organic compounds
In the title compound, C29H16F8O2, in spite of the symmetric substitution at the hexafluoropropane group, an unsymmetrical conformation is obtained for the fluorobenzoyl substituents. One substituent is oriented syn and the other anti to the central group.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028224/sa2011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028224/sa2011Isup2.hkl |
CCDC reference: 618319
Computing details top
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1997); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.
4-Fluorophenyl
4-{1,1,1,3,3,3-hexafluoro-2-[4-(4-fluorobenzoyl)phenyl]-2-propyl}phenyl ketone top
Crystal data top
C29H16F8O2 | F(000) = 1112 |
Mr = 548.42 | Dx = 1.507 Mg m−3 |
Monoclinic, P21/n | Melting point: 616 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.940 (2) Å | Cell parameters from 78 reflections |
b = 11.202 (5) Å | θ = 4.1–14.7° |
c = 21.710 (9) Å | µ = 0.14 mm−1 |
β = 90.68 (4)° | T = 298 K |
V = 2417.2 (16) Å3 | Prism, colourless |
Z = 4 | 0.60 × 0.16 × 0.04 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.023 |
Radiation source: fine-focus sealed tube | θmax = 25.4°, θmin = 2.1° |
Graphite monochromator | h = −1→11 |
ω scans | k = −1→13 |
5765 measured reflections | l = −26→26 |
4396 independent reflections | 3 standard reflections every 97 reflections |
2319 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.161 | w = 1/[σ2(Fo2) + (0.0533P)2 + 1.9495P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4396 reflections | Δρmax = 0.25 e Å−3 |
353 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0072 (10) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
F1 | 0.7990 (2) | 0.7538 (2) | 0.00129 (10) | 0.0803 (7) | |
F2 | 0.8197 (2) | 0.82626 (19) | 0.09195 (10) | 0.0710 (6) | |
F3 | 0.7073 (2) | 0.9208 (2) | 0.02305 (11) | 0.0811 (7) | |
F4 | 0.3989 (2) | 0.6794 (2) | 0.02094 (10) | 0.0719 (6) | |
F5 | 0.5807 (2) | 0.6205 (2) | −0.02083 (10) | 0.0774 (7) | |
F6 | 0.5136 (2) | 0.8000 (2) | −0.03372 (9) | 0.0785 (7) | |
F7 | 1.0615 (3) | −0.0324 (2) | 0.09290 (16) | 0.1132 (10) | |
F8 | 0.3581 (3) | 1.0514 (3) | 0.47961 (12) | 0.1179 (11) | |
O1 | 0.6289 (3) | 0.2649 (3) | 0.23461 (13) | 0.0861 (9) | |
O2 | 0.3038 (4) | 1.1917 (3) | 0.20095 (15) | 0.1014 (11) | |
C1 | 0.7323 (4) | 0.8114 (3) | 0.04559 (17) | 0.0592 (10) | |
C2 | 0.6038 (3) | 0.7480 (3) | 0.06619 (15) | 0.0490 (8) | |
C3 | 0.5235 (4) | 0.7118 (4) | 0.00835 (16) | 0.0594 (10) | |
C4 | 0.6338 (3) | 0.6314 (3) | 0.10121 (14) | 0.0485 (8) | |
C5 | 0.7597 (3) | 0.5785 (3) | 0.10298 (16) | 0.0556 (9) | |
H5A | 0.8323 | 0.6169 | 0.0850 | 0.067* | |
C6 | 0.7783 (4) | 0.4688 (3) | 0.13128 (16) | 0.0578 (10) | |
H6A | 0.8636 | 0.4347 | 0.1322 | 0.069* | |
C7 | 0.6724 (3) | 0.4092 (3) | 0.15815 (15) | 0.0501 (9) | |
C8 | 0.5472 (4) | 0.4630 (3) | 0.15765 (15) | 0.0543 (9) | |
H8A | 0.4749 | 0.4248 | 0.1760 | 0.065* | |
C9 | 0.5284 (3) | 0.5732 (3) | 0.13017 (15) | 0.0514 (9) | |
H9A | 0.4440 | 0.6090 | 0.1311 | 0.062* | |
C10 | 0.6918 (4) | 0.2906 (3) | 0.18851 (17) | 0.0588 (10) | |
C11 | 0.7898 (4) | 0.2057 (3) | 0.16189 (16) | 0.0585 (10) | |
C12 | 0.8238 (4) | 0.2071 (3) | 0.10018 (18) | 0.0646 (10) | |
H12A | 0.7843 | 0.2631 | 0.0740 | 0.078* | |
C13 | 0.9152 (4) | 0.1269 (4) | 0.0768 (2) | 0.0767 (12) | |
H13A | 0.9373 | 0.1277 | 0.0353 | 0.092* | |
C14 | 0.9720 (4) | 0.0468 (4) | 0.1162 (3) | 0.0789 (13) | |
C15 | 0.9400 (5) | 0.0399 (4) | 0.1768 (2) | 0.0874 (14) | |
H15A | 0.9798 | −0.0172 | 0.2023 | 0.105* | |
C16 | 0.8474 (5) | 0.1190 (4) | 0.1997 (2) | 0.0777 (12) | |
H16A | 0.8231 | 0.1144 | 0.2408 | 0.093* | |
C17 | 0.5293 (3) | 0.8381 (3) | 0.10712 (15) | 0.0518 (9) | |
C18 | 0.4264 (4) | 0.9117 (3) | 0.08632 (17) | 0.0618 (10) | |
H18A | 0.3942 | 0.9038 | 0.0461 | 0.074* | |
C19 | 0.3710 (4) | 0.9962 (3) | 0.12446 (18) | 0.0655 (11) | |
H19A | 0.3032 | 1.0458 | 0.1094 | 0.079* | |
C20 | 0.4146 (4) | 1.0087 (3) | 0.18472 (17) | 0.0590 (10) | |
C21 | 0.5185 (4) | 0.9356 (3) | 0.20530 (17) | 0.0655 (11) | |
H21A | 0.5500 | 0.9433 | 0.2456 | 0.079* | |
C22 | 0.5757 (4) | 0.8520 (3) | 0.16736 (16) | 0.0604 (10) | |
H22A | 0.6457 | 0.8045 | 0.1821 | 0.072* | |
C23 | 0.3526 (4) | 1.1021 (4) | 0.22442 (19) | 0.0674 (11) | |
C24 | 0.3530 (4) | 1.0861 (3) | 0.29236 (18) | 0.0606 (10) | |
C25 | 0.3353 (4) | 0.9752 (4) | 0.3188 (2) | 0.0667 (11) | |
H25A | 0.3231 | 0.9083 | 0.2940 | 0.080* | |
C26 | 0.3356 (4) | 0.9637 (4) | 0.3826 (2) | 0.0767 (12) | |
H26A | 0.3233 | 0.8895 | 0.4009 | 0.092* | |
C27 | 0.3545 (4) | 1.0632 (5) | 0.4175 (2) | 0.0780 (13) | |
C28 | 0.3705 (4) | 1.1732 (4) | 0.3928 (2) | 0.0791 (13) | |
H28A | 0.3829 | 1.2395 | 0.4180 | 0.095* | |
C29 | 0.3683 (4) | 1.1854 (4) | 0.3296 (2) | 0.0714 (11) | |
H29A | 0.3771 | 1.2606 | 0.3120 | 0.086* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0806 (15) | 0.0812 (16) | 0.0798 (15) | −0.0119 (13) | 0.0305 (13) | −0.0027 (13) |
F2 | 0.0599 (13) | 0.0663 (14) | 0.0865 (15) | −0.0122 (11) | −0.0056 (12) | −0.0031 (12) |
F3 | 0.0867 (16) | 0.0622 (15) | 0.0943 (17) | −0.0123 (13) | 0.0031 (13) | 0.0227 (13) |
F4 | 0.0630 (14) | 0.0862 (17) | 0.0662 (13) | −0.0133 (12) | −0.0098 (11) | 0.0045 (12) |
F5 | 0.0941 (17) | 0.0789 (16) | 0.0591 (13) | −0.0043 (13) | −0.0025 (12) | −0.0170 (12) |
F6 | 0.0963 (17) | 0.0828 (16) | 0.0560 (12) | −0.0088 (13) | −0.0099 (12) | 0.0141 (12) |
F7 | 0.0782 (17) | 0.0795 (19) | 0.182 (3) | 0.0148 (15) | 0.0153 (18) | −0.0192 (19) |
F8 | 0.112 (2) | 0.168 (3) | 0.0741 (17) | 0.024 (2) | 0.0156 (15) | 0.0095 (19) |
O1 | 0.103 (2) | 0.080 (2) | 0.0755 (19) | 0.0096 (18) | 0.0259 (17) | 0.0184 (16) |
O2 | 0.143 (3) | 0.072 (2) | 0.089 (2) | 0.046 (2) | 0.007 (2) | 0.0073 (18) |
C1 | 0.061 (2) | 0.056 (2) | 0.060 (2) | −0.007 (2) | 0.004 (2) | 0.000 (2) |
C2 | 0.050 (2) | 0.049 (2) | 0.0487 (19) | −0.0009 (17) | 0.0007 (16) | 0.0017 (16) |
C3 | 0.067 (3) | 0.061 (2) | 0.051 (2) | −0.002 (2) | −0.0028 (19) | −0.001 (2) |
C4 | 0.050 (2) | 0.052 (2) | 0.0432 (18) | −0.0049 (17) | 0.0012 (15) | −0.0053 (16) |
C5 | 0.047 (2) | 0.056 (2) | 0.064 (2) | −0.0030 (18) | 0.0058 (17) | 0.0027 (19) |
C6 | 0.049 (2) | 0.056 (2) | 0.068 (2) | 0.0024 (18) | −0.0011 (18) | 0.002 (2) |
C7 | 0.052 (2) | 0.051 (2) | 0.0474 (19) | −0.0020 (18) | −0.0006 (16) | −0.0017 (17) |
C8 | 0.052 (2) | 0.059 (2) | 0.052 (2) | −0.0030 (19) | 0.0043 (17) | 0.0020 (18) |
C9 | 0.0435 (19) | 0.056 (2) | 0.055 (2) | 0.0024 (17) | −0.0001 (16) | −0.0022 (18) |
C10 | 0.064 (2) | 0.056 (2) | 0.056 (2) | −0.002 (2) | −0.0025 (19) | 0.0014 (19) |
C11 | 0.065 (2) | 0.054 (2) | 0.056 (2) | −0.0023 (19) | −0.0055 (19) | 0.0038 (18) |
C12 | 0.073 (3) | 0.052 (2) | 0.069 (3) | 0.005 (2) | 0.000 (2) | 0.004 (2) |
C13 | 0.078 (3) | 0.067 (3) | 0.085 (3) | 0.002 (2) | 0.013 (2) | −0.004 (3) |
C14 | 0.062 (3) | 0.059 (3) | 0.116 (4) | 0.005 (2) | 0.005 (3) | −0.017 (3) |
C15 | 0.096 (3) | 0.066 (3) | 0.100 (4) | 0.019 (3) | −0.021 (3) | 0.002 (3) |
C16 | 0.100 (3) | 0.062 (3) | 0.071 (3) | 0.005 (3) | −0.010 (2) | 0.006 (2) |
C17 | 0.054 (2) | 0.051 (2) | 0.051 (2) | 0.0002 (18) | −0.0022 (16) | 0.0025 (17) |
C18 | 0.069 (2) | 0.063 (2) | 0.053 (2) | 0.007 (2) | −0.0108 (19) | 0.004 (2) |
C19 | 0.065 (2) | 0.059 (2) | 0.072 (3) | 0.015 (2) | −0.008 (2) | 0.005 (2) |
C20 | 0.064 (2) | 0.055 (2) | 0.058 (2) | 0.0064 (19) | 0.0016 (19) | 0.0028 (18) |
C21 | 0.075 (3) | 0.069 (3) | 0.052 (2) | 0.015 (2) | −0.0070 (19) | −0.007 (2) |
C22 | 0.064 (2) | 0.059 (2) | 0.058 (2) | 0.017 (2) | −0.0077 (19) | −0.0041 (19) |
C23 | 0.074 (3) | 0.053 (2) | 0.075 (3) | 0.014 (2) | 0.006 (2) | 0.002 (2) |
C24 | 0.056 (2) | 0.054 (2) | 0.071 (3) | 0.0056 (19) | 0.0160 (19) | −0.005 (2) |
C25 | 0.062 (2) | 0.059 (3) | 0.080 (3) | −0.001 (2) | 0.011 (2) | −0.002 (2) |
C26 | 0.065 (3) | 0.078 (3) | 0.088 (3) | 0.002 (2) | 0.023 (2) | 0.021 (3) |
C27 | 0.057 (3) | 0.112 (4) | 0.066 (3) | 0.009 (3) | 0.014 (2) | 0.005 (3) |
C28 | 0.075 (3) | 0.083 (3) | 0.079 (3) | −0.005 (3) | 0.020 (2) | −0.015 (3) |
C29 | 0.073 (3) | 0.062 (3) | 0.080 (3) | −0.005 (2) | 0.023 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
F1—C1 | 1.340 (4) | C12—H12A | 0.9300 |
F2—C1 | 1.332 (4) | C13—C14 | 1.359 (6) |
F3—C1 | 1.341 (4) | C13—H13A | 0.9300 |
F4—C3 | 1.323 (4) | C14—C15 | 1.359 (6) |
F5—C3 | 1.334 (4) | C15—C16 | 1.374 (6) |
F6—C3 | 1.348 (4) | C15—H15A | 0.9300 |
F7—C14 | 1.359 (5) | C16—H16A | 0.9300 |
F8—C27 | 1.355 (5) | C17—C18 | 1.385 (5) |
O1—C10 | 1.221 (4) | C17—C22 | 1.390 (5) |
O2—C23 | 1.223 (4) | C18—C19 | 1.377 (5) |
C1—C2 | 1.533 (5) | C18—H18A | 0.9300 |
C2—C3 | 1.534 (5) | C19—C20 | 1.380 (5) |
C2—C4 | 1.539 (5) | C19—H19A | 0.9300 |
C2—C17 | 1.541 (5) | C20—C21 | 1.388 (5) |
C4—C5 | 1.385 (5) | C20—C23 | 1.494 (5) |
C4—C9 | 1.390 (5) | C21—C22 | 1.374 (5) |
C5—C6 | 1.385 (5) | C21—H21A | 0.9300 |
C5—H5A | 0.9300 | C22—H22A | 0.9300 |
C6—C7 | 1.382 (5) | C23—C24 | 1.486 (5) |
C6—H6A | 0.9300 | C24—C25 | 1.381 (5) |
C7—C8 | 1.383 (5) | C24—C29 | 1.382 (5) |
C7—C10 | 1.494 (5) | C25—C26 | 1.389 (6) |
C8—C9 | 1.383 (5) | C25—H25A | 0.9300 |
C8—H8A | 0.9300 | C26—C27 | 1.360 (6) |
C9—H9A | 0.9300 | C26—H26A | 0.9300 |
C10—C11 | 1.484 (5) | C27—C28 | 1.354 (6) |
C11—C12 | 1.386 (5) | C28—C29 | 1.378 (6) |
C11—C16 | 1.391 (5) | C28—H28A | 0.9300 |
C12—C13 | 1.378 (5) | C29—H29A | 0.9300 |
F2—C1—F1 | 106.2 (3) | C14—C13—H13A | 121.0 |
F2—C1—F3 | 106.2 (3) | C12—C13—H13A | 121.0 |
F1—C1—F3 | 105.6 (3) | F7—C14—C13 | 117.8 (5) |
F2—C1—C2 | 112.1 (3) | F7—C14—C15 | 119.1 (5) |
F1—C1—C2 | 114.0 (3) | C13—C14—C15 | 123.1 (4) |
F3—C1—C2 | 112.2 (3) | C14—C15—C16 | 118.6 (4) |
C1—C2—C3 | 108.1 (3) | C14—C15—H15A | 120.7 |
C1—C2—C4 | 112.4 (3) | C16—C15—H15A | 120.7 |
C3—C2—C4 | 106.0 (3) | C15—C16—C11 | 120.7 (4) |
C1—C2—C17 | 105.8 (3) | C15—C16—H16A | 119.7 |
C3—C2—C17 | 113.4 (3) | C11—C16—H16A | 119.7 |
C4—C2—C17 | 111.3 (3) | C18—C17—C22 | 118.4 (3) |
F4—C3—F5 | 107.1 (3) | C18—C17—C2 | 124.1 (3) |
F4—C3—F6 | 106.2 (3) | C22—C17—C2 | 117.4 (3) |
F5—C3—F6 | 105.6 (3) | C19—C18—C17 | 120.8 (3) |
F4—C3—C2 | 112.5 (3) | C19—C18—H18A | 119.6 |
O1—C10—C11 | 120.9 (3) | C17—C18—H18A | 119.6 |
O1—C10—C7 | 120.4 (3) | C18—C19—C20 | 121.1 (3) |
O2—C23—C24 | 120.6 (4) | C18—C19—H19A | 119.5 |
O2—C23—C20 | 119.9 (4) | C20—C19—H19A | 119.5 |
F5—C3—C2 | 111.8 (3) | C19—C20—C21 | 118.0 (3) |
F6—C3—C2 | 113.2 (3) | C19—C20—C23 | 119.4 (3) |
C5—C4—C9 | 118.2 (3) | C21—C20—C23 | 122.6 (3) |
C5—C4—C2 | 123.1 (3) | C22—C21—C20 | 121.4 (3) |
C9—C4—C2 | 118.6 (3) | C22—C21—H21A | 119.3 |
C4—C5—C6 | 120.5 (3) | C20—C21—H21A | 119.3 |
C4—C5—H5A | 119.7 | C21—C22—C17 | 120.3 (3) |
C6—C5—H5A | 119.7 | C21—C22—H22A | 119.8 |
C7—C6—C5 | 121.2 (3) | C17—C22—H22A | 119.8 |
C7—C6—H6A | 119.4 | C24—C23—C20 | 119.5 (3) |
C5—C6—H6A | 119.4 | C25—C24—C29 | 119.6 (4) |
C6—C7—C8 | 118.4 (3) | C25—C24—C23 | 121.5 (4) |
C6—C7—C10 | 121.4 (3) | C29—C24—C23 | 118.9 (4) |
C8—C7—C10 | 120.2 (3) | C24—C25—C26 | 120.0 (4) |
C9—C8—C7 | 120.6 (3) | C24—C25—H25A | 120.0 |
C9—C8—H8A | 119.7 | C26—C25—H25A | 120.0 |
C7—C8—H8A | 119.7 | C27—C26—C25 | 118.5 (4) |
C8—C9—C4 | 121.0 (3) | C27—C26—H26A | 120.7 |
C8—C9—H9A | 119.5 | C25—C26—H26A | 120.7 |
C4—C9—H9A | 119.5 | C28—C27—F8 | 118.8 (5) |
C11—C10—C7 | 118.7 (3) | C28—C27—C26 | 122.8 (4) |
C12—C11—C16 | 118.3 (4) | F8—C27—C26 | 118.5 (5) |
C12—C11—C10 | 122.6 (3) | C27—C28—C29 | 118.9 (4) |
C16—C11—C10 | 119.1 (4) | C27—C28—H28A | 120.5 |
C13—C12—C11 | 121.2 (4) | C29—C28—H28A | 120.5 |
C13—C12—H12A | 119.4 | C28—C29—C24 | 120.2 (4) |
C11—C12—H12A | 119.4 | C28—C29—H29A | 119.9 |
C14—C13—C12 | 118.0 (4) | C24—C29—H29A | 119.9 |
C14—F7—F8—C27 | −62.2 (10) | F8—F7—C14—C13 | 114.9 (11) |
F2—C1—C2—C3 | −168.3 (3) | F8—F7—C14—C15 | −67.3 (9) |
F1—C1—C2—C3 | −47.7 (4) | C12—C13—C14—F7 | 179.7 (4) |
F3—C1—C2—C3 | 72.3 (4) | C12—C13—C14—C15 | 2.0 (7) |
F2—C1—C2—C4 | −51.7 (4) | F7—C14—C15—C16 | −178.8 (4) |
F1—C1—C2—C4 | 68.9 (4) | C13—C14—C15—C16 | −1.2 (7) |
F3—C1—C2—C4 | −171.1 (3) | C14—C15—C16—C11 | −1.3 (7) |
F2—C1—C2—C17 | 69.9 (4) | C12—C11—C16—C15 | 2.7 (6) |
F1—C1—C2—C17 | −169.4 (3) | C10—C11—C16—C15 | −179.1 (4) |
F3—C1—C2—C17 | −49.4 (4) | C1—C2—C17—C18 | 96.6 (4) |
C1—C2—C3—F4 | −166.6 (3) | C3—C2—C17—C18 | −21.7 (5) |
C4—C2—C3—F4 | 72.7 (4) | C4—C2—C17—C18 | −141.1 (3) |
C17—C2—C3—F4 | −49.6 (4) | C1—C2—C17—C22 | −78.5 (4) |
C1—C2—C3—F5 | 72.9 (4) | C3—C2—C17—C22 | 163.2 (3) |
C4—C2—C3—F5 | −47.8 (4) | C4—C2—C17—C22 | 43.8 (4) |
C17—C2—C3—F5 | −170.1 (3) | C22—C17—C18—C19 | −0.2 (6) |
C1—C2—C3—F6 | −46.2 (4) | C2—C17—C18—C19 | −175.2 (3) |
C4—C2—C3—F6 | −166.9 (3) | C17—C18—C19—C20 | −1.2 (6) |
C17—C2—C3—F6 | 70.8 (4) | C18—C19—C20—C21 | 1.7 (6) |
C1—C2—C4—C5 | −12.0 (4) | C18—C19—C20—C23 | 179.5 (4) |
C3—C2—C4—C5 | 105.9 (4) | C19—C20—C21—C22 | −0.8 (6) |
C17—C2—C4—C5 | −130.5 (3) | C23—C20—C21—C22 | −178.6 (4) |
C1—C2—C4—C9 | 171.0 (3) | C20—C21—C22—C17 | −0.6 (6) |
C3—C2—C4—C9 | −71.1 (4) | C18—C17—C22—C21 | 1.1 (6) |
C17—C2—C4—C9 | 52.5 (4) | C2—C17—C22—C21 | 176.5 (3) |
C9—C4—C5—C6 | 2.0 (5) | C19—C20—C23—O2 | −26.6 (6) |
C2—C4—C5—C6 | −175.0 (3) | C21—C20—C23—O2 | 151.2 (4) |
C4—C5—C6—C7 | 0.3 (5) | C19—C20—C23—C24 | 154.4 (4) |
C5—C6—C7—C8 | −1.7 (5) | C21—C20—C23—C24 | −27.9 (6) |
C5—C6—C7—C10 | 179.8 (3) | O2—C23—C24—C25 | 144.0 (4) |
C6—C7—C8—C9 | 0.8 (5) | C20—C23—C24—C25 | −37.0 (6) |
C10—C7—C8—C9 | 179.4 (3) | O2—C23—C24—C29 | −34.5 (6) |
C7—C8—C9—C4 | 1.5 (5) | C20—C23—C24—C29 | 144.5 (4) |
C5—C4—C9—C8 | −2.8 (5) | C29—C24—C25—C26 | −1.3 (6) |
C2—C4—C9—C8 | 174.3 (3) | C23—C24—C25—C26 | −179.7 (4) |
C6—C7—C10—O1 | 144.2 (4) | C24—C25—C26—C27 | −0.4 (6) |
C8—C7—C10—O1 | −34.4 (5) | F7—F8—C27—C28 | −142.3 (4) |
C6—C7—C10—C11 | −35.2 (5) | F7—F8—C27—C26 | 37.3 (3) |
C8—C7—C10—C11 | 146.2 (3) | C25—C26—C27—C28 | 1.2 (7) |
O1—C10—C11—C12 | 154.3 (4) | C25—C26—C27—F8 | −178.4 (3) |
C7—C10—C11—C12 | −26.2 (5) | F8—C27—C28—C29 | 179.4 (4) |
O1—C10—C11—C16 | −23.8 (6) | C26—C27—C28—C29 | −0.2 (7) |
C7—C10—C11—C16 | 155.6 (3) | C27—C28—C29—C24 | −1.5 (6) |
C16—C11—C12—C13 | −1.8 (6) | C25—C24—C29—C28 | 2.2 (6) |
C10—C11—C12—C13 | −180.0 (4) | C23—C24—C29—C28 | −179.3 (4) |
C11—C12—C13—C14 | −0.5 (6) |