Furan/phenylene co-oligomer single crystals are considered as future materials for organic optoelectronics. Here, the effects of trifluoromethyl substituents on the crystallization, structure and optical properties of furan/phenylene co-oligomer 1,4-bis{5-[4-(trifluoromethyl)phenyl]furan-2-yl}benzene are studied systematically. The solution growth methods and physical vapor transport result in the formation of three polymorphs depending on the growth method and the solvent. Single-crystal X-ray analysis reveals the crystal structures to correspond to H-, J- or mixed aggregates. All obtained crystals exhibit high photoluminescence efficiency and have optical properties which strongly depend on the crystal packing. Variable-temperature X-ray powder diffraction analysis shows the thermal transition of two forms (H- and J-aggregates) into a third one (mixed aggregate). Terminal trifluoromethyl groups induce weak intermolecular interactions which control the crystal packing and optical properties of co-oligomer single crystals.
Supporting information
CCDC references: 1842017; 1842018; 1842019
Data collection: Bruker APEX2 for (I), (III). Cell refinement: Bruker SAINT for (I), (III). Data reduction: Bruker SAINT for (I), (III). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (III). For all structures, program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2017). Molecular graphics: Bruker SHELXTL for (I), (III). Software used to prepare material for publication: Bruker SHELXTL for (I), (III).
Crystal data top
C14H8F3O | F(000) = 508 |
Mr = 249.20 | Dx = 1.517 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.238 (4) Å | Cell parameters from 1580 reflections |
b = 7.5293 (11) Å | θ = 3.2–21.9° |
c = 6.2437 (9) Å | µ = 0.13 mm−1 |
β = 92.830 (6)° | T = 296 K |
V = 1091.1 (3) Å3 | PLATE, yellow |
Z = 4 | 0.25 × 0.24 × 0.01 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 1221 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.048 |
φ and ω scans | θmax = 24.9°, θmin = 3.2° |
Absorption correction: multi-scan SADABS-2008/1 | h = −27→25 |
Tmin = 0.845, Tmax = 0.980 | k = −8→8 |
8904 measured reflections | l = −7→7 |
1882 independent reflections | |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0328P)2 + 0.1981P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1882 reflections | Δρmax = 0.13 e Å−3 |
190 parameters | Δρmin = −0.17 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F1 | 0.5303 (2) | 0.5052 (10) | 0.3208 (11) | 0.102 (2) | 0.5 |
F2 | 0.5645 (3) | 0.6943 (6) | 0.1366 (14) | 0.096 (3) | 0.5 |
F3 | 0.5702 (5) | 0.4344 (14) | 0.0320 (12) | 0.143 (5) | 0.5 |
F6 | 0.5800 (5) | 0.4985 (12) | −0.0012 (7) | 0.105 (3) | 0.5 |
F5 | 0.5505 (4) | 0.6864 (7) | 0.2005 (16) | 0.128 (4) | 0.5 |
F4 | 0.5394 (3) | 0.4079 (9) | 0.2571 (14) | 0.120 (3) | 0.5 |
O1 | 0.84207 (6) | 0.50926 (16) | 0.54655 (19) | 0.0421 (4) | |
C14 | 0.57456 (10) | 0.5333 (3) | 0.2017 (4) | 0.0576 (6) | |
C1 | 0.63154 (9) | 0.5217 (2) | 0.3237 (3) | 0.0443 (5) | |
C2 | 0.68054 (9) | 0.5853 (3) | 0.2342 (3) | 0.0464 (5) | |
H2 | 0.677753 | 0.637283 | 0.098984 | 0.056* | |
C3 | 0.73353 (9) | 0.5732 (2) | 0.3420 (3) | 0.0435 (5) | |
H3 | 0.766126 | 0.617800 | 0.280044 | 0.052* | |
C4 | 0.73829 (9) | 0.4940 (2) | 0.5443 (3) | 0.0390 (5) | |
C5 | 0.79401 (9) | 0.4746 (2) | 0.6597 (3) | 0.0411 (5) | |
C6 | 0.88974 (9) | 0.4721 (2) | 0.6791 (3) | 0.0408 (5) | |
C7 | 0.94559 (9) | 0.4885 (2) | 0.5883 (3) | 0.0398 (5) | |
C8 | 0.99465 (10) | 0.4188 (3) | 0.6949 (3) | 0.0450 (5) | |
H8 | 0.991234 | 0.363415 | 0.826734 | 0.054* | |
C9 | 0.95230 (9) | 0.5699 (2) | 0.3899 (3) | 0.0447 (5) | |
H9 | 0.920320 | 0.617093 | 0.314604 | 0.054* | |
C11 | 0.68877 (9) | 0.4310 (3) | 0.6332 (3) | 0.0475 (5) | |
H11 | 0.691296 | 0.377809 | 0.767805 | 0.057* | |
C10 | 0.63595 (10) | 0.4459 (3) | 0.5253 (3) | 0.0502 (6) | |
H10 | 0.603051 | 0.404754 | 0.588339 | 0.060* | |
C12 | 0.81087 (10) | 0.4201 (3) | 0.8589 (3) | 0.0501 (6) | |
H12 | 0.786812 | 0.389443 | 0.967698 | 0.060* | |
C13 | 0.87162 (10) | 0.4182 (3) | 0.8719 (3) | 0.0502 (6) | |
H13 | 0.894968 | 0.385892 | 0.990843 | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.049 (3) | 0.156 (6) | 0.099 (3) | −0.024 (4) | −0.001 (2) | 0.034 (4) |
F2 | 0.053 (3) | 0.082 (4) | 0.151 (6) | 0.008 (2) | −0.019 (3) | 0.056 (4) |
F3 | 0.121 (9) | 0.118 (5) | 0.181 (9) | 0.053 (5) | −0.088 (7) | −0.093 (5) |
F6 | 0.069 (3) | 0.193 (9) | 0.051 (2) | 0.008 (5) | −0.009 (2) | −0.031 (3) |
F5 | 0.082 (5) | 0.118 (6) | 0.178 (7) | 0.057 (4) | −0.051 (5) | −0.084 (5) |
F4 | 0.071 (4) | 0.139 (5) | 0.144 (7) | −0.060 (4) | −0.038 (3) | 0.062 (5) |
O1 | 0.0409 (9) | 0.0443 (7) | 0.0409 (7) | 0.0011 (6) | −0.0020 (7) | 0.0055 (6) |
C14 | 0.0490 (17) | 0.0600 (16) | 0.0636 (17) | 0.0001 (12) | 0.0010 (13) | 0.0017 (14) |
C1 | 0.0425 (14) | 0.0405 (11) | 0.0500 (12) | 0.0007 (10) | 0.0039 (10) | −0.0012 (10) |
C2 | 0.0515 (15) | 0.0447 (12) | 0.0430 (11) | −0.0003 (10) | 0.0031 (11) | 0.0063 (10) |
C3 | 0.0404 (13) | 0.0463 (11) | 0.0446 (11) | −0.0014 (9) | 0.0083 (10) | 0.0039 (10) |
C4 | 0.0438 (13) | 0.0331 (10) | 0.0404 (11) | 0.0016 (9) | 0.0055 (9) | −0.0006 (9) |
C5 | 0.0469 (14) | 0.0354 (10) | 0.0414 (11) | 0.0003 (9) | 0.0064 (10) | 0.0009 (9) |
C6 | 0.0463 (14) | 0.0333 (10) | 0.0417 (11) | 0.0005 (9) | −0.0075 (10) | 0.0019 (9) |
C7 | 0.0431 (14) | 0.0336 (10) | 0.0420 (11) | −0.0030 (9) | −0.0060 (9) | −0.0015 (9) |
C8 | 0.0506 (15) | 0.0436 (12) | 0.0399 (11) | −0.0026 (10) | −0.0070 (10) | 0.0060 (9) |
C9 | 0.0442 (15) | 0.0430 (11) | 0.0456 (12) | 0.0008 (9) | −0.0109 (10) | 0.0052 (10) |
C11 | 0.0524 (15) | 0.0489 (12) | 0.0415 (11) | −0.0023 (11) | 0.0068 (10) | 0.0085 (10) |
C10 | 0.0469 (15) | 0.0506 (13) | 0.0540 (13) | −0.0046 (10) | 0.0118 (11) | 0.0042 (11) |
C12 | 0.0573 (17) | 0.0523 (13) | 0.0411 (12) | 0.0024 (11) | 0.0053 (10) | 0.0052 (10) |
C13 | 0.0559 (16) | 0.0528 (12) | 0.0408 (12) | 0.0038 (11) | −0.0059 (11) | 0.0050 (10) |
Geometric parameters (Å, º) top
F1—F4 | 0.864 (9) | C3—C4 | 1.397 (3) |
F1—C14 | 1.316 (4) | C3—H3 | 0.9300 |
F1—F5 | 1.637 (9) | C4—C11 | 1.386 (3) |
F2—F5 | 0.531 (15) | C4—C5 | 1.458 (3) |
F2—C14 | 1.296 (4) | C5—C12 | 1.349 (3) |
F2—F6 | 1.753 (10) | C6—C13 | 1.357 (3) |
F3—F6 | 0.577 (18) | C6—C7 | 1.447 (3) |
F3—C14 | 1.295 (4) | C7—C8 | 1.394 (3) |
F3—F4 | 1.621 (10) | C7—C9 | 1.398 (3) |
F6—C14 | 1.306 (4) | C8—C9i | 1.368 (3) |
F5—C14 | 1.281 (4) | C8—H8 | 0.9300 |
F4—C14 | 1.307 (4) | C9—H9 | 0.9300 |
O1—C5 | 1.376 (2) | C11—C10 | 1.375 (3) |
O1—C6 | 1.378 (2) | C11—H11 | 0.9300 |
C14—C1 | 1.497 (3) | C10—H10 | 0.9300 |
C1—C2 | 1.379 (3) | C12—C13 | 1.410 (3) |
C1—C10 | 1.381 (3) | C12—H12 | 0.9300 |
C2—C3 | 1.377 (3) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | | |
| | | |
F4—F1—C14 | 70.2 (5) | C2—C1—C10 | 119.2 (2) |
F4—F1—F5 | 114.4 (8) | C2—C1—C14 | 120.06 (19) |
C14—F1—F5 | 50.0 (3) | C10—C1—C14 | 120.8 (2) |
F5—F2—C14 | 76.6 (7) | C3—C2—C1 | 121.04 (19) |
F5—F2—F6 | 115.1 (12) | C3—C2—H2 | 119.5 |
C14—F2—F6 | 47.9 (3) | C1—C2—H2 | 119.5 |
F6—F3—C14 | 78.2 (8) | C2—C3—C4 | 120.0 (2) |
F6—F3—F4 | 127.9 (10) | C2—C3—H3 | 120.0 |
C14—F3—F4 | 51.8 (3) | C4—C3—H3 | 120.0 |
F3—F6—C14 | 76.1 (7) | C11—C4—C3 | 118.57 (19) |
F3—F6—F2 | 115.6 (13) | C11—C4—C5 | 120.16 (18) |
C14—F6—F2 | 47.4 (3) | C3—C4—C5 | 121.26 (19) |
F2—F5—C14 | 79.7 (8) | C12—C5—O1 | 108.97 (18) |
F2—F5—F1 | 129.7 (10) | C12—C5—C4 | 134.2 (2) |
C14—F5—F1 | 51.9 (3) | O1—C5—C4 | 116.78 (16) |
F1—F4—C14 | 71.3 (4) | C13—C6—O1 | 108.54 (19) |
F1—F4—F3 | 115.0 (8) | C13—C6—C7 | 134.17 (19) |
C14—F4—F3 | 51.1 (3) | O1—C6—C7 | 117.21 (16) |
C5—O1—C6 | 107.56 (15) | C8—C7—C9 | 117.62 (19) |
F5—C14—F3 | 119.8 (6) | C8—C7—C6 | 120.62 (18) |
F5—C14—F2 | 23.8 (7) | C9—C7—C6 | 121.74 (17) |
F3—C14—F2 | 106.0 (7) | C9i—C8—C7 | 121.58 (19) |
F5—C14—F6 | 103.8 (6) | C9i—C8—H8 | 119.2 |
F3—C14—F6 | 25.7 (8) | C7—C8—H8 | 119.2 |
F2—C14—F6 | 84.7 (6) | C8i—C9—C7 | 120.80 (18) |
F5—C14—F4 | 111.9 (6) | C8i—C9—H9 | 119.6 |
F3—C14—F4 | 77.1 (6) | C7—C9—H9 | 119.6 |
F2—C14—F4 | 130.8 (5) | C10—C11—C4 | 120.96 (19) |
F6—C14—F4 | 101.8 (6) | C10—C11—H11 | 119.5 |
F5—C14—F1 | 78.2 (5) | C4—C11—H11 | 119.5 |
F3—C14—F1 | 109.7 (6) | C11—C10—C1 | 120.3 (2) |
F2—C14—F1 | 101.2 (5) | C11—C10—H10 | 119.9 |
F6—C14—F1 | 129.2 (6) | C1—C10—H10 | 119.9 |
F4—C14—F1 | 38.5 (4) | C5—C12—C13 | 107.50 (19) |
F5—C14—C1 | 115.5 (4) | C5—C12—H12 | 126.2 |
F3—C14—C1 | 114.5 (5) | C13—C12—H12 | 126.2 |
F2—C14—C1 | 110.8 (4) | C6—C13—C12 | 107.41 (18) |
F6—C14—C1 | 110.8 (5) | C6—C13—H13 | 126.3 |
F4—C14—C1 | 111.9 (4) | C12—C13—H13 | 126.3 |
F1—C14—C1 | 113.5 (4) | | |
| | | |
F4—F3—F6—C14 | 16 (2) | F1—F4—C14—F2 | −47.7 (13) |
C14—F3—F6—F2 | −26.9 (14) | F3—F4—C14—F2 | 100.1 (8) |
F4—F3—F6—F2 | −11 (3) | F1—F4—C14—F6 | −140.9 (10) |
F5—F2—F6—F3 | −3 (3) | F3—F4—C14—F6 | 6.9 (10) |
C14—F2—F6—F3 | 37 (2) | F3—F4—C14—F1 | 147.8 (12) |
F5—F2—F6—C14 | −39.7 (18) | F1—F4—C14—C1 | 100.8 (10) |
F6—F2—F5—C14 | 29.2 (11) | F3—F4—C14—C1 | −111.5 (6) |
C14—F2—F5—F1 | −14.8 (19) | F4—F1—C14—F5 | 151.1 (11) |
F6—F2—F5—F1 | 14 (3) | F4—F1—C14—F3 | 33.5 (12) |
F4—F1—F5—F2 | −11 (3) | F5—F1—C14—F3 | −117.6 (7) |
C14—F1—F5—F2 | 19 (2) | F4—F1—C14—F2 | 145.2 (10) |
F4—F1—F5—C14 | −29.9 (11) | F5—F1—C14—F2 | −5.9 (8) |
F5—F1—F4—C14 | 23.9 (8) | F4—F1—C14—F6 | 52.9 (13) |
C14—F1—F4—F3 | −27.3 (8) | F5—F1—C14—F6 | −98.3 (8) |
F5—F1—F4—F3 | −3.3 (15) | F5—F1—C14—F4 | −151.1 (11) |
F6—F3—F4—F1 | 14 (3) | F4—F1—C14—C1 | −96.0 (10) |
C14—F3—F4—F1 | 33.9 (11) | F5—F1—C14—C1 | 112.8 (5) |
F6—F3—F4—C14 | −20 (3) | F5—C14—C1—C2 | −78.0 (6) |
F2—F5—C14—F3 | −59 (2) | F3—C14—C1—C2 | 67.2 (6) |
F1—F5—C14—F3 | 106.1 (7) | F2—C14—C1—C2 | −52.7 (5) |
F1—F5—C14—F2 | 165.5 (19) | F6—C14—C1—C2 | 39.6 (5) |
F2—F5—C14—F6 | −37.6 (19) | F4—C14—C1—C2 | 152.4 (5) |
F1—F5—C14—F6 | 127.9 (6) | F1—C14—C1—C2 | −165.7 (4) |
F2—F5—C14—F4 | −146.6 (17) | F5—C14—C1—C10 | 102.6 (6) |
F1—F5—C14—F4 | 18.9 (7) | F3—C14—C1—C10 | −112.2 (7) |
F2—F5—C14—F1 | −165.5 (19) | F2—C14—C1—C10 | 128.0 (5) |
F2—F5—C14—C1 | 83.9 (18) | F6—C14—C1—C10 | −139.7 (5) |
F1—F5—C14—C1 | −110.6 (4) | F4—C14—C1—C10 | −26.9 (6) |
F6—F3—C14—F5 | 56 (2) | F1—C14—C1—C10 | 14.9 (5) |
F4—F3—C14—F5 | −108.0 (7) | C10—C1—C2—C3 | 0.5 (3) |
F6—F3—C14—F2 | 35 (2) | C14—C1—C2—C3 | −178.86 (18) |
F4—F3—C14—F2 | −129.2 (6) | C1—C2—C3—C4 | 0.6 (3) |
F4—F3—C14—F6 | −164 (2) | C2—C3—C4—C11 | −0.8 (3) |
F6—F3—C14—F4 | 164 (2) | C2—C3—C4—C5 | 178.21 (18) |
F6—F3—C14—F1 | 144 (2) | C6—O1—C5—C12 | 1.0 (2) |
F4—F3—C14—F1 | −20.7 (7) | C6—O1—C5—C4 | −176.12 (15) |
F6—F3—C14—C1 | −87 (2) | C11—C4—C5—C12 | −8.0 (3) |
F4—F3—C14—C1 | 108.4 (4) | C3—C4—C5—C12 | 173.0 (2) |
F6—F2—C14—F5 | −143.5 (19) | C11—C4—C5—O1 | 168.18 (16) |
F5—F2—C14—F3 | 129.0 (18) | C3—C4—C5—O1 | −10.8 (3) |
F6—F2—C14—F3 | −14.5 (10) | C5—O1—C6—C13 | −0.9 (2) |
F5—F2—C14—F6 | 143.5 (19) | C5—O1—C6—C7 | 176.17 (14) |
F5—F2—C14—F4 | 42 (2) | C13—C6—C7—C8 | 9.7 (3) |
F6—F2—C14—F4 | −101.0 (8) | O1—C6—C7—C8 | −166.54 (16) |
F5—F2—C14—F1 | 14.5 (19) | C13—C6—C7—C9 | −171.9 (2) |
F6—F2—C14—F1 | −129.0 (6) | O1—C6—C7—C9 | 11.9 (3) |
F5—F2—C14—C1 | −106.2 (17) | C9—C7—C8—C9i | 0.3 (3) |
F6—F2—C14—C1 | 110.3 (5) | C6—C7—C8—C9i | 178.84 (17) |
F3—F6—C14—F5 | −132 (2) | C8—C7—C9—C8i | −0.3 (3) |
F2—F6—C14—F5 | 14.3 (7) | C6—C7—C9—C8i | −178.82 (17) |
F2—F6—C14—F3 | 146 (2) | C3—C4—C11—C10 | 0.0 (3) |
F3—F6—C14—F2 | −146 (2) | C5—C4—C11—C10 | −179.07 (18) |
F3—F6—C14—F4 | −16 (2) | C4—C11—C10—C1 | 1.1 (3) |
F2—F6—C14—F4 | 130.6 (5) | C2—C1—C10—C11 | −1.3 (3) |
F3—F6—C14—F1 | −46 (2) | C14—C1—C10—C11 | 178.00 (18) |
F2—F6—C14—F1 | 100.2 (7) | O1—C5—C12—C13 | −0.7 (2) |
F3—F6—C14—C1 | 103 (2) | C4—C5—C12—C13 | 175.7 (2) |
F2—F6—C14—C1 | −110.3 (4) | O1—C6—C13—C12 | 0.5 (2) |
F1—F4—C14—F5 | −30.6 (12) | C7—C6—C13—C12 | −175.90 (19) |
F3—F4—C14—F5 | 117.2 (7) | C5—C12—C13—C6 | 0.1 (2) |
F1—F4—C14—F3 | −147.8 (12) | | |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C14H8F3O | F(000) = 508 |
Mr = 249.20 | Dx = 1.527 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.505 (1) Å | Cell parameters from 3034 reflections |
b = 6.2350 (6) Å | θ = 2.7–26.8° |
c = 16.0118 (16) Å | µ = 0.13 mm−1 |
β = 109.293 (6)° | T = 296 K |
V = 1084.08 (18) Å3 | Needle, green |
Z = 4 | 0.60 × 0.18 × 0.05 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 1436 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 3.5° |
Absorption correction: multi-scan SADABS-2008/1 | h = −13→13 |
Tmin = 0.869, Tmax = 0.928 | k = −7→7 |
8382 measured reflections | l = −18→19 |
1919 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0427P)2 + 0.2052P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1919 reflections | Δρmax = 0.14 e Å−3 |
190 parameters | Δρmin = −0.17 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F2 | 0.4411 (6) | −0.2322 (18) | 0.9116 (4) | 0.0711 (19) | 0.5 |
F1 | 0.5987 (11) | −0.2020 (14) | 1.0186 (6) | 0.0678 (19) | 0.5 |
F3 | 0.5801 (13) | −0.4747 (16) | 0.9333 (9) | 0.106 (3) | 0.5 |
F6 | 0.5530 (12) | −0.4655 (15) | 0.9205 (8) | 0.099 (3) | 0.5 |
F4 | 0.6185 (12) | −0.2315 (17) | 1.0188 (6) | 0.089 (3) | 0.5 |
F5 | 0.4456 (7) | −0.195 (2) | 0.9135 (6) | 0.105 (3) | 0.5 |
O1 | 0.83660 (9) | 0.05832 (17) | 0.66274 (7) | 0.0431 (3) | |
C14 | 0.56092 (16) | −0.2619 (3) | 0.93363 (12) | 0.0532 (4) | |
C1 | 0.62232 (14) | −0.1458 (3) | 0.87832 (10) | 0.0432 (4) | |
C2 | 0.62629 (15) | −0.2362 (3) | 0.80009 (11) | 0.0484 (4) | |
H2 | 0.588950 | −0.368101 | 0.781534 | 0.058* | |
C3 | 0.68535 (15) | −0.1313 (3) | 0.74983 (10) | 0.0470 (4) | |
H3 | 0.687811 | −0.193402 | 0.697635 | 0.056* | |
C4 | 0.74137 (13) | 0.0667 (2) | 0.77632 (10) | 0.0398 (4) | |
C5 | 0.80911 (13) | 0.1755 (2) | 0.72656 (10) | 0.0411 (4) | |
C6 | 0.90561 (14) | 0.1876 (3) | 0.62774 (10) | 0.0426 (4) | |
C7 | 0.95196 (13) | 0.0920 (2) | 0.56235 (9) | 0.0414 (4) | |
C8 | 1.03866 (14) | 0.2002 (3) | 0.53401 (10) | 0.0478 (4) | |
H8 | 1.065465 | 0.335399 | 0.556840 | 0.057* | |
C9 | 0.91490 (14) | −0.1111 (3) | 0.52687 (10) | 0.0461 (4) | |
H9 | 0.857757 | −0.187402 | 0.544729 | 0.055* | |
C11 | 0.73446 (14) | 0.1575 (3) | 0.85406 (10) | 0.0474 (4) | |
H11 | 0.770087 | 0.290804 | 0.872178 | 0.057* | |
C10 | 0.67560 (15) | 0.0526 (3) | 0.90450 (11) | 0.0483 (4) | |
H10 | 0.671735 | 0.115365 | 0.956209 | 0.058* | |
C13 | 0.91961 (15) | 0.3819 (3) | 0.66766 (11) | 0.0509 (4) | |
H13 | 0.961818 | 0.498863 | 0.655751 | 0.061* | |
C12 | 0.85810 (15) | 0.3738 (3) | 0.73079 (11) | 0.0494 (4) | |
H12 | 0.852410 | 0.484360 | 0.768248 | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F2 | 0.041 (3) | 0.118 (4) | 0.054 (2) | −0.018 (2) | 0.0137 (18) | 0.012 (2) |
F1 | 0.085 (5) | 0.076 (2) | 0.050 (3) | −0.024 (3) | 0.032 (3) | −0.010 (2) |
F3 | 0.162 (6) | 0.054 (4) | 0.155 (7) | 0.035 (4) | 0.124 (5) | 0.038 (4) |
F6 | 0.165 (7) | 0.059 (5) | 0.112 (4) | −0.035 (5) | 0.099 (4) | −0.018 (4) |
F4 | 0.073 (3) | 0.151 (7) | 0.046 (3) | 0.002 (3) | 0.026 (2) | 0.031 (3) |
F5 | 0.074 (4) | 0.123 (5) | 0.145 (5) | 0.012 (3) | 0.071 (4) | 0.008 (3) |
O1 | 0.0484 (6) | 0.0454 (6) | 0.0390 (6) | −0.0060 (5) | 0.0192 (5) | −0.0002 (5) |
C14 | 0.0562 (11) | 0.0580 (12) | 0.0527 (11) | 0.0002 (9) | 0.0279 (9) | −0.0026 (9) |
C1 | 0.0430 (8) | 0.0468 (9) | 0.0425 (9) | 0.0055 (7) | 0.0177 (7) | 0.0014 (7) |
C2 | 0.0560 (10) | 0.0457 (9) | 0.0468 (9) | −0.0081 (8) | 0.0213 (8) | −0.0056 (7) |
C3 | 0.0575 (10) | 0.0490 (9) | 0.0382 (8) | −0.0034 (8) | 0.0209 (7) | −0.0065 (7) |
C4 | 0.0404 (8) | 0.0416 (8) | 0.0368 (8) | 0.0031 (7) | 0.0122 (6) | 0.0011 (7) |
C5 | 0.0425 (8) | 0.0445 (9) | 0.0362 (8) | 0.0018 (7) | 0.0128 (7) | −0.0011 (7) |
C6 | 0.0412 (8) | 0.0482 (9) | 0.0379 (8) | −0.0056 (7) | 0.0125 (7) | 0.0072 (7) |
C7 | 0.0411 (8) | 0.0474 (9) | 0.0339 (8) | −0.0050 (7) | 0.0102 (7) | 0.0066 (7) |
C8 | 0.0534 (10) | 0.0477 (9) | 0.0437 (9) | −0.0139 (8) | 0.0181 (8) | 0.0001 (7) |
C9 | 0.0476 (9) | 0.0521 (10) | 0.0406 (9) | −0.0135 (8) | 0.0175 (7) | 0.0043 (7) |
C11 | 0.0557 (10) | 0.0419 (9) | 0.0475 (10) | −0.0024 (7) | 0.0213 (8) | −0.0073 (7) |
C10 | 0.0585 (10) | 0.0490 (9) | 0.0434 (9) | 0.0036 (8) | 0.0247 (8) | −0.0065 (7) |
C13 | 0.0545 (10) | 0.0455 (9) | 0.0527 (10) | −0.0102 (8) | 0.0176 (8) | 0.0030 (8) |
C12 | 0.0526 (9) | 0.0467 (9) | 0.0501 (10) | −0.0029 (8) | 0.0183 (8) | −0.0047 (8) |
Geometric parameters (Å, º) top
F2—C14 | 1.318 (7) | C4—C5 | 1.454 (2) |
F1—C14 | 1.337 (8) | C5—C12 | 1.351 (2) |
F3—C14 | 1.345 (10) | C6—C13 | 1.354 (2) |
F6—C14 | 1.285 (9) | C6—C7 | 1.451 (2) |
F4—C14 | 1.318 (9) | C7—C9 | 1.396 (2) |
F5—C14 | 1.325 (9) | C7—C8 | 1.398 (2) |
O1—C6 | 1.3742 (18) | C8—C9i | 1.374 (2) |
O1—C5 | 1.3753 (18) | C8—H8 | 0.9300 |
C14—C1 | 1.490 (2) | C9—H9 | 0.9300 |
C1—C10 | 1.383 (2) | C11—C10 | 1.378 (2) |
C1—C2 | 1.388 (2) | C11—H11 | 0.9300 |
C2—C3 | 1.378 (2) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C13—C12 | 1.413 (2) |
C3—C4 | 1.392 (2) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C11 | 1.393 (2) | | |
| | | |
C6—O1—C5 | 107.28 (12) | C3—C4—C11 | 118.36 (14) |
F6—C14—F4 | 107.2 (7) | C3—C4—C5 | 121.66 (14) |
F6—C14—F2 | 94.8 (8) | C11—C4—C5 | 119.96 (14) |
F4—C14—F2 | 112.3 (7) | C12—C5—O1 | 109.20 (14) |
F6—C14—F5 | 105.0 (8) | C12—C5—C4 | 133.62 (15) |
F4—C14—F5 | 109.1 (7) | O1—C5—C4 | 117.13 (13) |
F2—C14—F5 | 10.2 (10) | C13—C6—O1 | 109.09 (14) |
F6—C14—F1 | 115.1 (7) | C13—C6—C7 | 133.90 (15) |
F4—C14—F1 | 12.6 (11) | O1—C6—C7 | 116.93 (13) |
F2—C14—F1 | 101.1 (6) | C9—C7—C8 | 117.41 (15) |
F5—C14—F1 | 97.1 (7) | C9—C7—C6 | 122.07 (14) |
F6—C14—F3 | 13.6 (11) | C8—C7—C6 | 120.51 (14) |
F4—C14—F3 | 96.8 (8) | C9i—C8—C7 | 121.42 (15) |
F2—C14—F3 | 107.2 (8) | C9i—C8—H8 | 119.3 |
F5—C14—F3 | 117.5 (8) | C7—C8—H8 | 119.3 |
F1—C14—F3 | 106.3 (7) | C8i—C9—C7 | 121.17 (15) |
F6—C14—C1 | 113.9 (6) | C8i—C9—H9 | 119.4 |
F4—C14—C1 | 111.7 (5) | C7—C9—H9 | 119.4 |
F2—C14—C1 | 115.6 (4) | C10—C11—C4 | 121.00 (15) |
F5—C14—C1 | 109.6 (5) | C10—C11—H11 | 119.5 |
F1—C14—C1 | 114.2 (4) | C4—C11—H11 | 119.5 |
F3—C14—C1 | 111.5 (6) | C11—C10—C1 | 120.07 (15) |
C10—C1—C2 | 119.57 (15) | C11—C10—H10 | 120.0 |
C10—C1—C14 | 120.28 (15) | C1—C10—H10 | 120.0 |
C2—C1—C14 | 120.15 (15) | C6—C13—C12 | 107.22 (15) |
C3—C2—C1 | 120.26 (15) | C6—C13—H13 | 126.4 |
C3—C2—H2 | 119.9 | C12—C13—H13 | 126.4 |
C1—C2—H2 | 119.9 | C5—C12—C13 | 107.21 (15) |
C2—C3—C4 | 120.72 (15) | C5—C12—H12 | 126.4 |
C2—C3—H3 | 119.6 | C13—C12—H12 | 126.4 |
C4—C3—H3 | 119.6 | | |
| | | |
F6—C14—C1—C10 | −157.5 (6) | C11—C4—C5—O1 | 165.59 (13) |
F4—C14—C1—C10 | −35.9 (7) | C5—O1—C6—C13 | −0.84 (16) |
F2—C14—C1—C10 | 94.2 (5) | C5—O1—C6—C7 | 176.26 (13) |
F5—C14—C1—C10 | 85.2 (5) | C13—C6—C7—C9 | −174.99 (17) |
F1—C14—C1—C10 | −22.5 (6) | O1—C6—C7—C9 | 8.8 (2) |
F3—C14—C1—C10 | −143.0 (6) | C13—C6—C7—C8 | 6.5 (3) |
F6—C14—C1—C2 | 22.5 (7) | O1—C6—C7—C8 | −169.69 (13) |
F4—C14—C1—C2 | 144.1 (6) | C9—C7—C8—C9i | 0.4 (3) |
F2—C14—C1—C2 | −85.8 (5) | C6—C7—C8—C9i | 179.00 (15) |
F5—C14—C1—C2 | −94.8 (5) | C8—C7—C9—C8i | −0.4 (3) |
F1—C14—C1—C2 | 157.5 (6) | C6—C7—C9—C8i | −178.98 (15) |
F3—C14—C1—C2 | 37.0 (7) | C3—C4—C11—C10 | 1.1 (2) |
C10—C1—C2—C3 | 1.5 (2) | C5—C4—C11—C10 | −176.98 (14) |
C14—C1—C2—C3 | −178.58 (14) | C4—C11—C10—C1 | 0.0 (2) |
C1—C2—C3—C4 | −0.3 (2) | C2—C1—C10—C11 | −1.3 (2) |
C2—C3—C4—C11 | −1.0 (2) | C14—C1—C10—C11 | 178.69 (15) |
C2—C3—C4—C5 | 177.06 (14) | O1—C6—C13—C12 | 0.60 (18) |
C6—O1—C5—C12 | 0.76 (16) | C7—C6—C13—C12 | −175.82 (16) |
C6—O1—C5—C4 | −176.88 (12) | O1—C5—C12—C13 | −0.40 (17) |
C3—C4—C5—C12 | 170.59 (17) | C4—C5—C12—C13 | 176.71 (16) |
C11—C4—C5—C12 | −11.3 (3) | C6—C13—C12—C5 | −0.12 (18) |
C3—C4—C5—O1 | −12.5 (2) | | |
Symmetry code: (i) −x+2, −y, −z+1. |
Crystal data top
C28H16F6O2 | F(000) = 2032 |
Mr = 498.41 | Dx = 1.502 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.5435 (12) Å | Cell parameters from 4952 reflections |
b = 6.2569 (3) Å | θ = 2.3–22.7° |
c = 35.797 (2) Å | µ = 0.13 mm−1 |
β = 106.649 (3)° | T = 296 K |
V = 4408.4 (4) Å3 | Needle, green |
Z = 8 | 1.00 × 0.12 × 0.02 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3612 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.093 |
φ and ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan SADABS-2008/1 | h = −24→24 |
Tmin = 0.719, Tmax = 0.862 | k = −7→7 |
50500 measured reflections | l = −42→42 |
7760 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.3399P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
7760 reflections | Δρmax = 0.17 e Å−3 |
757 parameters | Δρmin = −0.15 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
F2 | 0.1566 (6) | −0.4279 (16) | 0.7220 (3) | 0.096 (3) | 0.5 |
F3 | 0.2076 (5) | −0.374 (2) | 0.6819 (2) | 0.099 (5) | 0.5 |
F1 | 0.1322 (6) | −0.1632 (19) | 0.6852 (5) | 0.132 (6) | 0.5 |
F5 | 0.1287 (6) | −0.317 (3) | 0.7160 (3) | 0.151 (6) | 0.5 |
F6 | 0.2039 (6) | −0.441 (2) | 0.6932 (5) | 0.196 (8) | 0.5 |
F4 | 0.1564 (7) | −0.156 (3) | 0.6747 (4) | 0.130 (6) | 0.5 |
F1' | 1.0875 (7) | 0.195 (3) | 1.1328 (5) | 0.104 (5) | 0.5 |
F2' | 1.0328 (11) | 0.211 (4) | 1.1709 (4) | 0.111 (6) | 0.5 |
F3' | 1.0235 (8) | 0.459 (3) | 1.1327 (5) | 0.129 (7) | 0.5 |
F4' | 1.0831 (8) | 0.154 (3) | 1.1443 (6) | 0.148 (8) | 0.5 |
F5' | 1.0141 (12) | 0.283 (4) | 1.1719 (6) | 0.125 (7) | 0.5 |
F6' | 1.0362 (8) | 0.437 (2) | 1.1232 (4) | 0.109 (6) | 0.5 |
F2A | 0.0079 (5) | 0.288 (3) | 0.8009 (5) | 0.124 (4) | 0.5 |
F3A | 0.0730 (7) | 0.0483 (14) | 0.7941 (5) | 0.117 (6) | 0.5 |
F1A | 0.0549 (7) | 0.308 (2) | 0.7573 (2) | 0.102 (3) | 0.5 |
F5A | 0.0261 (8) | 0.159 (4) | 0.8135 (3) | 0.150 (8) | 0.5 |
F4A | 0.0217 (7) | 0.3696 (17) | 0.7702 (5) | 0.133 (4) | 0.5 |
F6A | 0.0846 (6) | 0.105 (4) | 0.7766 (8) | 0.202 (10) | 0.5 |
O1' | 0.75369 (9) | −0.0632 (3) | 1.00652 (5) | 0.0459 (5) | |
O1 | 0.43589 (9) | 0.0604 (3) | 0.84618 (5) | 0.0499 (5) | |
O1B | 0.83778 (10) | 0.4372 (3) | 0.92245 (5) | 0.0511 (5) | |
O1A | 0.33691 (9) | 0.5692 (3) | 0.92370 (5) | 0.0466 (5) | |
C14' | 1.0270 (2) | 0.2494 (7) | 1.13639 (12) | 0.0659 (9) | |
C1' | 0.96989 (15) | 0.1340 (5) | 1.10819 (8) | 0.0495 (8) | |
C2' | 0.90668 (14) | 0.2287 (5) | 1.09538 (8) | 0.0499 (8) | |
H2' | 0.899506 | 0.362249 | 1.104884 | 0.060* | |
C3' | 0.85428 (14) | 0.1268 (5) | 1.06868 (8) | 0.0471 (7) | |
H3' | 0.811932 | 0.192206 | 1.060261 | 0.057* | |
C4' | 0.86394 (14) | −0.0735 (5) | 1.05409 (8) | 0.0437 (7) | |
C5' | 0.81039 (14) | −0.1823 (5) | 1.02478 (8) | 0.0444 (7) | |
C6' | 0.71217 (14) | −0.1906 (5) | 0.97814 (8) | 0.0462 (7) | |
C7' | 0.65115 (14) | −0.0932 (5) | 0.95295 (8) | 0.0457 (8) | |
C8' | 0.61402 (15) | −0.1987 (5) | 0.91921 (9) | 0.0530 (8) | |
H8' | 0.628376 | −0.332471 | 0.913426 | 0.064* | |
C9' | 0.55674 (14) | −0.1095 (5) | 0.89433 (8) | 0.0496 (8) | |
H9' | 0.532493 | −0.185232 | 0.872400 | 0.060* | |
C7 | 0.53445 (14) | 0.0923 (5) | 0.90144 (8) | 0.0442 (7) | |
C6 | 0.47441 (15) | 0.1899 (5) | 0.87552 (8) | 0.0474 (8) | |
C5 | 0.38002 (14) | 0.1763 (5) | 0.82620 (8) | 0.0491 (8) | |
C4 | 0.33056 (14) | 0.0648 (5) | 0.79488 (8) | 0.0497 (8) | |
C11 | 0.26693 (16) | 0.1535 (5) | 0.77766 (9) | 0.0624 (9) | |
H11 | 0.256215 | 0.286360 | 0.785946 | 0.075* | |
C10 | 0.21935 (15) | 0.0466 (6) | 0.74835 (9) | 0.0659 (9) | |
H10 | 0.177089 | 0.108196 | 0.737019 | 0.079* | |
C1 | 0.23443 (15) | −0.1511 (5) | 0.73589 (8) | 0.0532 (8) | |
C14 | 0.1821 (2) | −0.2720 (7) | 0.70584 (12) | 0.0650 (9) | |
C13 | 0.44382 (16) | 0.3814 (5) | 0.87351 (9) | 0.0586 (9) | |
H13 | 0.459453 | 0.497935 | 0.889733 | 0.070* | |
C12 | 0.38389 (16) | 0.3729 (5) | 0.84235 (9) | 0.0609 (9) | |
H12 | 0.352525 | 0.482851 | 0.834295 | 0.073* | |
C12' | 0.80341 (15) | −0.3792 (5) | 1.00886 (9) | 0.0559 (8) | |
H12' | 0.834286 | −0.491028 | 1.016110 | 0.067* | |
C13' | 0.74123 (16) | −0.3856 (5) | 0.97937 (9) | 0.0563 (8) | |
H13' | 0.723369 | −0.502123 | 0.963639 | 0.068* | |
C10' | 0.98025 (15) | −0.0672 (5) | 1.09448 (9) | 0.0556 (8) | |
H10' | 1.022454 | −0.133065 | 1.103444 | 0.067* | |
C11' | 0.92788 (15) | −0.1688 (4) | 1.06760 (8) | 0.0528 (8) | |
H11' | 0.935174 | −0.302842 | 1.058300 | 0.063* | |
C9 | 0.62855 (14) | 0.1078 (5) | 0.96047 (8) | 0.0484 (8) | |
H9 | 0.652162 | 0.181628 | 0.982786 | 0.058* | |
C8 | 0.57179 (14) | 0.1985 (5) | 0.93532 (8) | 0.0512 (8) | |
H8 | 0.557845 | 0.333215 | 0.940888 | 0.061* | |
C3 | 0.34516 (15) | −0.1331 (5) | 0.78177 (9) | 0.0570 (8) | |
H3 | 0.387560 | −0.194745 | 0.792677 | 0.068* | |
C2 | 0.29755 (14) | −0.2391 (5) | 0.75279 (9) | 0.0577 (8) | |
H2 | 0.308069 | −0.372138 | 0.744474 | 0.069* | |
C14B | 0.5713 (2) | 0.7464 (8) | 0.78711 (13) | 0.0738 (10) | |
C1B | 0.62628 (15) | 0.6310 (5) | 0.81660 (9) | 0.0564 (8) | |
C10B | 0.61485 (16) | 0.4342 (6) | 0.83077 (10) | 0.0645 (9) | |
H10B | 0.572512 | 0.369954 | 0.821223 | 0.077* | |
C11B | 0.66498 (16) | 0.3311 (5) | 0.85882 (9) | 0.0617 (9) | |
H11B | 0.656246 | 0.198309 | 0.868011 | 0.074* | |
C4B | 0.72881 (14) | 0.4246 (5) | 0.87353 (8) | 0.0469 (8) | |
C5B | 0.78112 (15) | 0.3189 (5) | 0.90387 (8) | 0.0493 (8) | |
C6B | 0.87887 (15) | 0.3094 (5) | 0.95090 (8) | 0.0494 (8) | |
C7B | 0.94029 (14) | 0.4073 (5) | 0.97537 (8) | 0.0479 (8) | |
C9B | 0.96149 (15) | 0.6107 (5) | 0.96776 (8) | 0.0525 (8) | |
H9B | 0.935986 | 0.686357 | 0.946149 | 0.063* | |
C8B | 0.98052 (15) | 0.2996 (5) | 1.00824 (9) | 0.0555 (8) | |
H8B | 0.967608 | 0.163841 | 1.013947 | 0.067* | |
F2B | 0.5819 (10) | 0.767 (4) | 0.7553 (3) | 0.149 (7) | 0.5 |
F3B | 0.5620 (8) | 0.9367 (16) | 0.8002 (3) | 0.095 (3) | 0.5 |
F1B | 0.5105 (5) | 0.6623 (19) | 0.7826 (7) | 0.136 (7) | 0.5 |
F6B | 0.5923 (6) | 0.920 (3) | 0.7726 (9) | 0.182 (8) | 0.5 |
F5B | 0.5488 (9) | 0.637 (2) | 0.7550 (4) | 0.131 (5) | 0.5 |
F4B | 0.5209 (10) | 0.787 (6) | 0.7968 (4) | 0.201 (10) | 0.5 |
C3B | 0.74049 (15) | 0.6219 (5) | 0.85872 (9) | 0.0558 (8) | |
H3B | 0.783076 | 0.685414 | 0.867638 | 0.067* | |
C2B | 0.68961 (15) | 0.7237 (5) | 0.83104 (9) | 0.0606 (9) | |
H2B | 0.697887 | 0.857112 | 0.821877 | 0.073* | |
C12B | 0.78757 (16) | 0.1208 (5) | 0.91983 (9) | 0.0608 (9) | |
H12B | 0.756827 | 0.008785 | 0.912385 | 0.073* | |
C13B | 0.84916 (17) | 0.1160 (5) | 0.94967 (9) | 0.0607 (9) | |
H13B | 0.866446 | 0.000185 | 0.965741 | 0.073* | |
C14A | 0.0646 (2) | 0.2526 (8) | 0.79493 (12) | 0.0688 (10) | |
C1A | 0.12241 (14) | 0.3700 (5) | 0.82114 (8) | 0.0496 (8) | |
C2A | 0.15966 (14) | 0.2766 (5) | 0.85543 (8) | 0.0518 (8) | |
H2A | 0.147294 | 0.142394 | 0.862241 | 0.062* | |
C3A | 0.21492 (14) | 0.3792 (5) | 0.87976 (8) | 0.0491 (8) | |
H3A | 0.239207 | 0.314324 | 0.902938 | 0.059* | |
C4A | 0.23480 (14) | 0.5793 (5) | 0.86997 (8) | 0.0444 (7) | |
C5A | 0.29430 (14) | 0.6883 (5) | 0.89440 (8) | 0.0470 (8) | |
C6A | 0.39173 (14) | 0.6962 (5) | 0.94160 (8) | 0.0441 (7) | |
C7A | 0.44596 (13) | 0.5967 (5) | 0.97145 (7) | 0.0417 (7) | |
C8A | 0.50857 (15) | 0.6983 (4) | 0.98529 (8) | 0.0481 (8) | |
H8A | 0.514856 | 0.831933 | 0.975491 | 0.058* | |
C9A | 0.43861 (14) | 0.3953 (4) | 0.98676 (8) | 0.0454 (7) | |
H9A | 0.397422 | 0.323411 | 0.977924 | 0.054* | |
C11A | 0.19665 (15) | 0.6744 (5) | 0.83537 (8) | 0.0556 (8) | |
H11A | 0.208967 | 0.808427 | 0.828429 | 0.067* | |
C10A | 0.14077 (15) | 0.5714 (5) | 0.81132 (9) | 0.0601 (9) | |
H10A | 0.115364 | 0.637138 | 0.788495 | 0.072* | |
C13A | 0.38293 (15) | 0.8912 (5) | 0.92473 (9) | 0.0547 (8) | |
H13A | 0.412182 | 1.007295 | 0.931664 | 0.066* | |
C12A | 0.32104 (15) | 0.8860 (5) | 0.89460 (9) | 0.0565 (8) | |
H12A | 0.302130 | 0.998073 | 0.877946 | 0.068* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F2 | 0.108 (9) | 0.100 (5) | 0.070 (4) | −0.055 (5) | 0.012 (5) | 0.002 (4) |
F3 | 0.079 (6) | 0.174 (11) | 0.053 (3) | −0.032 (7) | 0.032 (4) | −0.045 (4) |
F1 | 0.075 (7) | 0.093 (6) | 0.170 (14) | 0.020 (5) | −0.059 (7) | 0.008 (7) |
F5 | 0.079 (7) | 0.280 (17) | 0.103 (8) | −0.089 (8) | 0.040 (6) | −0.024 (10) |
F6 | 0.090 (9) | 0.140 (8) | 0.282 (17) | 0.044 (6) | −0.069 (9) | −0.113 (10) |
F4 | 0.105 (10) | 0.179 (10) | 0.078 (4) | −0.044 (8) | −0.022 (5) | 0.034 (4) |
F1' | 0.040 (5) | 0.153 (13) | 0.115 (6) | −0.018 (7) | 0.017 (5) | −0.023 (6) |
F2' | 0.117 (12) | 0.167 (15) | 0.041 (5) | −0.045 (9) | 0.012 (5) | −0.011 (6) |
F3' | 0.097 (6) | 0.061 (7) | 0.170 (15) | 0.009 (5) | −0.059 (8) | −0.013 (8) |
F4' | 0.080 (10) | 0.098 (6) | 0.206 (19) | 0.033 (7) | −0.055 (8) | −0.030 (10) |
F5' | 0.121 (11) | 0.176 (15) | 0.083 (6) | −0.045 (8) | 0.036 (6) | −0.057 (7) |
F6' | 0.144 (10) | 0.081 (11) | 0.078 (4) | −0.064 (8) | −0.004 (5) | 0.016 (5) |
F2A | 0.046 (4) | 0.182 (11) | 0.143 (10) | −0.022 (6) | 0.027 (6) | −0.061 (7) |
F3A | 0.086 (8) | 0.048 (4) | 0.164 (9) | 0.002 (4) | −0.050 (8) | −0.005 (5) |
F1A | 0.110 (7) | 0.128 (9) | 0.047 (3) | −0.027 (6) | −0.013 (4) | 0.002 (4) |
F5A | 0.095 (9) | 0.218 (15) | 0.108 (5) | −0.091 (10) | −0.016 (6) | 0.053 (8) |
F4A | 0.105 (8) | 0.119 (6) | 0.123 (10) | −0.008 (6) | −0.051 (6) | 0.036 (7) |
F6A | 0.115 (7) | 0.22 (2) | 0.271 (17) | −0.043 (11) | 0.061 (10) | −0.185 (16) |
O1' | 0.0443 (12) | 0.0426 (12) | 0.0505 (12) | −0.0025 (10) | 0.0131 (10) | −0.0077 (10) |
O1 | 0.0485 (12) | 0.0461 (13) | 0.0550 (13) | 0.0012 (11) | 0.0146 (11) | −0.0058 (11) |
O1B | 0.0483 (13) | 0.0475 (13) | 0.0587 (13) | 0.0010 (11) | 0.0170 (11) | 0.0069 (11) |
O1A | 0.0451 (12) | 0.0443 (12) | 0.0491 (12) | −0.0053 (10) | 0.0113 (10) | 0.0016 (10) |
C14' | 0.058 (3) | 0.072 (3) | 0.060 (3) | 0.004 (3) | 0.003 (2) | 0.003 (3) |
C1' | 0.050 (2) | 0.048 (2) | 0.0477 (18) | −0.0013 (17) | 0.0083 (16) | 0.0064 (16) |
C2' | 0.0534 (19) | 0.0449 (19) | 0.0511 (18) | 0.0039 (17) | 0.0144 (17) | −0.0018 (16) |
C3' | 0.0453 (18) | 0.048 (2) | 0.0481 (18) | 0.0084 (16) | 0.0130 (16) | 0.0026 (16) |
C4' | 0.0487 (19) | 0.043 (2) | 0.0433 (17) | 0.0006 (16) | 0.0195 (16) | 0.0085 (15) |
C5' | 0.0465 (18) | 0.039 (2) | 0.0494 (18) | 0.0016 (16) | 0.0171 (16) | −0.0020 (16) |
C6' | 0.0478 (18) | 0.045 (2) | 0.0488 (18) | −0.0127 (17) | 0.0179 (16) | −0.0101 (16) |
C7' | 0.0459 (19) | 0.046 (2) | 0.0513 (19) | −0.0120 (16) | 0.0231 (16) | −0.0099 (16) |
C8' | 0.054 (2) | 0.0455 (19) | 0.064 (2) | −0.0083 (16) | 0.0240 (18) | −0.0163 (17) |
C9' | 0.0468 (19) | 0.053 (2) | 0.0500 (19) | −0.0098 (16) | 0.0151 (16) | −0.0152 (16) |
C7 | 0.0457 (18) | 0.044 (2) | 0.0496 (18) | −0.0091 (16) | 0.0241 (16) | −0.0057 (16) |
C6 | 0.0488 (19) | 0.047 (2) | 0.0497 (19) | −0.0061 (17) | 0.0201 (16) | −0.0056 (17) |
C5 | 0.0473 (19) | 0.049 (2) | 0.0531 (19) | 0.0082 (17) | 0.0173 (17) | 0.0068 (17) |
C4 | 0.0454 (19) | 0.053 (2) | 0.0527 (19) | 0.0038 (17) | 0.0173 (17) | 0.0088 (17) |
C11 | 0.058 (2) | 0.055 (2) | 0.073 (2) | 0.0158 (18) | 0.0179 (19) | 0.0032 (19) |
C10 | 0.042 (2) | 0.081 (3) | 0.070 (2) | 0.0147 (19) | 0.0087 (18) | 0.013 (2) |
C1 | 0.0444 (19) | 0.061 (2) | 0.0522 (19) | 0.0049 (17) | 0.0097 (16) | 0.0082 (17) |
C14 | 0.056 (3) | 0.074 (3) | 0.057 (3) | 0.006 (2) | 0.002 (2) | 0.011 (2) |
C13 | 0.069 (2) | 0.050 (2) | 0.061 (2) | −0.0033 (19) | 0.025 (2) | −0.0089 (17) |
C12 | 0.071 (2) | 0.051 (2) | 0.065 (2) | 0.0131 (19) | 0.025 (2) | 0.0046 (19) |
C12' | 0.066 (2) | 0.046 (2) | 0.060 (2) | 0.0057 (18) | 0.0238 (18) | 0.0023 (17) |
C13' | 0.066 (2) | 0.041 (2) | 0.064 (2) | −0.0097 (18) | 0.0211 (19) | −0.0102 (17) |
C10' | 0.047 (2) | 0.055 (2) | 0.062 (2) | 0.0098 (17) | 0.0098 (17) | 0.0111 (17) |
C11' | 0.054 (2) | 0.0431 (19) | 0.061 (2) | 0.0100 (17) | 0.0160 (18) | 0.0023 (16) |
C9 | 0.0477 (19) | 0.046 (2) | 0.0545 (19) | −0.0111 (16) | 0.0192 (16) | −0.0126 (16) |
C8 | 0.0529 (19) | 0.0464 (19) | 0.060 (2) | −0.0066 (16) | 0.0254 (17) | −0.0145 (17) |
C3 | 0.0441 (19) | 0.055 (2) | 0.066 (2) | 0.0086 (17) | 0.0065 (17) | −0.0008 (18) |
C2 | 0.048 (2) | 0.054 (2) | 0.065 (2) | 0.0097 (17) | 0.0061 (18) | −0.0042 (18) |
C14B | 0.055 (3) | 0.094 (4) | 0.064 (3) | 0.005 (3) | 0.004 (3) | −0.013 (3) |
C1B | 0.045 (2) | 0.062 (2) | 0.059 (2) | −0.0035 (19) | 0.0114 (17) | −0.0139 (19) |
C10B | 0.043 (2) | 0.072 (3) | 0.075 (2) | −0.0136 (19) | 0.0120 (19) | −0.020 (2) |
C11B | 0.057 (2) | 0.055 (2) | 0.077 (2) | −0.0127 (18) | 0.025 (2) | −0.0055 (19) |
C4B | 0.0447 (19) | 0.047 (2) | 0.0525 (19) | −0.0034 (16) | 0.0196 (16) | −0.0059 (16) |
C5B | 0.054 (2) | 0.045 (2) | 0.055 (2) | −0.0033 (17) | 0.0260 (17) | −0.0043 (17) |
C6B | 0.0494 (19) | 0.051 (2) | 0.0517 (19) | 0.0129 (17) | 0.0214 (17) | 0.0135 (17) |
C7B | 0.0456 (19) | 0.052 (2) | 0.0503 (19) | 0.0109 (17) | 0.0199 (17) | 0.0111 (16) |
C9B | 0.049 (2) | 0.054 (2) | 0.055 (2) | 0.0089 (17) | 0.0155 (17) | 0.0139 (17) |
C8B | 0.060 (2) | 0.048 (2) | 0.063 (2) | 0.0060 (17) | 0.0241 (18) | 0.0152 (18) |
F2B | 0.129 (13) | 0.27 (2) | 0.058 (6) | 0.106 (12) | 0.049 (8) | 0.046 (10) |
F3B | 0.106 (7) | 0.074 (4) | 0.082 (5) | 0.033 (4) | −0.011 (5) | −0.001 (4) |
F1B | 0.049 (5) | 0.114 (5) | 0.209 (17) | −0.010 (5) | −0.019 (8) | 0.014 (7) |
F6B | 0.102 (7) | 0.157 (10) | 0.227 (18) | −0.033 (8) | −0.050 (9) | 0.115 (10) |
F5B | 0.097 (9) | 0.172 (9) | 0.089 (6) | 0.015 (5) | −0.028 (6) | −0.046 (6) |
F4B | 0.119 (14) | 0.41 (3) | 0.092 (7) | 0.161 (16) | 0.055 (9) | 0.057 (14) |
C3B | 0.0424 (18) | 0.056 (2) | 0.065 (2) | −0.0076 (17) | 0.0090 (17) | 0.0003 (18) |
C2B | 0.053 (2) | 0.054 (2) | 0.069 (2) | 0.0002 (18) | 0.0087 (18) | 0.0081 (18) |
C12B | 0.067 (2) | 0.053 (2) | 0.066 (2) | −0.0059 (19) | 0.025 (2) | 0.0009 (19) |
C13B | 0.073 (2) | 0.046 (2) | 0.068 (2) | 0.0045 (19) | 0.027 (2) | 0.0102 (18) |
C14A | 0.056 (3) | 0.079 (3) | 0.061 (3) | 0.003 (3) | 0.002 (2) | 0.009 (3) |
C1A | 0.0465 (18) | 0.052 (2) | 0.0472 (18) | 0.0025 (17) | 0.0087 (16) | 0.0060 (17) |
C2A | 0.0511 (19) | 0.0460 (19) | 0.0550 (19) | −0.0035 (16) | 0.0101 (17) | 0.0105 (16) |
C3A | 0.0496 (19) | 0.0449 (19) | 0.0477 (18) | 0.0037 (16) | 0.0059 (16) | 0.0101 (16) |
C4A | 0.0411 (18) | 0.045 (2) | 0.0481 (18) | 0.0052 (15) | 0.0149 (15) | 0.0024 (16) |
C5A | 0.0467 (19) | 0.048 (2) | 0.0477 (18) | 0.0022 (17) | 0.0155 (16) | 0.0044 (16) |
C6A | 0.0441 (18) | 0.043 (2) | 0.0476 (18) | −0.0105 (16) | 0.0169 (16) | −0.0111 (16) |
C7A | 0.0477 (19) | 0.0399 (18) | 0.0391 (17) | −0.0080 (15) | 0.0149 (15) | −0.0090 (14) |
C8A | 0.0540 (19) | 0.0429 (19) | 0.0475 (18) | −0.0139 (16) | 0.0147 (16) | −0.0058 (15) |
C9A | 0.0451 (18) | 0.044 (2) | 0.0474 (18) | −0.0162 (15) | 0.0145 (16) | −0.0083 (15) |
C11A | 0.059 (2) | 0.051 (2) | 0.055 (2) | 0.0020 (17) | 0.0136 (18) | 0.0158 (17) |
C10A | 0.058 (2) | 0.067 (2) | 0.050 (2) | 0.0126 (18) | 0.0074 (18) | 0.0125 (18) |
C13A | 0.056 (2) | 0.045 (2) | 0.067 (2) | −0.0091 (17) | 0.0231 (18) | −0.0019 (18) |
C12A | 0.057 (2) | 0.046 (2) | 0.070 (2) | 0.0040 (17) | 0.0236 (19) | 0.0096 (18) |
Geometric parameters (Å, º) top
F2—F5 | 0.887 (15) | C7—C6 | 1.449 (4) |
F2—C14 | 1.318 (10) | C6—C13 | 1.346 (4) |
F2—F6 | 1.61 (2) | C5—C12 | 1.352 (4) |
F3—F6 | 0.60 (2) | C5—C4 | 1.457 (4) |
F3—C14 | 1.294 (10) | C4—C3 | 1.387 (4) |
F3—F4 | 1.698 (19) | C4—C11 | 1.391 (4) |
F1—F4 | 0.70 (2) | C11—C10 | 1.384 (4) |
F1—C14 | 1.274 (11) | C10—C1 | 1.380 (4) |
F1—F5 | 1.480 (16) | C1—C2 | 1.379 (4) |
F5—C14 | 1.282 (11) | C1—C14 | 1.491 (4) |
F6—C14 | 1.283 (12) | C13—C12 | 1.406 (4) |
F4—C14 | 1.308 (13) | C12'—C13' | 1.405 (4) |
F1'—F4' | 0.51 (3) | C10'—C11' | 1.376 (4) |
F1'—C14' | 1.331 (14) | C9—C8 | 1.375 (3) |
F2'—F5' | 0.60 (4) | C3—C2 | 1.375 (4) |
F2'—C14' | 1.231 (16) | C14B—F4B | 1.210 (9) |
F2'—F4' | 1.63 (2) | C14B—F2B | 1.226 (9) |
F3'—F6' | 0.51 (3) | C14B—F5B | 1.305 (10) |
F3'—C14' | 1.317 (16) | C14B—F3B | 1.314 (8) |
F4'—C14' | 1.255 (15) | C14B—F1B | 1.322 (11) |
F5'—C14' | 1.388 (18) | C14B—F6B | 1.329 (10) |
F6'—C14' | 1.297 (14) | C14B—C1B | 1.493 (4) |
F2A—F5A | 0.949 (12) | C1B—C10B | 1.377 (4) |
F2A—C14A | 1.264 (9) | C1B—C2B | 1.383 (4) |
F2A—F4A | 1.313 (12) | C10B—C11B | 1.376 (4) |
F3A—F6A | 0.81 (2) | C11B—C4B | 1.394 (4) |
F3A—C14A | 1.292 (11) | C4B—C3B | 1.391 (4) |
F3A—F5A | 1.508 (16) | C4B—C5B | 1.450 (4) |
F1A—F4A | 1.008 (12) | C5B—C12B | 1.355 (4) |
F1A—C14A | 1.350 (9) | C6B—C13B | 1.350 (4) |
F1A—F6A | 1.49 (2) | C6B—C7B | 1.450 (4) |
F5A—C14A | 1.308 (10) | C7B—C9B | 1.397 (4) |
F4A—C14A | 1.284 (8) | C7B—C8B | 1.401 (4) |
F6A—C14A | 1.268 (13) | C9B—C8Bi | 1.373 (4) |
O1'—C6' | 1.378 (3) | F2B—F5B | 1.059 (16) |
O1'—C5' | 1.380 (3) | F2B—F6B | 1.127 (13) |
O1—C5 | 1.373 (3) | F3B—F4B | 1.24 (3) |
O1—C6 | 1.382 (3) | F3B—F6B | 1.32 (2) |
O1B—C6B | 1.377 (3) | F1B—F4B | 0.92 (3) |
O1B—C5B | 1.379 (3) | F1B—F5B | 1.439 (15) |
O1A—C5A | 1.377 (3) | C3B—C2B | 1.374 (4) |
O1A—C6A | 1.377 (3) | C12B—C13B | 1.403 (4) |
C14'—C1' | 1.496 (4) | C14A—C1A | 1.481 (4) |
C1'—C2' | 1.381 (3) | C1A—C2A | 1.377 (3) |
C1'—C10' | 1.390 (4) | C1A—C10A | 1.389 (4) |
C2'—C3' | 1.374 (3) | C2A—C3A | 1.376 (4) |
C3'—C4' | 1.394 (4) | C3A—C4A | 1.393 (4) |
C4'—C11' | 1.397 (3) | C4A—C11A | 1.395 (4) |
C4'—C5' | 1.454 (4) | C4A—C5A | 1.453 (4) |
C5'—C12' | 1.348 (4) | C5A—C12A | 1.353 (4) |
C6'—C13' | 1.354 (4) | C6A—C13A | 1.350 (4) |
C6'—C7' | 1.452 (4) | C6A—C7A | 1.445 (4) |
C7'—C9 | 1.393 (3) | C7A—C8A | 1.392 (3) |
C7'—C8' | 1.396 (4) | C7A—C9A | 1.400 (4) |
C8'—C9' | 1.374 (4) | C8A—C9Aii | 1.378 (3) |
C9'—C7 | 1.391 (4) | C11A—C10A | 1.381 (4) |
C7—C8 | 1.402 (4) | C13A—C12A | 1.413 (4) |
| | | |
F5—F2—C14 | 67.9 (11) | F1—C14—C1 | 116.2 (7) |
F5—F2—F6 | 110.6 (17) | F5—C14—C1 | 113.9 (6) |
C14—F2—F6 | 50.8 (7) | F6—C14—C1 | 114.9 (6) |
F6—F3—C14 | 75.5 (18) | F3—C14—C1 | 112.4 (5) |
F6—F3—F4 | 118 (2) | F4—C14—C1 | 111.3 (8) |
C14—F3—F4 | 49.6 (6) | F2—C14—C1 | 110.7 (6) |
F4—F1—C14 | 76.8 (18) | C6—C13—C12 | 107.3 (3) |
F4—F1—F5 | 129 (2) | C5—C12—C13 | 107.7 (3) |
C14—F1—F5 | 54.9 (6) | C5'—C12'—C13' | 107.9 (3) |
F2—F5—C14 | 72.2 (13) | C6'—C13'—C12' | 107.2 (3) |
F2—F5—F1 | 121.5 (18) | C11'—C10'—C1' | 119.8 (3) |
C14—F5—F1 | 54.4 (6) | C10'—C11'—C4' | 120.9 (3) |
F3—F6—C14 | 77 (2) | C8—C9—C7' | 120.9 (3) |
F3—F6—F2 | 127 (2) | C9—C8—C7 | 121.4 (3) |
C14—F6—F2 | 52.7 (6) | C2—C3—C4 | 120.6 (3) |
F1—F4—C14 | 71.5 (18) | C3—C2—C1 | 121.0 (3) |
F1—F4—F3 | 112 (2) | F4B—C14B—F2B | 129.7 (7) |
C14—F4—F3 | 48.9 (6) | F4B—C14B—F5B | 104.4 (11) |
F4'—F1'—C14' | 70 (3) | F2B—C14B—F5B | 49.3 (8) |
F5'—F2'—C14' | 92 (4) | F4B—C14B—F3B | 58.8 (14) |
F5'—F2'—F4' | 136 (5) | F2B—C14B—F3B | 108.7 (9) |
C14'—F2'—F4' | 49.5 (9) | F5B—C14B—F3B | 137.8 (7) |
F6'—F3'—C14' | 77 (3) | F4B—C14B—F1B | 42.5 (13) |
F1'—F4'—C14' | 87 (4) | F2B—C14B—F1B | 109.9 (9) |
F1'—F4'—F2' | 130 (4) | F5B—C14B—F1B | 66.4 (6) |
C14'—F4'—F2' | 48.3 (9) | F3B—C14B—F1B | 100.1 (7) |
F2'—F5'—C14' | 62 (3) | F4B—C14B—F6B | 109.9 (11) |
F3'—F6'—C14' | 81 (3) | F2B—C14B—F6B | 52.2 (7) |
F5A—F2A—C14A | 70.8 (10) | F5B—C14B—F6B | 99.1 (9) |
F5A—F2A—F4A | 125.2 (14) | F3B—C14B—F6B | 59.7 (10) |
C14A—F2A—F4A | 59.7 (5) | F1B—C14B—F6B | 132.8 (8) |
F6A—F3A—C14A | 69.9 (14) | F4B—C14B—C1B | 115.8 (6) |
F6A—F3A—F5A | 121.4 (18) | F2B—C14B—C1B | 114.1 (5) |
C14A—F3A—F5A | 55.0 (5) | F5B—C14B—C1B | 112.0 (6) |
F4A—F1A—C14A | 64.1 (8) | F3B—C14B—C1B | 110.1 (5) |
F4A—F1A—F6A | 110.8 (13) | F1B—C14B—C1B | 113.0 (7) |
C14A—F1A—F6A | 52.8 (7) | F6B—C14B—C1B | 114.0 (5) |
F2A—F5A—C14A | 65.9 (9) | C10B—C1B—C2B | 118.6 (3) |
F2A—F5A—F3A | 113.0 (13) | C10B—C1B—C14B | 121.3 (4) |
C14A—F5A—F3A | 54.0 (7) | C2B—C1B—C14B | 120.1 (4) |
F1A—F4A—C14A | 71.0 (10) | C11B—C10B—C1B | 121.1 (3) |
F1A—F4A—F2A | 125.0 (15) | C10B—C11B—C4B | 120.4 (3) |
C14A—F4A—F2A | 58.2 (6) | C3B—C4B—C11B | 118.3 (3) |
F3A—F6A—C14A | 73.1 (15) | C3B—C4B—C5B | 121.2 (3) |
F3A—F6A—F1A | 124.0 (19) | C11B—C4B—C5B | 120.4 (3) |
C14A—F6A—F1A | 58.0 (8) | C12B—C5B—O1B | 108.7 (3) |
C6'—O1'—C5' | 107.3 (2) | C12B—C5B—C4B | 134.0 (3) |
C5—O1—C6 | 107.3 (2) | O1B—C5B—C4B | 117.3 (3) |
C6B—O1B—C5B | 107.4 (2) | C13B—C6B—O1B | 108.7 (3) |
C5A—O1A—C6A | 107.4 (2) | C13B—C6B—C7B | 134.9 (3) |
F2'—C14'—F4' | 82.2 (13) | O1B—C6B—C7B | 116.4 (3) |
F2'—C14'—F6' | 124.0 (13) | C9B—C7B—C8B | 117.4 (3) |
F4'—C14'—F6' | 106.9 (11) | C9B—C7B—C6B | 122.2 (3) |
F2'—C14'—F3' | 106.3 (14) | C8B—C7B—C6B | 120.4 (3) |
F4'—C14'—F3' | 121.1 (12) | C8Bi—C9B—C7B | 120.9 (3) |
F6'—C14'—F3' | 22.3 (14) | C9Bi—C8B—C7B | 121.7 (3) |
F2'—C14'—F1' | 102.9 (13) | F5B—F2B—F6B | 132.9 (16) |
F4'—C14'—F1' | 22.6 (14) | F5B—F2B—C14B | 69.2 (9) |
F6'—C14'—F1' | 87.7 (12) | F6B—F2B—C14B | 68.6 (8) |
F3'—C14'—F1' | 105.9 (11) | F4B—F3B—C14B | 56.4 (7) |
F2'—C14'—F5' | 25.6 (17) | F4B—F3B—F6B | 108.7 (9) |
F4'—C14'—F5' | 105.7 (13) | C14B—F3B—F6B | 60.7 (6) |
F6'—C14'—F5' | 106.3 (14) | F4B—F1B—C14B | 62.3 (12) |
F3'—C14'—F5' | 85.4 (13) | F4B—F1B—F5B | 112.8 (18) |
F1'—C14'—F5' | 123.9 (12) | C14B—F1B—F5B | 56.2 (6) |
F2'—C14'—C1' | 114.5 (11) | F2B—F6B—F3B | 115.1 (14) |
F4'—C14'—C1' | 114.5 (10) | F2B—F6B—C14B | 59.2 (7) |
F6'—C14'—C1' | 111.0 (8) | F3B—F6B—C14B | 59.6 (8) |
F3'—C14'—C1' | 113.7 (7) | F2B—F5B—C14B | 61.4 (7) |
F1'—C14'—C1' | 112.6 (10) | F2B—F5B—F1B | 112.5 (12) |
F5'—C14'—C1' | 111.9 (12) | C14B—F5B—F1B | 57.4 (7) |
C2'—C1'—C10' | 119.7 (3) | F1B—F4B—C14B | 75.2 (11) |
C2'—C1'—C14' | 119.9 (3) | F1B—F4B—F3B | 137.3 (16) |
C10'—C1'—C14' | 120.4 (3) | C14B—F4B—F3B | 64.8 (10) |
C3'—C2'—C1' | 120.5 (3) | C2B—C3B—C4B | 120.5 (3) |
C2'—C3'—C4' | 120.7 (3) | C3B—C2B—C1B | 121.0 (3) |
C3'—C4'—C11' | 118.4 (3) | C5B—C12B—C13B | 107.4 (3) |
C3'—C4'—C5' | 122.1 (3) | C6B—C13B—C12B | 107.8 (3) |
C11'—C4'—C5' | 119.5 (3) | F2A—C14A—F6A | 131.9 (8) |
C12'—C5'—O1' | 108.7 (3) | F2A—C14A—F4A | 62.0 (6) |
C12'—C5'—C4' | 134.4 (3) | F6A—C14A—F4A | 108.7 (9) |
O1'—C5'—C4' | 116.8 (3) | F2A—C14A—F3A | 108.4 (8) |
C13'—C6'—O1' | 108.9 (3) | F6A—C14A—F3A | 37.0 (11) |
C13'—C6'—C7' | 133.8 (3) | F4A—C14A—F3A | 128.3 (7) |
O1'—C6'—C7' | 117.2 (3) | F2A—C14A—F5A | 43.3 (6) |
C9—C7'—C8' | 117.7 (3) | F6A—C14A—F5A | 105.7 (10) |
C9—C7'—C6' | 122.3 (3) | F4A—C14A—F5A | 102.1 (7) |
C8'—C7'—C6' | 120.0 (3) | F3A—C14A—F5A | 70.9 (8) |
C9'—C8'—C7' | 121.5 (3) | F2A—C14A—F1A | 104.2 (7) |
C8'—C9'—C7 | 121.0 (3) | F6A—C14A—F1A | 69.2 (11) |
C9'—C7—C8 | 117.5 (3) | F4A—C14A—F1A | 44.9 (6) |
C9'—C7—C6 | 122.0 (3) | F3A—C14A—F1A | 102.2 (8) |
C8—C7—C6 | 120.6 (3) | F5A—C14A—F1A | 133.2 (6) |
C13—C6—O1 | 108.9 (3) | F2A—C14A—C1A | 114.6 (5) |
C13—C6—C7 | 135.1 (3) | F6A—C14A—C1A | 111.7 (7) |
O1—C6—C7 | 115.9 (3) | F4A—C14A—C1A | 114.9 (5) |
C12—C5—O1 | 108.6 (3) | F3A—C14A—C1A | 114.6 (5) |
C12—C5—C4 | 135.0 (3) | F5A—C14A—C1A | 113.1 (6) |
O1—C5—C4 | 116.3 (3) | F1A—C14A—C1A | 111.6 (5) |
C3—C4—C11 | 118.2 (3) | C2A—C1A—C10A | 119.3 (3) |
C3—C4—C5 | 121.1 (3) | C2A—C1A—C14A | 119.6 (3) |
C11—C4—C5 | 120.6 (3) | C10A—C1A—C14A | 121.1 (3) |
C10—C11—C4 | 120.9 (3) | C3A—C2A—C1A | 120.9 (3) |
C1—C10—C11 | 120.2 (3) | C2A—C3A—C4A | 120.6 (3) |
C2—C1—C10 | 119.1 (3) | C3A—C4A—C11A | 118.4 (3) |
C2—C1—C14 | 120.5 (3) | C3A—C4A—C5A | 121.8 (3) |
C10—C1—C14 | 120.4 (3) | C11A—C4A—C5A | 119.7 (3) |
F1—C14—F5 | 70.8 (7) | C12A—C5A—O1A | 108.8 (3) |
F1—C14—F6 | 122.8 (9) | C12A—C5A—C4A | 134.7 (3) |
F5—C14—F6 | 109.5 (9) | O1A—C5A—C4A | 116.5 (3) |
F1—C14—F3 | 106.9 (9) | C13A—C6A—O1A | 109.1 (3) |
F5—C14—F3 | 128.6 (9) | C13A—C6A—C7A | 134.1 (3) |
F6—C14—F3 | 27.1 (11) | O1A—C6A—C7A | 116.7 (3) |
F1—C14—F4 | 31.6 (9) | C8A—C7A—C9A | 117.7 (3) |
F5—C14—F4 | 101.2 (8) | C8A—C7A—C6A | 120.3 (3) |
F6—C14—F4 | 104.8 (11) | C9A—C7A—C6A | 122.1 (3) |
F3—C14—F4 | 81.5 (9) | C9Aii—C8A—C7A | 121.3 (3) |
F1—C14—F2 | 107.2 (8) | C8Aii—C9A—C7A | 121.1 (3) |
F5—C14—F2 | 39.9 (7) | C10A—C11A—C4A | 120.6 (3) |
F6—C14—F2 | 76.6 (9) | C11A—C10A—C1A | 120.2 (3) |
F3—C14—F2 | 102.4 (8) | C6A—C13A—C12A | 107.3 (3) |
F4—C14—F2 | 132.2 (7) | C5A—C12A—C13A | 107.5 (3) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+2. |