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ISSN: 2056-9890

Crystal structures of three hexa­kis­­(fluoroar­yl­oxy)cyclo­triphosphazenes

aPennsylvania State University, Department of Biochemistry and Molecular Biology, 108 Althouse Laboratory, University Park, PA 16802, USA, and bPennsylvania State University, Department of Chemistry, 118 Chemistry Building, University Park, PA 16802, USA
*Correspondence e-mail: hpy1@psu.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 September 2019; accepted 18 September 2019; online 27 September 2019)

The syntheses and crystal structures of three cyclo­triphosphazenes, all with fluorinated ar­yloxy side groups that generate different steric characteristics, viz. hexa­kis­(penta­fluoro­phen­oxy)cyclo­triphosphazene, N3P3(OC6F5)6, 1, hexa­kis­[4-(tri­fluoro­methyl)­phen­oxy]cyclo­triphosphazene, N3P3[OC6H4(CF3)]6, 2 and hexa­kis­[3,5-bis(­tri­fluoro­methyl)­phen­oxy]cyclo­triphosphazene, N3P3[OC6H3(CF3)2]6 3, are reported. Specifically, each phospho­rus atom bears either two penta­fluoro­phen­oxy, 4-tri­fluoro­methyl­phen­oxy, or 3,5-tri­fluoro­methyl­phen­oxy groups. The central six-membered phosphazene rings display envelope pucker conformations in each case, albeit to varying degrees. The maximum displacement of the `flap atom' from the plane through the other ring atoms [0.308 (5) Å] is seen in 1, in a mol­ecule that is devoid of hydrogen atoms and which exhibits a `wind-swept' look with all the aromatic rings displaced in the same direction. In 3 an intra­molecular C—H(aromatic)⋯F inter­action is observed. All the –CF3 groups in 2 and 3 exhibit positional disorder over two rotated orientations in close to statistical ratios. The extended structures of 2 and 3 are consolidated by C—H⋯F inter­actions of two kinds: (a) linear chains, and (b) cyclic between mol­ecules related by inversion centers. In both 1 and 3, one of the six substituted phenyl rings has a parallel-displaced aromatic ππ stacking inter­action with its respective symmetry mate with slippage values of 2.2 Å in 1 and 1.0 Å in 3. None of the structures reported here have solvent voids that could lead to clathrate formation.

1. Chemical context

Cyclic organophosphazenes have a long history as representatives of inorganic heterocyclic rings, and are also the focus of arguments about reactivity and pseudoaromaticity in inorganic systems (Allcock, 1972[Allcock, H. R. (1972). Phosphorus Nitrogen Compounds. Cyclic, Linear, and High Polymeric Systems. London: Academic Press.]; Steudel, 1992[Steudel, R. (1992). Editor. The Chemistry of Inorganic Ring Systems. Amsterdam, New York: Elsevier.]). In our research program these compounds also serve another purpose – as synthesis and structural models for linear high polymeric organophosphazenes. These cyclic small mol­ecules provide preliminary information related to intra- and inter­molecular side-group inter­actions, which affect many polymer properties.

As part of our ongoing work in this area, the three cyclo­triphosphazenes hexa­kis­(penta­fluoro­phen­oxy)cyclo­tri­phos­phazene N3P3(OC6F5)6 (1), hexa­kis­[4-(tri­fluoro­methyl)­phenoxy]cyclo­triphosphazene N3P3[OC6H4(CF3)]6 (2) and hexa­kis­[3,5-bis(tri­fluoro­methyl­phen­oxy]cyclo­triphosphazene; N3P3[OC6H3(CF3)2]6 (3) were synthesized by the reactions of hexa­chloro­cyclo­triphosphazene with the appropriate sodium fluoro-aryl­oxides in THF or dioxane solvent. Forcing reaction conditions (boiling dioxane) were required for complete chlorine replacement in the case of the penta­fluoro­phen­oxy derivative (1) presumably due to steric hindrance. The three compounds were characterized by NMR spectroscopy in addition to x-ray crystallography.

The structure of a fourth, related cyclo­triphosphazene with six para-fluoro­phen­oxy groups, was reported by other investigators (Wahl et al., 2012[Wahl, H., Haynes, D. A. & le Roex, T. (2012). Cryst. Growth Des. 12, 4031-4038.]) and was independently verified by us. The non-fluorinated hexa­(phen­oxy)cyclo­triphosphazene tetra­hydro­furan solvate x-ray structure was also described earlier (Dietrich et al., 2000[Dietrich, A., Neumüller, B. & Dehnicke, K. (2000). Z. Anorg. Allg. Chem. 626, 2035-2037.]).

[Scheme 1]

2. Structural commentary

The structures of 1, 2 and 3 (Figs. 1[link], 2[link] and 3[link]) presented in this report have the hexa­phen­oxy-cyclo­triphosphazene moiety as the common core of the mol­ecule, and differ only in the substitutions on the phenyl rings. The cyclo­triphosphazene ring in these structures exhibit varying degree of envelope pucker. The maximum pucker is seen in 1 wherein the displacement of atom P3 from the plane defined by the other five atoms of the ring (each member atom less than 0.05 Å from the plane) is 0.308 (5) Å. A similar calculation in 2 shows atom P2 displaced by 0.232 (4) Å, and in 3 atom N3 is displaced the least, only by 0.205 (4) Å. In earlier structure reports: [(NPCl2)3: Bullen, 1971[Bullen, G. J. (1971). J. Chem. Soc. A, pp. 1450-1453.]; (NPF2)3: Singh et al., 2000[Singh, R. P., Vij, A., Kirchmeier, R. L. & Shreeve, J. M. (2000). Inorg. Chem. 39, 375-377.]; (NPPh2)3·THF: Dietrich et al., 2000[Dietrich, A., Neumüller, B. & Dehnicke, K. (2000). Z. Anorg. Allg. Chem. 626, 2035-2037.]], the cyclo­triphosphazene ring was always planar, i.e. no puckering was seen.

[Figure 1]
Figure 1
The mol­ecular structure of 1 with displacement ellipsoids drawn at the 50% probability level.
[Figure 2]
Figure 2
The mol­ecular structure of 2 with displacement ellipsoids drawn at the 50% probability level.
[Figure 3]
Figure 3
The mol­ecular structure of 3 with displacement ellipsoids drawn at the 50% probability level. The intra­molecular C—H⋯F inter­action is indicated by dashed lines.

The mol­ecular structure of 1 has a `wind-swept' appearance (Fig. 4[link]) with all six penta­fluoro­phenyl rings seemingly pushed in one direction with respect to the cyclo­triphosphazene ring. In all the structures here, a pair of aryl­oxy groups is attached to each of the three phospho­rous atoms of each mol­ecule. Comparing the orientation of the rings within each pair, in 1 they are almost orthogonal to each other with the three dihedral angles being 72.3 (2), 76.1 (2) and 80.3 (2)°; in 2 they are between parallel and orthogonal with dihedral angles of 27.3 (2), 33.2 (2) and 62.6 (2)°, and in 3 the dihedral angles cover the widest range: 30.2 (2), 45.1 (2) and 82.4 (2)°. The tri­fluoro methyl groups in 2 and 3 are all positionally disordered. A C10—H10⋯F26 intra­molecular inter­action is observed in 3 [H⋯F = 2.58, C⋯F = 3.478 (4) Å, C—H⋯F = 163°].

[Figure 4]
Figure 4
The mol­ecule of 1 showing all six penta­flourophen­oxy rings leaning to one side with respect to the central cyclo­triphosphazene moiety.

3. Supra­molecular features

With no hydrogen atom in the mol­ecule of 1, hydrogen bonding is not feasible in that structure (see packing diagram in Fig. 5[link]). The mol­ecules nestle along the a-axis direction, with two adjacent rows facing in one direction and the other two in the opposite direction (Fig. 6[link]). A weak parallel-displaced ππ ring inter­action is observed between rings related by inversion symmetry [C25–C30, centroid–centroid distance = 4.030 (2) Å, slippage = 2.22 Å].

[Figure 5]
Figure 5
Packing diagram for 1 viewed down b-axis direction.
[Figure 6]
Figure 6
Unit-cell contents of 1 viewed down the c-axis direction, showing the nestling of the mol­ecules. The top two rows face opposite to the bottom two rows.

In the extended structure of 2, the mol­ecules form chains linked by C—H(π)⋯F type hydrogen bonds (Table 1[link], Fig. 7[link]), along the b-axis direction. Pairs of centrosymmetrically related mol­ecules inter­act with cyclic hydrogen bonds. No ππ ring inter­actions are seen in this structure.

Table 1
Hydrogen-bond geometry (Å, °) for (2)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯F7Ai 0.93 2.64 3.475 (14) 149
C13—H13⋯F7Bi 0.93 2.52 3.316 (11) 144
C37—H37⋯F7Aii 0.93 2.33 3.149 (8) 146
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z.
[Figure 7]
Figure 7
Packing diagram for 2 viewed along the a-axis direction. The dashed lines show inter­molecular C—H⋯F inter­actions – red ones for cyclic inter­actions between mol­ecules straddling the inversion center and the green for inter­actions generating continuous chains along the b-axis direction.

The packing diagram of 3 shows mol­ecules linked by C—H(π)⋯F hydrogen bonds (Table 2[link], Fig. 8[link]), forming chains propagating along the a and b-axis directions. In addition, pairs of mol­ecules related by inversion centers have cyclic hydrogen bonding between them. A parallel ππ stacking inter­action is observed between one of the six phen­oxy rings and its symmetry mate [C41–C46, centroid–centroid distance = 3.646 (2) Å, slippage 1.013 Å].

Table 2
Hydrogen-bond geometry (Å, °) for (3)[link]

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10⋯F26 0.93 2.58 3.478 (10) 163
C30—H30⋯F6Ai 0.93 2.69 3.379 (14) 132
C36—H36⋯F32Aii 0.93 2.59 3.40 (2) 146
C44—H44⋯F29iii 0.93 2.67 3.521 (13) 152
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) -x+1, -y+1, -z.
[Figure 8]
Figure 8
Packing diagram for 3 viewed along the a-axis direction. The black dashed lines show intra­molecular C—H⋯F inter­actions, while the red ones show cyclic inter­action between mol­ecules straddling the inversion center. The green lines are for inter­actions leading to continuous chains along a- and b-axis directions.

Solvent-accessible voids are not present in any of the structures reported here. The solvent inclusion or lack thereof in the crystals of cyclo­triphosphazene compounds has been discussed by Wahl et al. (2016[Wahl, H., Haynes, D. A. & Le Roex, T. (2016). S. Afr. J. Chem. 69, 35-43.]).

4. Database survey

Earlier, we reported the crystal structures of a number of cyclo­triphosphazenes with spiro­cyclic ar­yloxy side groups (Lee et al., 2010[Lee, D. K. Y., Jackson, A. S., Fushimi, T., Yennawar, H. P. & Allcock, H. R. (2010). Dalton Trans. 39, 5341-5348.]). These are clathrate systems that trap hydro­carbon mol­ecules in the cage or tunnel structures. However, the structures in the present study, as well as a series of polymorph structures of hexa­kis­(4-fluoro­phen­oxy) cyclo­triphosphazene reported by Wahl et al. (2016[Wahl, H., Haynes, D. A. & Le Roex, T. (2016). S. Afr. J. Chem. 69, 35-43.]) have no solvent-accessible voids. Various cyclo­triphosphazene structures have been reported in the literature: [(NPCl2)3, CSD refcode KAGKUY: Bullen, 1971[Bullen, G. J. (1971). J. Chem. Soc. A, pp. 1450-1453.]; (NPF2)3, VARYES02: Singh et al., 2000[Singh, R. P., Vij, A., Kirchmeier, R. L. & Shreeve, J. M. (2000). Inorg. Chem. 39, 375-377.]; (NPPh2)3·THF, GUHPII: Dietrich et al., 2000[Dietrich, A., Neumüller, B. & Dehnicke, K. (2000). Z. Anorg. Allg. Chem. 626, 2035-2037.]]. For a review of the expanding field of polyphosphazene high polymers, see: Allcock (2016[Allcock, H. R. (2016). Dalton Trans. 45, 1856-1862.]).

5. Synthesis and crystallization

Synthesis of hexa­kis­(penta­fluoro­phen­oxy)cyclo­triphos­pha­zene (1):

Sodium penta­fluoro­phenoxide was prepared by the treatment of penta­fluoro­phenol (15.88 g, 86 mmol) with a suspension of NaH 60% dispersion in mineral oil (3.10 g, 78 mmol) in 50 ml of dioxane. The penta­fluoro­phenoxide was added to a stirred solution of hexa­chloro­cyclo­triphosphazene (3.00 g, 8.6 mmol) and the mixture was heated at reflux for 3 d. Dioxane was removed from the mixture by rotary evaporation and the residue was dissolved in 100 ml di­chloro­methane. The solution was extracted with 3 × 100 ml of deionized water, dried over MgSO4, and concentrated to ∼10 ml by rotary evaporation. A small amount of hexa­nes was added to the concentrated solution and it was chilled to 273 K via an ice bath to yield colorless blocks of 1, which were filtered and rinsed with cold hexa­nes then dried under vacuum.

Synthesis of hexa­kis­(4-tri­fluoro­methyl­phen­oxy)cyclo­tri­phos­phazene (2):

The aryl­oxide was prepared by treatment of 4-tri­fluoro­methyl­phenol (1.63 g, 10 mmol) with a suspension of NaH [60% dispersion in mineral oil (0.39 g, 9.9 mmol)] in 50 ml of THF. To the stirred solution of 4-tri­fluoro­methyl­phenoxide was added a solution of hexa­chloro­cyclo­triphosphazene (0.50 g, 1.4 mmol) in 15 ml of THF and the mixture was stirred at room temperature overnight. The purification steps of this compound were identical to those of compound 1 to yield colorless cubes of 2.

Synthesis of hexa­kis­(3,5-bis-tri­fluoro­methyl­phen­oxy)cyclo­triphosphazene (3):

A stirred suspension of NaH [60% dispersion in mineral oil (0.19 g, 4.9 mmol)] in 25 ml of THF was treated with liquid 3,5-bis-tri­fluoro­methyl­phenol (0.767 ml, 5.0 mmol) by dropwise addition. The resulting aryl­oxide solution was then added to a stirred solution of hexa­chloro­cyclo­triphosphazene (0.25 g, 0.72 mmol) in 25 ml of THF and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated by rotary evaporation and the residue was dissolved in 40 ml di­chloro­methane. The di­chloro­methane solution was washed with 40 ml of deionized water, followed by 20 ml of 5% HCl, and finally rinsed with 40 ml of deionized water. The organic layer was dried over MgSO4 and the di­chloro­methane was removed by rotary evaporation to yield a colorless oil, which crystallized as colorless needles of 3 after standing for several hours. The crystals were rinsed with cold methanol and then dried under vacuum.

The NMR data for 13 are as follows: 1: 31P 10.6 1 ppm (in chloro­form-d); 19F −153.52 (d, 2F), −157.53 (t, 1F), −161.79 (t, 2F); 2: 31P 8.64 ppm (in chloro­form-d); 1H 747(d, 2H), 706 (d 2H); 19F −62.79 (s); 3: 31P 7.71 ppm (in chloro­form-d); 1H 7.74 (s 1H), 7.52 (s, 2H); 19F −63.85 (s).

6. Refinement

Crystal data, data collection and structure refinement details for all three structures are summarized in Table 3[link]. The hydrogen atoms in 2 and 3 were placed geometrically (C—H = 0.93 Å) and refined as riding on their parent atoms with Uiso(H) = 1.2Ueq(C).

Table 3
Experimental details

  (1) (2) (3)
Crystal data
Chemical formula C36F30N3O6P3 C42H24F18N3O6P3 C48H18F36N3O6P3
Mr 1233.30 1101.55 1509.56
Crystal system, space group Monoclinic, P21/c Triclinic, P[\overline{1}] Triclinic, P[\overline{1}]
Temperature (K) 298 298 298
a, b, c (Å) 8.1111 (17), 44.054 (9), 12.259 (2) 13.4906 (11), 13.6573 (11), 14.9377 (13) 8.9782 (14), 13.947 (2), 23.205 (4)
α, β, γ (°) 90, 109.612 (12), 90 65.253 (2), 68.874 (2), 71.715 (2) 97.276 (6), 93.155 (6), 91.615 (6)
V3) 4126.3 (14) 2288.0 (3) 2876.2 (8)
Z 4 2 2
Radiation type Mo Kα Mo Kα Mo Kα
μ (mm−1) 0.33 0.25 0.27
Crystal size (mm) 0.22 × 0.09 × 0.07 0.28 × 0.23 × 0.22 0.18 × 0.09 × 0.08
 
Data collection
Diffractometer Bruker SMART CCD area detector Bruker SMART CCD area detector Bruker SMART CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.736, 0.9 0.727, 0.9 0.629, 0.9
No. of measured, independent and observed [I > 2σ(I)] reflections 35241, 10189, 6392 21657, 11015, 6744 28557, 14187, 6133
Rint 0.048 0.019 0.046
(sin θ/λ)max−1) 0.667 0.666 0.675
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.153, 1.04 0.062, 0.195, 0.98 0.063, 0.160, 0.95
No. of reflections 10189 11015 14187
No. of parameters 703 817 1201
No. of restraints 0 462 813
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.37, −0.28 0.32, −0.27 0.28, −0.32
Computer programs: SMART and SAINT (Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


Computing details top

For all structures, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Hexakis(pentafluorophenoxy)cyclotriphosphazene (1) top
Crystal data top
C36F30N3O6P3F(000) = 2400
Mr = 1233.30Dx = 1.985 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.1111 (17) ÅCell parameters from 4693 reflections
b = 44.054 (9) Åθ = 2.7–27.8°
c = 12.259 (2) ŵ = 0.33 mm1
β = 109.612 (12)°T = 298 K
V = 4126.3 (14) Å3Block, colorless
Z = 40.22 × 0.09 × 0.07 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
10189 independent reflections
Radiation source: fine-focus sealed tube6392 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
phi and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.736, Tmax = 0.9k = 5850
35241 measured reflectionsl = 1616
Refinement top
Refinement on F2703 parameters
Least-squares matrix: full0 restraints
R[F2 > 2σ(F2)] = 0.065 w = 1/[σ2(Fo2) + (0.0615P)2 + 1.7223P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.153(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.37 e Å3
10189 reflectionsΔρmin = 0.28 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6926 (4)0.09424 (7)1.1812 (3)0.0416 (7)
C20.5803 (4)0.07350 (7)1.2016 (3)0.0470 (8)
C30.5875 (5)0.06715 (8)1.3133 (3)0.0554 (9)
C40.7097 (6)0.08083 (9)1.4052 (3)0.0610 (10)
C50.8280 (5)0.10073 (9)1.3867 (3)0.0573 (9)
C60.8207 (4)0.10717 (8)1.2747 (3)0.0475 (8)
C70.5605 (4)0.17945 (7)1.0959 (3)0.0460 (8)
C80.5722 (5)0.18524 (8)1.2088 (3)0.0497 (8)
C90.4951 (5)0.21051 (8)1.2361 (3)0.0582 (10)
C100.4057 (6)0.23023 (9)1.1506 (4)0.0702 (11)
C110.3920 (6)0.22461 (9)1.0372 (4)0.0736 (12)
C120.4707 (6)0.19951 (9)1.0112 (3)0.0621 (10)
C130.3912 (4)0.07382 (8)0.6439 (3)0.0466 (8)
C140.4062 (5)0.05131 (8)0.7251 (3)0.0494 (8)
C150.3329 (5)0.02319 (9)0.6940 (3)0.0569 (9)
C160.2437 (5)0.01726 (9)0.5794 (4)0.0641 (10)
C170.2247 (5)0.03944 (9)0.4968 (3)0.0618 (10)
C180.2987 (5)0.06757 (8)0.5299 (3)0.0544 (9)
C190.3286 (4)0.16421 (8)0.5883 (3)0.0477 (8)
C200.3597 (5)0.15734 (9)0.4861 (3)0.0546 (9)
C210.2459 (6)0.16755 (11)0.3823 (3)0.0688 (12)
C220.1052 (6)0.18442 (11)0.3783 (4)0.0770 (14)
C230.0725 (5)0.19159 (9)0.4787 (4)0.0701 (12)
C240.1862 (5)0.18160 (8)0.5842 (3)0.0549 (9)
C250.0555 (4)0.06138 (7)0.9107 (3)0.0397 (7)
C260.0353 (4)0.06203 (8)1.0179 (3)0.0484 (8)
C270.0802 (5)0.04288 (9)1.0433 (3)0.0568 (10)
C280.1764 (5)0.02322 (9)0.9628 (4)0.0620 (10)
C290.1628 (5)0.02253 (8)0.8558 (4)0.0613 (10)
C300.0443 (4)0.04154 (8)0.8297 (3)0.0506 (8)
C310.0249 (4)0.15380 (7)0.8629 (3)0.0408 (7)
C320.1235 (4)0.16325 (9)0.7536 (3)0.0540 (9)
C330.1967 (5)0.19206 (10)0.7379 (4)0.0681 (11)
C340.1686 (6)0.21080 (9)0.8302 (5)0.0776 (13)
C350.0736 (6)0.20128 (11)0.9383 (4)0.0848 (14)
C360.0014 (5)0.17292 (9)0.9550 (3)0.0629 (10)
F10.4652 (3)0.05897 (5)1.11273 (18)0.0638 (6)
F20.4764 (3)0.04710 (5)1.3322 (2)0.0827 (7)
F30.7157 (4)0.07480 (6)1.51341 (19)0.0915 (8)
F40.9493 (3)0.11414 (6)1.47566 (18)0.0846 (7)
F50.9380 (3)0.12597 (5)1.25684 (17)0.0677 (6)
F60.6578 (3)0.16612 (5)1.29261 (17)0.0672 (6)
F70.5068 (4)0.21555 (5)1.3460 (2)0.0864 (8)
F80.3293 (4)0.25475 (6)1.1773 (3)0.1067 (9)
F90.3015 (5)0.24383 (6)0.9530 (3)0.1180 (11)
F100.4592 (4)0.19441 (6)0.90053 (19)0.0906 (8)
F110.4950 (3)0.05731 (5)0.83754 (17)0.0646 (6)
F120.3469 (3)0.00219 (5)0.7744 (2)0.0839 (7)
F130.1757 (3)0.01046 (6)0.5482 (2)0.0913 (8)
F140.1356 (4)0.03367 (6)0.3857 (2)0.0911 (8)
F150.2806 (3)0.08866 (5)0.44835 (17)0.0727 (6)
F160.5005 (3)0.14165 (6)0.48793 (17)0.0741 (6)
F170.2745 (4)0.16014 (7)0.28379 (18)0.1002 (9)
F180.0045 (4)0.19480 (7)0.2765 (2)0.1156 (11)
F190.0640 (4)0.20851 (7)0.4760 (3)0.1098 (10)
F200.1589 (3)0.18879 (5)0.6823 (2)0.0692 (6)
F210.1291 (3)0.08154 (6)1.09856 (19)0.0790 (7)
F220.0943 (4)0.04346 (6)1.1492 (2)0.0922 (8)
F230.2883 (4)0.00434 (6)0.9892 (3)0.1051 (10)
F240.2579 (3)0.00299 (7)0.7757 (3)0.1065 (10)
F250.0271 (3)0.03995 (6)0.72509 (18)0.0796 (7)
F260.1516 (3)0.14481 (7)0.66480 (19)0.0926 (8)
F270.2941 (4)0.20106 (7)0.6316 (2)0.1131 (10)
F280.2407 (5)0.23864 (7)0.8134 (3)0.1388 (14)
F290.0517 (5)0.21937 (8)1.0304 (3)0.1567 (17)
F300.0883 (4)0.16350 (7)1.0612 (2)0.1096 (11)
N10.5949 (3)0.12681 (6)0.8763 (2)0.0421 (6)
N20.2484 (3)0.11962 (6)0.7635 (2)0.0423 (6)
N30.3687 (3)0.12301 (6)0.9952 (2)0.0415 (6)
O10.6882 (3)0.10044 (5)1.06885 (17)0.0434 (5)
O20.6489 (3)0.15494 (5)1.07273 (18)0.0477 (5)
O30.4738 (3)0.10159 (5)0.67212 (18)0.0501 (6)
O40.4493 (3)0.15599 (5)0.69450 (17)0.0477 (6)
O50.1827 (3)0.07727 (5)0.8847 (2)0.0520 (6)
O60.0334 (3)0.12420 (5)0.8812 (2)0.0483 (6)
P10.56188 (10)0.12633 (2)0.99536 (6)0.03754 (19)
P20.43660 (11)0.12538 (2)0.75940 (6)0.0398 (2)
P30.21764 (10)0.11254 (2)0.88150 (7)0.0386 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0455 (18)0.0390 (18)0.0401 (16)0.0065 (15)0.0142 (14)0.0016 (13)
C20.0475 (19)0.0378 (18)0.0529 (19)0.0032 (15)0.0133 (15)0.0001 (15)
C30.066 (2)0.040 (2)0.065 (2)0.0042 (18)0.029 (2)0.0117 (17)
C40.085 (3)0.061 (2)0.0419 (19)0.017 (2)0.0273 (19)0.0082 (17)
C50.063 (2)0.062 (2)0.0373 (18)0.005 (2)0.0039 (16)0.0046 (16)
C60.047 (2)0.046 (2)0.0454 (18)0.0015 (16)0.0109 (15)0.0022 (15)
C70.0481 (19)0.0377 (19)0.0521 (19)0.0083 (15)0.0165 (15)0.0020 (15)
C80.054 (2)0.040 (2)0.0547 (19)0.0068 (16)0.0190 (17)0.0011 (16)
C90.075 (3)0.046 (2)0.065 (2)0.0116 (19)0.038 (2)0.0116 (18)
C100.091 (3)0.037 (2)0.094 (3)0.005 (2)0.046 (3)0.006 (2)
C110.101 (3)0.042 (2)0.079 (3)0.011 (2)0.031 (3)0.016 (2)
C120.086 (3)0.046 (2)0.054 (2)0.005 (2)0.023 (2)0.0002 (17)
C130.050 (2)0.048 (2)0.0482 (18)0.0033 (16)0.0245 (15)0.0031 (15)
C140.051 (2)0.056 (2)0.0454 (18)0.0130 (17)0.0211 (15)0.0036 (16)
C150.062 (2)0.049 (2)0.065 (2)0.0109 (18)0.0296 (19)0.0074 (18)
C160.062 (2)0.049 (2)0.087 (3)0.0019 (19)0.033 (2)0.009 (2)
C170.063 (2)0.068 (3)0.056 (2)0.005 (2)0.0223 (19)0.0138 (19)
C180.067 (2)0.056 (2)0.0445 (19)0.0048 (19)0.0246 (17)0.0027 (16)
C190.0469 (19)0.049 (2)0.0431 (17)0.0138 (16)0.0097 (15)0.0085 (15)
C200.052 (2)0.065 (2)0.0438 (18)0.0195 (19)0.0121 (16)0.0061 (16)
C210.066 (3)0.089 (3)0.046 (2)0.033 (2)0.0110 (19)0.014 (2)
C220.073 (3)0.076 (3)0.060 (3)0.023 (2)0.006 (2)0.033 (2)
C230.057 (3)0.051 (2)0.090 (3)0.001 (2)0.009 (2)0.018 (2)
C240.059 (2)0.044 (2)0.062 (2)0.0089 (18)0.0194 (18)0.0084 (17)
C250.0337 (16)0.0350 (17)0.0515 (18)0.0007 (13)0.0157 (14)0.0020 (14)
C260.049 (2)0.047 (2)0.0505 (19)0.0088 (16)0.0181 (16)0.0007 (15)
C270.063 (2)0.056 (2)0.061 (2)0.0210 (19)0.0337 (19)0.0187 (18)
C280.054 (2)0.043 (2)0.103 (3)0.0072 (18)0.045 (2)0.015 (2)
C290.047 (2)0.043 (2)0.091 (3)0.0061 (17)0.019 (2)0.016 (2)
C300.0438 (19)0.057 (2)0.0517 (19)0.0038 (17)0.0164 (16)0.0073 (16)
C310.0313 (16)0.0438 (19)0.0482 (17)0.0016 (14)0.0145 (13)0.0014 (14)
C320.0404 (19)0.064 (2)0.052 (2)0.0008 (17)0.0086 (16)0.0051 (17)
C330.046 (2)0.076 (3)0.072 (3)0.011 (2)0.0061 (19)0.024 (2)
C340.071 (3)0.044 (2)0.108 (4)0.016 (2)0.018 (3)0.004 (2)
C350.085 (3)0.071 (3)0.087 (3)0.022 (3)0.014 (3)0.027 (3)
C360.060 (2)0.068 (3)0.054 (2)0.013 (2)0.0106 (18)0.0071 (19)
F10.0627 (13)0.0517 (13)0.0676 (13)0.0130 (10)0.0094 (11)0.0062 (10)
F20.0933 (18)0.0708 (16)0.0991 (18)0.0122 (13)0.0523 (15)0.0165 (13)
F30.130 (2)0.0991 (19)0.0522 (13)0.0106 (17)0.0400 (14)0.0150 (12)
F40.0969 (18)0.0943 (18)0.0446 (12)0.0045 (15)0.0001 (12)0.0116 (12)
F50.0548 (13)0.0764 (15)0.0632 (13)0.0181 (11)0.0081 (10)0.0023 (11)
F60.0811 (15)0.0679 (14)0.0505 (11)0.0101 (12)0.0195 (11)0.0037 (10)
F70.124 (2)0.0742 (17)0.0773 (15)0.0031 (15)0.0556 (15)0.0204 (12)
F80.145 (3)0.0604 (16)0.131 (2)0.0308 (17)0.068 (2)0.0052 (15)
F90.167 (3)0.0779 (19)0.108 (2)0.0553 (19)0.045 (2)0.0362 (16)
F100.138 (2)0.0800 (17)0.0510 (13)0.0280 (16)0.0274 (14)0.0122 (11)
F110.0714 (14)0.0710 (14)0.0505 (12)0.0135 (11)0.0194 (10)0.0088 (10)
F120.1004 (19)0.0582 (15)0.0973 (18)0.0091 (13)0.0389 (15)0.0250 (13)
F130.0918 (19)0.0572 (16)0.117 (2)0.0105 (13)0.0252 (16)0.0142 (14)
F140.108 (2)0.0894 (19)0.0641 (15)0.0214 (15)0.0137 (14)0.0236 (13)
F150.0969 (17)0.0714 (15)0.0477 (12)0.0055 (13)0.0213 (11)0.0043 (10)
F160.0680 (15)0.1052 (19)0.0565 (12)0.0079 (14)0.0309 (11)0.0023 (12)
F170.0997 (19)0.155 (3)0.0414 (12)0.0437 (18)0.0177 (12)0.0091 (14)
F180.100 (2)0.131 (3)0.0808 (17)0.0171 (18)0.0158 (15)0.0543 (17)
F190.084 (2)0.089 (2)0.138 (3)0.0258 (16)0.0137 (18)0.0305 (18)
F200.0739 (15)0.0547 (13)0.0833 (15)0.0004 (11)0.0322 (12)0.0005 (11)
F210.0782 (16)0.0930 (18)0.0682 (14)0.0034 (13)0.0276 (12)0.0285 (13)
F220.108 (2)0.109 (2)0.0837 (16)0.0342 (16)0.0637 (15)0.0331 (14)
F230.0888 (19)0.0729 (17)0.179 (3)0.0060 (14)0.078 (2)0.0311 (18)
F240.0753 (17)0.101 (2)0.142 (2)0.0374 (16)0.0350 (17)0.0549 (19)
F250.0721 (15)0.109 (2)0.0579 (13)0.0093 (14)0.0224 (11)0.0215 (12)
F260.0747 (16)0.120 (2)0.0586 (13)0.0176 (15)0.0094 (12)0.0294 (14)
F270.092 (2)0.131 (3)0.0925 (19)0.0332 (18)0.0006 (15)0.0503 (18)
F280.125 (3)0.0636 (19)0.202 (4)0.0419 (18)0.021 (2)0.009 (2)
F290.185 (4)0.124 (3)0.129 (3)0.061 (3)0.010 (2)0.068 (2)
F300.129 (2)0.141 (3)0.0469 (13)0.062 (2)0.0131 (14)0.0107 (14)
N10.0348 (14)0.0533 (17)0.0400 (13)0.0002 (12)0.0150 (11)0.0015 (12)
N20.0359 (14)0.0434 (16)0.0436 (14)0.0005 (12)0.0084 (11)0.0010 (11)
N30.0432 (14)0.0477 (16)0.0378 (13)0.0003 (12)0.0191 (11)0.0023 (11)
O10.0445 (12)0.0474 (13)0.0381 (11)0.0057 (10)0.0135 (9)0.0002 (9)
O20.0435 (13)0.0471 (14)0.0503 (13)0.0012 (11)0.0128 (10)0.0058 (10)
O30.0574 (15)0.0533 (15)0.0475 (13)0.0046 (12)0.0280 (11)0.0041 (10)
O40.0497 (13)0.0525 (14)0.0394 (11)0.0095 (11)0.0130 (10)0.0041 (10)
O50.0466 (13)0.0388 (13)0.0809 (16)0.0011 (10)0.0352 (12)0.0006 (11)
O60.0366 (12)0.0435 (13)0.0700 (15)0.0032 (10)0.0246 (11)0.0038 (11)
P10.0361 (4)0.0414 (5)0.0356 (4)0.0004 (4)0.0126 (3)0.0002 (3)
P20.0392 (4)0.0463 (5)0.0348 (4)0.0025 (4)0.0137 (3)0.0017 (3)
P30.0342 (4)0.0372 (5)0.0473 (4)0.0003 (3)0.0174 (3)0.0012 (3)
Geometric parameters (Å, º) top
C1—C21.371 (5)C21—F171.344 (5)
C1—C61.385 (4)C22—C231.380 (6)
C1—O11.392 (3)C22—F181.346 (4)
C2—C31.379 (5)C23—C241.385 (5)
C2—F11.336 (4)C23—F191.326 (5)
C3—C41.366 (5)C24—F201.331 (4)
C3—F21.336 (4)C25—C261.379 (4)
C4—C51.374 (6)C25—C301.365 (4)
C4—F31.337 (4)C25—O51.370 (4)
C5—C61.383 (5)C26—C271.372 (5)
C5—F41.337 (4)C26—F211.338 (4)
C6—F51.334 (4)C27—C281.347 (6)
C7—C81.379 (4)C27—F221.342 (4)
C7—C121.372 (5)C28—C291.354 (6)
C7—O21.378 (4)C28—F231.348 (4)
C8—C91.372 (5)C29—C301.390 (5)
C8—F61.330 (4)C29—F241.338 (4)
C9—C101.367 (6)C30—F251.338 (4)
C9—F71.337 (4)C31—C321.374 (4)
C10—C111.380 (6)C31—C361.369 (5)
C10—F81.340 (4)C31—O61.380 (4)
C11—C121.367 (5)C32—C331.387 (5)
C11—F91.346 (5)C32—F261.315 (4)
C12—F101.347 (4)C33—C341.358 (6)
C13—C141.381 (5)C33—F271.337 (4)
C13—C181.374 (5)C34—C351.357 (6)
C13—O31.382 (4)C34—F281.344 (5)
C14—C151.372 (5)C35—C361.366 (6)
C14—F111.350 (4)C35—F291.343 (5)
C15—C161.372 (5)C36—F301.327 (4)
C15—F121.328 (4)N1—P11.570 (2)
C16—C171.378 (6)N1—P21.572 (3)
C16—F131.342 (4)N2—P21.565 (3)
C17—C181.377 (5)N2—P31.579 (3)
C17—F141.334 (4)N3—P11.573 (3)
C18—F151.336 (4)N3—P31.584 (3)
C19—C201.391 (5)O1—P11.594 (2)
C19—C241.373 (5)O2—P11.593 (2)
C19—O41.389 (4)O3—P21.597 (2)
C20—C211.373 (5)O4—P21.586 (2)
C20—F161.328 (4)O5—P31.582 (2)
C21—C221.349 (6)O6—P31.579 (2)
C2—C1—C6118.8 (3)F19—C23—C24119.4 (4)
C2—C1—O1120.9 (3)C19—C24—C23119.9 (4)
C6—C1—O1120.1 (3)F20—C24—C19119.6 (3)
C1—C2—C3120.5 (3)F20—C24—C23120.5 (4)
F1—C2—C1119.7 (3)C30—C25—C26118.3 (3)
F1—C2—C3119.8 (3)C30—C25—O5117.9 (3)
C4—C3—C2120.5 (3)O5—C25—C26123.4 (3)
F2—C3—C2120.0 (3)C27—C26—C25120.8 (3)
F2—C3—C4119.6 (3)F21—C26—C25119.8 (3)
C3—C4—C5119.9 (3)F21—C26—C27119.4 (3)
F3—C4—C3120.4 (4)C28—C27—C26120.1 (3)
F3—C4—C5119.8 (4)F22—C27—C26119.6 (4)
C4—C5—C6119.7 (3)F22—C27—C28120.3 (4)
F4—C5—C4120.7 (3)C27—C28—C29120.6 (3)
F4—C5—C6119.6 (4)C27—C28—F23119.5 (4)
C5—C6—C1120.5 (3)F23—C28—C29119.9 (4)
F5—C6—C1119.9 (3)C28—C29—C30119.8 (3)
F5—C6—C5119.7 (3)F24—C29—C28120.7 (4)
C12—C7—C8118.8 (3)F24—C29—C30119.5 (4)
C12—C7—O2122.0 (3)C25—C30—C29120.4 (3)
O2—C7—C8119.1 (3)F25—C30—C25120.2 (3)
C9—C8—C7120.7 (3)F25—C30—C29119.4 (3)
F6—C8—C7120.0 (3)C32—C31—O6120.0 (3)
F6—C8—C9119.2 (3)C36—C31—C32119.5 (3)
C10—C9—C8119.8 (3)C36—C31—O6120.1 (3)
F7—C9—C8119.8 (4)C31—C32—C33119.6 (3)
F7—C9—C10120.5 (4)F26—C32—C31120.2 (3)
C9—C10—C11120.1 (4)F26—C32—C33120.2 (3)
F8—C10—C9119.7 (4)C34—C33—C32119.8 (4)
F8—C10—C11120.3 (4)F27—C33—C32119.5 (4)
C12—C11—C10119.6 (4)F27—C33—C34120.7 (4)
F9—C11—C10119.9 (4)C35—C34—C33120.5 (4)
F9—C11—C12120.5 (4)F28—C34—C33119.0 (4)
C11—C12—C7121.0 (3)F28—C34—C35120.5 (4)
F10—C12—C7119.7 (3)C34—C35—C36120.2 (4)
F10—C12—C11119.3 (3)F29—C35—C34120.6 (4)
C14—C13—O3122.5 (3)F29—C35—C36119.2 (4)
C18—C13—C14118.4 (3)C35—C36—C31120.4 (4)
C18—C13—O3119.0 (3)F30—C36—C31119.7 (3)
C15—C14—C13121.5 (3)F30—C36—C35119.9 (4)
F11—C14—C13118.9 (3)P1—N1—P2120.34 (16)
F11—C14—C15119.6 (3)P2—N2—P3121.16 (16)
C14—C15—C16119.1 (3)P1—N3—P3120.25 (15)
F12—C15—C14120.1 (3)C1—O1—P1119.83 (18)
F12—C15—C16120.8 (4)C7—O2—P1125.9 (2)
C15—C16—C17120.5 (4)C13—O3—P2124.36 (19)
F13—C16—C15119.3 (4)C19—O4—P2123.23 (19)
F13—C16—C17120.1 (4)C25—O5—P3131.5 (2)
C18—C17—C16119.4 (3)C31—O6—P3125.49 (19)
F14—C17—C16120.2 (4)N1—P1—N3118.74 (13)
F14—C17—C18120.3 (4)N1—P1—O1104.91 (13)
C13—C18—C17121.0 (3)N1—P1—O2111.30 (13)
F15—C18—C13120.5 (3)N3—P1—O1112.64 (13)
F15—C18—C17118.5 (3)N3—P1—O2108.43 (13)
C24—C19—C20119.6 (3)O2—P1—O199.06 (12)
C24—C19—O4119.9 (3)N1—P2—O3110.92 (14)
O4—C19—C20120.2 (3)N1—P2—O4104.64 (13)
C21—C20—C19119.6 (4)N2—P2—N1118.94 (13)
F16—C20—C19120.8 (3)N2—P2—O3108.71 (13)
F16—C20—C21119.5 (3)N2—P2—O4112.47 (13)
C22—C21—C20120.8 (4)O4—P2—O399.40 (12)
F17—C21—C20119.2 (4)N2—P3—N3115.79 (13)
F17—C21—C22120.0 (4)N2—P3—O5107.53 (13)
C21—C22—C23120.4 (4)N2—P3—O6111.94 (13)
F18—C22—C21120.6 (5)O5—P3—N3110.87 (14)
F18—C22—C23119.0 (5)O6—P3—N3111.06 (13)
C22—C23—C24119.6 (4)O6—P3—O598.18 (12)
F19—C23—C22121.0 (4)
C1—C2—C3—C41.7 (5)C33—C34—C35—F29177.3 (5)
C1—C2—C3—F2179.4 (3)C34—C35—C36—C310.3 (7)
C1—O1—P1—N1179.4 (2)C34—C35—C36—F30178.6 (4)
C1—O1—P1—N350.1 (3)C36—C31—C32—C330.5 (5)
C1—O1—P1—O264.3 (2)C36—C31—C32—F26177.9 (3)
C2—C1—C6—C54.1 (5)C36—C31—O6—P393.0 (4)
C2—C1—C6—F5175.9 (3)F1—C2—C3—C4177.1 (3)
C2—C1—O1—P188.8 (3)F1—C2—C3—F21.8 (5)
C2—C3—C4—C50.9 (6)F2—C3—C4—C5178.0 (3)
C2—C3—C4—F3179.5 (3)F2—C3—C4—F31.6 (6)
C3—C4—C5—C61.0 (6)F3—C4—C5—C6179.4 (3)
C3—C4—C5—F4179.5 (3)F3—C4—C5—F40.1 (6)
C4—C5—C6—C11.5 (5)F4—C5—C6—C1178.0 (3)
C4—C5—C6—F5178.5 (3)F4—C5—C6—F52.0 (5)
C6—C1—C2—C34.2 (5)F6—C8—C9—C10179.6 (3)
C6—C1—C2—F1174.6 (3)F6—C8—C9—F70.1 (5)
C6—C1—O1—P196.5 (3)F7—C9—C10—C11179.0 (4)
C7—C8—C9—C100.1 (6)F7—C9—C10—F80.0 (6)
C7—C8—C9—F7179.4 (3)F8—C10—C11—C12179.9 (4)
C7—O2—P1—N1107.8 (3)F8—C10—C11—F90.0 (7)
C7—O2—P1—N324.5 (3)F9—C11—C12—C7178.7 (4)
C7—O2—P1—O1142.2 (2)F9—C11—C12—F101.0 (7)
C8—C7—C12—C110.9 (6)F11—C14—C15—C16179.7 (3)
C8—C7—C12—F10179.4 (3)F11—C14—C15—F121.1 (5)
C8—C7—O2—P1117.5 (3)F12—C15—C16—C17177.9 (4)
C8—C9—C10—C110.5 (6)F12—C15—C16—F132.5 (6)
C8—C9—C10—F8179.5 (4)F13—C16—C17—C18178.5 (3)
C9—C10—C11—C121.1 (7)F13—C16—C17—F141.4 (6)
C9—C10—C11—F9178.9 (4)F14—C17—C18—C13179.8 (3)
C10—C11—C12—C71.3 (7)F14—C17—C18—F150.7 (6)
C10—C11—C12—F10179.0 (4)F16—C20—C21—C22177.7 (4)
C12—C7—C8—C90.3 (5)F16—C20—C21—F173.3 (5)
C12—C7—C8—F6179.7 (3)F17—C21—C22—C23178.6 (4)
C12—C7—O2—P167.1 (4)F17—C21—C22—F182.2 (6)
C13—C14—C15—C160.5 (5)F18—C22—C23—C24178.6 (3)
C13—C14—C15—F12178.8 (3)F18—C22—C23—F190.2 (6)
C13—O3—P2—N1108.2 (3)F19—C23—C24—C19179.6 (3)
C13—O3—P2—N224.3 (3)F19—C23—C24—F200.2 (5)
C13—O3—P2—O4142.1 (2)F21—C26—C27—C28179.6 (3)
C14—C13—C18—C171.0 (5)F21—C26—C27—F221.6 (5)
C14—C13—C18—F15179.9 (3)F22—C27—C28—C29180.0 (3)
C14—C13—O3—P262.3 (4)F22—C27—C28—F230.7 (5)
C14—C15—C16—C171.3 (6)F23—C28—C29—C30178.5 (3)
C14—C15—C16—F13178.2 (3)F23—C28—C29—F240.8 (6)
C15—C16—C17—C181.1 (6)F24—C29—C30—C25179.2 (3)
C15—C16—C17—F14179.0 (3)F24—C29—C30—F250.1 (5)
C16—C17—C18—C130.1 (6)F26—C32—C33—C34179.2 (4)
C16—C17—C18—F15179.2 (3)F26—C32—C33—F270.8 (6)
C18—C13—C14—C150.7 (5)F27—C33—C34—C35178.2 (4)
C18—C13—C14—F11179.2 (3)F27—C33—C34—F280.1 (7)
C18—C13—O3—P2121.5 (3)F28—C34—C35—C36179.7 (4)
C19—C20—C21—C220.7 (6)F28—C34—C35—F290.8 (8)
C19—C20—C21—F17178.3 (3)F29—C35—C36—C31178.6 (4)
C19—O4—P2—N1177.7 (2)F29—C35—C36—F300.3 (7)
C19—O4—P2—N247.3 (3)O1—C1—C2—C3178.9 (3)
C19—O4—P2—O367.6 (3)O1—C1—C2—F10.1 (5)
C20—C19—C24—C231.5 (5)O1—C1—C6—C5178.9 (3)
C20—C19—C24—F20178.4 (3)O1—C1—C6—F51.1 (5)
C20—C19—O4—P294.2 (3)O2—C7—C8—C9175.9 (3)
C20—C21—C22—C230.4 (6)O2—C7—C8—F64.7 (5)
C20—C21—C22—F18178.9 (3)O2—C7—C12—C11176.4 (4)
C21—C22—C23—C240.6 (6)O2—C7—C12—F103.9 (6)
C21—C22—C23—F19179.0 (4)O3—C13—C14—C15175.6 (3)
C22—C23—C24—C191.2 (6)O3—C13—C14—F114.6 (5)
C22—C23—C24—F20178.7 (3)O3—C13—C18—C17175.4 (3)
C24—C19—C20—C211.2 (5)O3—C13—C18—F153.7 (5)
C24—C19—C20—F16177.1 (3)O4—C19—C20—C21175.2 (3)
C24—C19—O4—P291.9 (3)O4—C19—C20—F163.2 (5)
C25—C26—C27—C280.4 (5)O4—C19—C24—C23175.5 (3)
C25—C26—C27—F22178.4 (3)O4—C19—C24—F204.4 (5)
C25—O5—P3—N2131.9 (3)O5—C25—C26—C27172.0 (3)
C25—O5—P3—N3100.6 (3)O5—C25—C26—F218.0 (5)
C25—O5—P3—O615.7 (3)O5—C25—C30—C29173.3 (3)
C26—C25—C30—C290.1 (5)O5—C25—C30—F255.8 (5)
C26—C25—C30—F25179.2 (3)O6—C31—C32—C33173.4 (3)
C26—C25—O5—P363.1 (4)O6—C31—C32—F265.0 (5)
C26—C27—C28—C291.3 (6)O6—C31—C36—C35173.7 (4)
C26—C27—C28—F23179.4 (3)O6—C31—C36—F304.7 (5)
C27—C28—C29—C302.2 (6)P1—N1—P2—N27.2 (3)
C27—C28—C29—F24179.9 (4)P1—N1—P2—O3134.30 (18)
C28—C29—C30—C251.5 (6)P1—N1—P2—O4119.40 (19)
C28—C29—C30—F25177.6 (3)P1—N3—P3—N225.8 (2)
C30—C25—C26—C271.0 (5)P1—N3—P3—O596.99 (19)
C30—C25—C26—F21179.0 (3)P1—N3—P3—O6154.95 (16)
C30—C25—O5—P3123.8 (3)P2—N1—P1—N32.5 (3)
C31—C32—C33—C340.8 (6)P2—N1—P1—O1129.44 (18)
C31—C32—C33—F27179.2 (3)P2—N1—P1—O2124.38 (18)
C31—O6—P3—N257.9 (3)P2—N2—P3—N321.2 (2)
C31—O6—P3—N373.2 (3)P2—N2—P3—O5103.39 (19)
C31—O6—P3—O5170.6 (2)P2—N2—P3—O6149.87 (17)
C32—C31—C36—C350.8 (6)P3—N2—P2—N15.2 (3)
C32—C31—C36—F30177.6 (3)P3—N2—P2—O3123.00 (18)
C32—C31—O6—P394.2 (3)P3—N2—P2—O4127.94 (17)
C32—C33—C34—C351.8 (7)P3—N3—P1—N114.5 (3)
C32—C33—C34—F28180.0 (4)P3—N3—P1—O1108.68 (18)
C33—C34—C35—C361.6 (8)P3—N3—P1—O2142.74 (17)
Hexakis[4-(trifluoromethyl)phenoxy]cyclotriphosphazene (2) top
Crystal data top
C42H24F18N3O6P3Z = 2
Mr = 1101.55F(000) = 1104
Triclinic, P1Dx = 1.599 Mg m3
a = 13.4906 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.6573 (11) ÅCell parameters from 4888 reflections
c = 14.9377 (13) Åθ = 2.6–21.8°
α = 65.253 (2)°µ = 0.25 mm1
β = 68.874 (2)°T = 298 K
γ = 71.715 (2)°Cubical, colorless
V = 2288.0 (3) Å30.28 × 0.23 × 0.22 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
11015 independent reflections
Radiation source: fine-focus sealed tube6744 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
phi and ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1716
Tmin = 0.727, Tmax = 0.9k = 1718
21657 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.1123P)2 + 0.1708P]
where P = (Fo2 + 2Fc2)/3
11015 reflections(Δ/σ)max < 0.001
817 parametersΔρmax = 0.32 e Å3
462 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
P10.68414 (6)0.84053 (6)0.44920 (5)0.0585 (2)
P20.85174 (6)0.67556 (6)0.50300 (5)0.0552 (2)
P30.87918 (7)0.88917 (7)0.42221 (6)0.0707 (3)
F1A0.4362 (12)0.6424 (16)0.1915 (7)0.160 (5)0.60 (2)
F2A0.3227 (6)0.6559 (12)0.3199 (8)0.145 (4)0.60 (2)
F3A0.4489 (17)0.5186 (7)0.3291 (19)0.227 (8)0.60 (2)
F4A0.394 (3)0.7186 (11)0.9862 (16)0.172 (7)0.50 (4)
F5A0.2833 (10)0.866 (2)0.9482 (15)0.197 (7)0.50 (4)
F6A0.4337 (19)0.864 (2)0.9632 (17)0.183 (8)0.50 (4)
F7A0.763 (2)0.2483 (8)0.3807 (10)0.210 (9)0.559 (18)
F8A0.6714 (9)0.3907 (12)0.3012 (15)0.193 (6)0.559 (18)
F9A0.8252 (12)0.3395 (14)0.2322 (9)0.188 (6)0.559 (18)
F10A0.6296 (14)0.6628 (14)1.0167 (15)0.220 (6)0.58 (3)
F11A0.6584 (13)0.4891 (11)1.0681 (7)0.197 (6)0.58 (3)
F12A0.7777 (10)0.5711 (19)1.0454 (10)0.225 (6)0.58 (3)
F13A1.000 (2)0.6604 (14)0.0487 (11)0.153 (7)0.41 (2)
F14A1.1343 (9)0.731 (3)0.0363 (17)0.187 (10)0.41 (2)
F15A0.983 (2)0.8130 (18)0.0613 (16)0.187 (10)0.41 (2)
F16A0.7615 (13)0.9015 (16)0.9322 (8)0.228 (9)0.521 (18)
F17A0.6226 (7)0.9899 (11)0.8914 (9)0.144 (4)0.521 (18)
F18A0.7373 (15)1.0756 (15)0.8606 (11)0.232 (11)0.521 (18)
O10.65907 (17)0.85648 (17)0.34741 (14)0.0702 (5)
O20.56558 (16)0.87706 (17)0.51083 (15)0.0704 (5)
O30.91515 (14)0.61655 (16)0.42139 (14)0.0636 (5)
O40.86635 (16)0.57561 (16)0.60333 (14)0.0662 (5)
O50.9588 (2)0.9303 (2)0.31223 (17)0.0940 (7)
O60.9062 (2)0.9631 (2)0.46466 (17)0.0881 (7)
N10.72831 (17)0.71653 (18)0.50653 (16)0.0560 (5)
N20.91743 (19)0.7639 (2)0.48024 (19)0.0666 (6)
N30.7578 (2)0.9251 (2)0.41827 (19)0.0720 (7)
C10.6004 (2)0.7960 (3)0.3373 (2)0.0631 (7)
C20.6003 (3)0.8158 (3)0.2394 (2)0.0760 (8)
H20.63760.86760.18460.091*
C30.5447 (3)0.7587 (3)0.2226 (2)0.0848 (10)
H30.54520.77170.15620.102*
C40.4886 (3)0.6825 (3)0.3033 (3)0.0785 (9)
C50.4888 (3)0.6644 (3)0.4011 (2)0.0811 (9)
H50.45030.61370.45600.097*
C60.5446 (3)0.7195 (3)0.4194 (2)0.0769 (9)
H60.54490.70580.48570.092*
C70.4253 (4)0.6231 (5)0.2866 (3)0.1041 (12)
C80.5285 (2)0.8581 (2)0.6156 (2)0.0616 (7)
C90.5845 (3)0.8670 (5)0.6688 (3)0.1203 (17)
H90.65390.88230.63710.144*
C100.5384 (4)0.8532 (5)0.7715 (3)0.1295 (18)
H100.57790.85900.80820.155*
C110.4390 (3)0.8320 (3)0.8189 (3)0.0821 (9)
C120.3834 (4)0.8241 (4)0.7636 (3)0.1165 (15)
H120.31400.80880.79530.140*
C130.4271 (3)0.8381 (4)0.6617 (3)0.1033 (13)
H130.38710.83390.62470.124*
C140.3876 (4)0.8233 (5)0.9270 (3)0.1174 (14)
C150.8713 (2)0.5499 (2)0.40165 (19)0.0560 (6)
C160.8619 (2)0.4457 (2)0.4678 (2)0.0640 (7)
H160.87930.41970.52960.077*
C170.8263 (2)0.3799 (3)0.4419 (2)0.0688 (7)
H170.81950.30880.48650.083*
C180.8004 (3)0.4186 (3)0.3498 (2)0.0697 (7)
C190.8091 (3)0.5248 (3)0.2851 (2)0.0770 (9)
H190.79110.55180.22340.092*
C200.8438 (3)0.5907 (3)0.3109 (2)0.0716 (8)
H200.84880.66250.26750.086*
C210.7667 (4)0.3459 (4)0.3208 (3)0.1023 (12)
C220.8220 (2)0.5822 (2)0.7016 (2)0.0615 (7)
C230.8860 (3)0.5992 (3)0.7438 (3)0.0923 (11)
H230.95560.61180.70640.111*
C240.8460 (4)0.5973 (4)0.8433 (3)0.1145 (14)
H240.88900.60810.87370.137*
C250.7440 (5)0.5799 (4)0.8972 (3)0.1115 (14)
C260.6821 (4)0.5634 (4)0.8531 (3)0.1285 (17)
H260.61230.55130.89010.154*
C270.7209 (3)0.5642 (4)0.7538 (3)0.0996 (12)
H270.67820.55260.72360.119*
C280.7003 (7)0.5779 (6)1.0037 (4)0.177 (3)
C290.9745 (3)0.8835 (3)0.2388 (2)0.0810 (9)
C301.0614 (3)0.8001 (4)0.2282 (3)0.0992 (12)
H301.10730.77250.27060.119*
C311.0793 (3)0.7581 (4)0.1533 (3)0.1006 (12)
H311.13760.70110.14540.121*
C321.0123 (3)0.7991 (3)0.0902 (3)0.0864 (10)
C330.9258 (3)0.8820 (3)0.1029 (3)0.0924 (10)
H330.87960.90990.06070.111*
C340.9067 (3)0.9247 (3)0.1780 (3)0.0898 (10)
H340.84800.98110.18660.108*
C351.0318 (4)0.7530 (4)0.0104 (3)0.1108 (13)
C360.8587 (3)0.9643 (3)0.5638 (2)0.0735 (8)
C370.7719 (4)1.0433 (3)0.5824 (3)0.1078 (13)
H370.74211.09440.52940.129*
C380.7283 (4)1.0481 (4)0.6782 (4)0.1182 (15)
H380.66721.10100.69080.142*
C390.7728 (3)0.9766 (3)0.7557 (3)0.0897 (10)
C400.8609 (4)0.8990 (4)0.7358 (3)0.1053 (12)
H400.89200.84900.78820.126*
C410.9049 (3)0.8930 (4)0.6389 (3)0.0967 (11)
H410.96590.84030.62570.116*
C420.7262 (5)0.9837 (5)0.8593 (4)0.1269 (16)
F1B0.3334 (15)0.6780 (15)0.268 (2)0.214 (10)0.40 (2)
F3B0.4773 (17)0.580 (2)0.2181 (17)0.163 (9)0.40 (2)
F2B0.3929 (15)0.5385 (14)0.3684 (6)0.137 (5)0.40 (2)
F8B0.730 (2)0.3875 (10)0.2449 (11)0.182 (9)0.441 (18)
F7B0.6902 (10)0.2962 (12)0.3998 (9)0.134 (5)0.441 (18)
F9B0.8426 (8)0.2602 (12)0.3094 (17)0.159 (7)0.441 (18)
F14B1.1116 (15)0.6706 (11)0.0104 (12)0.194 (6)0.59 (2)
F15B1.0467 (16)0.8241 (9)0.0802 (6)0.166 (6)0.59 (2)
F13B0.9472 (11)0.7161 (17)0.0203 (13)0.179 (6)0.59 (2)
F18B0.6521 (17)1.0665 (18)0.8675 (12)0.266 (13)0.479 (18)
F16B0.7994 (9)0.9847 (11)0.8964 (8)0.142 (4)0.479 (18)
F17B0.688 (2)0.8961 (17)0.9256 (10)0.250 (14)0.479 (18)
F10B0.685 (3)0.6819 (12)1.0010 (18)0.264 (13)0.42 (3)
F12B0.773 (2)0.523 (3)1.055 (2)0.311 (15)0.42 (3)
F11B0.605 (2)0.542 (3)1.0475 (17)0.282 (11)0.42 (3)
F5B0.3040 (18)0.9045 (19)0.9332 (13)0.182 (7)0.50 (4)
F4B0.351 (3)0.7310 (15)0.9857 (18)0.174 (7)0.50 (4)
F6B0.4543 (15)0.825 (3)0.9713 (13)0.170 (7)0.50 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0639 (4)0.0609 (4)0.0499 (4)0.0100 (3)0.0165 (3)0.0186 (3)
P20.0554 (4)0.0635 (4)0.0488 (4)0.0100 (3)0.0114 (3)0.0246 (3)
P30.0831 (6)0.0789 (6)0.0596 (4)0.0359 (4)0.0091 (4)0.0265 (4)
F1A0.160 (8)0.289 (15)0.108 (4)0.113 (9)0.007 (4)0.113 (6)
F2A0.085 (4)0.265 (10)0.136 (6)0.079 (5)0.007 (4)0.114 (6)
F3A0.282 (17)0.135 (5)0.348 (19)0.057 (7)0.192 (16)0.060 (9)
F4A0.235 (19)0.197 (7)0.067 (6)0.072 (8)0.028 (10)0.017 (5)
F5A0.106 (6)0.326 (19)0.093 (6)0.021 (7)0.023 (4)0.069 (10)
F6A0.184 (12)0.292 (17)0.140 (11)0.100 (12)0.029 (8)0.159 (13)
F7A0.44 (3)0.103 (7)0.163 (10)0.123 (12)0.179 (13)0.015 (7)
F8A0.191 (7)0.216 (10)0.268 (16)0.050 (6)0.137 (9)0.102 (11)
F9A0.304 (12)0.172 (12)0.142 (7)0.084 (10)0.030 (8)0.101 (8)
F10A0.260 (11)0.235 (9)0.117 (8)0.023 (8)0.041 (6)0.111 (8)
F11A0.251 (12)0.247 (9)0.047 (3)0.070 (8)0.019 (5)0.009 (5)
F12A0.318 (10)0.315 (19)0.070 (5)0.098 (9)0.029 (7)0.084 (8)
F13A0.234 (18)0.148 (10)0.112 (7)0.082 (12)0.029 (9)0.059 (6)
F14A0.125 (7)0.33 (3)0.152 (14)0.059 (10)0.029 (7)0.173 (17)
F15A0.28 (2)0.190 (14)0.132 (14)0.022 (13)0.120 (16)0.083 (9)
F16A0.236 (15)0.33 (2)0.087 (6)0.027 (13)0.049 (8)0.061 (10)
F17A0.136 (5)0.196 (10)0.123 (6)0.061 (6)0.017 (4)0.098 (7)
F18A0.29 (2)0.318 (18)0.198 (12)0.195 (17)0.067 (11)0.201 (13)
O10.0840 (13)0.0768 (13)0.0509 (10)0.0240 (11)0.0214 (9)0.0138 (9)
O20.0665 (12)0.0786 (13)0.0612 (11)0.0021 (10)0.0210 (9)0.0279 (10)
O30.0581 (11)0.0783 (13)0.0607 (11)0.0154 (9)0.0065 (8)0.0361 (10)
O40.0727 (12)0.0677 (12)0.0575 (11)0.0011 (9)0.0217 (9)0.0262 (9)
O50.1126 (18)0.1132 (18)0.0669 (13)0.0661 (15)0.0019 (12)0.0309 (13)
O60.1099 (17)0.0967 (16)0.0781 (14)0.0568 (14)0.0081 (12)0.0366 (13)
N10.0575 (12)0.0606 (13)0.0489 (11)0.0162 (10)0.0093 (9)0.0185 (10)
N20.0619 (14)0.0812 (16)0.0677 (14)0.0205 (12)0.0142 (11)0.0335 (12)
N30.0925 (18)0.0583 (14)0.0669 (15)0.0211 (13)0.0246 (13)0.0157 (12)
C10.0589 (16)0.0769 (19)0.0531 (14)0.0079 (14)0.0158 (12)0.0249 (14)
C20.081 (2)0.096 (2)0.0493 (15)0.0209 (17)0.0143 (14)0.0228 (16)
C30.079 (2)0.124 (3)0.0612 (18)0.019 (2)0.0161 (16)0.0440 (19)
C40.0644 (18)0.109 (3)0.0738 (19)0.0169 (17)0.0128 (15)0.0473 (19)
C50.078 (2)0.106 (3)0.0636 (18)0.0318 (19)0.0124 (15)0.0278 (18)
C60.081 (2)0.103 (2)0.0524 (15)0.0294 (18)0.0194 (14)0.0226 (16)
C70.095 (3)0.153 (4)0.091 (3)0.043 (3)0.017 (2)0.061 (3)
C80.0598 (16)0.0628 (16)0.0622 (15)0.0025 (13)0.0154 (12)0.0288 (14)
C90.085 (2)0.225 (5)0.085 (2)0.069 (3)0.0042 (19)0.079 (3)
C100.101 (3)0.235 (6)0.092 (3)0.066 (3)0.003 (2)0.087 (3)
C110.082 (2)0.094 (2)0.0700 (19)0.0173 (18)0.0098 (16)0.0356 (18)
C120.098 (3)0.173 (4)0.095 (3)0.073 (3)0.012 (2)0.060 (3)
C130.096 (3)0.151 (4)0.088 (2)0.055 (3)0.008 (2)0.055 (3)
C140.110 (3)0.157 (4)0.080 (3)0.029 (3)0.005 (2)0.050 (3)
C150.0507 (14)0.0674 (17)0.0497 (13)0.0070 (12)0.0079 (11)0.0277 (13)
C160.0671 (17)0.0760 (19)0.0465 (14)0.0122 (14)0.0157 (12)0.0195 (13)
C170.081 (2)0.0674 (18)0.0551 (15)0.0225 (15)0.0184 (14)0.0124 (14)
C180.0765 (19)0.078 (2)0.0614 (16)0.0232 (15)0.0194 (14)0.0234 (15)
C190.102 (2)0.081 (2)0.0543 (16)0.0210 (18)0.0329 (16)0.0164 (15)
C200.094 (2)0.0670 (18)0.0544 (16)0.0190 (16)0.0221 (15)0.0163 (14)
C210.140 (4)0.100 (3)0.088 (3)0.046 (3)0.043 (3)0.026 (2)
C220.0718 (18)0.0610 (16)0.0487 (14)0.0078 (13)0.0186 (12)0.0173 (12)
C230.085 (2)0.130 (3)0.076 (2)0.023 (2)0.0173 (17)0.051 (2)
C240.144 (4)0.140 (4)0.077 (2)0.016 (3)0.039 (2)0.053 (3)
C250.147 (4)0.103 (3)0.0523 (19)0.003 (3)0.016 (2)0.0240 (19)
C260.109 (3)0.160 (5)0.073 (3)0.046 (3)0.016 (2)0.019 (3)
C270.093 (3)0.135 (3)0.070 (2)0.052 (2)0.0109 (18)0.022 (2)
C280.246 (7)0.166 (5)0.063 (3)0.008 (5)0.018 (4)0.040 (4)
C290.088 (2)0.099 (2)0.0555 (17)0.047 (2)0.0005 (15)0.0222 (17)
C300.078 (2)0.142 (4)0.070 (2)0.027 (2)0.0080 (17)0.034 (2)
C310.086 (2)0.120 (3)0.074 (2)0.012 (2)0.0026 (18)0.035 (2)
C320.093 (2)0.097 (3)0.0602 (18)0.029 (2)0.0028 (17)0.0261 (18)
C330.107 (3)0.100 (3)0.067 (2)0.019 (2)0.0254 (19)0.0249 (19)
C340.101 (3)0.088 (2)0.072 (2)0.016 (2)0.0161 (19)0.0269 (18)
C350.137 (4)0.112 (3)0.080 (3)0.031 (3)0.012 (3)0.039 (2)
C360.089 (2)0.072 (2)0.0759 (19)0.0342 (17)0.0187 (17)0.0303 (16)
C370.146 (4)0.082 (2)0.095 (3)0.005 (2)0.049 (3)0.036 (2)
C380.142 (4)0.106 (3)0.111 (3)0.018 (3)0.047 (3)0.060 (3)
C390.099 (3)0.108 (3)0.088 (2)0.025 (2)0.0249 (19)0.054 (2)
C400.120 (3)0.119 (3)0.096 (3)0.008 (3)0.054 (2)0.044 (2)
C410.094 (3)0.114 (3)0.104 (3)0.002 (2)0.042 (2)0.058 (2)
C420.141 (4)0.161 (5)0.106 (3)0.038 (4)0.024 (3)0.072 (3)
F1B0.167 (12)0.232 (12)0.33 (3)0.020 (11)0.176 (16)0.135 (15)
F3B0.156 (12)0.238 (19)0.158 (12)0.112 (12)0.047 (10)0.148 (13)
F2B0.168 (11)0.200 (11)0.090 (6)0.117 (9)0.015 (5)0.049 (5)
F8B0.37 (3)0.116 (9)0.146 (10)0.088 (12)0.183 (15)0.000 (7)
F7B0.155 (8)0.147 (10)0.138 (7)0.097 (7)0.006 (5)0.064 (7)
F9B0.174 (8)0.137 (11)0.224 (18)0.012 (7)0.062 (9)0.122 (13)
F14B0.259 (12)0.146 (9)0.168 (11)0.043 (8)0.063 (9)0.099 (8)
F15B0.294 (15)0.135 (6)0.060 (3)0.081 (8)0.006 (6)0.032 (3)
F13B0.226 (10)0.218 (14)0.144 (10)0.109 (10)0.013 (7)0.094 (10)
F18B0.282 (19)0.34 (2)0.183 (15)0.165 (17)0.127 (15)0.200 (17)
F16B0.185 (8)0.184 (10)0.105 (6)0.033 (7)0.067 (6)0.072 (7)
F17B0.39 (3)0.30 (2)0.102 (8)0.23 (2)0.049 (14)0.094 (11)
F10B0.42 (3)0.224 (10)0.096 (9)0.018 (13)0.003 (17)0.101 (9)
F12B0.50 (2)0.31 (3)0.124 (12)0.02 (2)0.163 (17)0.077 (14)
F11B0.356 (18)0.27 (3)0.084 (11)0.09 (2)0.098 (11)0.052 (13)
F5B0.174 (11)0.214 (11)0.104 (8)0.054 (9)0.005 (7)0.098 (8)
F4B0.191 (15)0.198 (9)0.090 (8)0.080 (9)0.024 (8)0.031 (6)
F6B0.152 (8)0.299 (18)0.079 (5)0.060 (9)0.011 (5)0.089 (9)
Geometric parameters (Å, º) top
P1—O11.588 (2)C13—H130.9300
P1—O21.574 (2)C14—F5B1.317 (10)
P1—N11.574 (2)C14—F4B1.325 (12)
P1—N31.574 (3)C14—F6B1.302 (11)
P2—O31.5829 (18)C15—C161.364 (4)
P2—O41.575 (2)C15—C201.373 (4)
P2—N11.570 (2)C16—H160.9300
P2—N21.570 (2)C16—C171.373 (4)
P3—O51.582 (2)C17—H170.9300
P3—O61.577 (2)C17—C181.383 (4)
P3—N21.573 (3)C18—C191.380 (4)
P3—N31.571 (3)C18—C211.471 (5)
F1A—C71.291 (8)C19—H190.9300
F2A—C71.290 (8)C19—C201.365 (4)
F3A—C71.281 (9)C20—H200.9300
F4A—C141.324 (12)C21—F8B1.244 (9)
F5A—C141.319 (12)C21—F7B1.346 (9)
F6A—C141.304 (12)C21—F9B1.318 (9)
F7A—C211.261 (7)C22—C231.356 (4)
F8A—C211.320 (9)C22—C271.345 (5)
F9A—C211.297 (8)C23—H230.9300
F10A—C281.285 (12)C23—C241.378 (5)
F11A—C281.333 (10)C24—H240.9300
F12A—C281.358 (12)C24—C251.358 (7)
F13A—C351.290 (11)C25—C261.350 (7)
F14A—C351.307 (10)C25—C281.477 (6)
F15A—C351.297 (11)C26—H260.9300
F16A—C421.300 (11)C26—C271.380 (6)
F17A—C421.291 (9)C27—H270.9300
F18A—C421.317 (10)C28—F10B1.355 (13)
O1—C11.391 (3)C28—F12B1.307 (14)
O2—C81.394 (3)C28—F11B1.351 (14)
O3—C151.398 (3)C29—C301.369 (5)
O4—C221.401 (3)C29—C341.350 (5)
O5—C291.412 (4)C30—H300.9300
O6—C361.391 (4)C30—C311.377 (6)
C1—C21.371 (4)C31—H310.9300
C1—C61.384 (4)C31—C321.368 (5)
C2—H20.9300C32—C331.368 (5)
C2—C31.379 (5)C32—C351.478 (5)
C3—H30.9300C33—H330.9300
C3—C41.376 (5)C33—C341.382 (5)
C4—C51.376 (4)C34—H340.9300
C4—C71.487 (5)C35—F14B1.291 (10)
C5—H50.9300C35—F15B1.282 (8)
C5—C61.372 (4)C35—F13B1.325 (9)
C6—H60.9300C36—C371.356 (5)
C7—F1B1.289 (11)C36—C411.342 (5)
C7—F3B1.272 (10)C37—H370.9300
C7—F2B1.330 (11)C37—C381.359 (6)
C8—C91.337 (5)C38—H380.9300
C8—C131.348 (4)C38—C391.357 (6)
C9—H90.9300C39—C401.358 (6)
C9—C101.385 (5)C39—C421.478 (5)
C10—H100.9300C40—H400.9300
C10—C111.331 (5)C40—C411.379 (5)
C11—C121.354 (5)C41—H410.9300
C11—C141.478 (5)C42—F18B1.269 (10)
C12—H120.9300C42—F16B1.301 (8)
C12—C131.371 (5)C42—F17B1.304 (11)
O2—P1—O198.79 (11)F9A—C21—C18112.4 (6)
O2—P1—N1109.73 (12)F9A—C21—F7B137.9 (6)
O2—P1—N3111.74 (13)F9A—C21—F9B56.9 (7)
N1—P1—O1111.78 (12)F8B—C21—F7A122.5 (7)
N1—P1—N3116.95 (13)F8B—C21—F8A42.3 (9)
N3—P1—O1106.31 (12)F8B—C21—F9A58.0 (8)
O4—P2—O399.42 (11)F8B—C21—C18118.0 (6)
N1—P2—O3111.82 (11)F8B—C21—F7B106.4 (10)
N1—P2—O4109.86 (11)F8B—C21—F9B107.4 (9)
N2—P2—O3106.23 (12)F7B—C21—C18109.2 (6)
N2—P2—O4110.87 (12)F9B—C21—F8A135.6 (7)
N2—P2—N1117.16 (13)F9B—C21—C18113.4 (6)
O6—P3—O594.47 (12)F9B—C21—F7B100.8 (8)
N2—P3—O5111.37 (15)C23—C22—O4118.2 (3)
N2—P3—O6110.74 (13)C27—C22—O4119.7 (3)
N3—P3—O5111.60 (15)C27—C22—C23121.9 (3)
N3—P3—O6110.74 (14)C22—C23—H23120.7
N3—P3—N2115.92 (13)C22—C23—C24118.7 (4)
C1—O1—P1126.59 (18)C24—C23—H23120.7
C8—O2—P1127.04 (18)C23—C24—H24119.8
C15—O3—P2123.62 (15)C25—C24—C23120.4 (4)
C22—O4—P2123.54 (17)C25—C24—H24119.8
C29—O5—P3120.19 (19)C24—C25—C28120.8 (6)
C36—O6—P3123.21 (19)C26—C25—C24119.6 (4)
P2—N1—P1120.25 (14)C26—C25—C28119.6 (6)
P2—N2—P3121.42 (15)C25—C26—H26119.6
P3—N3—P1122.96 (16)C25—C26—C27120.9 (4)
C2—C1—O1116.0 (3)C27—C26—H26119.6
C2—C1—C6120.5 (3)C22—C27—C26118.5 (4)
C6—C1—O1123.4 (2)C22—C27—H27120.7
C1—C2—H2120.1C26—C27—H27120.7
C1—C2—C3119.7 (3)F10A—C28—F11A107.9 (10)
C3—C2—H2120.1F10A—C28—F12A104.0 (12)
C2—C3—H3119.7F10A—C28—C25115.5 (10)
C4—C3—C2120.5 (3)F10A—C28—F10B35.0 (17)
C4—C3—H3119.7F10A—C28—F12B125 (2)
C3—C4—C5118.9 (3)F10A—C28—F11B75.9 (12)
C3—C4—C7121.1 (3)F11A—C28—F12A102.1 (10)
C5—C4—C7120.0 (3)F11A—C28—C25113.2 (8)
C4—C5—H5119.3F11A—C28—F10B135.7 (13)
C6—C5—C4121.4 (3)F11A—C28—F11B38.3 (14)
C6—C5—H5119.3F12A—C28—C25113.0 (8)
C1—C6—H6120.6F10B—C28—F12A77.0 (19)
C5—C6—C1118.8 (3)F10B—C28—C25107.3 (11)
C5—C6—H6120.6F12B—C28—F11A78.3 (18)
F1A—C7—C4114.1 (7)F12B—C28—F12A28 (2)
F1A—C7—F2B129.2 (9)F12B—C28—C25110.9 (13)
F2A—C7—F1A102.6 (8)F12B—C28—F10B103.6 (16)
F2A—C7—C4110.8 (6)F12B—C28—F11B113.7 (15)
F2A—C7—F2B75.3 (9)F11B—C28—F12A130.9 (15)
F3A—C7—F1A106.9 (9)F11B—C28—C25110.6 (10)
F3A—C7—F2A109.0 (10)F11B—C28—F10B110.4 (14)
F3A—C7—C4112.8 (6)C30—C29—O5118.7 (3)
F3A—C7—F1B125.6 (12)C34—C29—O5119.6 (4)
F3A—C7—F2B36.6 (10)C34—C29—C30121.7 (4)
F1B—C7—F1A73.2 (11)C29—C30—H30120.7
F1B—C7—F2A30.5 (13)C29—C30—C31118.6 (4)
F1B—C7—C4116.1 (9)C31—C30—H30120.7
F1B—C7—F2B100.1 (11)C30—C31—H31119.6
F3B—C7—F1A40.2 (11)C32—C31—C30120.8 (4)
F3B—C7—F2A130.7 (11)C32—C31—H31119.6
F3B—C7—F3A70.5 (10)C31—C32—C35120.4 (4)
F3B—C7—C4114.3 (9)C33—C32—C31119.3 (4)
F3B—C7—F1B107.9 (12)C33—C32—C35120.3 (4)
F3B—C7—F2B103.1 (11)C32—C33—H33119.8
F2B—C7—C4113.7 (6)C32—C33—C34120.5 (4)
C9—C8—O2123.6 (3)C34—C33—H33119.8
C9—C8—C13119.7 (3)C29—C34—C33119.2 (4)
C13—C8—O2116.5 (3)C29—C34—H34120.4
C8—C9—H9120.2C33—C34—H34120.4
C8—C9—C10119.6 (4)F13A—C35—F14A104.9 (11)
C10—C9—H9120.2F13A—C35—F15A104.7 (11)
C9—C10—H10119.1F13A—C35—C32111.5 (8)
C11—C10—C9121.7 (4)F13A—C35—F14B67.5 (9)
C11—C10—H10119.1F13A—C35—F13B41.9 (8)
C10—C11—C12117.9 (3)F14A—C35—C32113.0 (8)
C10—C11—C14121.7 (4)F14A—C35—F13B131.9 (10)
C12—C11—C14120.4 (4)F15A—C35—F14A105.7 (10)
C11—C12—H12119.3F15A—C35—C32115.9 (10)
C11—C12—C13121.4 (4)F15A—C35—F13B67.0 (10)
C13—C12—H12119.3F14B—C35—F14A40.0 (9)
C8—C13—C12119.7 (4)F14B—C35—F15A128.0 (11)
C8—C13—H13120.1F14B—C35—C32114.3 (7)
C12—C13—H13120.1F14B—C35—F13B105.0 (9)
F4A—C14—C11109.8 (11)F15B—C35—F13A131.7 (9)
F4A—C14—F4B24.1 (18)F15B—C35—F14A72.7 (11)
F5A—C14—F4A104.6 (12)F15B—C35—F15A38.1 (11)
F5A—C14—C11115.0 (9)F15B—C35—C32113.4 (7)
F5A—C14—F4B81.8 (15)F15B—C35—F14B107.8 (8)
F6A—C14—F4A104.4 (13)F15B—C35—F13B103.1 (9)
F6A—C14—F5A107.2 (12)F13B—C35—C32112.3 (6)
F6A—C14—C11114.7 (10)C37—C36—O6119.8 (3)
F6A—C14—F5B88.1 (15)C41—C36—O6119.6 (3)
F6A—C14—F4B119.4 (19)C41—C36—C37120.3 (3)
F5B—C14—F4A127.7 (15)C36—C37—H37119.9
F5B—C14—F5A26.0 (16)C36—C37—C38120.1 (4)
F5B—C14—C11110.0 (8)C38—C37—H37119.9
F5B—C14—F4B106.6 (11)C37—C38—H38119.6
F4B—C14—C11114.1 (12)C39—C38—C37120.8 (4)
F6B—C14—F4A84.9 (16)C39—C38—H38119.6
F6B—C14—F5A123.9 (14)C38—C39—C40118.5 (4)
F6B—C14—F6A22.5 (19)C38—C39—C42120.5 (4)
F6B—C14—C11112.6 (9)C40—C39—C42121.0 (4)
F6B—C14—F5B109.0 (11)C39—C40—H40119.5
F6B—C14—F4B104.1 (13)C39—C40—C41121.0 (4)
C16—C15—O3120.9 (2)C41—C40—H40119.5
C16—C15—C20121.3 (3)C36—C41—C40119.3 (4)
C20—C15—O3117.6 (3)C36—C41—H41120.4
C15—C16—H16120.4C40—C41—H41120.4
C15—C16—C17119.2 (3)F16A—C42—F18A108.9 (10)
C17—C16—H16120.4F16A—C42—C39116.2 (8)
C16—C17—H17119.8F16A—C42—F16B56.1 (8)
C16—C17—C18120.4 (3)F16A—C42—F17B47.8 (9)
C18—C17—H17119.8F17A—C42—F16A103.3 (9)
C17—C18—C21120.0 (3)F17A—C42—F18A102.6 (8)
C19—C18—C17119.2 (3)F17A—C42—C39113.3 (6)
C19—C18—C21120.8 (3)F17A—C42—F16B134.5 (7)
C18—C19—H19119.7F17A—C42—F17B61.3 (11)
C20—C19—C18120.5 (3)F18A—C42—C39111.3 (7)
C20—C19—H19119.7F18B—C42—F16A127.5 (11)
C15—C20—H20120.3F18B—C42—F17A51.2 (12)
C19—C20—C15119.4 (3)F18B—C42—F18A53.2 (9)
C19—C20—H20120.3F18B—C42—C39116.1 (7)
F7A—C21—F8A107.5 (9)F18B—C42—F16B105.9 (10)
F7A—C21—F9A106.0 (8)F18B—C42—F17B107.5 (12)
F7A—C21—C18118.9 (5)F16B—C42—F18A58.6 (8)
F7A—C21—F7B45.6 (8)F16B—C42—C39112.1 (6)
F7A—C21—F9B55.7 (7)F16B—C42—F17B102.4 (11)
F8A—C21—C18110.4 (6)F17B—C42—F18A136.9 (9)
F8A—C21—F7B70.6 (8)F17B—C42—C39111.7 (8)
F9A—C21—F8A99.8 (8)
P1—O1—C1—C2172.4 (2)C10—C11—C14—F6B8.2 (17)
P1—O1—C1—C67.5 (4)C11—C12—C13—C81.4 (8)
P1—O2—C8—C941.2 (5)C12—C11—C14—F4A82.5 (16)
P1—O2—C8—C13144.0 (3)C12—C11—C14—F5A35.2 (17)
P2—O3—C15—C1675.8 (3)C12—C11—C14—F6A160.3 (16)
P2—O3—C15—C20107.8 (3)C12—C11—C14—F5B62.9 (17)
P2—O4—C22—C2396.7 (3)C12—C11—C14—F4B56.9 (17)
P2—O4—C22—C2787.9 (4)C12—C11—C14—F6B175.3 (16)
P3—O5—C29—C3095.9 (4)C13—C8—C9—C101.4 (7)
P3—O5—C29—C3486.9 (4)C14—C11—C12—C13176.2 (5)
P3—O6—C36—C3796.7 (4)C15—C16—C17—C180.1 (4)
P3—O6—C36—C4189.0 (4)C16—C15—C20—C191.7 (4)
O1—P1—O2—C8164.1 (2)C16—C17—C18—C191.1 (5)
O1—P1—N1—P2105.08 (16)C16—C17—C18—C21177.5 (3)
O1—P1—N3—P3113.22 (18)C17—C18—C19—C200.7 (5)
O1—C1—C2—C3179.5 (3)C17—C18—C21—F7A0.7 (15)
O1—C1—C6—C5179.8 (3)C17—C18—C21—F8A124.2 (10)
O2—P1—O1—C167.0 (2)C17—C18—C21—F9A125.3 (10)
O2—P1—N1—P2146.37 (14)C17—C18—C21—F8B170.1 (14)
O2—P1—N3—P3140.03 (17)C17—C18—C21—F7B48.5 (9)
O2—C8—C9—C10176.0 (4)C17—C18—C21—F9B63.1 (12)
O2—C8—C13—C12176.8 (4)C18—C19—C20—C150.7 (5)
O3—P2—O4—C22178.3 (2)C19—C18—C21—F7A177.9 (14)
O3—P2—N1—P199.69 (16)C19—C18—C21—F8A57.2 (10)
O3—P2—N2—P3102.25 (17)C19—C18—C21—F9A53.2 (11)
O3—C15—C16—C17174.9 (2)C19—C18—C21—F8B11.4 (15)
O3—C15—C20—C19174.7 (3)C19—C18—C21—F7B133.0 (9)
O4—P2—O3—C1579.2 (2)C19—C18—C21—F9B115.4 (11)
O4—P2—N1—P1150.91 (14)C20—C15—C16—C171.3 (4)
O4—P2—N2—P3150.68 (15)C21—C18—C19—C20177.8 (3)
O4—C22—C23—C24175.1 (3)C22—C23—C24—C250.6 (7)
O4—C22—C27—C26175.4 (4)C23—C22—C27—C260.1 (6)
O5—P3—O6—C36179.9 (3)C23—C24—C25—C260.5 (7)
O5—P3—N2—P2111.19 (18)C23—C24—C25—C28179.9 (5)
O5—P3—N3—P1116.65 (19)C24—C25—C26—C270.1 (8)
O5—C29—C30—C31177.0 (3)C24—C25—C28—F10A106.2 (14)
O5—C29—C34—C33176.8 (3)C24—C25—C28—F11A128.8 (9)
O6—P3—O5—C29175.6 (3)C24—C25—C28—F12A13.4 (14)
O6—P3—N2—P2145.06 (16)C24—C25—C28—F10B69 (2)
O6—P3—N3—P1139.50 (18)C24—C25—C28—F12B43 (2)
O6—C36—C37—C38176.9 (4)C24—C25—C28—F11B170.1 (18)
O6—C36—C41—C40176.3 (3)C25—C26—C27—C220.2 (8)
N1—P1—O1—C148.4 (3)C26—C25—C28—F10A74.2 (15)
N1—P1—O2—C847.0 (3)C26—C25—C28—F11A50.8 (10)
N1—P1—N3—P312.4 (2)C26—C25—C28—F12A166.2 (12)
N1—P2—O3—C1536.7 (2)C26—C25—C28—F10B111 (2)
N1—P2—O4—C2260.9 (2)C26—C25—C28—F12B137 (2)
N1—P2—N2—P323.5 (2)C26—C25—C28—F11B9.5 (19)
N2—P2—O3—C15165.6 (2)C27—C22—C23—C240.3 (6)
N2—P2—O4—C2270.2 (2)C28—C25—C26—C27179.7 (5)
N2—P2—N1—P123.3 (2)C29—C30—C31—C320.5 (6)
N2—P3—O5—C2961.3 (3)C30—C29—C34—C330.2 (6)
N2—P3—O6—C3665.3 (3)C30—C31—C32—C330.8 (6)
N2—P3—N3—P112.3 (2)C30—C31—C32—C35179.6 (4)
N3—P1—O1—C1177.2 (2)C31—C32—C33—C340.5 (6)
N3—P1—O2—C884.4 (3)C31—C32—C35—F13A77.2 (15)
N3—P1—N1—P217.8 (2)C31—C32—C35—F14A40.8 (17)
N3—P3—O5—C2970.0 (3)C31—C32—C35—F15A163.1 (18)
N3—P3—O6—C3664.8 (3)C31—C32—C35—F14B3.0 (13)
N3—P3—N2—P217.8 (2)C31—C32—C35—F15B121.1 (11)
C1—C2—C3—C40.5 (5)C31—C32—C35—F13B122.5 (12)
C2—C1—C6—C50.3 (5)C32—C33—C34—C290.0 (6)
C2—C3—C4—C50.0 (5)C33—C32—C35—F13A101.7 (15)
C2—C3—C4—C7177.9 (4)C33—C32—C35—F14A140.4 (16)
C3—C4—C5—C60.8 (5)C33—C32—C35—F15A18.1 (18)
C3—C4—C7—F1A5.8 (12)C33—C32—C35—F14B175.8 (12)
C3—C4—C7—F2A109.5 (7)C33—C32—C35—F15B60.1 (12)
C3—C4—C7—F3A128.1 (15)C33—C32—C35—F13B56.3 (13)
C3—C4—C7—F1B76.6 (17)C34—C29—C30—C310.0 (6)
C3—C4—C7—F3B50.0 (17)C35—C32—C33—C34179.4 (4)
C3—C4—C7—F2B168.0 (10)C36—C37—C38—C392.2 (8)
C4—C5—C6—C10.9 (5)C37—C36—C41—C402.1 (6)
C5—C4—C7—F1A176.4 (10)C37—C38—C39—C401.0 (7)
C5—C4—C7—F2A68.3 (8)C37—C38—C39—C42178.8 (5)
C5—C4—C7—F3A54.1 (15)C38—C39—C40—C410.4 (7)
C5—C4—C7—F1B101.2 (17)C38—C39—C42—F16A168.6 (12)
C5—C4—C7—F3B132.1 (16)C38—C39—C42—F17A49.1 (10)
C5—C4—C7—F2B14.2 (11)C38—C39—C42—F18A65.9 (13)
C6—C1—C2—C30.4 (5)C38—C39—C42—F18B7.6 (18)
C7—C4—C5—C6178.6 (4)C38—C39—C42—F16B129.5 (8)
C8—C9—C10—C110.5 (9)C38—C39—C42—F17B116.2 (16)
C9—C8—C13—C121.8 (7)C39—C40—C41—C361.0 (7)
C9—C10—C11—C120.0 (8)C40—C39—C42—F16A11.6 (14)
C9—C10—C11—C14176.6 (5)C40—C39—C42—F17A131.1 (8)
C10—C11—C12—C130.5 (7)C40—C39—C42—F18A113.8 (12)
C10—C11—C14—F4A100.9 (16)C40—C39—C42—F18B172.2 (17)
C10—C11—C14—F5A141.4 (16)C40—C39—C42—F16B50.2 (9)
C10—C11—C14—F6A16.3 (17)C40—C39—C42—F17B64.1 (16)
C10—C11—C14—F5B113.7 (17)C41—C36—C37—C382.7 (7)
C10—C11—C14—F4B126.6 (17)C42—C39—C40—C41179.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···F7Ai0.932.643.475 (14)149
C13—H13···F7Bi0.932.523.316 (11)144
C37—H37···F7Aii0.932.333.149 (8)146
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z.
Hexakis[3,5-bis(trifluoromethyl)phenoxy]cyclotriphosphazene (3) top
Crystal data top
C48H18F36N3O6P3Z = 2
Mr = 1509.56F(000) = 1488
Triclinic, P1Dx = 1.743 Mg m3
a = 8.9782 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.947 (2) ÅCell parameters from 4291 reflections
c = 23.205 (4) Åθ = 2.3–28.0°
α = 97.276 (6)°µ = 0.27 mm1
β = 93.155 (6)°T = 298 K
γ = 91.615 (6)°Needle, colorless
V = 2876.2 (8) Å30.18 × 0.09 × 0.08 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
6133 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
phi and ω scansθmax = 28.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1211
Tmin = 0.629, Tmax = 0.9k = 1818
28557 measured reflectionsl = 2631
14187 independent reflections
Refinement top
Refinement on F2813 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.160 w = 1/[σ2(Fo2) + (0.0608P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
14187 reflectionsΔρmax = 0.28 e Å3
1201 parametersΔρmin = 0.32 e Å3
Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (30 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.71031 (8)0.68279 (5)0.24145 (3)0.0490 (2)
P20.94354 (8)0.55920 (6)0.22697 (3)0.0517 (2)
P30.83033 (8)0.64836 (6)0.13597 (3)0.0502 (2)
F10.5896 (14)0.3149 (7)0.1837 (4)0.141 (3)0.70 (2)
F1A0.638 (2)0.2998 (19)0.2025 (15)0.168 (11)0.30 (2)
F20.3883 (10)0.2580 (10)0.2101 (7)0.176 (5)0.70 (2)
F2A0.407 (3)0.2829 (19)0.1866 (10)0.125 (7)0.30 (2)
F30.5878 (17)0.2466 (8)0.2585 (4)0.146 (4)0.70 (2)
F3A0.509 (5)0.2257 (13)0.2538 (10)0.168 (11)0.30 (2)
F40.3888 (19)0.5530 (13)0.4454 (5)0.148 (6)0.56 (2)
F4A0.4169 (18)0.5037 (18)0.4526 (6)0.137 (6)0.44 (2)
F50.335 (2)0.4079 (10)0.4299 (8)0.186 (6)0.56 (2)
F5A0.265 (2)0.4013 (10)0.4116 (7)0.142 (6)0.44 (2)
F60.1917 (8)0.5108 (11)0.3996 (6)0.126 (4)0.56 (2)
F6A0.229 (3)0.5491 (16)0.4143 (9)0.178 (8)0.44 (2)
F70.769 (3)0.6724 (9)0.4646 (8)0.175 (9)0.39 (2)
F7A0.8440 (14)0.7015 (10)0.4699 (5)0.158 (5)0.61 (2)
F80.625 (2)0.7553 (14)0.5101 (8)0.173 (7)0.39 (2)
F8A0.6167 (12)0.7081 (11)0.4797 (5)0.181 (6)0.61 (2)
F90.850 (2)0.8013 (16)0.5129 (8)0.210 (9)0.39 (2)
F9A0.7620 (19)0.8100 (6)0.5286 (3)0.166 (5)0.61 (2)
F100.7428 (13)1.1287 (8)0.4067 (9)0.221 (9)0.506 (16)
F10A0.736 (2)1.1168 (8)0.4408 (4)0.203 (7)0.494 (16)
F110.532 (2)1.0946 (8)0.3626 (4)0.179 (7)0.506 (16)
F11A0.6613 (16)1.1202 (5)0.3594 (3)0.117 (4)0.494 (16)
F120.5696 (12)1.0901 (7)0.4511 (3)0.119 (4)0.506 (16)
F12A0.5012 (15)1.0878 (9)0.4176 (11)0.249 (11)0.494 (16)
F131.144 (2)0.1360 (10)0.2463 (5)0.150 (5)0.63 (3)
F13A1.079 (4)0.108 (2)0.2450 (8)0.172 (9)0.37 (3)
F141.2099 (16)0.1545 (10)0.3339 (7)0.171 (5)0.63 (3)
F14A1.2408 (14)0.1559 (16)0.3070 (16)0.159 (9)0.37 (3)
F151.0045 (16)0.0813 (9)0.3040 (9)0.165 (5)0.63 (3)
F15A1.054 (4)0.092 (2)0.3328 (16)0.207 (12)0.37 (3)
F160.7576 (18)0.4766 (8)0.4282 (6)0.122 (5)0.46 (2)
F16A0.860 (3)0.4824 (7)0.4431 (6)0.177 (7)0.54 (2)
F170.7121 (18)0.3375 (7)0.4346 (8)0.160 (7)0.46 (2)
F17A0.6836 (9)0.3799 (16)0.4191 (5)0.179 (6)0.54 (2)
F180.9175 (16)0.400 (2)0.4686 (6)0.191 (10)0.46 (2)
F18A0.8660 (18)0.3414 (10)0.4653 (6)0.143 (5)0.54 (2)
F191.206 (3)0.8001 (8)0.4410 (5)0.241 (11)0.512 (18)
F19A1.1026 (12)0.8208 (11)0.4371 (5)0.142 (5)0.488 (18)
F201.2892 (11)0.9298 (9)0.4176 (6)0.155 (6)0.512 (18)
F20A1.3240 (10)0.855 (2)0.4299 (5)0.227 (10)0.488 (18)
F211.0671 (9)0.9070 (11)0.4103 (6)0.175 (6)0.512 (18)
F21A1.158 (3)0.9509 (7)0.4111 (5)0.257 (12)0.488 (18)
F221.3408 (16)0.9709 (5)0.2188 (6)0.164 (5)0.59 (2)
F22A1.418 (2)0.9417 (18)0.2187 (7)0.215 (10)0.41 (2)
F231.2273 (14)0.8765 (12)0.1532 (5)0.163 (6)0.59 (2)
F23A1.2031 (17)0.9247 (15)0.1795 (9)0.151 (6)0.41 (2)
F241.4405 (12)0.8476 (8)0.1828 (7)0.144 (5)0.59 (2)
F24A1.359 (3)0.8244 (9)0.1555 (7)0.161 (7)0.41 (2)
F250.8228 (17)1.1257 (11)0.1661 (9)0.128 (4)0.53 (4)
F25A0.794 (3)1.1291 (10)0.1456 (14)0.160 (7)0.47 (4)
F260.704 (2)1.0263 (14)0.2078 (5)0.126 (4)0.53 (4)
F26A0.749 (4)1.042 (2)0.2111 (5)0.178 (8)0.47 (4)
F270.5995 (15)1.0915 (14)0.1404 (7)0.153 (5)0.53 (4)
F27A0.5814 (14)1.063 (2)0.1454 (9)0.183 (7)0.47 (4)
F280.9200 (12)0.8697 (11)0.0707 (4)0.149 (6)0.511 (18)
F28A0.8986 (16)0.9588 (14)0.0640 (5)0.182 (9)0.489 (18)
F290.6930 (13)0.8624 (10)0.0749 (5)0.139 (6)0.511 (18)
F29A0.779 (2)0.8274 (7)0.0769 (5)0.174 (9)0.489 (18)
F300.810 (2)0.9971 (6)0.0561 (5)0.151 (7)0.511 (18)
F30A0.6690 (13)0.9550 (13)0.0593 (4)0.174 (7)0.489 (18)
F310.677 (3)0.2591 (9)0.0441 (4)0.223 (9)0.589 (19)
F31A0.5694 (15)0.2066 (15)0.0181 (11)0.201 (11)0.411 (19)
F320.5894 (11)0.1864 (6)0.0201 (7)0.154 (5)0.589 (19)
F32A0.741 (3)0.2175 (16)0.0505 (7)0.248 (13)0.411 (19)
F330.8008 (9)0.2387 (9)0.0304 (7)0.178 (6)0.589 (19)
F33A0.7772 (17)0.2708 (11)0.0240 (9)0.147 (7)0.411 (19)
F340.1976 (12)0.5304 (10)0.0747 (5)0.160 (5)0.590 (17)
F34A0.2342 (16)0.5494 (7)0.1064 (11)0.182 (8)0.410 (17)
F350.1807 (12)0.3807 (9)0.0783 (7)0.180 (6)0.590 (17)
F35A0.1711 (12)0.4226 (12)0.0543 (4)0.105 (4)0.410 (17)
F360.2538 (11)0.4737 (9)0.1496 (3)0.105 (3)0.590 (17)
F36A0.2470 (19)0.4163 (18)0.1385 (7)0.166 (8)0.410 (17)
O10.5523 (2)0.65761 (14)0.26291 (9)0.0599 (5)
O20.7343 (2)0.79123 (13)0.26994 (8)0.0593 (5)
O30.9316 (2)0.44677 (14)0.22645 (9)0.0630 (6)
O41.1042 (2)0.58163 (15)0.25806 (9)0.0615 (6)
O50.9294 (2)0.73185 (14)0.11666 (9)0.0594 (5)
O60.7589 (2)0.60240 (14)0.07457 (8)0.0564 (5)
N10.8278 (2)0.61481 (16)0.26621 (10)0.0498 (6)
N20.9391 (2)0.57664 (16)0.16180 (10)0.0530 (6)
N30.7012 (2)0.68738 (16)0.17451 (9)0.0483 (6)
C10.5120 (3)0.5684 (2)0.28023 (13)0.0520 (7)
C20.5309 (3)0.4829 (2)0.24578 (14)0.0604 (8)
H20.5717720.4828190.2098190.073*
C30.4890 (4)0.3971 (3)0.26466 (15)0.0666 (9)
C40.4240 (4)0.3976 (3)0.31689 (16)0.0736 (9)
H40.3945010.3394700.3293130.088*
C50.4025 (3)0.4834 (3)0.35074 (14)0.0656 (9)
C60.4492 (3)0.5697 (3)0.33279 (13)0.0599 (8)
H60.4379970.6280300.3561750.072*
C70.5120 (6)0.3048 (3)0.2289 (2)0.0945 (12)
C80.3304 (5)0.4854 (4)0.40642 (18)0.0877 (12)
C90.7181 (3)0.8283 (2)0.32754 (13)0.0539 (7)
C100.6842 (3)0.9243 (2)0.33655 (14)0.0625 (8)
H100.6718830.9594720.3052580.075*
C110.6685 (4)0.9678 (2)0.39261 (15)0.0683 (9)
C120.6876 (4)0.9149 (3)0.43872 (16)0.0768 (10)
H120.6791690.9444840.4765790.092*
C130.7190 (4)0.8187 (3)0.42867 (14)0.0703 (9)
C140.7355 (4)0.7751 (2)0.37316 (14)0.0670 (9)
H140.7582670.7101490.3664850.080*
C150.7365 (7)0.7616 (4)0.4775 (2)0.1054 (14)
C160.6333 (7)1.0707 (3)0.4025 (2)0.1070 (14)
C170.9425 (3)0.3935 (2)0.27387 (15)0.0597 (8)
C180.8825 (4)0.4220 (2)0.32527 (15)0.0645 (9)
H180.8352890.4806270.3311630.077*
C190.8917 (4)0.3632 (2)0.36890 (16)0.0687 (9)
C200.9628 (4)0.2765 (3)0.35954 (19)0.0785 (10)
H200.9709210.2372260.3890090.094*
C211.0212 (4)0.2481 (2)0.30702 (19)0.0749 (10)
C221.0130 (3)0.3065 (2)0.26336 (16)0.0697 (9)
H221.0536640.2879750.2278080.084*
C231.0937 (6)0.1547 (3)0.2982 (3)0.1132 (16)
C240.8255 (6)0.3921 (4)0.4240 (2)0.0940 (12)
C251.1517 (3)0.6790 (2)0.27201 (15)0.0596 (8)
C261.2059 (3)0.7289 (3)0.22998 (16)0.0650 (8)
H261.2093540.6991810.1918900.078*
C271.2555 (3)0.8244 (3)0.24508 (18)0.0721 (9)
C281.2502 (4)0.8671 (3)0.30172 (19)0.0819 (10)
H281.2843530.9308600.3119210.098*
C291.1948 (4)0.8161 (3)0.34337 (17)0.0784 (10)
C301.1450 (3)0.7209 (3)0.32856 (15)0.0685 (9)
H301.1076110.6859390.3564590.082*
C311.1911 (7)0.8615 (4)0.4038 (2)0.1192 (16)
C321.3142 (6)0.8783 (4)0.2013 (2)0.1004 (13)
C330.8686 (3)0.8139 (2)0.09617 (14)0.0542 (8)
C340.8614 (3)0.8186 (2)0.03791 (14)0.0608 (8)
H340.8925380.7675560.0121140.073*
C350.8066 (4)0.9013 (3)0.01763 (16)0.0706 (9)
C360.7605 (4)0.9759 (3)0.05658 (18)0.0770 (10)
H360.7227001.0308170.0430190.092*
C370.7700 (4)0.9698 (2)0.11528 (17)0.0705 (9)
C380.8253 (3)0.8876 (2)0.13500 (15)0.0663 (9)
H380.8327970.8828140.1746520.080*
C390.7238 (6)1.0510 (3)0.1561 (2)0.0986 (13)
C400.7993 (6)0.9099 (4)0.04454 (19)0.0989 (13)
C410.6628 (3)0.5212 (2)0.07004 (12)0.0507 (7)
C420.7146 (4)0.4337 (2)0.04778 (13)0.0607 (8)
H420.8139120.4280790.0388360.073*
C430.6176 (4)0.3537 (2)0.03872 (14)0.0671 (9)
C440.4716 (4)0.3614 (3)0.05342 (14)0.0701 (9)
H440.4070810.3072880.0476640.084*
C450.4215 (3)0.4495 (3)0.07666 (13)0.0612 (8)
C460.5169 (3)0.5302 (2)0.08454 (12)0.0584 (8)
H460.4827860.5900610.0995230.070*
C470.2673 (4)0.4588 (3)0.09387 (19)0.0806 (10)
C480.6720 (6)0.2609 (3)0.0117 (3)0.1092 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0555 (5)0.0469 (5)0.0455 (5)0.0113 (4)0.0045 (4)0.0066 (4)
P20.0565 (5)0.0482 (5)0.0515 (5)0.0133 (4)0.0008 (4)0.0089 (4)
P30.0565 (5)0.0504 (5)0.0445 (5)0.0086 (4)0.0028 (4)0.0078 (4)
F10.248 (9)0.081 (4)0.100 (4)0.036 (5)0.071 (5)0.006 (3)
F1A0.123 (10)0.078 (13)0.29 (3)0.009 (8)0.059 (12)0.054 (14)
F20.177 (5)0.128 (7)0.198 (11)0.052 (4)0.004 (5)0.060 (7)
F2A0.162 (13)0.114 (12)0.085 (10)0.016 (10)0.034 (9)0.018 (7)
F30.233 (9)0.068 (5)0.133 (5)0.041 (5)0.017 (5)0.005 (4)
F3A0.33 (3)0.067 (6)0.103 (10)0.013 (13)0.032 (14)0.021 (6)
F40.160 (10)0.228 (11)0.051 (5)0.050 (9)0.027 (5)0.007 (6)
F4A0.122 (6)0.235 (16)0.058 (4)0.008 (9)0.008 (4)0.043 (8)
F50.302 (18)0.173 (9)0.115 (11)0.070 (9)0.084 (10)0.098 (8)
F5A0.177 (11)0.167 (8)0.088 (8)0.068 (8)0.040 (6)0.046 (6)
F60.068 (4)0.222 (9)0.097 (6)0.000 (4)0.034 (3)0.040 (5)
F6A0.211 (14)0.240 (15)0.114 (12)0.140 (13)0.084 (11)0.084 (12)
F70.35 (2)0.104 (7)0.104 (10)0.105 (11)0.122 (13)0.060 (5)
F7A0.217 (9)0.167 (8)0.104 (6)0.100 (7)0.004 (6)0.059 (5)
F80.256 (13)0.213 (15)0.084 (12)0.132 (11)0.103 (10)0.082 (10)
F8A0.237 (8)0.235 (12)0.085 (7)0.056 (8)0.006 (5)0.094 (8)
F90.270 (16)0.292 (16)0.064 (10)0.041 (13)0.064 (11)0.038 (10)
F9A0.315 (14)0.138 (7)0.046 (3)0.045 (7)0.000 (6)0.012 (3)
F100.221 (11)0.083 (5)0.37 (3)0.033 (6)0.113 (10)0.023 (13)
F10A0.436 (18)0.067 (5)0.091 (6)0.054 (7)0.037 (8)0.008 (4)
F110.311 (18)0.092 (7)0.127 (7)0.100 (9)0.036 (9)0.006 (5)
F11A0.207 (10)0.053 (4)0.092 (5)0.026 (5)0.013 (5)0.002 (3)
F120.195 (9)0.073 (5)0.091 (5)0.058 (5)0.043 (4)0.013 (4)
F12A0.258 (11)0.124 (9)0.41 (3)0.115 (9)0.193 (16)0.108 (15)
F130.204 (12)0.084 (7)0.176 (7)0.076 (7)0.060 (7)0.030 (5)
F13A0.22 (2)0.077 (13)0.207 (11)0.052 (12)0.046 (12)0.025 (10)
F140.169 (7)0.164 (7)0.187 (9)0.117 (6)0.011 (6)0.036 (6)
F14A0.106 (6)0.122 (9)0.24 (2)0.051 (7)0.011 (8)0.006 (12)
F150.202 (8)0.057 (4)0.249 (12)0.023 (4)0.048 (7)0.046 (6)
F15A0.24 (2)0.109 (14)0.32 (2)0.097 (12)0.14 (2)0.131 (17)
F160.177 (11)0.087 (6)0.115 (7)0.044 (6)0.068 (8)0.036 (5)
F16A0.286 (18)0.123 (6)0.124 (9)0.003 (8)0.087 (12)0.013 (5)
F170.234 (13)0.093 (6)0.164 (15)0.023 (7)0.120 (11)0.013 (6)
F17A0.101 (5)0.342 (19)0.107 (5)0.046 (7)0.023 (4)0.070 (10)
F180.171 (10)0.33 (3)0.064 (5)0.072 (13)0.012 (6)0.001 (12)
F18A0.188 (10)0.179 (9)0.081 (6)0.061 (7)0.014 (6)0.072 (7)
F190.48 (3)0.170 (8)0.071 (5)0.005 (15)0.032 (15)0.001 (5)
F19A0.159 (8)0.159 (11)0.097 (6)0.026 (6)0.032 (5)0.030 (6)
F200.132 (7)0.171 (11)0.133 (9)0.046 (6)0.015 (6)0.070 (7)
F20A0.141 (6)0.46 (3)0.065 (5)0.047 (10)0.028 (5)0.016 (12)
F210.137 (6)0.205 (13)0.154 (8)0.022 (6)0.043 (5)0.095 (9)
F21A0.52 (3)0.108 (7)0.132 (8)0.014 (14)0.01 (2)0.045 (6)
F220.193 (10)0.070 (4)0.237 (10)0.011 (5)0.097 (7)0.023 (4)
F22A0.202 (15)0.30 (2)0.144 (12)0.178 (15)0.024 (11)0.073 (12)
F230.137 (7)0.232 (14)0.138 (8)0.032 (7)0.006 (6)0.107 (8)
F23A0.167 (9)0.165 (13)0.141 (12)0.024 (7)0.011 (8)0.094 (10)
F240.111 (6)0.156 (9)0.187 (11)0.042 (6)0.070 (6)0.070 (7)
F24A0.178 (16)0.199 (9)0.119 (10)0.001 (10)0.070 (11)0.040 (6)
F250.159 (8)0.096 (6)0.116 (9)0.026 (4)0.022 (5)0.032 (5)
F25A0.281 (16)0.052 (5)0.148 (15)0.006 (6)0.059 (11)0.006 (6)
F260.184 (9)0.096 (9)0.108 (5)0.042 (5)0.068 (5)0.017 (6)
F26A0.36 (2)0.080 (7)0.093 (5)0.037 (12)0.029 (8)0.013 (5)
F270.164 (7)0.110 (8)0.169 (9)0.069 (6)0.046 (9)0.032 (6)
F27A0.151 (7)0.170 (16)0.237 (13)0.083 (8)0.073 (8)0.012 (10)
F280.173 (7)0.200 (14)0.090 (5)0.019 (8)0.043 (5)0.064 (7)
F28A0.185 (11)0.27 (2)0.098 (7)0.132 (13)0.003 (8)0.061 (13)
F290.158 (8)0.160 (12)0.093 (5)0.053 (7)0.053 (6)0.031 (8)
F29A0.33 (3)0.120 (6)0.066 (4)0.047 (8)0.008 (11)0.020 (4)
F300.27 (2)0.100 (5)0.095 (5)0.019 (6)0.022 (9)0.060 (4)
F30A0.177 (9)0.245 (17)0.111 (6)0.033 (10)0.038 (5)0.077 (8)
F310.43 (3)0.110 (9)0.131 (5)0.090 (15)0.093 (11)0.020 (5)
F31A0.176 (9)0.109 (14)0.29 (3)0.036 (9)0.078 (10)0.121 (14)
F320.148 (6)0.051 (3)0.266 (15)0.020 (3)0.033 (7)0.017 (6)
F32A0.40 (3)0.135 (13)0.229 (13)0.159 (19)0.035 (16)0.070 (10)
F330.113 (5)0.106 (7)0.311 (16)0.050 (4)0.044 (6)0.014 (8)
F33A0.149 (10)0.080 (7)0.211 (16)0.024 (6)0.096 (10)0.025 (9)
F340.102 (6)0.267 (11)0.144 (7)0.090 (8)0.053 (5)0.126 (8)
F34A0.109 (9)0.112 (7)0.31 (2)0.004 (6)0.110 (13)0.052 (9)
F350.104 (6)0.200 (8)0.212 (14)0.055 (6)0.056 (7)0.080 (8)
F35A0.053 (4)0.180 (11)0.078 (5)0.005 (6)0.009 (3)0.010 (5)
F360.081 (3)0.177 (8)0.059 (3)0.037 (5)0.020 (2)0.014 (3)
F36A0.121 (7)0.31 (2)0.094 (9)0.015 (13)0.047 (7)0.089 (12)
O10.0539 (12)0.0624 (13)0.0681 (14)0.0181 (10)0.0136 (10)0.0192 (11)
O20.0897 (15)0.0476 (12)0.0408 (12)0.0092 (10)0.0109 (10)0.0017 (9)
O30.0852 (15)0.0487 (13)0.0559 (14)0.0142 (10)0.0007 (11)0.0089 (10)
O40.0564 (12)0.0587 (14)0.0696 (15)0.0184 (10)0.0073 (10)0.0105 (11)
O50.0577 (12)0.0558 (13)0.0669 (14)0.0059 (10)0.0024 (10)0.0160 (11)
O60.0687 (13)0.0608 (13)0.0396 (12)0.0018 (10)0.0028 (10)0.0065 (10)
N10.0526 (13)0.0511 (14)0.0470 (15)0.0135 (11)0.0007 (11)0.0098 (11)
N20.0624 (15)0.0535 (15)0.0448 (15)0.0195 (12)0.0064 (11)0.0077 (12)
N30.0514 (13)0.0556 (15)0.0389 (14)0.0149 (11)0.0014 (10)0.0072 (11)
C10.0498 (16)0.065 (2)0.0440 (18)0.0066 (15)0.0028 (14)0.0183 (16)
C20.0651 (19)0.068 (2)0.049 (2)0.0057 (17)0.0020 (15)0.0092 (17)
C30.076 (2)0.064 (2)0.060 (2)0.0032 (17)0.0021 (17)0.0126 (17)
C40.077 (2)0.077 (2)0.069 (2)0.0079 (19)0.0033 (19)0.025 (2)
C50.0576 (19)0.092 (3)0.051 (2)0.0016 (18)0.0010 (15)0.0239 (19)
C60.0504 (17)0.080 (2)0.050 (2)0.0108 (16)0.0016 (14)0.0122 (17)
C70.127 (4)0.066 (3)0.089 (3)0.006 (3)0.001 (3)0.007 (2)
C80.085 (3)0.119 (4)0.066 (3)0.003 (3)0.014 (2)0.034 (3)
C90.0623 (19)0.0522 (19)0.0470 (19)0.0117 (15)0.0050 (15)0.0032 (15)
C100.078 (2)0.0499 (19)0.059 (2)0.0026 (16)0.0052 (17)0.0048 (16)
C110.090 (2)0.054 (2)0.059 (2)0.0098 (17)0.0122 (18)0.0065 (17)
C120.097 (3)0.075 (2)0.055 (2)0.012 (2)0.0048 (19)0.0040 (19)
C130.094 (3)0.070 (2)0.046 (2)0.0174 (19)0.0008 (18)0.0048 (17)
C140.088 (2)0.062 (2)0.050 (2)0.0221 (18)0.0030 (18)0.0026 (17)
C150.157 (5)0.104 (4)0.060 (3)0.040 (3)0.011 (3)0.020 (3)
C160.171 (5)0.065 (3)0.085 (4)0.021 (3)0.028 (3)0.004 (3)
C170.065 (2)0.0488 (19)0.066 (2)0.0052 (15)0.0057 (17)0.0144 (17)
C180.077 (2)0.057 (2)0.061 (2)0.0142 (17)0.0022 (18)0.0140 (17)
C190.076 (2)0.065 (2)0.068 (2)0.0041 (18)0.0016 (17)0.0204 (18)
C200.075 (2)0.067 (2)0.099 (3)0.0040 (19)0.009 (2)0.038 (2)
C210.075 (2)0.051 (2)0.102 (3)0.0146 (17)0.001 (2)0.025 (2)
C220.071 (2)0.055 (2)0.085 (3)0.0144 (17)0.0084 (18)0.0122 (18)
C230.126 (4)0.072 (3)0.150 (5)0.040 (3)0.016 (4)0.038 (3)
C240.120 (4)0.093 (3)0.075 (3)0.018 (3)0.004 (3)0.027 (3)
C250.0466 (17)0.065 (2)0.068 (2)0.0155 (15)0.0074 (16)0.0101 (18)
C260.0552 (19)0.070 (2)0.069 (2)0.0109 (16)0.0029 (16)0.0071 (18)
C270.058 (2)0.074 (2)0.086 (3)0.0002 (17)0.0006 (18)0.020 (2)
C280.072 (2)0.071 (2)0.098 (3)0.0002 (19)0.007 (2)0.001 (2)
C290.077 (2)0.084 (3)0.070 (2)0.003 (2)0.0074 (19)0.003 (2)
C300.063 (2)0.082 (2)0.060 (2)0.0054 (18)0.0044 (17)0.0103 (19)
C310.135 (4)0.121 (4)0.089 (4)0.021 (4)0.006 (3)0.020 (3)
C320.097 (3)0.089 (3)0.119 (4)0.010 (3)0.009 (3)0.027 (3)
C330.0542 (18)0.0521 (19)0.057 (2)0.0031 (15)0.0002 (15)0.0144 (16)
C340.068 (2)0.054 (2)0.060 (2)0.0099 (15)0.0004 (16)0.0106 (16)
C350.083 (2)0.068 (2)0.062 (2)0.0127 (19)0.0100 (18)0.0238 (18)
C360.082 (2)0.061 (2)0.091 (3)0.0016 (18)0.001 (2)0.027 (2)
C370.085 (2)0.051 (2)0.078 (3)0.0032 (17)0.012 (2)0.0125 (18)
C380.078 (2)0.059 (2)0.063 (2)0.0021 (17)0.0086 (17)0.0109 (17)
C390.130 (4)0.065 (3)0.103 (3)0.018 (3)0.019 (3)0.012 (3)
C400.128 (4)0.093 (3)0.078 (3)0.022 (3)0.012 (3)0.034 (3)
C410.0614 (18)0.0562 (19)0.0354 (17)0.0058 (15)0.0015 (14)0.0098 (14)
C420.067 (2)0.060 (2)0.058 (2)0.0176 (16)0.0119 (16)0.0109 (16)
C430.086 (2)0.0490 (19)0.067 (2)0.0144 (17)0.0115 (18)0.0068 (16)
C440.082 (2)0.065 (2)0.064 (2)0.0040 (18)0.0073 (18)0.0112 (18)
C450.0589 (18)0.073 (2)0.050 (2)0.0050 (17)0.0057 (15)0.0009 (17)
C460.0618 (19)0.066 (2)0.0452 (19)0.0126 (16)0.0032 (15)0.0024 (15)
C470.068 (2)0.104 (3)0.068 (3)0.004 (2)0.010 (2)0.002 (2)
C480.134 (4)0.058 (3)0.138 (5)0.016 (3)0.037 (3)0.006 (3)
Geometric parameters (Å, º) top
P1—O11.574 (2)F34—C471.304 (8)
P1—O21.576 (2)F34A—C471.306 (10)
P1—N11.571 (2)F35—C471.320 (8)
P1—N31.561 (2)F35A—C471.271 (9)
P2—O31.567 (2)F36—C471.297 (7)
P2—O41.582 (2)F36A—C471.276 (10)
P2—N11.575 (2)O1—C11.400 (3)
P2—N21.560 (2)O2—C91.388 (3)
P3—O51.570 (2)O3—C171.404 (4)
P3—O61.580 (2)O4—C251.405 (4)
P3—N21.567 (2)O5—C331.406 (3)
P3—N31.570 (2)O6—C411.394 (3)
F1—C71.312 (8)C1—C21.369 (4)
F1A—C71.313 (12)C1—C61.370 (4)
F2—C71.297 (8)C2—H20.9300
F2A—C71.322 (12)C2—C31.374 (4)
F3—C71.309 (7)C3—C41.373 (5)
F3A—C71.309 (12)C3—C71.468 (5)
F4—C81.298 (9)C4—H40.9300
F4A—C81.282 (10)C4—C51.371 (5)
F5—C81.271 (9)C5—C61.385 (4)
F5A—C81.319 (10)C5—C81.474 (5)
F6—C81.311 (8)C6—H60.9300
F6A—C81.293 (10)C9—C101.374 (4)
F7—C151.289 (10)C9—C141.372 (4)
F7A—C151.301 (8)C10—H100.9300
F8—C151.299 (10)C10—C111.381 (4)
F8A—C151.298 (8)C11—C121.380 (5)
F9—C151.336 (11)C11—C161.470 (5)
F9A—C151.293 (8)C12—H120.9300
F10—C161.247 (9)C12—C131.373 (4)
F10A—C161.335 (10)C13—C141.371 (4)
F11—C161.341 (9)C13—C151.468 (5)
F11A—C161.317 (8)C14—H140.9300
F12—C161.294 (8)C17—C181.354 (4)
F12A—C161.276 (9)C17—C221.385 (4)
F13—C231.307 (9)C18—H180.9300
F13A—C231.319 (13)C18—C191.382 (4)
F14—C231.297 (9)C19—C201.381 (4)
F14A—C231.324 (12)C19—C241.456 (5)
F15—C231.308 (9)C20—H200.9300
F15A—C231.311 (12)C20—C211.370 (5)
F16—C241.337 (8)C21—C221.378 (5)
F16A—C241.304 (8)C21—C231.469 (5)
F17—C241.307 (10)C22—H220.9300
F17A—C241.277 (9)C25—C261.370 (4)
F18—C241.280 (9)C25—C301.372 (4)
F18A—C241.303 (8)C26—H260.9300
F19—C311.295 (9)C26—C271.388 (4)
F19A—C311.305 (10)C27—C281.377 (5)
F20—C311.277 (9)C27—C321.451 (5)
F20A—C311.320 (9)C28—H280.9300
F21—C311.304 (10)C28—C291.376 (5)
F21A—C311.284 (10)C29—C301.383 (5)
F22—C321.316 (8)C29—C311.465 (6)
F22A—C321.282 (10)C30—H300.9300
F23—C321.322 (8)C33—C341.360 (4)
F23A—C321.316 (10)C33—C381.360 (4)
F24—C321.298 (7)C34—H340.9300
F24A—C321.308 (10)C34—C351.392 (4)
F25—C391.340 (10)C35—C361.378 (5)
F25A—C391.300 (11)C35—C401.461 (5)
F26—C391.310 (10)C36—H360.9300
F26A—C391.305 (11)C36—C371.374 (5)
F27—C391.319 (10)C37—C381.382 (4)
F27A—C391.309 (10)C37—C391.467 (5)
F28—C401.371 (7)C38—H380.9300
F28A—C401.245 (9)C41—C421.368 (4)
F29—C401.272 (9)C41—C461.375 (4)
F29A—C401.294 (9)C42—H420.9300
F30—C401.280 (8)C42—C431.383 (4)
F30A—C401.391 (8)C43—C441.376 (4)
F31—C481.295 (9)C43—C481.473 (5)
F31A—C481.288 (10)C44—H440.9300
F32—C481.301 (8)C44—C451.376 (4)
F32A—C481.287 (11)C45—C461.382 (4)
F33—C481.273 (9)C45—C471.467 (4)
F33A—C481.305 (10)C46—H460.9300
O1—P1—O2100.80 (11)F15A—C23—C21114.9 (13)
N1—P1—O1108.95 (12)F16—C24—C19115.6 (6)
N1—P1—O2112.37 (12)F16A—C24—C19110.7 (7)
N3—P1—O1110.77 (11)F17—C24—F1698.1 (7)
N3—P1—O2104.87 (12)F17—C24—C19114.9 (8)
N3—P1—N1117.74 (12)F17A—C24—F16A109.6 (9)
O3—P2—O4100.23 (11)F17A—C24—F18A103.8 (8)
O3—P2—N1113.20 (12)F17A—C24—C19111.2 (7)
N1—P2—O4107.77 (12)F18—C24—F16104.4 (10)
N2—P2—O3105.87 (12)F18—C24—F17107.6 (9)
N2—P2—O4111.95 (12)F18—C24—C19114.5 (8)
N2—P2—N1116.65 (12)F18A—C24—F16A107.0 (9)
O5—P3—O699.58 (11)F18A—C24—C19114.2 (7)
N2—P3—O5107.08 (12)C26—C25—O4120.0 (3)
N2—P3—O6110.66 (12)C26—C25—C30121.8 (3)
N2—P3—N3117.22 (12)C30—C25—O4118.1 (3)
N3—P3—O5112.58 (12)C25—C26—H26120.5
N3—P3—O6108.31 (11)C25—C26—C27119.0 (3)
C1—O1—P1124.12 (17)C27—C26—H26120.5
C9—O2—P1127.37 (19)C26—C27—C32119.9 (4)
C17—O3—P2128.4 (2)C28—C27—C26119.7 (4)
C25—O4—P2117.78 (16)C28—C27—C32120.4 (4)
C33—O5—P3122.75 (17)C27—C28—H28119.7
C41—O6—P3120.21 (17)C29—C28—C27120.5 (4)
P1—N1—P2122.41 (15)C29—C28—H28119.7
P2—N2—P3122.79 (15)C28—C29—C30120.0 (4)
P1—N3—P3120.72 (13)C28—C29—C31120.3 (4)
C2—C1—O1121.8 (3)C30—C29—C31119.6 (4)
C2—C1—C6120.9 (3)C25—C30—C29118.9 (3)
C6—C1—O1117.3 (3)C25—C30—H30120.6
C1—C2—H2120.2C29—C30—H30120.6
C1—C2—C3119.6 (3)F19—C31—F21110.4 (11)
C3—C2—H2120.2F19—C31—C29112.8 (7)
C2—C3—C7120.2 (4)F19A—C31—F20A102.8 (9)
C4—C3—C2120.1 (3)F19A—C31—C29116.9 (7)
C4—C3—C7119.6 (4)F20—C31—F19108.2 (10)
C3—C4—H4119.9F20—C31—F21101.9 (7)
C5—C4—C3120.1 (3)F20—C31—C29113.5 (8)
C5—C4—H4119.9F20A—C31—C29108.3 (9)
C4—C5—C6119.9 (3)F21—C31—C29109.4 (7)
C4—C5—C8121.0 (4)F21A—C31—F19A104.0 (10)
C6—C5—C8119.1 (4)F21A—C31—F20A107.5 (10)
C1—C6—C5119.3 (3)F21A—C31—C29116.3 (8)
C1—C6—H6120.3F22—C32—F23104.3 (8)
C5—C6—H6120.3F22—C32—C27114.4 (7)
F1—C7—C3112.8 (5)F22A—C32—F23A106.7 (12)
F1A—C7—F2A104.4 (13)F22A—C32—F24A107.6 (10)
F1A—C7—C3115.3 (10)F22A—C32—C27116.5 (8)
F2—C7—F1107.7 (7)F23—C32—C27115.1 (6)
F2—C7—F3106.0 (7)F23A—C32—C27107.5 (9)
F2—C7—C3113.2 (7)F24—C32—F22104.2 (7)
F2A—C7—C3113.0 (12)F24—C32—F23104.0 (7)
F3—C7—F1105.3 (7)F24—C32—C27113.6 (6)
F3—C7—C3111.2 (6)F24A—C32—F23A103.0 (9)
F3A—C7—F1A103.1 (14)F24A—C32—C27114.4 (7)
F3A—C7—F2A100.8 (13)C34—C33—O5118.6 (3)
F3A—C7—C3118.3 (12)C38—C33—O5119.4 (3)
F4—C8—F6103.2 (9)C38—C33—C34122.0 (3)
F4—C8—C5111.8 (7)C33—C34—H34120.6
F4A—C8—F5A104.1 (10)C33—C34—C35118.7 (3)
F4A—C8—F6A103.2 (12)C35—C34—H34120.6
F4A—C8—C5116.1 (9)C34—C35—C40120.5 (4)
F5—C8—F4105.7 (8)C36—C35—C34119.7 (3)
F5—C8—F6110.0 (9)C36—C35—C40119.8 (4)
F5—C8—C5115.8 (8)C35—C36—H36119.7
F5A—C8—C5111.7 (8)C37—C36—C35120.5 (3)
F6—C8—C5109.5 (7)C37—C36—H36119.7
F6A—C8—F5A106.2 (11)C36—C37—C38119.3 (3)
F6A—C8—C5114.6 (8)C36—C37—C39119.7 (3)
C10—C9—O2115.1 (3)C38—C37—C39121.0 (4)
C14—C9—O2123.7 (3)C33—C38—C37119.7 (3)
C14—C9—C10121.2 (3)C33—C38—H38120.2
C9—C10—H10120.4C37—C38—H38120.2
C9—C10—C11119.2 (3)F25—C39—C37114.5 (9)
C11—C10—H10120.4F25A—C39—F26A108.0 (12)
C10—C11—C16119.4 (4)F25A—C39—F27A106.8 (12)
C12—C11—C10119.9 (3)F25A—C39—C37108.3 (11)
C12—C11—C16120.7 (4)F26—C39—F25104.3 (10)
C11—C12—H12120.0F26—C39—F27105.9 (10)
C13—C12—C11120.0 (3)F26—C39—C37112.3 (9)
C13—C12—H12120.0F26A—C39—F27A109.7 (13)
C12—C13—C15120.2 (3)F26A—C39—C37115.2 (11)
C14—C13—C12120.4 (3)F27—C39—F25103.3 (10)
C14—C13—C15119.3 (3)F27—C39—C37115.5 (7)
C9—C14—H14120.3F27A—C39—C37108.5 (10)
C13—C14—C9119.3 (3)F28—C40—C35111.2 (5)
C13—C14—H14120.3F28A—C40—F29A109.6 (9)
F7—C15—F8102.4 (10)F28A—C40—F30A103.3 (8)
F7—C15—F9105.2 (12)F28A—C40—C35118.7 (7)
F7—C15—C13116.4 (9)F29—C40—F28100.5 (8)
F7A—C15—C13111.2 (7)F29—C40—F30111.6 (8)
F8—C15—F9105.8 (10)F29—C40—C35115.9 (7)
F8—C15—C13117.9 (7)F29A—C40—F30A100.7 (8)
F8A—C15—F7A105.5 (8)F29A—C40—C35113.0 (7)
F8A—C15—C13109.7 (5)F30—C40—F28101.7 (7)
F9—C15—C13108.0 (8)F30—C40—C35114.1 (7)
F9A—C15—F7A106.7 (8)F30A—C40—C35109.5 (6)
F9A—C15—F8A106.8 (7)C42—C41—O6118.4 (3)
F9A—C15—C13116.3 (6)C42—C41—C46121.0 (3)
F10—C16—F11109.5 (9)C46—C41—O6120.5 (3)
F10—C16—F12104.5 (9)C41—C42—H42120.4
F10—C16—C11115.5 (8)C41—C42—C43119.3 (3)
F10A—C16—C11108.7 (7)C43—C42—H42120.4
F11—C16—C11112.2 (5)C42—C43—C48118.9 (4)
F11A—C16—F10A96.3 (7)C44—C43—C42120.4 (3)
F11A—C16—C11115.0 (5)C44—C43—C48120.6 (4)
F12—C16—F11103.7 (8)C43—C44—H44120.1
F12—C16—C11110.5 (6)C43—C44—C45119.7 (3)
F12A—C16—F10A111.6 (11)C45—C44—H44120.1
F12A—C16—F11A108.5 (8)C44—C45—C46120.1 (3)
F12A—C16—C11115.2 (7)C44—C45—C47120.6 (3)
C18—C17—O3123.0 (3)C46—C45—C47119.3 (3)
C18—C17—C22121.9 (3)C41—C46—C45119.5 (3)
C22—C17—O3115.0 (3)C41—C46—H46120.3
C17—C18—H18120.2C45—C46—H46120.3
C17—C18—C19119.5 (3)F34—C47—F35106.4 (8)
C19—C18—H18120.2F34—C47—C45114.6 (6)
C18—C19—C24120.1 (3)F34A—C47—C45111.5 (7)
C20—C19—C18119.5 (4)F35—C47—C45114.5 (6)
C20—C19—C24120.4 (4)F35A—C47—F34A106.1 (9)
C19—C20—H20119.9F35A—C47—F36A107.0 (10)
C21—C20—C19120.3 (3)F35A—C47—C45113.2 (7)
C21—C20—H20119.9F36—C47—F34103.5 (6)
C20—C21—C22120.6 (3)F36—C47—F35102.0 (7)
C20—C21—C23118.9 (4)F36—C47—C45114.5 (6)
C22—C21—C23120.6 (4)F36A—C47—F34A108.0 (10)
C17—C22—H22120.9F36A—C47—C45110.7 (8)
C21—C22—C17118.2 (3)F31—C48—F32106.6 (9)
C21—C22—H22120.9F31—C48—C43111.2 (6)
F13—C23—F15105.5 (9)F31A—C48—F33A105.6 (10)
F13—C23—C21112.8 (7)F31A—C48—C43113.4 (9)
F13A—C23—F14A100.1 (13)F32—C48—C43113.6 (7)
F13A—C23—C21115.9 (13)F32A—C48—F31A112.4 (12)
F14—C23—F13105.2 (9)F32A—C48—F33A101.3 (11)
F14—C23—F15109.1 (9)F32A—C48—C43110.0 (10)
F14—C23—C21110.6 (7)F33—C48—F31106.6 (9)
F14A—C23—C21117.1 (10)F33—C48—F32102.3 (8)
F15—C23—C21113.2 (8)F33—C48—C43115.8 (7)
F15A—C23—F13A105.9 (14)F33A—C48—C43113.5 (8)
F15A—C23—F14A100.9 (14)
P1—O1—C1—C252.2 (3)C18—C19—C24—F160.2 (11)
P1—O1—C1—C6129.3 (2)C18—C19—C24—F16A46.3 (13)
P1—O2—C9—C10154.0 (2)C18—C19—C24—F17113.4 (11)
P1—O2—C9—C1426.6 (4)C18—C19—C24—F17A75.8 (11)
P2—O3—C17—C1839.6 (4)C18—C19—C24—F18121.2 (16)
P2—O3—C17—C22143.7 (2)C18—C19—C24—F18A167.2 (10)
P2—O4—C25—C2680.0 (3)C19—C20—C21—C221.5 (5)
P2—O4—C25—C30101.4 (3)C19—C20—C21—C23178.9 (4)
P3—O5—C33—C34102.5 (3)C20—C19—C24—F16179.1 (10)
P3—O5—C33—C3880.5 (3)C20—C19—C24—F16A134.4 (13)
P3—O6—C41—C42105.7 (3)C20—C19—C24—F1765.9 (11)
P3—O6—C41—C4678.0 (3)C20—C19—C24—F17A103.5 (11)
O1—P1—O2—C950.1 (2)C20—C19—C24—F1859.5 (16)
O1—P1—N1—P2132.43 (16)C20—C19—C24—F18A13.5 (11)
O1—P1—N3—P3142.11 (15)C20—C21—C22—C170.8 (5)
O1—C1—C2—C3179.8 (3)C20—C21—C23—F13179.6 (11)
O1—C1—C6—C5177.7 (2)C20—C21—C23—F13A146 (2)
O2—P1—O1—C1141.5 (2)C20—C21—C23—F1462.8 (12)
O2—P1—N1—P2116.75 (17)C20—C21—C23—F14A96 (2)
O2—P1—N3—P3109.95 (17)C20—C21—C23—F1559.9 (12)
O2—C9—C10—C11178.9 (3)C20—C21—C23—F15A22 (3)
O2—C9—C14—C13179.2 (3)C22—C17—C18—C190.3 (5)
O3—P2—O4—C25174.0 (2)C22—C21—C23—F130.8 (12)
O3—P2—N1—P1121.81 (16)C22—C21—C23—F13A34 (2)
O3—P2—N2—P3129.18 (17)C22—C21—C23—F14116.8 (11)
O3—C17—C18—C19176.8 (3)C22—C21—C23—F14A84 (2)
O3—C17—C22—C21176.8 (3)C22—C21—C23—F15120.5 (11)
O4—P2—O3—C1757.9 (3)C22—C21—C23—F15A158 (2)
O4—P2—N1—P1128.29 (16)C23—C21—C22—C17179.6 (4)
O4—P2—N2—P3122.54 (17)C24—C19—C20—C21178.1 (4)
O4—C25—C26—C27178.5 (2)C25—C26—C27—C280.3 (5)
O4—C25—C30—C29178.4 (3)C25—C26—C27—C32179.6 (3)
O5—P3—O6—C41178.1 (2)C26—C25—C30—C290.2 (5)
O5—P3—N2—P2115.28 (17)C26—C27—C28—C290.6 (5)
O5—P3—N3—P1105.67 (17)C26—C27—C32—F22172.2 (8)
O5—C33—C34—C35177.6 (3)C26—C27—C32—F22A147.2 (17)
O5—C33—C38—C37177.9 (3)C26—C27—C32—F2351.5 (12)
O6—P3—O5—C3370.5 (2)C26—C27—C32—F23A93.2 (12)
O6—P3—N2—P2137.14 (16)C26—C27—C32—F2468.2 (10)
O6—P3—N3—P1145.21 (15)C26—C27—C32—F24A20.5 (14)
O6—C41—C42—C43175.0 (3)C27—C28—C29—C300.6 (5)
O6—C41—C46—C45176.4 (2)C27—C28—C29—C31179.3 (4)
N1—P1—O1—C123.1 (3)C28—C27—C32—F228.5 (10)
N1—P1—O2—C965.7 (2)C28—C27—C32—F22A32.1 (18)
N1—P1—N3—P315.8 (2)C28—C27—C32—F23129.2 (11)
N1—P2—O3—C1756.6 (3)C28—C27—C32—F23A87.5 (12)
N1—P2—O4—C2555.4 (2)C28—C27—C32—F24111.0 (10)
N1—P2—N2—P32.2 (2)C28—C27—C32—F24A158.8 (13)
N2—P2—O3—C17174.4 (2)C28—C29—C30—C250.1 (5)
N2—P2—O4—C2574.2 (2)C28—C29—C31—F19149.3 (15)
N2—P2—N1—P11.4 (2)C28—C29—C31—F19A161.8 (9)
N2—P3—O5—C33174.2 (2)C28—C29—C31—F2025.6 (11)
N2—P3—O6—C4165.6 (2)C28—C29—C31—F20A82.8 (13)
N2—P3—N3—P119.2 (2)C28—C29—C31—F2187.4 (10)
N3—P1—O1—C1107.9 (2)C28—C29—C31—F21A38.3 (17)
N3—P1—O2—C9165.2 (2)C30—C25—C26—C270.1 (4)
N3—P1—N1—P25.3 (2)C30—C29—C31—F1929.4 (16)
N3—P3—O5—C3344.0 (3)C30—C29—C31—F19A19.4 (11)
N3—P3—O6—C4164.1 (2)C30—C29—C31—F20153.1 (9)
N3—P3—N2—P212.3 (2)C30—C29—C31—F20A95.9 (13)
C1—C2—C3—C42.2 (5)C30—C29—C31—F2193.9 (10)
C1—C2—C3—C7178.5 (3)C30—C29—C31—F21A143.0 (16)
C2—C1—C6—C50.9 (4)C31—C29—C30—C25178.9 (4)
C2—C3—C4—C50.9 (5)C32—C27—C28—C29179.9 (4)
C2—C3—C7—F17.7 (8)C33—C34—C35—C360.3 (5)
C2—C3—C7—F1A39 (2)C33—C34—C35—C40179.0 (3)
C2—C3—C7—F2114.9 (10)C34—C33—C38—C371.0 (5)
C2—C3—C7—F2A80.7 (16)C34—C35—C36—C370.8 (5)
C2—C3—C7—F3125.8 (9)C34—C35—C40—F2837.2 (9)
C2—C3—C7—F3A162 (2)C34—C35—C40—F28A100.3 (13)
C3—C4—C5—C61.3 (5)C34—C35—C40—F2976.8 (10)
C3—C4—C5—C8178.9 (3)C34—C35—C40—F29A30.1 (12)
C4—C3—C7—F1172.9 (7)C34—C35—C40—F30151.5 (10)
C4—C3—C7—F1A141 (2)C34—C35—C40—F30A141.4 (9)
C4—C3—C7—F264.5 (11)C35—C36—C37—C380.5 (5)
C4—C3—C7—F2A98.7 (16)C35—C36—C37—C39178.5 (4)
C4—C3—C7—F354.8 (10)C36—C35—C40—F28142.0 (8)
C4—C3—C7—F3A19 (2)C36—C35—C40—F28A78.9 (14)
C4—C5—C6—C12.2 (4)C36—C35—C40—F29104.0 (10)
C4—C5—C8—F4143.7 (12)C36—C35—C40—F29A150.7 (11)
C4—C5—C8—F4A105.6 (13)C36—C35—C40—F3027.7 (11)
C4—C5—C8—F522.5 (14)C36—C35—C40—F30A39.3 (10)
C4—C5—C8—F5A13.5 (12)C36—C37—C38—C330.4 (5)
C4—C5—C8—F6102.6 (8)C36—C37—C39—F2577.3 (11)
C4—C5—C8—F6A134.2 (16)C36—C37—C39—F25A53.0 (17)
C6—C1—C2—C31.3 (4)C36—C37—C39—F26164.1 (10)
C6—C5—C8—F436.1 (12)C36—C37—C39—F26A174.1 (18)
C6—C5—C8—F4A74.2 (13)C36—C37—C39—F2742.6 (13)
C6—C5—C8—F5157.3 (13)C36—C37—C39—F27A62.6 (15)
C6—C5—C8—F5A166.7 (11)C38—C33—C34—C350.6 (4)
C6—C5—C8—F677.6 (9)C38—C37—C39—F25101.7 (11)
C6—C5—C8—F6A46.0 (16)C38—C37—C39—F25A125.9 (17)
C7—C3—C4—C5179.8 (3)C38—C37—C39—F2616.9 (11)
C8—C5—C6—C1178.0 (3)C38—C37—C39—F26A4.8 (19)
C9—C10—C11—C120.3 (5)C38—C37—C39—F27138.5 (12)
C9—C10—C11—C16179.5 (4)C38—C37—C39—F27A118.5 (15)
C10—C9—C14—C130.1 (5)C39—C37—C38—C33179.4 (3)
C10—C11—C12—C131.4 (5)C40—C35—C36—C37178.5 (4)
C10—C11—C16—F1085.5 (12)C41—C42—C43—C441.8 (5)
C10—C11—C16—F10A125.4 (8)C41—C42—C43—C48176.6 (4)
C10—C11—C16—F1141.0 (12)C42—C41—C46—C450.2 (4)
C10—C11—C16—F11A18.8 (10)C42—C43—C44—C450.7 (5)
C10—C11—C16—F12156.2 (7)C42—C43—C48—F3178.3 (13)
C10—C11—C16—F12A108.6 (14)C42—C43—C48—F31A150.2 (16)
C11—C12—C13—C141.7 (5)C42—C43—C48—F32161.5 (8)
C11—C12—C13—C15178.8 (4)C42—C43—C48—F32A82.9 (17)
C12—C11—C16—F1093.8 (12)C42—C43—C48—F3343.5 (11)
C12—C11—C16—F10A53.9 (9)C42—C43—C48—F33A29.8 (13)
C12—C11—C16—F11139.7 (11)C43—C44—C45—C460.8 (5)
C12—C11—C16—F11A160.5 (8)C43—C44—C45—C47178.6 (3)
C12—C11—C16—F1224.6 (9)C44—C43—C48—F31100.1 (13)
C12—C11—C16—F12A72.2 (15)C44—C43—C48—F31A28.2 (17)
C12—C13—C14—C91.0 (5)C44—C43—C48—F3220.1 (10)
C12—C13—C15—F7178.5 (15)C44—C43—C48—F32A98.7 (17)
C12—C13—C15—F7A140.9 (9)C44—C43—C48—F33138.1 (9)
C12—C13—C15—F859.2 (14)C44—C43—C48—F33A148.7 (12)
C12—C13—C15—F8A102.8 (10)C44—C45—C46—C411.3 (4)
C12—C13—C15—F960.6 (15)C44—C45—C47—F34131.5 (8)
C12—C13—C15—F9A18.5 (11)C44—C45—C47—F34A170.2 (13)
C14—C9—C10—C110.5 (5)C44—C45—C47—F358.2 (12)
C14—C13—C15—F71.0 (16)C44—C45—C47—F35A50.7 (10)
C14—C13—C15—F7A38.6 (10)C44—C45—C47—F36109.1 (7)
C14—C13—C15—F8121.3 (13)C44—C45—C47—F36A69.5 (14)
C14—C13—C15—F8A77.7 (10)C46—C41—C42—C431.3 (4)
C14—C13—C15—F9118.9 (14)C46—C45—C47—F3449.1 (9)
C14—C13—C15—F9A161.0 (9)C46—C45—C47—F34A10.4 (13)
C15—C13—C14—C9179.5 (4)C46—C45—C47—F35172.4 (11)
C16—C11—C12—C13179.4 (4)C46—C45—C47—F35A129.9 (9)
C17—C18—C19—C200.3 (5)C46—C45—C47—F3670.3 (8)
C17—C18—C19—C24179.0 (4)C46—C45—C47—F36A109.9 (14)
C18—C17—C22—C210.0 (5)C47—C45—C46—C41178.1 (3)
C18—C19—C20—C211.2 (5)C48—C43—C44—C45177.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···F260.932.583.478 (10)163
C30—H30···F6Ai0.932.693.379 (14)132
C36—H36···F32Aii0.932.593.40 (2)146
C44—H44···F29iii0.932.673.521 (13)152
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x+1, y+1, z.
 

Funding information

ARH was supported by a graduate fellowship from The Pennsylvania State University.

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