1,6,11,16,18,24,27,36-Octakis(trifluoromethyl)-1,6,11,16,18,24,27,36-octahydro(C₆₀–I_h)[5,6]fullerene deuterochloroform solvate

Abstract

Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.003 Å; R factor = 0.054; wR factor = 0.150; data-to-parameter ratio = 18.9.The title compound, C 68 F 24 ÁCDCl 3 , is a solvate of one of five isomers of C 60 (CF 3 ) 8 that have now been isolated. The fullerene molecule has an idealized I h C 60 core with the eight CF 3 groups arranged in an asymmetric fashion on a parapara-para-meta-para-meta-para ribbon of edge-sharing C 6 (CF 3 ) 2 hexagons. There are no cage Csp 3 -Csp 3 bonds. There are intramolecular FÁ Á ÁF contacts between pairs of CF 3 groups on the same hexagon, in the range 2.544 (2)-2.641 (2) Å . Related literatureFor 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 Crystal data C 68 F 24 ÁCDCl 3 M r = 1393.05 Monoclinic, P2 1 =c a = 14.5346 (6) Å b = 15.5805 (7) Å c = 20.1746 (9) Å = 99.821 (2) V = 4501.7 (3) Å 3 Z = 4 Mo K radiation = 0.36 mm À1 T = 100 (2) K 0.34 Â 0.20 Â 0.05 mm Data collection Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000) T min = 0.888, T max = 0.982 99651 measured reflections 16373 independent reflections 10149 reflections with I > 2(I) R int = 0.058Refinement R[F 2 > 2(F 2 )] = 0.054 wR(F 2 ) = 0.150 S = 1.03 16373 reflections 865 parameters Á max = 0.81 e Å À3 Á min = À1.31 e Å À3

Perfluoroalkylfullerenes

“…To date there are are two structurally characterized C 60 (CF 3 ) 8 isomers with ribbon addition patterns, 60-8-1 and 60-8-4 , and three with p 3 mp , p addition patterns, 60-8-2 , 60-8-3 , and 60-8-5 , all with 0–11 kJ·mol −1 Δ E values. ,,, Several isomers that have not been structurally characterized have also been isolated.…”

Synthesis of highly functionalized C60 fullerene derivatives and their applications in material and life sciences

“…Some of them, such as octakis(trifluoromethyl)octakishydrido fullerene were characterized by X-ray crystallography. 105,106…”

High-temperature and photochemical syntheses of C60 and C70 fullerene derivatives with linear perfluoroalkyl chains

“…addition patterns, not only for C 60 and C 70 [2,3] but also for higher fullerenes, [4,5] and endo hedral metallofullerenes [6,7]. Due to the ease with which fullerene(CF 3 ) n can form well-ordered single crystals by simple solvent evaporation, several dozen X-raydetermined structures are known by now [1][2][3][4][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. Even when TMFs do not form suitable crystals for crystallography, 19 F NMR spectroscopy coupled with DFT calculations serves as a very valuable tool for structural elucidations [4,8].…”