Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031771/om2045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031771/om2045Iasup2.hkl |
CCDC reference: 615588
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.
C22H15ClF6S2 | Dx = 1.537 Mg m−3 |
Mr = 492.91 | Melting point: 418 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.232 (3) Å | Cell parameters from 3265 reflections |
b = 9.0912 (13) Å | θ = 2.9–24.2° |
c = 11.1534 (17) Å | µ = 0.43 mm−1 |
β = 98.243 (2)° | T = 294 K |
V = 2130.6 (5) Å3 | Prism, colorless |
Z = 4 | 0.24 × 0.22 × 0.20 mm |
F(000) = 1000 |
Bruker SMART CCD area-detector diffractometer | 4337 independent reflections |
Radiation source: fine-focus sealed tube | 2721 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 26.4°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −26→26 |
Tmin = 0.903, Tmax = 0.918 | k = −5→11 |
11640 measured reflections | l = −13→13 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0534P)2 + 0.3854P] where P = (Fo2 + 2Fc2)/3 |
4337 reflections | (Δ/σ)max = 0.001 |
340 parameters | Δρmax = 0.21 e Å−3 |
24 restraints | Δρmin = −0.26 e Å−3 |
Experimental. 1H NMR (400 MHz, CDCl3): δ 1.86 (s, 3H, –CH3), 1.92 (s, 3H, –CH3), 2.42 (s, 3H, –CH3), 6.73 (s, 1H, thiophene-H), 7.23 (s, 1H, thiophene-H), 7.34–7.36 (d, 2H, J = 8.5?Hz, ben-H), 7.45–7.47 (d, 2H, J = 8.5 Hz, ben-H); 19 F NMR (400 MHz, CDCl3): δ 109.88 (2 F), 110.19 (2 F), 131.87 (2 F). 13 C NMR (400 MHz, CDCl3): δ 14.3, 14.5, 15.1, 122.9, 124.5, 126.2, 126.8, 129.2, 131.9, 133.7, 137.9, 139.8, 140.7, 141.5. |
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) | |
S1 | 0.06754 (3) | 0.29044 (8) | 0.52882 (6) | 0.0626 (2) | |
S2 | 0.35808 (3) | 0.31480 (7) | 0.55798 (6) | 0.0579 (2) | |
Cl1 | 0.59112 (3) | 0.38894 (10) | 0.16552 (8) | 0.0858 (3) | |
F1 | 0.1258 (5) | 0.8341 (7) | 0.6560 (11) | 0.076 (2) | 0.63 (2) |
F2 | 0.1049 (3) | 0.8307 (5) | 0.4626 (11) | 0.080 (2) | 0.63 (2) |
F1' | 0.1505 (8) | 0.8150 (13) | 0.7013 (11) | 0.068 (3) | 0.37 (2) |
F2' | 0.0939 (4) | 0.8226 (10) | 0.528 (2) | 0.076 (3) | 0.37 (2) |
F3 | 0.2343 (3) | 0.9495 (14) | 0.6609 (8) | 0.076 (2) | 0.64 (3) |
F4 | 0.1932 (5) | 1.0241 (6) | 0.4837 (13) | 0.082 (3) | 0.64 (3) |
F3' | 0.2138 (12) | 1.012 (2) | 0.609 (3) | 0.101 (7) | 0.36 (3) |
F4' | 0.1738 (7) | 0.963 (3) | 0.4276 (18) | 0.098 (6) | 0.36 (3) |
F5 | 0.3154 (2) | 0.8412 (5) | 0.5422 (10) | 0.0649 (18) | 0.69 (3) |
F6 | 0.2516 (4) | 0.8257 (9) | 0.3761 (6) | 0.0657 (15) | 0.69 (3) |
F5' | 0.3047 (14) | 0.8355 (12) | 0.609 (5) | 0.116 (11) | 0.31 (3) |
F6' | 0.2768 (19) | 0.842 (2) | 0.418 (4) | 0.106 (10) | 0.31 (3) |
C1 | 0.00275 (13) | 0.3640 (4) | 0.7234 (3) | 0.0767 (9) | |
H1A | 0.0065 | 0.4283 | 0.7923 | 0.115* | |
H1B | 0.0079 | 0.2639 | 0.7504 | 0.115* | |
H1C | −0.0385 | 0.3760 | 0.6763 | 0.115* | |
C2 | 0.05326 (10) | 0.4012 (3) | 0.6468 (2) | 0.0543 (7) | |
C3 | 0.09182 (10) | 0.5186 (3) | 0.6545 (2) | 0.0492 (6) | |
H3 | 0.0913 | 0.5911 | 0.7132 | 0.059* | |
C4 | 0.13368 (10) | 0.5234 (3) | 0.5652 (2) | 0.0417 (5) | |
C5 | 0.12560 (10) | 0.4047 (3) | 0.4888 (2) | 0.0474 (6) | |
C6 | 0.15693 (13) | 0.3687 (3) | 0.3809 (2) | 0.0638 (7) | |
H6A | 0.1701 | 0.4580 | 0.3458 | 0.096* | |
H6B | 0.1274 | 0.3174 | 0.3222 | 0.096* | |
H6C | 0.1934 | 0.3076 | 0.4052 | 0.096* | |
C7 | 0.26361 (13) | 0.3698 (3) | 0.7000 (2) | 0.0608 (7) | |
H7A | 0.2478 | 0.4552 | 0.7366 | 0.091* | |
H7B | 0.2942 | 0.3207 | 0.7582 | 0.091* | |
H7C | 0.2290 | 0.3042 | 0.6736 | 0.091* | |
C8 | 0.29459 (10) | 0.4155 (3) | 0.5934 (2) | 0.0470 (6) | |
C9 | 0.28314 (9) | 0.5337 (2) | 0.5169 (2) | 0.0381 (5) | |
C10 | 0.32624 (9) | 0.5390 (2) | 0.4305 (2) | 0.0408 (5) | |
H10 | 0.3245 | 0.6119 | 0.3716 | 0.049* | |
C11 | 0.36982 (10) | 0.4300 (3) | 0.4404 (2) | 0.0440 (6) | |
C12 | 0.42332 (10) | 0.4109 (3) | 0.3715 (2) | 0.0449 (6) | |
C13 | 0.41996 (11) | 0.4683 (3) | 0.2558 (2) | 0.0546 (7) | |
H13 | 0.3824 | 0.5127 | 0.2202 | 0.066* | |
C14 | 0.47107 (12) | 0.4614 (3) | 0.1918 (2) | 0.0596 (7) | |
H14 | 0.4680 | 0.5002 | 0.1141 | 0.072* | |
C15 | 0.52625 (11) | 0.3963 (3) | 0.2450 (3) | 0.0561 (7) | |
C16 | 0.53145 (11) | 0.3370 (3) | 0.3583 (3) | 0.0630 (7) | |
H16 | 0.5692 | 0.2924 | 0.3927 | 0.076* | |
C17 | 0.47980 (11) | 0.3438 (3) | 0.4218 (2) | 0.0576 (7) | |
H17 | 0.4831 | 0.3030 | 0.4989 | 0.069* | |
C18 | 0.17644 (10) | 0.6471 (2) | 0.55328 (19) | 0.0388 (5) | |
C19 | 0.15227 (11) | 0.8008 (3) | 0.5657 (2) | 0.0550 (7) | |
C20 | 0.20533 (12) | 0.9030 (3) | 0.5443 (3) | 0.0564 (7) | |
C21 | 0.25575 (11) | 0.8050 (3) | 0.5034 (3) | 0.0531 (6) | |
C22 | 0.23643 (10) | 0.6505 (2) | 0.52638 (19) | 0.0378 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0583 (4) | 0.0657 (5) | 0.0644 (5) | −0.0233 (3) | 0.0112 (3) | 0.0029 (4) |
S2 | 0.0576 (4) | 0.0512 (4) | 0.0683 (5) | 0.0187 (3) | 0.0209 (3) | 0.0120 (3) |
Cl1 | 0.0561 (4) | 0.1090 (7) | 0.1011 (6) | 0.0012 (4) | 0.0410 (4) | −0.0214 (5) |
F1 | 0.081 (4) | 0.063 (2) | 0.097 (5) | 0.005 (2) | 0.059 (4) | −0.013 (3) |
F2 | 0.059 (2) | 0.069 (2) | 0.105 (5) | 0.0173 (17) | −0.012 (3) | 0.006 (2) |
F1' | 0.091 (6) | 0.059 (4) | 0.059 (5) | 0.000 (4) | 0.028 (4) | −0.018 (3) |
F2' | 0.047 (3) | 0.066 (3) | 0.115 (9) | 0.017 (2) | 0.005 (4) | −0.004 (4) |
F3 | 0.069 (2) | 0.077 (4) | 0.084 (3) | −0.006 (2) | 0.016 (2) | −0.038 (3) |
F4 | 0.083 (3) | 0.048 (3) | 0.123 (6) | 0.021 (2) | 0.044 (4) | 0.022 (3) |
F3' | 0.112 (10) | 0.067 (7) | 0.134 (13) | −0.027 (7) | 0.056 (10) | −0.043 (9) |
F4' | 0.082 (5) | 0.118 (13) | 0.097 (8) | 0.036 (7) | 0.024 (5) | 0.049 (8) |
F5 | 0.0425 (16) | 0.0514 (17) | 0.103 (4) | −0.0089 (13) | 0.016 (2) | −0.005 (2) |
F6 | 0.088 (4) | 0.057 (2) | 0.058 (3) | 0.006 (2) | 0.030 (2) | 0.0122 (15) |
F5' | 0.082 (10) | 0.066 (5) | 0.18 (2) | −0.024 (5) | −0.064 (13) | −0.003 (7) |
F6' | 0.118 (18) | 0.055 (6) | 0.17 (2) | 0.018 (9) | 0.113 (17) | 0.038 (11) |
C1 | 0.0528 (16) | 0.105 (2) | 0.076 (2) | −0.0139 (16) | 0.0223 (14) | 0.0232 (18) |
C2 | 0.0380 (12) | 0.0710 (18) | 0.0544 (16) | −0.0060 (13) | 0.0090 (11) | 0.0136 (14) |
C3 | 0.0390 (12) | 0.0613 (16) | 0.0496 (15) | 0.0044 (12) | 0.0146 (11) | 0.0021 (12) |
C4 | 0.0340 (11) | 0.0470 (14) | 0.0457 (14) | 0.0017 (10) | 0.0116 (10) | 0.0021 (11) |
C5 | 0.0439 (13) | 0.0503 (15) | 0.0493 (15) | −0.0075 (11) | 0.0114 (11) | 0.0026 (12) |
C6 | 0.0718 (17) | 0.0647 (17) | 0.0586 (17) | −0.0149 (14) | 0.0224 (14) | −0.0167 (14) |
C7 | 0.0651 (16) | 0.0602 (17) | 0.0612 (17) | 0.0094 (14) | 0.0228 (13) | 0.0158 (14) |
C8 | 0.0442 (12) | 0.0458 (14) | 0.0529 (15) | 0.0026 (11) | 0.0138 (11) | 0.0014 (12) |
C9 | 0.0330 (11) | 0.0373 (12) | 0.0450 (13) | −0.0001 (9) | 0.0086 (9) | −0.0013 (10) |
C10 | 0.0355 (11) | 0.0405 (13) | 0.0479 (14) | 0.0014 (10) | 0.0103 (10) | 0.0028 (10) |
C11 | 0.0396 (12) | 0.0431 (13) | 0.0503 (15) | 0.0031 (10) | 0.0102 (10) | −0.0022 (11) |
C12 | 0.0380 (12) | 0.0427 (13) | 0.0553 (15) | 0.0044 (10) | 0.0113 (11) | −0.0088 (11) |
C13 | 0.0445 (13) | 0.0622 (16) | 0.0587 (17) | 0.0144 (12) | 0.0128 (12) | −0.0010 (13) |
C14 | 0.0576 (15) | 0.0648 (17) | 0.0600 (17) | 0.0101 (14) | 0.0199 (13) | −0.0033 (14) |
C15 | 0.0430 (14) | 0.0566 (16) | 0.0724 (19) | −0.0013 (12) | 0.0206 (13) | −0.0167 (14) |
C16 | 0.0392 (13) | 0.0746 (19) | 0.075 (2) | 0.0163 (13) | 0.0085 (13) | −0.0092 (16) |
C17 | 0.0494 (14) | 0.0614 (17) | 0.0634 (17) | 0.0155 (13) | 0.0128 (12) | 0.0012 (13) |
C18 | 0.0371 (11) | 0.0422 (13) | 0.0384 (13) | 0.0024 (10) | 0.0096 (9) | −0.0026 (10) |
C19 | 0.0394 (13) | 0.0533 (16) | 0.0749 (19) | 0.0070 (12) | 0.0166 (13) | −0.0105 (14) |
C20 | 0.0638 (16) | 0.0377 (15) | 0.0716 (19) | 0.0037 (13) | 0.0227 (14) | −0.0039 (15) |
C21 | 0.0389 (13) | 0.0444 (14) | 0.078 (2) | −0.0027 (11) | 0.0137 (14) | 0.0027 (14) |
C22 | 0.0368 (11) | 0.0385 (12) | 0.0389 (13) | 0.0004 (10) | 0.0087 (9) | −0.0007 (10) |
S1—C2 | 1.718 (3) | C6—H6B | 0.9600 |
S1—C5 | 1.719 (2) | C6—H6C | 0.9600 |
S2—C8 | 1.722 (2) | C7—C8 | 1.498 (3) |
S2—C11 | 1.724 (2) | C7—H7A | 0.9600 |
Cl1—C15 | 1.743 (2) | C7—H7B | 0.9600 |
F1—C19 | 1.258 (7) | C7—H7C | 0.9600 |
F2—C19 | 1.441 (7) | C8—C9 | 1.372 (3) |
F1'—C19 | 1.523 (11) | C9—C10 | 1.422 (3) |
F2'—C19 | 1.266 (8) | C9—C22 | 1.467 (3) |
F3—C20 | 1.420 (7) | C10—C11 | 1.349 (3) |
F4—C20 | 1.298 (6) | C10—H10 | 0.9300 |
F3'—C20 | 1.226 (8) | C11—C12 | 1.470 (3) |
F4'—C20 | 1.478 (12) | C12—C13 | 1.384 (3) |
F5—C21 | 1.320 (6) | C12—C17 | 1.390 (3) |
F6—C21 | 1.422 (8) | C13—C14 | 1.383 (3) |
F5'—C21 | 1.48 (2) | C13—H13 | 0.9300 |
F6'—C21 | 1.16 (2) | C14—C15 | 1.369 (4) |
C1—C2 | 1.502 (3) | C14—H14 | 0.9300 |
C1—H1A | 0.9600 | C15—C16 | 1.363 (4) |
C1—H1B | 0.9600 | C16—C17 | 1.389 (3) |
C1—H1C | 0.9600 | C16—H16 | 0.9300 |
C2—C3 | 1.341 (3) | C17—H17 | 0.9300 |
C3—C4 | 1.428 (3) | C18—C22 | 1.350 (3) |
C3—H3 | 0.9300 | C18—C19 | 1.502 (3) |
C4—C5 | 1.371 (3) | C19—C20 | 1.506 (3) |
C4—C18 | 1.464 (3) | C20—C21 | 1.512 (3) |
C5—C6 | 1.492 (3) | C21—C22 | 1.496 (3) |
C6—H6A | 0.9600 | ||
C2—S1—C5 | 93.27 (12) | C15—C16—H16 | 120.3 |
C8—S2—C11 | 93.15 (11) | C17—C16—H16 | 120.3 |
C2—C1—H1A | 109.5 | C16—C17—C12 | 120.8 (3) |
C2—C1—H1B | 109.5 | C16—C17—H17 | 119.6 |
H1A—C1—H1B | 109.5 | C12—C17—H17 | 119.6 |
C2—C1—H1C | 109.5 | C22—C18—C4 | 130.9 (2) |
H1A—C1—H1C | 109.5 | C22—C18—C19 | 110.20 (19) |
H1B—C1—H1C | 109.5 | C4—C18—C19 | 118.82 (18) |
C3—C2—C1 | 128.5 (3) | F1—C19—F2' | 72.8 (5) |
C3—C2—S1 | 110.02 (18) | F1—C19—F2 | 104.6 (3) |
C1—C2—S1 | 121.5 (2) | F2'—C19—F2 | 33.4 (6) |
C2—C3—C4 | 114.5 (2) | F1—C19—C18 | 119.7 (4) |
C2—C3—H3 | 122.7 | F2'—C19—C18 | 116.4 (4) |
C4—C3—H3 | 122.7 | F2—C19—C18 | 108.1 (3) |
C5—C4—C3 | 112.0 (2) | F1—C19—C20 | 114.1 (4) |
C5—C4—C18 | 124.94 (19) | F2'—C19—C20 | 124.6 (8) |
C3—C4—C18 | 122.9 (2) | F2—C19—C20 | 102.1 (5) |
C4—C5—C6 | 130.0 (2) | C18—C19—C20 | 106.62 (19) |
C4—C5—S1 | 110.15 (17) | F1—C19—F1' | 26.9 (3) |
C6—C5—S1 | 119.76 (18) | F2'—C19—F1' | 99.1 (6) |
C5—C6—H6A | 109.5 | F2—C19—F1' | 131.5 (4) |
C5—C6—H6B | 109.5 | C18—C19—F1' | 103.2 (6) |
H6A—C6—H6B | 109.5 | C20—C19—F1' | 103.3 (5) |
C5—C6—H6C | 109.5 | F3'—C20—F4 | 67.7 (11) |
H6A—C6—H6C | 109.5 | F3'—C20—F3 | 38.1 (12) |
H6B—C6—H6C | 109.5 | F4—C20—F3 | 104.6 (3) |
C8—C7—H7A | 109.5 | F3'—C20—F4' | 103.4 (7) |
C8—C7—H7B | 109.5 | F4—C20—F4' | 36.9 (7) |
H7A—C7—H7B | 109.5 | F3—C20—F4' | 141.2 (9) |
C8—C7—H7C | 109.5 | F3'—C20—C19 | 117.1 (4) |
H7A—C7—H7C | 109.5 | F4—C20—C19 | 120.6 (5) |
H7B—C7—H7C | 109.5 | F3—C20—C19 | 105.9 (4) |
C9—C8—C7 | 130.7 (2) | F4'—C20—C19 | 96.4 (10) |
C9—C8—S2 | 110.39 (17) | F3'—C20—C21 | 127.2 (12) |
C7—C8—S2 | 118.82 (18) | F4—C20—C21 | 116.0 (3) |
C8—C9—C10 | 111.96 (19) | F3—C20—C21 | 102.7 (4) |
C8—C9—C22 | 125.7 (2) | F4'—C20—C21 | 101.6 (8) |
C10—C9—C22 | 122.16 (19) | C19—C20—C21 | 105.2 (2) |
C11—C10—C9 | 114.8 (2) | F6'—C21—F5 | 75 (2) |
C11—C10—H10 | 122.6 | F6'—C21—F6 | 28 (2) |
C9—C10—H10 | 122.6 | F5—C21—F6 | 102.3 (4) |
C10—C11—C12 | 128.0 (2) | F6'—C21—F5' | 107.1 (10) |
C10—C11—S2 | 109.66 (16) | F5—C21—F5' | 33.2 (19) |
C12—C11—S2 | 122.19 (17) | F6—C21—F5' | 134.9 (19) |
C13—C12—C17 | 117.9 (2) | F6'—C21—C22 | 123.9 (16) |
C13—C12—C11 | 120.2 (2) | F5—C21—C22 | 116.9 (4) |
C17—C12—C11 | 121.8 (2) | F6—C21—C22 | 108.4 (4) |
C14—C13—C12 | 121.6 (2) | F5'—C21—C22 | 102.5 (10) |
C14—C13—H13 | 119.2 | F6'—C21—C20 | 116.9 (10) |
C12—C13—H13 | 119.2 | F5—C21—C20 | 116.2 (3) |
C15—C14—C13 | 118.8 (3) | F6—C21—C20 | 106.2 (4) |
C15—C14—H14 | 120.6 | F5'—C21—C20 | 95.5 (17) |
C13—C14—H14 | 120.6 | C22—C21—C20 | 106.2 (2) |
C16—C15—C14 | 121.5 (2) | C18—C22—C9 | 132.0 (2) |
C16—C15—Cl1 | 119.4 (2) | C18—C22—C21 | 110.48 (19) |
C14—C15—Cl1 | 119.0 (2) | C9—C22—C21 | 117.55 (18) |
C15—C16—C17 | 119.3 (2) | ||
C5—S1—C2—C3 | −0.5 (2) | C18—C19—C20—F4 | 140.9 (7) |
C5—S1—C2—C1 | 178.2 (2) | F1'—C19—C20—F4 | −110.7 (10) |
C1—C2—C3—C4 | −178.3 (2) | F1—C19—C20—F3 | 33.6 (9) |
S1—C2—C3—C4 | 0.4 (3) | F2'—C19—C20—F3 | 118.7 (12) |
C2—C3—C4—C5 | 0.0 (3) | F2—C19—C20—F3 | 145.8 (7) |
C2—C3—C4—C18 | 175.9 (2) | C18—C19—C20—F3 | −100.9 (5) |
C3—C4—C5—C6 | 177.2 (2) | F1'—C19—C20—F3 | 7.5 (9) |
C18—C4—C5—C6 | 1.4 (4) | F1—C19—C20—F4' | −114.3 (13) |
C3—C4—C5—S1 | −0.4 (3) | F2'—C19—C20—F4' | −29.2 (15) |
C18—C4—C5—S1 | −176.15 (18) | F2—C19—C20—F4' | −2.0 (11) |
C2—S1—C5—C4 | 0.50 (19) | C18—C19—C20—F4' | 111.3 (11) |
C2—S1—C5—C6 | −177.4 (2) | F1'—C19—C20—F4' | −140.4 (12) |
C11—S2—C8—C9 | −0.02 (19) | F1—C19—C20—C21 | 141.8 (7) |
C11—S2—C8—C7 | −177.2 (2) | F2'—C19—C20—C21 | −133.1 (11) |
C7—C8—C9—C10 | 177.1 (2) | F2—C19—C20—C21 | −105.9 (5) |
S2—C8—C9—C10 | 0.4 (2) | C18—C19—C20—C21 | 7.4 (3) |
C7—C8—C9—C22 | 2.2 (4) | F1'—C19—C20—C21 | 115.8 (7) |
S2—C8—C9—C22 | −174.46 (17) | F3'—C20—C21—F6' | −85 (3) |
C8—C9—C10—C11 | −0.6 (3) | F4—C20—C21—F6' | −4 (3) |
C22—C9—C10—C11 | 174.4 (2) | F3—C20—C21—F6' | −118 (3) |
C9—C10—C11—C12 | −175.1 (2) | F4'—C20—C21—F6' | 32 (3) |
C9—C10—C11—S2 | 0.6 (2) | C19—C20—C21—F6' | 132 (3) |
C8—S2—C11—C10 | −0.33 (18) | F3'—C20—C21—F5 | 0.2 (19) |
C8—S2—C11—C12 | 175.6 (2) | F4—C20—C21—F5 | 81.1 (10) |
C10—C11—C12—C13 | −27.2 (4) | F3—C20—C21—F5 | −32.3 (8) |
S2—C11—C12—C13 | 157.63 (19) | F4'—C20—C21—F5 | 117.1 (14) |
C10—C11—C12—C17 | 148.8 (2) | C19—C20—C21—F5 | −142.9 (5) |
S2—C11—C12—C17 | −26.4 (3) | F3'—C20—C21—F6 | −112.7 (18) |
C17—C12—C13—C14 | −0.7 (4) | F4—C20—C21—F6 | −31.9 (9) |
C11—C12—C13—C14 | 175.4 (2) | F3—C20—C21—F6 | −145.2 (6) |
C12—C13—C14—C15 | −0.2 (4) | F4'—C20—C21—F6 | 4.2 (13) |
C13—C14—C15—C16 | 0.8 (4) | C19—C20—C21—F6 | 104.2 (4) |
C13—C14—C15—Cl1 | −179.3 (2) | F3'—C20—C21—F5' | 27 (2) |
C14—C15—C16—C17 | −0.6 (4) | F4—C20—C21—F5' | 108.2 (18) |
Cl1—C15—C16—C17 | 179.6 (2) | F3—C20—C21—F5' | −5.2 (16) |
C15—C16—C17—C12 | −0.4 (4) | F4'—C20—C21—F5' | 144 (2) |
C13—C12—C17—C16 | 1.0 (4) | C19—C20—C21—F5' | −115.8 (16) |
C11—C12—C17—C16 | −175.0 (2) | F3'—C20—C21—C22 | 132.1 (18) |
C5—C4—C18—C22 | −42.4 (4) | F4—C20—C21—C22 | −147.1 (8) |
C3—C4—C18—C22 | 142.2 (2) | F3—C20—C21—C22 | 99.5 (5) |
C5—C4—C18—C19 | 134.1 (2) | F4'—C20—C21—C22 | −111.1 (13) |
C3—C4—C18—C19 | −41.2 (3) | C19—C20—C21—C22 | −11.1 (3) |
C22—C18—C19—F1 | −132.0 (7) | C4—C18—C22—C9 | −10.2 (4) |
C4—C18—C19—F1 | 50.8 (7) | C19—C18—C22—C9 | 173.0 (2) |
C22—C18—C19—F2' | 143.6 (12) | C4—C18—C22—C21 | 170.0 (2) |
C4—C18—C19—F2' | −33.6 (12) | C19—C18—C22—C21 | −6.8 (3) |
C22—C18—C19—F2 | 108.6 (6) | C8—C9—C22—C18 | −40.8 (4) |
C4—C18—C19—F2 | −68.6 (6) | C10—C9—C22—C18 | 144.9 (2) |
C22—C18—C19—C20 | −0.6 (3) | C8—C9—C22—C21 | 139.0 (2) |
C4—C18—C19—C20 | −177.8 (2) | C10—C9—C22—C21 | −35.3 (3) |
C22—C18—C19—F1' | −109.0 (6) | F6'—C21—C22—C18 | −128 (3) |
C4—C18—C19—F1' | 73.8 (6) | F5—C21—C22—C18 | 142.9 (5) |
F1—C19—C20—F3' | −6 (2) | F6—C21—C22—C18 | −102.3 (4) |
F2'—C19—C20—F3' | 79 (2) | F5'—C21—C22—C18 | 111 (2) |
F2—C19—C20—F3' | 107 (2) | C20—C21—C22—C18 | 11.4 (3) |
C18—C19—C20—F3' | −140 (2) | F6'—C21—C22—C9 | 52 (3) |
F1'—C19—C20—F3' | −32 (2) | F5—C21—C22—C9 | −37.0 (5) |
F1—C19—C20—F4 | −84.7 (10) | F6—C21—C22—C9 | 77.8 (5) |
F2'—C19—C20—F4 | 0.4 (13) | F5'—C21—C22—C9 | −69 (2) |
F2—C19—C20—F4 | 27.6 (8) | C20—C21—C22—C9 | −168.5 (2) |