1,7,16,30,36,47-Hexakis(perfluoro­isoprop­yl)-1,7,16,30,36,47-hexa­hydro­(C60–Ih)[5,6]fullerene

Shustova, N.B.; Kuvychko, I.V.; Boltalina, O.V.; Strauss, S.H.

doi:10.1107/S1600536807053895

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1,7,16,30,36,47-Hexakis(perfluoroisopropyl)-1,7,16,30,36,47-hexahydro(C₆₀–I_h)[5,6]fullerene

N. B. Shustova, I. V. Kuvychko, O. V. Boltalina and S. H. Strauss

The title compound, C₇₈F₄₂, is the first example of a perfluoroalkylfullerene with perfluoroisopropyl groups. The C₁ symmetry molecule has idealized C₃ symmetry with the six isopropyl groups arranged on three isolated para-C₆(i-C₃F₇)₂ hexagons. There are three intramolecular F

F contacts between pairs of isopropyl groups that share the same hexagon; these contacts range from 2.616 (3) to 2.657 (3) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053895/om2171sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053895/om2171Isup2.hkl Contains datablock I

CCDC reference: 672844

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R factor = 0.052
wR factor = 0.133
Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound ..          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      65.00 A   3 

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:C78 F42
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C16    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C30    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C36    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C47    = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Fullerenes with CF₃ or C₂F₅ groups generally have addition patterns that are ribbons of edge-sharing meta- and/or para-C₆(R_f)₂ hexagons (Popov et al., 2007a; Popov et al., 2007b; Tamm and Troyanov, 2007; Kareev, Kuvychko et al., 2006). The i-C₃F₇ group was chosen to destabilize sterically such ribbons relative to addition patterns with multiple isolated p-C₆(R_f)₂ hexagons so that fullerene(X)_n compounds with unprecedented addition patterns could be prepared and investigated.

The structure of the title compound, shown in Figure 1, consists of an icosahedral C₆₀ cage and three isolated p-C₆(i-C₃F₇)₂ hexagons arranged so that the C₆₀(i-C₃F₇)₆ molecule has idealized C₃ symmetry (but the molecule has no crystallographically imposed symmetry). The conformations of the perfluoroalkyl groups result in the fluoromethine F atoms positioned over the shared hexagon, as shown in Figure 2. The three F···F distances range from 2.616 (3) to 2.657 (3) Å and the three F—C···C—F torsion angles range from 51.9 (3) to 56.4 (3) degrees. In contrast, the F···F distance and F—C···C—F torsion angle for the isolated p-C₆(CF₃)₂ hexagon in 1,6,11,18,24,27,52,55-C₆₀(CF₃)₈ are 2.695 (3) Å and 3.4 (2) degrees, respectively (Kareev, Shustova et al., 2006). The differences are due in part to the different lengths of fluoromethine C—F bonds (these range from 1.372 (4) to 1.378 (4) in C₆₀(i-C₃F₇)₆) and trifluoromethyl C—F bonds (these range from 1.304 (3) to 1.347 (3) Å, and average 1.328 (1) Å, in 1,6,11,18,24,27,52,55-C₆₀(CF₃)₈) and range from 1.318 (4) to 1.353 (4) Å, and average 1.333 (1) Å, in C₆₀(i-C₃F₇)₆).

There are now more than 40 X-ray structures of fullerene(CF₃)_n and fullerene(C₂F₅)_n compounds (Popov et al., 2007a; Popov et al., 2007b; Tamm & Troyanov, 2007; Kareev, Newell et al., 2006). The compound 1,7,16,36,46,49-C₆₀(C₂F₅)₆ is the only other fullerene(R_f)_n with three or more isolated p-C₆(R_f)₂ hexagons (Kareev, Kuvychko et al., 2006). The addition patterns of both compounds are very similar, as shown in the Schlegel diagrams in Figure 3. The continued study of fullerene(i-C₃F₇)_n compounds will no doubt lead to other unprecedented addition patterns.

Related literature top

For related literature, see: Kareev, Kuvychko et al. (2006); Kareev, Shustova et al. (2006); Popov et al. (2007a,b); Tamm & Troyanov (2007).

Experimental top

The synthesis of the title compound was carried out by heating C₆₀ and i-C₃F₇I in a sealed ampoule at 300–400 °C. Crystals of the HPLC-purified compound were grown by slow evaporation of a saturated toluene solution.

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

	Fig. 1. The molecular structure of 1,7,16,30,36,47-C₆₀(i-C₃F₇)₆. Displacement ellipsoids are shown at the 50% probability level. The non-crystallographic C₃ axis is perpendicular to the plane of the page.
	Fig. 2. A portion of the structure of 1,7,16,30,36,47-C₆₀(i-C₃F₇)₆ showing one of the three para-C₆(C₆(i-C₃F₇)₂ hexagons. The F611···F641 distance is 2.653 (3) Å and the F611—C61···C64—F641 torsion angle is 56.4 (3) degrees.
	Fig. 3. (Left) Schlegel diagram of 1,7,16,30,36,47-C₆₀(i-C₃F₇)₆ showing the IUPAC lowest-locants for the cage carbon atoms to which the i-C₃F₇ groups are attached. The small triangle in the center denotes the molecular C₃ axis. (Right) Schlegel diagram of 1,7,16,36,46,49-C₆₀(C₂F₅)₆ showing the IUPAC lowest-locants for the cage carbon atoms to which the C₂F₅ groups are attached.

1,7,16,30,36,47-Hexakis(perfluoroisopropyl)- 1,7,16,30,36,47-hexahydro(C₆₀–I_h)[5,6]fullerene top

Crystal data top

C₇₈F₄₂	F(000) = 3384
M_r = 1734.78	D_x = 2.071 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.5877 (3) Å	Cell parameters from 9868 reflections
b = 31.1809 (7) Å	θ = 2.3–26.4°
c = 13.7240 (3) Å	µ = 0.22 mm⁻¹
β = 106.873 (1)°	T = 100 K
V = 5564.2 (2) Å³	Plate, red
Z = 4	0.30 × 0.11 × 0.06 mm

Data collection top

Bruker Kappa APEX II diffractometer	11386 independent reflections
Radiation source: fine-focus sealed tube	6862 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
Detector resolution: 0 pixels mm^-1	θ_max = 26.4°, θ_min = 1.7°
ϕ and ω scans	h = −16→16
Absorption correction: multi-scan SADABS (Sheldrick, 2003)	k = −30→38
T_min = 0.937, T_max = 0.988	l = −17→17
75325 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.052	Secondary atom site location: difference Fourier map
wR(F²) = 0.133	w = 1/[σ²(F_o²) + (0.0558P)² + 5.908P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
11386 reflections	Δρ_max = 0.53 e Å⁻³
1081 parameters	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₇₈F₄₂	V = 5564.2 (2) Å³
M_r = 1734.78	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.5877 (3) Å	µ = 0.22 mm⁻¹
b = 31.1809 (7) Å	T = 100 K
c = 13.7240 (3) Å	0.30 × 0.11 × 0.06 mm
β = 106.873 (1)°

Data collection top

Bruker Kappa APEX II diffractometer	11386 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 2003)	6862 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.988	R_int = 0.083
75325 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1081 parameters
wR(F²) = 0.133	0 restraints
S = 1.01	Δρ_max = 0.53 e Å⁻³
11386 reflections	Δρ_min = −0.32 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	0.6333 (3)	0.09622 (11)	0.3518 (3)	0.0163 (8)
C2	0.5209 (3)	0.08797 (11)	0.3546 (2)	0.0144 (7)
C3	0.4709 (3)	0.05947 (11)	0.2768 (3)	0.0160 (8)
C4	0.5354 (3)	0.05404 (11)	0.2077 (3)	0.0169 (8)
C5	0.6268 (2)	0.07914 (11)	0.2442 (3)	0.0150 (7)
C6	0.6666 (2)	0.10025 (11)	0.1759 (3)	0.0147 (7)
C7	0.7238 (2)	0.14363 (11)	0.1977 (3)	0.0150 (7)
C8	0.6891 (2)	0.16512 (11)	0.2821 (3)	0.0178 (8)
C9	0.6495 (2)	0.14421 (11)	0.3495 (2)	0.0158 (8)
C10	0.5857 (3)	0.17500 (11)	0.3876 (3)	0.0180 (8)
C11	0.4969 (3)	0.16276 (11)	0.4074 (2)	0.0175 (8)
C12	0.4641 (3)	0.11791 (11)	0.3891 (2)	0.0149 (7)
C13	0.3558 (3)	0.11734 (11)	0.3545 (2)	0.0163 (8)
C14	0.3077 (3)	0.08904 (11)	0.2773 (3)	0.0157 (8)
C15	0.3641 (3)	0.05823 (11)	0.2413 (2)	0.0159 (8)
C16	0.3059 (3)	0.04325 (11)	0.1323 (3)	0.0163 (8)
C17	0.3756 (3)	0.04820 (10)	0.0645 (3)	0.0145 (7)
C18	0.4894 (3)	0.04859 (11)	0.1061 (3)	0.0174 (8)
C19	0.5305 (3)	0.06950 (11)	0.0348 (3)	0.0151 (7)
C20	0.6163 (2)	0.09619 (11)	0.0695 (3)	0.0134 (7)
C21	0.6188 (2)	0.13636 (11)	0.0195 (3)	0.0154 (8)
C22	0.6725 (3)	0.16713 (12)	0.0947 (3)	0.0193 (8)
C23	0.6362 (3)	0.20845 (12)	0.0888 (3)	0.0199 (8)
C24	0.6283 (3)	0.23087 (11)	0.1806 (3)	0.0188 (8)
C25	0.6531 (2)	0.20971 (11)	0.2729 (3)	0.0168 (8)
C26	0.5899 (3)	0.21553 (11)	0.3394 (3)	0.0161 (7)
C27	0.5024 (3)	0.24146 (11)	0.3119 (3)	0.0163 (8)
C28	0.4110 (2)	0.22896 (11)	0.3369 (3)	0.0153 (7)
C29	0.4088 (3)	0.19032 (11)	0.3833 (2)	0.0163 (8)
C30	0.3112 (3)	0.16225 (11)	0.3666 (3)	0.0171 (8)
C31	0.2378 (2)	0.17523 (11)	0.2647 (2)	0.0138 (7)
C32	0.1883 (3)	0.14339 (11)	0.1858 (3)	0.0173 (8)
C33	0.2200 (2)	0.10183 (11)	0.1909 (3)	0.0161 (8)
C34	0.2238 (3)	0.07873 (11)	0.1017 (3)	0.0172 (8)
C35	0.1972 (2)	0.09910 (11)	0.0083 (3)	0.0167 (8)
C36	0.2458 (3)	0.08928 (11)	−0.0779 (2)	0.0156 (7)
C37	0.3495 (3)	0.06796 (11)	−0.0272 (3)	0.0150 (7)
C38	0.4439 (2)	0.08247 (11)	−0.0490 (2)	0.0147 (7)
C39	0.4465 (3)	0.12087 (11)	−0.0974 (2)	0.0156 (7)
C40	0.5349 (3)	0.14857 (12)	−0.0627 (3)	0.0195 (8)
C41	0.4995 (3)	0.19229 (12)	−0.0699 (3)	0.0187 (8)
C42	0.5499 (3)	0.22147 (11)	0.0046 (3)	0.0197 (8)
C43	0.4903 (3)	0.25257 (11)	0.0435 (3)	0.0207 (8)
C44	0.5381 (3)	0.25804 (11)	0.1508 (3)	0.0204 (8)
C45	0.4762 (3)	0.26333 (11)	0.2159 (3)	0.0184 (8)
C46	0.3656 (3)	0.26451 (11)	0.1767 (3)	0.0173 (8)
C47	0.3162 (3)	0.24977 (11)	0.2598 (3)	0.0155 (7)
C48	0.2406 (2)	0.21367 (11)	0.2182 (3)	0.0140 (7)
C49	0.1927 (2)	0.20879 (11)	0.1084 (3)	0.0146 (7)
C50	0.1596 (2)	0.16488 (11)	0.0896 (3)	0.0150 (7)
C51	0.1673 (2)	0.14345 (11)	0.0031 (3)	0.0157 (8)
C52	0.2074 (3)	0.16566 (12)	−0.0691 (3)	0.0184 (8)
C53	0.2647 (3)	0.13527 (11)	−0.1106 (2)	0.0185 (8)
C54	0.3546 (3)	0.14835 (12)	−0.1266 (2)	0.0189 (8)
C55	0.3890 (3)	0.19262 (11)	−0.1083 (2)	0.0170 (8)
C56	0.3325 (3)	0.22183 (11)	−0.0711 (3)	0.0179 (8)
C57	0.3840 (3)	0.25256 (11)	0.0060 (3)	0.0207 (8)
C58	0.3209 (3)	0.25820 (11)	0.0750 (3)	0.0211 (8)
C59	0.2307 (2)	0.23014 (11)	0.0393 (3)	0.0163 (8)
C60	0.2390 (3)	0.20813 (12)	−0.0511 (3)	0.0191 (8)
C61	0.7163 (3)	0.07237 (12)	0.4393 (3)	0.0211 (8)
C62	0.7457 (3)	0.09788 (13)	0.5399 (3)	0.0258 (9)
C63	0.6866 (3)	0.02601 (13)	0.4587 (3)	0.0259 (9)
C64	0.8445 (3)	0.14036 (12)	0.2256 (3)	0.0198 (8)
C65	0.8817 (3)	0.10239 (12)	0.1730 (3)	0.0231 (9)
C66	0.8961 (3)	0.18259 (13)	0.2059 (3)	0.0254 (9)
C71	0.2632 (3)	−0.00448 (12)	0.1279 (3)	0.0217 (8)
C72	0.3421 (3)	−0.03605 (11)	0.1916 (3)	0.0226 (8)
C73	0.1612 (3)	−0.00728 (13)	0.1544 (3)	0.0285 (9)
C74	0.1741 (3)	0.06129 (12)	−0.1656 (3)	0.0195 (8)
C75	0.0790 (3)	0.08585 (13)	−0.2320 (3)	0.0247 (9)
C76	0.2324 (3)	0.04054 (13)	−0.2341 (3)	0.0248 (9)
C81	0.2564 (3)	0.16416 (12)	0.4551 (3)	0.0216 (8)
C82	0.1908 (3)	0.12459 (12)	0.4584 (3)	0.0225 (9)
C83	0.3326 (3)	0.17322 (13)	0.5605 (3)	0.0294 (10)
C84	0.2669 (3)	0.28753 (11)	0.3065 (3)	0.0181 (8)
C85	0.3356 (3)	0.32729 (11)	0.3346 (3)	0.0212 (8)
C86	0.1592 (3)	0.29994 (11)	0.2378 (3)	0.0209 (8)
F611	0.80470 (15)	0.06890 (7)	0.41034 (16)	0.0287 (5)
F621	0.80504 (17)	0.07521 (7)	0.61711 (16)	0.0321 (5)
F622	0.66226 (16)	0.10955 (7)	0.56547 (15)	0.0297 (5)
F623	0.79801 (17)	0.13319 (7)	0.53091 (16)	0.0346 (6)
F631	0.76810 (18)	0.00455 (7)	0.51475 (17)	0.0362 (6)
F632	0.64986 (17)	0.00433 (7)	0.37240 (16)	0.0279 (5)
F633	0.61469 (17)	0.02545 (7)	0.50738 (16)	0.0311 (5)
F641	0.88280 (14)	0.13275 (7)	0.32809 (15)	0.0260 (5)
F651	0.98236 (15)	0.10383 (7)	0.18588 (17)	0.0319 (5)
F652	0.83554 (15)	0.10227 (7)	0.07281 (16)	0.0285 (5)
F653	0.86110 (15)	0.06529 (7)	0.21100 (17)	0.0292 (5)
F661	0.99620 (15)	0.18263 (7)	0.25622 (18)	0.0338 (6)
F662	0.85483 (16)	0.21631 (7)	0.23915 (18)	0.0337 (6)
F663	0.88577 (16)	0.18792 (7)	0.10707 (17)	0.0329 (6)
F711	0.24276 (17)	−0.01883 (7)	0.02927 (15)	0.0283 (5)
F721	0.31623 (18)	−0.07650 (7)	0.16486 (18)	0.0360 (6)
F722	0.34970 (18)	−0.03225 (7)	0.29069 (16)	0.0329 (6)
F723	0.43549 (16)	−0.02996 (7)	0.18104 (17)	0.0293 (5)
F731	0.13276 (18)	−0.04834 (7)	0.15836 (18)	0.0378 (6)
F732	0.08582 (16)	0.01214 (8)	0.08282 (19)	0.0375 (6)
F733	0.16705 (17)	0.01098 (7)	0.24359 (18)	0.0346 (6)
F741	0.13473 (16)	0.02827 (6)	−0.12255 (15)	0.0256 (5)
F751	0.01111 (16)	0.05892 (8)	−0.29029 (17)	0.0379 (6)
F752	0.10518 (17)	0.11463 (8)	−0.29092 (17)	0.0387 (6)
F753	0.03068 (15)	0.10617 (7)	−0.17345 (16)	0.0321 (6)
F761	0.16948 (16)	0.02142 (8)	−0.31524 (16)	0.0341 (6)
F762	0.29605 (17)	0.01033 (7)	−0.18262 (17)	0.0339 (6)
F763	0.28763 (17)	0.06945 (7)	−0.26690 (16)	0.0328 (6)
F811	0.18824 (16)	0.19794 (7)	0.43554 (16)	0.0280 (5)
F821	0.12408 (18)	0.13216 (8)	0.51088 (18)	0.0393 (6)
F822	0.25071 (18)	0.09149 (7)	0.50469 (17)	0.0365 (6)
F823	0.13816 (16)	0.11148 (7)	0.36677 (16)	0.0303 (5)
F831	0.28580 (18)	0.17033 (8)	0.63388 (16)	0.0405 (6)
F832	0.36870 (18)	0.21329 (8)	0.56370 (17)	0.0373 (6)
F833	0.41085 (17)	0.14643 (8)	0.58299 (16)	0.0351 (6)
F841	0.25277 (15)	0.27327 (6)	0.39657 (15)	0.0236 (5)
F851	0.30260 (16)	0.35327 (7)	0.39559 (16)	0.0300 (5)
F852	0.33652 (16)	0.34939 (6)	0.25144 (16)	0.0283 (5)
F853	0.43237 (15)	0.31704 (6)	0.38514 (16)	0.0261 (5)
F861	0.09038 (15)	0.26999 (7)	0.24179 (17)	0.0275 (5)
F862	0.15848 (16)	0.30427 (7)	0.14115 (15)	0.0259 (5)
F863	0.12588 (16)	0.33685 (6)	0.26575 (16)	0.0269 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0123 (17)	0.0181 (19)	0.0184 (19)	0.0023 (15)	0.0042 (15)	0.0041 (15)
C2	0.0154 (18)	0.0159 (19)	0.0111 (17)	0.0027 (15)	0.0024 (15)	0.0079 (14)
C3	0.0239 (19)	0.0095 (18)	0.0160 (18)	0.0009 (15)	0.0081 (16)	0.0061 (14)
C4	0.0181 (19)	0.0107 (18)	0.0206 (19)	0.0038 (15)	0.0036 (16)	0.0026 (15)
C5	0.0118 (17)	0.0135 (18)	0.0178 (18)	0.0064 (14)	0.0013 (15)	−0.0005 (15)
C6	0.0079 (16)	0.0154 (19)	0.0203 (19)	0.0053 (14)	0.0034 (15)	−0.0027 (15)
C7	0.0106 (17)	0.0156 (19)	0.0193 (18)	−0.0003 (14)	0.0050 (15)	0.0003 (15)
C8	0.0086 (17)	0.022 (2)	0.0202 (19)	−0.0038 (15)	−0.0005 (15)	−0.0040 (16)
C9	0.0100 (17)	0.023 (2)	0.0100 (17)	0.0020 (15)	−0.0034 (14)	−0.0027 (15)
C10	0.0158 (18)	0.022 (2)	0.0115 (17)	−0.0016 (15)	−0.0034 (15)	−0.0048 (15)
C11	0.023 (2)	0.019 (2)	0.0083 (17)	−0.0006 (16)	0.0013 (15)	−0.0017 (14)
C12	0.0195 (18)	0.0172 (19)	0.0066 (16)	−0.0018 (15)	0.0014 (14)	0.0013 (14)
C13	0.0220 (19)	0.0176 (19)	0.0129 (17)	0.0055 (15)	0.0107 (16)	0.0062 (15)
C14	0.0124 (17)	0.0183 (19)	0.0172 (18)	−0.0022 (15)	0.0056 (15)	0.0041 (15)
C15	0.023 (2)	0.0115 (18)	0.0119 (17)	−0.0058 (15)	0.0041 (15)	0.0024 (14)
C16	0.0168 (18)	0.0145 (19)	0.0167 (18)	−0.0056 (15)	0.0036 (15)	−0.0005 (15)
C17	0.0170 (18)	0.0079 (18)	0.0155 (18)	−0.0011 (14)	−0.0001 (15)	−0.0046 (14)
C18	0.0208 (19)	0.0123 (18)	0.0205 (19)	0.0053 (15)	0.0081 (16)	−0.0024 (15)
C19	0.0173 (18)	0.0153 (19)	0.0157 (18)	0.0026 (15)	0.0093 (15)	−0.0031 (15)
C20	0.0090 (16)	0.0149 (19)	0.0189 (18)	0.0030 (14)	0.0081 (15)	−0.0034 (15)
C21	0.0127 (17)	0.0175 (19)	0.0189 (19)	0.0000 (14)	0.0093 (16)	−0.0021 (15)
C22	0.0129 (18)	0.024 (2)	0.025 (2)	−0.0013 (16)	0.0110 (16)	0.0054 (16)
C23	0.0145 (18)	0.020 (2)	0.029 (2)	−0.0098 (16)	0.0122 (17)	0.0005 (16)
C24	0.0181 (19)	0.020 (2)	0.0216 (19)	−0.0114 (16)	0.0101 (16)	−0.0083 (16)
C25	0.0086 (17)	0.0142 (19)	0.026 (2)	−0.0047 (14)	0.0033 (15)	−0.0061 (16)
C26	0.0147 (18)	0.0172 (19)	0.0146 (18)	−0.0059 (15)	0.0013 (15)	−0.0045 (15)
C27	0.0188 (19)	0.0124 (18)	0.0172 (18)	−0.0014 (15)	0.0043 (15)	−0.0075 (15)
C28	0.0143 (18)	0.0137 (18)	0.0178 (18)	−0.0010 (14)	0.0045 (15)	−0.0076 (15)
C29	0.0211 (19)	0.0179 (19)	0.0094 (17)	0.0023 (15)	0.0038 (15)	−0.0048 (14)
C30	0.0214 (19)	0.0173 (19)	0.0137 (18)	0.0006 (15)	0.0068 (16)	0.0003 (15)
C31	0.0101 (17)	0.0191 (19)	0.0156 (17)	0.0009 (14)	0.0091 (15)	−0.0009 (15)
C32	0.0123 (18)	0.019 (2)	0.025 (2)	−0.0022 (15)	0.0118 (16)	−0.0007 (16)
C33	0.0118 (17)	0.020 (2)	0.0177 (18)	−0.0048 (15)	0.0062 (15)	0.0000 (15)
C34	0.0111 (17)	0.022 (2)	0.0186 (19)	−0.0094 (15)	0.0046 (15)	−0.0057 (15)
C35	0.0053 (16)	0.025 (2)	0.0175 (18)	−0.0021 (15)	−0.0004 (14)	−0.0049 (16)
C36	0.0158 (18)	0.0184 (19)	0.0103 (17)	0.0018 (15)	0.0001 (15)	−0.0031 (14)
C37	0.0146 (17)	0.0142 (18)	0.0150 (18)	−0.0017 (15)	0.0022 (15)	−0.0069 (15)
C38	0.0154 (18)	0.0157 (19)	0.0137 (17)	0.0006 (15)	0.0051 (15)	−0.0082 (14)
C39	0.0198 (19)	0.021 (2)	0.0064 (16)	0.0041 (16)	0.0044 (15)	0.0016 (14)
C40	0.024 (2)	0.024 (2)	0.0154 (18)	0.0025 (17)	0.0135 (16)	0.0016 (16)
C41	0.021 (2)	0.022 (2)	0.0162 (19)	0.0017 (16)	0.0115 (16)	0.0084 (16)
C42	0.0202 (19)	0.021 (2)	0.022 (2)	−0.0029 (16)	0.0120 (17)	0.0074 (16)
C43	0.031 (2)	0.0118 (19)	0.0204 (19)	−0.0043 (16)	0.0095 (17)	0.0041 (15)
C44	0.026 (2)	0.0093 (19)	0.025 (2)	−0.0050 (16)	0.0061 (17)	0.0026 (15)
C45	0.0211 (19)	0.0087 (18)	0.023 (2)	−0.0020 (15)	0.0029 (16)	−0.0043 (15)
C46	0.024 (2)	0.0072 (18)	0.023 (2)	0.0025 (15)	0.0107 (17)	−0.0003 (15)
C47	0.0211 (19)	0.0120 (18)	0.0151 (18)	0.0007 (15)	0.0077 (16)	−0.0013 (14)
C48	0.0126 (17)	0.0131 (18)	0.0178 (18)	0.0022 (14)	0.0070 (15)	−0.0034 (15)
C49	0.0097 (17)	0.0147 (19)	0.0193 (18)	0.0053 (14)	0.0038 (15)	0.0000 (15)
C50	0.0074 (16)	0.021 (2)	0.0165 (18)	0.0023 (15)	0.0032 (14)	−0.0002 (15)
C51	0.0054 (16)	0.022 (2)	0.0154 (18)	0.0025 (14)	−0.0030 (14)	−0.0027 (15)
C52	0.0147 (18)	0.024 (2)	0.0130 (18)	0.0082 (16)	−0.0016 (15)	0.0008 (15)
C53	0.023 (2)	0.023 (2)	0.0067 (17)	0.0010 (16)	−0.0007 (15)	−0.0005 (15)
C54	0.026 (2)	0.026 (2)	0.0050 (16)	0.0059 (17)	0.0046 (15)	0.0024 (15)
C55	0.023 (2)	0.018 (2)	0.0106 (17)	0.0008 (15)	0.0066 (16)	0.0055 (15)
C56	0.0178 (18)	0.022 (2)	0.0140 (18)	0.0077 (16)	0.0048 (15)	0.0105 (15)
C57	0.030 (2)	0.0150 (19)	0.0194 (19)	0.0047 (16)	0.0108 (17)	0.0090 (16)
C58	0.025 (2)	0.0132 (19)	0.026 (2)	0.0069 (16)	0.0097 (18)	0.0087 (16)
C59	0.0111 (17)	0.0121 (18)	0.0239 (19)	0.0076 (14)	0.0021 (15)	0.0063 (15)
C60	0.0173 (18)	0.024 (2)	0.0144 (18)	0.0109 (16)	0.0025 (15)	0.0097 (16)
C61	0.0183 (19)	0.024 (2)	0.021 (2)	0.0029 (16)	0.0063 (16)	0.0005 (16)
C62	0.026 (2)	0.027 (2)	0.020 (2)	0.0042 (18)	−0.0018 (18)	0.0036 (17)
C63	0.029 (2)	0.029 (2)	0.017 (2)	0.0105 (18)	0.0011 (18)	0.0007 (17)
C64	0.0115 (18)	0.025 (2)	0.022 (2)	−0.0018 (16)	0.0027 (16)	0.0006 (16)
C65	0.0127 (19)	0.025 (2)	0.031 (2)	−0.0003 (16)	0.0068 (17)	0.0008 (18)
C66	0.0089 (19)	0.027 (2)	0.039 (2)	−0.0003 (16)	0.0058 (18)	−0.0075 (19)
C71	0.025 (2)	0.020 (2)	0.0181 (19)	−0.0074 (16)	0.0038 (17)	−0.0041 (16)
C72	0.029 (2)	0.0117 (19)	0.028 (2)	−0.0050 (16)	0.0106 (18)	−0.0009 (16)
C73	0.030 (2)	0.021 (2)	0.033 (2)	−0.0079 (18)	0.007 (2)	−0.0022 (18)
C74	0.0164 (18)	0.024 (2)	0.0154 (18)	−0.0002 (16)	−0.0002 (16)	−0.0021 (16)
C75	0.020 (2)	0.033 (2)	0.0170 (19)	0.0010 (18)	−0.0022 (17)	−0.0077 (18)
C76	0.019 (2)	0.034 (2)	0.018 (2)	−0.0015 (18)	−0.0007 (17)	−0.0109 (18)
C81	0.025 (2)	0.021 (2)	0.021 (2)	0.0051 (17)	0.0096 (17)	0.0022 (16)
C82	0.025 (2)	0.028 (2)	0.019 (2)	−0.0026 (18)	0.0130 (18)	−0.0038 (17)
C83	0.036 (2)	0.032 (3)	0.022 (2)	−0.004 (2)	0.0126 (19)	0.0003 (18)
C84	0.0216 (19)	0.018 (2)	0.0172 (18)	0.0021 (15)	0.0092 (16)	0.0009 (15)
C85	0.023 (2)	0.016 (2)	0.024 (2)	0.0028 (16)	0.0066 (17)	−0.0043 (16)
C86	0.024 (2)	0.016 (2)	0.025 (2)	−0.0002 (16)	0.0099 (17)	−0.0039 (16)
F611	0.0200 (11)	0.0358 (13)	0.0301 (12)	0.0073 (10)	0.0070 (10)	0.0060 (10)
F621	0.0306 (12)	0.0367 (14)	0.0209 (12)	0.0071 (11)	−0.0052 (10)	0.0043 (10)
F622	0.0281 (12)	0.0372 (14)	0.0202 (11)	0.0071 (10)	0.0015 (10)	−0.0026 (10)
F623	0.0331 (13)	0.0341 (14)	0.0276 (13)	−0.0109 (11)	−0.0053 (11)	−0.0001 (11)
F631	0.0420 (14)	0.0280 (13)	0.0315 (13)	0.0137 (11)	−0.0007 (12)	0.0081 (11)
F632	0.0371 (13)	0.0205 (12)	0.0243 (12)	0.0041 (10)	0.0058 (11)	0.0012 (10)
F633	0.0400 (13)	0.0303 (13)	0.0266 (12)	0.0004 (11)	0.0154 (11)	0.0053 (10)
F641	0.0146 (11)	0.0383 (14)	0.0222 (12)	0.0002 (9)	0.0008 (9)	−0.0003 (10)
F651	0.0132 (11)	0.0373 (14)	0.0467 (14)	−0.0006 (10)	0.0109 (10)	−0.0078 (11)
F652	0.0221 (11)	0.0363 (14)	0.0283 (13)	0.0009 (10)	0.0092 (10)	−0.0067 (10)
F653	0.0250 (12)	0.0197 (12)	0.0454 (14)	0.0039 (9)	0.0143 (11)	0.0034 (10)
F661	0.0159 (12)	0.0328 (14)	0.0525 (15)	−0.0077 (10)	0.0094 (11)	−0.0083 (11)
F662	0.0245 (12)	0.0230 (12)	0.0571 (16)	−0.0053 (10)	0.0173 (12)	−0.0102 (11)
F663	0.0309 (13)	0.0344 (14)	0.0383 (14)	−0.0074 (10)	0.0175 (11)	0.0049 (11)
F711	0.0371 (13)	0.0231 (12)	0.0223 (12)	−0.0101 (10)	0.0048 (10)	−0.0059 (9)
F721	0.0432 (14)	0.0156 (12)	0.0469 (15)	−0.0046 (10)	0.0093 (12)	0.0005 (11)
F722	0.0432 (14)	0.0337 (14)	0.0220 (12)	−0.0040 (11)	0.0099 (11)	0.0048 (10)
F723	0.0272 (12)	0.0241 (13)	0.0391 (14)	0.0030 (10)	0.0134 (11)	0.0051 (10)
F731	0.0400 (14)	0.0268 (14)	0.0492 (15)	−0.0157 (11)	0.0171 (12)	−0.0023 (11)
F732	0.0197 (12)	0.0390 (15)	0.0492 (15)	−0.0056 (11)	0.0027 (12)	0.0031 (12)
F733	0.0382 (14)	0.0336 (14)	0.0397 (14)	−0.0110 (11)	0.0236 (12)	−0.0079 (11)
F741	0.0287 (12)	0.0251 (12)	0.0215 (11)	−0.0066 (10)	0.0049 (10)	−0.0028 (9)
F751	0.0223 (12)	0.0489 (16)	0.0317 (13)	0.0044 (11)	−0.0090 (11)	−0.0186 (12)
F752	0.0363 (14)	0.0479 (16)	0.0265 (13)	0.0073 (12)	0.0005 (11)	0.0132 (12)
F753	0.0176 (11)	0.0456 (15)	0.0285 (13)	0.0083 (10)	−0.0006 (10)	−0.0128 (11)
F761	0.0277 (12)	0.0466 (15)	0.0239 (12)	−0.0016 (11)	0.0011 (10)	−0.0193 (11)
F762	0.0309 (13)	0.0338 (14)	0.0301 (13)	0.0139 (11)	−0.0021 (11)	−0.0123 (11)
F763	0.0332 (13)	0.0409 (14)	0.0286 (13)	−0.0032 (11)	0.0157 (11)	−0.0089 (11)
F811	0.0349 (13)	0.0272 (13)	0.0270 (12)	0.0076 (10)	0.0170 (11)	0.0010 (10)
F821	0.0420 (14)	0.0488 (16)	0.0375 (14)	−0.0124 (12)	0.0278 (12)	−0.0071 (12)
F822	0.0494 (15)	0.0276 (13)	0.0347 (13)	−0.0008 (12)	0.0158 (12)	0.0092 (11)
F823	0.0294 (12)	0.0375 (14)	0.0265 (13)	−0.0118 (11)	0.0121 (10)	−0.0056 (10)
F831	0.0485 (15)	0.0584 (17)	0.0203 (12)	−0.0078 (13)	0.0192 (12)	−0.0047 (11)
F832	0.0469 (15)	0.0375 (15)	0.0315 (13)	−0.0169 (12)	0.0178 (12)	−0.0144 (11)
F833	0.0357 (14)	0.0480 (15)	0.0183 (12)	0.0052 (12)	0.0028 (11)	0.0016 (11)
F841	0.0324 (12)	0.0235 (12)	0.0191 (11)	0.0045 (10)	0.0139 (10)	0.0000 (9)
F851	0.0353 (13)	0.0197 (12)	0.0338 (13)	0.0046 (10)	0.0082 (11)	−0.0101 (10)
F852	0.0355 (13)	0.0193 (12)	0.0283 (12)	−0.0048 (10)	0.0066 (11)	0.0032 (10)
F853	0.0234 (12)	0.0198 (12)	0.0306 (12)	0.0013 (9)	0.0006 (10)	−0.0078 (10)
F861	0.0224 (11)	0.0235 (12)	0.0391 (13)	−0.0005 (9)	0.0128 (10)	−0.0019 (10)
F862	0.0289 (12)	0.0277 (13)	0.0211 (12)	0.0069 (10)	0.0073 (10)	−0.0001 (9)
F863	0.0280 (12)	0.0212 (12)	0.0322 (12)	0.0078 (10)	0.0100 (10)	−0.0058 (10)

Geometric parameters (Å, º) top

C1—C9	1.514 (5)	C44—C45	1.404 (5)
C1—C5	1.548 (5)	C45—C46	1.442 (5)
C1—C2	1.559 (4)	C46—C58	1.365 (5)
C1—C61	1.575 (5)	C46—C47	1.552 (5)
C2—C12	1.380 (5)	C47—C48	1.519 (5)
C2—C3	1.404 (5)	C47—C84	1.579 (5)
C3—C15	1.391 (5)	C48—C49	1.465 (5)
C3—C4	1.476 (5)	C49—C59	1.376 (5)
C4—C18	1.364 (5)	C49—C50	1.441 (5)
C4—C5	1.430 (5)	C50—C51	1.392 (5)
C5—C6	1.378 (5)	C51—C52	1.439 (5)
C6—C20	1.426 (5)	C52—C60	1.392 (5)
C6—C7	1.545 (5)	C52—C53	1.445 (5)
C7—C8	1.526 (5)	C53—C54	1.365 (5)
C7—C22	1.565 (5)	C54—C55	1.456 (5)
C7—C64	1.577 (5)	C55—C56	1.380 (5)
C8—C9	1.363 (5)	C56—C60	1.440 (5)
C8—C25	1.467 (5)	C56—C57	1.449 (5)
C9—C10	1.486 (5)	C57—C58	1.461 (5)
C10—C11	1.367 (5)	C58—C59	1.468 (5)
C10—C26	1.435 (5)	C59—C60	1.451 (5)
C11—C29	1.432 (5)	C61—F611	1.374 (4)
C11—C12	1.467 (5)	C61—C62	1.542 (5)
C12—C13	1.408 (5)	C61—C63	1.545 (5)
C13—C14	1.388 (5)	C62—F622	1.332 (4)
C13—C30	1.554 (5)	C62—F621	1.333 (4)
C14—C15	1.406 (5)	C62—F623	1.335 (4)
C14—C33	1.472 (5)	C63—F632	1.329 (4)
C15—C16	1.547 (5)	C63—F631	1.331 (4)
C16—C17	1.516 (5)	C63—F633	1.334 (4)
C16—C34	1.541 (5)	C64—F641	1.372 (4)
C16—C71	1.592 (5)	C64—C65	1.545 (5)
C17—C37	1.353 (5)	C64—C66	1.551 (5)
C17—C18	1.484 (5)	C65—F651	1.329 (4)
C18—C19	1.418 (5)	C65—F653	1.331 (4)
C19—C20	1.398 (5)	C65—F652	1.335 (4)
C19—C38	1.444 (5)	C66—F663	1.332 (4)
C20—C21	1.433 (5)	C66—F662	1.333 (4)
C21—C40	1.405 (5)	C66—F661	1.335 (4)
C21—C22	1.443 (5)	C71—F711	1.375 (4)
C22—C23	1.374 (5)	C71—C72	1.529 (5)
C23—C42	1.445 (5)	C71—C73	1.535 (5)
C23—C24	1.473 (5)	C72—F721	1.332 (4)
C24—C25	1.380 (5)	C72—F723	1.332 (4)
C24—C44	1.448 (5)	C72—F722	1.338 (4)
C25—C26	1.435 (4)	C73—F733	1.332 (4)
C26—C27	1.396 (5)	C73—F732	1.340 (5)
C27—C45	1.433 (5)	C73—F731	1.343 (4)
C27—C28	1.435 (5)	C74—F741	1.371 (4)
C28—C29	1.367 (5)	C74—C76	1.537 (5)
C28—C47	1.552 (5)	C74—C75	1.550 (5)
C29—C30	1.550 (5)	C75—F752	1.324 (4)
C30—C31	1.517 (5)	C75—F751	1.330 (4)
C30—C81	1.599 (5)	C75—F753	1.336 (4)
C31—C48	1.364 (5)	C76—F763	1.332 (4)
C31—C32	1.479 (5)	C76—F761	1.332 (4)
C32—C33	1.361 (5)	C76—F762	1.334 (4)
C32—C50	1.430 (5)	C81—F811	1.376 (4)
C33—C34	1.435 (5)	C81—C82	1.530 (5)
C34—C35	1.381 (5)	C81—C83	1.541 (5)
C35—C51	1.437 (5)	C82—F823	1.318 (4)
C35—C36	1.543 (4)	C82—F821	1.333 (4)
C36—C37	1.531 (5)	C82—F822	1.353 (4)
C36—C53	1.546 (5)	C83—F833	1.316 (5)
C36—C74	1.574 (5)	C83—F832	1.338 (5)
C37—C38	1.469 (4)	C83—F831	1.341 (4)
C38—C39	1.375 (5)	C84—F841	1.378 (4)
C39—C40	1.444 (5)	C84—C85	1.532 (5)
C39—C54	1.471 (5)	C84—C86	1.543 (5)
C40—C41	1.439 (5)	C85—F851	1.332 (4)
C41—C42	1.391 (5)	C85—F853	1.335 (4)
C41—C55	1.440 (5)	C85—F852	1.336 (4)
C42—C43	1.461 (5)	C86—F862	1.330 (4)
C43—C57	1.385 (5)	C86—F863	1.333 (4)
C43—C44	1.436 (5)	C86—F861	1.334 (4)

C9—C1—C5	106.8 (3)	C48—C47—C28	106.4 (3)
C9—C1—C2	108.2 (3)	C48—C47—C46	109.4 (3)
C5—C1—C2	100.5 (3)	C28—C47—C46	100.0 (3)
C9—C1—C61	114.0 (3)	C48—C47—C84	112.7 (3)
C5—C1—C61	113.2 (3)	C28—C47—C84	113.6 (3)
C2—C1—C61	113.1 (3)	C46—C47—C84	113.7 (3)
C12—C2—C3	119.6 (3)	C31—C48—C49	109.0 (3)
C12—C2—C1	123.1 (3)	C31—C48—C47	125.7 (3)
C3—C2—C1	110.3 (3)	C49—C48—C47	120.9 (3)
C15—C3—C2	120.7 (3)	C59—C49—C50	119.8 (3)
C15—C3—C4	121.7 (3)	C59—C49—C48	121.0 (3)
C2—C3—C4	108.3 (3)	C50—C49—C48	107.8 (3)
C18—C4—C5	121.3 (3)	C51—C50—C32	119.6 (3)
C18—C4—C3	119.3 (3)	C51—C50—C49	120.8 (3)
C5—C4—C3	109.3 (3)	C32—C50—C49	107.0 (3)
C6—C5—C4	119.7 (3)	C50—C51—C35	120.7 (3)
C6—C5—C1	124.1 (3)	C50—C51—C52	119.6 (3)
C4—C5—C1	109.0 (3)	C35—C51—C52	109.8 (3)
C5—C6—C20	119.2 (3)	C60—C52—C51	119.7 (3)
C5—C6—C7	124.1 (3)	C60—C52—C53	121.3 (3)
C20—C6—C7	109.9 (3)	C51—C52—C53	108.1 (3)
C8—C7—C6	106.5 (3)	C54—C53—C52	118.5 (3)
C8—C7—C22	109.0 (3)	C54—C53—C36	123.8 (3)
C6—C7—C22	99.7 (3)	C52—C53—C36	109.9 (3)
C8—C7—C64	111.9 (3)	C53—C54—C55	120.8 (3)
C6—C7—C64	114.8 (3)	C53—C54—C39	120.7 (3)
C22—C7—C64	114.1 (3)	C55—C54—C39	107.5 (3)
C9—C8—C25	108.9 (3)	C56—C55—C41	120.1 (3)
C9—C8—C7	125.1 (3)	C56—C55—C54	120.3 (3)
C25—C8—C7	121.3 (3)	C41—C55—C54	107.8 (3)
C8—C9—C10	108.3 (3)	C55—C56—C60	119.3 (3)
C8—C9—C1	125.1 (3)	C55—C56—C57	120.3 (3)
C10—C9—C1	121.9 (3)	C60—C56—C57	108.8 (3)
C11—C10—C26	119.5 (3)	C43—C57—C56	120.1 (3)
C11—C10—C9	121.9 (3)	C43—C57—C58	120.3 (3)
C26—C10—C9	107.6 (3)	C56—C57—C58	107.6 (3)
C10—C11—C29	120.9 (3)	C46—C58—C57	120.6 (3)
C10—C11—C12	118.3 (3)	C46—C58—C59	120.5 (3)
C29—C11—C12	109.9 (3)	C57—C58—C59	107.6 (3)
C2—C12—C13	120.7 (3)	C49—C59—C60	119.9 (3)
C2—C12—C11	122.1 (3)	C49—C59—C58	120.1 (3)
C13—C12—C11	107.8 (3)	C60—C59—C58	107.6 (3)
C14—C13—C12	118.7 (3)	C52—C60—C56	119.5 (3)
C14—C13—C30	122.8 (3)	C52—C60—C59	120.3 (3)
C12—C13—C30	110.8 (3)	C56—C60—C59	108.3 (3)
C13—C14—C15	121.2 (3)	F611—C61—C62	106.1 (3)
C13—C14—C33	122.4 (3)	F611—C61—C63	105.7 (3)
C15—C14—C33	107.4 (3)	C62—C61—C63	109.9 (3)
C3—C15—C14	118.5 (3)	F611—C61—C1	108.0 (3)
C3—C15—C16	122.4 (3)	C62—C61—C1	112.4 (3)
C14—C15—C16	111.6 (3)	C63—C61—C1	114.1 (3)
C17—C16—C34	107.0 (3)	F622—C62—F621	107.5 (3)
C17—C16—C15	109.1 (3)	F622—C62—F623	108.4 (3)
C34—C16—C15	100.0 (3)	F621—C62—F623	107.2 (3)
C17—C16—C71	111.0 (3)	F622—C62—C61	111.0 (3)
C34—C16—C71	115.7 (3)	F621—C62—C61	112.2 (3)
C15—C16—C71	113.4 (3)	F623—C62—C61	110.4 (3)
C37—C17—C18	108.4 (3)	F632—C63—F631	107.1 (3)
C37—C17—C16	125.1 (3)	F632—C63—F633	107.4 (3)
C18—C17—C16	122.1 (3)	F631—C63—F633	108.2 (3)
C4—C18—C19	119.5 (3)	F632—C63—C61	111.8 (3)
C4—C18—C17	120.8 (3)	F631—C63—C61	110.8 (3)
C19—C18—C17	108.3 (3)	F633—C63—C61	111.4 (3)
C20—C19—C18	119.7 (3)	F641—C64—C65	105.6 (3)
C20—C19—C38	120.7 (3)	F641—C64—C66	105.6 (3)
C18—C19—C38	106.5 (3)	C65—C64—C66	110.1 (3)
C19—C20—C6	120.4 (3)	F641—C64—C7	108.5 (3)
C19—C20—C21	119.4 (3)	C65—C64—C7	113.2 (3)
C6—C20—C21	109.9 (3)	C66—C64—C7	113.2 (3)
C40—C21—C20	119.6 (3)	F651—C65—F653	107.6 (3)
C40—C21—C22	121.2 (3)	F651—C65—F652	107.1 (3)
C20—C21—C22	108.4 (3)	F653—C65—F652	108.2 (3)
C23—C22—C21	118.9 (3)	F651—C65—C64	112.0 (3)
C23—C22—C7	123.5 (3)	F653—C65—C64	110.4 (3)
C21—C22—C7	109.6 (3)	F652—C65—C64	111.3 (3)
C22—C23—C42	120.4 (3)	F663—C66—F662	108.7 (3)
C22—C23—C24	120.5 (3)	F663—C66—F661	108.5 (3)
C42—C23—C24	107.9 (3)	F662—C66—F661	106.8 (3)
C25—C24—C44	120.0 (3)	F663—C66—C64	111.3 (3)
C25—C24—C23	120.0 (3)	F662—C66—C64	110.7 (3)
C44—C24—C23	107.6 (3)	F661—C66—C64	110.7 (3)
C24—C25—C26	119.4 (3)	F711—C71—C72	105.2 (3)
C24—C25—C8	121.2 (3)	F711—C71—C73	106.0 (3)
C26—C25—C8	108.1 (3)	C72—C71—C73	111.1 (3)
C27—C26—C10	119.4 (3)	F711—C71—C16	108.0 (3)
C27—C26—C25	121.4 (3)	C72—C71—C16	113.2 (3)
C10—C26—C25	107.0 (3)	C73—C71—C16	112.9 (3)
C26—C27—C45	119.4 (3)	F721—C72—F723	106.7 (3)
C26—C27—C28	120.4 (3)	F721—C72—F722	107.5 (3)
C45—C27—C28	110.3 (3)	F723—C72—F722	107.6 (3)
C29—C28—C27	119.2 (3)	F721—C72—C71	111.5 (3)
C29—C28—C47	124.1 (3)	F723—C72—C71	112.2 (3)
C27—C28—C47	109.2 (3)	F722—C72—C71	111.0 (3)
C28—C29—C11	120.5 (3)	F733—C73—F732	108.1 (3)
C28—C29—C30	124.2 (3)	F733—C73—F731	108.1 (3)
C11—C29—C30	108.5 (3)	F732—C73—F731	107.0 (3)
C31—C30—C29	106.9 (3)	F733—C73—C71	112.1 (3)
C31—C30—C13	108.4 (3)	F732—C73—C71	110.6 (3)
C29—C30—C13	100.4 (3)	F731—C73—C71	110.7 (3)
C31—C30—C81	111.3 (3)	F741—C74—C76	106.4 (3)
C29—C30—C81	115.7 (3)	F741—C74—C75	105.1 (3)
C13—C30—C81	113.4 (3)	C76—C74—C75	109.8 (3)
C48—C31—C32	108.4 (3)	F741—C74—C36	108.6 (3)
C48—C31—C30	124.4 (3)	C76—C74—C36	112.8 (3)
C32—C31—C30	122.2 (3)	C75—C74—C36	113.6 (3)
C33—C32—C50	119.4 (3)	F752—C75—F751	108.8 (3)
C33—C32—C31	122.1 (3)	F752—C75—F753	108.2 (3)
C50—C32—C31	107.8 (3)	F751—C75—F753	106.5 (3)
C32—C33—C34	121.6 (3)	F752—C75—C74	111.6 (3)
C32—C33—C14	118.0 (3)	F751—C75—C74	110.9 (3)
C34—C33—C14	109.3 (3)	F753—C75—C74	110.7 (3)
C35—C34—C33	119.8 (3)	F763—C76—F761	108.0 (3)
C35—C34—C16	123.8 (3)	F763—C76—F762	108.4 (3)
C33—C34—C16	109.3 (3)	F761—C76—F762	106.7 (3)
C34—C35—C51	118.8 (3)	F763—C76—C74	111.2 (3)
C34—C35—C36	124.4 (3)	F761—C76—C74	112.3 (3)
C51—C35—C36	109.3 (3)	F762—C76—C74	110.1 (3)
C37—C36—C35	106.2 (3)	F811—C81—C82	105.0 (3)
C37—C36—C53	109.0 (3)	F811—C81—C83	105.9 (3)
C35—C36—C53	100.5 (3)	C82—C81—C83	111.0 (3)
C37—C36—C74	113.0 (3)	F811—C81—C30	108.4 (3)
C35—C36—C74	112.9 (3)	C82—C81—C30	113.3 (3)
C53—C36—C74	114.2 (3)	C83—C81—C30	112.7 (3)
C17—C37—C38	108.7 (3)	F823—C82—F821	107.7 (3)
C17—C37—C36	125.3 (3)	F823—C82—F822	107.3 (3)
C38—C37—C36	121.1 (3)	F821—C82—F822	107.0 (3)
C39—C38—C19	120.0 (3)	F823—C82—C81	112.4 (3)
C39—C38—C37	120.8 (3)	F821—C82—C81	111.5 (3)
C19—C38—C37	108.0 (3)	F822—C82—C81	110.7 (3)
C38—C39—C40	119.8 (3)	F833—C83—F832	108.8 (3)
C38—C39—C54	120.0 (3)	F833—C83—F831	107.9 (3)
C40—C39—C54	107.5 (3)	F832—C83—F831	106.7 (3)
C21—C40—C41	119.3 (3)	F833—C83—C81	112.4 (3)
C21—C40—C39	120.5 (3)	F832—C83—C81	110.0 (3)
C41—C40—C39	108.3 (3)	F831—C83—C81	110.9 (3)
C42—C41—C40	119.1 (3)	F841—C84—C85	105.6 (3)
C42—C41—C55	120.2 (3)	F841—C84—C86	105.9 (3)
C40—C41—C55	108.9 (3)	C85—C84—C86	110.6 (3)
C41—C42—C23	121.1 (3)	F841—C84—C47	108.0 (3)
C41—C42—C43	119.7 (3)	C85—C84—C47	114.0 (3)
C23—C42—C43	107.6 (3)	C86—C84—C47	112.2 (3)
C57—C43—C44	119.6 (3)	F851—C85—F853	106.2 (3)
C57—C43—C42	119.5 (3)	F851—C85—F852	108.1 (3)
C44—C43—C42	108.6 (3)	F853—C85—F852	108.4 (3)
C45—C44—C43	119.4 (3)	F851—C85—C84	111.0 (3)
C45—C44—C24	120.2 (3)	F853—C85—C84	111.9 (3)
C43—C44—C24	108.3 (3)	F852—C85—C84	111.0 (3)
C44—C45—C27	119.6 (3)	F862—C86—F863	107.1 (3)
C44—C45—C46	121.1 (3)	F862—C86—F861	108.0 (3)
C27—C45—C46	108.1 (3)	F863—C86—F861	106.9 (3)
C58—C46—C45	119.0 (3)	F862—C86—C84	111.5 (3)
C58—C46—C47	123.3 (3)	F863—C86—C84	112.4 (3)
C45—C46—C47	110.1 (3)	F861—C86—C84	110.6 (3)

Experimental details

Crystal data
Chemical formula	C₇₈F₄₂
M_r	1734.78
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	13.5877 (3), 31.1809 (7), 13.7240 (3)
β (°)	106.873 (1)
V (Å³)	5564.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.11 × 0.06

Data collection
Diffractometer	Bruker Kappa APEX II diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 2003)
T_min, T_max	0.937, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	75325, 11386, 6862
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.133, 1.01
No. of reflections	11386
No. of parameters	1081
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.32

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

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