1,4,10,19,25,41,55,60,67,69-Decakis(trifluoro­meth­yl)-1,4,10,19,25,41,55,60,67,69-deca­hydro­(C₇₀-D_5h)[5,6]fullerene

The title compound, C₈₀F₃₀, is one of seven isomers of C₇₀(CF₃)₁₀ that have been isolated. The C₂-symmetry fullerene mol­ecule has an idealized D_5h C₇₀ core with the ten CF₃ groups arranged on a `pole-to-pole' para-meta-para-para-para-para-para-meta-para (pmp⁵mp) ribbon of edge-sharing C₆(CF₃)₂ hexa­gons. There are no cage Csp³—Csp³ bonds. There are intra­molecular F...F contacts between pairs of CF₃ groups on the same hexa­gon that range from 2.560 (3) to 2.876 (3) Å. Two CF₃ groups are disordered with almost equal occupancies.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.053
• wR factor = 0.124
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom F11     has ADP max/min Ratio .............       4.40 prola
PLAT220_ALERT_2_B Large Non-Solvent    F     Ueq(max)/Ueq(min) ...       3.62 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
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 .......          ?
PLAT213_ALERT_2_C Atom F12     has ADP max/min Ratio .............       3.90 prola
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C74
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C75
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  F6     ..  C22     ..       2.92 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  F8     ..  C16     ..       2.96 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      37.00 A   3 
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.40 Deg.
              C75  -C19  -C75A    1.555   1.555   1.555

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:C80 F30
PLAT793_ALERT_1_G Check the Absolute Configuration of C10    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C25    = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         25

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

---

S1. Comment

Recently reported high-temperature reactions of C₇₀ with CF₃I have yielded more than two dozen 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, Kuvychko, Lebedkin 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, Kareev, Shustova et al., 2007; Shustova, Peryshkov, Kareev, et al., 2007). A member of the n = 10 set of seven isomers (Popov, Kareev, Shustova et al., 2007), the title compound has been crystallized from toluene and we report its crystal structure here.

The structure of the title compound, as shown in Figs. 1 and 2, comprises an idealized D_{5 h} C₇₀ core with ten sp³ carbon atoms at positions 1, 4, 10, 19, 25, 41, 55, 60, 67, and 69 (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-para-para- meta-para (pmp⁵mp) ribbon of edge-sharing C₆(CF₃)₂ hexagons. The shared edges in each ribbon of hexagons are C(sp³)-C(sp²) bonds (e.g., C1—C2, C4—C5, etc.), not C(sp²)-C(sp²) bonds. Thus, any pair of adjacent hexagons along the ribbon has a common CF₃ group.

The two CF₃ groups in the middle of the ribbon are disordered and were refined as half atoms. Only one 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 2.539 (3) to 2.756 (3) Å. The range of C^···F distances that do not involve the disordered CF₃ groups is from 1.323 (3) to 1.338 (3) Å.

The shortest cage C—C bond in the asymmetric unit is C8—C9, at 1.349 (4) Å. This is significantly shorter than the shortest C—C bond of this type in the most precise structure of empty C₇₀ reported to date (C₉H₃Cl₆N^.3(C₇₀)^.3(C₆H₅Cl)), which is 1.440 (4) Å (Pham et al., 2007). More importantly, the C8—C9 bond is a pentagon-hexagon junction, and the shortest pent-hex junction in C₉H₃Cl₆N^.3(C₇₀)^.3(C₆H₅Cl)) is also 1.440 (4) Å (the longest pent-hex junction in C₉H₃Cl₆N^.3(C₇₀)^.3(C₆H₅Cl)) is 1.460 (4) Å.

Related literature

For related literature, see: Avdoshenko et al. (2006); Goryunkov et al. (2006); Ignat'eva et al. (2006); Kareev et al. (2005, 2006a,b); Pham et al. (2007); Popov et al. (2007); Powell et al. (2002); Shustova et al. (2007).

S2. Experimental

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

S3. Refinement

The maximum (0.47 e/ų) and minimum (-0.54 e/ų) residual electron density peaks were located 0.66 Šand 0.24 Šfrom F11.

Computing details

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

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. The crystallographic C2 axis is perpendicular to the plane of the page. Only one pair of the disordered CF3 groups on the hexagon centered on the C2 axis is shown.

Fig. 2. (Left) Schlegel diagram showing the IUPAC lowest-locants for the cage carbon atoms. The C2 axis passes through the center of the hexagon with C19 and C41 and bisects the C30—C50 bond. The CF3 groups are attached to the cage carbon atoms depicted as black circles. Also shown is the ribbon of meta- and para-C6(CF3)2 edge-sharing hexagons (the two meta-C6(CF3)2 hexagons are indicated with the letter m). (Right) The structure showing the atom numbers for the CF3 groups and the network of F^···F contacts between CF3 groups that share the same hexagon.

1,4,10,19,25,41,55,60,67,69-Decakis(trifluoromethyl)- 1,4,10,19,25,41,55,60,67,69-decahydro(C₇₀—D_{5 h})[5,6]fullerene

Crystal data

C80F30	Dx = 2.012 Mg m^−3
Mr = 1530.80	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 999 reflections
a = 16.0658 (3) Å	θ = 1.7–27.9°
b = 17.2662 (4) Å	µ = 0.20 mm^−1
c = 18.2153 (4) Å	T = 100 K
V = 5052.84 (19) Å^3	Plate, red
Z = 4	0.44 × 0.10 × 0.05 mm
F(000) = 3000

Data collection

Bruker Kappa APEXII diffractometer	5853 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
φ and ω scans	θmax = 27.9°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −19→21
Tmin = 0.920, Tmax = 0.990	k = −20→21
53138 measured reflections	l = −23→19

Refinement

Refinement on F^2	25 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.053	Secondary atom site location: difference Fourier map
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 4.0833P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.026
5853 reflections	Δρmax = 0.47 e Å^−3
534 parameters	Δρmin = −0.54 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.14807 (15)	0.84689 (16)	0.57610 (14)	0.0172 (6)
C2	0.06726 (15)	0.89202 (16)	0.56364 (14)	0.0171 (6)
C3	−0.00314 (15)	0.85035 (16)	0.54804 (14)	0.0179 (6)
C4	−0.01274 (16)	0.76084 (17)	0.55711 (15)	0.0212 (7)
C5	0.05113 (16)	0.73164 (16)	0.61305 (15)	0.0192 (6)
C6	0.12706 (15)	0.76964 (16)	0.61409 (15)	0.0171 (6)
C7	0.18225 (15)	0.76010 (16)	0.67239 (15)	0.0181 (6)
C8	0.22979 (14)	0.83155 (16)	0.68340 (14)	0.0161 (6)
C9	0.20545 (14)	0.88497 (16)	0.63383 (14)	0.0158 (6)
C10	0.20897 (15)	0.97126 (16)	0.64795 (14)	0.0163 (6)
C11	0.12152 (15)	1.00488 (16)	0.63621 (15)	0.0169 (6)
C12	0.06016 (15)	0.97158 (16)	0.59058 (14)	0.0161 (6)
C13	−0.02077 (15)	1.00408 (16)	0.59698 (15)	0.0181 (6)
C14	−0.09317 (15)	0.96120 (17)	0.57594 (14)	0.0187 (6)
C15	−0.08409 (15)	0.88541 (18)	0.55430 (14)	0.0208 (7)
C16	−0.14344 (15)	0.82795 (17)	0.57804 (15)	0.0203 (7)
C17	−0.10068 (15)	0.75657 (17)	0.58928 (15)	0.0216 (7)
C18	−0.12203 (16)	0.71052 (17)	0.64672 (16)	0.0224 (7)
C19	−0.06088 (16)	0.65728 (16)	0.68667 (16)	0.0227 (7)
C20	0.02896 (16)	0.68342 (16)	0.67393 (16)	0.0213 (7)
C21	0.08471 (16)	0.67492 (16)	0.73207 (16)	0.0219 (7)
C22	0.16204 (15)	0.71231 (16)	0.73075 (15)	0.0201 (6)
C23	0.18732 (15)	0.73373 (17)	0.80518 (15)	0.0208 (7)
C24	0.23331 (15)	0.79965 (17)	0.81776 (15)	0.0191 (6)
C25	0.27335 (15)	0.84797 (16)	0.75587 (15)	0.0196 (6)
C26	0.24996 (15)	0.93044 (17)	0.77931 (15)	0.0188 (6)
C27	0.21993 (15)	0.98455 (16)	0.73100 (14)	0.0179 (6)
C28	0.15831 (16)	1.03892 (16)	0.75525 (15)	0.0193 (6)
C29	0.09863 (16)	1.05095 (16)	0.69643 (15)	0.0187 (6)
C30	0.01394 (16)	1.07106 (15)	0.71141 (15)	0.0174 (6)
C31	−0.04340 (15)	1.05362 (16)	0.65680 (15)	0.0173 (6)
C32	−0.13118 (15)	1.04049 (16)	0.67284 (15)	0.0185 (6)
C33	−0.16206 (15)	0.98408 (17)	0.62258 (15)	0.0203 (6)
C45	0.20949 (15)	0.84927 (17)	0.87587 (15)	0.0209 (7)
C46	0.21946 (15)	0.92902 (17)	0.85350 (15)	0.0203 (7)
C71	0.36707 (16)	0.83212 (18)	0.75032 (16)	0.0232 (7)
C72	0.27308 (16)	1.01737 (17)	0.60260 (15)	0.0208 (6)
C73	0.19695 (16)	0.83397 (17)	0.50429 (15)	0.0218 (7)
C74	−0.00903 (18)	0.7147 (2)	0.48471 (18)	0.0334 (8)
F1	0.40336 (9)	0.87577 (10)	0.69942 (9)	0.0298 (4)
F2	0.40463 (9)	0.84669 (11)	0.81408 (9)	0.0356 (5)
F3	0.38117 (10)	0.75794 (10)	0.73328 (10)	0.0354 (5)
F4	0.34564 (9)	0.98094 (10)	0.59759 (9)	0.0324 (4)
F5	0.24686 (9)	1.03264 (10)	0.53477 (8)	0.0281 (4)
F6	0.28737 (11)	1.08613 (10)	0.63398 (9)	0.0373 (5)
F7	0.24219 (11)	0.89500 (11)	0.48588 (10)	0.0401 (5)
F8	0.24879 (11)	0.77447 (11)	0.51097 (9)	0.0424 (5)
F9	0.14794 (10)	0.81972 (11)	0.44729 (9)	0.0376 (5)
F10	0.06645 (10)	0.69174 (11)	0.46686 (9)	0.0389 (5)
F11	−0.05481 (16)	0.65144 (16)	0.48843 (15)	0.1015 (12)
F12	−0.03764 (16)	0.75595 (16)	0.42896 (11)	0.0793 (9)
F13	−0.0496 (3)	0.5632 (3)	0.5902 (3)	0.053 (2)	0.511 (8)
F14	−0.0479 (5)	0.5247 (3)	0.7019 (4)	0.060 (3)	0.511 (8)
F15	−0.1603 (3)	0.5624 (4)	0.6519 (4)	0.0402 (15)	0.511 (8)
C75	−0.0798 (8)	0.5751 (6)	0.6567 (7)	0.021 (3)	0.511 (8)
F13A	−0.1288 (5)	0.5590 (4)	0.6213 (4)	0.0464 (19)	0.489 (8)
F14A	−0.0029 (3)	0.5355 (2)	0.6456 (4)	0.052 (2)	0.489 (8)
F15A	−0.0943 (4)	0.5270 (3)	0.7297 (3)	0.0397 (14)	0.489 (8)
C75A	−0.0701 (9)	0.5695 (6)	0.6721 (7)	0.026 (4)	0.489 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0157 (12)	0.0214 (16)	0.0144 (15)	−0.0016 (11)	0.0022 (11)	−0.0013 (13)
C2	0.0184 (13)	0.0260 (17)	0.0068 (13)	0.0017 (11)	0.0034 (10)	0.0004 (13)
C3	0.0195 (13)	0.0248 (17)	0.0094 (14)	−0.0003 (11)	0.0003 (11)	−0.0056 (13)
C4	0.0186 (14)	0.0266 (18)	0.0184 (16)	−0.0040 (12)	0.0028 (11)	−0.0114 (13)
C5	0.0203 (13)	0.0177 (16)	0.0196 (15)	0.0012 (11)	0.0043 (11)	−0.0097 (13)
C6	0.0166 (13)	0.0166 (16)	0.0182 (15)	0.0006 (11)	0.0056 (11)	−0.0055 (13)
C7	0.0127 (12)	0.0184 (16)	0.0231 (16)	0.0043 (11)	0.0049 (11)	−0.0021 (13)
C8	0.0114 (12)	0.0199 (16)	0.0170 (15)	0.0009 (10)	0.0036 (10)	−0.0018 (13)
C9	0.0137 (12)	0.0206 (16)	0.0130 (14)	−0.0009 (11)	0.0056 (10)	−0.0028 (13)
C10	0.0164 (12)	0.0186 (16)	0.0139 (14)	−0.0031 (11)	0.0000 (11)	−0.0009 (12)
C11	0.0210 (13)	0.0145 (15)	0.0153 (15)	−0.0021 (11)	0.0045 (11)	0.0035 (12)
C12	0.0204 (13)	0.0206 (17)	0.0073 (14)	0.0002 (11)	0.0020 (11)	0.0038 (12)
C13	0.0224 (14)	0.0208 (17)	0.0109 (15)	0.0017 (11)	0.0016 (11)	0.0052 (13)
C14	0.0187 (13)	0.0283 (18)	0.0092 (14)	0.0046 (12)	−0.0030 (10)	0.0050 (13)
C15	0.0176 (13)	0.037 (2)	0.0075 (14)	0.0006 (12)	−0.0022 (11)	−0.0045 (13)
C16	0.0169 (13)	0.0309 (18)	0.0133 (15)	−0.0002 (12)	−0.0059 (11)	−0.0079 (13)
C17	0.0154 (13)	0.0305 (18)	0.0188 (16)	−0.0068 (12)	0.0001 (11)	−0.0135 (14)
C18	0.0193 (13)	0.0237 (17)	0.0242 (17)	−0.0070 (12)	0.0012 (12)	−0.0120 (14)
C19	0.0218 (14)	0.0168 (17)	0.0294 (17)	−0.0046 (11)	0.0076 (12)	−0.0073 (14)
C20	0.0199 (13)	0.0136 (16)	0.0305 (18)	−0.0005 (11)	0.0073 (12)	−0.0088 (14)
C21	0.0215 (14)	0.0111 (15)	0.0332 (18)	0.0027 (11)	0.0083 (12)	0.0012 (13)
C22	0.0161 (13)	0.0172 (16)	0.0272 (17)	0.0059 (11)	0.0044 (12)	0.0020 (14)
C23	0.0159 (13)	0.0227 (17)	0.0237 (16)	0.0071 (11)	0.0014 (12)	0.0080 (14)
C24	0.0115 (12)	0.0268 (18)	0.0190 (15)	0.0054 (11)	−0.0003 (11)	0.0086 (13)
C25	0.0138 (12)	0.0265 (17)	0.0185 (15)	0.0000 (11)	−0.0001 (11)	0.0031 (14)
C26	0.0107 (12)	0.0283 (17)	0.0174 (15)	−0.0040 (11)	0.0003 (11)	−0.0010 (14)
C27	0.0162 (12)	0.0206 (16)	0.0168 (15)	−0.0077 (11)	0.0008 (11)	−0.0025 (13)
C28	0.0199 (13)	0.0170 (16)	0.0209 (16)	−0.0075 (11)	0.0027 (11)	−0.0023 (13)
C29	0.0238 (14)	0.0133 (16)	0.0191 (16)	−0.0032 (11)	0.0032 (12)	0.0064 (13)
C30	0.0263 (14)	0.0072 (14)	0.0187 (15)	0.0004 (11)	0.0029 (12)	0.0011 (12)
C31	0.0214 (13)	0.0157 (16)	0.0150 (15)	0.0039 (11)	0.0027 (11)	0.0070 (12)
C32	0.0205 (13)	0.0201 (16)	0.0147 (15)	0.0085 (11)	−0.0006 (11)	0.0050 (13)
C33	0.0180 (13)	0.0288 (18)	0.0140 (15)	0.0082 (12)	−0.0034 (11)	0.0061 (13)
C45	0.0126 (12)	0.0342 (19)	0.0161 (15)	0.0017 (12)	−0.0060 (11)	0.0053 (14)
C46	0.0123 (12)	0.0337 (19)	0.0148 (15)	−0.0040 (12)	−0.0046 (11)	0.0005 (14)
C71	0.0151 (13)	0.033 (2)	0.0218 (16)	0.0016 (12)	−0.0007 (12)	0.0051 (15)
C72	0.0211 (14)	0.0236 (18)	0.0177 (16)	−0.0044 (12)	−0.0005 (11)	−0.0014 (14)
C73	0.0168 (13)	0.0291 (18)	0.0194 (16)	−0.0016 (12)	0.0018 (12)	−0.0023 (14)
C74	0.0258 (16)	0.043 (2)	0.0315 (19)	−0.0086 (15)	0.0094 (14)	−0.0174 (17)
F1	0.0171 (8)	0.0452 (12)	0.0270 (10)	−0.0027 (7)	0.0034 (7)	0.0059 (9)
F2	0.0168 (8)	0.0643 (13)	0.0256 (10)	−0.0002 (8)	−0.0042 (7)	0.0052 (9)
F3	0.0215 (8)	0.0346 (12)	0.0501 (12)	0.0089 (7)	0.0046 (8)	0.0034 (9)
F4	0.0177 (8)	0.0434 (11)	0.0361 (11)	−0.0030 (7)	0.0064 (7)	0.0092 (9)
F5	0.0277 (8)	0.0388 (11)	0.0177 (9)	−0.0057 (7)	0.0022 (7)	0.0079 (8)
F6	0.0518 (11)	0.0297 (11)	0.0302 (10)	−0.0222 (8)	0.0131 (8)	−0.0067 (9)
F7	0.0467 (11)	0.0412 (12)	0.0325 (11)	−0.0192 (9)	0.0217 (9)	−0.0082 (9)
F8	0.0464 (11)	0.0493 (13)	0.0315 (11)	0.0266 (9)	0.0178 (9)	0.0039 (10)
F9	0.0282 (9)	0.0677 (14)	0.0168 (9)	−0.0052 (9)	0.0048 (7)	−0.0127 (9)
F10	0.0309 (10)	0.0548 (13)	0.0310 (11)	0.0059 (9)	0.0081 (8)	−0.0190 (9)
F11	0.0947 (18)	0.101 (2)	0.109 (2)	−0.0763 (16)	0.0727 (17)	−0.0905 (18)
F12	0.0927 (18)	0.112 (2)	0.0335 (13)	0.0535 (15)	−0.0346 (12)	−0.0437 (14)
F13	0.071 (4)	0.036 (3)	0.054 (3)	−0.021 (2)	0.030 (3)	−0.026 (2)
F14	0.088 (6)	0.021 (3)	0.072 (5)	−0.001 (3)	−0.054 (5)	0.001 (3)
F15	0.025 (2)	0.031 (3)	0.064 (4)	−0.008 (2)	−0.003 (2)	−0.016 (3)
C75	0.018 (5)	0.016 (6)	0.028 (6)	−0.002 (4)	−0.001 (4)	−0.005 (4)
F13A	0.066 (5)	0.024 (3)	0.049 (4)	−0.004 (3)	−0.029 (4)	−0.007 (3)
F14A	0.039 (3)	0.021 (3)	0.096 (6)	−0.0068 (18)	0.038 (3)	−0.022 (3)
F15A	0.064 (4)	0.020 (2)	0.036 (3)	−0.011 (2)	0.006 (2)	0.001 (2)
C75A	0.019 (5)	0.040 (9)	0.019 (6)	−0.004 (5)	0.002 (4)	−0.003 (5)

Geometric parameters (Å, º)

C1—C2	1.531 (4)	C21—C19^i	1.559 (4)
C1—C6	1.540 (4)	C22—C23	1.463 (4)
C1—C73	1.542 (4)	C23—C24	1.376 (4)
C1—C9	1.545 (4)	C23—C18^i	1.424 (4)
C2—C3	1.370 (4)	C24—C45	1.415 (4)
C2—C12	1.463 (4)	C24—C25	1.543 (4)
C3—C15	1.439 (4)	C25—C26	1.533 (4)
C3—C4	1.562 (4)	C25—C71	1.534 (4)
C4—C17	1.531 (4)	C26—C27	1.371 (4)
C4—C5	1.531 (4)	C26—C46	1.438 (4)
C4—C74	1.542 (4)	C27—C28	1.434 (4)
C5—C6	1.385 (4)	C28—C32^i	1.381 (4)
C5—C20	1.432 (4)	C28—C29	1.453 (4)
C6—C7	1.393 (4)	C29—C30	1.430 (4)
C7—C22	1.384 (4)	C30—C31	1.389 (4)
C7—C8	1.465 (4)	C30—C30^i	1.475 (5)
C8—C9	1.349 (4)	C31—C32	1.458 (4)
C8—C25	1.521 (4)	C32—C28^i	1.381 (4)
C9—C10	1.513 (4)	C32—C33	1.426 (4)
C10—C11	1.535 (3)	C33—C46^i	1.394 (4)
C10—C27	1.540 (4)	C45—C16^i	1.402 (4)
C10—C72	1.542 (4)	C45—C46	1.445 (4)
C11—C29	1.404 (4)	C46—C33^i	1.394 (4)
C11—C12	1.412 (4)	C71—F1	1.330 (3)
C12—C13	1.421 (4)	C71—F2	1.333 (3)
C13—C14	1.431 (4)	C71—F3	1.337 (3)
C13—C31	1.432 (4)	C72—F4	1.328 (3)
C14—C15	1.374 (4)	C72—F5	1.332 (3)
C14—C33	1.450 (4)	C72—F6	1.338 (3)
C15—C16	1.442 (4)	C73—F7	1.323 (3)
C16—C45^i	1.402 (4)	C73—F9	1.326 (3)
C16—C17	1.426 (4)	C73—F8	1.328 (3)
C17—C18	1.358 (4)	C74—F10	1.316 (3)
C18—C23^i	1.424 (4)	C74—F11	1.319 (4)
C18—C19	1.530 (4)	C74—F12	1.323 (4)
C19—C20	1.530 (4)	F13—C75	1.322 (12)
C19—C75	1.551 (10)	F14—C75	1.303 (12)
C19—C75A	1.546 (11)	F15—C75	1.315 (12)
C19—C21^i	1.559 (4)	F13A—C75A	1.332 (13)
C20—C21	1.395 (4)	F14A—C75A	1.321 (13)
C21—C22	1.400 (4)	F15A—C75A	1.339 (13)
C2—C1—C6	108.8 (2)	C7—C22—C23	119.7 (2)
C2—C1—C73	112.3 (2)	C21—C22—C23	110.3 (2)
C6—C1—C73	111.6 (2)	C24—C23—C18^i	121.7 (3)
C2—C1—C9	113.0 (2)	C24—C23—C22	120.8 (3)
C6—C1—C9	101.2 (2)	C18^i—C23—C22	107.1 (2)
C73—C1—C9	109.6 (2)	C23—C24—C45	118.7 (2)
C3—C2—C12	119.9 (2)	C23—C24—C25	123.3 (3)
C3—C2—C1	117.6 (2)	C45—C24—C25	109.4 (2)
C12—C2—C1	119.6 (2)	C8—C25—C26	107.6 (2)
C2—C3—C15	120.6 (3)	C8—C25—C71	111.2 (2)
C2—C3—C4	125.4 (2)	C26—C25—C71	115.1 (2)
C15—C3—C4	108.6 (2)	C8—C25—C24	110.0 (2)
C17—C4—C5	110.4 (2)	C26—C25—C24	101.3 (2)
C17—C4—C74	109.8 (2)	C71—C25—C24	111.2 (2)
C5—C4—C74	111.9 (2)	C27—C26—C46	119.7 (2)
C17—C4—C3	100.3 (2)	C27—C26—C25	122.7 (2)
C5—C4—C3	109.3 (2)	C46—C26—C25	109.2 (2)
C74—C4—C3	114.6 (2)	C26—C27—C28	119.4 (2)
C6—C5—C20	118.9 (2)	C26—C27—C10	124.7 (2)
C6—C5—C4	116.3 (2)	C28—C27—C10	108.7 (2)
C20—C5—C4	122.7 (2)	C32^i—C28—C27	121.5 (3)
C5—C6—C7	121.0 (3)	C32^i—C28—C29	119.2 (2)
C5—C6—C1	126.7 (2)	C27—C28—C29	108.8 (2)
C7—C6—C1	107.8 (2)	C11—C29—C30	122.4 (2)
C22—C7—C6	120.4 (2)	C11—C29—C28	108.8 (2)
C22—C7—C8	121.3 (2)	C30—C29—C28	121.5 (2)
C6—C7—C8	109.7 (2)	C31—C30—C29	116.2 (2)
C9—C8—C7	109.5 (2)	C31—C30—C30^i	118.8 (3)
C9—C8—C25	126.0 (2)	C29—C30—C30^i	118.1 (3)
C7—C8—C25	121.0 (2)	C30—C31—C13	120.4 (2)
C8—C9—C10	123.3 (2)	C30—C31—C32	122.1 (2)
C8—C9—C1	109.7 (2)	C13—C31—C32	107.8 (2)
C10—C9—C1	123.9 (2)	C28^i—C32—C33	119.1 (3)
C9—C10—C11	108.3 (2)	C28^i—C32—C31	119.9 (2)
C9—C10—C27	108.5 (2)	C33—C32—C31	108.3 (2)
C11—C10—C27	100.7 (2)	C46^i—C33—C32	119.7 (2)
C9—C10—C72	116.3 (2)	C46^i—C33—C14	120.1 (3)
C11—C10—C72	110.0 (2)	C32—C33—C14	107.3 (2)
C27—C10—C72	111.9 (2)	C16^i—C45—C24	119.6 (3)
C29—C11—C12	120.5 (2)	C16^i—C45—C46	120.2 (3)
C29—C11—C10	110.2 (2)	C24—C45—C46	109.6 (2)
C12—C11—C10	124.5 (2)	C33^i—C46—C26	120.5 (3)
C11—C12—C13	115.5 (2)	C33^i—C46—C45	119.2 (2)
C11—C12—C2	121.7 (2)	C26—C46—C45	108.6 (2)
C13—C12—C2	118.0 (2)	F1—C71—F2	107.6 (2)
C12—C13—C14	121.2 (2)	F1—C71—F3	107.9 (2)
C12—C13—C31	122.0 (2)	F2—C71—F3	107.8 (2)
C14—C13—C31	107.8 (2)	F1—C71—C25	112.0 (2)
C15—C14—C13	118.9 (2)	F2—C71—C25	110.7 (2)
C15—C14—C33	120.6 (3)	F3—C71—C25	110.6 (2)
C13—C14—C33	108.8 (2)	F4—C72—F5	107.9 (2)
C14—C15—C3	121.3 (2)	F4—C72—F6	107.4 (2)
C14—C15—C16	119.9 (2)	F5—C72—F6	106.0 (2)
C3—C15—C16	109.4 (3)	F4—C72—C10	112.3 (2)
C45^i—C16—C17	120.4 (3)	F5—C72—C10	112.8 (2)
C45^i—C16—C15	119.9 (3)	F6—C72—C10	110.1 (2)
C17—C16—C15	108.6 (2)	F7—C73—F9	106.0 (2)
C18—C17—C16	119.7 (2)	F7—C73—F8	107.2 (2)
C18—C17—C4	123.8 (3)	F9—C73—F8	107.5 (2)
C16—C17—C4	110.4 (2)	F7—C73—C1	112.3 (2)
C17—C18—C23^i	119.7 (3)	F9—C73—C1	112.9 (2)
C17—C18—C19	123.8 (2)	F8—C73—C1	110.7 (2)
C23^i—C18—C19	110.5 (2)	F10—C74—F11	106.1 (3)
C18—C19—C20	110.9 (2)	F10—C74—F12	107.0 (3)
C18—C19—C75	104.9 (5)	F11—C74—F12	107.0 (3)
C20—C19—C75	113.7 (5)	F10—C74—C4	113.7 (2)
C18—C19—C75A	116.5 (6)	F11—C74—C4	111.3 (3)
C20—C19—C75A	110.7 (5)	F12—C74—C4	111.4 (3)
C75—C19—C75A	12.4 (8)	F14—C75—F13	109.3 (10)
C18—C19—C21^i	100.2 (2)	F14—C75—F15	108.6 (9)
C20—C19—C21^i	108.6 (2)	F13—C75—F15	105.9 (10)
C75—C19—C21^i	117.7 (5)	F14—C75—C19	108.2 (8)
C75A—C19—C21^i	109.4 (5)	F13—C75—C19	113.1 (8)
C21—C20—C5	119.3 (2)	F15—C75—C19	111.6 (8)
C21—C20—C19	117.4 (3)	F13A—C75A—F14A	105.4 (10)
C5—C20—C19	121.6 (2)	F13A—C75A—F15A	105.3 (9)
C20—C21—C22	120.5 (3)	F14A—C75A—F15A	106.2 (10)
C20—C21—C19^i	125.7 (2)	F13A—C75A—C19	108.7 (9)
C22—C21—C19^i	108.9 (2)	F14A—C75A—C19	114.8 (9)
C7—C22—C21	119.7 (3)	F15A—C75A—C19	115.5 (9)

Symmetry code: (i) −x, y, −z+3/2.