1,4,7,11,18,21,24,31,35,39,51,58,61,64-Tetra­deca­kis(trifluoro­meth­yl)-1,4,7,11,18,21,24,31,35,39,51,58,61,64-tetra­deca­hydro­(C70–D5h)[5,6]fullerene p-xylene tris­olvate

Shustova, N.B.; Peryshkov, D.V.; Kareev, I.E.; Boltalina, O.V.; Strauss, S.H.

doi:10.1107/S1600536807040755

1,4,7,11,18,21,24,31,35,39,51,58,61,64-Tetradecakis(trifluoromethyl)-1,4,7,11,18,21,24,31,35,39,51,58,61,64-tetradecahydro(C₇₀–D_5h)[5,6]fullerene p-xylene trisolvate

N. B. Shustova, D. V. Peryshkov, I. E. Kareev, O. V. Boltalina and S. H. Strauss

The title compound, C₈₄F₄₂·3C₈H₁₀, features one of five isomers of C₇₀(CF₃)₁₄ that have been isolated. The fullerene molecule, which has crystallographic C₂ symmetry, consists of an idealized D_5h–C₇₀ core with the 14 CF₃ groups arranged in an asymmetric fashion on a para–para–para–para–para–para–para–meta–para (p⁷mp) ribbon and a para–meta–para (pmp) ribbon of edge-sharing C₆(CF₃)₂ hexagons such that the two ribbons connect to one another, forming two 1,3-C₅(CF₃)₂ pentagons. 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040755/wk2073sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040755/wk2073Isup2.hkl Contains datablock I

CCDC reference: 663667

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.055
wR factor = 0.161
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom F413    has ADP max/min Ratio .............       3.10 prola
PLAT213_ALERT_2_C Atom F421    has ADP max/min Ratio .............       3.10 prola
PLAT213_ALERT_2_C Atom C21     has ADP max/min Ratio .............       3.10 oblat
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C41
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C42
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.32
PLAT320_ALERT_2_C Check Hybridisation of  C7     in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C8     in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C10    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C15    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C16    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C17    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C18    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C19    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C20    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C21    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C22    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C27    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C28    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C32    in Main Residue .          ?
PLAT320_ALERT_2_C Check Hybridisation of  C33    in Main Residue .          ?
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C7     -   C8     ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C10    -   C11    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C12    -   C22    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C14    -   C15    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C16    -   C17    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C18    -   C19    ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C20    -   C21    ...       1.39 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C27    -   C28    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C32    -   C33    ...       1.39 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      36.00 A   3 

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C9     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C13    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C23    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C26    = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  34 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  31 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 C₇₀ with CF₃I have yielded twenty-five 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 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 et al., 2007). A member of the n = 14 set of five isomers, the title compound, (I), has been crystallized from p-xylene and we report its crystal structure here. A much lower-quality structure (C—C su's 0.015–0.019 Å, R₁ = 0.186, wR₂ = 0.41) of the same fullerene molecule as a hexane solvate has recently been reported (Goryunkov et al., 2006).

The structure of (I), Figs. 1 and 2, comprises an idealized D_{5 h} C₇₀ core with fourteen sp³ carbon atoms at positions 1, 4, 7, 11, 18, 21, 24, 31, 35, 39, 51, 58, 61, and 64 (Powell et al., 2002), each of which is attached to a CF₃ group. The molecule has crystallographic C₂ symmetry; symmetry related atoms have the letter a after the atom number. The core sp³ carbon atoms are not adjacent to one another. The CF₃ groups are arranged on a para-para-para-para-para-para-para- meta-para (p⁷mp) ribbon and a para-meta-para (pmp) ribbon of edge-sharing C₆(CF₃)₂ hexagons such that the two ribbons connect to one another, forming two 1,3-C₅(CF₃)₂ pentagons (see Schlegel diagram in Fig. 2). 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 two ribbons 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 2.560 (3) to 2.876 (3) Å.

The four shortest cage C—C bonds (two pairs) in (I) are C1—C6a/C1a—C6, at 1.347 (3) Å, and C3—C4/C3a—C4a, at 1.356 (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, the C1—C6a and C1a—C6 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: Avdoshenko et al. (2006); Goryunkov et al. (2006); Ignat'eva et al. (2006); Kareev et al. (2005, 2006a,b); Olmstead et al. (2003); Popov et al. (2007); Powell et al. (2002).

Experimental top

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

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); 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

	Fig. 1. (Left) The molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level. (Right) The numbering scheme of (I). The crystallographic C₂ axis passes through the hexagon containing C29, C29a, C31, and C31a (symmetry related atoms have the letter a after the atom number).
	Fig. 2. 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 of meta- and para-C₆(CF₃)₂ edge-sharing hexagons (meta-C₆(CF₃)₂ hexagons are indicated by the letter m).

1,4,7,11,18,21,24,31,35,39,51,58,61,64-Tetradecakis(trifluoromethyl)- 1,4,7,11,18,21,24,31,35,39,51,58,61,64- tetradecahydro(C₇₀—D_{5 h})[5,6]fullerene p-xylene trisolvate top

Crystal data top

C₈₄F₄₂·3C₈H₁₀	F(000) = 4224
M_r = 2125.32	D_x = 1.811 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.4423 (16) Å	Cell parameters from 999 reflections
b = 14.1495 (7) Å	θ = 1.7–27.9°
c = 22.6519 (11) Å	µ = 0.18 mm⁻¹
β = 107.070 (5)°	T = 100 K
V = 7795.4 (7) Å³	Rhombic, orange
Z = 4	0.40 × 0.23 × 0.09 mm

Data collection top

Bruker Kappa APEX II diffractometer	9305 independent reflections
Radiation source: fine-focus sealed tube	6651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
φ and ω scans	θ_max = 27.9°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS, Bruker, 2000)	h = −33→33
T_min = 0.933, T_max = 0.984	k = −18→18
130931 measured reflections	l = −29→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0719P)² + 26.7468P] where P = (F_o² + 2F_c²)/3
9305 reflections	(Δ/σ)_max = 0.001
679 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₈₄F₄₂·3C₈H₁₀	V = 7795.4 (7) Å³
M_r = 2125.32	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 25.4423 (16) Å	µ = 0.18 mm⁻¹
b = 14.1495 (7) Å	T = 100 K
c = 22.6519 (11) Å	0.40 × 0.23 × 0.09 mm
β = 107.070 (5)°

Data collection top

Bruker Kappa APEX II diffractometer	9305 independent reflections
Absorption correction: multi-scan (SADABS, Bruker, 2000)	6651 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.984	R_int = 0.066
130931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0719P)² + 26.7468P] where P = (F_o² + 2F_c²)/3
9305 reflections	Δρ_max = 0.53 e Å⁻³
679 parameters	Δρ_min = −0.53 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C1	−0.08268 (11)	0.48440 (17)	0.79209 (11)	0.0160 (5)
C2	−0.03691 (10)	0.46569 (17)	0.85024 (11)	0.0155 (5)
C3	0.01826 (10)	0.46278 (16)	0.83587 (11)	0.0154 (5)
C4	0.02365 (10)	0.44834 (16)	0.77873 (11)	0.0147 (5)
C5	0.08103 (11)	0.45187 (17)	0.77182 (11)	0.0160 (5)
C6	0.12112 (10)	0.55193 (17)	0.71344 (11)	0.0160 (5)
C7	−0.15208 (10)	0.74444 (18)	0.75467 (11)	0.0169 (5)
C8	−0.13424 (10)	0.71890 (17)	0.81628 (11)	0.0166 (5)
C9	−0.12683 (10)	0.61496 (17)	0.83788 (11)	0.0163 (5)
C10	−0.07032 (10)	0.61925 (18)	0.88728 (11)	0.0157 (5)
C11	−0.02992 (11)	0.55333 (17)	0.89099 (11)	0.0152 (5)
C12	0.02623 (10)	0.57981 (17)	0.91181 (10)	0.0147 (5)
C13	0.06281 (11)	0.51229 (17)	0.88946 (11)	0.0171 (5)
C14	0.10346 (10)	0.56652 (17)	0.86427 (11)	0.0145 (5)
C15	0.11537 (10)	0.52832 (17)	0.81343 (11)	0.0155 (5)
C16	0.14151 (10)	0.58187 (18)	0.77804 (11)	0.0166 (5)
C17	0.15683 (10)	0.67436 (18)	0.79395 (11)	0.0166 (5)
C18	−0.07696 (11)	0.85962 (17)	0.83726 (11)	0.0170 (5)
C19	−0.09497 (11)	0.77643 (18)	0.85807 (11)	0.0166 (5)
C20	−0.05573 (10)	0.71536 (17)	0.90126 (10)	0.0154 (5)
C21	−0.00067 (11)	0.74112 (17)	0.92113 (10)	0.0157 (5)
C22	0.04088 (10)	0.67163 (17)	0.92801 (10)	0.0152 (5)
C23	0.09401 (10)	0.71747 (17)	0.92343 (11)	0.0157 (5)
C24	0.11795 (10)	0.66342 (17)	0.87978 (11)	0.0148 (5)
C25	0.14403 (10)	0.71565 (17)	0.84463 (11)	0.0157 (5)
C26	0.13972 (11)	0.82482 (17)	0.83513 (11)	0.0167 (5)
C27	0.13535 (10)	0.83146 (17)	0.76627 (11)	0.0164 (5)
C28	0.09857 (11)	0.88846 (17)	0.72555 (11)	0.0169 (5)
C29	0.05705 (11)	0.95174 (17)	0.74390 (12)	0.0177 (5)
C30	0.04806 (11)	0.91925 (17)	0.80457 (11)	0.0168 (5)
C31	−0.00411 (11)	0.93096 (16)	0.81014 (11)	0.0176 (5)
C32	−0.01942 (11)	0.88503 (16)	0.85809 (11)	0.0162 (5)
C33	0.01818 (11)	0.82719 (17)	0.89960 (11)	0.0160 (5)
C34	0.07156 (11)	0.81482 (17)	0.89430 (11)	0.0164 (5)
C35	0.08718 (10)	0.85996 (17)	0.84767 (11)	0.0158 (5)
C36	−0.04668 (12)	0.37394 (19)	0.88469 (12)	0.0224 (6)
C37	0.10842 (12)	0.35315 (18)	0.78534 (12)	0.0211 (5)
C38	−0.17389 (11)	0.58456 (19)	0.86314 (12)	0.0216 (5)
C39	0.09405 (11)	0.44407 (19)	0.94399 (12)	0.0214 (6)
C40	0.13581 (11)	0.72325 (18)	0.98796 (11)	0.0194 (5)
C41	0.19157 (11)	0.87962 (19)	0.87432 (12)	0.0209 (5)
C42	0.07547 (12)	1.05667 (18)	0.74822 (12)	0.0223 (6)
C43	0.21133 (13)	−0.0831 (3)	0.15373 (16)	0.0399 (8)
C44	0.22565 (14)	−0.0842 (3)	0.09892 (17)	0.0431 (9)
H44	0.2274	−0.1419	0.0798	0.052*
C45	0.23724 (14)	−0.0025 (3)	0.07215 (18)	0.0452 (9)
H45	0.2460	−0.0059	0.0351	0.054*
C46	0.23610 (15)	0.0854 (3)	0.0997 (2)	0.0483 (9)
C47	0.22347 (15)	0.0864 (3)	0.1556 (2)	0.0505 (10)
H47	0.2231	0.1437	0.1756	0.061*
C48	0.21147 (15)	0.0043 (3)	0.18204 (18)	0.0452 (9)
H48	0.2033	0.0075	0.2194	0.054*
C49	0.19740 (16)	−0.1722 (3)	0.18156 (19)	0.0495 (10)
H49A	0.1602	−0.1901	0.1605	0.074*
H49B	0.2011	−0.1619	0.2245	0.074*
H49C	0.2219	−0.2217	0.1775	0.074*
C50	0.24732 (19)	0.1753 (3)	0.0697 (2)	0.0653 (13)
H50A	0.2131	0.2028	0.0460	0.098*
H50B	0.2694	0.1613	0.0430	0.098*
H50C	0.2665	0.2191	0.1011	0.098*
C51	0.04232 (15)	0.0553 (2)	−0.01127 (15)	0.0338 (7)
C52	0.05432 (14)	−0.0201 (2)	0.03007 (14)	0.0339 (7)
H52	0.0908	−0.0345	0.0507	0.041*
C53	0.01247 (15)	−0.0740 (2)	0.04073 (14)	0.0342 (7)
H53	0.0215	−0.1241	0.0685	0.041*
C54	0.08786 (19)	0.1138 (3)	−0.0231 (2)	0.0563 (11)
H54A	0.0777	0.1322	−0.0658	0.084*
H54B	0.1210	0.0771	−0.0136	0.084*
H54C	0.0938	0.1692	0.0024	0.084*
F361	−0.10036 (7)	0.35690 (12)	0.87384 (8)	0.0321 (4)
F362	−0.02505 (8)	0.38325 (12)	0.94590 (7)	0.0316 (4)
F363	−0.02429 (7)	0.29735 (11)	0.86770 (8)	0.0287 (4)
F371	0.11667 (8)	0.32738 (12)	0.84394 (8)	0.0348 (4)
F372	0.07692 (8)	0.28743 (11)	0.74981 (8)	0.0325 (4)
F373	0.15695 (7)	0.35158 (12)	0.77421 (9)	0.0330 (4)
F381	−0.16901 (7)	0.49526 (11)	0.88247 (7)	0.0266 (4)
F382	−0.17586 (7)	0.63905 (12)	0.91103 (8)	0.0291 (4)
F383	−0.22224 (7)	0.59329 (13)	0.81948 (8)	0.0302 (4)
F391	0.07719 (8)	0.35491 (12)	0.93486 (8)	0.0322 (4)
F392	0.14813 (7)	0.44451 (13)	0.95243 (8)	0.0316 (4)
F393	0.08619 (7)	0.47138 (12)	0.99746 (7)	0.0284 (4)
F401	0.14444 (7)	0.63742 (12)	1.01375 (7)	0.0278 (4)
F402	0.18459 (7)	0.75489 (14)	0.98599 (7)	0.0337 (4)
F403	0.11813 (7)	0.77886 (12)	1.02572 (7)	0.0266 (4)
F411	0.23546 (8)	0.82497 (14)	0.88972 (11)	0.0487 (6)
F412	0.20312 (9)	0.95185 (15)	0.84387 (9)	0.0495 (6)
F413	0.18514 (9)	0.91388 (17)	0.92594 (9)	0.0493 (6)
F421	0.05096 (11)	1.10843 (13)	0.78088 (12)	0.0590 (7)
F422	0.12873 (8)	1.06442 (13)	0.77648 (11)	0.0484 (6)
F423	0.06605 (9)	1.09499 (12)	0.69320 (8)	0.0439 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0224 (13)	0.0140 (11)	0.0110 (11)	−0.0045 (9)	0.0042 (10)	−0.0001 (9)
C2	0.0215 (13)	0.0143 (11)	0.0110 (11)	−0.0005 (9)	0.0053 (10)	−0.0005 (9)
C3	0.0228 (13)	0.0099 (10)	0.0128 (11)	0.0008 (9)	0.0041 (10)	0.0033 (9)
C4	0.0228 (13)	0.0079 (10)	0.0131 (11)	0.0004 (9)	0.0051 (10)	0.0016 (9)
C5	0.0223 (13)	0.0145 (11)	0.0109 (11)	0.0018 (9)	0.0044 (10)	−0.0002 (9)
C6	0.0201 (13)	0.0156 (11)	0.0128 (11)	0.0047 (9)	0.0056 (10)	0.0000 (9)
C7	0.0173 (12)	0.0195 (12)	0.0147 (12)	0.0039 (9)	0.0060 (10)	0.0010 (10)
C8	0.0184 (12)	0.0176 (12)	0.0153 (12)	0.0032 (9)	0.0074 (10)	0.0017 (9)
C9	0.0204 (12)	0.0170 (12)	0.0124 (11)	−0.0001 (9)	0.0063 (10)	0.0005 (9)
C10	0.0208 (13)	0.0187 (12)	0.0085 (11)	−0.0019 (9)	0.0057 (9)	0.0016 (9)
C11	0.0242 (13)	0.0135 (11)	0.0083 (11)	−0.0007 (9)	0.0055 (9)	0.0027 (9)
C12	0.0221 (13)	0.0152 (11)	0.0064 (10)	0.0014 (9)	0.0037 (9)	0.0027 (9)
C13	0.0227 (13)	0.0155 (11)	0.0122 (11)	0.0027 (10)	0.0038 (10)	0.0003 (9)
C14	0.0167 (12)	0.0154 (11)	0.0092 (11)	0.0016 (9)	0.0004 (9)	0.0032 (9)
C15	0.0179 (12)	0.0142 (11)	0.0125 (11)	0.0022 (9)	0.0013 (9)	0.0010 (9)
C16	0.0192 (12)	0.0183 (12)	0.0107 (11)	0.0034 (9)	0.0020 (9)	0.0000 (9)
C17	0.0176 (12)	0.0195 (12)	0.0123 (11)	−0.0006 (9)	0.0038 (9)	−0.0002 (9)
C18	0.0243 (13)	0.0143 (11)	0.0132 (12)	0.0043 (10)	0.0067 (10)	−0.0029 (9)
C19	0.0211 (13)	0.0186 (12)	0.0121 (11)	0.0037 (10)	0.0080 (10)	−0.0012 (9)
C20	0.0234 (13)	0.0179 (12)	0.0060 (10)	0.0020 (10)	0.0060 (9)	0.0005 (9)
C21	0.0277 (14)	0.0157 (11)	0.0041 (10)	0.0008 (10)	0.0052 (9)	−0.0021 (8)
C22	0.0207 (12)	0.0189 (12)	0.0055 (10)	0.0002 (9)	0.0031 (9)	0.0010 (9)
C23	0.0218 (13)	0.0156 (11)	0.0076 (11)	0.0001 (9)	0.0008 (9)	−0.0020 (9)
C24	0.0163 (12)	0.0178 (11)	0.0080 (11)	0.0015 (9)	−0.0004 (9)	−0.0002 (9)
C25	0.0166 (12)	0.0167 (11)	0.0118 (11)	−0.0001 (9)	0.0012 (9)	−0.0015 (9)
C26	0.0213 (13)	0.0150 (11)	0.0130 (11)	−0.0033 (9)	0.0039 (10)	−0.0006 (9)
C27	0.0195 (12)	0.0160 (11)	0.0140 (12)	−0.0059 (9)	0.0055 (10)	−0.0015 (9)
C28	0.0238 (13)	0.0121 (11)	0.0155 (12)	−0.0065 (9)	0.0071 (10)	−0.0009 (9)
C29	0.0263 (14)	0.0104 (11)	0.0161 (12)	−0.0034 (9)	0.0057 (10)	0.0002 (9)
C30	0.0272 (13)	0.0105 (10)	0.0120 (11)	−0.0023 (9)	0.0048 (10)	−0.0028 (9)
C31	0.0295 (14)	0.0090 (11)	0.0132 (11)	−0.0001 (9)	0.0047 (10)	−0.0031 (9)
C32	0.0270 (13)	0.0106 (10)	0.0128 (11)	0.0016 (9)	0.0084 (10)	−0.0040 (9)
C33	0.0258 (13)	0.0135 (11)	0.0084 (11)	−0.0005 (9)	0.0046 (9)	−0.0037 (9)
C34	0.0245 (13)	0.0139 (11)	0.0090 (11)	−0.0015 (9)	0.0023 (10)	−0.0047 (9)
C35	0.0235 (13)	0.0115 (11)	0.0116 (11)	−0.0035 (9)	0.0041 (10)	−0.0041 (9)
C36	0.0321 (15)	0.0191 (13)	0.0156 (12)	−0.0020 (11)	0.0064 (11)	0.0012 (10)
C37	0.0288 (14)	0.0174 (12)	0.0164 (12)	0.0039 (10)	0.0057 (11)	0.0010 (10)
C38	0.0238 (14)	0.0245 (13)	0.0165 (12)	0.0005 (11)	0.0060 (10)	0.0021 (10)
C39	0.0262 (14)	0.0230 (13)	0.0144 (12)	0.0020 (10)	0.0047 (11)	0.0030 (10)
C40	0.0246 (14)	0.0213 (13)	0.0113 (11)	−0.0010 (10)	0.0037 (10)	−0.0031 (10)
C41	0.0261 (14)	0.0202 (13)	0.0156 (12)	−0.0041 (10)	0.0050 (11)	−0.0022 (10)
C42	0.0353 (16)	0.0144 (12)	0.0177 (13)	−0.0028 (10)	0.0086 (11)	−0.0003 (10)
C43	0.0211 (15)	0.056 (2)	0.0365 (18)	0.0034 (14)	−0.0006 (13)	−0.0158 (16)
C44	0.0291 (17)	0.051 (2)	0.043 (2)	−0.0020 (15)	0.0020 (15)	−0.0232 (17)
C45	0.0315 (18)	0.058 (2)	0.040 (2)	0.0035 (16)	0.0015 (15)	−0.0123 (17)
C46	0.0283 (18)	0.052 (2)	0.058 (2)	0.0107 (16)	0.0031 (16)	−0.0054 (19)
C47	0.0340 (19)	0.051 (2)	0.063 (3)	0.0080 (16)	0.0097 (18)	−0.023 (2)
C48	0.0332 (19)	0.055 (2)	0.046 (2)	0.0074 (16)	0.0085 (16)	−0.0174 (18)
C49	0.0344 (19)	0.060 (2)	0.053 (2)	−0.0050 (17)	0.0109 (17)	−0.0171 (19)
C50	0.049 (2)	0.058 (3)	0.086 (3)	0.017 (2)	0.015 (2)	0.007 (2)
C51	0.048 (2)	0.0254 (15)	0.0297 (16)	0.0011 (13)	0.0140 (14)	−0.0090 (12)
C52	0.0391 (18)	0.0298 (16)	0.0267 (16)	0.0115 (13)	0.0003 (13)	−0.0101 (12)
C53	0.057 (2)	0.0219 (14)	0.0213 (14)	0.0087 (14)	0.0083 (14)	−0.0019 (11)
C54	0.067 (3)	0.044 (2)	0.069 (3)	−0.0063 (19)	0.037 (2)	−0.009 (2)
F361	0.0343 (10)	0.0280 (9)	0.0369 (10)	−0.0051 (7)	0.0151 (8)	0.0093 (7)
F362	0.0511 (11)	0.0265 (9)	0.0158 (8)	−0.0014 (8)	0.0077 (7)	0.0056 (7)
F363	0.0446 (10)	0.0162 (7)	0.0276 (9)	0.0019 (7)	0.0142 (8)	0.0027 (6)
F371	0.0533 (12)	0.0298 (9)	0.0206 (8)	0.0159 (8)	0.0095 (8)	0.0085 (7)
F372	0.0421 (10)	0.0163 (8)	0.0334 (10)	0.0005 (7)	0.0024 (8)	−0.0031 (7)
F373	0.0310 (10)	0.0277 (9)	0.0425 (11)	0.0119 (7)	0.0140 (8)	0.0057 (8)
F381	0.0309 (9)	0.0241 (8)	0.0273 (9)	−0.0027 (7)	0.0120 (7)	0.0070 (7)
F382	0.0342 (9)	0.0347 (9)	0.0243 (9)	0.0018 (7)	0.0178 (7)	−0.0009 (7)
F383	0.0211 (8)	0.0432 (10)	0.0247 (9)	−0.0023 (7)	0.0043 (7)	0.0092 (7)
F391	0.0465 (11)	0.0221 (8)	0.0243 (9)	0.0002 (7)	0.0047 (8)	0.0056 (7)
F392	0.0274 (9)	0.0383 (10)	0.0278 (9)	0.0090 (7)	0.0062 (7)	0.0111 (7)
F393	0.0391 (10)	0.0326 (9)	0.0126 (7)	0.0083 (7)	0.0060 (7)	0.0034 (6)
F401	0.0351 (9)	0.0268 (8)	0.0140 (8)	0.0043 (7)	−0.0044 (7)	0.0035 (6)
F402	0.0257 (9)	0.0562 (12)	0.0173 (8)	−0.0161 (8)	0.0033 (7)	−0.0080 (8)
F403	0.0341 (9)	0.0311 (9)	0.0115 (7)	0.0038 (7)	0.0018 (6)	−0.0074 (6)
F411	0.0236 (10)	0.0376 (11)	0.0690 (15)	0.0009 (8)	−0.0112 (9)	−0.0171 (10)
F412	0.0535 (13)	0.0463 (12)	0.0342 (11)	−0.0352 (10)	−0.0097 (9)	0.0147 (9)
F413	0.0475 (12)	0.0731 (15)	0.0312 (10)	−0.0330 (11)	0.0174 (9)	−0.0349 (10)
F421	0.1002 (19)	0.0159 (9)	0.0904 (18)	−0.0115 (10)	0.0739 (16)	−0.0133 (10)
F422	0.0388 (11)	0.0223 (9)	0.0680 (14)	−0.0106 (8)	−0.0094 (10)	−0.0040 (9)
F423	0.0774 (15)	0.0232 (9)	0.0219 (9)	−0.0229 (9)	0.0001 (9)	0.0078 (7)

Geometric parameters (Å, º) top

C1—C6ⁱ	1.346 (4)	C29—C42	1.551 (3)
C1—C2	1.504 (3)	C29—C31ⁱ	1.559 (4)
C1—C5ⁱ	1.532 (3)	C30—C31	1.380 (4)
C2—C11	1.525 (3)	C30—C35	1.441 (3)
C2—C3	1.532 (4)	C31—C32	1.415 (4)
C2—C36	1.572 (3)	C31—C29ⁱ	1.559 (4)
C3—C4	1.356 (3)	C32—C33	1.393 (3)
C3—C13	1.562 (3)	C33—C34	1.409 (4)
C4—C4ⁱ	1.491 (5)	C34—C35	1.388 (4)
C4—C5	1.514 (4)	C36—F363	1.333 (3)
C5—C15	1.529 (3)	C36—F361	1.337 (3)
C5—C1ⁱ	1.532 (3)	C36—F362	1.340 (3)
C5—C37	1.551 (3)	C37—F373	1.331 (3)
C6—C1ⁱ	1.346 (4)	C37—F371	1.333 (3)
C6—C16	1.464 (3)	C37—F372	1.333 (3)
C6—C9ⁱ	1.506 (3)	C38—F381	1.331 (3)
C7—C8	1.383 (3)	C38—F383	1.339 (3)
C7—C27ⁱ	1.429 (4)	C38—F382	1.344 (3)
C7—C17ⁱ	1.460 (3)	C39—F391	1.329 (3)
C8—C19	1.415 (4)	C39—F392	1.332 (3)
C8—C9	1.544 (3)	C39—F393	1.341 (3)
C9—C6ⁱ	1.506 (3)	C40—F402	1.332 (3)
C9—C38	1.532 (4)	C40—F403	1.334 (3)
C9—C10	1.542 (3)	C40—F401	1.338 (3)
C10—C11	1.372 (4)	C41—F412	1.314 (3)
C10—C20	1.421 (3)	C41—F411	1.318 (3)
C11—C12	1.417 (4)	C41—F413	1.319 (3)
C12—C22	1.372 (3)	C42—F423	1.315 (3)
C12—C13	1.521 (3)	C42—F421	1.321 (3)
C13—C14	1.526 (4)	C42—F422	1.322 (3)
C13—C39	1.585 (3)	C43—C44	1.393 (5)
C14—C15	1.384 (3)	C43—C48	1.393 (5)
C14—C24	1.436 (3)	C43—C49	1.498 (6)
C15—C16	1.404 (4)	C44—C45	1.378 (6)
C16—C17	1.383 (4)	C44—H44	0.9300
C17—C25	1.409 (3)	C45—C46	1.396 (5)
C17—C7ⁱ	1.460 (3)	C45—H45	0.9300
C18—C19	1.394 (4)	C46—C47	1.394 (6)
C18—C28ⁱ	1.426 (3)	C46—C50	1.509 (6)
C18—C32	1.445 (4)	C47—C48	1.380 (6)
C19—C20	1.459 (3)	C47—H47	0.9300
C20—C21	1.389 (4)	C48—H48	0.9300
C21—C22	1.418 (3)	C49—H49A	0.9600
C21—C33	1.445 (3)	C49—H49B	0.9600
C22—C23	1.530 (4)	C49—H49C	0.9600
C23—C24	1.513 (3)	C50—H50A	0.9600
C23—C40	1.537 (3)	C50—H50B	0.9600
C23—C34	1.561 (3)	C50—H50C	0.9600
C24—C25	1.389 (4)	C51—C53ⁱⁱ	1.383 (5)
C25—C26	1.559 (3)	C51—C52	1.393 (5)
C26—C35	1.529 (4)	C51—C54	1.511 (5)
C26—C27	1.534 (3)	C52—C53	1.387 (5)
C26—C41	1.563 (4)	C52—H52	0.9300
C27—C28	1.368 (4)	C53—C51ⁱⁱ	1.383 (5)
C27—C7ⁱ	1.429 (4)	C53—H53	0.9300
C28—C18ⁱ	1.426 (3)	C54—H54A	0.9600
C28—C29	1.532 (4)	C54—H54B	0.9600
C29—C30	1.529 (3)	C54—H54C	0.9600

C6ⁱ—C1—C2	124.1 (2)	C42—C29—C31ⁱ	113.9 (2)
C6ⁱ—C1—C5ⁱ	110.2 (2)	C31—C30—C35	120.0 (2)
C2—C1—C5ⁱ	123.1 (2)	C31—C30—C29	116.6 (2)
C1—C2—C11	108.1 (2)	C35—C30—C29	121.9 (2)
C1—C2—C3	109.9 (2)	C30—C31—C32	120.3 (2)
C11—C2—C3	101.5 (2)	C30—C31—C29ⁱ	125.7 (2)
C1—C2—C36	112.7 (2)	C32—C31—C29ⁱ	108.7 (2)
C11—C2—C36	112.2 (2)	C33—C32—C31	119.9 (2)
C3—C2—C36	111.8 (2)	C33—C32—C18	120.2 (2)
C4—C3—C2	124.2 (2)	C31—C32—C18	110.1 (2)
C4—C3—C13	123.7 (2)	C32—C33—C34	120.2 (2)
C2—C3—C13	108.9 (2)	C32—C33—C21	119.5 (2)
C3—C4—C4ⁱ	123.5 (3)	C34—C33—C21	110.3 (2)
C3—C4—C5	117.7 (2)	C35—C34—C33	120.4 (2)
C4ⁱ—C4—C5	117.7 (3)	C35—C34—C23	125.2 (2)
C4—C5—C15	110.7 (2)	C33—C34—C23	108.4 (2)
C4—C5—C1ⁱ	113.7 (2)	C34—C35—C30	119.2 (2)
C15—C5—C1ⁱ	101.6 (2)	C34—C35—C26	116.9 (2)
C4—C5—C37	109.9 (2)	C30—C35—C26	122.1 (2)
C15—C5—C37	111.9 (2)	F363—C36—F361	107.5 (2)
C1ⁱ—C5—C37	108.8 (2)	F363—C36—F362	107.4 (2)
C1ⁱ—C6—C16	109.4 (2)	F361—C36—F362	107.2 (2)
C1ⁱ—C6—C9ⁱ	125.5 (2)	F363—C36—C2	112.7 (2)
C16—C6—C9ⁱ	120.9 (2)	F361—C36—C2	111.1 (2)
C8—C7—C27ⁱ	121.2 (2)	F362—C36—C2	110.9 (2)
C8—C7—C17ⁱ	120.9 (2)	F373—C37—F371	107.5 (2)
C27ⁱ—C7—C17ⁱ	107.5 (2)	F373—C37—F372	107.5 (2)
C7—C8—C19	118.9 (2)	F371—C37—F372	107.5 (2)
C7—C8—C9	122.8 (2)	F373—C37—C5	111.5 (2)
C19—C8—C9	109.9 (2)	F371—C37—C5	111.9 (2)
C6ⁱ—C9—C38	112.7 (2)	F372—C37—C5	110.7 (2)
C6ⁱ—C9—C10	107.6 (2)	F381—C38—F383	107.9 (2)
C38—C9—C10	113.8 (2)	F381—C38—F382	107.5 (2)
C6ⁱ—C9—C8	110.5 (2)	F383—C38—F382	107.4 (2)
C38—C9—C8	110.5 (2)	F381—C38—C9	112.4 (2)
C10—C9—C8	101.2 (2)	F383—C38—C9	110.3 (2)
C11—C10—C20	119.7 (2)	F382—C38—C9	111.0 (2)
C11—C10—C9	122.7 (2)	F391—C39—F392	107.4 (2)
C20—C10—C9	109.1 (2)	F391—C39—F393	106.7 (2)
C10—C11—C12	120.3 (2)	F392—C39—F393	106.9 (2)
C10—C11—C2	124.3 (2)	F391—C39—C13	113.1 (2)
C12—C11—C2	110.1 (2)	F392—C39—C13	111.7 (2)
C22—C12—C11	120.5 (2)	F393—C39—C13	110.8 (2)
C22—C12—C13	122.7 (2)	F402—C40—F403	108.4 (2)
C11—C12—C13	112.3 (2)	F402—C40—F401	106.5 (2)
C12—C13—C14	110.9 (2)	F403—C40—F401	107.4 (2)
C12—C13—C3	99.5 (2)	F402—C40—C23	112.2 (2)
C14—C13—C3	110.6 (2)	F403—C40—C23	111.8 (2)
C12—C13—C39	109.8 (2)	F401—C40—C23	110.3 (2)
C14—C13—C39	111.0 (2)	F412—C41—F411	107.0 (2)
C3—C13—C39	114.6 (2)	F412—C41—F413	106.5 (2)
C15—C14—C24	118.2 (2)	F411—C41—F413	107.3 (2)
C15—C14—C13	116.9 (2)	F412—C41—C26	111.7 (2)
C24—C14—C13	122.8 (2)	F411—C41—C26	111.6 (2)
C14—C15—C16	121.4 (2)	F413—C41—C26	112.5 (2)
C14—C15—C5	124.3 (2)	F423—C42—F421	108.5 (2)
C16—C15—C5	108.1 (2)	F423—C42—F422	107.5 (2)
C17—C16—C15	120.4 (2)	F421—C42—F422	105.6 (2)
C17—C16—C6	121.6 (2)	F423—C42—C29	111.5 (2)
C15—C16—C6	109.0 (2)	F421—C42—C29	112.5 (2)
C16—C17—C25	119.3 (2)	F422—C42—C29	111.0 (2)
C16—C17—C7ⁱ	119.4 (2)	C44—C43—C48	117.1 (4)
C25—C17—C7ⁱ	110.2 (2)	C44—C43—C49	121.4 (3)
C19—C18—C28ⁱ	120.7 (2)	C48—C43—C49	121.5 (3)
C19—C18—C32	120.1 (2)	C45—C44—C43	121.9 (3)
C28ⁱ—C18—C32	108.1 (2)	C45—C44—H44	119.1
C18—C19—C8	119.8 (2)	C43—C44—H44	119.1
C18—C19—C20	119.9 (2)	C44—C45—C46	121.1 (4)
C8—C19—C20	108.5 (2)	C44—C45—H45	119.5
C21—C20—C10	119.8 (2)	C46—C45—H45	119.5
C21—C20—C19	119.3 (2)	C47—C46—C45	117.1 (4)
C10—C20—C19	109.6 (2)	C47—C46—C50	121.7 (4)
C20—C21—C22	120.1 (2)	C45—C46—C50	121.2 (4)
C20—C21—C33	121.0 (2)	C48—C47—C46	121.7 (4)
C22—C21—C33	108.1 (2)	C48—C47—H47	119.2
C12—C22—C21	119.5 (2)	C46—C47—H47	119.2
C12—C22—C23	124.0 (2)	C47—C48—C43	121.2 (4)
C21—C22—C23	110.1 (2)	C47—C48—H48	119.4
C24—C23—C22	111.3 (2)	C43—C48—H48	119.4
C24—C23—C40	110.5 (2)	C43—C49—H49A	109.5
C22—C23—C40	109.7 (2)	C43—C49—H49B	109.5
C24—C23—C34	109.71 (19)	H49A—C49—H49B	109.5
C22—C23—C34	100.5 (2)	C43—C49—H49C	109.5
C40—C23—C34	114.9 (2)	H49A—C49—H49C	109.5
C25—C24—C14	119.9 (2)	H49B—C49—H49C	109.5
C25—C24—C23	117.2 (2)	C46—C50—H50A	109.5
C14—C24—C23	121.3 (2)	C46—C50—H50B	109.5
C24—C25—C17	120.7 (2)	H50A—C50—H50B	109.5
C24—C25—C26	125.5 (2)	C46—C50—H50C	109.5
C17—C25—C26	108.8 (2)	H50A—C50—H50C	109.5
C35—C26—C27	111.3 (2)	H50B—C50—H50C	109.5
C35—C26—C25	109.1 (2)	C53ⁱⁱ—C51—C52	117.5 (3)
C27—C26—C25	100.50 (19)	C53ⁱⁱ—C51—C54	121.8 (3)
C35—C26—C41	111.8 (2)	C52—C51—C54	120.7 (3)
C27—C26—C41	110.2 (2)	C53—C52—C51	120.7 (3)
C25—C26—C41	113.6 (2)	C53—C52—H52	119.7
C28—C27—C7ⁱ	119.7 (2)	C51—C52—H52	119.7
C28—C27—C26	123.6 (2)	C51ⁱⁱ—C53—C52	121.8 (3)
C7ⁱ—C27—C26	110.2 (2)	C51ⁱⁱ—C53—H53	119.1
C27—C28—C18ⁱ	119.4 (2)	C52—C53—H53	119.1
C27—C28—C29	123.5 (2)	C51—C54—H54A	109.5
C18ⁱ—C28—C29	110.1 (2)	C51—C54—H54B	109.5
C30—C29—C28	111.4 (2)	H54A—C54—H54B	109.5
C30—C29—C42	110.7 (2)	C51—C54—H54C	109.5
C28—C29—C42	110.9 (2)	H54A—C54—H54C	109.5
C30—C29—C31ⁱ	109.0 (2)	H54B—C54—H54C	109.5
C28—C29—C31ⁱ	100.51 (19)

Symmetry codes: (i) −x, y, −z+3/2; (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₈₄F₄₂·3C₈H₁₀
M_r	2125.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	25.4423 (16), 14.1495 (7), 22.6519 (11)
β (°)	107.070 (5)
V (Å³)	7795.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.40 × 0.23 × 0.09

Data collection
Diffractometer	Bruker Kappa APEX II
Absorption correction	Multi-scan (SADABS, Bruker, 2000)
T_min, T_max	0.933, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	130931, 9305, 6651
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.161, 1.04
No. of reflections	9305
No. of parameters	679
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0719P)² + 26.7468P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.53

Computer programs: APEX2 (Bruker, 2005), SHELXTL (Bruker, 2000).

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1,4,7,11,18,21,24,31,35,39,51,58,61,64-Tetra­deca­kis(trifluoro­meth­yl)-1,4,7,11,18,21,24,31,35,39,51,58,61,64-tetra­deca­hydro­(C70–D5h)[5,6]fullerene p-xylene tris­olvate

Supporting information

Key indicators

checkCIF/PLATON results

1,4,7,11,18,21,24,31,35,39,51,58,61,64-Tetradecakis(trifluoromethyl)-1,4,7,11,18,21,24,31,35,39,51,58,61,64-tetradecahydro(C₇₀–D_5h)[5,6]fullerene p-xylene trisolvate