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The title compound, C68F24·CDCl3, is a solvate of one of five isomers of C60(CF3)8 that have now been isolated. The fullerene mol­ecule has an idealized Ih C60 core with the eight CF3 groups arranged in an asymmetric fashion on a paraparaparametaparametapara 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, in the range 2.544 (2)–2.641 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031704/tk2170sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031704/tk2170Isup2.hkl
Contains datablock I

CCDC reference: 657682

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.054
  • wR factor = 0.150
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Cl2 .. F651 .. 2.90 Ang.
Alert level C PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound .. ? PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -1.31 e/A    PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C69 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. F681 .. 2.92 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. F621 .. 3.13 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. F672 .. 3.02 Ang.
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:C69 Cl3 D1 F24 PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C16 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C18 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C24 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C27 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C36 = ... S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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 C60 with CF3I have yielded five C60(CF3)8 derivatives, with thermodynamically stable addition patterns that are asymmetric as well as unprecedented in fullerene(X)n chemistry (Kareev et al., 2005; Kareev, Lebedkin, Popov et al., 2006; Kareev, Lebedkin, Miller et al., 2006; Popov et al., 2007). A member of this set of isomers, the title compound, (I), has been prepared and we report its crystal structure here. A lower-quality structure (C—C su's 0.004–0.005 Å) of the same molecule, as a toluene solvate, has recently been reported (Goryunkov et al., 2007).

The structure of (I), Figs. 1 and 2, comprises an idealized Ih C60 core with eight sp3 carbon atoms at positions 1, 6, 11, 16, 18, 24, 27, and 36 (Powell et al., 2002), each of which is attached to a CF3 group. The core sp3 carbon atoms are not adjacent to one another. The CF3 groups are arranged on a para-para-para-meta-para-meta-para ribbon of edge-sharing C6(CF3)2 hexagons (i.e., a p3mpmp overall addition pattern; see Schlegel diagram in Fig. 3). Note that the shared edges in each ribbon of hexagons are C(sp3)-C(sp2) bonds (e.g., C16—C17, C4—C18, etc.), not C(sp2)-C(sp2) bonds. Thus, any pair of adjacent hexagons along the ribbon have a common CF3 group. As in all other published structures of fullerene(CF3)n compounds, there are F···F intramolecular contacts between pairs of neighboring CF3 groups that range from 2.544 (2) to 2.641 (2) Å.

Four of the shortest cage C—C bonds in (I) are C4—C5 1.344 (3) Å, C9—C10 1.368 (3) Å, C17—C37 1.355 (3) Å, and C25—C26 1.361 (3) Å. All four are significantly shorter than the shortest C—C bond in the most precise structure of empty C60 reported to date (C60.Pt(octaethylporphyrin)), which is 1.379 (3) Å (Olmstead et al., 2003). More importantly, these bonds are pentagon-hexagon junctions, and the shortest pent-hex junction in C60.Pt(OEP) is 1.440 (3) Å (the longest pent-hex junction in C60.Pt(OEP) is 1.461 (3) Å); OEP is octaethylporphyrin).

Related literature top

For related literature, see: Goryunkov et al. (2007); Kareev et al. (2005); Kareev, Lebedkin, Miller et al. (2006); Kareev, Lebedkin, Popov et al. (2006); Olmstead et al. (2003); Popov et al. (2007); Powell et al. (2002).

Experimental top

The synthesis of (I) was carried out by heating C60 in a stream of CF3I at 460 °C as previously described (Popov et al., 2007). Crystals of the HPLC-purified compound were grown by slow evaporation of a saturated deuterochloroform solution.

Refinement top

The maximum (0.81 e Å-3) and minimum (-1.31 e Å-3) residual electron density peaks were located 0.94 and 0.70 Å, respectively, from the Cl1 atom. The deuterium atom was geometrically placed (C—D = 1.00 Å) and refined as riding with Uiso(D) = 1.2Ueq(C).

Structure description top

Recently reported high-temperature reactions of C60 with CF3I have yielded five C60(CF3)8 derivatives, with thermodynamically stable addition patterns that are asymmetric as well as unprecedented in fullerene(X)n chemistry (Kareev et al., 2005; Kareev, Lebedkin, Popov et al., 2006; Kareev, Lebedkin, Miller et al., 2006; Popov et al., 2007). A member of this set of isomers, the title compound, (I), has been prepared and we report its crystal structure here. A lower-quality structure (C—C su's 0.004–0.005 Å) of the same molecule, as a toluene solvate, has recently been reported (Goryunkov et al., 2007).

The structure of (I), Figs. 1 and 2, comprises an idealized Ih C60 core with eight sp3 carbon atoms at positions 1, 6, 11, 16, 18, 24, 27, and 36 (Powell et al., 2002), each of which is attached to a CF3 group. The core sp3 carbon atoms are not adjacent to one another. The CF3 groups are arranged on a para-para-para-meta-para-meta-para ribbon of edge-sharing C6(CF3)2 hexagons (i.e., a p3mpmp overall addition pattern; see Schlegel diagram in Fig. 3). Note that the shared edges in each ribbon of hexagons are C(sp3)-C(sp2) bonds (e.g., C16—C17, C4—C18, etc.), not C(sp2)-C(sp2) bonds. Thus, any pair of adjacent hexagons along the ribbon have a common CF3 group. As in all other published structures of fullerene(CF3)n compounds, there are F···F intramolecular contacts between pairs of neighboring CF3 groups that range from 2.544 (2) to 2.641 (2) Å.

Four of the shortest cage C—C bonds in (I) are C4—C5 1.344 (3) Å, C9—C10 1.368 (3) Å, C17—C37 1.355 (3) Å, and C25—C26 1.361 (3) Å. All four are significantly shorter than the shortest C—C bond in the most precise structure of empty C60 reported to date (C60.Pt(octaethylporphyrin)), which is 1.379 (3) Å (Olmstead et al., 2003). More importantly, these bonds are pentagon-hexagon junctions, and the shortest pent-hex junction in C60.Pt(OEP) is 1.440 (3) Å (the longest pent-hex junction in C60.Pt(OEP) is 1.461 (3) Å); OEP is octaethylporphyrin).

For related literature, see: Goryunkov et al. (2007); Kareev et al. (2005); Kareev, Lebedkin, Miller et al. (2006); Kareev, Lebedkin, Popov et al. (2006); Olmstead et al. (2003); Popov et al. (2007); Powell et al. (2002).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of (I) showing the numbering scheme. Displacement ellipsoids are shown at the 50% probability level for selected atoms.
[Figure 3] Fig. 3. Schlegel diagram of (I) showing the location of the CF3 groups as black circles, the IUPAC lowest-locant numbers for the cage carbon atoms to which they are attached, and the ribbons or loops of meta- and para-C6(CF3)2 edge-sharing hexagons (meta-C6(CF3)2 hexagons are indicated by the letter m).
1,6,11,16,18,24,27,36-Octakis(trifluoromethyl)-1,6,11,16,18,24,27,36- octahydro(C60—Ih)[5,6]fullerene deuterochloroform solvate top
Crystal data top
C68F24·CDCl3F(000) = 2728
Mr = 1393.05Dx = 2.055 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 999 reflections
a = 14.5346 (6) Åθ = 1.7–32.6°
b = 15.5805 (7) ŵ = 0.36 mm1
c = 20.1746 (9) ÅT = 100 K
β = 99.821 (2)°Plate, red
V = 4501.7 (3) Å30.34 × 0.20 × 0.05 mm
Z = 4
Data collection top
Bruker Kappa APEXII
diffractometer
16373 independent reflections
Radiation source: fine-focus sealed tube10149 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 32.6°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 2120
Tmin = 0.888, Tmax = 0.982k = 2123
99651 measured reflectionsl = 3030
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullPrimary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.054Secondary atom site location: difference Fourier map
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.0671P)2 + 3.3603P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
16373 reflectionsΔρmax = 0.81 e Å3
865 parametersΔρmin = 1.31 e Å3
Crystal data top
C68F24·CDCl3V = 4501.7 (3) Å3
Mr = 1393.05Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.5346 (6) ŵ = 0.36 mm1
b = 15.5805 (7) ÅT = 100 K
c = 20.1746 (9) Å0.34 × 0.20 × 0.05 mm
β = 99.821 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
16373 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
10149 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.982Rint = 0.058
99651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054865 parameters
wR(F2) = 0.1500 restraints
S = 1.03Δρmax = 0.81 e Å3
16373 reflectionsΔρmin = 1.31 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*/Ueq
C10.22954 (14)0.51270 (13)0.71157 (10)0.0119 (4)
C20.31195 (13)0.47443 (13)0.75999 (10)0.0122 (4)
C30.37706 (14)0.43914 (13)0.72152 (10)0.0120 (4)
C40.33256 (14)0.44155 (13)0.65064 (10)0.0124 (4)
C50.24620 (14)0.47497 (13)0.64361 (10)0.0122 (4)
C60.16767 (14)0.45221 (13)0.58603 (10)0.0122 (4)
C70.08260 (13)0.42002 (12)0.61501 (10)0.0116 (4)
C80.06967 (13)0.43661 (12)0.67850 (10)0.0119 (4)
C90.14044 (13)0.47654 (12)0.72942 (10)0.0118 (4)
C100.13275 (14)0.44108 (13)0.79026 (10)0.0119 (4)
C110.21231 (14)0.43500 (13)0.84895 (10)0.0126 (4)
C120.30475 (14)0.44021 (13)0.82144 (10)0.0126 (4)
C130.36336 (14)0.37005 (13)0.84673 (10)0.0131 (4)
C140.43056 (14)0.33913 (13)0.81079 (10)0.0131 (4)
C150.43964 (13)0.37626 (13)0.74774 (10)0.0125 (4)
C160.48223 (14)0.31089 (13)0.70478 (10)0.0138 (4)
C170.42311 (14)0.30696 (13)0.63493 (10)0.0132 (4)
C180.36765 (13)0.38418 (13)0.59986 (10)0.0125 (4)
C190.28377 (14)0.33905 (13)0.55855 (10)0.0131 (4)
C200.19455 (14)0.36916 (13)0.55264 (10)0.0129 (4)
C210.11890 (14)0.30888 (13)0.54595 (10)0.0130 (4)
C220.04858 (14)0.33898 (13)0.58249 (10)0.0127 (4)
C230.00237 (13)0.28128 (13)0.61350 (10)0.0132 (4)
C240.03997 (13)0.30422 (13)0.67805 (10)0.0120 (4)
C250.01605 (13)0.37749 (13)0.71364 (10)0.0119 (4)
C260.05413 (14)0.37925 (13)0.78009 (10)0.0121 (4)
C270.04584 (14)0.30608 (13)0.82818 (10)0.0132 (4)
C280.14437 (14)0.28551 (13)0.86735 (10)0.0133 (4)
C290.21721 (14)0.34206 (13)0.87615 (10)0.0137 (4)
C300.31094 (14)0.31034 (14)0.88086 (10)0.0138 (4)
C310.32936 (14)0.22274 (14)0.87955 (10)0.0149 (4)
C320.39982 (14)0.19058 (14)0.84261 (10)0.0149 (4)
C330.44895 (14)0.24785 (13)0.80846 (10)0.0142 (4)
C340.46981 (13)0.22705 (13)0.74309 (10)0.0136 (4)
C350.43829 (14)0.15167 (13)0.71288 (11)0.0148 (4)
C360.40829 (14)0.14344 (13)0.63628 (11)0.0152 (4)
C370.38769 (14)0.23243 (13)0.60682 (10)0.0135 (4)
C380.30168 (14)0.24885 (13)0.55832 (10)0.0137 (4)
C390.23019 (15)0.19004 (13)0.54784 (10)0.0143 (4)
C400.13594 (14)0.22051 (13)0.54197 (10)0.0136 (4)
C410.08435 (14)0.16073 (13)0.57607 (10)0.0139 (4)
C420.01719 (14)0.19157 (13)0.61230 (10)0.0137 (4)
C430.00952 (14)0.15484 (13)0.67717 (10)0.0131 (4)
C440.01543 (13)0.22188 (13)0.71973 (10)0.0128 (4)
C450.02385 (14)0.22293 (13)0.78671 (10)0.0132 (4)
C460.08854 (14)0.15709 (13)0.81393 (10)0.0141 (4)
C470.16171 (14)0.19491 (13)0.86302 (10)0.0143 (4)
C480.25307 (15)0.16337 (14)0.87047 (10)0.0155 (4)
C490.27510 (15)0.09381 (13)0.82797 (11)0.0159 (4)
C500.36617 (14)0.11167 (13)0.81069 (11)0.0153 (4)
C520.31046 (15)0.05660 (13)0.69644 (11)0.0160 (4)
C510.38363 (14)0.09373 (13)0.74610 (11)0.0159 (4)
C530.31764 (15)0.09096 (13)0.63196 (11)0.0162 (4)
C540.23746 (15)0.10979 (13)0.58680 (10)0.0153 (4)
C550.14711 (15)0.09228 (13)0.60372 (11)0.0154 (4)
C560.13946 (15)0.05629 (13)0.66603 (11)0.0156 (4)
C570.06917 (14)0.08813 (13)0.70320 (10)0.0141 (4)
C580.10952 (15)0.08903 (13)0.77358 (11)0.0151 (4)
C590.20490 (15)0.05780 (13)0.78024 (11)0.0156 (4)
C600.22246 (15)0.03785 (13)0.71339 (11)0.0158 (4)
C610.23418 (15)0.61124 (13)0.70994 (11)0.0160 (4)
C620.13984 (15)0.52462 (14)0.53379 (11)0.0169 (4)
C630.20979 (15)0.50065 (14)0.90533 (11)0.0169 (4)
C640.58647 (14)0.33052 (14)0.70584 (11)0.0166 (4)
C650.42188 (15)0.43631 (14)0.55408 (11)0.0177 (4)
C660.14472 (14)0.32420 (13)0.66104 (10)0.0135 (4)
C670.02525 (15)0.32071 (14)0.87504 (10)0.0155 (4)
C680.47841 (15)0.09581 (14)0.60102 (12)0.0188 (4)
C690.68341 (18)0.30051 (17)0.98786 (14)0.0290 (5)
D6910.68580.32191.03490.035*
Cl10.62123 (6)0.37552 (5)0.93253 (4)0.0537 (2)
Cl20.62609 (6)0.20279 (5)0.98064 (6)0.0564 (2)
Cl30.79819 (5)0.29047 (5)0.97296 (4)0.04089 (18)
F6110.31448 (10)0.63788 (8)0.69331 (8)0.0255 (3)
F6120.22776 (10)0.64561 (8)0.76941 (7)0.0252 (3)
F6130.16494 (10)0.64384 (9)0.66515 (7)0.0264 (3)
F6210.21276 (10)0.57120 (9)0.52435 (7)0.0278 (3)
F6220.07730 (10)0.57817 (9)0.55216 (7)0.0279 (3)
F6230.10111 (11)0.49154 (9)0.47448 (7)0.0278 (3)
F6310.28373 (10)0.49032 (9)0.95411 (7)0.0271 (3)
F6320.13408 (11)0.49217 (11)0.93358 (8)0.0332 (4)
F6330.21160 (11)0.58085 (9)0.88351 (7)0.0271 (3)
F6410.62551 (9)0.27344 (9)0.67054 (8)0.0265 (3)
F6420.63347 (9)0.32981 (10)0.76843 (7)0.0282 (3)
F6430.59864 (9)0.40800 (9)0.68020 (8)0.0267 (3)
F6510.46681 (12)0.38468 (10)0.51812 (8)0.0378 (4)
F6520.48295 (10)0.48998 (10)0.58856 (8)0.0323 (4)
F6530.36383 (10)0.48368 (10)0.51031 (7)0.0279 (3)
F6610.15923 (9)0.39304 (8)0.62046 (7)0.0201 (3)
F6620.18186 (8)0.34158 (9)0.71544 (6)0.0182 (3)
F6630.19178 (8)0.25846 (8)0.62891 (6)0.0186 (3)
F6710.00442 (10)0.38995 (9)0.91402 (7)0.0227 (3)
F6720.02650 (9)0.25319 (9)0.91616 (6)0.0193 (3)
F6730.11104 (9)0.33158 (9)0.84072 (6)0.0213 (3)
F6810.49604 (9)0.01739 (9)0.62755 (7)0.0248 (3)
F6820.56018 (9)0.13640 (9)0.60644 (8)0.0271 (3)
F6830.44498 (10)0.08603 (9)0.53539 (7)0.0259 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0119 (9)0.0102 (8)0.0136 (9)0.0004 (7)0.0017 (7)0.0007 (7)
C20.0099 (8)0.0116 (9)0.0146 (9)0.0026 (7)0.0002 (7)0.0015 (7)
C30.0111 (9)0.0114 (9)0.0133 (9)0.0035 (7)0.0016 (7)0.0012 (7)
C40.0127 (9)0.0109 (9)0.0136 (9)0.0034 (7)0.0023 (7)0.0011 (7)
C50.0120 (9)0.0114 (9)0.0136 (9)0.0012 (7)0.0032 (7)0.0030 (7)
C60.0124 (9)0.0127 (9)0.0116 (9)0.0013 (7)0.0018 (7)0.0028 (7)
C70.0093 (8)0.0113 (9)0.0135 (9)0.0008 (7)0.0004 (7)0.0038 (7)
C80.0095 (8)0.0107 (9)0.0149 (9)0.0014 (7)0.0002 (7)0.0015 (7)
C90.0099 (8)0.0104 (9)0.0149 (9)0.0005 (7)0.0012 (7)0.0002 (7)
C100.0114 (9)0.0118 (9)0.0123 (9)0.0001 (7)0.0016 (7)0.0021 (7)
C110.0125 (9)0.0138 (9)0.0113 (8)0.0018 (7)0.0012 (7)0.0017 (7)
C120.0117 (9)0.0116 (9)0.0140 (9)0.0037 (7)0.0006 (7)0.0038 (7)
C130.0127 (9)0.0141 (9)0.0115 (9)0.0028 (7)0.0008 (7)0.0005 (7)
C140.0097 (9)0.0138 (9)0.0144 (9)0.0015 (7)0.0016 (7)0.0001 (7)
C150.0080 (8)0.0138 (9)0.0154 (9)0.0027 (7)0.0011 (7)0.0005 (7)
C160.0103 (9)0.0138 (9)0.0169 (9)0.0014 (7)0.0010 (7)0.0004 (7)
C170.0103 (9)0.0152 (9)0.0149 (9)0.0006 (7)0.0039 (7)0.0006 (7)
C180.0105 (9)0.0149 (9)0.0127 (9)0.0006 (7)0.0038 (7)0.0018 (7)
C190.0143 (9)0.0169 (10)0.0090 (8)0.0017 (7)0.0041 (7)0.0006 (7)
C200.0154 (9)0.0142 (9)0.0089 (8)0.0008 (7)0.0019 (7)0.0014 (7)
C210.0120 (9)0.0185 (10)0.0083 (8)0.0011 (7)0.0007 (7)0.0002 (7)
C220.0107 (9)0.0169 (10)0.0096 (8)0.0002 (7)0.0010 (7)0.0007 (7)
C230.0090 (8)0.0169 (10)0.0124 (9)0.0008 (7)0.0015 (7)0.0003 (7)
C240.0085 (8)0.0126 (9)0.0148 (9)0.0016 (7)0.0016 (7)0.0011 (7)
C250.0096 (8)0.0125 (9)0.0138 (9)0.0005 (7)0.0030 (7)0.0004 (7)
C260.0108 (8)0.0137 (9)0.0127 (9)0.0008 (7)0.0041 (7)0.0009 (7)
C270.0115 (9)0.0166 (9)0.0116 (9)0.0011 (7)0.0027 (7)0.0014 (7)
C280.0146 (9)0.0171 (10)0.0085 (8)0.0012 (7)0.0029 (7)0.0014 (7)
C290.0157 (9)0.0164 (10)0.0086 (8)0.0010 (8)0.0011 (7)0.0005 (7)
C300.0134 (9)0.0180 (10)0.0087 (8)0.0018 (7)0.0014 (7)0.0002 (7)
C310.0141 (9)0.0180 (10)0.0111 (9)0.0003 (8)0.0017 (7)0.0031 (7)
C320.0124 (9)0.0158 (10)0.0149 (9)0.0025 (7)0.0021 (7)0.0038 (7)
C330.0098 (9)0.0157 (9)0.0153 (9)0.0005 (7)0.0030 (7)0.0023 (7)
C340.0073 (8)0.0148 (9)0.0181 (9)0.0021 (7)0.0002 (7)0.0031 (8)
C350.0116 (9)0.0143 (9)0.0181 (10)0.0033 (7)0.0010 (7)0.0010 (8)
C360.0131 (9)0.0130 (9)0.0194 (10)0.0011 (7)0.0027 (8)0.0015 (8)
C370.0108 (9)0.0160 (9)0.0145 (9)0.0003 (7)0.0043 (7)0.0005 (7)
C380.0136 (9)0.0169 (9)0.0110 (8)0.0004 (7)0.0037 (7)0.0013 (7)
C390.0156 (9)0.0158 (10)0.0121 (9)0.0002 (7)0.0037 (7)0.0045 (7)
C400.0138 (9)0.0170 (10)0.0097 (8)0.0017 (7)0.0013 (7)0.0020 (7)
C410.0117 (9)0.0159 (9)0.0132 (9)0.0036 (7)0.0006 (7)0.0031 (7)
C420.0099 (9)0.0156 (9)0.0147 (9)0.0034 (7)0.0003 (7)0.0033 (7)
C430.0101 (9)0.0129 (9)0.0159 (9)0.0040 (7)0.0006 (7)0.0002 (7)
C440.0092 (8)0.0136 (9)0.0161 (9)0.0024 (7)0.0034 (7)0.0002 (7)
C450.0111 (9)0.0131 (9)0.0158 (9)0.0033 (7)0.0038 (7)0.0009 (7)
C460.0133 (9)0.0142 (9)0.0149 (9)0.0033 (7)0.0031 (7)0.0031 (7)
C470.0152 (9)0.0163 (10)0.0118 (9)0.0023 (8)0.0034 (7)0.0045 (7)
C480.0166 (10)0.0171 (10)0.0118 (9)0.0006 (8)0.0000 (7)0.0067 (7)
C490.0171 (10)0.0128 (9)0.0168 (10)0.0003 (7)0.0001 (8)0.0057 (8)
C500.0139 (9)0.0122 (9)0.0184 (10)0.0022 (7)0.0013 (8)0.0057 (8)
C520.0159 (10)0.0101 (9)0.0214 (10)0.0014 (7)0.0015 (8)0.0014 (8)
C510.0136 (9)0.0111 (9)0.0220 (10)0.0030 (7)0.0004 (8)0.0022 (8)
C530.0157 (10)0.0109 (9)0.0224 (10)0.0006 (7)0.0040 (8)0.0039 (8)
C540.0160 (10)0.0137 (9)0.0166 (9)0.0002 (7)0.0039 (8)0.0049 (7)
C550.0152 (9)0.0115 (9)0.0184 (10)0.0021 (7)0.0005 (8)0.0043 (7)
C560.0162 (10)0.0095 (9)0.0207 (10)0.0030 (7)0.0020 (8)0.0025 (8)
C570.0131 (9)0.0106 (9)0.0182 (10)0.0041 (7)0.0017 (7)0.0005 (7)
C580.0160 (10)0.0111 (9)0.0181 (10)0.0025 (7)0.0029 (8)0.0040 (7)
C590.0153 (10)0.0109 (9)0.0202 (10)0.0007 (7)0.0019 (8)0.0047 (8)
C600.0178 (10)0.0081 (9)0.0211 (10)0.0008 (7)0.0021 (8)0.0000 (7)
C610.0149 (9)0.0125 (9)0.0214 (10)0.0003 (7)0.0051 (8)0.0010 (8)
C620.0153 (10)0.0186 (10)0.0162 (10)0.0014 (8)0.0008 (8)0.0056 (8)
C630.0169 (10)0.0181 (10)0.0158 (9)0.0022 (8)0.0028 (8)0.0030 (8)
C640.0117 (9)0.0157 (10)0.0228 (10)0.0001 (7)0.0040 (8)0.0005 (8)
C650.0155 (10)0.0189 (10)0.0196 (10)0.0013 (8)0.0060 (8)0.0025 (8)
C660.0101 (9)0.0152 (9)0.0147 (9)0.0012 (7)0.0012 (7)0.0000 (7)
C670.0159 (10)0.0178 (10)0.0131 (9)0.0021 (8)0.0031 (7)0.0013 (8)
C680.0162 (10)0.0161 (10)0.0247 (11)0.0013 (8)0.0049 (8)0.0029 (8)
C690.0256 (12)0.0289 (13)0.0322 (13)0.0020 (10)0.0040 (10)0.0001 (11)
Cl10.0641 (5)0.0305 (4)0.0525 (5)0.0121 (3)0.0302 (4)0.0050 (3)
Cl20.0327 (4)0.0348 (4)0.1032 (8)0.0068 (3)0.0158 (4)0.0022 (4)
Cl30.0261 (3)0.0569 (5)0.0438 (4)0.0025 (3)0.0176 (3)0.0046 (3)
F6110.0221 (7)0.0147 (6)0.0430 (8)0.0057 (5)0.0150 (6)0.0004 (6)
F6120.0369 (8)0.0144 (6)0.0260 (7)0.0014 (6)0.0104 (6)0.0060 (5)
F6130.0263 (7)0.0165 (6)0.0343 (8)0.0046 (5)0.0013 (6)0.0071 (6)
F6210.0191 (7)0.0282 (8)0.0344 (8)0.0077 (6)0.0001 (6)0.0177 (6)
F6220.0296 (8)0.0238 (7)0.0313 (8)0.0124 (6)0.0080 (6)0.0124 (6)
F6230.0379 (8)0.0251 (7)0.0164 (6)0.0038 (6)0.0074 (6)0.0063 (5)
F6310.0291 (8)0.0303 (8)0.0177 (6)0.0015 (6)0.0075 (6)0.0080 (6)
F6320.0291 (8)0.0420 (9)0.0328 (8)0.0133 (7)0.0182 (7)0.0217 (7)
F6330.0440 (9)0.0151 (6)0.0218 (7)0.0016 (6)0.0045 (6)0.0037 (5)
F6410.0128 (6)0.0263 (7)0.0421 (8)0.0010 (5)0.0091 (6)0.0121 (6)
F6420.0140 (6)0.0456 (9)0.0231 (7)0.0055 (6)0.0023 (5)0.0012 (6)
F6430.0161 (6)0.0197 (7)0.0451 (9)0.0042 (5)0.0071 (6)0.0073 (6)
F6510.0480 (10)0.0303 (8)0.0457 (10)0.0067 (7)0.0385 (8)0.0066 (7)
F6520.0276 (8)0.0387 (9)0.0296 (8)0.0201 (7)0.0017 (6)0.0085 (7)
F6530.0258 (7)0.0323 (8)0.0256 (7)0.0016 (6)0.0042 (6)0.0164 (6)
F6610.0151 (6)0.0218 (7)0.0227 (7)0.0026 (5)0.0008 (5)0.0084 (5)
F6620.0120 (6)0.0260 (7)0.0169 (6)0.0010 (5)0.0039 (5)0.0018 (5)
F6630.0114 (6)0.0203 (6)0.0226 (6)0.0046 (5)0.0008 (5)0.0043 (5)
F6710.0252 (7)0.0234 (7)0.0219 (7)0.0044 (6)0.0109 (5)0.0073 (5)
F6720.0182 (6)0.0238 (7)0.0171 (6)0.0014 (5)0.0069 (5)0.0055 (5)
F6730.0125 (6)0.0342 (8)0.0173 (6)0.0025 (5)0.0028 (5)0.0042 (5)
F6810.0211 (7)0.0169 (6)0.0360 (8)0.0066 (5)0.0036 (6)0.0026 (6)
F6820.0149 (6)0.0264 (7)0.0425 (9)0.0024 (5)0.0120 (6)0.0114 (6)
F6830.0256 (7)0.0288 (8)0.0237 (7)0.0048 (6)0.0053 (6)0.0076 (6)
Geometric parameters (Å, º) top
C1—C91.511 (3)C35—C511.441 (3)
C1—C21.532 (3)C35—C361.538 (3)
C1—C611.537 (3)C36—C371.518 (3)
C1—C51.548 (3)C36—C681.531 (3)
C2—C121.370 (3)C36—C531.540 (3)
C2—C31.432 (3)C37—C381.473 (3)
C3—C151.379 (3)C38—C391.374 (3)
C3—C41.466 (3)C39—C401.436 (3)
C4—C51.344 (3)C39—C541.471 (3)
C4—C181.512 (3)C40—C411.442 (3)
C5—C61.525 (3)C41—C421.400 (3)
C6—C71.539 (3)C41—C551.452 (3)
C6—C201.540 (3)C42—C431.450 (3)
C6—C621.550 (3)C43—C571.397 (3)
C7—C81.351 (3)C43—C441.437 (3)
C7—C221.469 (3)C44—C451.375 (3)
C8—C91.463 (3)C45—C461.436 (3)
C8—C251.465 (3)C46—C581.402 (3)
C9—C101.368 (3)C46—C471.449 (3)
C10—C261.482 (3)C47—C481.400 (3)
C10—C111.510 (3)C48—C491.451 (3)
C11—C631.535 (3)C49—C591.396 (3)
C11—C121.541 (3)C49—C501.452 (3)
C11—C291.546 (3)C50—C511.398 (3)
C12—C131.426 (3)C52—C601.410 (3)
C13—C141.398 (3)C52—C531.427 (3)
C13—C301.449 (3)C52—C511.451 (3)
C14—C151.424 (3)C53—C541.383 (3)
C14—C331.449 (3)C54—C551.438 (3)
C15—C161.535 (3)C55—C561.398 (3)
C16—C171.521 (3)C56—C601.434 (3)
C16—C641.542 (3)C56—C571.454 (3)
C16—C341.544 (3)C57—C581.441 (3)
C17—C371.355 (3)C58—C591.454 (3)
C17—C181.550 (3)C59—C601.448 (3)
C18—C191.526 (3)C61—F6121.332 (2)
C18—C651.544 (3)C61—F6131.333 (2)
C19—C201.365 (3)C61—F6111.334 (2)
C19—C381.429 (3)C62—F6211.325 (2)
C20—C211.435 (3)C62—F6221.332 (3)
C21—C401.404 (3)C62—F6231.336 (3)
C21—C221.437 (3)C63—F6331.327 (3)
C22—C231.381 (3)C63—F6321.329 (3)
C23—C421.427 (3)C63—F6311.337 (3)
C23—C241.538 (3)C64—F6411.326 (2)
C24—C251.511 (3)C64—F6421.329 (3)
C24—C661.534 (3)C64—F6431.337 (3)
C24—C441.542 (3)C65—F6521.327 (3)
C25—C261.361 (3)C65—F6511.327 (3)
C26—C271.515 (3)C65—F6531.335 (3)
C27—C671.532 (3)C66—F6621.331 (2)
C27—C451.546 (3)C66—F6631.336 (2)
C27—C281.547 (3)C66—F6611.344 (2)
C28—C291.366 (3)C67—F6731.330 (2)
C28—C471.439 (3)C67—F6711.339 (2)
C29—C301.437 (3)C67—F6721.342 (2)
C30—C311.392 (3)C68—F6821.334 (3)
C31—C481.432 (3)C68—F6831.339 (3)
C31—C321.455 (3)C68—F6811.341 (3)
C32—C331.396 (3)C69—Cl21.730 (3)
C32—C501.435 (3)C69—Cl31.752 (3)
C33—C341.440 (3)C69—Cl11.756 (3)
C34—C351.366 (3)
C9—C1—C2108.16 (16)C68—C36—C35114.22 (17)
C9—C1—C61114.83 (16)C37—C36—C53110.66 (17)
C2—C1—C61111.72 (16)C68—C36—C53110.32 (17)
C9—C1—C5109.83 (16)C35—C36—C53101.20 (17)
C2—C1—C5101.17 (15)C17—C37—C38110.38 (18)
C61—C1—C5110.26 (16)C17—C37—C36125.69 (18)
C12—C2—C3120.04 (18)C38—C37—C36120.48 (18)
C12—C2—C1123.83 (18)C39—C38—C19121.51 (19)
C3—C2—C1108.72 (17)C39—C38—C37121.35 (19)
C15—C3—C2121.22 (18)C19—C38—C37107.64 (17)
C15—C3—C4122.99 (18)C38—C39—C40118.56 (19)
C2—C3—C4107.25 (17)C38—C39—C54120.06 (19)
C5—C4—C3111.20 (18)C40—C39—C54107.80 (18)
C5—C4—C18125.05 (18)C21—C40—C39119.66 (18)
C3—C4—C18120.14 (17)C21—C40—C41119.67 (18)
C4—C5—C6123.67 (18)C39—C40—C41108.28 (18)
C4—C5—C1109.75 (17)C42—C41—C40119.53 (19)
C6—C5—C1123.58 (17)C42—C41—C55119.99 (19)
C5—C6—C7109.37 (16)C40—C41—C55108.30 (18)
C5—C6—C20108.41 (16)C41—C42—C23120.23 (19)
C7—C6—C2099.94 (15)C41—C42—C43120.22 (19)
C5—C6—C62115.05 (17)C23—C42—C43108.96 (17)
C7—C6—C62111.23 (16)C57—C43—C44121.31 (18)
C20—C6—C62111.75 (16)C57—C43—C42119.63 (18)
C8—C7—C22119.81 (18)C44—C43—C42108.57 (17)
C8—C7—C6123.27 (18)C45—C44—C43119.42 (19)
C22—C7—C6109.96 (16)C45—C44—C24123.01 (18)
C7—C8—C9123.53 (18)C43—C44—C24109.71 (17)
C7—C8—C25120.66 (18)C44—C45—C46120.17 (19)
C9—C8—C25107.21 (17)C44—C45—C27123.71 (18)
C10—C9—C8107.64 (17)C46—C45—C27109.29 (17)
C10—C9—C1124.68 (18)C58—C46—C45120.77 (19)
C8—C9—C1121.32 (17)C58—C46—C47119.84 (19)
C9—C10—C26108.51 (17)C45—C46—C47109.10 (18)
C9—C10—C11124.05 (18)C48—C47—C28120.70 (19)
C26—C10—C11122.48 (17)C48—C47—C46120.18 (19)
C10—C11—C63115.30 (17)C28—C47—C46108.95 (18)
C10—C11—C12108.21 (16)C47—C48—C31119.13 (19)
C63—C11—C12111.37 (16)C47—C48—C49119.98 (19)
C10—C11—C29108.65 (16)C31—C48—C49108.30 (18)
C63—C11—C29111.50 (16)C59—C49—C48119.92 (19)
C12—C11—C29100.78 (16)C59—C49—C50120.0 (2)
C2—C12—C13119.29 (18)C48—C49—C50107.51 (18)
C2—C12—C11123.53 (18)C51—C50—C32119.18 (19)
C13—C12—C11109.58 (17)C51—C50—C49120.23 (19)
C14—C13—C12120.41 (18)C32—C50—C49108.15 (18)
C14—C13—C30119.73 (19)C60—C52—C53120.63 (19)
C12—C13—C30109.39 (18)C60—C52—C51120.24 (19)
C13—C14—C15120.20 (18)C53—C52—C51108.71 (18)
C13—C14—C33120.27 (18)C50—C51—C35120.70 (19)
C15—C14—C33108.90 (18)C50—C51—C52119.68 (19)
C3—C15—C14118.40 (18)C35—C51—C52109.03 (18)
C3—C15—C16123.91 (18)C54—C53—C52119.7 (2)
C14—C15—C16110.05 (17)C54—C53—C36122.77 (19)
C17—C16—C15109.35 (16)C52—C53—C36110.03 (18)
C17—C16—C64114.79 (17)C53—C54—C55120.30 (19)
C15—C16—C64110.52 (16)C53—C54—C39120.53 (19)
C17—C16—C34109.50 (16)C55—C54—C39107.62 (18)
C15—C16—C34100.71 (16)C56—C55—C54120.36 (19)
C64—C16—C34111.06 (16)C56—C55—C41119.94 (19)
C37—C17—C16122.44 (18)C54—C55—C41107.99 (18)
C37—C17—C18110.07 (17)C55—C56—C60119.50 (19)
C16—C17—C18124.00 (17)C55—C56—C57119.84 (19)
C4—C18—C19108.18 (16)C60—C56—C57108.06 (18)
C4—C18—C65111.10 (17)C43—C57—C58119.03 (19)
C19—C18—C65110.96 (16)C43—C57—C56120.37 (19)
C4—C18—C17111.02 (16)C58—C57—C56107.93 (18)
C19—C18—C17101.33 (16)C46—C58—C57119.17 (19)
C65—C18—C17113.74 (16)C46—C58—C59119.87 (19)
C20—C19—C38120.56 (19)C57—C58—C59108.02 (18)
C20—C19—C18123.22 (18)C49—C59—C60120.29 (19)
C38—C19—C18109.02 (17)C49—C59—C58120.18 (19)
C19—C20—C21118.99 (19)C60—C59—C58107.61 (18)
C19—C20—C6123.97 (18)C52—C60—C56119.45 (19)
C21—C20—C6110.10 (17)C52—C60—C59119.52 (19)
C40—C21—C20120.50 (18)C56—C60—C59108.39 (18)
C40—C21—C22119.83 (18)F612—C61—F613107.26 (17)
C20—C21—C22109.81 (18)F612—C61—F611107.46 (17)
C23—C22—C21120.22 (19)F613—C61—F611107.62 (17)
C23—C22—C7121.54 (18)F612—C61—C1111.86 (17)
C21—C22—C7107.15 (17)F613—C61—C1111.36 (17)
C22—C23—C42120.41 (19)F611—C61—C1111.06 (17)
C22—C23—C24121.86 (18)F621—C62—F622107.31 (18)
C42—C23—C24110.04 (17)F621—C62—F623107.92 (17)
C25—C24—C66112.75 (16)F622—C62—F623106.71 (17)
C25—C24—C23109.74 (16)F621—C62—C6111.97 (17)
C66—C24—C23109.89 (16)F622—C62—C6112.22 (17)
C25—C24—C44108.28 (16)F623—C62—C6110.46 (17)
C66—C24—C44114.77 (16)F633—C63—F632107.49 (18)
C23—C24—C44100.71 (16)F633—C63—F631107.37 (17)
C26—C25—C8107.67 (17)F632—C63—F631107.01 (18)
C26—C25—C24125.40 (18)F633—C63—C11112.18 (17)
C8—C25—C24122.21 (17)F632—C63—C11112.20 (17)
C25—C26—C10108.90 (17)F631—C63—C11110.33 (17)
C25—C26—C27123.53 (18)F641—C64—F642107.87 (17)
C10—C26—C27122.97 (17)F641—C64—F643107.51 (18)
C26—C27—C67114.77 (17)F642—C64—F643107.14 (18)
C26—C27—C45108.41 (16)F641—C64—C16111.64 (17)
C67—C27—C45111.08 (16)F642—C64—C16110.86 (17)
C26—C27—C28108.38 (16)F643—C64—C16111.61 (17)
C67—C27—C28112.26 (16)F652—C65—F651108.73 (18)
C45—C27—C28101.00 (16)F652—C65—F653106.81 (18)
C29—C28—C47120.06 (19)F651—C65—F653106.74 (18)
C29—C28—C27124.23 (18)F652—C65—C18112.46 (18)
C47—C28—C27109.19 (17)F651—C65—C18110.93 (18)
C28—C29—C30119.46 (19)F653—C65—C18110.92 (17)
C28—C29—C11124.79 (18)F662—C66—F663108.05 (16)
C30—C29—C11109.35 (17)F662—C66—F661107.23 (16)
C31—C30—C29121.28 (19)F663—C66—F661107.58 (16)
C31—C30—C13120.15 (19)F662—C66—C24112.55 (16)
C29—C30—C13108.49 (18)F663—C66—C24111.05 (16)
C30—C31—C48119.26 (19)F661—C66—C24110.17 (16)
C30—C31—C32120.13 (19)F673—C67—F671107.52 (18)
C48—C31—C32108.03 (18)F673—C67—F672108.14 (17)
C33—C32—C50119.37 (19)F671—C67—F672107.09 (16)
C33—C32—C31119.78 (19)F673—C67—C27111.66 (16)
C50—C32—C31108.01 (18)F671—C67—C27111.94 (17)
C32—C33—C34120.90 (19)F672—C67—C27110.29 (17)
C32—C33—C14119.91 (19)F682—C68—F683107.64 (18)
C34—C33—C14108.63 (18)F682—C68—F681107.00 (18)
C35—C34—C33119.69 (19)F683—C68—F681107.66 (18)
C35—C34—C16124.27 (19)F682—C68—C36112.74 (18)
C33—C34—C16109.21 (17)F683—C68—C36110.89 (18)
C34—C35—C51120.05 (19)F681—C68—C36110.69 (18)
C34—C35—C36122.42 (19)Cl2—C69—Cl3111.47 (15)
C51—C35—C36109.31 (18)Cl2—C69—Cl1110.11 (15)
C37—C36—C68111.31 (17)Cl3—C69—Cl1110.62 (15)
C37—C36—C35108.69 (17)

Experimental details

Crystal data
Chemical formulaC68F24·CDCl3
Mr1393.05
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)14.5346 (6), 15.5805 (7), 20.1746 (9)
β (°) 99.821 (2)
V3)4501.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.34 × 0.20 × 0.05
Data collection
DiffractometerBruker Kappa APEXII
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.888, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
99651, 16373, 10149
Rint0.058
(sin θ/λ)max1)0.758
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.150, 1.03
No. of reflections16373
No. of parameters865
Δρmax, Δρmin (e Å3)0.81, 1.31

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

 

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