (2) |
C25 | 0.055 (2) | 0.074 (3) | 0.045 (2) | 0.006 (2) | 0.0073 (18) | 0.001 (2) |
C26 | 0.066 (2) | 0.066 (3) | 0.049 (2) | −0.001 (2) | 0.0040 (19) | 0.000 (2) |
C27 | 0.069 (3) | 0.073 (3) | 0.056 (2) | 0.007 (2) | −0.002 (2) | 0.009 (2) |
C28 | 0.071 (3) | 0.093 (4) | 0.049 (2) | −0.009 (3) | −0.003 (2) | 0.007 (2) |
C29 | 0.093 (3) | 0.085 (4) | 0.053 (3) | −0.012 (3) | 0.005 (2) | −0.011 (2) |
C30 | 0.084 (3) | 0.066 (3) | 0.056 (3) | 0.007 (2) | 0.014 (2) | −0.001 (2) |
O2 | 0.0633 (19) | 0.135 (3) | 0.077 (2) | 0.040 (2) | 0.0156 (17) | −0.001 (2) |
F2 | 0.113 (2) | 0.089 (2) | 0.0818 (19) | 0.0223 (17) | −0.0241 (16) | 0.0088 (15) |
Cl4 | 0.214 (2) | 0.1040 (11) | 0.0519 (7) | −0.0169 (12) | 0.0009 (9) | −0.0098 (7) |
Cl5 | 0.1735 (16) | 0.0746 (9) | 0.0914 (10) | 0.0309 (9) | 0.0057 (10) | −0.0119 (7) |
Cl6 | 0.1157 (11) | 0.1452 (14) | 0.0743 (9) | −0.0153 (10) | −0.0353 (8) | 0.0094 (9) |
Br3 | 0.0585 (3) | 0.0802 (3) | 0.0989 (4) | −0.0106 (2) | 0.0081 (2) | 0.0238 (3) |
Br4 | 0.0569 (2) | 0.0604 (3) | 0.0600 (3) | −0.00088 (18) | 0.00068 (18) | 0.00712 (19) |
C1—C2 | 1.368 (6) | C16—C17 | 1.380 (6) |
C1—C6 | 1.362 (7) | C16—C21 | 1.369 (7) |
C1—Cl1 | 1.747 (5) | C16—Cl4 | 1.743 (5) |
C2—C3 | 1.382 (6) | C17—C18 | 1.375 (6) |
C2—H2 | 0.93 | C17—H17 | 0.93 |
C3—C4 | 1.376 (6) | C18—C19 | 1.371 (6) |
C3—H3 | 0.93 | C18—H18 | 0.93 |
C4—C5 | 1.384 (6) | C19—C20 | 1.387 (5) |
C4—C7 | 1.508 (6) | C19—C22 | 1.495 (6) |
C5—C6 | 1.382 (7) | C20—C21 | 1.366 (6) |
C5—H5 | 0.93 | C20—H20 | 0.93 |
C6—H6 | 0.93 | C21—H21 | 0.93 |
C7—C8 | 1.489 (6) | C22—C23 | 1.495 (6) |
C7—Br1 | 2.010 (4) | C22—Br3 | 2.013 (4) |
C7—H7 | 0.98 | C22—H22 | 0.98 |
C8—C9 | 1.520 (5) | C23—C24 | 1.543 (5) |
C8—Br2 | 1.998 (4) | C23—Br4 | 1.981 (4) |
C8—H8 | 0.98 | C23—H23 | 0.98 |
C9—O1 | 1.200 (5) | C24—O2 | 1.205 (5) |
C9—C10 | 1.503 (6) | C24—C25 | 1.485 (6) |
C10—C15 | 1.380 (6) | C25—C30 | 1.390 (6) |
C10—C11 | 1.388 (6) | C25—C26 | 1.385 (6) |
C11—C12 | 1.381 (6) | C26—C27 | 1.380 (6) |
C11—Cl2 | 1.737 (5) | C26—H26 | 0.93 |
C12—C13 | 1.376 (7) | C27—F2 | 1.342 (5) |
C12—H12 | 0.93 | C27—C28 | 1.362 (6) |
C13—C14 | 1.376 (7) | C28—C29 | 1.363 (7) |
C13—Cl3 | 1.721 (5) | C28—Cl6 | 1.731 (5) |
C14—F1 | 1.343 (6) | C29—C30 | 1.373 (6) |
C14—C15 | 1.361 (6) | C29—H29 | 0.93 |
C15—H15 | 0.93 | C30—Cl5 | 1.738 (5) |
C2—C1—C6 | 121.9 (4) | C17—C16—C21 | 121.7 (4) |
C2—C1—Cl1 | 117.5 (4) | C17—C16—Cl4 | 118.0 (4) |
C6—C1—Cl1 | 120.5 (4) | C21—C16—Cl4 | 120.3 (4) |
C1—C2—C3 | 118.7 (4) | C18—C17—C16 | 118.3 (4) |
C1—C2—H2 | 120.7 | C18—C17—H17 | 120.8 |
C3—C2—H2 | 120.7 | C16—C17—H17 | 120.8 |
C2—C3—C4 | 121.1 (4) | C17—C18—C19 | 121.2 (4) |
C2—C3—H3 | 119.4 | C17—C18—H18 | 119.4 |
C4—C3—H3 | 119.4 | C19—C18—H18 | 119.4 |
C3—C4—C5 | 118.6 (4) | C18—C19—C20 | 119.0 (4) |
C3—C4—C7 | 122.0 (4) | C18—C19—C22 | 122.3 (4) |
C5—C4—C7 | 119.4 (4) | C20—C19—C22 | 118.7 (4) |
C6—C5—C4 | 120.9 (5) | C21—C20—C19 | 120.8 (4) |
C6—C5—H5 | 119.6 | C21—C20—H20 | 119.6 |
C4—C5—H5 | 119.6 | C19—C20—H20 | 119.6 |
C1—C6—C5 | 118.8 (4) | C20—C21—C16 | 119.0 (4) |
C1—C6—H6 | 120.6 | C20—C21—H21 | 120.5 |
C5—C6—H6 | 120.6 | C16—C21—H21 | 120.5 |
C8—C7—C4 | 116.4 (3) | C19—C22—C23 | 116.3 (3) |
C8—C7—Br1 | 104.3 (3) | C19—C22—Br3 | 111.6 (3) |
C4—C7—Br1 | 109.9 (3) | C23—C22—Br3 | 102.9 (3) |
C8—C7—H7 | 108.7 | C19—C22—H22 | 108.6 |
C4—C7—H7 | 108.7 | C23—C22—H22 | 108.6 |
Br1—C7—H7 | 108.7 | Br3—C22—H22 | 108.6 |
C7—C8—C9 | 113.9 (3) | C22—C23—C24 | 113.7 (3) |
C7—C8—Br2 | 106.2 (3) | C22—C23—Br4 | 108.2 (3) |
C9—C8—Br2 | 103.1 (3) | C24—C23—Br4 | 103.7 (3) |
C7—C8—H8 | 111.1 | C22—C23—H23 | 110.4 |
C9—C8—H8 | 111.1 | C24—C23—H23 | 110.4 |
Br2—C8—H8 | 111.1 | Br4—C23—H23 | 110.4 |
O1—C9—C10 | 121.2 (4) | O2—C24—C25 | 123.9 (4) |
O1—C9—C8 | 121.0 (4) | O2—C24—C23 | 120.3 (4) |
C10—C9—C8 | 117.2 (3) | C25—C24—C23 | 115.7 (3) |
C15—C10—C11 | 118.1 (4) | C30—C25—C26 | 117.9 (4) |
C15—C10—C9 | 117.9 (4) | C30—C25—C24 | 122.9 (4) |
C11—C10—C9 | 124.0 (4) | C26—C25—C24 | 119.2 (4) |
C12—C11—C10 | 121.3 (4) | C27—C26—C25 | 119.7 (4) |
C12—C11—Cl2 | 118.4 (4) | C27—C26—H26 | 120.1 |
C10—C11—Cl2 | 120.3 (3) | C25—C26—H26 | 120.1 |
C11—C12—C13 | 119.4 (4) | F2—C27—C28 | 119.7 (4) |
C11—C12—H12 | 120.3 | F2—C27—C26 | 118.8 (4) |
C13—C12—H12 | 120.3 | C28—C27—C26 | 121.4 (4) |
C14—C13—C12 | 119.3 (4) | C29—C28—C27 | 119.7 (4) |
C14—C13—Cl3 | 120.3 (4) | C29—C28—Cl6 | 120.8 (4) |
C12—C13—Cl3 | 120.4 (4) | C27—C28—Cl6 | 119.5 (4) |
F1—C14—C15 | 119.8 (5) | C28—C29—C30 | 119.8 (4) |
F1—C14—C13 | 118.9 (4) | C28—C29—H29 | 120.1 |
C15—C14—C13 | 121.3 (5) | C30—C29—H29 | 120.1 |
C14—C15—C10 | 120.5 (5) | C29—C30—C25 | 121.5 (4) |
C14—C15—H15 | 119.7 | C29—C30—Cl5 | 118.6 (4) |
C10—C15—H15 | 119.7 | C25—C30—Cl5 | 119.8 (4) |
C6—C1—C2—C3 | 0.6 (7) | C21—C16—C17—C18 | −0.1 (7) |
Cl1—C1—C2—C3 | −177.9 (3) | Cl4—C16—C17—C18 | 178.0 (3) |
C1—C2—C3—C4 | 0.4 (7) | C16—C17—C18—C19 | 0.5 (7) |
C2—C3—C4—C5 | −1.8 (7) | C17—C18—C19—C20 | −0.8 (7) |
C2—C3—C4—C7 | 175.9 (4) | C17—C18—C19—C22 | 178.7 (4) |
C3—C4—C5—C6 | 2.4 (7) | C18—C19—C20—C21 | 0.8 (7) |
C7—C4—C5—C6 | −175.4 (4) | C22—C19—C20—C21 | −178.7 (4) |
C2—C1—C6—C5 | −0.1 (7) | C19—C20—C21—C16 | −0.5 (7) |
Cl1—C1—C6—C5 | 178.4 (4) | C17—C16—C21—C20 | 0.1 (7) |
C4—C5—C6—C1 | −1.5 (7) | Cl4—C16—C21—C20 | −177.9 (3) |
C3—C4—C7—C8 | 49.2 (6) | C18—C19—C22—C23 | 48.5 (6) |
C5—C4—C7—C8 | −133.0 (4) | C20—C19—C22—C23 | −132.0 (4) |
C3—C4—C7—Br1 | −68.9 (5) | C18—C19—C22—Br3 | −69.1 (5) |
C5—C4—C7—Br1 | 108.8 (4) | C20—C19—C22—Br3 | 110.4 (4) |
C4—C7—C8—C9 | 169.6 (3) | C19—C22—C23—C24 | 171.6 (4) |
Br1—C7—C8—C9 | −69.2 (4) | Br3—C22—C23—C24 | −66.1 (4) |
C4—C7—C8—Br2 | 56.8 (4) | C19—C22—C23—Br4 | 57.0 (4) |
Br1—C7—C8—Br2 | 178.0 (2) | Br3—C22—C23—Br4 | 179.3 (2) |
C7—C8—C9—O1 | −23.4 (6) | C22—C23—C24—O2 | −29.7 (6) |
Br2—C8—C9—O1 | 91.2 (4) | Br4—C23—C24—O2 | 87.5 (5) |
C7—C8—C9—C10 | 166.0 (4) | C22—C23—C24—C25 | 154.3 (4) |
Br2—C8—C9—C10 | −79.3 (4) | Br4—C23—C24—C25 | −88.4 (4) |
O1—C9—C10—C15 | −56.7 (6) | O2—C24—C25—C30 | −51.5 (7) |
C8—C9—C10—C15 | 113.8 (4) | C23—C24—C25—C30 | 124.3 (4) |
O1—C9—C10—C11 | 123.0 (5) | O2—C24—C25—C26 | 128.0 (5) |
C8—C9—C10—C11 | −66.4 (5) | C23—C24—C25—C26 | −56.2 (5) |
C15—C10—C11—C12 | −0.6 (6) | C30—C25—C26—C27 | −0.1 (6) |
C9—C10—C11—C12 | 179.7 (4) | C24—C25—C26—C27 | −179.7 (4) |
C15—C10—C11—Cl2 | 177.9 (3) | C25—C26—C27—F2 | 178.5 (4) |
C9—C10—C11—Cl2 | −1.9 (6) | C25—C26—C27—C28 | 0.1 (7) |
C10—C11—C12—C13 | 0.6 (7) | F2—C27—C28—C29 | −178.4 (4) |
Cl2—C11—C12—C13 | −177.8 (4) | C26—C27—C28—C29 | 0.1 (7) |
C11—C12—C13—C14 | −1.5 (7) | F2—C27—C28—Cl6 | 1.2 (6) |
C11—C12—C13—Cl3 | 179.1 (3) | C26—C27—C28—Cl6 | 179.7 (3) |
C12—C13—C14—F1 | −177.9 (4) | C27—C28—C29—C30 | −0.2 (7) |
Cl3—C13—C14—F1 | 1.4 (6) | Cl6—C28—C29—C30 | −179.8 (4) |
C12—C13—C14—C15 | 2.4 (7) | C28—C29—C30—C25 | 0.2 (7) |
Cl3—C13—C14—C15 | −178.2 (4) | C28—C29—C30—Cl5 | −177.8 (4) |
F1—C14—C15—C10 | 178.0 (4) | C26—C25—C30—C29 | −0.1 (6) |
C13—C14—C15—C10 | −2.4 (7) | C24—C25—C30—C29 | 179.5 (4) |
C11—C10—C15—C14 | 1.4 (6) | C26—C25—C30—Cl5 | 177.9 (3) |
C9—C10—C15—C14 | −178.8 (4) | C24—C25—C30—Cl5 | −2.5 (6) |