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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520618011782/um5015sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618011782/um5015Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618011782/um5015IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618011782/um5015IIIsup4.hkl
Contains datablock III

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520618011782/um5015sup5.pdf
Supplementary material

CCDC references: 1842017; 1842018; 1842019

Computing details top

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).

(I) top
Crystal data top
C14H8F3OF(000) = 508
Mr = 249.20Dx = 1.517 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 23.238 (4) ÅCell parameters from 1580 reflections
b = 7.5293 (11) Åθ = 3.2–21.9°
c = 6.2437 (9) ŵ = 0.13 mm1
β = 92.830 (6)°T = 296 K
V = 1091.1 (3) Å3PLATE, yellow
Z = 40.25 × 0.24 × 0.01 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1221 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.048
φ and ω scansθmax = 24.9°, θmin = 3.2°
Absorption correction: multi-scan
SADABS-2008/1
h = 2725
Tmin = 0.845, Tmax = 0.980k = 88
8904 measured reflectionsl = 77
1882 independent reflections
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-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 reflectionsΔρmax = 0.13 e Å3
190 parametersΔρmin = 0.17 e Å3
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
xyzUiso*/UeqOcc. (<1)
F10.5303 (2)0.5052 (10)0.3208 (11)0.102 (2)0.5
F20.5645 (3)0.6943 (6)0.1366 (14)0.096 (3)0.5
F30.5702 (5)0.4344 (14)0.0320 (12)0.143 (5)0.5
F60.5800 (5)0.4985 (12)0.0012 (7)0.105 (3)0.5
F50.5505 (4)0.6864 (7)0.2005 (16)0.128 (4)0.5
F40.5394 (3)0.4079 (9)0.2571 (14)0.120 (3)0.5
O10.84207 (6)0.50926 (16)0.54655 (19)0.0421 (4)
C140.57456 (10)0.5333 (3)0.2017 (4)0.0576 (6)
C10.63154 (9)0.5217 (2)0.3237 (3)0.0443 (5)
C20.68054 (9)0.5853 (3)0.2342 (3)0.0464 (5)
H20.6777530.6372830.0989840.056*
C30.73353 (9)0.5732 (2)0.3420 (3)0.0435 (5)
H30.7661260.6178000.2800440.052*
C40.73829 (9)0.4940 (2)0.5443 (3)0.0390 (5)
C50.79401 (9)0.4746 (2)0.6597 (3)0.0411 (5)
C60.88974 (9)0.4721 (2)0.6791 (3)0.0408 (5)
C70.94559 (9)0.4885 (2)0.5883 (3)0.0398 (5)
C80.99465 (10)0.4188 (3)0.6949 (3)0.0450 (5)
H80.9912340.3634150.8267340.054*
C90.95230 (9)0.5699 (2)0.3899 (3)0.0447 (5)
H90.9203200.6170930.3146040.054*
C110.68877 (9)0.4310 (3)0.6332 (3)0.0475 (5)
H110.6912960.3778090.7678050.057*
C100.63595 (10)0.4459 (3)0.5253 (3)0.0502 (6)
H100.6030510.4047540.5883390.060*
C120.81087 (10)0.4201 (3)0.8589 (3)0.0501 (6)
H120.7868120.3894430.9676980.060*
C130.87162 (10)0.4182 (3)0.8719 (3)0.0502 (6)
H130.8949680.3858920.9908430.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.049 (3)0.156 (6)0.099 (3)0.024 (4)0.001 (2)0.034 (4)
F20.053 (3)0.082 (4)0.151 (6)0.008 (2)0.019 (3)0.056 (4)
F30.121 (9)0.118 (5)0.181 (9)0.053 (5)0.088 (7)0.093 (5)
F60.069 (3)0.193 (9)0.051 (2)0.008 (5)0.009 (2)0.031 (3)
F50.082 (5)0.118 (6)0.178 (7)0.057 (4)0.051 (5)0.084 (5)
F40.071 (4)0.139 (5)0.144 (7)0.060 (4)0.038 (3)0.062 (5)
O10.0409 (9)0.0443 (7)0.0409 (7)0.0011 (6)0.0020 (7)0.0055 (6)
C140.0490 (17)0.0600 (16)0.0636 (17)0.0001 (12)0.0010 (13)0.0017 (14)
C10.0425 (14)0.0405 (11)0.0500 (12)0.0007 (10)0.0039 (10)0.0012 (10)
C20.0515 (15)0.0447 (12)0.0430 (11)0.0003 (10)0.0031 (11)0.0063 (10)
C30.0404 (13)0.0463 (11)0.0446 (11)0.0014 (9)0.0083 (10)0.0039 (10)
C40.0438 (13)0.0331 (10)0.0404 (11)0.0016 (9)0.0055 (9)0.0006 (9)
C50.0469 (14)0.0354 (10)0.0414 (11)0.0003 (9)0.0064 (10)0.0009 (9)
C60.0463 (14)0.0333 (10)0.0417 (11)0.0005 (9)0.0075 (10)0.0019 (9)
C70.0431 (14)0.0336 (10)0.0420 (11)0.0030 (9)0.0060 (9)0.0015 (9)
C80.0506 (15)0.0436 (12)0.0399 (11)0.0026 (10)0.0070 (10)0.0060 (9)
C90.0442 (15)0.0430 (11)0.0456 (12)0.0008 (9)0.0109 (10)0.0052 (10)
C110.0524 (15)0.0489 (12)0.0415 (11)0.0023 (11)0.0068 (10)0.0085 (10)
C100.0469 (15)0.0506 (13)0.0540 (13)0.0046 (10)0.0118 (11)0.0042 (11)
C120.0573 (17)0.0523 (13)0.0411 (12)0.0024 (11)0.0053 (10)0.0052 (10)
C130.0559 (16)0.0528 (12)0.0408 (12)0.0038 (11)0.0059 (11)0.0050 (10)
Geometric parameters (Å, º) top
F1—F40.864 (9)C3—C41.397 (3)
F1—C141.316 (4)C3—H30.9300
F1—F51.637 (9)C4—C111.386 (3)
F2—F50.531 (15)C4—C51.458 (3)
F2—C141.296 (4)C5—C121.349 (3)
F2—F61.753 (10)C6—C131.357 (3)
F3—F60.577 (18)C6—C71.447 (3)
F3—C141.295 (4)C7—C81.394 (3)
F3—F41.621 (10)C7—C91.398 (3)
F6—C141.306 (4)C8—C9i1.368 (3)
F5—C141.281 (4)C8—H80.9300
F4—C141.307 (4)C9—H90.9300
O1—C51.376 (2)C11—C101.375 (3)
O1—C61.378 (2)C11—H110.9300
C14—C11.497 (3)C10—H100.9300
C1—C21.379 (3)C12—C131.410 (3)
C1—C101.381 (3)C12—H120.9300
C2—C31.377 (3)C13—H130.9300
C2—H20.9300
F4—F1—C1470.2 (5)C2—C1—C10119.2 (2)
F4—F1—F5114.4 (8)C2—C1—C14120.06 (19)
C14—F1—F550.0 (3)C10—C1—C14120.8 (2)
F5—F2—C1476.6 (7)C3—C2—C1121.04 (19)
F5—F2—F6115.1 (12)C3—C2—H2119.5
C14—F2—F647.9 (3)C1—C2—H2119.5
F6—F3—C1478.2 (8)C2—C3—C4120.0 (2)
F6—F3—F4127.9 (10)C2—C3—H3120.0
C14—F3—F451.8 (3)C4—C3—H3120.0
F3—F6—C1476.1 (7)C11—C4—C3118.57 (19)
F3—F6—F2115.6 (13)C11—C4—C5120.16 (18)
C14—F6—F247.4 (3)C3—C4—C5121.26 (19)
F2—F5—C1479.7 (8)C12—C5—O1108.97 (18)
F2—F5—F1129.7 (10)C12—C5—C4134.2 (2)
C14—F5—F151.9 (3)O1—C5—C4116.78 (16)
F1—F4—C1471.3 (4)C13—C6—O1108.54 (19)
F1—F4—F3115.0 (8)C13—C6—C7134.17 (19)
C14—F4—F351.1 (3)O1—C6—C7117.21 (16)
C5—O1—C6107.56 (15)C8—C7—C9117.62 (19)
F5—C14—F3119.8 (6)C8—C7—C6120.62 (18)
F5—C14—F223.8 (7)C9—C7—C6121.74 (17)
F3—C14—F2106.0 (7)C9i—C8—C7121.58 (19)
F5—C14—F6103.8 (6)C9i—C8—H8119.2
F3—C14—F625.7 (8)C7—C8—H8119.2
F2—C14—F684.7 (6)C8i—C9—C7120.80 (18)
F5—C14—F4111.9 (6)C8i—C9—H9119.6
F3—C14—F477.1 (6)C7—C9—H9119.6
F2—C14—F4130.8 (5)C10—C11—C4120.96 (19)
F6—C14—F4101.8 (6)C10—C11—H11119.5
F5—C14—F178.2 (5)C4—C11—H11119.5
F3—C14—F1109.7 (6)C11—C10—C1120.3 (2)
F2—C14—F1101.2 (5)C11—C10—H10119.9
F6—C14—F1129.2 (6)C1—C10—H10119.9
F4—C14—F138.5 (4)C5—C12—C13107.50 (19)
F5—C14—C1115.5 (4)C5—C12—H12126.2
F3—C14—C1114.5 (5)C13—C12—H12126.2
F2—C14—C1110.8 (4)C6—C13—C12107.41 (18)
F6—C14—C1110.8 (5)C6—C13—H13126.3
F4—C14—C1111.9 (4)C12—C13—H13126.3
F1—C14—C1113.5 (4)
F4—F3—F6—C1416 (2)F1—F4—C14—F247.7 (13)
C14—F3—F6—F226.9 (14)F3—F4—C14—F2100.1 (8)
F4—F3—F6—F211 (3)F1—F4—C14—F6140.9 (10)
F5—F2—F6—F33 (3)F3—F4—C14—F66.9 (10)
C14—F2—F6—F337 (2)F3—F4—C14—F1147.8 (12)
F5—F2—F6—C1439.7 (18)F1—F4—C14—C1100.8 (10)
F6—F2—F5—C1429.2 (11)F3—F4—C14—C1111.5 (6)
C14—F2—F5—F114.8 (19)F4—F1—C14—F5151.1 (11)
F6—F2—F5—F114 (3)F4—F1—C14—F333.5 (12)
F4—F1—F5—F211 (3)F5—F1—C14—F3117.6 (7)
C14—F1—F5—F219 (2)F4—F1—C14—F2145.2 (10)
F4—F1—F5—C1429.9 (11)F5—F1—C14—F25.9 (8)
F5—F1—F4—C1423.9 (8)F4—F1—C14—F652.9 (13)
C14—F1—F4—F327.3 (8)F5—F1—C14—F698.3 (8)
F5—F1—F4—F33.3 (15)F5—F1—C14—F4151.1 (11)
F6—F3—F4—F114 (3)F4—F1—C14—C196.0 (10)
C14—F3—F4—F133.9 (11)F5—F1—C14—C1112.8 (5)
F6—F3—F4—C1420 (3)F5—C14—C1—C278.0 (6)
F2—F5—C14—F359 (2)F3—C14—C1—C267.2 (6)
F1—F5—C14—F3106.1 (7)F2—C14—C1—C252.7 (5)
F1—F5—C14—F2165.5 (19)F6—C14—C1—C239.6 (5)
F2—F5—C14—F637.6 (19)F4—C14—C1—C2152.4 (5)
F1—F5—C14—F6127.9 (6)F1—C14—C1—C2165.7 (4)
F2—F5—C14—F4146.6 (17)F5—C14—C1—C10102.6 (6)
F1—F5—C14—F418.9 (7)F3—C14—C1—C10112.2 (7)
F2—F5—C14—F1165.5 (19)F2—C14—C1—C10128.0 (5)
F2—F5—C14—C183.9 (18)F6—C14—C1—C10139.7 (5)
F1—F5—C14—C1110.6 (4)F4—C14—C1—C1026.9 (6)
F6—F3—C14—F556 (2)F1—C14—C1—C1014.9 (5)
F4—F3—C14—F5108.0 (7)C10—C1—C2—C30.5 (3)
F6—F3—C14—F235 (2)C14—C1—C2—C3178.86 (18)
F4—F3—C14—F2129.2 (6)C1—C2—C3—C40.6 (3)
F4—F3—C14—F6164 (2)C2—C3—C4—C110.8 (3)
F6—F3—C14—F4164 (2)C2—C3—C4—C5178.21 (18)
F6—F3—C14—F1144 (2)C6—O1—C5—C121.0 (2)
F4—F3—C14—F120.7 (7)C6—O1—C5—C4176.12 (15)
F6—F3—C14—C187 (2)C11—C4—C5—C128.0 (3)
F4—F3—C14—C1108.4 (4)C3—C4—C5—C12173.0 (2)
F6—F2—C14—F5143.5 (19)C11—C4—C5—O1168.18 (16)
F5—F2—C14—F3129.0 (18)C3—C4—C5—O110.8 (3)
F6—F2—C14—F314.5 (10)C5—O1—C6—C130.9 (2)
F5—F2—C14—F6143.5 (19)C5—O1—C6—C7176.17 (14)
F5—F2—C14—F442 (2)C13—C6—C7—C89.7 (3)
F6—F2—C14—F4101.0 (8)O1—C6—C7—C8166.54 (16)
F5—F2—C14—F114.5 (19)C13—C6—C7—C9171.9 (2)
F6—F2—C14—F1129.0 (6)O1—C6—C7—C911.9 (3)
F5—F2—C14—C1106.2 (17)C9—C7—C8—C9i0.3 (3)
F6—F2—C14—C1110.3 (5)C6—C7—C8—C9i178.84 (17)
F3—F6—C14—F5132 (2)C8—C7—C9—C8i0.3 (3)
F2—F6—C14—F514.3 (7)C6—C7—C9—C8i178.82 (17)
F2—F6—C14—F3146 (2)C3—C4—C11—C100.0 (3)
F3—F6—C14—F2146 (2)C5—C4—C11—C10179.07 (18)
F3—F6—C14—F416 (2)C4—C11—C10—C11.1 (3)
F2—F6—C14—F4130.6 (5)C2—C1—C10—C111.3 (3)
F3—F6—C14—F146 (2)C14—C1—C10—C11178.00 (18)
F2—F6—C14—F1100.2 (7)O1—C5—C12—C130.7 (2)
F3—F6—C14—C1103 (2)C4—C5—C12—C13175.7 (2)
F2—F6—C14—C1110.3 (4)O1—C6—C13—C120.5 (2)
F1—F4—C14—F530.6 (12)C7—C6—C13—C12175.90 (19)
F3—F4—C14—F5117.2 (7)C5—C12—C13—C60.1 (2)
F1—F4—C14—F3147.8 (12)
Symmetry code: (i) x+2, y+1, z+1.
(II) top
Crystal data top
C14H8F3OF(000) = 508
Mr = 249.20Dx = 1.527 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.505 (1) ÅCell parameters from 3034 reflections
b = 6.2350 (6) Åθ = 2.7–26.8°
c = 16.0118 (16) ŵ = 0.13 mm1
β = 109.293 (6)°T = 296 K
V = 1084.08 (18) Å3Needle, green
Z = 40.60 × 0.18 × 0.05 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1436 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan
SADABS-2008/1
h = 1313
Tmin = 0.869, Tmax = 0.928k = 77
8382 measured reflectionsl = 1819
1919 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-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 reflectionsΔρmax = 0.14 e Å3
190 parametersΔρmin = 0.17 e Å3
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
xyzUiso*/UeqOcc. (<1)
F20.4411 (6)0.2322 (18)0.9116 (4)0.0711 (19)0.5
F10.5987 (11)0.2020 (14)1.0186 (6)0.0678 (19)0.5
F30.5801 (13)0.4747 (16)0.9333 (9)0.106 (3)0.5
F60.5530 (12)0.4655 (15)0.9205 (8)0.099 (3)0.5
F40.6185 (12)0.2315 (17)1.0188 (6)0.089 (3)0.5
F50.4456 (7)0.195 (2)0.9135 (6)0.105 (3)0.5
O10.83660 (9)0.05832 (17)0.66274 (7)0.0431 (3)
C140.56092 (16)0.2619 (3)0.93363 (12)0.0532 (4)
C10.62232 (14)0.1458 (3)0.87832 (10)0.0432 (4)
C20.62629 (15)0.2362 (3)0.80009 (11)0.0484 (4)
H20.5889500.3681010.7815340.058*
C30.68535 (15)0.1313 (3)0.74983 (10)0.0470 (4)
H30.6878110.1934020.6976350.056*
C40.74137 (13)0.0667 (2)0.77632 (10)0.0398 (4)
C50.80911 (13)0.1755 (2)0.72656 (10)0.0411 (4)
C60.90561 (14)0.1876 (3)0.62774 (10)0.0426 (4)
C70.95196 (13)0.0920 (2)0.56235 (9)0.0414 (4)
C81.03866 (14)0.2002 (3)0.53401 (10)0.0478 (4)
H81.0654650.3353990.5568400.057*
C90.91490 (14)0.1111 (3)0.52687 (10)0.0461 (4)
H90.8577570.1874020.5447290.055*
C110.73446 (14)0.1575 (3)0.85406 (10)0.0474 (4)
H110.7700870.2908040.8721780.057*
C100.67560 (15)0.0526 (3)0.90450 (11)0.0483 (4)
H100.6717350.1153650.9562090.058*
C130.91961 (15)0.3819 (3)0.66766 (11)0.0509 (4)
H130.9618180.4988630.6557510.061*
C120.85810 (15)0.3738 (3)0.73079 (11)0.0494 (4)
H120.8524100.4843600.7682480.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F20.041 (3)0.118 (4)0.054 (2)0.018 (2)0.0137 (18)0.012 (2)
F10.085 (5)0.076 (2)0.050 (3)0.024 (3)0.032 (3)0.010 (2)
F30.162 (6)0.054 (4)0.155 (7)0.035 (4)0.124 (5)0.038 (4)
F60.165 (7)0.059 (5)0.112 (4)0.035 (5)0.099 (4)0.018 (4)
F40.073 (3)0.151 (7)0.046 (3)0.002 (3)0.026 (2)0.031 (3)
F50.074 (4)0.123 (5)0.145 (5)0.012 (3)0.071 (4)0.008 (3)
O10.0484 (6)0.0454 (6)0.0390 (6)0.0060 (5)0.0192 (5)0.0002 (5)
C140.0562 (11)0.0580 (12)0.0527 (11)0.0002 (9)0.0279 (9)0.0026 (9)
C10.0430 (8)0.0468 (9)0.0425 (9)0.0055 (7)0.0177 (7)0.0014 (7)
C20.0560 (10)0.0457 (9)0.0468 (9)0.0081 (8)0.0213 (8)0.0056 (7)
C30.0575 (10)0.0490 (9)0.0382 (8)0.0034 (8)0.0209 (7)0.0065 (7)
C40.0404 (8)0.0416 (8)0.0368 (8)0.0031 (7)0.0122 (6)0.0011 (7)
C50.0425 (8)0.0445 (9)0.0362 (8)0.0018 (7)0.0128 (7)0.0011 (7)
C60.0412 (8)0.0482 (9)0.0379 (8)0.0056 (7)0.0125 (7)0.0072 (7)
C70.0411 (8)0.0474 (9)0.0339 (8)0.0050 (7)0.0102 (7)0.0066 (7)
C80.0534 (10)0.0477 (9)0.0437 (9)0.0139 (8)0.0181 (8)0.0001 (7)
C90.0476 (9)0.0521 (10)0.0406 (9)0.0135 (8)0.0175 (7)0.0043 (7)
C110.0557 (10)0.0419 (9)0.0475 (10)0.0024 (7)0.0213 (8)0.0073 (7)
C100.0585 (10)0.0490 (9)0.0434 (9)0.0036 (8)0.0247 (8)0.0065 (7)
C130.0545 (10)0.0455 (9)0.0527 (10)0.0102 (8)0.0176 (8)0.0030 (8)
C120.0526 (9)0.0467 (9)0.0501 (10)0.0029 (8)0.0183 (8)0.0047 (8)
Geometric parameters (Å, º) top
F2—C141.318 (7)C4—C51.454 (2)
F1—C141.337 (8)C5—C121.351 (2)
F3—C141.345 (10)C6—C131.354 (2)
F6—C141.285 (9)C6—C71.451 (2)
F4—C141.318 (9)C7—C91.396 (2)
F5—C141.325 (9)C7—C81.398 (2)
O1—C61.3742 (18)C8—C9i1.374 (2)
O1—C51.3753 (18)C8—H80.9300
C14—C11.490 (2)C9—H90.9300
C1—C101.383 (2)C11—C101.378 (2)
C1—C21.388 (2)C11—H110.9300
C2—C31.378 (2)C10—H100.9300
C2—H20.9300C13—C121.413 (2)
C3—C41.392 (2)C13—H130.9300
C3—H30.9300C12—H120.9300
C4—C111.393 (2)
C6—O1—C5107.28 (12)C3—C4—C11118.36 (14)
F6—C14—F4107.2 (7)C3—C4—C5121.66 (14)
F6—C14—F294.8 (8)C11—C4—C5119.96 (14)
F4—C14—F2112.3 (7)C12—C5—O1109.20 (14)
F6—C14—F5105.0 (8)C12—C5—C4133.62 (15)
F4—C14—F5109.1 (7)O1—C5—C4117.13 (13)
F2—C14—F510.2 (10)C13—C6—O1109.09 (14)
F6—C14—F1115.1 (7)C13—C6—C7133.90 (15)
F4—C14—F112.6 (11)O1—C6—C7116.93 (13)
F2—C14—F1101.1 (6)C9—C7—C8117.41 (15)
F5—C14—F197.1 (7)C9—C7—C6122.07 (14)
F6—C14—F313.6 (11)C8—C7—C6120.51 (14)
F4—C14—F396.8 (8)C9i—C8—C7121.42 (15)
F2—C14—F3107.2 (8)C9i—C8—H8119.3
F5—C14—F3117.5 (8)C7—C8—H8119.3
F1—C14—F3106.3 (7)C8i—C9—C7121.17 (15)
F6—C14—C1113.9 (6)C8i—C9—H9119.4
F4—C14—C1111.7 (5)C7—C9—H9119.4
F2—C14—C1115.6 (4)C10—C11—C4121.00 (15)
F5—C14—C1109.6 (5)C10—C11—H11119.5
F1—C14—C1114.2 (4)C4—C11—H11119.5
F3—C14—C1111.5 (6)C11—C10—C1120.07 (15)
C10—C1—C2119.57 (15)C11—C10—H10120.0
C10—C1—C14120.28 (15)C1—C10—H10120.0
C2—C1—C14120.15 (15)C6—C13—C12107.22 (15)
C3—C2—C1120.26 (15)C6—C13—H13126.4
C3—C2—H2119.9C12—C13—H13126.4
C1—C2—H2119.9C5—C12—C13107.21 (15)
C2—C3—C4120.72 (15)C5—C12—H12126.4
C2—C3—H3119.6C13—C12—H12126.4
C4—C3—H3119.6
F6—C14—C1—C10157.5 (6)C11—C4—C5—O1165.59 (13)
F4—C14—C1—C1035.9 (7)C5—O1—C6—C130.84 (16)
F2—C14—C1—C1094.2 (5)C5—O1—C6—C7176.26 (13)
F5—C14—C1—C1085.2 (5)C13—C6—C7—C9174.99 (17)
F1—C14—C1—C1022.5 (6)O1—C6—C7—C98.8 (2)
F3—C14—C1—C10143.0 (6)C13—C6—C7—C86.5 (3)
F6—C14—C1—C222.5 (7)O1—C6—C7—C8169.69 (13)
F4—C14—C1—C2144.1 (6)C9—C7—C8—C9i0.4 (3)
F2—C14—C1—C285.8 (5)C6—C7—C8—C9i179.00 (15)
F5—C14—C1—C294.8 (5)C8—C7—C9—C8i0.4 (3)
F1—C14—C1—C2157.5 (6)C6—C7—C9—C8i178.98 (15)
F3—C14—C1—C237.0 (7)C3—C4—C11—C101.1 (2)
C10—C1—C2—C31.5 (2)C5—C4—C11—C10176.98 (14)
C14—C1—C2—C3178.58 (14)C4—C11—C10—C10.0 (2)
C1—C2—C3—C40.3 (2)C2—C1—C10—C111.3 (2)
C2—C3—C4—C111.0 (2)C14—C1—C10—C11178.69 (15)
C2—C3—C4—C5177.06 (14)O1—C6—C13—C120.60 (18)
C6—O1—C5—C120.76 (16)C7—C6—C13—C12175.82 (16)
C6—O1—C5—C4176.88 (12)O1—C5—C12—C130.40 (17)
C3—C4—C5—C12170.59 (17)C4—C5—C12—C13176.71 (16)
C11—C4—C5—C1211.3 (3)C6—C13—C12—C50.12 (18)
C3—C4—C5—O112.5 (2)
Symmetry code: (i) x+2, y, z+1.
(III) top
Crystal data top
C28H16F6O2F(000) = 2032
Mr = 498.41Dx = 1.502 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 20.5435 (12) ÅCell parameters from 4952 reflections
b = 6.2569 (3) Åθ = 2.3–22.7°
c = 35.797 (2) ŵ = 0.13 mm1
β = 106.649 (3)°T = 296 K
V = 4408.4 (4) Å3Needle, green
Z = 81.00 × 0.12 × 0.02 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3612 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.093
φ and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
SADABS-2008/1
h = 2424
Tmin = 0.719, Tmax = 0.862k = 77
50500 measured reflectionsl = 4242
7760 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-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 reflectionsΔρmax = 0.17 e Å3
757 parametersΔρmin = 0.15 e Å3
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
xyzUiso*/UeqOcc. (<1)
F20.1566 (6)0.4279 (16)0.7220 (3)0.096 (3)0.5
F30.2076 (5)0.374 (2)0.6819 (2)0.099 (5)0.5
F10.1322 (6)0.1632 (19)0.6852 (5)0.132 (6)0.5
F50.1287 (6)0.317 (3)0.7160 (3)0.151 (6)0.5
F60.2039 (6)0.441 (2)0.6932 (5)0.196 (8)0.5
F40.1564 (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
F2A0.0079 (5)0.288 (3)0.8009 (5)0.124 (4)0.5
F3A0.0730 (7)0.0483 (14)0.7941 (5)0.117 (6)0.5
F1A0.0549 (7)0.308 (2)0.7573 (2)0.102 (3)0.5
F5A0.0261 (8)0.159 (4)0.8135 (3)0.150 (8)0.5
F4A0.0217 (7)0.3696 (17)0.7702 (5)0.133 (4)0.5
F6A0.0846 (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)
O10.43589 (9)0.0604 (3)0.84618 (5)0.0499 (5)
O1B0.83778 (10)0.4372 (3)0.92245 (5)0.0511 (5)
O1A0.33691 (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)
H2'0.8995060.3622491.1048840.060*
C3'0.85428 (14)0.1268 (5)1.06868 (8)0.0471 (7)
H3'0.8119320.1922061.0602610.057*
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)
H8'0.6283760.3324710.9134260.064*
C9'0.55674 (14)0.1095 (5)0.89433 (8)0.0496 (8)
H9'0.5324930.1852320.8724000.060*
C70.53445 (14)0.0923 (5)0.90144 (8)0.0442 (7)
C60.47441 (15)0.1899 (5)0.87552 (8)0.0474 (8)
C50.38002 (14)0.1763 (5)0.82620 (8)0.0491 (8)
C40.33056 (14)0.0648 (5)0.79488 (8)0.0497 (8)
C110.26693 (16)0.1535 (5)0.77766 (9)0.0624 (9)
H110.2562150.2863600.7859460.075*
C100.21935 (15)0.0466 (6)0.74835 (9)0.0659 (9)
H100.1770890.1081960.7370190.079*
C10.23443 (15)0.1511 (5)0.73589 (8)0.0532 (8)
C140.1821 (2)0.2720 (7)0.70584 (12)0.0650 (9)
C130.44382 (16)0.3814 (5)0.87351 (9)0.0586 (9)
H130.4594530.4979350.8897330.070*
C120.38389 (16)0.3729 (5)0.84235 (9)0.0609 (9)
H120.3525250.4828510.8342950.073*
C12'0.80341 (15)0.3792 (5)1.00886 (9)0.0559 (8)
H12'0.8342860.4910281.0161100.067*
C13'0.74123 (16)0.3856 (5)0.97937 (9)0.0563 (8)
H13'0.7233690.5021230.9636390.068*
C10'0.98025 (15)0.0672 (5)1.09448 (9)0.0556 (8)
H10'1.0224540.1330651.1034440.067*
C11'0.92788 (15)0.1688 (4)1.06760 (8)0.0528 (8)
H11'0.9351740.3028421.0583000.063*
C90.62855 (14)0.1078 (5)0.96047 (8)0.0484 (8)
H90.6521620.1816280.9827860.058*
C80.57179 (14)0.1985 (5)0.93532 (8)0.0512 (8)
H80.5578450.3332150.9408880.061*
C30.34516 (15)0.1331 (5)0.78177 (9)0.0570 (8)
H30.3875600.1947450.7926770.068*
C20.29755 (14)0.2391 (5)0.75279 (9)0.0577 (8)
H20.3080690.3721380.7444740.069*
C14B0.5713 (2)0.7464 (8)0.78711 (13)0.0738 (10)
C1B0.62628 (15)0.6310 (5)0.81660 (9)0.0564 (8)
C10B0.61485 (16)0.4342 (6)0.83077 (10)0.0645 (9)
H10B0.5725120.3699540.8212230.077*
C11B0.66498 (16)0.3311 (5)0.85882 (9)0.0617 (9)
H11B0.6562460.1983090.8680110.074*
C4B0.72881 (14)0.4246 (5)0.87353 (8)0.0469 (8)
C5B0.78112 (15)0.3189 (5)0.90387 (8)0.0493 (8)
C6B0.87887 (15)0.3094 (5)0.95090 (8)0.0494 (8)
C7B0.94029 (14)0.4073 (5)0.97537 (8)0.0479 (8)
C9B0.96149 (15)0.6107 (5)0.96776 (8)0.0525 (8)
H9B0.9359860.6863570.9461490.063*
C8B0.98052 (15)0.2996 (5)1.00824 (9)0.0555 (8)
H8B0.9676080.1638411.0139470.067*
F2B0.5819 (10)0.767 (4)0.7553 (3)0.149 (7)0.5
F3B0.5620 (8)0.9367 (16)0.8002 (3)0.095 (3)0.5
F1B0.5105 (5)0.6623 (19)0.7826 (7)0.136 (7)0.5
F6B0.5923 (6)0.920 (3)0.7726 (9)0.182 (8)0.5
F5B0.5488 (9)0.637 (2)0.7550 (4)0.131 (5)0.5
F4B0.5209 (10)0.787 (6)0.7968 (4)0.201 (10)0.5
C3B0.74049 (15)0.6219 (5)0.85872 (9)0.0558 (8)
H3B0.7830760.6854140.8676380.067*
C2B0.68961 (15)0.7237 (5)0.83104 (9)0.0606 (9)
H2B0.6978870.8571120.8218770.073*
C12B0.78757 (16)0.1208 (5)0.91983 (9)0.0608 (9)
H12B0.7568270.0087850.9123850.073*
C13B0.84916 (17)0.1160 (5)0.94967 (9)0.0607 (9)
H13B0.8664460.0001850.9657410.073*
C14A0.0646 (2)0.2526 (8)0.79493 (12)0.0688 (10)
C1A0.12241 (14)0.3700 (5)0.82114 (8)0.0496 (8)
C2A0.15966 (14)0.2766 (5)0.85543 (8)0.0518 (8)
H2A0.1472940.1423940.8622410.062*
C3A0.21492 (14)0.3792 (5)0.87976 (8)0.0491 (8)
H3A0.2392070.3143240.9029380.059*
C4A0.23480 (14)0.5793 (5)0.86997 (8)0.0444 (7)
C5A0.29430 (14)0.6883 (5)0.89440 (8)0.0470 (8)
C6A0.39173 (14)0.6962 (5)0.94160 (8)0.0441 (7)
C7A0.44596 (13)0.5967 (5)0.97145 (7)0.0417 (7)
C8A0.50857 (15)0.6983 (4)0.98529 (8)0.0481 (8)
H8A0.5148560.8319330.9754910.058*
C9A0.43861 (14)0.3953 (4)0.98676 (8)0.0454 (7)
H9A0.3974220.3234110.9779240.054*
C11A0.19665 (15)0.6744 (5)0.83537 (8)0.0556 (8)
H11A0.2089670.8084270.8284290.067*
C10A0.14077 (15)0.5714 (5)0.81132 (9)0.0601 (9)
H10A0.1153640.6371380.7884950.072*
C13A0.38293 (15)0.8912 (5)0.92473 (9)0.0547 (8)
H13A0.4121821.0072950.9316640.066*
C12A0.32104 (15)0.8860 (5)0.89460 (9)0.0565 (8)
H12A0.3021300.9980730.8779460.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F20.108 (9)0.100 (5)0.070 (4)0.055 (5)0.012 (5)0.002 (4)
F30.079 (6)0.174 (11)0.053 (3)0.032 (7)0.032 (4)0.045 (4)
F10.075 (7)0.093 (6)0.170 (14)0.020 (5)0.059 (7)0.008 (7)
F50.079 (7)0.280 (17)0.103 (8)0.089 (8)0.040 (6)0.024 (10)
F60.090 (9)0.140 (8)0.282 (17)0.044 (6)0.069 (9)0.113 (10)
F40.105 (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)
F2A0.046 (4)0.182 (11)0.143 (10)0.022 (6)0.027 (6)0.061 (7)
F3A0.086 (8)0.048 (4)0.164 (9)0.002 (4)0.050 (8)0.005 (5)
F1A0.110 (7)0.128 (9)0.047 (3)0.027 (6)0.013 (4)0.002 (4)
F5A0.095 (9)0.218 (15)0.108 (5)0.091 (10)0.016 (6)0.053 (8)
F4A0.105 (8)0.119 (6)0.123 (10)0.008 (6)0.051 (6)0.036 (7)
F6A0.115 (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)
O10.0485 (12)0.0461 (13)0.0550 (13)0.0012 (11)0.0146 (11)0.0058 (11)
O1B0.0483 (13)0.0475 (13)0.0587 (13)0.0010 (11)0.0170 (11)0.0069 (11)
O1A0.0451 (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)
C70.0457 (18)0.044 (2)0.0496 (18)0.0091 (16)0.0241 (16)0.0057 (16)
C60.0488 (19)0.047 (2)0.0497 (19)0.0061 (17)0.0201 (16)0.0056 (17)
C50.0473 (19)0.049 (2)0.0531 (19)0.0082 (17)0.0173 (17)0.0068 (17)
C40.0454 (19)0.053 (2)0.0527 (19)0.0038 (17)0.0173 (17)0.0088 (17)
C110.058 (2)0.055 (2)0.073 (2)0.0158 (18)0.0179 (19)0.0032 (19)
C100.042 (2)0.081 (3)0.070 (2)0.0147 (19)0.0087 (18)0.013 (2)
C10.0444 (19)0.061 (2)0.0522 (19)0.0049 (17)0.0097 (16)0.0082 (17)
C140.056 (3)0.074 (3)0.057 (3)0.006 (2)0.002 (2)0.011 (2)
C130.069 (2)0.050 (2)0.061 (2)0.0033 (19)0.025 (2)0.0089 (17)
C120.071 (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)
C90.0477 (19)0.046 (2)0.0545 (19)0.0111 (16)0.0192 (16)0.0126 (16)
C80.0529 (19)0.0464 (19)0.060 (2)0.0066 (16)0.0254 (17)0.0145 (17)
C30.0441 (19)0.055 (2)0.066 (2)0.0086 (17)0.0065 (17)0.0008 (18)
C20.048 (2)0.054 (2)0.065 (2)0.0097 (17)0.0061 (18)0.0042 (18)
C14B0.055 (3)0.094 (4)0.064 (3)0.005 (3)0.004 (3)0.013 (3)
C1B0.045 (2)0.062 (2)0.059 (2)0.0035 (19)0.0114 (17)0.0139 (19)
C10B0.043 (2)0.072 (3)0.075 (2)0.0136 (19)0.0120 (19)0.020 (2)
C11B0.057 (2)0.055 (2)0.077 (2)0.0127 (18)0.025 (2)0.0055 (19)
C4B0.0447 (19)0.047 (2)0.0525 (19)0.0034 (16)0.0196 (16)0.0059 (16)
C5B0.054 (2)0.045 (2)0.055 (2)0.0033 (17)0.0260 (17)0.0043 (17)
C6B0.0494 (19)0.051 (2)0.0517 (19)0.0129 (17)0.0214 (17)0.0135 (17)
C7B0.0456 (19)0.052 (2)0.0503 (19)0.0109 (17)0.0199 (17)0.0111 (16)
C9B0.049 (2)0.054 (2)0.055 (2)0.0089 (17)0.0155 (17)0.0139 (17)
C8B0.060 (2)0.048 (2)0.063 (2)0.0060 (17)0.0241 (18)0.0152 (18)
F2B0.129 (13)0.27 (2)0.058 (6)0.106 (12)0.049 (8)0.046 (10)
F3B0.106 (7)0.074 (4)0.082 (5)0.033 (4)0.011 (5)0.001 (4)
F1B0.049 (5)0.114 (5)0.209 (17)0.010 (5)0.019 (8)0.014 (7)
F6B0.102 (7)0.157 (10)0.227 (18)0.033 (8)0.050 (9)0.115 (10)
F5B0.097 (9)0.172 (9)0.089 (6)0.015 (5)0.028 (6)0.046 (6)
F4B0.119 (14)0.41 (3)0.092 (7)0.161 (16)0.055 (9)0.057 (14)
C3B0.0424 (18)0.056 (2)0.065 (2)0.0076 (17)0.0090 (17)0.0003 (18)
C2B0.053 (2)0.054 (2)0.069 (2)0.0002 (18)0.0087 (18)0.0081 (18)
C12B0.067 (2)0.053 (2)0.066 (2)0.0059 (19)0.025 (2)0.0009 (19)
C13B0.073 (2)0.046 (2)0.068 (2)0.0045 (19)0.027 (2)0.0102 (18)
C14A0.056 (3)0.079 (3)0.061 (3)0.003 (3)0.002 (2)0.009 (3)
C1A0.0465 (18)0.052 (2)0.0472 (18)0.0025 (17)0.0087 (16)0.0060 (17)
C2A0.0511 (19)0.0460 (19)0.0550 (19)0.0035 (16)0.0101 (17)0.0105 (16)
C3A0.0496 (19)0.0449 (19)0.0477 (18)0.0037 (16)0.0059 (16)0.0101 (16)
C4A0.0411 (18)0.045 (2)0.0481 (18)0.0052 (15)0.0149 (15)0.0024 (16)
C5A0.0467 (19)0.048 (2)0.0477 (18)0.0022 (17)0.0155 (16)0.0044 (16)
C6A0.0441 (18)0.043 (2)0.0476 (18)0.0105 (16)0.0169 (16)0.0111 (16)
C7A0.0477 (19)0.0399 (18)0.0391 (17)0.0080 (15)0.0149 (15)0.0090 (14)
C8A0.0540 (19)0.0429 (19)0.0475 (18)0.0139 (16)0.0147 (16)0.0058 (15)
C9A0.0451 (18)0.044 (2)0.0474 (18)0.0162 (15)0.0145 (16)0.0083 (15)
C11A0.059 (2)0.051 (2)0.055 (2)0.0020 (17)0.0136 (18)0.0158 (17)
C10A0.058 (2)0.067 (2)0.050 (2)0.0126 (18)0.0074 (18)0.0125 (18)
C13A0.056 (2)0.045 (2)0.067 (2)0.0091 (17)0.0231 (18)0.0019 (18)
C12A0.057 (2)0.046 (2)0.070 (2)0.0040 (17)0.0236 (19)0.0096 (18)
Geometric parameters (Å, º) top
F2—F50.887 (15)C7—C61.449 (4)
F2—C141.318 (10)C6—C131.346 (4)
F2—F61.61 (2)C5—C121.352 (4)
F3—F60.60 (2)C5—C41.457 (4)
F3—C141.294 (10)C4—C31.387 (4)
F3—F41.698 (19)C4—C111.391 (4)
F1—F40.70 (2)C11—C101.384 (4)
F1—C141.274 (11)C10—C11.380 (4)
F1—F51.480 (16)C1—C21.379 (4)
F5—C141.282 (11)C1—C141.491 (4)
F6—C141.283 (12)C13—C121.406 (4)
F4—C141.308 (13)C12'—C13'1.405 (4)
F1'—F4'0.51 (3)C10'—C11'1.376 (4)
F1'—C14'1.331 (14)C9—C81.375 (3)
F2'—F5'0.60 (4)C3—C21.375 (4)
F2'—C14'1.231 (16)C14B—F4B1.210 (9)
F2'—F4'1.63 (2)C14B—F2B1.226 (9)
F3'—F6'0.51 (3)C14B—F5B1.305 (10)
F3'—C14'1.317 (16)C14B—F3B1.314 (8)
F4'—C14'1.255 (15)C14B—F1B1.322 (11)
F5'—C14'1.388 (18)C14B—F6B1.329 (10)
F6'—C14'1.297 (14)C14B—C1B1.493 (4)
F2A—F5A0.949 (12)C1B—C10B1.377 (4)
F2A—C14A1.264 (9)C1B—C2B1.383 (4)
F2A—F4A1.313 (12)C10B—C11B1.376 (4)
F3A—F6A0.81 (2)C11B—C4B1.394 (4)
F3A—C14A1.292 (11)C4B—C3B1.391 (4)
F3A—F5A1.508 (16)C4B—C5B1.450 (4)
F1A—F4A1.008 (12)C5B—C12B1.355 (4)
F1A—C14A1.350 (9)C6B—C13B1.350 (4)
F1A—F6A1.49 (2)C6B—C7B1.450 (4)
F5A—C14A1.308 (10)C7B—C9B1.397 (4)
F4A—C14A1.284 (8)C7B—C8B1.401 (4)
F6A—C14A1.268 (13)C9B—C8Bi1.373 (4)
O1'—C6'1.378 (3)F2B—F5B1.059 (16)
O1'—C5'1.380 (3)F2B—F6B1.127 (13)
O1—C51.373 (3)F3B—F4B1.24 (3)
O1—C61.382 (3)F3B—F6B1.32 (2)
O1B—C6B1.377 (3)F1B—F4B0.92 (3)
O1B—C5B1.379 (3)F1B—F5B1.439 (15)
O1A—C5A1.377 (3)C3B—C2B1.374 (4)
O1A—C6A1.377 (3)C12B—C13B1.403 (4)
C14'—C1'1.496 (4)C14A—C1A1.481 (4)
C1'—C2'1.381 (3)C1A—C2A1.377 (3)
C1'—C10'1.390 (4)C1A—C10A1.389 (4)
C2'—C3'1.374 (3)C2A—C3A1.376 (4)
C3'—C4'1.394 (4)C3A—C4A1.393 (4)
C4'—C11'1.397 (3)C4A—C11A1.395 (4)
C4'—C5'1.454 (4)C4A—C5A1.453 (4)
C5'—C12'1.348 (4)C5A—C12A1.353 (4)
C6'—C13'1.354 (4)C6A—C13A1.350 (4)
C6'—C7'1.452 (4)C6A—C7A1.445 (4)
C7'—C91.393 (3)C7A—C8A1.392 (3)
C7'—C8'1.396 (4)C7A—C9A1.400 (4)
C8'—C9'1.374 (4)C8A—C9Aii1.378 (3)
C9'—C71.391 (4)C11A—C10A1.381 (4)
C7—C81.402 (4)C13A—C12A1.413 (4)
F5—F2—C1467.9 (11)F1—C14—C1116.2 (7)
F5—F2—F6110.6 (17)F5—C14—C1113.9 (6)
C14—F2—F650.8 (7)F6—C14—C1114.9 (6)
F6—F3—C1475.5 (18)F3—C14—C1112.4 (5)
F6—F3—F4118 (2)F4—C14—C1111.3 (8)
C14—F3—F449.6 (6)F2—C14—C1110.7 (6)
F4—F1—C1476.8 (18)C6—C13—C12107.3 (3)
F4—F1—F5129 (2)C5—C12—C13107.7 (3)
C14—F1—F554.9 (6)C5'—C12'—C13'107.9 (3)
F2—F5—C1472.2 (13)C6'—C13'—C12'107.2 (3)
F2—F5—F1121.5 (18)C11'—C10'—C1'119.8 (3)
C14—F5—F154.4 (6)C10'—C11'—C4'120.9 (3)
F3—F6—C1477 (2)C8—C9—C7'120.9 (3)
F3—F6—F2127 (2)C9—C8—C7121.4 (3)
C14—F6—F252.7 (6)C2—C3—C4120.6 (3)
F1—F4—C1471.5 (18)C3—C2—C1121.0 (3)
F1—F4—F3112 (2)F4B—C14B—F2B129.7 (7)
C14—F4—F348.9 (6)F4B—C14B—F5B104.4 (11)
F4'—F1'—C14'70 (3)F2B—C14B—F5B49.3 (8)
F5'—F2'—C14'92 (4)F4B—C14B—F3B58.8 (14)
F5'—F2'—F4'136 (5)F2B—C14B—F3B108.7 (9)
C14'—F2'—F4'49.5 (9)F5B—C14B—F3B137.8 (7)
F6'—F3'—C14'77 (3)F4B—C14B—F1B42.5 (13)
F1'—F4'—C14'87 (4)F2B—C14B—F1B109.9 (9)
F1'—F4'—F2'130 (4)F5B—C14B—F1B66.4 (6)
C14'—F4'—F2'48.3 (9)F3B—C14B—F1B100.1 (7)
F2'—F5'—C14'62 (3)F4B—C14B—F6B109.9 (11)
F3'—F6'—C14'81 (3)F2B—C14B—F6B52.2 (7)
F5A—F2A—C14A70.8 (10)F5B—C14B—F6B99.1 (9)
F5A—F2A—F4A125.2 (14)F3B—C14B—F6B59.7 (10)
C14A—F2A—F4A59.7 (5)F1B—C14B—F6B132.8 (8)
F6A—F3A—C14A69.9 (14)F4B—C14B—C1B115.8 (6)
F6A—F3A—F5A121.4 (18)F2B—C14B—C1B114.1 (5)
C14A—F3A—F5A55.0 (5)F5B—C14B—C1B112.0 (6)
F4A—F1A—C14A64.1 (8)F3B—C14B—C1B110.1 (5)
F4A—F1A—F6A110.8 (13)F1B—C14B—C1B113.0 (7)
C14A—F1A—F6A52.8 (7)F6B—C14B—C1B114.0 (5)
F2A—F5A—C14A65.9 (9)C10B—C1B—C2B118.6 (3)
F2A—F5A—F3A113.0 (13)C10B—C1B—C14B121.3 (4)
C14A—F5A—F3A54.0 (7)C2B—C1B—C14B120.1 (4)
F1A—F4A—C14A71.0 (10)C11B—C10B—C1B121.1 (3)
F1A—F4A—F2A125.0 (15)C10B—C11B—C4B120.4 (3)
C14A—F4A—F2A58.2 (6)C3B—C4B—C11B118.3 (3)
F3A—F6A—C14A73.1 (15)C3B—C4B—C5B121.2 (3)
F3A—F6A—F1A124.0 (19)C11B—C4B—C5B120.4 (3)
C14A—F6A—F1A58.0 (8)C12B—C5B—O1B108.7 (3)
C6'—O1'—C5'107.3 (2)C12B—C5B—C4B134.0 (3)
C5—O1—C6107.3 (2)O1B—C5B—C4B117.3 (3)
C6B—O1B—C5B107.4 (2)C13B—C6B—O1B108.7 (3)
C5A—O1A—C6A107.4 (2)C13B—C6B—C7B134.9 (3)
F2'—C14'—F4'82.2 (13)O1B—C6B—C7B116.4 (3)
F2'—C14'—F6'124.0 (13)C9B—C7B—C8B117.4 (3)
F4'—C14'—F6'106.9 (11)C9B—C7B—C6B122.2 (3)
F2'—C14'—F3'106.3 (14)C8B—C7B—C6B120.4 (3)
F4'—C14'—F3'121.1 (12)C8Bi—C9B—C7B120.9 (3)
F6'—C14'—F3'22.3 (14)C9Bi—C8B—C7B121.7 (3)
F2'—C14'—F1'102.9 (13)F5B—F2B—F6B132.9 (16)
F4'—C14'—F1'22.6 (14)F5B—F2B—C14B69.2 (9)
F6'—C14'—F1'87.7 (12)F6B—F2B—C14B68.6 (8)
F3'—C14'—F1'105.9 (11)F4B—F3B—C14B56.4 (7)
F2'—C14'—F5'25.6 (17)F4B—F3B—F6B108.7 (9)
F4'—C14'—F5'105.7 (13)C14B—F3B—F6B60.7 (6)
F6'—C14'—F5'106.3 (14)F4B—F1B—C14B62.3 (12)
F3'—C14'—F5'85.4 (13)F4B—F1B—F5B112.8 (18)
F1'—C14'—F5'123.9 (12)C14B—F1B—F5B56.2 (6)
F2'—C14'—C1'114.5 (11)F2B—F6B—F3B115.1 (14)
F4'—C14'—C1'114.5 (10)F2B—F6B—C14B59.2 (7)
F6'—C14'—C1'111.0 (8)F3B—F6B—C14B59.6 (8)
F3'—C14'—C1'113.7 (7)F2B—F5B—C14B61.4 (7)
F1'—C14'—C1'112.6 (10)F2B—F5B—F1B112.5 (12)
F5'—C14'—C1'111.9 (12)C14B—F5B—F1B57.4 (7)
C2'—C1'—C10'119.7 (3)F1B—F4B—C14B75.2 (11)
C2'—C1'—C14'119.9 (3)F1B—F4B—F3B137.3 (16)
C10'—C1'—C14'120.4 (3)C14B—F4B—F3B64.8 (10)
C3'—C2'—C1'120.5 (3)C2B—C3B—C4B120.5 (3)
C2'—C3'—C4'120.7 (3)C3B—C2B—C1B121.0 (3)
C3'—C4'—C11'118.4 (3)C5B—C12B—C13B107.4 (3)
C3'—C4'—C5'122.1 (3)C6B—C13B—C12B107.8 (3)
C11'—C4'—C5'119.5 (3)F2A—C14A—F6A131.9 (8)
C12'—C5'—O1'108.7 (3)F2A—C14A—F4A62.0 (6)
C12'—C5'—C4'134.4 (3)F6A—C14A—F4A108.7 (9)
O1'—C5'—C4'116.8 (3)F2A—C14A—F3A108.4 (8)
C13'—C6'—O1'108.9 (3)F6A—C14A—F3A37.0 (11)
C13'—C6'—C7'133.8 (3)F4A—C14A—F3A128.3 (7)
O1'—C6'—C7'117.2 (3)F2A—C14A—F5A43.3 (6)
C9—C7'—C8'117.7 (3)F6A—C14A—F5A105.7 (10)
C9—C7'—C6'122.3 (3)F4A—C14A—F5A102.1 (7)
C8'—C7'—C6'120.0 (3)F3A—C14A—F5A70.9 (8)
C9'—C8'—C7'121.5 (3)F2A—C14A—F1A104.2 (7)
C8'—C9'—C7121.0 (3)F6A—C14A—F1A69.2 (11)
C9'—C7—C8117.5 (3)F4A—C14A—F1A44.9 (6)
C9'—C7—C6122.0 (3)F3A—C14A—F1A102.2 (8)
C8—C7—C6120.6 (3)F5A—C14A—F1A133.2 (6)
C13—C6—O1108.9 (3)F2A—C14A—C1A114.6 (5)
C13—C6—C7135.1 (3)F6A—C14A—C1A111.7 (7)
O1—C6—C7115.9 (3)F4A—C14A—C1A114.9 (5)
C12—C5—O1108.6 (3)F3A—C14A—C1A114.6 (5)
C12—C5—C4135.0 (3)F5A—C14A—C1A113.1 (6)
O1—C5—C4116.3 (3)F1A—C14A—C1A111.6 (5)
C3—C4—C11118.2 (3)C2A—C1A—C10A119.3 (3)
C3—C4—C5121.1 (3)C2A—C1A—C14A119.6 (3)
C11—C4—C5120.6 (3)C10A—C1A—C14A121.1 (3)
C10—C11—C4120.9 (3)C3A—C2A—C1A120.9 (3)
C1—C10—C11120.2 (3)C2A—C3A—C4A120.6 (3)
C2—C1—C10119.1 (3)C3A—C4A—C11A118.4 (3)
C2—C1—C14120.5 (3)C3A—C4A—C5A121.8 (3)
C10—C1—C14120.4 (3)C11A—C4A—C5A119.7 (3)
F1—C14—F570.8 (7)C12A—C5A—O1A108.8 (3)
F1—C14—F6122.8 (9)C12A—C5A—C4A134.7 (3)
F5—C14—F6109.5 (9)O1A—C5A—C4A116.5 (3)
F1—C14—F3106.9 (9)C13A—C6A—O1A109.1 (3)
F5—C14—F3128.6 (9)C13A—C6A—C7A134.1 (3)
F6—C14—F327.1 (11)O1A—C6A—C7A116.7 (3)
F1—C14—F431.6 (9)C8A—C7A—C9A117.7 (3)
F5—C14—F4101.2 (8)C8A—C7A—C6A120.3 (3)
F6—C14—F4104.8 (11)C9A—C7A—C6A122.1 (3)
F3—C14—F481.5 (9)C9Aii—C8A—C7A121.3 (3)
F1—C14—F2107.2 (8)C8Aii—C9A—C7A121.1 (3)
F5—C14—F239.9 (7)C10A—C11A—C4A120.6 (3)
F6—C14—F276.6 (9)C11A—C10A—C1A120.2 (3)
F3—C14—F2102.4 (8)C6A—C13A—C12A107.3 (3)
F4—C14—F2132.2 (7)C5A—C12A—C13A107.5 (3)
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+1, z+2.
 

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