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The title compound, C80F30, is one of seven isomers of C70(CF3)10 that have been isolated. The C2-symmetry fullerene mol­ecule has an idealized D5h C70 core with the ten CF3 groups arranged on a `pole-to-pole' para-meta-para-para-para-para-para-meta-para (pmp5mp) ribbon of edge-sharing C6(CF3)2 hexa­gons. There are no cage Csp3—Csp3 bonds. There are intra­molecular F...F contacts between pairs of CF3 groups on the same hexa­gon that range from 2.560 (3) to 2.876 (3) Å. Two CF3 groups are disordered with almost equal occupancies.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043991/om2161sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043991/om2161Isup2.hkl
Contains datablock I

CCDC reference: 663777

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.053
  • wR factor = 0.124
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT213_ALERT_2_B Atom F11 has ADP max/min Ratio ............. 4.40 prola PLAT220_ALERT_2_B Large Non-Solvent F Ueq(max)/Ueq(min) ... 3.62 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound .. ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT213_ALERT_2_C Atom F12 has ADP max/min Ratio ............. 3.90 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C74 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C75 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact F6 .. C22 .. 2.92 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact F8 .. C16 .. 2.96 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 37.00 A   3 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 12.40 Deg. C75 -C19 -C75A 1.555 1.555 1.555
Alert level G CHEMS02_ALERT_1_G Please check that you have entered the correct _publ_requested_category classification of your compound; FI or CI or EI for inorganic; FM or CM or EM for metal-organic; FO or CO or EO for organic. From the CIF: _publ_requested_category EO From the CIF: _chemical_formula_sum:C80 F30 PLAT793_ALERT_1_G Check the Absolute Configuration of C10 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C25 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 25
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Recently reported high-temperature reactions of C70 with CF3I have yielded more than two dozen C70(CF3)n derivatives (n = 2–18), most with relatively stable addition patterns that are chiral as well as unprecedented in fullerene(X)n chemistry (Kareev, Kuvychko, Lebedkin et al., 2005; Kareev et al., 2006a; Kareev et al., 2006b; Avdoshenko et al., 2006; Goryunkov et al., 2006; Ignat'eva et al., 2006; Popov, Kareev, Shustova et al., 2007; Shustova, Peryshkov, Kareev, et al., 2007). A member of the n = 10 set of seven isomers (Popov, Kareev, Shustova et al., 2007), the title compound has been crystallized from toluene and we report its crystal structure here.

The structure of the title compound, as shown in Figs. 1 and 2, comprises an idealized D5 h C70 core with ten sp3 carbon atoms at positions 1, 4, 10, 19, 25, 41, 55, 60, 67, and 69 (Powell et al., 2002), each of which is attached to a CF3 group. The cage sp3 carbon atoms are not adjacent to one another. The CF3 groups are arranged on a para-meta-para-para-para-para-para- meta-para (pmp5mp) ribbon of edge-sharing C6(CF3)2 hexagons. The shared edges in each ribbon of hexagons are C(sp3)-C(sp2) bonds (e.g., C1—C2, C4—C5, etc.), not C(sp2)-C(sp2) bonds. Thus, any pair of adjacent hexagons along the ribbon has a common CF3 group.

The two CF3 groups in the middle of the ribbon are disordered and were refined as half atoms. Only one set of the two disordered pairs is shown in the figures. As in all other published structures of fullerene(CF3)n compounds, there are F···F intramolecular contacts between pairs of neighboring CF3 groups. The range of F···F distances that do not involve the disordered CF3 groups is from 2.539 (3) to 2.756 (3) Å. The range of C···F distances that do not involve the disordered CF3 groups is from 1.323 (3) to 1.338 (3) Å.

The shortest cage C—C bond in the asymmetric unit is C8—C9, at 1.349 (4) Å. This is significantly shorter than the shortest C—C bond of this type in the most precise structure of empty C70 reported to date (C9H3Cl6N.3(C70).3(C6H5Cl)), which is 1.440 (4) Å (Pham et al., 2007). More importantly, the C8—C9 bond is a pentagon-hexagon junction, and the shortest pent-hex junction in C9H3Cl6N.3(C70).3(C6H5Cl)) is also 1.440 (4) Å (the longest pent-hex junction in C9H3Cl6N.3(C70).3(C6H5Cl)) is 1.460 (4) Å.

Related literature top

For related literature, see: Avdoshenko et al. (2006); Goryunkov et al. (2006); Ignat'eva et al. (2006); Kareev et al. (2005, 2006a,b); Pham et al. (2007); Popov et al. (2007); Powell et al. (2002); Shustova et al. (2007).

Experimental top

The synthesis of the title compound was carried out by heating C70 in a stream of CF3I at 420 °C as previously described (Popov, Kareev, Shustova, et al. 2007). Crystals of the HPLC-purified compound were grown by slow evaporation of a saturated deuterochloroform solution.

Refinement top

The maximum (0.47 e/Å3) and minimum (-0.54 e/Å3) residual electron density peaks were located 0.66 Å and 0.24 Å from F11.

Structure description top

Recently reported high-temperature reactions of C70 with CF3I have yielded more than two dozen C70(CF3)n derivatives (n = 2–18), most with relatively stable addition patterns that are chiral as well as unprecedented in fullerene(X)n chemistry (Kareev, Kuvychko, Lebedkin et al., 2005; Kareev et al., 2006a; Kareev et al., 2006b; Avdoshenko et al., 2006; Goryunkov et al., 2006; Ignat'eva et al., 2006; Popov, Kareev, Shustova et al., 2007; Shustova, Peryshkov, Kareev, et al., 2007). A member of the n = 10 set of seven isomers (Popov, Kareev, Shustova et al., 2007), the title compound has been crystallized from toluene and we report its crystal structure here.

The structure of the title compound, as shown in Figs. 1 and 2, comprises an idealized D5 h C70 core with ten sp3 carbon atoms at positions 1, 4, 10, 19, 25, 41, 55, 60, 67, and 69 (Powell et al., 2002), each of which is attached to a CF3 group. The cage sp3 carbon atoms are not adjacent to one another. The CF3 groups are arranged on a para-meta-para-para-para-para-para- meta-para (pmp5mp) ribbon of edge-sharing C6(CF3)2 hexagons. The shared edges in each ribbon of hexagons are C(sp3)-C(sp2) bonds (e.g., C1—C2, C4—C5, etc.), not C(sp2)-C(sp2) bonds. Thus, any pair of adjacent hexagons along the ribbon has a common CF3 group.

The two CF3 groups in the middle of the ribbon are disordered and were refined as half atoms. Only one set of the two disordered pairs is shown in the figures. As in all other published structures of fullerene(CF3)n compounds, there are F···F intramolecular contacts between pairs of neighboring CF3 groups. The range of F···F distances that do not involve the disordered CF3 groups is from 2.539 (3) to 2.756 (3) Å. The range of C···F distances that do not involve the disordered CF3 groups is from 1.323 (3) to 1.338 (3) Å.

The shortest cage C—C bond in the asymmetric unit is C8—C9, at 1.349 (4) Å. This is significantly shorter than the shortest C—C bond of this type in the most precise structure of empty C70 reported to date (C9H3Cl6N.3(C70).3(C6H5Cl)), which is 1.440 (4) Å (Pham et al., 2007). More importantly, the C8—C9 bond is a pentagon-hexagon junction, and the shortest pent-hex junction in C9H3Cl6N.3(C70).3(C6H5Cl)) is also 1.440 (4) Å (the longest pent-hex junction in C9H3Cl6N.3(C70).3(C6H5Cl)) is 1.460 (4) Å.

For related literature, see: Avdoshenko et al. (2006); Goryunkov et al. (2006); Ignat'eva et al. (2006); Kareev et al. (2005, 2006a,b); Pham et al. (2007); Popov et al. (2007); Powell et al. (2002); Shustova et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: APEX2 (Bruker, 2000); data reduction: APEX2 (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. The crystallographic C2 axis is perpendicular to the plane of the page. Only one pair of the disordered CF3 groups on the hexagon centered on the C2 axis is shown.
[Figure 2] Fig. 2. (Left) Schlegel diagram showing the IUPAC lowest-locants for the cage carbon atoms. The C2 axis passes through the center of the hexagon with C19 and C41 and bisects the C30—C50 bond. The CF3 groups are attached to the cage carbon atoms depicted as black circles. Also shown is the ribbon of meta- and para-C6(CF3)2 edge-sharing hexagons (the two meta-C6(CF3)2 hexagons are indicated with the letter m). (Right) The structure showing the atom numbers for the CF3 groups and the network of F···F contacts between CF3 groups that share the same hexagon.
1,4,10,19,25,41,55,60,67,69-Decakis(trifluoromethyl)- 1,4,10,19,25,41,55,60,67,69-decahydro(C70—D5 h)[5,6]fullerene top
Crystal data top
C80F30Dx = 2.012 Mg m3
Mr = 1530.80Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 999 reflections
a = 16.0658 (3) Åθ = 1.7–27.9°
b = 17.2662 (4) ŵ = 0.20 mm1
c = 18.2153 (4) ÅT = 100 K
V = 5052.84 (19) Å3Plate, red
Z = 40.44 × 0.10 × 0.05 mm
F(000) = 3000
Data collection top
Bruker Kappa APEXII
diffractometer
5853 independent reflections
Radiation source: fine-focus sealed tube3409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
φ and ω scansθmax = 27.9°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1921
Tmin = 0.920, Tmax = 0.990k = 2021
53138 measured reflectionsl = 2319
Refinement top
Refinement on F225 restraints
Least-squares matrix: fullPrimary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.053Secondary atom site location: difference Fourier map
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0456P)2 + 4.0833P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.026
5853 reflectionsΔρmax = 0.47 e Å3
534 parametersΔρmin = 0.54 e Å3
Crystal data top
C80F30V = 5052.84 (19) Å3
Mr = 1530.80Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 16.0658 (3) ŵ = 0.20 mm1
b = 17.2662 (4) ÅT = 100 K
c = 18.2153 (4) Å0.44 × 0.10 × 0.05 mm
Data collection top
Bruker Kappa APEXII
diffractometer
5853 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
3409 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.990Rint = 0.098
53138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053534 parameters
wR(F2) = 0.12425 restraints
S = 1.02Δρmax = 0.47 e Å3
5853 reflectionsΔρmin = 0.54 e Å3
Special details top

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 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.14807 (15)0.84689 (16)0.57610 (14)0.0172 (6)
C20.06726 (15)0.89202 (16)0.56364 (14)0.0171 (6)
C30.00314 (15)0.85035 (16)0.54804 (14)0.0179 (6)
C40.01274 (16)0.76084 (17)0.55711 (15)0.0212 (7)
C50.05113 (16)0.73164 (16)0.61305 (15)0.0192 (6)
C60.12706 (15)0.76964 (16)0.61409 (15)0.0171 (6)
C70.18225 (15)0.76010 (16)0.67239 (15)0.0181 (6)
C80.22979 (14)0.83155 (16)0.68340 (14)0.0161 (6)
C90.20545 (14)0.88497 (16)0.63383 (14)0.0158 (6)
C100.20897 (15)0.97126 (16)0.64795 (14)0.0163 (6)
C110.12152 (15)1.00488 (16)0.63621 (15)0.0169 (6)
C120.06016 (15)0.97158 (16)0.59058 (14)0.0161 (6)
C130.02077 (15)1.00408 (16)0.59698 (15)0.0181 (6)
C140.09317 (15)0.96120 (17)0.57594 (14)0.0187 (6)
C150.08409 (15)0.88541 (18)0.55430 (14)0.0208 (7)
C160.14344 (15)0.82795 (17)0.57804 (15)0.0203 (7)
C170.10068 (15)0.75657 (17)0.58928 (15)0.0216 (7)
C180.12203 (16)0.71052 (17)0.64672 (16)0.0224 (7)
C190.06088 (16)0.65728 (16)0.68667 (16)0.0227 (7)
C200.02896 (16)0.68342 (16)0.67393 (16)0.0213 (7)
C210.08471 (16)0.67492 (16)0.73207 (16)0.0219 (7)
C220.16204 (15)0.71231 (16)0.73075 (15)0.0201 (6)
C230.18732 (15)0.73373 (17)0.80518 (15)0.0208 (7)
C240.23331 (15)0.79965 (17)0.81776 (15)0.0191 (6)
C250.27335 (15)0.84797 (16)0.75587 (15)0.0196 (6)
C260.24996 (15)0.93044 (17)0.77931 (15)0.0188 (6)
C270.21993 (15)0.98455 (16)0.73100 (14)0.0179 (6)
C280.15831 (16)1.03892 (16)0.75525 (15)0.0193 (6)
C290.09863 (16)1.05095 (16)0.69643 (15)0.0187 (6)
C300.01394 (16)1.07106 (15)0.71141 (15)0.0174 (6)
C310.04340 (15)1.05362 (16)0.65680 (15)0.0173 (6)
C320.13118 (15)1.04049 (16)0.67284 (15)0.0185 (6)
C330.16206 (15)0.98408 (17)0.62258 (15)0.0203 (6)
C450.20949 (15)0.84927 (17)0.87587 (15)0.0209 (7)
C460.21946 (15)0.92902 (17)0.85350 (15)0.0203 (7)
C710.36707 (16)0.83212 (18)0.75032 (16)0.0232 (7)
C720.27308 (16)1.01737 (17)0.60260 (15)0.0208 (6)
C730.19695 (16)0.83397 (17)0.50429 (15)0.0218 (7)
C740.00903 (18)0.7147 (2)0.48471 (18)0.0334 (8)
F10.40336 (9)0.87577 (10)0.69942 (9)0.0298 (4)
F20.40463 (9)0.84669 (11)0.81408 (9)0.0356 (5)
F30.38117 (10)0.75794 (10)0.73328 (10)0.0354 (5)
F40.34564 (9)0.98094 (10)0.59759 (9)0.0324 (4)
F50.24686 (9)1.03264 (10)0.53477 (8)0.0281 (4)
F60.28737 (11)1.08613 (10)0.63398 (9)0.0373 (5)
F70.24219 (11)0.89500 (11)0.48588 (10)0.0401 (5)
F80.24879 (11)0.77447 (11)0.51097 (9)0.0424 (5)
F90.14794 (10)0.81972 (11)0.44729 (9)0.0376 (5)
F100.06645 (10)0.69174 (11)0.46686 (9)0.0389 (5)
F110.05481 (16)0.65144 (16)0.48843 (15)0.1015 (12)
F120.03764 (16)0.75595 (16)0.42896 (11)0.0793 (9)
F130.0496 (3)0.5632 (3)0.5902 (3)0.053 (2)0.511 (8)
F140.0479 (5)0.5247 (3)0.7019 (4)0.060 (3)0.511 (8)
F150.1603 (3)0.5624 (4)0.6519 (4)0.0402 (15)0.511 (8)
C750.0798 (8)0.5751 (6)0.6567 (7)0.021 (3)0.511 (8)
F13A0.1288 (5)0.5590 (4)0.6213 (4)0.0464 (19)0.489 (8)
F14A0.0029 (3)0.5355 (2)0.6456 (4)0.052 (2)0.489 (8)
F15A0.0943 (4)0.5270 (3)0.7297 (3)0.0397 (14)0.489 (8)
C75A0.0701 (9)0.5695 (6)0.6721 (7)0.026 (4)0.489 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0157 (12)0.0214 (16)0.0144 (15)0.0016 (11)0.0022 (11)0.0013 (13)
C20.0184 (13)0.0260 (17)0.0068 (13)0.0017 (11)0.0034 (10)0.0004 (13)
C30.0195 (13)0.0248 (17)0.0094 (14)0.0003 (11)0.0003 (11)0.0056 (13)
C40.0186 (14)0.0266 (18)0.0184 (16)0.0040 (12)0.0028 (11)0.0114 (13)
C50.0203 (13)0.0177 (16)0.0196 (15)0.0012 (11)0.0043 (11)0.0097 (13)
C60.0166 (13)0.0166 (16)0.0182 (15)0.0006 (11)0.0056 (11)0.0055 (13)
C70.0127 (12)0.0184 (16)0.0231 (16)0.0043 (11)0.0049 (11)0.0021 (13)
C80.0114 (12)0.0199 (16)0.0170 (15)0.0009 (10)0.0036 (10)0.0018 (13)
C90.0137 (12)0.0206 (16)0.0130 (14)0.0009 (11)0.0056 (10)0.0028 (13)
C100.0164 (12)0.0186 (16)0.0139 (14)0.0031 (11)0.0000 (11)0.0009 (12)
C110.0210 (13)0.0145 (15)0.0153 (15)0.0021 (11)0.0045 (11)0.0035 (12)
C120.0204 (13)0.0206 (17)0.0073 (14)0.0002 (11)0.0020 (11)0.0038 (12)
C130.0224 (14)0.0208 (17)0.0109 (15)0.0017 (11)0.0016 (11)0.0052 (13)
C140.0187 (13)0.0283 (18)0.0092 (14)0.0046 (12)0.0030 (10)0.0050 (13)
C150.0176 (13)0.037 (2)0.0075 (14)0.0006 (12)0.0022 (11)0.0045 (13)
C160.0169 (13)0.0309 (18)0.0133 (15)0.0002 (12)0.0059 (11)0.0079 (13)
C170.0154 (13)0.0305 (18)0.0188 (16)0.0068 (12)0.0001 (11)0.0135 (14)
C180.0193 (13)0.0237 (17)0.0242 (17)0.0070 (12)0.0012 (12)0.0120 (14)
C190.0218 (14)0.0168 (17)0.0294 (17)0.0046 (11)0.0076 (12)0.0073 (14)
C200.0199 (13)0.0136 (16)0.0305 (18)0.0005 (11)0.0073 (12)0.0088 (14)
C210.0215 (14)0.0111 (15)0.0332 (18)0.0027 (11)0.0083 (12)0.0012 (13)
C220.0161 (13)0.0172 (16)0.0272 (17)0.0059 (11)0.0044 (12)0.0020 (14)
C230.0159 (13)0.0227 (17)0.0237 (16)0.0071 (11)0.0014 (12)0.0080 (14)
C240.0115 (12)0.0268 (18)0.0190 (15)0.0054 (11)0.0003 (11)0.0086 (13)
C250.0138 (12)0.0265 (17)0.0185 (15)0.0000 (11)0.0001 (11)0.0031 (14)
C260.0107 (12)0.0283 (17)0.0174 (15)0.0040 (11)0.0003 (11)0.0010 (14)
C270.0162 (12)0.0206 (16)0.0168 (15)0.0077 (11)0.0008 (11)0.0025 (13)
C280.0199 (13)0.0170 (16)0.0209 (16)0.0075 (11)0.0027 (11)0.0023 (13)
C290.0238 (14)0.0133 (16)0.0191 (16)0.0032 (11)0.0032 (12)0.0064 (13)
C300.0263 (14)0.0072 (14)0.0187 (15)0.0004 (11)0.0029 (12)0.0011 (12)
C310.0214 (13)0.0157 (16)0.0150 (15)0.0039 (11)0.0027 (11)0.0070 (12)
C320.0205 (13)0.0201 (16)0.0147 (15)0.0085 (11)0.0006 (11)0.0050 (13)
C330.0180 (13)0.0288 (18)0.0140 (15)0.0082 (12)0.0034 (11)0.0061 (13)
C450.0126 (12)0.0342 (19)0.0161 (15)0.0017 (12)0.0060 (11)0.0053 (14)
C460.0123 (12)0.0337 (19)0.0148 (15)0.0040 (12)0.0046 (11)0.0005 (14)
C710.0151 (13)0.033 (2)0.0218 (16)0.0016 (12)0.0007 (12)0.0051 (15)
C720.0211 (14)0.0236 (18)0.0177 (16)0.0044 (12)0.0005 (11)0.0014 (14)
C730.0168 (13)0.0291 (18)0.0194 (16)0.0016 (12)0.0018 (12)0.0023 (14)
C740.0258 (16)0.043 (2)0.0315 (19)0.0086 (15)0.0094 (14)0.0174 (17)
F10.0171 (8)0.0452 (12)0.0270 (10)0.0027 (7)0.0034 (7)0.0059 (9)
F20.0168 (8)0.0643 (13)0.0256 (10)0.0002 (8)0.0042 (7)0.0052 (9)
F30.0215 (8)0.0346 (12)0.0501 (12)0.0089 (7)0.0046 (8)0.0034 (9)
F40.0177 (8)0.0434 (11)0.0361 (11)0.0030 (7)0.0064 (7)0.0092 (9)
F50.0277 (8)0.0388 (11)0.0177 (9)0.0057 (7)0.0022 (7)0.0079 (8)
F60.0518 (11)0.0297 (11)0.0302 (10)0.0222 (8)0.0131 (8)0.0067 (9)
F70.0467 (11)0.0412 (12)0.0325 (11)0.0192 (9)0.0217 (9)0.0082 (9)
F80.0464 (11)0.0493 (13)0.0315 (11)0.0266 (9)0.0178 (9)0.0039 (10)
F90.0282 (9)0.0677 (14)0.0168 (9)0.0052 (9)0.0048 (7)0.0127 (9)
F100.0309 (10)0.0548 (13)0.0310 (11)0.0059 (9)0.0081 (8)0.0190 (9)
F110.0947 (18)0.101 (2)0.109 (2)0.0763 (16)0.0727 (17)0.0905 (18)
F120.0927 (18)0.112 (2)0.0335 (13)0.0535 (15)0.0346 (12)0.0437 (14)
F130.071 (4)0.036 (3)0.054 (3)0.021 (2)0.030 (3)0.026 (2)
F140.088 (6)0.021 (3)0.072 (5)0.001 (3)0.054 (5)0.001 (3)
F150.025 (2)0.031 (3)0.064 (4)0.008 (2)0.003 (2)0.016 (3)
C750.018 (5)0.016 (6)0.028 (6)0.002 (4)0.001 (4)0.005 (4)
F13A0.066 (5)0.024 (3)0.049 (4)0.004 (3)0.029 (4)0.007 (3)
F14A0.039 (3)0.021 (3)0.096 (6)0.0068 (18)0.038 (3)0.022 (3)
F15A0.064 (4)0.020 (2)0.036 (3)0.011 (2)0.006 (2)0.001 (2)
C75A0.019 (5)0.040 (9)0.019 (6)0.004 (5)0.002 (4)0.003 (5)
Geometric parameters (Å, º) top
C1—C21.531 (4)C21—C19i1.559 (4)
C1—C61.540 (4)C22—C231.463 (4)
C1—C731.542 (4)C23—C241.376 (4)
C1—C91.545 (4)C23—C18i1.424 (4)
C2—C31.370 (4)C24—C451.415 (4)
C2—C121.463 (4)C24—C251.543 (4)
C3—C151.439 (4)C25—C261.533 (4)
C3—C41.562 (4)C25—C711.534 (4)
C4—C171.531 (4)C26—C271.371 (4)
C4—C51.531 (4)C26—C461.438 (4)
C4—C741.542 (4)C27—C281.434 (4)
C5—C61.385 (4)C28—C32i1.381 (4)
C5—C201.432 (4)C28—C291.453 (4)
C6—C71.393 (4)C29—C301.430 (4)
C7—C221.384 (4)C30—C311.389 (4)
C7—C81.465 (4)C30—C30i1.475 (5)
C8—C91.349 (4)C31—C321.458 (4)
C8—C251.521 (4)C32—C28i1.381 (4)
C9—C101.513 (4)C32—C331.426 (4)
C10—C111.535 (3)C33—C46i1.394 (4)
C10—C271.540 (4)C45—C16i1.402 (4)
C10—C721.542 (4)C45—C461.445 (4)
C11—C291.404 (4)C46—C33i1.394 (4)
C11—C121.412 (4)C71—F11.330 (3)
C12—C131.421 (4)C71—F21.333 (3)
C13—C141.431 (4)C71—F31.337 (3)
C13—C311.432 (4)C72—F41.328 (3)
C14—C151.374 (4)C72—F51.332 (3)
C14—C331.450 (4)C72—F61.338 (3)
C15—C161.442 (4)C73—F71.323 (3)
C16—C45i1.402 (4)C73—F91.326 (3)
C16—C171.426 (4)C73—F81.328 (3)
C17—C181.358 (4)C74—F101.316 (3)
C18—C23i1.424 (4)C74—F111.319 (4)
C18—C191.530 (4)C74—F121.323 (4)
C19—C201.530 (4)F13—C751.322 (12)
C19—C751.551 (10)F14—C751.303 (12)
C19—C75A1.546 (11)F15—C751.315 (12)
C19—C21i1.559 (4)F13A—C75A1.332 (13)
C20—C211.395 (4)F14A—C75A1.321 (13)
C21—C221.400 (4)F15A—C75A1.339 (13)
C2—C1—C6108.8 (2)C7—C22—C23119.7 (2)
C2—C1—C73112.3 (2)C21—C22—C23110.3 (2)
C6—C1—C73111.6 (2)C24—C23—C18i121.7 (3)
C2—C1—C9113.0 (2)C24—C23—C22120.8 (3)
C6—C1—C9101.2 (2)C18i—C23—C22107.1 (2)
C73—C1—C9109.6 (2)C23—C24—C45118.7 (2)
C3—C2—C12119.9 (2)C23—C24—C25123.3 (3)
C3—C2—C1117.6 (2)C45—C24—C25109.4 (2)
C12—C2—C1119.6 (2)C8—C25—C26107.6 (2)
C2—C3—C15120.6 (3)C8—C25—C71111.2 (2)
C2—C3—C4125.4 (2)C26—C25—C71115.1 (2)
C15—C3—C4108.6 (2)C8—C25—C24110.0 (2)
C17—C4—C5110.4 (2)C26—C25—C24101.3 (2)
C17—C4—C74109.8 (2)C71—C25—C24111.2 (2)
C5—C4—C74111.9 (2)C27—C26—C46119.7 (2)
C17—C4—C3100.3 (2)C27—C26—C25122.7 (2)
C5—C4—C3109.3 (2)C46—C26—C25109.2 (2)
C74—C4—C3114.6 (2)C26—C27—C28119.4 (2)
C6—C5—C20118.9 (2)C26—C27—C10124.7 (2)
C6—C5—C4116.3 (2)C28—C27—C10108.7 (2)
C20—C5—C4122.7 (2)C32i—C28—C27121.5 (3)
C5—C6—C7121.0 (3)C32i—C28—C29119.2 (2)
C5—C6—C1126.7 (2)C27—C28—C29108.8 (2)
C7—C6—C1107.8 (2)C11—C29—C30122.4 (2)
C22—C7—C6120.4 (2)C11—C29—C28108.8 (2)
C22—C7—C8121.3 (2)C30—C29—C28121.5 (2)
C6—C7—C8109.7 (2)C31—C30—C29116.2 (2)
C9—C8—C7109.5 (2)C31—C30—C30i118.8 (3)
C9—C8—C25126.0 (2)C29—C30—C30i118.1 (3)
C7—C8—C25121.0 (2)C30—C31—C13120.4 (2)
C8—C9—C10123.3 (2)C30—C31—C32122.1 (2)
C8—C9—C1109.7 (2)C13—C31—C32107.8 (2)
C10—C9—C1123.9 (2)C28i—C32—C33119.1 (3)
C9—C10—C11108.3 (2)C28i—C32—C31119.9 (2)
C9—C10—C27108.5 (2)C33—C32—C31108.3 (2)
C11—C10—C27100.7 (2)C46i—C33—C32119.7 (2)
C9—C10—C72116.3 (2)C46i—C33—C14120.1 (3)
C11—C10—C72110.0 (2)C32—C33—C14107.3 (2)
C27—C10—C72111.9 (2)C16i—C45—C24119.6 (3)
C29—C11—C12120.5 (2)C16i—C45—C46120.2 (3)
C29—C11—C10110.2 (2)C24—C45—C46109.6 (2)
C12—C11—C10124.5 (2)C33i—C46—C26120.5 (3)
C11—C12—C13115.5 (2)C33i—C46—C45119.2 (2)
C11—C12—C2121.7 (2)C26—C46—C45108.6 (2)
C13—C12—C2118.0 (2)F1—C71—F2107.6 (2)
C12—C13—C14121.2 (2)F1—C71—F3107.9 (2)
C12—C13—C31122.0 (2)F2—C71—F3107.8 (2)
C14—C13—C31107.8 (2)F1—C71—C25112.0 (2)
C15—C14—C13118.9 (2)F2—C71—C25110.7 (2)
C15—C14—C33120.6 (3)F3—C71—C25110.6 (2)
C13—C14—C33108.8 (2)F4—C72—F5107.9 (2)
C14—C15—C3121.3 (2)F4—C72—F6107.4 (2)
C14—C15—C16119.9 (2)F5—C72—F6106.0 (2)
C3—C15—C16109.4 (3)F4—C72—C10112.3 (2)
C45i—C16—C17120.4 (3)F5—C72—C10112.8 (2)
C45i—C16—C15119.9 (3)F6—C72—C10110.1 (2)
C17—C16—C15108.6 (2)F7—C73—F9106.0 (2)
C18—C17—C16119.7 (2)F7—C73—F8107.2 (2)
C18—C17—C4123.8 (3)F9—C73—F8107.5 (2)
C16—C17—C4110.4 (2)F7—C73—C1112.3 (2)
C17—C18—C23i119.7 (3)F9—C73—C1112.9 (2)
C17—C18—C19123.8 (2)F8—C73—C1110.7 (2)
C23i—C18—C19110.5 (2)F10—C74—F11106.1 (3)
C18—C19—C20110.9 (2)F10—C74—F12107.0 (3)
C18—C19—C75104.9 (5)F11—C74—F12107.0 (3)
C20—C19—C75113.7 (5)F10—C74—C4113.7 (2)
C18—C19—C75A116.5 (6)F11—C74—C4111.3 (3)
C20—C19—C75A110.7 (5)F12—C74—C4111.4 (3)
C75—C19—C75A12.4 (8)F14—C75—F13109.3 (10)
C18—C19—C21i100.2 (2)F14—C75—F15108.6 (9)
C20—C19—C21i108.6 (2)F13—C75—F15105.9 (10)
C75—C19—C21i117.7 (5)F14—C75—C19108.2 (8)
C75A—C19—C21i109.4 (5)F13—C75—C19113.1 (8)
C21—C20—C5119.3 (2)F15—C75—C19111.6 (8)
C21—C20—C19117.4 (3)F13A—C75A—F14A105.4 (10)
C5—C20—C19121.6 (2)F13A—C75A—F15A105.3 (9)
C20—C21—C22120.5 (3)F14A—C75A—F15A106.2 (10)
C20—C21—C19i125.7 (2)F13A—C75A—C19108.7 (9)
C22—C21—C19i108.9 (2)F14A—C75A—C19114.8 (9)
C7—C22—C21119.7 (3)F15A—C75A—C19115.5 (9)
Symmetry code: (i) x, y, z+3/2.

Experimental details

Crystal data
Chemical formulaC80F30
Mr1530.80
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)100
a, b, c (Å)16.0658 (3), 17.2662 (4), 18.2153 (4)
V3)5052.84 (19)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.44 × 0.10 × 0.05
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.920, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
53138, 5853, 3409
Rint0.098
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.124, 1.02
No. of reflections5853
No. of parameters534
No. of restraints25
Δρmax, Δρmin (e Å3)0.47, 0.54

Computer programs: APEX2 (Bruker, 2000), SHELXTL (Bruker, 2000).

Correspondence of IUPAC lowest locants with crystallographic atom numbers for C2-1,4,10,19,25,41,55,60,67,69-C70(CF3)10 top
C1C1
C2C2
C3C3
C4C4
C5C5
C6C6
C7C7
C8C8
C9C9
C10C10
C11C11
C12C12
C13C13
C14C14
C15C15
C16C16
C17C17
C18C18
C19C19
C20C20
C21C21
C22C22
C23C23
C24C24
C25C25
C26C26
C27C27
C28C28
C29C29
C30C30
C31C31
C32C32
C33C33
C34C46a
C35C45a
C36C24a
C37C23a
C38C22a
C39C21a
C40C20a
C41C19a
C42C18a
C43C17a
C44C16a
C45C45
C46C46
C47C33a
C48C32a
C49C31a
C50C30a
C51C29a
C52C28a
C53C27a
C54C26a
C55C25a
C56C8a
C57C7a
C58C6a
C59C5a
C60C4a
C61C3a
C62C15a
C63C14a
C64C13a
C65C12a
C66C11a
C67C10a
C68C9a
C69C1a
C70C2a
 

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