Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003285/kj2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003285/kj2041Isup2.hkl |
CCDC reference: 615590
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.
C22H15ClF6S2 | Dx = 1.499 Mg m−3 |
Mr = 492.91 | Melting point: 354 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9539 (12) Å | Cell parameters from 3439 reflections |
b = 21.661 (4) Å | θ = 2.8–24.9° |
c = 14.543 (2) Å | µ = 0.42 mm−1 |
β = 94.278 (3)° | T = 294 K |
V = 2184.5 (6) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.27 × 0.21 mm |
F(000) = 1000 |
Bruker SMART APEX2 CCD area-detector diffractometer | 3841 independent reflections |
Radiation source: fine-focus sealed tube | 2519 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→7 |
Tmin = 0.866, Tmax = 0.916 | k = −18→25 |
10959 measured reflections | l = −17→17 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0446P)2 + 0.7775P] where P = (Fo2 + 2Fc2)/3 |
3841 reflections | (Δ/σ)max = 0.005 |
311 parameters | Δρmax = 0.23 e Å−3 |
64 restraints | Δρmin = −0.21 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) | |
C8 | 0.1151 (2) | 0.83335 (7) | 0.91066 (10) | 0.0552 (4) | 0.9036 (7) |
F1 | 0.24123 (16) | 0.79949 (4) | 0.96606 (6) | 0.0771 (3) | 0.9036 (7) |
F2 | −0.04565 (14) | 0.79788 (5) | 0.90063 (7) | 0.0831 (3) | 0.9036 (7) |
C9 | 0.0726 (2) | 0.89515 (7) | 0.95687 (10) | 0.0602 (5) | 0.9036 (7) |
F3 | 0.11533 (17) | 0.89499 (5) | 1.04803 (6) | 0.0842 (4) | 0.9036 (7) |
F4 | −0.11775 (15) | 0.90753 (5) | 0.94060 (8) | 0.0937 (4) | 0.9036 (7) |
C10 | 0.1880 (2) | 0.94173 (7) | 0.90493 (10) | 0.0585 (5) | 0.9036 (7) |
F5 | 0.35556 (16) | 0.95452 (5) | 0.95492 (6) | 0.0913 (4) | 0.9036 (7) |
F6 | 0.09423 (18) | 0.99596 (4) | 0.89349 (7) | 0.0921 (4) | 0.9036 (7) |
C8' | 0.1212 (6) | 0.8297 (2) | 0.9104 (3) | 0.0552 (4) | 0.0964 (7) |
F1' | 0.2813 (9) | 0.8034 (4) | 0.9535 (6) | 0.0771 (3) | 0.0964 (7) |
F2' | −0.0503 (8) | 0.7993 (4) | 0.9073 (7) | 0.0831 (3) | 0.0964 (7) |
C9' | 0.0962 (7) | 0.8911 (2) | 0.9611 (3) | 0.0602 (5) | 0.0964 (7) |
F3' | 0.2315 (10) | 0.8966 (4) | 1.0329 (4) | 0.0842 (4) | 0.0964 (7) |
F4' | −0.0714 (8) | 0.8986 (5) | 1.0023 (6) | 0.0937 (4) | 0.0964 (7) |
C10' | 0.1390 (7) | 0.9430 (2) | 0.8948 (3) | 0.0585 (5) | 0.0964 (7) |
F5' | 0.2530 (11) | 0.9888 (3) | 0.9325 (6) | 0.0913 (4) | 0.0964 (7) |
F6' | −0.0294 (9) | 0.9738 (4) | 0.8753 (6) | 0.0921 (4) | 0.0964 (7) |
S1 | 0.40682 (6) | 0.734694 (18) | 0.64092 (3) | 0.06876 (13) | |
S2 | 0.30771 (5) | 0.996484 (16) | 0.57918 (2) | 0.04925 (10) | |
Cl1 | 0.39033 (6) | 1.139927 (18) | 0.53925 (3) | 0.07499 (13) | |
C1 | 0.0904 (3) | 0.65315 (7) | 0.62802 (13) | 0.0935 (7) | |
H1A | −0.0348 | 0.6480 | 0.6506 | 0.140* | |
H1B | 0.1694 | 0.6181 | 0.6453 | 0.140* | |
H1C | 0.0776 | 0.6567 | 0.5620 | 0.140* | |
C2 | 0.1831 (2) | 0.71093 (6) | 0.66896 (10) | 0.0612 (5) | |
C3 | 0.1131 (2) | 0.75016 (6) | 0.73036 (9) | 0.0520 (4) | |
H3 | −0.0059 | 0.7448 | 0.7545 | 0.062* | |
C4 | 0.23860 (19) | 0.80078 (6) | 0.75487 (9) | 0.0432 (4) | |
C5 | 0.40745 (19) | 0.79790 (6) | 0.71212 (9) | 0.0507 (4) | |
C6 | 0.5825 (2) | 0.83842 (8) | 0.72273 (12) | 0.0739 (5) | |
H6A | 0.5702 | 0.8712 | 0.6783 | 0.111* | |
H6B | 0.6952 | 0.8144 | 0.7129 | 0.111* | |
H6C | 0.5942 | 0.8555 | 0.7838 | 0.111* | |
C7 | 0.19373 (18) | 0.84961 (6) | 0.82046 (8) | 0.0427 (4) | |
C11 | 0.22222 (18) | 0.91096 (6) | 0.81520 (8) | 0.0440 (4) | |
C12 | 0.28329 (18) | 0.94848 (5) | 0.73772 (8) | 0.0422 (4) | |
C13 | 0.20118 (18) | 0.94493 (6) | 0.64967 (9) | 0.0437 (4) | |
C14 | 0.0348 (2) | 0.90649 (7) | 0.61052 (10) | 0.0610 (5) | |
H14A | 0.0804 | 0.8663 | 0.5950 | 0.091* | |
H14B | −0.0235 | 0.9261 | 0.5561 | 0.091* | |
H14C | −0.0589 | 0.9026 | 0.6554 | 0.091* | |
C15 | 0.43252 (19) | 0.99374 (6) | 0.74792 (9) | 0.0455 (4) | |
H15 | 0.5009 | 1.0021 | 0.8039 | 0.055* | |
C16 | 0.46566 (18) | 1.02350 (6) | 0.66816 (9) | 0.0443 (4) | |
C17 | 0.62270 (17) | 1.06838 (6) | 0.65590 (9) | 0.0435 (4) | |
C18 | 0.8019 (2) | 1.05817 (7) | 0.70357 (10) | 0.0606 (5) | |
H18 | 0.8196 | 1.0228 | 0.7395 | 0.073* | |
C19 | 0.9530 (2) | 1.09885 (7) | 0.69890 (12) | 0.0715 (5) | |
H19 | 1.0705 | 1.0908 | 0.7315 | 0.086* | |
C20 | 0.9303 (2) | 1.15120 (7) | 0.64615 (11) | 0.0677 (5) | |
H20 | 1.0318 | 1.1789 | 0.6435 | 0.081* | |
C21 | 0.7578 (2) | 1.16253 (6) | 0.59739 (10) | 0.0583 (4) | |
H21 | 0.7427 | 1.1978 | 0.5611 | 0.070* | |
C22 | 0.60573 (19) | 1.12160 (6) | 0.60199 (9) | 0.0492 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C8 | 0.0705 (9) | 0.0449 (8) | 0.0510 (8) | −0.0049 (7) | 0.0103 (7) | 0.0036 (7) |
F1 | 0.1159 (7) | 0.0618 (5) | 0.0543 (5) | 0.0168 (5) | 0.0112 (5) | 0.0147 (4) |
F2 | 0.0975 (6) | 0.0823 (6) | 0.0740 (5) | −0.0374 (5) | 0.0374 (5) | −0.0084 (5) |
C9 | 0.0776 (10) | 0.0583 (9) | 0.0466 (8) | 0.0051 (7) | 0.0179 (7) | −0.0005 (7) |
F3 | 0.1402 (9) | 0.0723 (6) | 0.0435 (5) | −0.0006 (6) | 0.0282 (5) | −0.0020 (4) |
F4 | 0.0828 (6) | 0.0908 (7) | 0.1107 (8) | 0.0174 (6) | 0.0285 (6) | −0.0065 (6) |
C10 | 0.0840 (10) | 0.0414 (8) | 0.0499 (8) | 0.0000 (7) | 0.0040 (8) | −0.0030 (7) |
F5 | 0.1177 (8) | 0.0980 (7) | 0.0564 (5) | −0.0432 (6) | −0.0058 (5) | −0.0102 (5) |
F6 | 0.1624 (9) | 0.0460 (5) | 0.0719 (6) | 0.0264 (6) | 0.0363 (6) | −0.0014 (5) |
C8' | 0.0705 (9) | 0.0449 (8) | 0.0510 (8) | −0.0049 (7) | 0.0103 (7) | 0.0036 (7) |
F1' | 0.1159 (7) | 0.0618 (5) | 0.0543 (5) | 0.0168 (5) | 0.0112 (5) | 0.0147 (4) |
F2' | 0.0975 (6) | 0.0823 (6) | 0.0740 (5) | −0.0374 (5) | 0.0374 (5) | −0.0084 (5) |
C9' | 0.0776 (10) | 0.0583 (9) | 0.0466 (8) | 0.0051 (7) | 0.0179 (7) | −0.0005 (7) |
F3' | 0.1402 (9) | 0.0723 (6) | 0.0435 (5) | −0.0006 (6) | 0.0282 (5) | −0.0020 (4) |
F4' | 0.0828 (6) | 0.0908 (7) | 0.1107 (8) | 0.0174 (6) | 0.0285 (6) | −0.0065 (6) |
C10' | 0.0840 (10) | 0.0414 (8) | 0.0499 (8) | 0.0000 (7) | 0.0040 (8) | −0.0030 (7) |
F5' | 0.1177 (8) | 0.0980 (7) | 0.0564 (5) | −0.0432 (6) | −0.0058 (5) | −0.0102 (5) |
F6' | 0.1624 (9) | 0.0460 (5) | 0.0719 (6) | 0.0264 (6) | 0.0363 (6) | −0.0014 (5) |
S1 | 0.0931 (3) | 0.0541 (2) | 0.0618 (2) | 0.0170 (2) | 0.0238 (2) | −0.00288 (19) |
S2 | 0.05292 (18) | 0.04933 (19) | 0.04506 (18) | −0.01053 (16) | 0.00071 (15) | 0.00518 (15) |
Cl1 | 0.0606 (2) | 0.0590 (2) | 0.1037 (3) | −0.00362 (18) | −0.0054 (2) | 0.0286 (2) |
C1 | 0.1250 (15) | 0.0552 (10) | 0.0965 (13) | −0.0068 (10) | −0.0167 (12) | −0.0195 (9) |
C2 | 0.0852 (10) | 0.0436 (8) | 0.0539 (9) | 0.0037 (7) | −0.0013 (8) | −0.0012 (7) |
C3 | 0.0592 (8) | 0.0422 (7) | 0.0548 (8) | −0.0040 (6) | 0.0067 (7) | 0.0009 (6) |
C4 | 0.0509 (7) | 0.0369 (7) | 0.0424 (7) | 0.0016 (6) | 0.0070 (6) | 0.0054 (6) |
C5 | 0.0536 (8) | 0.0447 (7) | 0.0547 (8) | 0.0050 (6) | 0.0101 (6) | 0.0039 (7) |
C6 | 0.0512 (8) | 0.0708 (10) | 0.1020 (12) | 0.0038 (8) | 0.0209 (8) | 0.0028 (9) |
C7 | 0.0443 (7) | 0.0391 (7) | 0.0449 (7) | −0.0024 (6) | 0.0047 (6) | 0.0016 (6) |
C11 | 0.0481 (7) | 0.0408 (7) | 0.0430 (7) | −0.0024 (6) | 0.0026 (6) | −0.0017 (6) |
C12 | 0.0492 (7) | 0.0330 (6) | 0.0445 (7) | −0.0018 (6) | 0.0032 (6) | 0.0005 (6) |
C13 | 0.0453 (7) | 0.0387 (7) | 0.0473 (7) | −0.0017 (6) | 0.0050 (6) | 0.0011 (6) |
C14 | 0.0620 (9) | 0.0622 (9) | 0.0571 (9) | −0.0160 (7) | −0.0062 (7) | 0.0021 (7) |
C15 | 0.0537 (7) | 0.0375 (7) | 0.0445 (7) | −0.0025 (6) | −0.0019 (6) | −0.0009 (6) |
C16 | 0.0425 (7) | 0.0375 (7) | 0.0528 (8) | −0.0014 (6) | 0.0023 (6) | −0.0030 (6) |
C17 | 0.0450 (7) | 0.0380 (7) | 0.0481 (7) | −0.0018 (6) | 0.0077 (6) | −0.0058 (6) |
C18 | 0.0535 (8) | 0.0550 (9) | 0.0722 (9) | −0.0054 (7) | −0.0022 (7) | −0.0013 (8) |
C19 | 0.0497 (8) | 0.0694 (10) | 0.0937 (12) | −0.0079 (8) | −0.0050 (8) | −0.0075 (9) |
C20 | 0.0548 (8) | 0.0623 (9) | 0.0879 (10) | −0.0198 (7) | 0.0187 (8) | −0.0159 (8) |
C21 | 0.0623 (8) | 0.0423 (8) | 0.0727 (9) | −0.0078 (7) | 0.0211 (7) | −0.0045 (7) |
C22 | 0.0474 (7) | 0.0440 (7) | 0.0572 (8) | −0.0001 (6) | 0.0102 (6) | −0.0033 (6) |
C8—F2 | 1.3555 (18) | C3—C4 | 1.4299 (18) |
C8—F1 | 1.3603 (17) | C3—H3 | 0.9300 |
C8—C7 | 1.5002 (19) | C4—C5 | 1.3703 (19) |
C8—C9 | 1.537 (2) | C4—C7 | 1.4733 (17) |
C9—F3 | 1.3369 (17) | C5—C6 | 1.499 (2) |
C9—F4 | 1.3537 (19) | C6—H6A | 0.9600 |
C9—C10 | 1.524 (2) | C6—H6B | 0.9600 |
C10—F6 | 1.3479 (17) | C6—H6C | 0.9600 |
C10—F5 | 1.3549 (18) | C7—C11 | 1.3467 (18) |
C10—C11 | 1.5000 (19) | C11—C12 | 1.4770 (18) |
C8'—F2' | 1.360 (7) | C12—C13 | 1.3647 (17) |
C8'—F1' | 1.360 (7) | C12—C15 | 1.4272 (17) |
C8'—C7 | 1.501 (5) | C13—C14 | 1.5029 (19) |
C8'—C9' | 1.537 (6) | C14—H14A | 0.9600 |
C9'—F3' | 1.358 (7) | C14—H14B | 0.9600 |
C9'—F4' | 1.359 (7) | C14—H14C | 0.9600 |
C9'—C10' | 1.524 (6) | C15—C16 | 1.3616 (18) |
C10'—F5' | 1.360 (7) | C15—H15 | 0.9300 |
C10'—F6' | 1.360 (7) | C16—C17 | 1.4827 (18) |
C10'—C11 | 1.502 (5) | C17—C22 | 1.3941 (18) |
S1—C2 | 1.7162 (17) | C17—C18 | 1.3979 (18) |
S1—C5 | 1.7164 (14) | C18—C19 | 1.377 (2) |
S2—C13 | 1.7204 (13) | C18—H18 | 0.9300 |
S2—C16 | 1.7353 (13) | C19—C20 | 1.371 (2) |
Cl1—C22 | 1.7406 (14) | C19—H19 | 0.9300 |
C1—C2 | 1.510 (2) | C20—C21 | 1.369 (2) |
C1—H1A | 0.9600 | C20—H20 | 0.9300 |
C1—H1B | 0.9600 | C21—C22 | 1.3854 (19) |
C1—H1C | 0.9600 | C21—H21 | 0.9300 |
C2—C3 | 1.350 (2) | ||
F2—C8—F1 | 104.37 (11) | C6—C5—S1 | 119.64 (11) |
F2—C8—C7 | 112.97 (11) | C5—C6—H6A | 109.5 |
F1—C8—C7 | 112.57 (12) | C5—C6—H6B | 109.5 |
F2—C8—C9 | 110.88 (13) | H6A—C6—H6B | 109.5 |
F1—C8—C9 | 110.34 (12) | C5—C6—H6C | 109.5 |
C7—C8—C9 | 105.82 (11) | H6A—C6—H6C | 109.5 |
F3—C9—F4 | 108.43 (13) | H6B—C6—H6C | 109.5 |
F3—C9—C10 | 113.99 (13) | C11—C7—C4 | 129.24 (12) |
F4—C9—C10 | 109.06 (12) | C11—C7—C8 | 110.25 (11) |
F3—C9—C8 | 113.30 (12) | C4—C7—C8 | 120.41 (11) |
F4—C9—C8 | 108.30 (12) | C11—C7—C8' | 113.2 (2) |
C10—C9—C8 | 103.54 (12) | C4—C7—C8' | 117.3 (2) |
F6—C10—F5 | 106.07 (12) | C8—C7—C8' | 3.46 (19) |
F6—C10—C11 | 112.73 (12) | C7—C11—C12 | 129.65 (12) |
F5—C10—C11 | 111.84 (13) | C7—C11—C10 | 110.82 (11) |
F6—C10—C9 | 111.71 (13) | C12—C11—C10 | 119.50 (11) |
F5—C10—C9 | 109.46 (12) | C7—C11—C10' | 110.2 (2) |
C11—C10—C9 | 105.10 (11) | C12—C11—C10' | 118.9 (2) |
F2'—C8'—F1' | 119.9 (6) | C10—C11—C10' | 13.84 (19) |
F2'—C8'—C7 | 117.5 (5) | C13—C12—C15 | 112.72 (11) |
F1'—C8'—C7 | 101.8 (5) | C13—C12—C11 | 124.11 (11) |
F2'—C8'—C9' | 107.7 (5) | C15—C12—C11 | 123.15 (11) |
F1'—C8'—C9' | 105.1 (5) | C12—C13—C14 | 130.02 (12) |
C7—C8'—C9' | 103.1 (3) | C12—C13—S2 | 110.73 (9) |
F3'—C9'—F4' | 102.6 (6) | C14—C13—S2 | 119.17 (10) |
F3'—C9'—C10' | 105.3 (5) | C13—C14—H14A | 109.5 |
F4'—C9'—C10' | 113.9 (6) | C13—C14—H14B | 109.5 |
F3'—C9'—C8' | 110.4 (5) | H14A—C14—H14B | 109.5 |
F4'—C9'—C8' | 116.5 (6) | C13—C14—H14C | 109.5 |
C10'—C9'—C8' | 107.5 (4) | H14A—C14—H14C | 109.5 |
F5'—C10'—F6' | 101.1 (6) | H14B—C14—H14C | 109.5 |
F5'—C10'—C11 | 113.6 (5) | C16—C15—C12 | 113.87 (11) |
F6'—C10'—C11 | 116.2 (5) | C16—C15—H15 | 123.1 |
F5'—C10'—C9' | 114.8 (5) | C12—C15—H15 | 123.1 |
F6'—C10'—C9' | 106.7 (5) | C15—C16—C17 | 125.86 (11) |
C11—C10'—C9' | 104.6 (3) | C15—C16—S2 | 109.73 (9) |
C2—S1—C5 | 93.29 (7) | C17—C16—S2 | 124.22 (10) |
C13—S2—C16 | 92.94 (6) | C22—C17—C18 | 116.40 (12) |
C2—C1—H1A | 109.5 | C22—C17—C16 | 125.28 (11) |
C2—C1—H1B | 109.5 | C18—C17—C16 | 118.29 (11) |
H1A—C1—H1B | 109.5 | C19—C18—C17 | 121.98 (14) |
C2—C1—H1C | 109.5 | C19—C18—H18 | 119.0 |
H1A—C1—H1C | 109.5 | C17—C18—H18 | 119.0 |
H1B—C1—H1C | 109.5 | C20—C19—C18 | 120.02 (14) |
C3—C2—C1 | 128.17 (15) | C20—C19—H19 | 120.0 |
C3—C2—S1 | 110.29 (11) | C18—C19—H19 | 120.0 |
C1—C2—S1 | 121.54 (12) | C21—C20—C19 | 119.85 (14) |
C2—C3—C4 | 113.81 (13) | C21—C20—H20 | 120.1 |
C2—C3—H3 | 123.1 | C19—C20—H20 | 120.1 |
C4—C3—H3 | 123.1 | C20—C21—C22 | 120.16 (13) |
C5—C4—C3 | 112.33 (12) | C20—C21—H21 | 119.9 |
C5—C4—C7 | 123.81 (12) | C22—C21—H21 | 119.9 |
C3—C4—C7 | 123.85 (12) | C21—C22—C17 | 121.57 (12) |
C4—C5—C6 | 130.04 (13) | C21—C22—Cl1 | 117.30 (10) |
C4—C5—S1 | 110.26 (10) | C17—C22—Cl1 | 121.12 (10) |
F2—C8—C9—F3 | 95.68 (15) | F2'—C8'—C7—C4 | −63.4 (5) |
F1—C8—C9—F3 | −19.45 (18) | F1'—C8'—C7—C4 | 69.7 (5) |
C7—C8—C9—F3 | −141.48 (13) | C9'—C8'—C7—C4 | 178.4 (2) |
F2—C8—C9—F4 | −24.64 (16) | F2'—C8'—C7—C8 | 90 (3) |
F1—C8—C9—F4 | −139.77 (13) | F1'—C8'—C7—C8 | −137 (3) |
C7—C8—C9—F4 | 98.20 (13) | C9'—C8'—C7—C8 | −28 (3) |
F2—C8—C9—C10 | −140.33 (12) | C4—C7—C11—C12 | 8.7 (2) |
F1—C8—C9—C10 | 104.54 (13) | C8—C7—C11—C12 | −175.01 (13) |
C7—C8—C9—C10 | −17.49 (15) | C8'—C7—C11—C12 | −176.9 (2) |
F3—C9—C10—F6 | −92.99 (15) | C4—C7—C11—C10 | −169.76 (13) |
F4—C9—C10—F6 | 28.34 (16) | C8—C7—C11—C10 | 6.54 (15) |
C8—C9—C10—F6 | 143.48 (12) | C8'—C7—C11—C10 | 4.6 (2) |
F3—C9—C10—F5 | 24.19 (18) | C4—C7—C11—C10' | 175.5 (2) |
F4—C9—C10—F5 | 145.52 (12) | C8—C7—C11—C10' | −8.2 (2) |
C8—C9—C10—F5 | −99.34 (13) | C8'—C7—C11—C10' | −10.1 (3) |
F3—C9—C10—C11 | 144.46 (12) | F6—C10—C11—C7 | −139.73 (13) |
F4—C9—C10—C11 | −94.21 (14) | F5—C10—C11—C7 | 100.85 (14) |
C8—C9—C10—C11 | 20.92 (15) | C9—C10—C11—C7 | −17.83 (15) |
F2'—C8'—C9'—F3' | 125.5 (7) | F6—C10—C11—C12 | 41.65 (18) |
F1'—C8'—C9'—F3' | −3.4 (7) | F5—C10—C11—C12 | −77.78 (15) |
C7—C8'—C9'—F3' | −109.7 (5) | C9—C10—C11—C12 | 163.54 (12) |
F2'—C8'—C9'—F4' | 9.0 (8) | F6—C10—C11—C10' | −49.8 (8) |
F1'—C8'—C9'—F4' | −119.9 (7) | F5—C10—C11—C10' | −169.3 (8) |
C7—C8'—C9'—F4' | 133.8 (5) | C9—C10—C11—C10' | 72.1 (8) |
F2'—C8'—C9'—C10' | −120.2 (6) | F5'—C10'—C11—C7 | 138.5 (4) |
F1'—C8'—C9'—C10' | 111.0 (5) | F6'—C10'—C11—C7 | −104.9 (5) |
C7—C8'—C9'—C10' | 4.7 (4) | C9'—C10'—C11—C7 | 12.5 (4) |
F3'—C9'—C10'—F5' | −17.6 (7) | F5'—C10'—C11—C12 | −53.1 (5) |
F4'—C9'—C10'—F5' | 94.0 (7) | F6'—C10'—C11—C12 | 63.5 (5) |
C8'—C9'—C10'—F5' | −135.3 (5) | C9'—C10'—C11—C12 | −179.1 (2) |
F3'—C9'—C10'—F6' | −128.7 (6) | F5'—C10'—C11—C10 | 43.1 (7) |
F4'—C9'—C10'—F6' | −17.1 (7) | F6'—C10'—C11—C10 | 159.8 (11) |
C8'—C9'—C10'—F6' | 113.6 (5) | C9'—C10'—C11—C10 | −82.9 (8) |
F3'—C9'—C10'—C11 | 107.6 (5) | C7—C11—C12—C13 | 49.6 (2) |
F4'—C9'—C10'—C11 | −140.7 (5) | C10—C11—C12—C13 | −132.07 (14) |
C8'—C9'—C10'—C11 | −10.1 (4) | C10'—C11—C12—C13 | −116.2 (2) |
C5—S1—C2—C3 | 0.05 (11) | C7—C11—C12—C15 | −132.06 (15) |
C5—S1—C2—C1 | −179.29 (13) | C10—C11—C12—C15 | 46.27 (18) |
C1—C2—C3—C4 | −179.92 (14) | C10'—C11—C12—C15 | 62.1 (3) |
S1—C2—C3—C4 | 0.81 (15) | C15—C12—C13—C14 | −176.41 (13) |
C2—C3—C4—C5 | −1.53 (17) | C11—C12—C13—C14 | 2.1 (2) |
C2—C3—C4—C7 | 179.95 (12) | C15—C12—C13—S2 | 0.48 (14) |
C3—C4—C5—C6 | −175.44 (14) | C11—C12—C13—S2 | 178.97 (10) |
C7—C4—C5—C6 | 3.1 (2) | C16—S2—C13—C12 | 0.12 (10) |
C3—C4—C5—S1 | 1.49 (14) | C16—S2—C13—C14 | 177.39 (11) |
C7—C4—C5—S1 | −179.98 (10) | C13—C12—C15—C16 | −1.06 (16) |
C2—S1—C5—C4 | −0.90 (11) | C11—C12—C15—C16 | −179.56 (12) |
C2—S1—C5—C6 | 176.40 (12) | C12—C15—C16—C17 | −174.06 (12) |
C5—C4—C7—C11 | 43.4 (2) | C12—C15—C16—S2 | 1.11 (14) |
C3—C4—C7—C11 | −138.24 (14) | C13—S2—C16—C15 | −0.71 (10) |
C5—C4—C7—C8 | −132.56 (14) | C13—S2—C16—C17 | 174.56 (11) |
C3—C4—C7—C8 | 45.79 (18) | C15—C16—C17—C22 | −141.76 (14) |
C5—C4—C7—C8' | −130.8 (2) | S2—C16—C17—C22 | 43.74 (18) |
C3—C4—C7—C8' | 47.6 (2) | C15—C16—C17—C18 | 36.48 (19) |
F2—C8—C7—C11 | 128.84 (13) | S2—C16—C17—C18 | −138.02 (12) |
F1—C8—C7—C11 | −113.25 (13) | C22—C17—C18—C19 | 1.0 (2) |
C9—C8—C7—C11 | 7.34 (15) | C16—C17—C18—C19 | −177.39 (14) |
F2—C8—C7—C4 | −54.48 (17) | C17—C18—C19—C20 | −0.1 (2) |
F1—C8—C7—C4 | 63.43 (16) | C18—C19—C20—C21 | −0.7 (2) |
C9—C8—C7—C4 | −175.98 (12) | C19—C20—C21—C22 | 0.7 (2) |
F2—C8—C7—C8' | −82 (3) | C20—C21—C22—C17 | 0.3 (2) |
F1—C8—C7—C8' | 36 (3) | C20—C21—C22—Cl1 | 179.11 (12) |
C9—C8—C7—C8' | 157 (3) | C18—C17—C22—C21 | −1.1 (2) |
F2'—C8'—C7—C11 | 121.5 (5) | C16—C17—C22—C21 | 177.21 (13) |
F1'—C8'—C7—C11 | −105.4 (4) | C18—C17—C22—Cl1 | −179.87 (11) |
C9'—C8'—C7—C11 | 3.3 (3) | C16—C17—C22—Cl1 | −1.61 (19) |