organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1,3,7,10,14,17,21,28,31,42,52,55-Dodeca­kis(tri­fluoro­meth­yl)- 1,3,7,10,14,17,21,28,31,42,52,55-dodeca­hydro­(C60Ih)[5,6]fullerene

aDepartment of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA, bInstitute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka 142432, Russian Federation, and cForschungszentrum Karlsruhe, Institute for Nanotechnology, Karlsruhe 76021, Germany
*Correspondence e-mail: steven.strauss@colostate.edu

(Received 22 November 2007; accepted 26 November 2007; online 6 December 2007)

The title compound, C72F36, is one of four isomers of C60(CF3)12 for which crystal structures have been obtained. The fullerene mol­ecule has an idealized Ih C60 core with the 12 CF3 groups arranged in an asymmetric fashion on two ribbons of edge-sharing C6(CF3)2 hexa­gons, a parametaparaparaparametapara ribbon and a parametapara ribbon, giving an overall pmp3mp,pmp structure. There are no cage Csp3—Csp3 bonds. The F atoms of two CF3 groups are disordered over two positions; the site occupancy factors are 0.85/0.15 and 0.73/0.27. There are intra­molecular F⋯F contacts between pairs of CF3 groups on the same hexa­gon that range from 2.521 (3) to 2.738 (4) Å.

Related literature

For related literature, see: Kareev et al. (2005[Kareev, I. E., Kuvychko, I. V., Lebedkin, S. F., Miller, S. M., Anderson, O. P., Seppelt, K., Strauss, S. H. & Boltalina, O. V. (2005). J. Am. Chem. Soc. 127, 8362-8375.], 2007[Kareev, I. E., Shustova, N. B., Peyshkov, D. V., Lebedkin, S. F., Miller, S. M., Anderson, O. P., Popov, A. A., Boltalina, O. V. & Strauss, S. H. (2007). Chem. Commun. pp. 1650-1652.]); Omelyanyuk et al. (2007[Omelyanyuk, N. A., Goryunkov, A. A., Tamm, N. B., Avdoshenko, S. M., Ioffe, I. N., Sidorov, L. N., Kemnitz, E. & Troyanov, S. I. (2007). Chem. Commun. pp.4794-4796.]); Popov et al. (2007[Popov, A. A., Kareev, I. E., Shustova, N. B., Stukalin, E. B., Lebedkin, S. F., Seppelt, K., Strauss, S. H., Boltalina, O. V. & Dunsch, L. (2007). J. Am. Chem. Soc. 129, 11551-11568.]); Powell et al. (2002[Powell, W. H., Cozzi, F., Moss, G. P., Thilgen, C., Hwu, R. J.-R. & Yerin, A. (2002). Pure Appl. Chem. 74, 629-695.]); Troyanov et al. (2006[Troyanov, S. I., Dimitrov, A. & Kemnitz, E. (2006). Angew. Chem. Int. Ed. 45, 1971-1974.]).

[Scheme 1]

Experimental

Crystal data
  • C72F36

  • Mr = 1548.72

  • Monoclinic, P 21 /n

  • a = 12.2475 (2) Å

  • b = 20.0326 (4) Å

  • c = 20.3782 (4) Å

  • β = 90.288 (1)°

  • V = 4999.71 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 100 (1) K

  • 0.13 × 0.10 × 0.08 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.982

  • 123040 measured reflections

  • 10625 independent reflections

  • 6628 reflections with I > 2σ(I)

  • Rint = 0.079

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.160

  • S = 1.03

  • 10625 reflections

  • 1030 parameters

  • 24 restraints

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2000[Bruker (2000). APEX2 (Version 2.10) and SHELXTL (Version 6.14). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Bruker, 2000[Bruker (2000). APEX2 (Version 2.10) and SHELXTL (Version 6.14). Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Four isomers of C60(CF3)12 have now been isolated and characterized by X-ray structure crystallography (Troyanov et al., 2006; Kareev et al., 2007; Popov et al., 2007; Omelyanyuk et al., 2007).

The structure of C1-pmp3mp,pmp-C60(CF3)12 has an idealized Ih C60 core with twelve sp3 carbon atoms at positions 1,3,7,10,14,17,21,28,31,42,52,and 55 (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-meta-para ribbon and a para-meta-para ribbon of edge-sharing C6(CF3)2 hexagons (i.e., a pmp3mp,pmp overall addition pattern; see Schlegel diagram in Figure 1).

The two CF3 groups attached to C1 and C7 are disordered (F atom occupancies are 73:27 for the CF3 group attached to C1 and 85:15 for the CF3 group attached to C7). Only the 73/85 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 2.521 (3) to 2.738 (4) Å. The range of C—F distances that do not involve the disordered CF3 groups is from 1.301 (5) to 1.341 (5) Å.

Related literature top

For related literature, see: Kareev et al. (2005, 2007); Omelyanyuk et al. (2007); Popov et al. (2007); Powell et al. (2002); Troyanov et al. (2006).

Experimental top

The synthesis of C1-pmp3mp,pmp-C60(CF3)12 was carried out by heating of C60 in the stream of CF3I at 500 °C during two hours as previously described (Kareev et al., 2005). The red crystals of the HPLC-purified compound were grown by slow evaporation of toluene/heptane saturated solution.

Refinement top

The maximum (0.47 e/Å3) and minimum (-0.32 e/Å3) residual electron density peaks were located 0.98 Å from F693 and 0.81 Å from F633.

Structure description top

Four isomers of C60(CF3)12 have now been isolated and characterized by X-ray structure crystallography (Troyanov et al., 2006; Kareev et al., 2007; Popov et al., 2007; Omelyanyuk et al., 2007).

The structure of C1-pmp3mp,pmp-C60(CF3)12 has an idealized Ih C60 core with twelve sp3 carbon atoms at positions 1,3,7,10,14,17,21,28,31,42,52,and 55 (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-meta-para ribbon and a para-meta-para ribbon of edge-sharing C6(CF3)2 hexagons (i.e., a pmp3mp,pmp overall addition pattern; see Schlegel diagram in Figure 1).

The two CF3 groups attached to C1 and C7 are disordered (F atom occupancies are 73:27 for the CF3 group attached to C1 and 85:15 for the CF3 group attached to C7). Only the 73/85 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 2.521 (3) to 2.738 (4) Å. The range of C—F distances that do not involve the disordered CF3 groups is from 1.301 (5) to 1.341 (5) Å.

For related literature, see: Kareev et al. (2005, 2007); Omelyanyuk et al. (2007); Popov et al. (2007); Powell et al. (2002); Troyanov et al. (2006).

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. (Left) Schlegel diagram of 1,3,7,10,14,17,21,28,31,42,52,55-C60(CF3)12 showing the IUPAC lowest-locants for the cage carbon atoms to which the CF3 groups are attached. (Right) The molecular structure of 1,3,7,10,14,17,21,28,31,42,52,55-C60(CF3)12. Displacement ellipsoids for selected atoms are shown at the 50% probability level.
[Figure 2] Fig. 2. Schlegel diagrams for the three other isomers of C60(CF3)12.
1,3,7,10,14,17,21,28,31,42,52,55-Dodecakis(trifluoromethyl)- 1,3,7,10,14,17,21,28,31,42,52,55-dodecahydro(C60—Ih)[5,6]fullerene top
Crystal data top
C72F36F(000) = 3024
Mr = 1548.72Dx = 2.057 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.2475 (2) ÅCell parameters from 9667 reflections
b = 20.0326 (4) Åθ = 1.9–26.7°
c = 20.3782 (4) ŵ = 0.22 mm1
β = 90.288 (1)°T = 100 K
V = 4999.71 (16) Å3Plate, red
Z = 40.13 × 0.10 × 0.08 mm
Data collection top
Bruker Kappa APEXII
diffractometer
10625 independent reflections
Radiation source: fine-focus sealed tube6628 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
Detector resolution: 0 pixels mm-1θmax = 26.7°, θmin = 1.9°
φ and ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 2525
Tmin = 0.973, Tmax = 0.982l = 2525
123040 measured reflections
Refinement top
Refinement on F224 restraints
Least-squares matrix: fullPrimary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.059Secondary atom site location: difference Fourier map
wR(F2) = 0.160 w = 1/[σ2(Fo2) + (0.0661P)2 + 8.0347P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
10625 reflectionsΔρmax = 0.47 e Å3
1030 parametersΔρmin = 0.32 e Å3
Crystal data top
C72F36V = 4999.71 (16) Å3
Mr = 1548.72Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.2475 (2) ŵ = 0.22 mm1
b = 20.0326 (4) ÅT = 100 K
c = 20.3782 (4) Å0.13 × 0.10 × 0.08 mm
β = 90.288 (1)°
Data collection top
Bruker Kappa APEXII
diffractometer
10625 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
6628 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.982Rint = 0.079
123040 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0591030 parameters
wR(F2) = 0.16024 restraints
S = 1.03Δρmax = 0.47 e Å3
10625 reflectionsΔρmin = 0.32 e Å3
Special details top

Experimental. none

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)
C10.4855 (3)0.67541 (16)0.32301 (18)0.0281 (8)
C20.5362 (3)0.65158 (16)0.25856 (18)0.0261 (8)
C30.4941 (3)0.69245 (16)0.19950 (18)0.0270 (8)
C40.3812 (3)0.71086 (15)0.22733 (18)0.0263 (8)
C50.3759 (3)0.70147 (16)0.29550 (18)0.0265 (8)
C60.2766 (3)0.69039 (16)0.32575 (19)0.0288 (8)
C70.2638 (3)0.64990 (17)0.38908 (19)0.0309 (8)
C80.3618 (3)0.60429 (18)0.39386 (18)0.0291 (8)
C90.4609 (3)0.61651 (18)0.36757 (18)0.0304 (8)
C100.5318 (3)0.55292 (17)0.37014 (19)0.0296 (8)
C110.5710 (3)0.53723 (17)0.30263 (18)0.0272 (8)
C120.5744 (3)0.58830 (16)0.25145 (18)0.0255 (8)
C130.5778 (3)0.55262 (16)0.18887 (18)0.0256 (8)
C140.5478 (3)0.58606 (16)0.12551 (18)0.0261 (8)
C150.4761 (3)0.64757 (15)0.14044 (17)0.0243 (7)
C160.3820 (3)0.64371 (16)0.10646 (17)0.0257 (8)
C170.2825 (3)0.68634 (16)0.11813 (18)0.0267 (8)
C180.2864 (3)0.70968 (15)0.18978 (19)0.0275 (8)
C190.1856 (3)0.69632 (15)0.22081 (18)0.0258 (8)
C200.1806 (3)0.68786 (16)0.28802 (19)0.0281 (8)
C210.0902 (3)0.64666 (17)0.32089 (19)0.0296 (8)
C220.1577 (3)0.61088 (17)0.37402 (18)0.0288 (8)
C230.1516 (3)0.54476 (17)0.38277 (18)0.0286 (8)
C240.2478 (3)0.50418 (17)0.40167 (18)0.0299 (8)
C250.3489 (3)0.53305 (17)0.40760 (18)0.0296 (8)
C260.4460 (3)0.49969 (18)0.38851 (19)0.0305 (8)
C270.4398 (3)0.43805 (16)0.35908 (18)0.0291 (8)
C280.5176 (3)0.41480 (17)0.30469 (19)0.0287 (8)
C290.5666 (3)0.47649 (17)0.27315 (19)0.0272 (8)
C300.5707 (3)0.48579 (16)0.20122 (18)0.0250 (8)
C310.5270 (3)0.43556 (16)0.15223 (19)0.0287 (8)
C320.4551 (3)0.47340 (17)0.10231 (18)0.0268 (8)
C330.4661 (3)0.54056 (17)0.08970 (17)0.0263 (8)
C340.3720 (3)0.57849 (16)0.07406 (17)0.0258 (8)
C350.2707 (3)0.54783 (16)0.06645 (17)0.0267 (8)
C360.1713 (3)0.58109 (17)0.08977 (18)0.0274 (8)
C370.1775 (3)0.64362 (16)0.11863 (18)0.0272 (8)
C380.1177 (3)0.65612 (16)0.17592 (18)0.0268 (8)
C390.0511 (3)0.60700 (17)0.20200 (19)0.0277 (8)
C400.0458 (3)0.59568 (17)0.27249 (19)0.0284 (8)
C410.0289 (3)0.53056 (17)0.2855 (2)0.0303 (8)
C420.0679 (3)0.49851 (17)0.34864 (19)0.0300 (8)
C430.1407 (3)0.43805 (16)0.3320 (2)0.0300 (8)
C440.2397 (3)0.44086 (16)0.37059 (19)0.0295 (8)
C450.3354 (3)0.40920 (16)0.34837 (19)0.0289 (8)
C460.3330 (3)0.37552 (16)0.28586 (19)0.0290 (8)
C470.4370 (3)0.38438 (15)0.25475 (19)0.0280 (8)
C480.4406 (3)0.39327 (15)0.18807 (19)0.0265 (8)
C490.3412 (3)0.39306 (16)0.15049 (19)0.0291 (8)
C500.3505 (3)0.44281 (16)0.09845 (19)0.0283 (8)
C510.2605 (3)0.47880 (17)0.07770 (18)0.0285 (8)
C520.1432 (3)0.46134 (17)0.09818 (19)0.0295 (8)
C530.0984 (3)0.53129 (17)0.11393 (18)0.0280 (8)
C540.0390 (3)0.54503 (17)0.17000 (19)0.0295 (8)
C550.0065 (3)0.49235 (17)0.2208 (2)0.0316 (9)
C560.0844 (3)0.43415 (16)0.2148 (2)0.0292 (8)
C570.1400 (3)0.40745 (16)0.2726 (2)0.0298 (8)
C580.2379 (3)0.37374 (15)0.2490 (2)0.0284 (8)
C590.2419 (3)0.38264 (15)0.18070 (19)0.0287 (8)
C600.1450 (3)0.42110 (16)0.1605 (2)0.0293 (8)
C610.6113 (3)0.39149 (17)0.1164 (2)0.0319 (9)
C620.6463 (3)0.60561 (17)0.08318 (19)0.0304 (8)
C630.5671 (3)0.75369 (17)0.1838 (2)0.0321 (9)
C640.2726 (3)0.74343 (17)0.0683 (2)0.0332 (9)
C650.5998 (3)0.36236 (18)0.3293 (2)0.0343 (9)
C660.6245 (3)0.5595 (2)0.4209 (2)0.0370 (9)
C670.5543 (3)0.73045 (18)0.3590 (2)0.0359 (9)
C680.2572 (3)0.69083 (19)0.4531 (2)0.0383 (10)
C690.0057 (3)0.69122 (18)0.3437 (2)0.0368 (9)
C700.0227 (3)0.47745 (19)0.3963 (2)0.0373 (9)
C710.1144 (3)0.47384 (19)0.2125 (2)0.0384 (10)
C720.0861 (3)0.42380 (18)0.0419 (2)0.0370 (9)
F6110.66741 (18)0.35333 (10)0.15730 (12)0.0434 (6)
F6120.68207 (17)0.42821 (10)0.08279 (11)0.0373 (5)
F6130.56072 (18)0.35232 (10)0.07283 (12)0.0410 (6)
F6210.70069 (18)0.55188 (10)0.06297 (12)0.0403 (6)
F6220.71669 (18)0.64290 (11)0.11774 (12)0.0442 (6)
F6230.61639 (17)0.63995 (10)0.03062 (11)0.0384 (5)
F6310.5620 (2)0.77039 (14)0.12184 (13)0.0643 (8)
F6320.67022 (18)0.74309 (11)0.19896 (14)0.0543 (7)
F6330.5364 (2)0.80616 (11)0.21872 (15)0.0622 (8)
F6410.2722 (2)0.71984 (11)0.00726 (11)0.0434 (6)
F6420.35450 (18)0.78687 (10)0.07388 (12)0.0454 (6)
F6430.17957 (18)0.77742 (10)0.07661 (11)0.0380 (5)
F6510.66163 (19)0.33893 (11)0.28142 (12)0.0473 (6)
F6520.54784 (19)0.31059 (11)0.35540 (14)0.0556 (7)
F6530.6656 (2)0.38666 (12)0.37444 (13)0.0544 (7)
F6610.58658 (19)0.58067 (12)0.47871 (11)0.0444 (6)
F6620.69862 (18)0.60371 (12)0.40074 (12)0.0466 (6)
F6630.67566 (18)0.50196 (11)0.43147 (12)0.0450 (6)
F6910.0706 (2)0.66045 (12)0.38405 (16)0.0645 (8)
F6920.0640 (3)0.71067 (16)0.29227 (15)0.0817 (10)
F6930.0276 (2)0.74630 (12)0.37154 (17)0.0721 (9)
F7010.0194 (2)0.45074 (11)0.45045 (12)0.0495 (6)
F7020.0892 (2)0.43242 (12)0.36954 (14)0.0561 (7)
F7030.08363 (18)0.52964 (11)0.41401 (12)0.0437 (6)
F7110.14409 (19)0.42251 (12)0.24751 (15)0.0563 (7)
F7120.1373 (2)0.45961 (14)0.15034 (14)0.0615 (8)
F7130.17832 (17)0.52528 (11)0.22916 (14)0.0541 (7)
F7210.01828 (17)0.40987 (11)0.05478 (12)0.0436 (6)
F7220.08801 (18)0.45966 (11)0.01372 (11)0.0404 (6)
F7230.13747 (19)0.36623 (11)0.03010 (13)0.0477 (6)
F6710.6544 (3)0.7341 (2)0.3353 (2)0.0493 (10)0.85
F6720.5621 (3)0.71815 (17)0.42302 (16)0.0482 (8)0.85
F6730.5079 (3)0.79036 (15)0.35302 (19)0.0495 (9)0.85
F6830.1721 (7)0.7319 (5)0.4531 (3)0.053 (3)0.73 (3)
F6820.2451 (8)0.6501 (3)0.5031 (3)0.0484 (18)0.73 (3)
F6810.3460 (6)0.7265 (3)0.4605 (4)0.052 (2)0.73 (3)
F6740.6599 (14)0.7149 (12)0.3663 (12)0.053 (7)0.15
F6750.5137 (17)0.7459 (8)0.4186 (8)0.052 (6)0.15
F6760.5494 (15)0.7873 (8)0.3230 (8)0.038 (5)0.15
F6850.229 (4)0.7544 (8)0.4420 (7)0.071 (8)0.27 (3)
F6840.187 (3)0.6685 (15)0.4960 (12)0.087 (11)0.27 (3)
F6860.3519 (15)0.697 (2)0.4868 (17)0.098 (13)0.27 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0258 (19)0.0214 (17)0.037 (2)0.0020 (14)0.0058 (16)0.0025 (15)
C20.0190 (17)0.0234 (17)0.036 (2)0.0072 (14)0.0026 (15)0.0017 (15)
C30.0206 (18)0.0193 (16)0.041 (2)0.0019 (14)0.0005 (16)0.0006 (15)
C40.0258 (19)0.0122 (15)0.041 (2)0.0026 (13)0.0005 (16)0.0027 (14)
C50.0254 (19)0.0169 (16)0.037 (2)0.0008 (14)0.0038 (16)0.0061 (14)
C60.028 (2)0.0185 (16)0.040 (2)0.0029 (14)0.0015 (17)0.0076 (15)
C70.029 (2)0.0241 (18)0.040 (2)0.0020 (15)0.0007 (17)0.0018 (16)
C80.030 (2)0.0291 (18)0.029 (2)0.0012 (15)0.0023 (16)0.0019 (15)
C90.028 (2)0.0295 (19)0.034 (2)0.0001 (15)0.0045 (17)0.0017 (16)
C100.0224 (19)0.0288 (18)0.038 (2)0.0013 (15)0.0034 (16)0.0037 (16)
C110.0141 (17)0.0282 (18)0.039 (2)0.0015 (14)0.0035 (15)0.0041 (16)
C120.0144 (16)0.0233 (17)0.039 (2)0.0023 (13)0.0025 (15)0.0029 (15)
C130.0143 (16)0.0242 (17)0.038 (2)0.0012 (13)0.0008 (15)0.0008 (15)
C140.0204 (18)0.0190 (16)0.039 (2)0.0008 (14)0.0011 (16)0.0006 (15)
C150.0222 (18)0.0178 (16)0.033 (2)0.0009 (13)0.0020 (15)0.0026 (14)
C160.0245 (19)0.0201 (16)0.032 (2)0.0001 (14)0.0006 (16)0.0026 (14)
C170.0251 (19)0.0190 (16)0.036 (2)0.0007 (14)0.0017 (16)0.0016 (14)
C180.0267 (19)0.0114 (15)0.044 (2)0.0018 (13)0.0010 (17)0.0023 (14)
C190.0234 (18)0.0120 (15)0.042 (2)0.0041 (13)0.0020 (16)0.0007 (14)
C200.0255 (19)0.0179 (16)0.041 (2)0.0040 (14)0.0005 (17)0.0027 (15)
C210.0217 (18)0.0215 (17)0.046 (2)0.0045 (14)0.0030 (17)0.0014 (16)
C220.0234 (19)0.0249 (17)0.038 (2)0.0026 (15)0.0047 (16)0.0039 (15)
C230.0243 (19)0.0265 (18)0.035 (2)0.0022 (15)0.0077 (16)0.0009 (15)
C240.029 (2)0.0268 (18)0.034 (2)0.0008 (15)0.0035 (16)0.0068 (15)
C250.029 (2)0.0273 (18)0.032 (2)0.0038 (15)0.0023 (16)0.0035 (15)
C260.0256 (19)0.0311 (19)0.035 (2)0.0030 (15)0.0038 (16)0.0105 (16)
C270.028 (2)0.0218 (17)0.038 (2)0.0042 (15)0.0001 (17)0.0108 (15)
C280.0211 (18)0.0233 (17)0.042 (2)0.0041 (14)0.0001 (16)0.0080 (15)
C290.0147 (17)0.0248 (17)0.042 (2)0.0032 (14)0.0013 (16)0.0052 (15)
C300.0114 (16)0.0209 (16)0.043 (2)0.0005 (13)0.0009 (15)0.0039 (15)
C310.0212 (18)0.0206 (16)0.044 (2)0.0035 (14)0.0038 (17)0.0020 (15)
C320.0192 (18)0.0249 (17)0.036 (2)0.0020 (14)0.0013 (16)0.0038 (15)
C330.0219 (18)0.0263 (18)0.031 (2)0.0013 (14)0.0042 (15)0.0010 (15)
C340.0272 (19)0.0203 (16)0.030 (2)0.0016 (14)0.0014 (16)0.0004 (14)
C350.0274 (19)0.0246 (17)0.028 (2)0.0001 (15)0.0044 (16)0.0042 (15)
C360.0221 (18)0.0252 (17)0.035 (2)0.0013 (14)0.0087 (16)0.0003 (15)
C370.0217 (18)0.0188 (16)0.041 (2)0.0040 (14)0.0099 (16)0.0043 (15)
C380.0209 (18)0.0205 (16)0.039 (2)0.0082 (14)0.0050 (16)0.0006 (15)
C390.0154 (17)0.0245 (17)0.043 (2)0.0036 (14)0.0036 (16)0.0015 (16)
C400.0153 (17)0.0251 (18)0.045 (2)0.0028 (14)0.0011 (16)0.0017 (16)
C410.0122 (17)0.0249 (18)0.054 (2)0.0007 (14)0.0053 (16)0.0013 (16)
C420.0216 (19)0.0227 (17)0.046 (2)0.0035 (14)0.0046 (17)0.0001 (16)
C430.0229 (19)0.0197 (16)0.047 (2)0.0028 (14)0.0055 (17)0.0084 (16)
C440.0269 (19)0.0203 (17)0.041 (2)0.0024 (15)0.0057 (17)0.0091 (15)
C450.0225 (19)0.0201 (16)0.044 (2)0.0032 (14)0.0042 (17)0.0116 (16)
C460.0251 (19)0.0140 (15)0.048 (2)0.0012 (14)0.0061 (17)0.0075 (15)
C470.0221 (18)0.0126 (15)0.049 (2)0.0041 (13)0.0039 (17)0.0043 (15)
C480.0209 (18)0.0144 (15)0.044 (2)0.0031 (13)0.0050 (16)0.0012 (15)
C490.030 (2)0.0123 (15)0.045 (2)0.0028 (14)0.0000 (17)0.0057 (15)
C500.0262 (19)0.0205 (16)0.038 (2)0.0005 (14)0.0016 (16)0.0096 (15)
C510.028 (2)0.0245 (17)0.033 (2)0.0007 (15)0.0023 (16)0.0049 (15)
C520.0221 (18)0.0239 (17)0.043 (2)0.0032 (14)0.0028 (16)0.0049 (16)
C530.0207 (18)0.0229 (17)0.040 (2)0.0018 (14)0.0100 (17)0.0016 (15)
C540.0155 (17)0.0265 (18)0.046 (2)0.0022 (14)0.0073 (17)0.0005 (16)
C550.0210 (19)0.0239 (17)0.050 (2)0.0014 (15)0.0040 (17)0.0033 (16)
C560.0207 (18)0.0176 (16)0.049 (2)0.0057 (14)0.0013 (17)0.0015 (15)
C570.0226 (19)0.0173 (16)0.049 (2)0.0031 (14)0.0066 (17)0.0028 (16)
C580.0220 (18)0.0126 (15)0.051 (2)0.0026 (13)0.0027 (17)0.0032 (15)
C590.0242 (19)0.0125 (15)0.049 (2)0.0029 (14)0.0005 (17)0.0038 (15)
C600.0224 (18)0.0172 (16)0.048 (2)0.0056 (14)0.0052 (17)0.0070 (16)
C610.0238 (19)0.0213 (17)0.051 (2)0.0021 (15)0.0038 (18)0.0029 (17)
C620.0258 (19)0.0238 (17)0.042 (2)0.0010 (15)0.0019 (17)0.0010 (16)
C630.029 (2)0.0204 (17)0.047 (3)0.0020 (15)0.0047 (18)0.0001 (16)
C640.032 (2)0.0247 (18)0.043 (2)0.0020 (16)0.0024 (18)0.0010 (16)
C650.026 (2)0.0307 (19)0.046 (2)0.0053 (16)0.0017 (19)0.0082 (18)
C660.033 (2)0.038 (2)0.040 (2)0.0013 (18)0.0011 (19)0.0016 (18)
C670.036 (2)0.0260 (19)0.046 (3)0.0007 (17)0.005 (2)0.0014 (18)
C680.031 (2)0.037 (2)0.047 (3)0.0044 (18)0.002 (2)0.0036 (19)
C690.031 (2)0.0223 (18)0.057 (3)0.0032 (16)0.005 (2)0.0009 (18)
C700.027 (2)0.030 (2)0.055 (3)0.0034 (17)0.0069 (19)0.0010 (19)
C710.025 (2)0.028 (2)0.062 (3)0.0004 (16)0.002 (2)0.0018 (19)
C720.030 (2)0.0283 (19)0.053 (3)0.0001 (16)0.0042 (19)0.0043 (18)
F6110.0351 (13)0.0351 (12)0.0601 (15)0.0167 (10)0.0077 (11)0.0090 (11)
F6120.0268 (11)0.0299 (11)0.0552 (15)0.0001 (9)0.0107 (10)0.0003 (10)
F6130.0332 (12)0.0303 (11)0.0596 (15)0.0014 (10)0.0070 (11)0.0124 (11)
F6210.0335 (12)0.0294 (11)0.0582 (15)0.0038 (9)0.0150 (11)0.0024 (10)
F6220.0295 (12)0.0463 (13)0.0568 (15)0.0131 (10)0.0028 (11)0.0060 (11)
F6230.0353 (12)0.0332 (11)0.0469 (14)0.0025 (10)0.0066 (10)0.0107 (10)
F6310.081 (2)0.0622 (17)0.0494 (16)0.0450 (15)0.0112 (14)0.0190 (13)
F6320.0266 (13)0.0378 (13)0.099 (2)0.0113 (10)0.0084 (13)0.0184 (13)
F6330.0525 (16)0.0208 (11)0.113 (2)0.0118 (11)0.0281 (16)0.0185 (13)
F6410.0544 (15)0.0365 (12)0.0393 (13)0.0126 (11)0.0003 (11)0.0032 (10)
F6420.0408 (14)0.0290 (11)0.0665 (17)0.0070 (10)0.0039 (12)0.0125 (11)
F6430.0389 (13)0.0260 (11)0.0491 (14)0.0120 (9)0.0011 (11)0.0040 (10)
F6510.0361 (13)0.0443 (13)0.0614 (16)0.0199 (11)0.0063 (12)0.0104 (12)
F6520.0367 (14)0.0359 (13)0.094 (2)0.0083 (11)0.0104 (13)0.0347 (13)
F6530.0512 (15)0.0426 (14)0.0690 (17)0.0148 (12)0.0237 (14)0.0061 (12)
F6610.0415 (14)0.0528 (14)0.0388 (14)0.0036 (11)0.0072 (11)0.0017 (11)
F6620.0346 (13)0.0507 (14)0.0544 (15)0.0133 (11)0.0103 (11)0.0043 (12)
F6630.0346 (13)0.0448 (13)0.0555 (15)0.0086 (10)0.0135 (11)0.0074 (11)
F6910.0446 (15)0.0362 (13)0.113 (2)0.0098 (11)0.0424 (16)0.0128 (14)
F6920.074 (2)0.098 (2)0.073 (2)0.0656 (19)0.0051 (17)0.0033 (17)
F6930.0493 (16)0.0376 (14)0.129 (3)0.0004 (12)0.0221 (17)0.0352 (16)
F7010.0457 (15)0.0439 (14)0.0593 (16)0.0109 (11)0.0173 (13)0.0149 (12)
F7020.0404 (14)0.0476 (14)0.0804 (19)0.0206 (12)0.0209 (13)0.0129 (13)
F7030.0318 (12)0.0373 (12)0.0620 (16)0.0084 (10)0.0157 (11)0.0038 (11)
F7110.0288 (13)0.0411 (13)0.099 (2)0.0082 (11)0.0040 (13)0.0223 (14)
F7120.0333 (14)0.0794 (19)0.0718 (19)0.0195 (13)0.0062 (13)0.0171 (15)
F7130.0206 (12)0.0375 (13)0.104 (2)0.0058 (10)0.0067 (13)0.0081 (13)
F7210.0272 (12)0.0411 (13)0.0625 (16)0.0110 (10)0.0054 (11)0.0079 (11)
F7220.0313 (12)0.0418 (13)0.0480 (14)0.0013 (10)0.0068 (10)0.0073 (11)
F7230.0420 (14)0.0300 (12)0.0708 (17)0.0022 (10)0.0099 (12)0.0172 (11)
F6710.0317 (18)0.049 (3)0.067 (3)0.0191 (16)0.0003 (18)0.017 (2)
F6720.059 (2)0.044 (2)0.0416 (19)0.0163 (17)0.0143 (17)0.0033 (16)
F6730.053 (2)0.0257 (15)0.070 (3)0.0019 (16)0.0240 (19)0.0106 (17)
F6830.060 (4)0.049 (4)0.048 (3)0.024 (3)0.003 (3)0.013 (3)
F6820.065 (4)0.045 (2)0.035 (2)0.002 (2)0.000 (2)0.0006 (17)
F6810.053 (3)0.046 (3)0.058 (4)0.014 (2)0.003 (2)0.018 (2)
F6740.044 (12)0.044 (13)0.072 (18)0.008 (9)0.008 (12)0.003 (11)
F6750.084 (16)0.024 (9)0.047 (12)0.011 (9)0.008 (11)0.014 (8)
F6760.036 (11)0.025 (8)0.052 (13)0.006 (7)0.017 (8)0.008 (8)
F6850.12 (2)0.039 (7)0.057 (8)0.012 (10)0.021 (9)0.003 (5)
F6840.12 (2)0.075 (15)0.065 (11)0.039 (16)0.039 (14)0.023 (10)
F6860.059 (9)0.15 (3)0.087 (18)0.033 (13)0.028 (10)0.082 (18)
Geometric parameters (Å, º) top
C1—C91.520 (5)C39—C401.456 (5)
C1—C21.532 (5)C40—C411.347 (5)
C1—C51.543 (5)C41—C421.513 (5)
C1—C671.567 (5)C41—C551.548 (5)
C2—C121.359 (5)C42—C701.538 (5)
C2—C31.542 (5)C42—C431.543 (5)
C3—C151.518 (5)C43—C571.358 (5)
C3—C41.542 (5)C43—C441.442 (5)
C3—C631.553 (5)C44—C451.409 (5)
C4—C181.387 (5)C45—C461.442 (5)
C4—C51.404 (5)C46—C581.383 (5)
C5—C61.385 (5)C46—C471.436 (5)
C6—C201.402 (5)C47—C481.371 (5)
C6—C71.533 (5)C48—C491.435 (5)
C7—C81.511 (5)C49—C591.381 (5)
C7—C681.543 (5)C49—C501.460 (5)
C7—C221.546 (5)C50—C511.381 (5)
C8—C91.352 (5)C51—C521.538 (5)
C8—C251.463 (5)C52—C601.504 (5)
C9—C101.543 (5)C52—C721.538 (5)
C10—C111.493 (5)C52—C531.540 (5)
C10—C661.537 (5)C53—C541.385 (5)
C10—C261.545 (5)C54—C551.532 (5)
C11—C291.358 (5)C55—C561.511 (5)
C11—C121.462 (5)C55—C711.535 (5)
C12—C131.463 (5)C56—C601.361 (5)
C13—C301.365 (5)C56—C571.459 (5)
C13—C141.499 (5)C57—C581.460 (5)
C14—C331.536 (5)C58—C591.404 (5)
C14—C621.537 (5)C59—C601.472 (5)
C14—C151.545 (5)C61—F6111.322 (4)
C15—C161.343 (5)C61—F6121.329 (4)
C16—C341.469 (5)C61—F6131.335 (4)
C16—C171.508 (5)C62—F6231.323 (4)
C17—C641.533 (5)C62—F6211.332 (4)
C17—C181.534 (5)C62—F6221.338 (4)
C17—C371.545 (5)C63—F6311.308 (5)
C18—C191.416 (5)C63—F6321.315 (4)
C19—C201.382 (5)C63—F6331.325 (4)
C19—C381.473 (5)C64—F6411.331 (4)
C20—C211.537 (5)C64—F6421.332 (4)
C21—C401.518 (5)C64—F6431.339 (4)
C21—C221.536 (5)C65—F6531.312 (4)
C21—C691.548 (5)C65—F6511.324 (5)
C22—C231.339 (5)C65—F6521.329 (4)
C23—C241.481 (5)C66—F6631.328 (4)
C23—C421.545 (5)C66—F6621.335 (4)
C24—C251.371 (5)C66—F6611.338 (5)
C24—C441.421 (5)C67—F6711.323 (5)
C25—C261.421 (5)C67—F6721.331 (5)
C26—C271.375 (5)C67—F6731.333 (5)
C27—C451.419 (5)C67—F6741.337 (16)
C27—C281.538 (5)C67—F6751.350 (14)
C28—C291.518 (5)C67—F6761.356 (14)
C28—C651.538 (5)C68—F6841.305 (14)
C28—C471.541 (5)C68—F6811.309 (7)
C29—C301.479 (5)C68—F6821.316 (6)
C30—C311.513 (5)C68—F6831.327 (5)
C31—C321.541 (5)C68—F6851.336 (11)
C31—C481.543 (5)C68—F6861.352 (13)
C31—C611.545 (5)C69—F6911.301 (5)
C32—C331.376 (5)C69—F6931.305 (4)
C32—C501.422 (5)C69—F6921.324 (5)
C33—C341.415 (5)C70—F7011.328 (5)
C34—C351.392 (5)C70—F7021.331 (5)
C35—C511.407 (5)C70—F7031.335 (4)
C35—C361.469 (5)C71—F7111.304 (5)
C36—C371.386 (5)C71—F7121.327 (5)
C36—C531.428 (5)C71—F7131.339 (4)
C37—C381.404 (5)C72—F7211.336 (4)
C38—C391.386 (5)C72—F7231.336 (4)
C39—C541.410 (5)C72—F7221.342 (5)
C9—C1—C2110.7 (3)C45—C44—C24119.2 (3)
C9—C1—C5107.7 (3)C45—C44—C43120.4 (3)
C2—C1—C598.6 (3)C24—C44—C43109.5 (3)
C9—C1—C67112.0 (3)C44—C45—C27121.2 (3)
C2—C1—C67113.7 (3)C44—C45—C46118.8 (3)
C5—C1—C67113.4 (3)C27—C45—C46109.9 (3)
C12—C2—C1121.5 (3)C58—C46—C47120.6 (4)
C12—C2—C3121.7 (3)C58—C46—C45120.3 (3)
C1—C2—C3111.6 (3)C47—C46—C45108.6 (3)
C15—C3—C4107.8 (3)C48—C47—C46119.1 (3)
C15—C3—C2110.6 (3)C48—C47—C28125.4 (3)
C4—C3—C297.9 (3)C46—C47—C28108.9 (3)
C15—C3—C63112.7 (3)C47—C48—C49119.8 (3)
C4—C3—C63113.9 (3)C47—C48—C31124.5 (3)
C2—C3—C63112.9 (3)C49—C48—C31109.3 (3)
C18—C4—C5120.1 (3)C59—C49—C48120.6 (3)
C18—C4—C3122.9 (3)C59—C49—C50119.9 (3)
C5—C4—C3112.2 (3)C48—C49—C50108.4 (3)
C6—C5—C4120.5 (3)C51—C50—C32120.6 (3)
C6—C5—C1123.3 (3)C51—C50—C49120.9 (3)
C4—C5—C1111.1 (3)C32—C50—C49109.1 (3)
C5—C6—C20119.9 (3)C50—C51—C35119.4 (3)
C5—C6—C7123.6 (3)C50—C51—C52122.9 (3)
C20—C6—C7110.7 (3)C35—C51—C52110.6 (3)
C8—C7—C6106.9 (3)C60—C52—C72111.9 (3)
C8—C7—C68108.2 (3)C60—C52—C51110.0 (3)
C6—C7—C68115.9 (3)C72—C52—C51109.3 (3)
C8—C7—C22111.9 (3)C60—C52—C53108.4 (3)
C6—C7—C22100.9 (3)C72—C52—C53116.0 (3)
C68—C7—C22112.9 (3)C51—C52—C53100.6 (3)
C9—C8—C25110.5 (3)C54—C53—C36118.5 (3)
C9—C8—C7125.4 (3)C54—C53—C52122.8 (3)
C25—C8—C7121.1 (3)C36—C53—C52109.8 (3)
C8—C9—C1124.0 (3)C53—C54—C39120.1 (3)
C8—C9—C10110.1 (3)C53—C54—C55124.0 (3)
C1—C9—C10123.2 (3)C39—C54—C55108.7 (3)
C11—C10—C66113.5 (3)C56—C55—C54108.1 (3)
C11—C10—C9109.0 (3)C56—C55—C71114.4 (3)
C66—C10—C9111.5 (3)C54—C55—C71110.2 (3)
C11—C10—C26107.5 (3)C56—C55—C41109.9 (3)
C66—C10—C26113.4 (3)C54—C55—C41100.9 (3)
C9—C10—C26101.2 (3)C71—C55—C41112.3 (3)
C29—C11—C12108.2 (3)C60—C56—C57109.4 (3)
C29—C11—C10125.8 (3)C60—C56—C55124.1 (3)
C12—C11—C10121.4 (3)C57—C56—C55120.7 (3)
C2—C12—C11124.5 (3)C43—C57—C56123.7 (3)
C2—C12—C13124.1 (3)C43—C57—C58120.1 (3)
C11—C12—C13106.3 (3)C56—C57—C58106.5 (3)
C30—C13—C12108.4 (3)C46—C58—C59120.1 (3)
C30—C13—C14125.6 (3)C46—C58—C57120.0 (3)
C12—C13—C14121.6 (3)C59—C58—C57107.5 (3)
C13—C14—C33107.5 (3)C49—C59—C58119.7 (3)
C13—C14—C62114.1 (3)C49—C59—C60120.4 (3)
C33—C14—C62113.4 (3)C58—C59—C60108.2 (3)
C13—C14—C15108.9 (3)C56—C60—C59108.4 (3)
C33—C14—C15101.3 (3)C56—C60—C52125.3 (3)
C62—C14—C15110.9 (3)C59—C60—C52121.7 (3)
C16—C15—C3124.3 (3)F611—C61—F612107.9 (3)
C16—C15—C14109.9 (3)F611—C61—F613108.5 (3)
C3—C15—C14123.2 (3)F612—C61—F613106.6 (3)
C15—C16—C34110.6 (3)F611—C61—C31112.2 (3)
C15—C16—C17125.3 (3)F612—C61—C31111.5 (3)
C34—C16—C17120.6 (3)F613—C61—C31109.9 (3)
C16—C17—C64112.3 (3)F623—C62—F621107.9 (3)
C16—C17—C18107.5 (3)F623—C62—F622108.1 (3)
C64—C17—C18113.9 (3)F621—C62—F622107.0 (3)
C16—C17—C37111.2 (3)F623—C62—C14111.8 (3)
C64—C17—C37110.8 (3)F621—C62—C14111.2 (3)
C18—C17—C37100.6 (3)F622—C62—C14110.6 (3)
C4—C18—C19119.1 (3)F631—C63—F632108.0 (3)
C4—C18—C17123.5 (3)F631—C63—F633107.6 (3)
C19—C18—C17110.1 (3)F632—C63—F633106.1 (3)
C20—C19—C18120.6 (3)F631—C63—C3112.1 (3)
C20—C19—C38121.4 (3)F632—C63—C3112.2 (3)
C18—C19—C38108.5 (3)F633—C63—C3110.5 (3)
C19—C20—C6119.9 (3)F641—C64—F642108.1 (3)
C19—C20—C21122.2 (3)F641—C64—F643107.4 (3)
C6—C20—C21112.6 (3)F642—C64—F643107.3 (3)
C40—C21—C22109.5 (3)F641—C64—C17110.7 (3)
C40—C21—C20109.5 (3)F642—C64—C17112.0 (3)
C22—C21—C2099.9 (3)F643—C64—C17111.1 (3)
C40—C21—C69108.3 (3)F653—C65—F651107.3 (3)
C22—C21—C69117.6 (3)F653—C65—F652107.6 (3)
C20—C21—C69111.7 (3)F651—C65—F652107.1 (3)
C23—C22—C21121.7 (3)F653—C65—C28112.0 (3)
C23—C22—C7121.4 (3)F651—C65—C28112.1 (3)
C21—C22—C7110.7 (3)F652—C65—C28110.4 (3)
C22—C23—C24122.2 (3)F663—C66—F662107.7 (3)
C22—C23—C42124.8 (3)F663—C66—F661107.3 (3)
C24—C23—C42108.3 (3)F662—C66—F661107.4 (3)
C25—C24—C44118.5 (3)F663—C66—C10112.4 (3)
C25—C24—C23120.5 (3)F662—C66—C10110.5 (3)
C44—C24—C23108.7 (3)F661—C66—C10111.2 (3)
C24—C25—C26122.3 (3)F671—C67—F672107.9 (4)
C24—C25—C8119.5 (3)F671—C67—F673108.2 (4)
C26—C25—C8108.4 (3)F672—C67—F673106.6 (4)
C27—C26—C25119.8 (3)F671—C67—F67432.4 (9)
C27—C26—C10123.4 (3)F672—C67—F67477.5 (10)
C25—C26—C10108.3 (3)F673—C67—F674129.1 (11)
C26—C27—C45118.8 (3)F671—C67—F675131.5 (10)
C26—C27—C28123.6 (3)F672—C67—F67535.5 (8)
C45—C27—C28109.1 (3)F673—C67—F67573.5 (8)
C29—C28—C65115.8 (3)F674—C67—F675108.3 (13)
C29—C28—C27107.8 (3)F671—C67—F67678.1 (8)
C65—C28—C27112.3 (3)F672—C67—F676133.6 (8)
C29—C28—C47107.2 (3)F673—C67—F67634.6 (6)
C65—C28—C47111.2 (3)F674—C67—F676107.1 (12)
C27—C28—C47101.4 (3)F675—C67—F676106.2 (10)
C11—C29—C30108.9 (3)F671—C67—C1111.4 (3)
C11—C29—C28123.9 (3)F672—C67—C1111.4 (3)
C30—C29—C28122.5 (3)F673—C67—C1111.3 (3)
C13—C30—C29108.0 (3)F674—C67—C1113.9 (12)
C13—C30—C31123.6 (3)F675—C67—C1112.5 (9)
C29—C30—C31123.8 (3)F676—C67—C1108.4 (9)
C30—C31—C32107.9 (3)F684—C68—F681131.0 (12)
C30—C31—C48107.1 (3)F684—C68—F68236.0 (19)
C32—C31—C48101.1 (3)F681—C68—F682110.2 (4)
C30—C31—C61117.2 (3)F684—C68—F68372.3 (18)
C32—C31—C61110.5 (3)F681—C68—F683108.3 (5)
C48—C31—C61111.8 (3)F682—C68—F683107.0 (4)
C33—C32—C50120.0 (3)F684—C68—F685105.9 (10)
C33—C32—C31123.2 (3)F681—C68—F68573.2 (17)
C50—C32—C31109.6 (3)F682—C68—F685133.8 (9)
C32—C33—C34119.1 (3)F683—C68—F68537.9 (14)
C32—C33—C14123.7 (3)F684—C68—F686104.8 (11)
C34—C33—C14108.5 (3)F681—C68—F68635 (2)
C35—C34—C33120.8 (3)F682—C68—F68676 (2)
C35—C34—C16121.0 (3)F683—C68—F686127.7 (10)
C33—C34—C16108.1 (3)F685—C68—F686102.2 (11)
C34—C35—C51119.7 (3)F684—C68—C7114.9 (8)
C34—C35—C36120.2 (3)F681—C68—C7109.9 (4)
C51—C35—C36108.6 (3)F682—C68—C7109.4 (4)
C37—C36—C53121.2 (3)F683—C68—C7112.0 (4)
C37—C36—C35120.3 (3)F685—C68—C7112.2 (7)
C53—C36—C35108.4 (3)F686—C68—C7115.6 (8)
C36—C37—C38119.1 (3)F691—C69—F693108.5 (4)
C36—C37—C17122.8 (3)F691—C69—F692108.1 (4)
C38—C37—C17110.2 (3)F693—C69—F692105.2 (3)
C39—C38—C37120.2 (3)F691—C69—C21112.5 (3)
C39—C38—C19118.8 (3)F693—C69—C21112.5 (3)
C37—C38—C19108.6 (3)F692—C69—C21109.8 (3)
C38—C39—C54120.6 (3)F701—C70—F702107.6 (3)
C38—C39—C40121.2 (3)F701—C70—F703107.9 (3)
C54—C39—C40108.3 (3)F702—C70—F703107.5 (3)
C41—C40—C39110.6 (3)F701—C70—C42110.9 (3)
C41—C40—C21125.3 (4)F702—C70—C42111.6 (3)
C39—C40—C21121.2 (3)F703—C70—C42111.2 (3)
C40—C41—C42122.0 (3)F711—C71—F712107.1 (3)
C40—C41—C55109.8 (3)F711—C71—F713107.6 (3)
C42—C41—C55124.6 (3)F712—C71—F713106.6 (3)
C41—C42—C70115.4 (3)F711—C71—C55113.7 (3)
C41—C42—C43109.1 (3)F712—C71—C55110.8 (3)
C70—C42—C43110.1 (3)F713—C71—C55110.6 (3)
C41—C42—C23109.5 (3)F721—C72—F723107.9 (3)
C70—C42—C23111.1 (3)F721—C72—F722107.4 (3)
C43—C42—C23100.7 (3)F723—C72—F722107.5 (3)
C57—C43—C44120.3 (3)F721—C72—C52112.8 (3)
C57—C43—C42123.3 (3)F723—C72—C52110.1 (3)
C44—C43—C42109.6 (3)F722—C72—C52111.0 (3)

Experimental details

Crystal data
Chemical formulaC72F36
Mr1548.72
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)12.2475 (2), 20.0326 (4), 20.3782 (4)
β (°) 90.288 (1)
V3)4999.71 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.13 × 0.10 × 0.08
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.973, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
123040, 10625, 6628
Rint0.079
(sin θ/λ)max1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.160, 1.03
No. of reflections10625
No. of parameters1030
No. of restraints24
Δρmax, Δρmin (e Å3)0.47, 0.32

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

 

Acknowledgements

The authors thank the US National Science Foundation (grant CHE-0707223) for supporting this study.

References

First citationBruker (2000). APEX2 (Version 2.10) and SHELXTL (Version 6.14). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKareev, I. E., Kuvychko, I. V., Lebedkin, S. F., Miller, S. M., Anderson, O. P., Seppelt, K., Strauss, S. H. & Boltalina, O. V. (2005). J. Am. Chem. Soc. 127, 8362–8375.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationKareev, I. E., Shustova, N. B., Peyshkov, D. V., Lebedkin, S. F., Miller, S. M., Anderson, O. P., Popov, A. A., Boltalina, O. V. & Strauss, S. H. (2007). Chem. Commun. pp. 1650–1652.  Web of Science CSD CrossRef Google Scholar
First citationOmelyanyuk, N. A., Goryunkov, A. A., Tamm, N. B., Avdoshenko, S. M., Ioffe, I. N., Sidorov, L. N., Kemnitz, E. & Troyanov, S. I. (2007). Chem. Commun. pp.4794–4796.  CrossRef Google Scholar
First citationPopov, A. A., Kareev, I. E., Shustova, N. B., Stukalin, E. B., Lebedkin, S. F., Seppelt, K., Strauss, S. H., Boltalina, O. V. & Dunsch, L. (2007). J. Am. Chem. Soc. 129, 11551–11568.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationPowell, W. H., Cozzi, F., Moss, G. P., Thilgen, C., Hwu, R. J.-R. & Yerin, A. (2002). Pure Appl. Chem. 74, 629–695.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
First citationTroyanov, S. I., Dimitrov, A. & Kemnitz, E. (2006). Angew. Chem. Int. Ed. 45, 1971–1974.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds