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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o962.
Published online 2008 May 3. doi:  10.1107/S1600536808010635
PMCID: PMC2961548

3,3,4,4,5,5-Hexa­fluoro-1,2-bis­[5-(2-fluoro-4′-undecyl­oxybiphenyl-4-yl)-2-methyl-3-thien­yl]cyclo­pentene

Abstract

The title compound, C61H68F8O2S2, is a photochromic liquid crystal based on diaryl­ethene as photoswitchable unit. The F atoms connected to the benzene rings are disordered over two positions; the site-occupation factors refined to 0.830 (3)/0.170 (3). The mol­ecule adopts a photo-active anti­parallel conformation and the distance between the two reactive C atoms of the thio­phene rings is 3.448 (3) Å. The dihedral angles between the central cyclo­pentene ring and the adjacent thio­phene rings are 43.56 (3) and 48.58 (3)°. These structural elements exhibit a suitable geometry for photochromic behaviour in the crystalline state.

Related literature

For general background, see: Irie (2000 [triangle]); Tian & Yang (2004 [triangle]); Tian & Wang (2007 [triangle]); Frigoli et al. (2004 [triangle]). For related literature, see: Morimoto & Irie (2005 [triangle]); Kobatake et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o962-scheme1.jpg

Experimental

Crystal data

  • C61H68F8O2S2
  • M r = 1049.27
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o962-efi1.jpg
  • a = 10.2324 (15) Å
  • b = 10.9626 (16) Å
  • c = 24.468 (4) Å
  • α = 77.083 (7)°
  • β = 85.576 (10)°
  • γ = 89.924 (7)°
  • V = 2666.9 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 100 (2) K
  • 0.30 × 0.10 × 0.06 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.950, T max = 0.990
  • 66708 measured reflections
  • 15658 independent reflections
  • 13169 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.156
  • S = 1.05
  • 15658 reflections
  • 682 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 2.07 e Å−3
  • Δρmin = −0.76 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010635/hk2453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010635/hk2453Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Diarylethene molecules are known to be the most promising organic photochromic material for three-dimensional optical memory and molecular switches (Irie, 2000; Tian & Yang, 2004; Tian & Wang, 2007). The title compound, (I), was the first photochromic liquid crystal based on diarylethene material (Frigoli et al., 2004). We have shown that photochromic behaviour occurs very efficiently in solution and in the liquid crystalline state.

The molecule of the title compound, (I), (Fig. 1) adopts an antiparallel conformation. When the crystal structure was solved, the F atoms connected to the phenyl groups were found to be disordered.

The C5A···C5B [3.448 (2) Å] distance between the carbons bearing the methyl groups of the thiophene rings indicates that the photochromic reaction can occur in the crystalline state as well (Morimoto & Irie, 2005; Kobatake et al., 2007). The dihedral angles between the central cyclopentene ring: A (C1A-C3A/C2B/C3B) and the adjacent thiophene rings: B (S1A/C4A-C7A) and C (S1B/C4B-C7B) are 43.56 (3)° and 48.58 (3)°, respectively.

Experimental

The synthesis of (I) was reported, previously (Frigoli et al., 2004). The needle-like crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a cyclohexane solution.

Refinement

When the crystal structure was solved, the F atoms connected to the phenyl groups were found to be disordered. They were each modelled with disorder over two positions and their occupancies were refined as 0.830 (3) (for F4A), 0.170 (3) (for F5A), 0.790 (3) (for F4B) and 0.210 (3) (for F5B). The C-F bonds between the F atoms and the phenyl groups with the lowest site occupancy were restrained to be 1.34 Å. H atoms were positioned geometrically, with C-H = 0.95, 0.99 and 0.98 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme only for the most relevant atoms. Displacement ellipsoids are drawn at the 50% probability level. Only the major component is shown, for clarity.
Fig. 2.
Supplementary figure.

Crystal data

C61H68F8O2S2Z = 2
Mr = 1049.27F000 = 1108
Triclinic, P1Dx = 1.307 Mg m3
Hall symbol: -P 1Melting point: 372.8 K
a = 10.2324 (15) ÅMo Kα radiation λ = 0.71073 Å
b = 10.9626 (16) ÅCell parameters from 9287 reflections
c = 24.468 (4) Åθ = 2.5–30.1º
α = 77.083 (7)ºµ = 0.17 mm1
β = 85.576 (10)ºT = 100 (2) K
γ = 89.924 (7)ºNeedle, light blue
V = 2666.9 (7) Å30.30 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer15658 independent reflections
Radiation source: fine-focus sealed tube13169 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
Detector resolution: 512x512 pixels mm-1θmax = 30.1º
T = 100(2) Kθmin = 0.9º
[var phi] and ω scansh = −14→14
Absorption correction: multi-scan(SADABS; Bruker, 2004)k = −15→15
Tmin = 0.950, Tmax = 0.990l = −34→34
66708 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.156  w = 1/[σ2(Fo2) + (0.0897P)2 + 1.5953P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
15658 reflectionsΔρmax = 2.07 e Å3
682 parametersΔρmin = −0.76 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S1A0.26666 (4)0.32993 (3)0.130497 (14)0.01950 (9)
S1B0.36216 (4)0.54474 (3)−0.097570 (15)0.01946 (9)
F1A0.09780 (15)−0.07874 (14)−0.02856 (6)0.0572 (4)
F2A0.17004 (15)−0.06215 (11)0.06498 (5)0.0484 (3)
F3A0.37487 (13)−0.06276 (10)0.03551 (5)0.0424 (3)
F1B0.29892 (17)−0.12047 (13)−0.05048 (6)0.0576 (4)
F2B0.33540 (19)0.09210 (13)−0.11450 (6)0.0696 (5)
F3B0.12612 (17)0.11540 (11)−0.10413 (6)0.0586 (4)
C1A0.22190 (18)−0.03564 (15)−0.03392 (7)0.0274 (3)
C2A0.25788 (17)−0.00932 (14)0.02232 (7)0.0245 (3)
C3A0.26556 (14)0.13067 (13)0.01336 (6)0.0180 (3)
C4A0.28225 (14)0.18778 (13)0.06092 (6)0.0179 (3)
C5A0.21719 (14)0.29210 (14)0.07076 (6)0.0189 (3)
C6A0.36934 (14)0.13842 (13)0.10326 (6)0.0185 (3)
H6A0.42020.06600.10300.022*
C7A0.37236 (14)0.20524 (13)0.14403 (6)0.0176 (3)
C8A0.44329 (14)0.17614 (14)0.19500 (6)0.0174 (3)
C9A0.52927 (16)0.07574 (17)0.20384 (6)0.0257 (3)
H9A0.54610.03000.17540.031*
C10A0.59008 (15)0.04217 (16)0.25338 (6)0.0237 (3)
H10A0.6466−0.02760.25820.028*0.830 (3)
F5A0.6357 (6)−0.0878 (5)0.2634 (2)0.0272 (16)0.170 (3)
C11A0.57218 (14)0.10607 (13)0.29668 (6)0.0173 (3)
C12A0.48413 (16)0.20477 (13)0.28672 (6)0.0204 (3)
H12A0.46640.24980.31540.024*0.170 (3)
F4A0.45068 (12)0.26923 (11)0.32778 (5)0.0257 (3)0.830 (3)
C13A0.42129 (16)0.24093 (13)0.23775 (6)0.0206 (3)
H13A0.36340.30960.23330.025*
C14A0.64219 (14)0.06645 (13)0.34849 (6)0.0165 (2)
C15A0.76122 (14)0.00391 (14)0.34597 (6)0.0182 (3)
H15A0.7986−0.00560.31040.022*
C16A0.82662 (14)−0.04480 (13)0.39369 (6)0.0170 (3)
H16A0.9063−0.08820.39070.020*
C17A0.77412 (13)−0.02928 (12)0.44576 (6)0.0155 (2)
C18A0.65849 (14)0.03770 (13)0.44916 (6)0.0171 (3)
H18A0.62420.05120.48450.021*
C19A0.59345 (14)0.08458 (13)0.40136 (6)0.0172 (3)
H19A0.51480.12960.40440.021*
O20A0.82961 (10)−0.07467 (10)0.49529 (4)0.0181 (2)
C21A0.94176 (14)−0.15368 (13)0.49318 (6)0.0168 (2)
H21A1.0154−0.10600.46920.020*
H21B0.9195−0.22580.47720.020*
C22A0.97981 (14)−0.19882 (13)0.55275 (6)0.0167 (2)
H22A0.9043−0.24440.57620.020*
H22B1.0000−0.12540.56810.020*
C23A1.09815 (14)−0.28464 (13)0.55689 (6)0.0176 (3)
H23A1.0773−0.35980.54290.021*
H23B1.1733−0.24030.53270.021*
C24A1.13636 (14)−0.32495 (13)0.61733 (6)0.0170 (2)
H24A1.0599−0.36740.64130.020*
H24B1.1571−0.24920.63090.020*
C25A1.25329 (14)−0.41233 (14)0.62483 (6)0.0187 (3)
H25A1.2339−0.48800.61090.022*
H25B1.3310−0.36960.60200.022*
C26A1.28462 (14)−0.45134 (14)0.68623 (6)0.0190 (3)
H26A1.2073−0.49590.70860.023*
H26B1.3001−0.37500.70030.023*
C27A1.40379 (16)−0.53541 (16)0.69600 (6)0.0236 (3)
H27A1.3857−0.61490.68500.028*
H27B1.4799−0.49390.67150.028*
C28A1.43891 (15)−0.56448 (16)0.75704 (6)0.0241 (3)
H28A1.4302−0.48710.77150.029*
H28B1.3748−0.62680.77970.029*
C29A1.57607 (19)−0.6145 (2)0.76576 (8)0.0346 (4)
H29A1.6405−0.55280.74290.041*
H29B1.5848−0.69260.75200.041*
C30A1.6090 (2)−0.6412 (2)0.82714 (8)0.0358 (4)
H30A1.5893−0.56600.84220.043*
H30B1.5512−0.71020.84900.043*
C31A1.7497 (2)−0.6764 (2)0.83619 (9)0.0418 (5)
H31A1.7675−0.75620.82560.063*
H31B1.7647−0.68460.87590.063*
H31C1.8082−0.61110.81300.063*
C32A0.11312 (16)0.36790 (16)0.03948 (6)0.0242 (3)
H32A0.15410.43840.01160.036*
H32B0.05300.39970.06600.036*
H32C0.06420.31510.02040.036*
C2B0.23353 (19)0.09292 (15)−0.07575 (7)0.0270 (3)
C3B0.25741 (14)0.18662 (13)−0.04149 (6)0.0177 (3)
C4B0.27481 (14)0.31989 (13)−0.06856 (5)0.0166 (3)
C5B0.37792 (14)0.39256 (13)−0.06085 (6)0.0175 (3)
C6B0.18441 (14)0.38799 (13)−0.10536 (6)0.0172 (3)
H6B0.10920.3508−0.11580.021*
C7B0.21740 (14)0.51230 (13)−0.12398 (6)0.0172 (3)
C8B0.14597 (14)0.61043 (13)−0.16030 (6)0.0172 (3)
C9B0.16133 (15)0.73655 (14)−0.15960 (6)0.0221 (3)
H9B0.22220.7607−0.13640.026*
C10B0.08821 (15)0.82686 (14)−0.19256 (7)0.0215 (3)
H10B0.10020.9120−0.19120.026*0.790 (3)
F5B0.1051 (5)0.9398 (4)−0.1872 (2)0.0331 (15)0.210 (3)
C11B−0.00246 (14)0.79714 (13)−0.22761 (6)0.0165 (2)
C12B−0.01302 (14)0.67084 (13)−0.22799 (6)0.0167 (3)
H12B−0.07230.6469−0.25190.020*0.210 (3)
F4B−0.10195 (11)0.63417 (10)−0.25907 (5)0.0214 (3)0.790 (3)
C13B0.05760 (14)0.57843 (13)−0.19565 (6)0.0174 (3)
H13B0.04610.4935−0.19740.021*
C14B−0.08765 (13)0.89257 (13)−0.25938 (6)0.0161 (2)
C15B−0.15027 (14)0.98035 (13)−0.23334 (6)0.0176 (3)
H15B−0.13450.9813−0.19570.021*
C16B−0.23517 (14)1.06622 (13)−0.26184 (6)0.0185 (3)
H16B−0.27821.1244−0.24340.022*
C17B−0.25764 (14)1.06759 (13)−0.31750 (6)0.0169 (3)
C18B−0.19397 (14)0.98259 (13)−0.34459 (6)0.0182 (3)
H18B−0.20690.9841−0.38280.022*
C19B−0.11097 (14)0.89513 (13)−0.31500 (6)0.0183 (3)
H19B−0.06930.8358−0.33320.022*
O20B−0.34398 (11)1.15515 (10)−0.34106 (4)0.0201 (2)
C21B−0.36989 (14)1.16370 (13)−0.39837 (6)0.0181 (3)
H21C−0.39331.0802−0.40420.022*
H21D−0.29151.1962−0.42370.022*
C22B−0.48311 (14)1.25237 (13)−0.41046 (6)0.0182 (3)
H22C−0.46151.3320−0.40030.022*
H22D−0.56191.2155−0.38640.022*
C23B−0.51473 (14)1.27997 (13)−0.47178 (6)0.0177 (3)
H23C−0.53541.2004−0.48230.021*
H23D−0.43671.3184−0.49590.021*
C24B−0.63045 (14)1.36794 (13)−0.48255 (6)0.0175 (3)
H24C−0.70831.3286−0.45860.021*
H24D−0.61001.4465−0.47110.021*
C25B−0.66411 (14)1.39987 (13)−0.54375 (6)0.0184 (3)
H25C−0.68751.3217−0.55490.022*
H25D−0.58571.4371−0.56790.022*
C26B−0.77763 (14)1.49103 (13)−0.55398 (6)0.0180 (3)
H26C−0.85711.4519−0.53120.022*
H26D−0.75601.5673−0.54100.022*
C27B−0.80802 (14)1.52863 (13)−0.61557 (6)0.0186 (3)
H27C−0.82881.4522−0.62860.022*
H27D−0.72871.5683−0.63830.022*
C28B−0.92223 (14)1.61898 (13)−0.62599 (6)0.0182 (3)
H28C−1.00071.5813−0.60190.022*
H28D−0.89971.6975−0.61490.022*
C29B−0.95494 (15)1.64984 (13)−0.68731 (6)0.0185 (3)
H29C−0.98231.5718−0.69750.022*
H29D−0.87481.6823−0.71140.022*
C30B−1.06341 (15)1.74599 (14)−0.69963 (6)0.0206 (3)
H30C−1.14281.7152−0.67460.025*
H30D−1.03481.8254−0.69100.025*
C31B−1.09804 (17)1.77157 (15)−0.76061 (7)0.0256 (3)
H31D−1.01971.8015−0.78560.038*
H31E−1.16581.8354−0.76650.038*
H31F−1.13091.6942−0.76890.038*
C32B0.49542 (15)0.35625 (14)−0.02802 (6)0.0215 (3)
H32D0.47690.36790.01040.032*
H32E0.57080.4089−0.04620.032*
H32F0.51530.2682−0.02680.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.02037 (17)0.02434 (17)0.01362 (15)0.00758 (13)−0.00211 (12)−0.00369 (12)
S1B0.01891 (17)0.01874 (16)0.01937 (16)0.00367 (12)−0.00647 (12)0.00022 (12)
F1A0.0544 (8)0.0580 (8)0.0514 (8)−0.0252 (7)−0.0263 (7)0.0115 (6)
F2A0.0741 (9)0.0307 (6)0.0353 (6)−0.0165 (6)0.0131 (6)−0.0021 (5)
F3A0.0556 (7)0.0267 (5)0.0529 (7)0.0245 (5)−0.0357 (6)−0.0153 (5)
F1B0.0931 (11)0.0451 (7)0.0451 (7)0.0445 (8)−0.0282 (7)−0.0250 (6)
F2B0.1148 (14)0.0413 (7)0.0533 (8)−0.0194 (8)0.0472 (9)−0.0302 (6)
F3B0.0945 (11)0.0276 (6)0.0606 (8)0.0042 (6)−0.0611 (8)−0.0060 (5)
C1A0.0342 (9)0.0187 (7)0.0315 (8)0.0055 (6)−0.0124 (7)−0.0070 (6)
C2A0.0314 (8)0.0183 (6)0.0227 (7)0.0048 (6)−0.0072 (6)−0.0006 (5)
C3A0.0196 (6)0.0172 (6)0.0168 (6)0.0059 (5)−0.0044 (5)−0.0020 (5)
C4A0.0197 (6)0.0197 (6)0.0124 (6)0.0046 (5)−0.0030 (5)0.0006 (5)
C5A0.0188 (6)0.0237 (7)0.0127 (6)0.0059 (5)−0.0021 (5)−0.0009 (5)
C6A0.0201 (6)0.0196 (6)0.0144 (6)0.0052 (5)−0.0041 (5)0.0003 (5)
C7A0.0159 (6)0.0208 (6)0.0139 (6)0.0033 (5)−0.0017 (5)0.0008 (5)
C8A0.0146 (6)0.0217 (6)0.0143 (6)0.0007 (5)−0.0019 (5)−0.0001 (5)
C9A0.0257 (8)0.0368 (8)0.0166 (6)0.0147 (6)−0.0060 (6)−0.0091 (6)
C10A0.0217 (7)0.0325 (8)0.0180 (6)0.0135 (6)−0.0058 (5)−0.0062 (6)
F5A0.034 (3)0.023 (3)0.030 (3)0.018 (2)−0.019 (2)−0.011 (2)
C11A0.0148 (6)0.0200 (6)0.0156 (6)−0.0008 (5)−0.0034 (5)−0.0002 (5)
C12A0.0268 (7)0.0165 (6)0.0192 (6)0.0022 (5)−0.0075 (5)−0.0048 (5)
F4A0.0337 (7)0.0251 (6)0.0229 (6)0.0124 (5)−0.0112 (5)−0.0126 (4)
C13A0.0258 (7)0.0164 (6)0.0200 (6)0.0033 (5)−0.0088 (5)−0.0024 (5)
C14A0.0154 (6)0.0165 (6)0.0167 (6)−0.0012 (5)−0.0044 (5)−0.0005 (5)
C15A0.0156 (6)0.0236 (6)0.0146 (6)0.0011 (5)−0.0024 (5)−0.0021 (5)
C16A0.0148 (6)0.0201 (6)0.0156 (6)0.0022 (5)−0.0030 (5)−0.0020 (5)
C17A0.0151 (6)0.0156 (6)0.0150 (6)−0.0005 (5)−0.0046 (5)−0.0007 (4)
C18A0.0160 (6)0.0180 (6)0.0169 (6)0.0005 (5)−0.0017 (5)−0.0028 (5)
C19A0.0147 (6)0.0171 (6)0.0192 (6)0.0007 (5)−0.0035 (5)−0.0019 (5)
O20A0.0182 (5)0.0216 (5)0.0140 (4)0.0049 (4)−0.0047 (4)−0.0016 (4)
C21A0.0167 (6)0.0174 (6)0.0160 (6)0.0027 (5)−0.0041 (5)−0.0020 (5)
C22A0.0169 (6)0.0172 (6)0.0151 (6)0.0009 (5)−0.0040 (5)−0.0006 (5)
C23A0.0179 (6)0.0179 (6)0.0166 (6)0.0017 (5)−0.0040 (5)−0.0023 (5)
C24A0.0160 (6)0.0187 (6)0.0159 (6)0.0025 (5)−0.0037 (5)−0.0024 (5)
C25A0.0178 (6)0.0205 (6)0.0176 (6)0.0043 (5)−0.0027 (5)−0.0033 (5)
C26A0.0173 (6)0.0216 (6)0.0175 (6)0.0047 (5)−0.0028 (5)−0.0030 (5)
C27A0.0217 (7)0.0314 (8)0.0176 (6)0.0118 (6)−0.0048 (5)−0.0042 (6)
C28A0.0187 (7)0.0342 (8)0.0184 (6)0.0087 (6)−0.0040 (5)−0.0026 (6)
C29A0.0329 (9)0.0446 (10)0.0266 (8)0.0156 (8)−0.0069 (7)−0.0072 (7)
C30A0.0392 (10)0.0419 (10)0.0244 (8)0.0086 (8)−0.0034 (7)−0.0032 (7)
C31A0.0403 (11)0.0533 (12)0.0333 (10)0.0103 (9)−0.0107 (8)−0.0103 (9)
C32A0.0245 (7)0.0315 (8)0.0166 (6)0.0146 (6)−0.0045 (5)−0.0046 (6)
C2B0.0416 (9)0.0225 (7)0.0182 (7)0.0036 (6)−0.0067 (6)−0.0059 (5)
C3B0.0199 (6)0.0182 (6)0.0154 (6)0.0059 (5)−0.0039 (5)−0.0036 (5)
C4B0.0198 (6)0.0180 (6)0.0118 (5)0.0072 (5)−0.0032 (5)−0.0025 (4)
C5B0.0196 (6)0.0186 (6)0.0139 (6)0.0067 (5)−0.0031 (5)−0.0019 (5)
C6B0.0184 (6)0.0199 (6)0.0131 (5)0.0053 (5)−0.0045 (5)−0.0021 (5)
C7B0.0174 (6)0.0197 (6)0.0139 (6)0.0053 (5)−0.0042 (5)−0.0017 (5)
C8B0.0168 (6)0.0194 (6)0.0135 (6)0.0055 (5)−0.0027 (5)0.0007 (5)
C9B0.0220 (7)0.0207 (6)0.0228 (7)0.0021 (5)−0.0109 (5)−0.0001 (5)
C10B0.0214 (7)0.0171 (6)0.0245 (7)0.0017 (5)−0.0083 (5)0.0007 (5)
F5B0.035 (3)0.013 (2)0.052 (3)0.0023 (17)−0.022 (2)−0.0014 (19)
C11B0.0154 (6)0.0173 (6)0.0147 (6)0.0029 (5)−0.0020 (5)0.0015 (5)
C12B0.0162 (6)0.0201 (6)0.0136 (5)0.0049 (5)−0.0037 (5)−0.0027 (5)
F4B0.0238 (6)0.0208 (6)0.0222 (6)0.0055 (4)−0.0122 (4)−0.0069 (4)
C13B0.0185 (6)0.0176 (6)0.0157 (6)0.0057 (5)−0.0031 (5)−0.0025 (5)
C14B0.0143 (6)0.0162 (6)0.0155 (6)0.0018 (5)−0.0026 (5)0.0018 (5)
C15B0.0193 (6)0.0158 (6)0.0167 (6)0.0010 (5)−0.0049 (5)−0.0003 (5)
C16B0.0202 (6)0.0142 (6)0.0209 (6)0.0030 (5)−0.0048 (5)−0.0022 (5)
C17B0.0149 (6)0.0143 (6)0.0195 (6)0.0014 (5)−0.0050 (5)0.0016 (5)
C18B0.0165 (6)0.0201 (6)0.0157 (6)0.0033 (5)−0.0024 (5)0.0011 (5)
C19B0.0168 (6)0.0204 (6)0.0156 (6)0.0048 (5)−0.0008 (5)0.0004 (5)
O20B0.0224 (5)0.0175 (5)0.0195 (5)0.0068 (4)−0.0081 (4)−0.0003 (4)
C21B0.0175 (6)0.0166 (6)0.0194 (6)0.0020 (5)−0.0071 (5)−0.0005 (5)
C22B0.0165 (6)0.0167 (6)0.0200 (6)0.0032 (5)−0.0064 (5)0.0007 (5)
C23B0.0166 (6)0.0153 (6)0.0206 (6)0.0028 (5)−0.0065 (5)−0.0011 (5)
C24B0.0158 (6)0.0162 (6)0.0198 (6)0.0029 (5)−0.0063 (5)−0.0008 (5)
C25B0.0170 (6)0.0174 (6)0.0204 (6)0.0029 (5)−0.0068 (5)−0.0014 (5)
C26B0.0165 (6)0.0171 (6)0.0195 (6)0.0018 (5)−0.0061 (5)−0.0005 (5)
C27B0.0177 (6)0.0176 (6)0.0199 (6)0.0029 (5)−0.0073 (5)−0.0010 (5)
C28B0.0179 (6)0.0181 (6)0.0181 (6)0.0029 (5)−0.0065 (5)−0.0014 (5)
C29B0.0210 (7)0.0153 (6)0.0194 (6)0.0030 (5)−0.0077 (5)−0.0019 (5)
C30B0.0219 (7)0.0192 (6)0.0204 (6)0.0047 (5)−0.0082 (5)−0.0016 (5)
C31B0.0314 (8)0.0222 (7)0.0237 (7)0.0061 (6)−0.0138 (6)−0.0022 (6)
C32B0.0212 (7)0.0218 (7)0.0214 (7)0.0068 (5)−0.0080 (5)−0.0028 (5)

Geometric parameters (Å, °)

S1A—C5A1.7176 (15)C31A—H31A0.9800
S1A—C7A1.7311 (14)C31A—H31B0.9800
S1B—C5B1.7228 (14)C31A—H31C0.9800
S1B—C7B1.7292 (15)C32A—H32A0.9800
F1A—C1A1.342 (2)C32A—H32B0.9800
F2A—C2A1.349 (2)C32A—H32C0.9800
F3A—C2A1.3616 (19)C2B—C3B1.495 (2)
F1B—C1A1.329 (2)C3B—C4B1.4680 (19)
F2B—C2B1.355 (2)C4B—C5B1.372 (2)
F3B—C2B1.339 (2)C4B—C6B1.4316 (18)
C1A—C2A1.539 (2)C5B—C32B1.5014 (19)
C1A—C2B1.544 (2)C6B—C7B1.371 (2)
C2A—C3A1.502 (2)C6B—H6B0.9500
C3A—C3B1.3540 (19)C7B—C8B1.4669 (18)
C3A—C4A1.460 (2)C8B—C13B1.395 (2)
C4A—C5A1.380 (2)C8B—C9B1.396 (2)
C4A—C6A1.4320 (18)C9B—C10B1.3874 (19)
C5A—C32A1.4999 (19)C9B—H9B0.9500
C6A—C7A1.365 (2)C10B—F5B1.287 (5)
C6A—H6A0.9500C10B—C11B1.397 (2)
C7A—C8A1.4645 (19)C10B—H10B0.9500
C8A—C13A1.395 (2)C11B—C12B1.391 (2)
C8A—C9A1.397 (2)C11B—C14B1.4822 (18)
C9A—C10A1.381 (2)C12B—F4B1.3463 (18)
C9A—H9A0.9500C12B—C13B1.3793 (18)
C10A—C11A1.396 (2)C12B—H12B0.9500
C10A—F5A1.473 (5)C13B—H13B0.9500
C10A—H10A0.9500C14B—C19B1.3939 (19)
C11A—C12A1.398 (2)C14B—C15B1.397 (2)
C11A—C14A1.4840 (18)C15B—C16B1.3874 (18)
C12A—F4A1.3745 (18)C15B—H15B0.9500
C12A—C13A1.383 (2)C16B—C17B1.395 (2)
C12A—H12A0.9500C16B—H16B0.9500
C13A—H13A0.9500C17B—O20B1.3649 (16)
C14A—C15A1.401 (2)C17B—C18B1.393 (2)
C14A—C19A1.406 (2)C18B—C19B1.3953 (18)
C15A—C16A1.3918 (18)C18B—H18B0.9500
C15A—H15A0.9500C19B—H19B0.9500
C16A—C17A1.3898 (19)O20B—C21B1.4295 (17)
C16A—H16A0.9500C21B—C22B1.5152 (19)
C17A—O20A1.3691 (16)C21B—H21C0.9900
C17A—C18A1.3985 (19)C21B—H21D0.9900
C18A—C19A1.3876 (19)C22B—C23B1.523 (2)
C18A—H18A0.9500C22B—H22C0.9900
C19A—H19A0.9500C22B—H22D0.9900
O20A—C21A1.4415 (17)C23B—C24B1.5274 (19)
C21A—C22A1.5118 (18)C23B—H23C0.9900
C21A—H21A0.9900C23B—H23D0.9900
C21A—H21B0.9900C24B—C25B1.5260 (19)
C22A—C23A1.5281 (19)C24B—H24C0.9900
C22A—H22A0.9900C24B—H24D0.9900
C22A—H22B0.9900C25B—C26B1.5299 (19)
C23A—C24A1.5270 (19)C25B—H25C0.9900
C23A—H23A0.9900C25B—H25D0.9900
C23A—H23B0.9900C26B—C27B1.5269 (19)
C24A—C25A1.5281 (19)C26B—H26C0.9900
C24A—H24A0.9900C26B—H26D0.9900
C24A—H24B0.9900C27B—C28B1.5303 (19)
C25A—C26A1.526 (2)C27B—H27C0.9900
C25A—H25A0.9900C27B—H27D0.9900
C25A—H25B0.9900C28B—C29B1.5256 (19)
C26A—C27A1.529 (2)C28B—H28C0.9900
C26A—H26A0.9900C28B—H28D0.9900
C26A—H26B0.9900C29B—C30B1.5297 (19)
C27A—C28A1.527 (2)C29B—H29C0.9900
C27A—H27A0.9900C29B—H29D0.9900
C27A—H27B0.9900C30B—C31B1.525 (2)
C28A—C29A1.519 (2)C30B—H30C0.9900
C28A—H28A0.9900C30B—H30D0.9900
C28A—H28B0.9900C31B—H31D0.9800
C29A—C30A1.528 (3)C31B—H31E0.9800
C29A—H29A0.9900C31B—H31F0.9800
C29A—H29B0.9900C32B—H32D0.9800
C30A—C31A1.509 (3)C32B—H32E0.9800
C30A—H30A0.9900C32B—H32F0.9800
C30A—H30B0.9900
C5A—S1A—C7A93.53 (7)H32A—C32A—H32B109.5
C5B—S1B—C7B93.16 (7)C5A—C32A—H32C109.5
F1B—C1A—F1A107.96 (16)H32A—C32A—H32C109.5
F1B—C1A—C2A112.29 (14)H32B—C32A—H32C109.5
F1A—C1A—C2A109.58 (16)F3B—C2B—F2B106.49 (16)
F1B—C1A—C2B112.38 (16)F3B—C2B—C3B113.45 (14)
F1A—C1A—C2B109.83 (14)F2B—C2B—C3B110.76 (15)
C2A—C1A—C2B104.78 (13)F3B—C2B—C1A110.70 (15)
F2A—C2A—F3A105.95 (14)F2B—C2B—C1A109.43 (15)
F2A—C2A—C3A112.71 (14)C3B—C2B—C1A106.02 (13)
F3A—C2A—C3A111.58 (14)C3A—C3B—C4B128.12 (13)
F2A—C2A—C1A111.51 (15)C3A—C3B—C2B111.42 (13)
F3A—C2A—C1A109.31 (14)C4B—C3B—C2B120.40 (12)
C3A—C2A—C1A105.84 (12)C5B—C4B—C6B112.97 (12)
C3B—C3A—C4A129.04 (13)C5B—C4B—C3B123.82 (12)
C3B—C3A—C2A111.08 (13)C6B—C4B—C3B123.21 (13)
C4A—C3A—C2A119.87 (12)C4B—C5B—C32B129.58 (13)
C5A—C4A—C6A112.67 (13)C4B—C5B—S1B110.46 (10)
C5A—C4A—C3A125.03 (13)C32B—C5B—S1B119.94 (11)
C6A—C4A—C3A122.30 (13)C7B—C6B—C4B113.19 (13)
C4A—C5A—C32A130.37 (14)C7B—C6B—H6B123.4
C4A—C5A—S1A110.23 (10)C4B—C6B—H6B123.4
C32A—C5A—S1A119.35 (11)C6B—C7B—C8B128.28 (13)
C7A—C6A—C4A113.68 (13)C6B—C7B—S1B110.20 (10)
C7A—C6A—H6A123.2C8B—C7B—S1B121.51 (11)
C4A—C6A—H6A123.2C13B—C8B—C9B118.34 (12)
C6A—C7A—C8A127.79 (13)C13B—C8B—C7B120.01 (13)
C6A—C7A—S1A109.87 (10)C9B—C8B—C7B121.63 (13)
C8A—C7A—S1A122.17 (11)C10B—C9B—C8B120.40 (14)
C13A—C8A—C9A117.77 (13)C10B—C9B—H9B119.8
C13A—C8A—C7A121.78 (13)C8B—C9B—H9B119.8
C9A—C8A—C7A120.30 (14)F5B—C10B—C9B115.8 (2)
C10A—C9A—C8A120.85 (15)F5B—C10B—C11B121.7 (2)
C10A—C9A—H9A119.6C9B—C10B—C11B122.41 (14)
C8A—C9A—H9A119.6F5B—C10B—H10B3.9
C9A—C10A—C11A122.98 (14)C9B—C10B—H10B118.8
C9A—C10A—F5A112.0 (3)C11B—C10B—H10B118.8
C11A—C10A—F5A121.9 (3)C12B—C11B—C10B115.45 (12)
C9A—C10A—H10A118.5C12B—C11B—C14B122.25 (13)
C11A—C10A—H10A118.5C10B—C11B—C14B122.19 (13)
F5A—C10A—H10A19.0F4B—C12B—C13B117.17 (13)
C10A—C11A—C12A114.57 (13)F4B—C12B—C11B118.96 (12)
C10A—C11A—C14A120.29 (13)C13B—C12B—C11B123.77 (13)
C12A—C11A—C14A125.12 (14)F4B—C12B—H12B3.5
F4A—C12A—C13A115.65 (13)C13B—C12B—H12B118.1
F4A—C12A—C11A120.24 (13)C11B—C12B—H12B118.1
C13A—C12A—C11A124.05 (14)C12B—C13B—C8B119.62 (13)
F4A—C12A—H12A3.4C12B—C13B—H13B120.2
C13A—C12A—H12A118.0C8B—C13B—H13B120.2
C11A—C12A—H12A118.0C19B—C14B—C15B118.22 (12)
C12A—C13A—C8A119.74 (14)C19B—C14B—C11B121.43 (13)
C12A—C13A—H13A120.1C15B—C14B—C11B120.32 (13)
C8A—C13A—H13A120.1C16B—C15B—C14B120.78 (13)
C15A—C14A—C19A117.19 (12)C16B—C15B—H15B119.6
C15A—C14A—C11A119.32 (13)C14B—C15B—H15B119.6
C19A—C14A—C11A123.46 (13)C15B—C16B—C17B120.35 (13)
C16A—C15A—C14A122.32 (13)C15B—C16B—H16B119.8
C16A—C15A—H15A118.8C17B—C16B—H16B119.8
C14A—C15A—H15A118.8O20B—C17B—C18B125.06 (13)
C17A—C16A—C15A119.33 (13)O20B—C17B—C16B115.21 (13)
C17A—C16A—H16A120.3C18B—C17B—C16B119.73 (12)
C15A—C16A—H16A120.3C17B—C18B—C19B119.25 (13)
O20A—C17A—C16A124.03 (12)C17B—C18B—H18B120.4
O20A—C17A—C18A116.43 (12)C19B—C18B—H18B120.4
C16A—C17A—C18A119.54 (12)C14B—C19B—C18B121.65 (13)
C19A—C18A—C17A120.54 (13)C14B—C19B—H19B119.2
C19A—C18A—H18A119.7C18B—C19B—H19B119.2
C17A—C18A—H18A119.7C17B—O20B—C21B118.34 (12)
C18A—C19A—C14A120.98 (13)O20B—C21B—C22B106.99 (12)
C18A—C19A—H19A119.5O20B—C21B—H21C110.3
C14A—C19A—H19A119.5C22B—C21B—H21C110.3
C17A—O20A—C21A116.96 (11)O20B—C21B—H21D110.3
O20A—C21A—C22A107.35 (11)C22B—C21B—H21D110.3
O20A—C21A—H21A110.2H21C—C21B—H21D108.6
C22A—C21A—H21A110.2C21B—C22B—C23B113.15 (12)
O20A—C21A—H21B110.2C21B—C22B—H22C108.9
C22A—C21A—H21B110.2C23B—C22B—H22C108.9
H21A—C21A—H21B108.5C21B—C22B—H22D108.9
C21A—C22A—C23A113.06 (12)C23B—C22B—H22D108.9
C21A—C22A—H22A109.0H22C—C22B—H22D107.8
C23A—C22A—H22A109.0C22B—C23B—C24B112.01 (12)
C21A—C22A—H22B109.0C22B—C23B—H23C109.2
C23A—C22A—H22B109.0C24B—C23B—H23C109.2
H22A—C22A—H22B107.8C22B—C23B—H23D109.2
C24A—C23A—C22A111.57 (12)C24B—C23B—H23D109.2
C24A—C23A—H23A109.3H23C—C23B—H23D107.9
C22A—C23A—H23A109.3C25B—C24B—C23B113.76 (12)
C24A—C23A—H23B109.3C25B—C24B—H24C108.8
C22A—C23A—H23B109.3C23B—C24B—H24C108.8
H23A—C23A—H23B108.0C25B—C24B—H24D108.8
C23A—C24A—C25A114.52 (12)C23B—C24B—H24D108.8
C23A—C24A—H24A108.6H24C—C24B—H24D107.7
C25A—C24A—H24A108.6C24B—C25B—C26B112.95 (12)
C23A—C24A—H24B108.6C24B—C25B—H25C109.0
C25A—C24A—H24B108.6C26B—C25B—H25C109.0
H24A—C24A—H24B107.6C24B—C25B—H25D109.0
C26A—C25A—C24A111.95 (12)C26B—C25B—H25D109.0
C26A—C25A—H25A109.2H25C—C25B—H25D107.8
C24A—C25A—H25A109.2C27B—C26B—C25B113.48 (12)
C26A—C25A—H25B109.2C27B—C26B—H26C108.9
C24A—C25A—H25B109.2C25B—C26B—H26C108.9
H25A—C25A—H25B107.9C27B—C26B—H26D108.9
C25A—C26A—C27A114.25 (12)C25B—C26B—H26D108.9
C25A—C26A—H26A108.7H26C—C26B—H26D107.7
C27A—C26A—H26A108.7C26B—C27B—C28B113.71 (12)
C25A—C26A—H26B108.7C26B—C27B—H27C108.8
C27A—C26A—H26B108.7C28B—C27B—H27C108.8
H26A—C26A—H26B107.6C26B—C27B—H27D108.8
C28A—C27A—C26A112.96 (13)C28B—C27B—H27D108.8
C28A—C27A—H27A109.0H27C—C27B—H27D107.7
C26A—C27A—H27A109.0C29B—C28B—C27B112.63 (12)
C28A—C27A—H27B109.0C29B—C28B—H28C109.1
C26A—C27A—H27B109.0C27B—C28B—H28C109.1
H27A—C27A—H27B107.8C29B—C28B—H28D109.1
C29A—C28A—C27A114.62 (13)C27B—C28B—H28D109.1
C29A—C28A—H28A108.6H28C—C28B—H28D107.8
C27A—C28A—H28A108.6C28B—C29B—C30B113.73 (12)
C29A—C28A—H28B108.6C28B—C29B—H29C108.8
C27A—C28A—H28B108.6C30B—C29B—H29C108.8
H28A—C28A—H28B107.6C28B—C29B—H29D108.8
C28A—C29A—C30A113.43 (15)C30B—C29B—H29D108.8
C28A—C29A—H29A108.9H29C—C29B—H29D107.7
C30A—C29A—H29A108.9C31B—C30B—C29B112.79 (13)
C28A—C29A—H29B108.9C31B—C30B—H30C109.0
C30A—C29A—H29B108.9C29B—C30B—H30C109.0
H29A—C29A—H29B107.7C31B—C30B—H30D109.0
C31A—C30A—C29A114.55 (17)C29B—C30B—H30D109.0
C31A—C30A—H30A108.6H30C—C30B—H30D107.8
C29A—C30A—H30A108.6C30B—C31B—H31D109.5
C31A—C30A—H30B108.6C30B—C31B—H31E109.5
C29A—C30A—H30B108.6H31D—C31B—H31E109.5
H30A—C30A—H30B107.6C30B—C31B—H31F109.5
C30A—C31A—H31A109.5H31D—C31B—H31F109.5
C30A—C31A—H31B109.5H31E—C31B—H31F109.5
H31A—C31A—H31B109.5C5B—C32B—H32D109.5
C30A—C31A—H31C109.5C5B—C32B—H32E109.5
H31A—C31A—H31C109.5H32D—C32B—H32E109.5
H31B—C31A—H31C109.5C5B—C32B—H32F109.5
C5A—C32A—H32A109.5H32D—C32B—H32F109.5
C5A—C32A—H32B109.5H32E—C32B—H32F109.5
F1B—C1A—C2A—F2A−105.63 (18)C2A—C1A—C2B—F3B−130.47 (16)
F1A—C1A—C2A—F2A14.34 (19)F1B—C1A—C2B—F2B−9.7 (2)
C2B—C1A—C2A—F2A132.12 (15)F1A—C1A—C2B—F2B−129.92 (18)
F1B—C1A—C2A—F3A11.2 (2)C2A—C1A—C2B—F2B112.46 (17)
F1A—C1A—C2A—F3A131.15 (15)F1B—C1A—C2B—C3B−129.22 (16)
C2B—C1A—C2A—F3A−111.07 (15)F1A—C1A—C2B—C3B110.59 (17)
F1B—C1A—C2A—C3A131.47 (16)C2A—C1A—C2B—C3B−7.03 (18)
F1A—C1A—C2A—C3A−108.56 (15)C4A—C3A—C3B—C4B5.9 (3)
C2B—C1A—C2A—C3A9.22 (18)C2A—C3A—C3B—C4B−172.90 (14)
F2A—C2A—C3A—C3B−130.70 (15)C4A—C3A—C3B—C2B−177.08 (15)
F3A—C2A—C3A—C3B110.24 (15)C2A—C3A—C3B—C2B4.12 (19)
C1A—C2A—C3A—C3B−8.56 (18)F3B—C2B—C3B—C3A123.74 (16)
F2A—C2A—C3A—C4A50.4 (2)F2B—C2B—C3B—C3A−116.56 (16)
F3A—C2A—C3A—C4A−68.68 (18)C1A—C2B—C3B—C3A2.05 (19)
C1A—C2A—C3A—C4A172.51 (14)F3B—C2B—C3B—C4B−59.0 (2)
C3B—C3A—C4A—C5A43.2 (2)F2B—C2B—C3B—C4B60.7 (2)
C2A—C3A—C4A—C5A−138.06 (16)C1A—C2B—C3B—C4B179.33 (14)
C3B—C3A—C4A—C6A−137.44 (16)C3A—C3B—C4B—C5B47.9 (2)
C2A—C3A—C4A—C6A41.3 (2)C2B—C3B—C4B—C5B−128.86 (16)
C6A—C4A—C5A—C32A−176.13 (15)C3A—C3B—C4B—C6B−131.24 (17)
C3A—C4A—C5A—C32A3.3 (3)C2B—C3B—C4B—C6B52.0 (2)
C6A—C4A—C5A—S1A1.47 (16)C6B—C4B—C5B—C32B−176.92 (14)
C3A—C4A—C5A—S1A−179.14 (12)C3B—C4B—C5B—C32B3.8 (2)
C7A—S1A—C5A—C4A−1.16 (12)C6B—C4B—C5B—S1B1.18 (16)
C7A—S1A—C5A—C32A176.75 (13)C3B—C4B—C5B—S1B−178.06 (11)
C5A—C4A—C6A—C7A−1.12 (19)C7B—S1B—C5B—C4B−0.29 (12)
C3A—C4A—C6A—C7A179.48 (13)C7B—S1B—C5B—C32B178.02 (12)
C4A—C6A—C7A—C8A175.55 (14)C5B—C4B—C6B—C7B−1.77 (18)
C4A—C6A—C7A—S1A0.22 (16)C3B—C4B—C6B—C7B177.48 (13)
C5A—S1A—C7A—C6A0.53 (12)C4B—C6B—C7B—C8B−177.73 (14)
C5A—S1A—C7A—C8A−175.10 (12)C4B—C6B—C7B—S1B1.49 (16)
C6A—C7A—C8A—C13A−169.33 (15)C5B—S1B—C7B—C6B−0.69 (12)
S1A—C7A—C8A—C13A5.5 (2)C5B—S1B—C7B—C8B178.59 (12)
C6A—C7A—C8A—C9A6.2 (2)C6B—C7B—C8B—C13B−22.3 (2)
S1A—C7A—C8A—C9A−178.99 (12)S1B—C7B—C8B—C13B158.51 (11)
C13A—C8A—C9A—C10A0.0 (2)C6B—C7B—C8B—C9B156.00 (16)
C7A—C8A—C9A—C10A−175.66 (15)S1B—C7B—C8B—C9B−23.1 (2)
C8A—C9A—C10A—C11A−1.2 (3)C13B—C8B—C9B—C10B1.2 (2)
C8A—C9A—C10A—F5A159.1 (3)C7B—C8B—C9B—C10B−177.13 (14)
C9A—C10A—C11A—C12A2.0 (2)C8B—C9B—C10B—F5B177.0 (3)
F5A—C10A—C11A—C12A−156.4 (3)C8B—C9B—C10B—C11B−0.2 (2)
C9A—C10A—C11A—C14A−178.99 (15)F5B—C10B—C11B—C12B−178.1 (3)
F5A—C10A—C11A—C14A22.7 (4)C9B—C10B—C11B—C12B−1.0 (2)
C10A—C11A—C12A—F4A175.25 (14)F5B—C10B—C11B—C14B−1.9 (4)
C14A—C11A—C12A—F4A−3.7 (2)C9B—C10B—C11B—C14B175.18 (14)
C10A—C11A—C12A—C13A−1.9 (2)C10B—C11B—C12B—F4B177.47 (13)
C14A—C11A—C12A—C13A179.16 (14)C14B—C11B—C12B—F4B1.3 (2)
F4A—C12A—C13A—C8A−176.34 (14)C10B—C11B—C12B—C13B1.3 (2)
C11A—C12A—C13A—C8A0.9 (2)C14B—C11B—C12B—C13B−174.90 (13)
C9A—C8A—C13A—C12A0.1 (2)F4B—C12B—C13B—C8B−176.55 (13)
C7A—C8A—C13A—C12A175.73 (14)C11B—C12B—C13B—C8B−0.3 (2)
C10A—C11A—C14A—C15A26.1 (2)C9B—C8B—C13B—C12B−1.0 (2)
C12A—C11A—C14A—C15A−154.98 (15)C7B—C8B—C13B—C12B177.41 (13)
C10A—C11A—C14A—C19A−151.76 (15)C12B—C11B—C14B—C19B−46.0 (2)
C12A—C11A—C14A—C19A27.2 (2)C10B—C11B—C14B—C19B138.05 (15)
C19A—C14A—C15A—C16A3.3 (2)C12B—C11B—C14B—C15B131.95 (15)
C11A—C14A—C15A—C16A−174.65 (13)C10B—C11B—C14B—C15B−44.0 (2)
C14A—C15A—C16A—C17A−1.3 (2)C19B—C14B—C15B—C16B1.1 (2)
C15A—C16A—C17A—O20A179.20 (13)C11B—C14B—C15B—C16B−176.87 (13)
C15A—C16A—C17A—C18A−1.7 (2)C14B—C15B—C16B—C17B−1.1 (2)
O20A—C17A—C18A—C19A−178.38 (12)C15B—C16B—C17B—O20B179.34 (13)
C16A—C17A—C18A—C19A2.4 (2)C15B—C16B—C17B—C18B−0.3 (2)
C17A—C18A—C19A—C14A−0.3 (2)O20B—C17B—C18B—C19B−178.00 (13)
C15A—C14A—C19A—C18A−2.5 (2)C16B—C17B—C18B—C19B1.6 (2)
C11A—C14A—C19A—C18A175.35 (13)C15B—C14B—C19B—C18B0.2 (2)
C16A—C17A—O20A—C21A−6.48 (19)C11B—C14B—C19B—C18B178.19 (13)
C18A—C17A—O20A—C21A174.35 (12)C17B—C18B—C19B—C14B−1.6 (2)
C17A—O20A—C21A—C22A−176.30 (11)C18B—C17B—O20B—C21B−1.6 (2)
O20A—C21A—C22A—C23A179.82 (11)C16B—C17B—O20B—C21B178.79 (12)
C21A—C22A—C23A—C24A178.18 (12)C17B—O20B—C21B—C22B171.24 (12)
C22A—C23A—C24A—C25A179.34 (12)O20B—C21B—C22B—C23B175.02 (11)
C23A—C24A—C25A—C26A−178.77 (12)C21B—C22B—C23B—C24B179.14 (12)
C24A—C25A—C26A—C27A−178.05 (13)C22B—C23B—C24B—C25B179.04 (12)
C25A—C26A—C27A—C28A175.55 (14)C23B—C24B—C25B—C26B−178.33 (12)
C26A—C27A—C28A—C29A−163.14 (16)C24B—C25B—C26B—C27B177.23 (12)
C27A—C28A—C29A—C30A179.31 (17)C25B—C26B—C27B—C28B179.52 (12)
C28A—C29A—C30A—C31A−173.09 (18)C26B—C27B—C28B—C29B−177.11 (12)
F1B—C1A—C2B—F3B107.34 (18)C27B—C28B—C29B—C30B−176.58 (12)
F1A—C1A—C2B—F3B−12.9 (2)C28B—C29B—C30B—C31B−177.79 (13)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2453).

References

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