Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020812/hb2077sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020812/hb2077Iasup2.hkl |
CCDC reference: 613696
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.
C29H22F6O2S2 | F(000) = 1192 |
Mr = 580.59 | Dx = 1.429 Mg m−3 |
Monoclinic, P21/n | Melting point: 389.3 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8013 (11) Å | Cell parameters from 4421 reflections |
b = 26.675 (4) Å | θ = 2.2–27.1° |
c = 12.9844 (18) Å | µ = 0.27 mm−1 |
β = 92.654 (3)° | T = 294 K |
V = 2699.2 (7) Å3 | Prism, colorless |
Z = 4 | 0.42 × 0.40 × 0.30 mm |
Bruker SMART CCD diffractometer | 4782 independent reflections |
Radiation source: fine-focus sealed tube | 3208 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −7→9 |
Tmin = 0.755, Tmax = 1.000 | k = −31→31 |
13656 measured reflections | l = −14→15 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0795P)2 + 2.3881P] where P = (Fo2 + 2Fc2)/3 |
4782 reflections | (Δ/σ)max = 0.003 |
364 parameters | Δρmax = 0.94 e Å−3 |
14 restraints | Δρmin = −0.55 e Å−3 |
Experimental. 1H NMR (400 MHz, CDCl3): δ 1.86 (s, 6H, –CH3), 3.88 (s, 6H, –OCH3), 6.89–6.91 (dd, 2H, J = 8.0 Hz, benzene-H), 7.10 (s, 2H, thiopene-H), 7.13 (s, 2H, benzene-H), 7.19–7.21 (d, 2H, J = 8.0 Hz, benzene-H), 7.31–7.35 (t, 2H, J = 8.0 Hz, benzene-H); 19F NMR (376 MHz, CDCl3): δ 108.91 (4 F), 131.10 (2 F). 13C NMR (400 MHz, CDCl3): δ 15.51, 55.36, 111.45, 114.12, 118.43, 122.61, 126.77, 130.06, 134.45, 142.20, 147.83, 160.09. IR (KBr, cm-1): ν 2957, 1603, 1467, 1338, 1273, 1196, 1124, 1066, 985, 839, 775, 685 |
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 | 0.89926 (11) | 0.07792 (4) | 0.26264 (7) | 0.0506 (3) | |
S2 | 0.29932 (12) | 0.17273 (4) | −0.01266 (8) | 0.0585 (3) | |
F1 | 0.7783 (5) | 0.00387 (11) | 0.0637 (2) | 0.1167 (11) | |
F2 | 0.9579 (3) | 0.06005 (15) | 0.0379 (3) | 0.1214 (13) | |
F3 | 0.6025 (6) | 0.01301 (16) | −0.0954 (3) | 0.0869 (13) | 0.60 |
F4 | 0.8224 (8) | 0.0459 (2) | −0.1540 (3) | 0.0855 (16) | 0.60 |
F3' | 0.752 (2) | 0.0244 (6) | −0.1540 (12) | 0.200 (9)* | 0.40 |
F4' | 0.8790 (14) | 0.0800 (5) | −0.1086 (12) | 0.178 (5)* | 0.40 |
F5 | 0.4636 (5) | 0.09104 (16) | −0.1335 (3) | 0.1408 (16) | |
F6 | 0.6838 (6) | 0.13638 (14) | −0.1437 (2) | 0.1438 (16) | |
O1 | 1.3454 (4) | 0.03308 (11) | 0.5527 (2) | 0.0695 (8) | |
O2 | −0.2500 (4) | 0.26655 (13) | −0.1415 (2) | 0.0857 (10) | |
C1 | 0.9279 (4) | 0.08231 (13) | 0.4754 (3) | 0.0479 (8) | |
C2 | 0.8792 (5) | 0.10475 (18) | 0.5666 (3) | 0.0685 (11) | |
H2 | 0.7757 | 0.1220 | 0.5683 | 0.082* | |
C3 | 0.9840 (6) | 0.10134 (19) | 0.6534 (3) | 0.0752 (13) | |
H3 | 0.9493 | 0.1160 | 0.7140 | 0.090* | |
C4 | 1.1404 (5) | 0.07680 (16) | 0.6543 (3) | 0.0615 (10) | |
H4 | 1.2088 | 0.0743 | 0.7146 | 0.074* | |
C5 | 1.1920 (5) | 0.05621 (14) | 0.5638 (3) | 0.0511 (9) | |
C6 | 1.0851 (5) | 0.05833 (13) | 0.4757 (3) | 0.0485 (8) | |
H6 | 1.1198 | 0.0433 | 0.4154 | 0.058* | |
C7 | 1.4631 (6) | 0.03073 (17) | 0.6389 (3) | 0.0750 (13) | |
H7A | 1.4956 | 0.0641 | 0.6595 | 0.112* | |
H7B | 1.5631 | 0.0124 | 0.6207 | 0.112* | |
H7C | 1.4103 | 0.0141 | 0.6948 | 0.112* | |
C8 | 0.8159 (4) | 0.08570 (13) | 0.3820 (3) | 0.0481 (8) | |
C9 | 0.6445 (4) | 0.09448 (14) | 0.3716 (3) | 0.0521 (9) | |
H9 | 0.5771 | 0.0996 | 0.4279 | 0.063* | |
C10 | 0.5763 (4) | 0.09531 (13) | 0.2694 (3) | 0.0494 (9) | |
C11 | 0.3873 (4) | 0.10139 (18) | 0.2432 (3) | 0.0680 (12) | |
H11A | 0.3590 | 0.1364 | 0.2407 | 0.102* | |
H11B | 0.3228 | 0.0852 | 0.2950 | 0.102* | |
H11C | 0.3597 | 0.0864 | 0.1773 | 0.102* | |
C12 | 0.7010 (4) | 0.08738 (13) | 0.1999 (3) | 0.0443 (8) | |
C13 | 0.6891 (4) | 0.08750 (14) | 0.0883 (3) | 0.0484 (9) | |
C14 | 0.7899 (5) | 0.05067 (16) | 0.0292 (3) | 0.0653 (11) | |
C15 | 0.7188 (7) | 0.0540 (2) | −0.0801 (4) | 0.1010 (19) | |
C16 | 0.6152 (6) | 0.10156 (18) | −0.0856 (3) | 0.0740 (13) | |
C17 | 0.5974 (4) | 0.11797 (14) | 0.0225 (3) | 0.0501 (9) | |
C18 | 0.5011 (4) | 0.16275 (14) | 0.0458 (3) | 0.0481 (9) | |
C19 | 0.5451 (4) | 0.20125 (13) | 0.1120 (3) | 0.0478 (8) | |
C20 | 0.7115 (5) | 0.20591 (15) | 0.1743 (3) | 0.0642 (11) | |
H20A | 0.6990 | 0.1915 | 0.2413 | 0.096* | |
H20B | 0.7415 | 0.2407 | 0.1816 | 0.096* | |
H20C | 0.8003 | 0.1886 | 0.1400 | 0.096* | |
C21 | 0.4148 (5) | 0.23772 (14) | 0.1144 (3) | 0.0526 (9) | |
H21 | 0.4245 | 0.2663 | 0.1553 | 0.063* | |
C22 | 0.2746 (4) | 0.22804 (13) | 0.0526 (3) | 0.0492 (9) | |
C23 | 0.1162 (4) | 0.25764 (14) | 0.0387 (3) | 0.0503 (9) | |
C24 | 0.0748 (5) | 0.29342 (14) | 0.1126 (3) | 0.0575 (10) | |
H24 | 0.1481 | 0.2987 | 0.1701 | 0.069* | |
C25 | −0.0729 (5) | 0.32052 (14) | 0.1002 (3) | 0.0629 (11) | |
H25 | −0.0982 | 0.3443 | 0.1495 | 0.075* | |
C26 | −0.1865 (5) | 0.31356 (15) | 0.0161 (3) | 0.0618 (10) | |
H26 | −0.2863 | 0.3326 | 0.0085 | 0.074* | |
C27 | −0.1482 (5) | 0.27775 (16) | −0.0563 (3) | 0.0595 (10) | |
C28 | 0.0025 (5) | 0.25041 (15) | −0.0452 (3) | 0.0587 (10) | |
H28 | 0.0278 | 0.2268 | −0.0949 | 0.070* | |
C29 | −0.4146 (6) | 0.2887 (2) | −0.1516 (4) | 0.0872 (15) | |
H29A | −0.4808 | 0.2790 | −0.0944 | 0.131* | |
H29B | −0.4716 | 0.2776 | −0.2147 | 0.131* | |
H29C | −0.4033 | 0.3245 | −0.1527 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0373 (5) | 0.0669 (6) | 0.0480 (5) | 0.0091 (4) | 0.0052 (4) | 0.0036 (4) |
S2 | 0.0495 (6) | 0.0636 (6) | 0.0608 (6) | 0.0119 (4) | −0.0143 (4) | −0.0077 (5) |
F1 | 0.166 (3) | 0.0768 (19) | 0.110 (2) | 0.040 (2) | 0.036 (2) | −0.0073 (17) |
F2 | 0.0534 (16) | 0.185 (3) | 0.126 (3) | 0.0298 (19) | 0.0143 (16) | −0.057 (2) |
F3 | 0.109 (4) | 0.073 (3) | 0.076 (3) | −0.003 (3) | −0.019 (3) | −0.024 (2) |
F4 | 0.123 (4) | 0.088 (4) | 0.048 (2) | 0.042 (4) | 0.030 (2) | −0.013 (2) |
F5 | 0.119 (3) | 0.193 (4) | 0.106 (3) | 0.048 (3) | −0.044 (2) | −0.079 (3) |
F6 | 0.248 (5) | 0.121 (3) | 0.068 (2) | 0.034 (3) | 0.060 (2) | 0.0187 (19) |
O1 | 0.0672 (18) | 0.083 (2) | 0.0570 (17) | 0.0209 (15) | −0.0155 (13) | −0.0061 (14) |
O2 | 0.073 (2) | 0.116 (3) | 0.0654 (19) | 0.0408 (19) | −0.0205 (15) | −0.0089 (17) |
C1 | 0.050 (2) | 0.050 (2) | 0.045 (2) | −0.0034 (16) | 0.0097 (16) | 0.0068 (16) |
C2 | 0.061 (3) | 0.089 (3) | 0.056 (3) | 0.008 (2) | 0.014 (2) | −0.004 (2) |
C3 | 0.077 (3) | 0.103 (4) | 0.048 (2) | 0.001 (3) | 0.017 (2) | −0.010 (2) |
C4 | 0.069 (3) | 0.073 (3) | 0.043 (2) | −0.007 (2) | 0.0019 (18) | 0.0064 (19) |
C5 | 0.057 (2) | 0.047 (2) | 0.049 (2) | −0.0043 (17) | 0.0000 (17) | 0.0087 (17) |
C6 | 0.055 (2) | 0.048 (2) | 0.0429 (19) | −0.0001 (17) | 0.0055 (16) | 0.0029 (16) |
C7 | 0.083 (3) | 0.066 (3) | 0.072 (3) | 0.013 (2) | −0.032 (2) | −0.007 (2) |
C8 | 0.047 (2) | 0.049 (2) | 0.049 (2) | −0.0007 (16) | 0.0088 (16) | 0.0059 (16) |
C9 | 0.046 (2) | 0.061 (2) | 0.050 (2) | 0.0043 (17) | 0.0162 (16) | 0.0071 (17) |
C10 | 0.0416 (19) | 0.050 (2) | 0.057 (2) | 0.0035 (15) | 0.0095 (16) | 0.0112 (17) |
C11 | 0.038 (2) | 0.088 (3) | 0.078 (3) | 0.008 (2) | 0.0147 (19) | 0.020 (2) |
C12 | 0.0367 (17) | 0.048 (2) | 0.049 (2) | 0.0059 (15) | 0.0061 (14) | 0.0063 (15) |
C13 | 0.0399 (18) | 0.054 (2) | 0.052 (2) | 0.0049 (16) | 0.0035 (15) | −0.0030 (17) |
C14 | 0.062 (3) | 0.069 (3) | 0.066 (3) | 0.023 (2) | 0.009 (2) | 0.000 (2) |
C15 | 0.117 (5) | 0.127 (5) | 0.060 (3) | 0.055 (4) | 0.012 (3) | −0.007 (3) |
C16 | 0.082 (3) | 0.091 (3) | 0.048 (2) | 0.024 (3) | −0.004 (2) | −0.002 (2) |
C17 | 0.0422 (19) | 0.061 (2) | 0.047 (2) | 0.0061 (17) | −0.0014 (15) | 0.0005 (17) |
C18 | 0.0415 (19) | 0.057 (2) | 0.046 (2) | 0.0064 (16) | −0.0026 (15) | 0.0055 (17) |
C19 | 0.0426 (19) | 0.049 (2) | 0.051 (2) | −0.0032 (16) | −0.0041 (15) | 0.0093 (16) |
C20 | 0.050 (2) | 0.059 (2) | 0.082 (3) | −0.0075 (19) | −0.015 (2) | 0.007 (2) |
C21 | 0.053 (2) | 0.046 (2) | 0.058 (2) | −0.0027 (17) | −0.0050 (18) | 0.0025 (17) |
C22 | 0.046 (2) | 0.053 (2) | 0.049 (2) | 0.0029 (16) | −0.0019 (16) | 0.0067 (16) |
C23 | 0.046 (2) | 0.050 (2) | 0.055 (2) | 0.0030 (16) | −0.0003 (16) | 0.0076 (17) |
C24 | 0.053 (2) | 0.046 (2) | 0.073 (3) | −0.0024 (18) | −0.0029 (19) | −0.0013 (19) |
C25 | 0.061 (2) | 0.045 (2) | 0.083 (3) | 0.0034 (19) | 0.000 (2) | −0.010 (2) |
C26 | 0.056 (2) | 0.048 (2) | 0.082 (3) | 0.0100 (18) | 0.004 (2) | 0.011 (2) |
C27 | 0.056 (2) | 0.065 (3) | 0.057 (2) | 0.0119 (19) | −0.0049 (18) | 0.011 (2) |
C28 | 0.056 (2) | 0.067 (3) | 0.053 (2) | 0.0174 (19) | −0.0014 (18) | −0.0001 (18) |
C29 | 0.060 (3) | 0.114 (4) | 0.086 (3) | 0.029 (3) | −0.016 (2) | 0.004 (3) |
S1—C8 | 1.721 (4) | C10—C11 | 1.506 (5) |
S1—C12 | 1.732 (3) | C11—H11A | 0.9600 |
S2—C22 | 1.717 (4) | C11—H11B | 0.9600 |
S2—C18 | 1.736 (3) | C11—H11C | 0.9600 |
F1—C14 | 1.331 (5) | C12—C13 | 1.448 (5) |
F2—C14 | 1.333 (4) | C13—C17 | 1.358 (5) |
F3—C15 | 1.429 (6) | C13—C14 | 1.493 (5) |
F4—C15 | 1.302 (6) | C14—C15 | 1.502 (6) |
F3'—C15 | 1.277 (9) | C15—C16 | 1.504 (7) |
F4'—C15 | 1.492 (9) | C16—C17 | 1.483 (5) |
F5—C16 | 1.340 (5) | C17—C18 | 1.450 (5) |
F6—C16 | 1.325 (5) | C18—C19 | 1.372 (5) |
C5—O1 | 1.360 (4) | C19—C21 | 1.409 (5) |
C7—O1 | 1.415 (4) | C19—C20 | 1.503 (5) |
O2—C27 | 1.364 (5) | C20—H20A | 0.9600 |
O2—C29 | 1.415 (5) | C20—H20B | 0.9600 |
C1—C6 | 1.383 (5) | C20—H20C | 0.9600 |
C1—C2 | 1.395 (5) | C21—C22 | 1.351 (5) |
C1—C8 | 1.465 (5) | C21—H21 | 0.9300 |
C2—C3 | 1.364 (6) | C22—C23 | 1.470 (5) |
C2—H2 | 0.9300 | C23—C28 | 1.385 (5) |
C3—C4 | 1.384 (6) | C23—C24 | 1.402 (5) |
C3—H3 | 0.9300 | C24—C25 | 1.363 (5) |
C4—C5 | 1.374 (5) | C24—H24 | 0.9300 |
C4—H4 | 0.9300 | C25—C26 | 1.387 (6) |
C5—C6 | 1.385 (5) | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—C27 | 1.382 (6) |
C7—H7A | 0.9600 | C26—H26 | 0.9300 |
C7—H7B | 0.9600 | C27—C28 | 1.386 (5) |
C7—H7C | 0.9600 | C28—H28 | 0.9300 |
C8—C9 | 1.358 (5) | C29—H29A | 0.9600 |
C9—C10 | 1.407 (5) | C29—H29B | 0.9600 |
C9—H9 | 0.9300 | C29—H29C | 0.9600 |
C10—C12 | 1.373 (5) | ||
C8—S1—C12 | 92.25 (16) | F3'—C15—C14 | 126.5 (10) |
C22—S2—C18 | 92.08 (17) | F4—C15—C14 | 118.2 (5) |
C5—O1—C7 | 118.5 (3) | F3—C15—C14 | 106.9 (4) |
C27—O2—C29 | 118.4 (3) | F4'—C15—C14 | 89.1 (7) |
C6—C1—C2 | 118.2 (3) | F3'—C15—C16 | 127.7 (10) |
C6—C1—C8 | 121.7 (3) | F4—C15—C16 | 117.1 (5) |
C2—C1—C8 | 120.0 (3) | F3—C15—C16 | 107.6 (4) |
C3—C2—C1 | 119.7 (4) | F4'—C15—C16 | 92.9 (7) |
C3—C2—H2 | 120.1 | C14—C15—C16 | 105.6 (4) |
C1—C2—H2 | 120.1 | F6—C16—F5 | 104.7 (4) |
C2—C3—C4 | 122.2 (4) | F6—C16—C17 | 112.9 (4) |
C2—C3—H3 | 118.9 | F5—C16—C17 | 112.5 (4) |
C4—C3—H3 | 118.9 | F6—C16—C15 | 112.8 (4) |
C5—C4—C3 | 118.4 (4) | F5—C16—C15 | 107.8 (4) |
C5—C4—H4 | 120.8 | C17—C16—C15 | 106.1 (3) |
C3—C4—H4 | 120.8 | C13—C17—C18 | 128.6 (3) |
O1—C5—C4 | 124.5 (3) | C13—C17—C16 | 110.4 (3) |
O1—C5—C6 | 115.4 (3) | C18—C17—C16 | 120.8 (3) |
C4—C5—C6 | 120.1 (4) | C19—C18—C17 | 129.0 (3) |
C1—C6—C5 | 121.3 (3) | C19—C18—S2 | 110.8 (3) |
C1—C6—H6 | 119.3 | C17—C18—S2 | 120.2 (3) |
C5—C6—H6 | 119.3 | C18—C19—C21 | 111.8 (3) |
O1—C7—H7A | 109.5 | C18—C19—C20 | 125.7 (3) |
O1—C7—H7B | 109.5 | C21—C19—C20 | 122.5 (3) |
H7A—C7—H7B | 109.5 | C19—C20—H20A | 109.5 |
O1—C7—H7C | 109.5 | C19—C20—H20B | 109.5 |
H7A—C7—H7C | 109.5 | H20A—C20—H20B | 109.5 |
H7B—C7—H7C | 109.5 | C19—C20—H20C | 109.5 |
C9—C8—C1 | 129.8 (3) | H20A—C20—H20C | 109.5 |
C9—C8—S1 | 110.0 (3) | H20B—C20—H20C | 109.5 |
C1—C8—S1 | 120.2 (3) | C22—C21—C19 | 114.9 (3) |
C8—C9—C10 | 115.1 (3) | C22—C21—H21 | 122.6 |
C8—C9—H9 | 122.5 | C19—C21—H21 | 122.6 |
C10—C9—H9 | 122.5 | C21—C22—C23 | 128.5 (3) |
C12—C10—C9 | 111.6 (3) | C21—C22—S2 | 110.5 (3) |
C12—C10—C11 | 125.8 (3) | C23—C22—S2 | 120.9 (3) |
C9—C10—C11 | 122.5 (3) | C28—C23—C24 | 118.3 (3) |
C10—C11—H11A | 109.5 | C28—C23—C22 | 121.7 (3) |
C10—C11—H11B | 109.5 | C24—C23—C22 | 120.0 (3) |
H11A—C11—H11B | 109.5 | C25—C24—C23 | 120.0 (4) |
C10—C11—H11C | 109.5 | C25—C24—H24 | 120.0 |
H11A—C11—H11C | 109.5 | C23—C24—H24 | 120.0 |
H11B—C11—H11C | 109.5 | C24—C25—C26 | 121.9 (4) |
C10—C12—C13 | 129.9 (3) | C24—C25—H25 | 119.1 |
C10—C12—S1 | 111.0 (3) | C26—C25—H25 | 119.1 |
C13—C12—S1 | 119.0 (2) | C27—C26—C25 | 118.5 (4) |
C17—C13—C12 | 129.7 (3) | C27—C26—H26 | 120.7 |
C17—C13—C14 | 110.2 (3) | C25—C26—H26 | 120.7 |
C12—C13—C14 | 120.1 (3) | O2—C27—C26 | 124.5 (3) |
F1—C14—F2 | 103.3 (4) | O2—C27—C28 | 115.4 (4) |
F1—C14—C13 | 113.5 (3) | C26—C27—C28 | 120.1 (4) |
F2—C14—C13 | 111.8 (3) | C23—C28—C27 | 121.2 (4) |
F1—C14—C15 | 110.2 (4) | C23—C28—H28 | 119.4 |
F2—C14—C15 | 112.8 (4) | C27—C28—H28 | 119.4 |
C13—C14—C15 | 105.5 (3) | O2—C29—H29A | 109.5 |
F3'—C15—F4 | 35.9 (8) | O2—C29—H29B | 109.5 |
F3'—C15—F3 | 64.6 (9) | H29A—C29—H29B | 109.5 |
F4—C15—F3 | 100.5 (5) | O2—C29—H29C | 109.5 |
F3'—C15—F4' | 84.3 (10) | H29A—C29—H29C | 109.5 |
F4—C15—F4' | 48.6 (6) | H29B—C29—H29C | 109.5 |
F3—C15—F4' | 148.9 (8) | ||
C6—C1—C2—C3 | −1.8 (6) | F3—C15—C16—F6 | −134.0 (4) |
C8—C1—C2—C3 | 179.8 (4) | F4'—C15—C16—F6 | 22.2 (8) |
C1—C2—C3—C4 | 1.0 (7) | C14—C15—C16—F6 | 112.0 (5) |
C2—C3—C4—C5 | 1.3 (7) | F3'—C15—C16—F5 | 52.3 (13) |
C7—O1—C5—C4 | −1.5 (6) | F4—C15—C16—F5 | 93.3 (7) |
C7—O1—C5—C6 | 178.3 (3) | F3—C15—C16—F5 | −18.9 (5) |
C3—C4—C5—O1 | 176.9 (4) | F4'—C15—C16—F5 | 137.3 (7) |
C3—C4—C5—C6 | −2.8 (6) | C14—C15—C16—F5 | −132.8 (4) |
C2—C1—C6—C5 | 0.3 (5) | F3'—C15—C16—C17 | 173.0 (13) |
C8—C1—C6—C5 | 178.6 (3) | F4—C15—C16—C17 | −146.0 (6) |
O1—C5—C6—C1 | −177.7 (3) | F3—C15—C16—C17 | 101.8 (4) |
C4—C5—C6—C1 | 2.1 (5) | F4'—C15—C16—C17 | −102.0 (7) |
C6—C1—C8—C9 | 159.6 (4) | C14—C15—C16—C17 | −12.1 (5) |
C2—C1—C8—C9 | −22.2 (6) | C12—C13—C17—C18 | 8.0 (7) |
C6—C1—C8—S1 | −20.3 (5) | C14—C13—C17—C18 | −170.9 (4) |
C2—C1—C8—S1 | 157.9 (3) | C12—C13—C17—C16 | −175.9 (4) |
C12—S1—C8—C9 | 0.6 (3) | C14—C13—C17—C16 | 5.3 (5) |
C12—S1—C8—C1 | −179.5 (3) | F6—C16—C17—C13 | −119.6 (4) |
C1—C8—C9—C10 | 180.0 (3) | F5—C16—C17—C13 | 122.1 (4) |
S1—C8—C9—C10 | −0.1 (4) | C15—C16—C17—C13 | 4.5 (5) |
C8—C9—C10—C12 | −0.7 (5) | F6—C16—C17—C18 | 56.9 (5) |
C8—C9—C10—C11 | 176.2 (4) | F5—C16—C17—C18 | −61.3 (5) |
C9—C10—C12—C13 | −176.9 (4) | C15—C16—C17—C18 | −179.0 (4) |
C11—C10—C12—C13 | 6.4 (6) | C13—C17—C18—C19 | 42.4 (6) |
C9—C10—C12—S1 | 1.1 (4) | C16—C17—C18—C19 | −133.5 (4) |
C11—C10—C12—S1 | −175.6 (3) | C13—C17—C18—S2 | −136.9 (4) |
C8—S1—C12—C10 | −1.0 (3) | C16—C17—C18—S2 | 47.3 (5) |
C8—S1—C12—C13 | 177.2 (3) | C22—S2—C18—C19 | −0.5 (3) |
C10—C12—C13—C17 | 39.2 (6) | C22—S2—C18—C17 | 178.9 (3) |
S1—C12—C13—C17 | −138.7 (4) | C17—C18—C19—C21 | −179.0 (3) |
C10—C12—C13—C14 | −142.1 (4) | S2—C18—C19—C21 | 0.3 (4) |
S1—C12—C13—C14 | 40.1 (5) | C17—C18—C19—C20 | 2.0 (6) |
C17—C13—C14—F1 | −133.6 (4) | S2—C18—C19—C20 | −178.7 (3) |
C12—C13—C14—F1 | 47.4 (5) | C18—C19—C21—C22 | 0.0 (5) |
C17—C13—C14—F2 | 110.1 (4) | C20—C19—C21—C22 | 179.1 (3) |
C12—C13—C14—F2 | −68.9 (5) | C19—C21—C22—C23 | 178.8 (3) |
C17—C13—C14—C15 | −12.9 (5) | C19—C21—C22—S2 | −0.4 (4) |
C12—C13—C14—C15 | 168.1 (4) | C18—S2—C22—C21 | 0.5 (3) |
F1—C14—C15—F3' | −47.3 (13) | C18—S2—C22—C23 | −178.7 (3) |
F2—C14—C15—F3' | 67.6 (13) | C21—C22—C23—C28 | 163.1 (4) |
C13—C14—C15—F3' | −170.1 (12) | S2—C22—C23—C28 | −17.8 (5) |
F1—C14—C15—F4 | −88.9 (7) | C21—C22—C23—C24 | −18.5 (6) |
F2—C14—C15—F4 | 26.0 (8) | S2—C22—C23—C24 | 160.6 (3) |
C13—C14—C15—F4 | 148.3 (6) | C28—C23—C24—C25 | −0.9 (6) |
F1—C14—C15—F3 | 23.4 (5) | C22—C23—C24—C25 | −179.4 (3) |
F2—C14—C15—F3 | 138.2 (4) | C23—C24—C25—C26 | 0.6 (6) |
C13—C14—C15—F3 | −99.4 (4) | C24—C25—C26—C27 | 0.5 (6) |
F1—C14—C15—F4' | −129.5 (7) | C29—O2—C27—C26 | −7.4 (6) |
F2—C14—C15—F4' | −14.7 (7) | C29—O2—C27—C28 | 172.8 (4) |
C13—C14—C15—F4' | 107.7 (7) | C25—C26—C27—O2 | 178.8 (4) |
F1—C14—C15—C16 | 137.8 (4) | C25—C26—C27—C28 | −1.3 (6) |
F2—C14—C15—C16 | −107.4 (5) | C24—C23—C28—C27 | 0.1 (6) |
C13—C14—C15—C16 | 15.0 (5) | C22—C23—C28—C27 | 178.6 (3) |
F3'—C15—C16—F6 | −62.9 (14) | O2—C27—C28—C23 | −179.1 (4) |
F4—C15—C16—F6 | −21.9 (8) | C26—C27—C28—C23 | 1.0 (6) |