Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022306/ob2029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022306/ob2029Iasup2.hkl |
CCDC reference: 613791
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.040
- wR factor = 0.112
- Data-to-parameter ratio = 10.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for F6' PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for F7' PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for F8'
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F5 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F5' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT301_ALERT_3_C Main Residue Disorder ......................... 15.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact F8' .. C26 .. 2.92 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.40 Deg. F3 -C13 -F3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 39.40 Deg. F4 -C13 -F4' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.70 Deg. C14' -C13 -C14 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 19.50 Deg. F7' -C15 -F7 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 36.20 Deg. F8' -C15 -F8 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.60 Deg. C14 -C15 -C14' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 18 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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.
C27H14F10S2 | Dx = 1.575 Mg m−3 |
Mr = 592.50 | Melting point: 430.4 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.582 (2) Å | Cell parameters from 3440 reflections |
b = 11.552 (2) Å | θ = 2.6–22.6° |
c = 16.127 (3) Å | µ = 0.30 mm−1 |
β = 99.019 (3)° | T = 294 K |
V = 2499.1 (8) Å3 | Prism, colorless |
Z = 4 | 0.24 × 0.20 × 0.14 mm |
F(000) = 1192 |
Bruker SMART CCD area-detector diffractometer | 4401 independent reflections |
Radiation source: fine-focus sealed tube | 2811 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→16 |
Tmin = 0.889, Tmax = 1.000 | k = −12→13 |
12416 measured reflections | l = −19→19 |
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) = 0.112 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0475P)2 + 0.5704P] where P = (Fo2 + 2Fc2)/3 |
4401 reflections | (Δ/σ)max = 0.002 |
417 parameters | Δρmax = 0.21 e Å−3 |
18 restraints | Δρmin = −0.23 e Å−3 |
Experimental. 13C NMR (100 MHz, CDCl3) δ 14.57, 103.19, 108.47, 123.95, 126.06, 136.29, 140.00, 142.62, 162.30, 164.79. IR(KBr, cm-1) ν 540, 674, 741, 796, 874, 989, 1119, 1141, 11743, 1278, 1309, 1340, 1441, 1593, 1624, 2920, 2964. |
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. It was obvious from electron-density maps that the CF2 group at C14 was disordered corresponding with two orientations of the cyclopent-1-ene ring in a C14-envelope conformation. Initially the two disordered orientations were refined with tied occupancy parameters, but as these refined occupancy values were not significantly different from 1/2, the occupancies were then fixed at 0.5 for the final refinement cycles. 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 | 0.42439 (5) | 0.87721 (7) | 0.08251 (5) | 0.0639 (2) | |
S2 | 0.36986 (5) | 0.59328 (6) | 0.36711 (6) | 0.0693 (3) | |
F1 | 0.26356 (15) | 1.23070 (19) | −0.08961 (12) | 0.1035 (7) | |
F2 | 0.3826 (2) | 1.41200 (18) | 0.16413 (14) | 0.1208 (8) | |
F3 | 0.7269 (10) | 1.0058 (6) | 0.3143 (6) | 0.098 (3) | 0.50 |
F4 | 0.7912 (4) | 0.8648 (6) | 0.2494 (3) | 0.0988 (19) | 0.50 |
F5 | 0.8765 (6) | 0.8204 (9) | 0.3970 (7) | 0.098 (3) | 0.50 |
F6 | 0.7584 (3) | 0.8994 (3) | 0.4545 (2) | 0.0903 (12) | 0.50 |
F7 | 0.7766 (9) | 0.6336 (8) | 0.3665 (9) | 0.084 (3) | 0.50 |
F8 | 0.7112 (4) | 0.6850 (4) | 0.4700 (3) | 0.0732 (14) | 0.50 |
C14 | 0.7776 (5) | 0.8319 (8) | 0.3919 (5) | 0.063 (2) | 0.50 |
F3' | 0.7164 (9) | 0.9905 (5) | 0.3469 (6) | 0.086 (3) | 0.50 |
F4' | 0.7614 (4) | 0.9346 (5) | 0.2332 (4) | 0.0896 (17) | 0.50 |
F5' | 0.8473 (3) | 0.7538 (4) | 0.2983 (3) | 0.1133 (15) | 0.50 |
F6' | 0.8625 (7) | 0.8613 (10) | 0.4123 (7) | 0.114 (4) | 0.50 |
F7' | 0.7622 (9) | 0.6177 (9) | 0.3872 (9) | 0.104 (5) | 0.50 |
F8' | 0.7236 (5) | 0.7572 (6) | 0.4695 (3) | 0.1044 (19) | 0.50 |
C14' | 0.7970 (5) | 0.8120 (8) | 0.3514 (5) | 0.068 (2) | 0.50 |
F9 | 0.56467 (18) | 0.09962 (19) | 0.4403 (2) | 0.1372 (10) | |
F10 | 0.22996 (16) | 0.17087 (18) | 0.34050 (17) | 0.1271 (9) | |
C1 | 0.35592 (19) | 1.1227 (3) | 0.01803 (18) | 0.0638 (8) | |
H1 | 0.3485 | 1.0576 | −0.0163 | 0.077* | |
C2 | 0.3143 (2) | 1.2263 (3) | −0.01045 (19) | 0.0701 (9) | |
C3 | 0.3223 (2) | 1.3247 (3) | 0.0363 (2) | 0.0743 (9) | |
H3 | 0.2937 | 1.3941 | 0.0154 | 0.089* | |
C4 | 0.3743 (3) | 1.3164 (3) | 0.1154 (2) | 0.0739 (9) | |
C5 | 0.4173 (2) | 1.2156 (3) | 0.14823 (18) | 0.0641 (8) | |
H5 | 0.4514 | 1.2138 | 0.2029 | 0.077* | |
C6 | 0.40955 (18) | 1.1164 (2) | 0.09913 (17) | 0.0527 (7) | |
C7 | 0.45660 (18) | 1.0077 (2) | 0.13191 (16) | 0.0524 (7) | |
C8 | 0.52806 (18) | 0.9895 (2) | 0.19998 (16) | 0.0522 (7) | |
H8 | 0.5564 | 1.0491 | 0.2345 | 0.063* | |
C9 | 0.55546 (18) | 0.8715 (2) | 0.21374 (16) | 0.0482 (6) | |
C10 | 0.50569 (19) | 0.7992 (2) | 0.15386 (16) | 0.0542 (7) | |
C11 | 0.5146 (2) | 0.6710 (2) | 0.14256 (19) | 0.0703 (8) | |
H11A | 0.5813 | 0.6468 | 0.1643 | 0.105* | |
H11B | 0.5000 | 0.6524 | 0.0839 | 0.105* | |
H11C | 0.4684 | 0.6319 | 0.1722 | 0.105* | |
C12 | 0.63066 (17) | 0.8307 (2) | 0.28348 (16) | 0.0479 (6) | |
C13 | 0.7290 (2) | 0.8917 (3) | 0.30427 (18) | 0.0615 (8) | |
C15 | 0.7243 (2) | 0.7230 (3) | 0.39039 (18) | 0.0603 (7) | |
C16 | 0.62652 (18) | 0.7402 (2) | 0.33507 (15) | 0.0465 (6) | |
C17 | 0.54170 (18) | 0.6641 (2) | 0.34612 (15) | 0.0480 (6) | |
C18 | 0.4480 (2) | 0.7046 (2) | 0.35152 (18) | 0.0570 (7) | |
C19 | 0.4106 (2) | 0.8269 (3) | 0.3491 (2) | 0.0871 (11) | |
H19A | 0.4646 | 0.8781 | 0.3696 | 0.131* | |
H19B | 0.3595 | 0.8336 | 0.3838 | 0.131* | |
H19C | 0.3836 | 0.8474 | 0.2924 | 0.131* | |
C20 | 0.54882 (19) | 0.5419 (2) | 0.35543 (15) | 0.0510 (6) | |
H20 | 0.6076 | 0.5010 | 0.3543 | 0.061* | |
C21 | 0.46187 (19) | 0.4906 (2) | 0.36612 (16) | 0.0522 (7) | |
C22 | 0.4392 (2) | 0.3671 (2) | 0.37453 (16) | 0.0539 (7) | |
C23 | 0.5144 (2) | 0.2897 (3) | 0.4044 (2) | 0.0730 (9) | |
H23 | 0.5798 | 0.3148 | 0.4195 | 0.088* | |
C24 | 0.4902 (3) | 0.1750 (3) | 0.4111 (2) | 0.0822 (10) | |
C25 | 0.3961 (3) | 0.1331 (3) | 0.3903 (2) | 0.0880 (11) | |
H25 | 0.3818 | 0.0549 | 0.3955 | 0.106* | |
C26 | 0.3242 (3) | 0.2107 (3) | 0.3614 (2) | 0.0785 (9) | |
C27 | 0.3426 (2) | 0.3254 (3) | 0.35233 (18) | 0.0646 (8) | |
H27 | 0.2911 | 0.3755 | 0.3314 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0620 (5) | 0.0676 (5) | 0.0571 (4) | −0.0071 (4) | −0.0063 (4) | −0.0032 (4) |
S2 | 0.0553 (4) | 0.0573 (5) | 0.1026 (6) | 0.0009 (3) | 0.0349 (4) | 0.0031 (4) |
F1 | 0.0922 (14) | 0.1349 (18) | 0.0747 (13) | 0.0293 (12) | −0.0141 (11) | 0.0175 (12) |
F2 | 0.189 (2) | 0.0699 (13) | 0.0986 (15) | 0.0228 (14) | 0.0082 (15) | −0.0023 (12) |
F3 | 0.086 (4) | 0.075 (4) | 0.121 (7) | −0.041 (3) | −0.027 (5) | 0.027 (4) |
F4 | 0.059 (3) | 0.165 (6) | 0.076 (3) | −0.029 (3) | 0.022 (3) | 0.001 (4) |
F5 | 0.038 (3) | 0.127 (7) | 0.128 (5) | −0.011 (3) | 0.006 (3) | 0.017 (4) |
F6 | 0.125 (3) | 0.080 (3) | 0.062 (2) | −0.024 (2) | 0.001 (2) | −0.020 (2) |
F7 | 0.057 (4) | 0.069 (4) | 0.126 (6) | 0.013 (3) | 0.020 (3) | −0.027 (5) |
F8 | 0.072 (3) | 0.086 (3) | 0.056 (2) | −0.007 (3) | −0.0063 (18) | 0.007 (3) |
C14 | 0.047 (4) | 0.083 (5) | 0.056 (5) | −0.011 (4) | 0.000 (4) | −0.006 (5) |
F3' | 0.080 (4) | 0.053 (4) | 0.118 (7) | −0.010 (3) | −0.005 (4) | −0.019 (4) |
F4' | 0.055 (3) | 0.115 (5) | 0.100 (4) | −0.021 (3) | 0.016 (2) | 0.026 (3) |
F5' | 0.069 (3) | 0.122 (4) | 0.160 (4) | 0.026 (2) | 0.052 (3) | 0.015 (3) |
F6' | 0.085 (6) | 0.116 (7) | 0.119 (6) | −0.025 (4) | −0.053 (5) | 0.001 (4) |
F7' | 0.055 (5) | 0.083 (5) | 0.162 (10) | 0.007 (3) | −0.022 (6) | 0.035 (4) |
F8' | 0.103 (4) | 0.153 (6) | 0.052 (3) | 0.000 (4) | −0.005 (2) | −0.011 (4) |
C14' | 0.039 (5) | 0.083 (5) | 0.078 (6) | −0.004 (4) | −0.007 (4) | 0.001 (5) |
F9 | 0.1169 (17) | 0.0768 (15) | 0.219 (3) | 0.0251 (13) | 0.0284 (18) | 0.0456 (16) |
F10 | 0.0937 (15) | 0.0882 (15) | 0.199 (3) | −0.0390 (12) | 0.0209 (15) | −0.0328 (16) |
C1 | 0.0506 (16) | 0.080 (2) | 0.0600 (18) | 0.0015 (15) | 0.0059 (14) | 0.0020 (16) |
C2 | 0.0507 (17) | 0.098 (3) | 0.060 (2) | 0.0127 (17) | 0.0050 (15) | 0.0160 (19) |
C3 | 0.071 (2) | 0.082 (2) | 0.073 (2) | 0.0186 (18) | 0.0212 (18) | 0.019 (2) |
C4 | 0.086 (2) | 0.067 (2) | 0.069 (2) | 0.0108 (18) | 0.0164 (18) | 0.0007 (18) |
C5 | 0.0697 (19) | 0.066 (2) | 0.0552 (17) | 0.0024 (16) | 0.0059 (15) | 0.0067 (16) |
C6 | 0.0431 (14) | 0.0633 (19) | 0.0523 (16) | −0.0006 (13) | 0.0098 (13) | 0.0077 (14) |
C7 | 0.0424 (14) | 0.0629 (18) | 0.0519 (16) | −0.0053 (12) | 0.0078 (12) | 0.0025 (13) |
C8 | 0.0490 (15) | 0.0525 (17) | 0.0538 (16) | −0.0093 (12) | 0.0038 (13) | 0.0003 (13) |
C9 | 0.0432 (14) | 0.0529 (16) | 0.0477 (15) | −0.0066 (12) | 0.0051 (12) | 0.0031 (13) |
C10 | 0.0512 (15) | 0.0576 (18) | 0.0538 (16) | −0.0067 (13) | 0.0080 (13) | 0.0021 (14) |
C11 | 0.082 (2) | 0.062 (2) | 0.0650 (19) | −0.0074 (16) | 0.0051 (16) | −0.0089 (16) |
C12 | 0.0420 (14) | 0.0508 (16) | 0.0509 (15) | −0.0035 (12) | 0.0078 (12) | −0.0010 (13) |
C13 | 0.0518 (17) | 0.068 (2) | 0.0642 (19) | −0.0150 (15) | 0.0069 (15) | −0.0032 (17) |
C15 | 0.0550 (17) | 0.064 (2) | 0.0602 (19) | 0.0074 (15) | 0.0035 (14) | −0.0007 (16) |
C16 | 0.0427 (14) | 0.0489 (16) | 0.0476 (15) | 0.0014 (11) | 0.0067 (12) | −0.0053 (13) |
C17 | 0.0500 (15) | 0.0477 (16) | 0.0474 (15) | 0.0005 (12) | 0.0107 (12) | 0.0022 (12) |
C18 | 0.0557 (17) | 0.0496 (17) | 0.0702 (18) | 0.0027 (13) | 0.0236 (14) | 0.0007 (14) |
C19 | 0.082 (2) | 0.0526 (19) | 0.140 (3) | 0.0122 (16) | 0.057 (2) | 0.003 (2) |
C20 | 0.0481 (15) | 0.0495 (16) | 0.0564 (16) | 0.0054 (12) | 0.0114 (12) | 0.0025 (13) |
C21 | 0.0550 (16) | 0.0513 (17) | 0.0523 (16) | −0.0027 (13) | 0.0150 (13) | −0.0012 (13) |
C22 | 0.0610 (17) | 0.0527 (17) | 0.0519 (16) | −0.0033 (14) | 0.0208 (14) | −0.0033 (13) |
C23 | 0.067 (2) | 0.060 (2) | 0.093 (2) | 0.0005 (16) | 0.0160 (17) | 0.0110 (17) |
C24 | 0.087 (3) | 0.056 (2) | 0.108 (3) | 0.0137 (19) | 0.029 (2) | 0.0089 (19) |
C25 | 0.111 (3) | 0.0465 (19) | 0.117 (3) | −0.008 (2) | 0.050 (2) | −0.0113 (19) |
C26 | 0.079 (2) | 0.066 (2) | 0.095 (2) | −0.0179 (19) | 0.0298 (19) | −0.0237 (19) |
C27 | 0.0635 (19) | 0.0549 (18) | 0.077 (2) | −0.0060 (14) | 0.0152 (15) | −0.0056 (15) |
S1—C10 | 1.720 (3) | C6—C7 | 1.469 (4) |
S1—C7 | 1.729 (3) | C7—C8 | 1.363 (3) |
S2—C18 | 1.711 (3) | C8—C9 | 1.421 (3) |
S2—C21 | 1.725 (3) | C8—H8 | 0.9300 |
F1—C2 | 1.353 (3) | C9—C10 | 1.372 (3) |
F2—C4 | 1.350 (4) | C9—C12 | 1.473 (3) |
F3—C13 | 1.329 (7) | C10—C11 | 1.498 (4) |
F4—C13 | 1.351 (5) | C11—H11A | 0.9600 |
F5—C14 | 1.340 (8) | C11—H11B | 0.9600 |
F6—C14 | 1.334 (7) | C11—H11C | 0.9600 |
F7—C15 | 1.343 (7) | C12—C16 | 1.343 (3) |
F8—C15 | 1.394 (5) | C12—C13 | 1.501 (4) |
C14—C15 | 1.449 (9) | C15—C16 | 1.493 (4) |
C14—C13 | 1.617 (9) | C16—C17 | 1.482 (3) |
F3'—C13 | 1.358 (7) | C17—C18 | 1.371 (3) |
F4'—C13 | 1.382 (5) | C17—C20 | 1.422 (3) |
F5'—C14' | 1.355 (7) | C18—C19 | 1.500 (4) |
F6'—C14' | 1.344 (8) | C19—H19A | 0.9600 |
F7'—C15 | 1.325 (8) | C19—H19B | 0.9600 |
F8'—C15 | 1.337 (5) | C19—H19C | 0.9600 |
C14'—C13 | 1.434 (9) | C20—C21 | 1.356 (3) |
C14'—C15 | 1.619 (9) | C20—H20 | 0.9300 |
F9—C24 | 1.361 (4) | C21—C22 | 1.470 (4) |
F10—C26 | 1.352 (4) | C22—C23 | 1.386 (4) |
C1—C2 | 1.371 (4) | C22—C27 | 1.390 (4) |
C1—C6 | 1.396 (4) | C23—C24 | 1.373 (4) |
C1—H1 | 0.9300 | C23—H23 | 0.9300 |
C2—C3 | 1.360 (4) | C24—C25 | 1.360 (5) |
C3—C4 | 1.360 (4) | C25—C26 | 1.354 (5) |
C3—H3 | 0.9300 | C25—H25 | 0.9300 |
C4—C5 | 1.371 (4) | C26—C27 | 1.360 (4) |
C5—C6 | 1.388 (4) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | ||
C10—S1—C7 | 93.40 (13) | C14'—C13—C12 | 107.1 (4) |
C18—S2—C21 | 92.80 (13) | F3—C13—C14 | 109.3 (6) |
F6—C14—F5 | 108.9 (7) | F4—C13—C14 | 105.2 (4) |
F6—C14—C15 | 111.3 (5) | F3'—C13—C14 | 89.1 (5) |
F5—C14—C15 | 114.1 (7) | F4'—C13—C14 | 137.6 (4) |
F6—C14—C13 | 108.1 (6) | C14'—C13—C14 | 28.7 (3) |
F5—C14—C13 | 111.4 (8) | C12—C13—C14 | 102.8 (3) |
C15—C14—C13 | 102.9 (5) | F7'—C15—F8' | 111.7 (7) |
F6'—C14'—F5' | 109.3 (7) | F7'—C15—F7 | 19.5 (12) |
F6'—C14'—C13 | 114.4 (8) | F8'—C15—F7 | 125.8 (7) |
F5'—C14'—C13 | 109.2 (6) | F7'—C15—F8 | 81.6 (7) |
F6'—C14'—C15 | 111.1 (8) | F8'—C15—F8 | 36.2 (3) |
F5'—C14'—C15 | 109.2 (6) | F7—C15—F8 | 99.9 (7) |
C13—C14'—C15 | 103.5 (4) | F7'—C15—C14 | 127.0 (7) |
C2—C1—C6 | 119.1 (3) | F8'—C15—C14 | 78.8 (4) |
C2—C1—H1 | 120.4 | F7—C15—C14 | 112.8 (7) |
C6—C1—H1 | 120.4 | F8—C15—C14 | 113.2 (4) |
F1—C2—C3 | 118.5 (3) | F7'—C15—C16 | 114.4 (6) |
F1—C2—C1 | 118.1 (3) | F8'—C15—C16 | 113.1 (3) |
C3—C2—C1 | 123.4 (3) | F7—C15—C16 | 113.1 (6) |
C2—C3—C4 | 116.4 (3) | F8—C15—C16 | 111.2 (3) |
C2—C3—H3 | 121.8 | C14—C15—C16 | 106.8 (4) |
C4—C3—H3 | 121.8 | F7'—C15—C14' | 107.7 (7) |
F2—C4—C3 | 118.1 (3) | F8'—C15—C14' | 106.2 (4) |
F2—C4—C5 | 118.5 (3) | F7—C15—C14' | 89.7 (7) |
C3—C4—C5 | 123.3 (3) | F8—C15—C14' | 137.0 (4) |
C4—C5—C6 | 119.4 (3) | C14—C15—C14' | 28.6 (3) |
C4—C5—H5 | 120.3 | C16—C15—C14' | 102.9 (3) |
C6—C5—H5 | 120.3 | C12—C16—C17 | 130.2 (2) |
C5—C6—C1 | 118.2 (3) | C12—C16—C15 | 110.7 (2) |
C5—C6—C7 | 120.7 (2) | C17—C16—C15 | 119.0 (2) |
C1—C6—C7 | 121.0 (3) | C18—C17—C20 | 112.4 (2) |
C8—C7—C6 | 129.5 (2) | C18—C17—C16 | 123.5 (2) |
C8—C7—S1 | 109.5 (2) | C20—C17—C16 | 124.1 (2) |
C6—C7—S1 | 121.00 (19) | C17—C18—C19 | 129.3 (2) |
C7—C8—C9 | 114.2 (2) | C17—C18—S2 | 110.8 (2) |
C7—C8—H8 | 122.9 | C19—C18—S2 | 119.8 (2) |
C9—C8—H8 | 122.9 | C18—C19—H19A | 109.5 |
C10—C9—C8 | 112.7 (2) | C18—C19—H19B | 109.5 |
C10—C9—C12 | 123.3 (2) | H19A—C19—H19B | 109.5 |
C8—C9—C12 | 124.0 (2) | C18—C19—H19C | 109.5 |
C9—C10—C11 | 130.3 (2) | H19A—C19—H19C | 109.5 |
C9—C10—S1 | 110.2 (2) | H19B—C19—H19C | 109.5 |
C11—C10—S1 | 119.5 (2) | C21—C20—C17 | 113.7 (2) |
C10—C11—H11A | 109.5 | C21—C20—H20 | 123.2 |
C10—C11—H11B | 109.5 | C17—C20—H20 | 123.2 |
H11A—C11—H11B | 109.5 | C20—C21—C22 | 129.4 (2) |
C10—C11—H11C | 109.5 | C20—C21—S2 | 110.3 (2) |
H11A—C11—H11C | 109.5 | C22—C21—S2 | 120.25 (19) |
H11B—C11—H11C | 109.5 | C23—C22—C27 | 118.7 (3) |
C16—C12—C9 | 129.1 (2) | C23—C22—C21 | 120.3 (3) |
C16—C12—C13 | 110.4 (2) | C27—C22—C21 | 121.0 (3) |
C9—C12—C13 | 120.5 (2) | C24—C23—C22 | 118.6 (3) |
F3—C13—F4 | 109.6 (6) | C24—C23—H23 | 120.7 |
F3—C13—F3' | 25.4 (6) | C22—C23—H23 | 120.7 |
F4—C13—F3' | 131.8 (6) | C25—C24—F9 | 118.4 (3) |
F3—C13—F4' | 76.2 (5) | C25—C24—C23 | 123.5 (3) |
F4—C13—F4' | 39.4 (3) | F9—C24—C23 | 118.1 (3) |
F3'—C13—F4' | 101.5 (5) | C26—C25—C24 | 116.7 (3) |
F3—C13—C14' | 126.6 (7) | C26—C25—H25 | 121.7 |
F4—C13—C14' | 77.5 (4) | C24—C25—H25 | 121.7 |
F3'—C13—C14' | 113.2 (6) | F10—C26—C25 | 117.6 (3) |
F4'—C13—C14' | 114.1 (4) | F10—C26—C27 | 119.2 (3) |
F3—C13—C12 | 117.2 (6) | C25—C26—C27 | 123.2 (3) |
F4—C13—C12 | 111.8 (3) | C26—C27—C22 | 119.5 (3) |
F3'—C13—C12 | 109.2 (5) | C26—C27—H27 | 120.3 |
F4'—C13—C12 | 111.8 (3) | C22—C27—H27 | 120.3 |
C6—C1—C2—F1 | 179.3 (2) | C13—C14—C15—F7' | 115.2 (9) |
C6—C1—C2—C3 | 0.1 (4) | F6—C14—C15—F8' | −20.4 (6) |
F1—C2—C3—C4 | −179.7 (3) | F5—C14—C15—F8' | 103.3 (8) |
C1—C2—C3—C4 | −0.5 (5) | C13—C14—C15—F8' | −135.9 (5) |
C2—C3—C4—F2 | −179.0 (3) | F6—C14—C15—F7 | −144.7 (8) |
C2—C3—C4—C5 | 0.0 (5) | F5—C14—C15—F7 | −20.9 (11) |
F2—C4—C5—C6 | 179.9 (3) | C13—C14—C15—F7 | 99.8 (8) |
C3—C4—C5—C6 | 0.9 (5) | F6—C14—C15—F8 | −32.1 (7) |
C4—C5—C6—C1 | −1.3 (4) | F5—C14—C15—F8 | 91.6 (8) |
C4—C5—C6—C7 | 178.7 (3) | C13—C14—C15—F8 | −147.7 (4) |
C2—C1—C6—C5 | 0.9 (4) | F6—C14—C15—C16 | 90.5 (6) |
C2—C1—C6—C7 | −179.2 (2) | F5—C14—C15—C16 | −145.7 (7) |
C5—C6—C7—C8 | −15.8 (4) | C13—C14—C15—C16 | −25.0 (4) |
C1—C6—C7—C8 | 164.2 (3) | F6—C14—C15—C14' | 176.7 (15) |
C5—C6—C7—S1 | 164.8 (2) | F5—C14—C15—C14' | −59.6 (11) |
C1—C6—C7—S1 | −15.2 (3) | C13—C14—C15—C14' | 61.1 (9) |
C10—S1—C7—C8 | 0.6 (2) | F6'—C14'—C15—F7' | −95.9 (10) |
C10—S1—C7—C6 | −179.9 (2) | F5'—C14'—C15—F7' | 24.7 (8) |
C6—C7—C8—C9 | 179.3 (2) | C13—C14'—C15—F7' | 140.9 (7) |
S1—C7—C8—C9 | −1.3 (3) | F6'—C14'—C15—F8' | 23.9 (8) |
C7—C8—C9—C10 | 1.5 (3) | F5'—C14'—C15—F8' | 144.5 (5) |
C7—C8—C9—C12 | −179.7 (2) | C13—C14'—C15—F8' | −99.3 (5) |
C8—C9—C10—C11 | 177.3 (3) | F6'—C14'—C15—F7 | −103.5 (9) |
C12—C9—C10—C11 | −1.4 (4) | F5'—C14'—C15—F7 | 17.1 (8) |
C8—C9—C10—S1 | −1.0 (3) | C13—C14'—C15—F7 | 133.4 (7) |
C12—C9—C10—S1 | −179.74 (19) | F6'—C14'—C15—F8 | 0.8 (11) |
C7—S1—C10—C9 | 0.2 (2) | F5'—C14'—C15—F8 | 121.4 (6) |
C7—S1—C10—C11 | −178.3 (2) | C13—C14'—C15—F8 | −122.3 (6) |
C10—C9—C12—C16 | −46.3 (4) | F6'—C14'—C15—C14 | 41.3 (10) |
C8—C9—C12—C16 | 135.1 (3) | F5'—C14'—C15—C14 | 161.9 (14) |
C10—C9—C12—C13 | 132.6 (3) | C13—C14'—C15—C14 | −81.8 (11) |
C8—C9—C12—C13 | −46.0 (4) | F6'—C14'—C15—C16 | 142.9 (7) |
F6'—C14'—C13—F3 | 1.4 (12) | F5'—C14'—C15—C16 | −96.5 (5) |
F5'—C14'—C13—F3 | −121.4 (7) | C13—C14'—C15—C16 | 19.7 (5) |
C15—C14'—C13—F3 | 122.3 (7) | C9—C12—C16—C17 | −9.7 (5) |
F6'—C14'—C13—F4 | 106.6 (9) | C13—C12—C16—C17 | 171.3 (2) |
F5'—C14'—C13—F4 | −16.2 (5) | C9—C12—C16—C15 | 173.5 (2) |
C15—C14'—C13—F4 | −132.4 (5) | C13—C12—C16—C15 | −5.5 (3) |
F6'—C14'—C13—F3' | −23.7 (11) | F7'—C15—C16—C12 | −125.1 (7) |
F5'—C14'—C13—F3' | −146.5 (6) | F8'—C15—C16—C12 | 105.4 (4) |
C15—C14'—C13—F3' | 97.3 (6) | F7—C15—C16—C12 | −103.9 (7) |
F6'—C14'—C13—F4' | 91.7 (9) | F8—C15—C16—C12 | 144.6 (3) |
F5'—C14'—C13—F4' | −31.1 (7) | C14—C15—C16—C12 | 20.7 (4) |
C15—C14'—C13—F4' | −147.3 (4) | C14'—C15—C16—C12 | −8.6 (4) |
F6'—C14'—C13—C12 | −144.1 (8) | F7'—C15—C16—C17 | 57.6 (8) |
F5'—C14'—C13—C12 | 93.1 (6) | F8'—C15—C16—C17 | −71.8 (4) |
C15—C14'—C13—C12 | −23.1 (5) | F7—C15—C16—C17 | 78.9 (7) |
F6'—C14'—C13—C14 | −58.6 (11) | F8—C15—C16—C17 | −32.6 (4) |
F5'—C14'—C13—C14 | 178.6 (15) | C14—C15—C16—C17 | −156.5 (3) |
C15—C14'—C13—C14 | 62.4 (10) | C14'—C15—C16—C17 | 174.1 (3) |
C16—C12—C13—F3 | −129.8 (5) | C12—C16—C17—C18 | −44.7 (4) |
C9—C12—C13—F3 | 51.1 (6) | C15—C16—C17—C18 | 132.0 (3) |
C16—C12—C13—F4 | 102.5 (4) | C12—C16—C17—C20 | 137.8 (3) |
C9—C12—C13—F4 | −76.6 (4) | C15—C16—C17—C20 | −45.6 (3) |
C16—C12—C13—F3' | −103.4 (5) | C20—C17—C18—C19 | 176.9 (3) |
C9—C12—C13—F3' | 77.4 (5) | C16—C17—C18—C19 | −0.9 (5) |
C16—C12—C13—F4' | 145.0 (4) | C20—C17—C18—S2 | −0.4 (3) |
C9—C12—C13—F4' | −34.1 (5) | C16—C17—C18—S2 | −178.24 (19) |
C16—C12—C13—C14' | 19.4 (4) | C21—S2—C18—C17 | −0.3 (2) |
C9—C12—C13—C14' | −159.7 (4) | C21—S2—C18—C19 | −177.8 (3) |
C16—C12—C13—C14 | −9.9 (4) | C18—C17—C20—C21 | 1.1 (3) |
C9—C12—C13—C14 | 171.0 (3) | C16—C17—C20—C21 | 178.9 (2) |
F6—C14—C13—F3 | 28.8 (8) | C17—C20—C21—C22 | 177.4 (2) |
F5—C14—C13—F3 | −90.8 (9) | C17—C20—C21—S2 | −1.3 (3) |
C15—C14—C13—F3 | 146.7 (6) | C18—S2—C21—C20 | 0.9 (2) |
F6—C14—C13—F4 | 146.5 (5) | C18—S2—C21—C22 | −178.0 (2) |
F5—C14—C13—F4 | 26.9 (8) | C20—C21—C22—C23 | 25.2 (4) |
C15—C14—C13—F4 | −95.7 (5) | S2—C21—C22—C23 | −156.1 (2) |
F6—C14—C13—F3' | 13.2 (7) | C20—C21—C22—C27 | −154.3 (3) |
F5—C14—C13—F3' | −106.4 (8) | S2—C21—C22—C27 | 24.3 (3) |
C15—C14—C13—F3' | 131.0 (6) | C27—C22—C23—C24 | −0.3 (4) |
F6—C14—C13—F4' | 119.3 (6) | C21—C22—C23—C24 | −179.8 (3) |
F5—C14—C13—F4' | −0.3 (11) | C22—C23—C24—C25 | −0.2 (5) |
C15—C14—C13—F4' | −122.8 (6) | C22—C23—C24—F9 | 179.9 (3) |
F6—C14—C13—C14' | 161.4 (15) | F9—C24—C25—C26 | −180.0 (3) |
F5—C14—C13—C14' | 41.8 (10) | C23—C24—C25—C26 | 0.1 (6) |
C15—C14—C13—C14' | −80.7 (11) | C24—C25—C26—F10 | −179.8 (3) |
F6—C14—C13—C12 | −96.3 (5) | C24—C25—C26—C27 | 0.5 (5) |
F5—C14—C13—C12 | 144.1 (7) | F10—C26—C27—C22 | 179.3 (3) |
C15—C14—C13—C12 | 21.5 (5) | C25—C26—C27—C22 | −1.0 (5) |
F6—C14—C15—F7' | −129.2 (9) | C23—C22—C27—C26 | 0.9 (4) |
F5—C14—C15—F7' | −5.5 (12) | C21—C22—C27—C26 | −179.6 (3) |
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