N-Fluoropyridinium trifluoromethanesulfonate and 1-fluoro-2,4,6-trimethoxy-1,3,5-triazinium hexafluoroantimonate: the first experimental determination of the F-N⁺ bond length involving sp² nitrogen

The structures of N-fluoro­pyridinium tri­fluoro­methane­sulfon­ate, C₅H₅FN⁺·CF₃O₃S^-, (I), and 1-fluoro-2,4,6-tri­methoxy-1,3,5-triazinium hexa­fluoro­antimonate, (C₆H₉FN₃O₃)[SbF₆], (II), are presented. The N-F bond lengths in (I), a well known electrophilic fluorinating agent, and its novel analogue, (II), are 1.357 (4) and 1.354 (4) Å, respectively.

S1. Comment

Prior to this study, the chloro analogue of the title triazine, (II), [(ClCN)₃F]⁺·[AsF₆]⁻ (Schleyer et al., 1993) was the only sp² N—F⁺ containing molecule to be reported by X-ray diffraction. However, the investigators rejected their experimental N—F⁺ bond length of 1.11 Å, due to the cations being severely disordered, and proposed, instead, a value of 1.314 Å, which they obtained from quantum-chemical calculations at the HF/6–31+G* level. This computed length was confirmed subsequently (Broschag et al., 1994) and improved more recently using MP2 (1.360 Å) and B3LYP (1.349 Å) theory level calculations (Fraenk et al., 2001). These latter values show excellent agreement with the N—F⁺ length of 1.354 (4) Å e stablished in the current study for the title triazinyl derivative, (II) (Fig. 2 and Table 2). At 1.357 (4) Å, the analogous bond in 1-fluoropyridinium trifluoromethanesulfonate, (I) (Fig. 1 and Table 1), is identical within experimental error, and also shows good agreement with the computed values of 1.323 (RHF level), 1.370 (MP2) and 1.357 Å (B3LYP) (Fraenk et al., 2001). \sch

Comparison of the title structures, (I) and (II), with their respective neutral precursors, pyridine (Mootz & Wussow, 1981) and trimethoxytriazine (Glówka & Iwanicka, 1989), reveals changes to the ring geometry that are similar to those seen on protonation. As expected, involvement of the N-atom lone pair in a covalent bond to F⁺ has significantly expanded the C—N—F bond angle in both (I) and (II). As a consequence, the remaining ring angles have also changed, the magnitude of the difference diminishing on traversing the ring away from the F site in the order meta > ortho > para (Table 3).

In the case of the pyridinyl derivative, (I), a small contraction of the average ring bonds of between 0.024 and 0.010 Å can also be detected on forming the F⁺ adduct. In contrast, the bond-length changes in methoxy triazinyl, (II), are more complex and are strongly influenced by the OMe substituents, which are conjugated with the ring delocalization system. In the parent triazine, the OMe groups and the ring are coplanar, due to the molecule lying on a crystallographic mirror plane. Molecule (II) is also nearly planar, as shown by the MeOCN torsion angles of 1.5 (6), −1.0 (6) and 1.3 (6)°. Also, like the parent molecule, the ring C—N bonds trans to OMe are considerably longer [1.349 (6), 1.344 (5) and 1.356 (6) Å] than the cis bonds [1.291 (5), 1.327 (5) and 1.292 (5) Å]. However, the C_{3 h} symmetry of (MeOCN)₃ is lost in (II), because both OMe groups flanking the F-bonded N atom point away from the F. Consequently, both N—C bonds to the F-bonded N atom are of the longer type [1.349 (6) and 1.356 (6) Å].

The fluropyridinium and fluorotriazinium structures, (I) and (II), also differ in their crystal packing. Whereas there are no significant short interionic contacts in (I) (apart from three C—H···O contacts), in (II), each SbF₆⁻ anion is sandwiched between two [(MeOCN)₃F]⁺ rings, and participates in several short interionic C···F contacts in the range 2.83 (1)–2.89 (1) Å. The three-point contact and central location of the [SbF₆]⁻ above one ring (Fig. 2) is reminiscent of the interaction between [SbF₆]⁻ and the central aromatic C₆ ring in hexaazaoctadecahydrovoronene tetrakis[SbF₆]⁻ acetonitrile solvate (Miller et al., 1990).

S2. Experimental

A sample of (I) with appropriate NMR properties was prepared by an adaptation of the one-pot procedure of Umemoto et al. (1991) via direct flow-fluorination of pyridine and LiOTf in MeCN at 238 K (Banks et al., 1996). Suitable crystals were obtained by recrystallization from dry tetrahydrofuran (m.p. 459 K; literature value: 458–460 K). Analysis, found: C 28.9, H 1.9, N 5.6%; calculated for C₆H₅F₄NO₃S: C 29.1, H 2.0, N 5.7%. In order to prepare (II) (Banks & Besheesh, 2002), a homogeneous mixture of 2,4,6-trimethoxy-1,3,5-triazine (0.50 g, 2.92 mmol), hexafluoroantimonic acid (0.69 g, 2.92 mmol) and hexafluoroisopropanol (80 ml) were placed in a Pyrex flow-fluorination reactor (Banks et al., 1996). This mixture was cooled to 268 K, stirred vigorously and treated with a 1:9 (v/v) F₂/N₂ blend (flow rate 130 ml min⁻¹) until the exit gas gave a strong positive test (KI) for fluorine. The resulting colourless solution was concentrated under reduced pressure (volume reduced to about 10 ml), then mixed with dry diethyl ether (50 ml), causing a brilliant-white crystalline solid to precipitate. This solid was collected by suction filtration, washed with dry diethyl ether (30 ml) and dried in vacuo, to give a material which was identified by elemental and NMR analysis as 1-fluoro-2,4,6-trimethoxy-1,3,5-triazinium hexafluoroantimonate, (II) (1.22 g, 2.86 mmol, 98%; m.p. 484 K, decomposition). ¹H NMR (CD₃CN, TMS, δ, p.p.m.): 4.59 (s, 2OCH₃), 4.44 (s, OCH₃); ¹⁹F NMR Is this the correct F isotope? (CD₃CN, TFA, δ, p.p.m.): 18.9 (br s, NF⁺), −20.75 to −79.95 (complex, SbF₆⁺). Elemental analysis, calculated for C₆H₉F₇N₃O₃Sb: C 17.0, H 2.1, N 9.9, Sb 28.6%; found: C 17.1, H 1.9, N 9.5, Sb 28.9%. Crystals of (I) and (II) suitable for X-ray analysis were grown by vapour diffusion of Et₂O into MeCN solutions.

S3. Refinement

H atoms were treated as riding, with C—H distances in the range 0.93–0.97 Å. Is this added text OK?

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) for (I); CAD-4 Software (Enraf-Nonius, 1994) for (II). Cell refinement: MSC/AFC Diffractometer Control Software for (I); CAD-4 Software for (II). Data reduction: TEXSAN (Molecular Structure Corporation, 1999) for (I); XCAD4 (Harms & Wocadlo 1995) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. A view of the structure of (I) with the atomic labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the structure of (II) with the atomic labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

(I) N-fluoropyridinium trifluoromethanesulfonate

Crystal data

C5H5FN^+·CF3O3S^−	F(000) = 496
Mr = 247.17	Dx = 1.742 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.027 (2) Å	θ = 8.4–16.1°
b = 12.901 (4) Å	µ = 0.39 mm^−1
c = 12.490 (3) Å	T = 293 K
β = 103.96 (3)°	Prism, colourless
V = 942.5 (5) Å^3	0.40 × 0.25 × 0.25 mm
Z = 4

Data collection

Rigaku AFC-6S diffractometer	Rint = 0.034
θ/2θ scans	θmax = 25.3°, θmin = 2.3°
Absorption correction: ψ scan (North et al., 1968)	h = −7→0
Tmin = 0.809, Tmax = 0.905	k = 0→15
1824 measured reflections	l = −14→14
1658 independent reflections	3 standard reflections every 150 reflections
890 reflections with I > 2σ(I)	intensity decay: 0.0%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0657P)^2 + 0.31P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.149	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.27 e Å^−3
1658 reflections	Δρmin = −0.23 e Å^−3
136 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4845 (7)	0.3394 (3)	0.7008 (3)	0.0531 (10)
C2	0.6397 (8)	0.3836 (3)	0.6569 (4)	0.0549 (12)
H2	0.7703	0.4131	0.7017	0.066*
C3	0.6059 (9)	0.3852 (3)	0.5463 (4)	0.0623 (13)
H3	0.7124	0.416	0.5135	0.075*
C4	0.4149 (8)	0.3412 (3)	0.4839 (4)	0.0590 (13)
H4	0.3876	0.3418	0.4073	0.071*
C5	0.2599 (8)	0.2952 (4)	0.5349 (4)	0.0668 (14)
H5	0.1292	0.2643	0.4918	0.08*
C6	0.2946 (8)	0.2942 (3)	0.6472 (4)	0.0592 (13)
H6	0.1922	0.2639	0.6829	0.071*
C7	0.8502 (8)	0.0571 (4)	0.6254 (4)	0.0579 (12)
O1	0.5760 (5)	0.1016 (3)	0.7512 (3)	0.0710 (10)
O2	0.9300 (5)	0.1947 (2)	0.7751 (3)	0.0642 (9)
O3	0.9265 (6)	0.0160 (3)	0.8310 (3)	0.0749 (10)
F1	0.5200 (6)	0.3388 (2)	0.8122 (2)	0.0859 (10)
F2	0.7626 (7)	0.1246 (3)	0.5487 (2)	0.1118 (13)
F3	0.7582 (7)	−0.0325 (3)	0.5950 (3)	0.1209 (14)
F4	1.0669 (5)	0.0510 (3)	0.6206 (3)	0.0970 (11)
S1	0.81716 (17)	0.09660 (8)	0.76085 (8)	0.0453 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.068 (3)	0.050 (2)	0.042 (2)	0.010 (2)	0.0152 (19)	0.0016 (16)
C2	0.052 (3)	0.039 (3)	0.071 (3)	−0.005 (2)	0.011 (2)	−0.003 (2)
C3	0.069 (3)	0.051 (3)	0.072 (3)	0.005 (3)	0.026 (3)	0.013 (2)
C4	0.068 (3)	0.060 (3)	0.048 (3)	0.005 (3)	0.013 (3)	0.006 (2)
C5	0.060 (3)	0.067 (3)	0.061 (3)	−0.007 (3)	−0.008 (3)	0.003 (3)
C6	0.050 (3)	0.052 (3)	0.081 (4)	−0.001 (2)	0.025 (3)	0.009 (3)
C7	0.061 (3)	0.063 (3)	0.052 (3)	−0.005 (3)	0.018 (2)	−0.005 (2)
O1	0.0458 (18)	0.091 (3)	0.081 (2)	0.0042 (18)	0.0249 (16)	−0.0070 (19)
O2	0.066 (2)	0.060 (2)	0.066 (2)	−0.0070 (17)	0.0138 (16)	−0.0056 (16)
O3	0.086 (2)	0.075 (2)	0.064 (2)	0.023 (2)	0.0176 (19)	0.0226 (18)
F1	0.116 (3)	0.095 (2)	0.0461 (16)	0.0196 (19)	0.0177 (16)	−0.0005 (14)
F2	0.143 (3)	0.136 (3)	0.0471 (17)	0.023 (3)	0.0061 (19)	0.0192 (19)
F3	0.162 (4)	0.109 (3)	0.110 (3)	−0.065 (3)	0.069 (2)	−0.058 (2)
F4	0.078 (2)	0.137 (3)	0.091 (2)	0.001 (2)	0.0484 (17)	−0.019 (2)
S1	0.0419 (6)	0.0506 (6)	0.0436 (6)	0.0048 (6)	0.0110 (4)	0.0030 (5)

Geometric parameters (Å, º)

N1—F1	1.357 (4)	C5—H5	0.93
N1—C2	1.322 (6)	C6—H6	0.93
N1—C6	1.315 (6)	C7—F3	1.299 (5)
C2—C3	1.347 (7)	C7—F2	1.308 (5)
C3—C4	1.350 (6)	C7—F4	1.324 (5)
C4—C5	1.385 (7)	C7—S1	1.823 (5)
C5—C6	1.367 (7)	O1—S1	1.430 (3)
C2—H2	0.93	O2—S1	1.427 (3)
C3—H3	0.93	O3—S1	1.416 (3)
C4—H4	0.93
F1—N1—C2	118.4 (4)	C4—C5—H5	119.2
F1—N1—C6	115.0 (4)	N1—C6—H6	122.7
C2—N1—C6	126.7 (4)	C5—C6—H6	122.7
N1—C2—C3	119.0 (4)	F3—C7—F2	108.1 (4)
C2—C3—C4	118.9 (4)	F3—C7—F4	106.8 (4)
C3—C4—C5	119.3 (4)	F2—C7—F4	103.6 (4)
C4—C5—C6	121.6 (4)	F3—C7—S1	112.7 (3)
N1—C6—C5	114.6 (4)	F2—C7—S1	112.2 (3)
N1—C2—H2	120.5	F4—C7—S1	112.9 (3)
C3—C2—H2	120.5	O3—S1—O2	115.9 (2)
C2—C3—H3	120.5	O3—S1—O1	113.4 (2)
C4—C3—H3	120.5	O2—S1—O1	114.5 (2)
C3—C4—H4	120.3	O3—S1—C7	103.3 (2)
C5—C4—H4	120.3	O2—S1—C7	102.0 (2)
C6—C5—H5	119.2	O1—S1—C7	105.7 (2)
C6—N1—C2—C3	0.8 (7)	F2—C7—S1—O3	−178.5 (3)
F1—N1—C2—C3	−179.7 (4)	F4—C7—S1—O3	−61.9 (4)
N1—C2—C3—C4	−0.3 (6)	F3—C7—S1—O2	179.9 (4)
C2—C3—C4—C5	−0.4 (7)	F2—C7—S1—O2	−57.8 (4)
C3—C4—C5—C6	0.7 (7)	F4—C7—S1—O2	58.7 (4)
C2—N1—C6—C5	−0.5 (7)	F3—C7—S1—O1	−60.2 (4)
F1—N1—C6—C5	179.9 (4)	F2—C7—S1—O1	62.1 (4)
C4—C5—C6—N1	−0.2 (7)	F4—C7—S1—O1	178.7 (4)
F3—C7—S1—O3	59.2 (4)

(II) 1-fluoro-2,4,6-trimethoxy-1,3,5-triazinium hexafluoroantimonate

Crystal data

C6H9FN3O3^+·F6Sb^−	F(000) = 816
Mr = 425.91	Dx = 2.119 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.616 (2) Å	θ = 8.1–11.4°
b = 11.843 (3) Å	µ = 2.16 mm^−1
c = 14.924 (3) Å	T = 203 K
β = 97.43 (2)°	Plate, colourless
V = 1334.9 (6) Å^3	0.30 × 0.15 × 0.10 mm
Z = 4

Data collection

Nonius MACH3 diffractometer	Rint = 0.025
θ/2θ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: ψ scan (North et al., 1968)	h = −8→2
Tmin = 0.686, Tmax = 0.803	k = 0→14
3200 measured reflections	l = −17→17
2335 independent reflections	3 standard reflections every 150 reflections
1799 reflections with I > 2σ(I)	intensity decay: 0.0%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0253P)^2 + 1.7485P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.071	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.98 e Å^−3
2335 reflections	Δρmin = −0.66 e Å^−3
181 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.8022 (4)	0.9017 (2)	0.8508 (2)	0.0599 (8)
O2	0.4976 (4)	0.9010 (3)	0.9049 (2)	0.0450 (8)
O4	0.4855 (4)	0.5225 (2)	0.8978 (2)	0.0402 (7)
O6	0.9630 (4)	0.7167 (3)	0.8261 (2)	0.0480 (8)
N1	0.7242 (5)	0.8021 (3)	0.8660 (2)	0.0378 (9)
N3	0.4821 (4)	0.7080 (3)	0.9042 (2)	0.0331 (8)
N5	0.7321 (5)	0.6090 (3)	0.8615 (2)	0.0339 (8)
C2	0.5619 (6)	0.8022 (4)	0.8930 (3)	0.0348 (10)
C4	0.5718 (6)	0.6144 (4)	0.8873 (3)	0.0320 (10)
C6	0.8085 (6)	0.7045 (4)	0.8507 (3)	0.0373 (11)
C7	0.3225 (7)	0.9038 (5)	0.9356 (4)	0.0629 (16)
H7A	0.2867	0.9816	0.9424	0.094*
H7B	0.3276	0.8653	0.9933	0.094*
H7C	0.2373	0.8663	0.8915	0.094*
C8	0.5689 (7)	0.4162 (4)	0.8790 (4)	0.0551 (13)
H8A	0.4908	0.3542	0.8894	0.083*
H8B	0.6797	0.4083	0.9186	0.083*
H8C	0.5919	0.4152	0.8166	0.083*
C9	1.0554 (7)	0.6126 (5)	0.8076 (4)	0.0688 (17)
H9A	1.17	0.631	0.7898	0.103*
H9B	0.9858	0.5714	0.7593	0.103*
H9C	1.0717	0.5662	0.8617	0.103*
Sb1	0.44835 (5)	0.72009 (3)	0.62049 (2)	0.04520 (13)
F2	0.6878 (4)	0.7299 (3)	0.6643 (2)	0.0882 (12)
F3	0.4654 (6)	0.8395 (3)	0.5428 (2)	0.1121 (16)
F4	0.3957 (6)	0.8175 (3)	0.7104 (2)	0.1013 (14)
F5	0.4298 (4)	0.6005 (2)	0.69873 (19)	0.0567 (8)
F6	0.4961 (4)	0.6218 (3)	0.5307 (2)	0.0783 (10)
F7	0.2083 (4)	0.7050 (3)	0.5775 (2)	0.0724 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.069 (2)	0.0496 (17)	0.0622 (19)	−0.0210 (16)	0.0108 (16)	0.0033 (15)
O2	0.054 (2)	0.0340 (18)	0.0455 (19)	0.0052 (16)	0.0016 (16)	−0.0056 (15)
O4	0.0410 (19)	0.0330 (17)	0.0494 (19)	−0.0018 (15)	0.0165 (15)	0.0026 (14)
O6	0.0303 (17)	0.068 (2)	0.0468 (18)	−0.0098 (18)	0.0075 (14)	−0.0031 (18)
N1	0.037 (2)	0.037 (2)	0.039 (2)	−0.0083 (17)	0.0047 (17)	0.0009 (16)
N3	0.0305 (19)	0.036 (2)	0.0327 (18)	−0.0003 (18)	0.0047 (15)	−0.0029 (16)
N5	0.028 (2)	0.044 (2)	0.0297 (19)	0.0004 (18)	0.0042 (16)	0.0010 (16)
C2	0.036 (3)	0.039 (3)	0.027 (2)	−0.001 (2)	−0.0037 (19)	−0.0030 (18)
C4	0.034 (3)	0.040 (2)	0.0208 (19)	0.000 (2)	0.0008 (18)	0.0001 (18)
C6	0.031 (3)	0.053 (3)	0.027 (2)	0.001 (2)	−0.0004 (18)	0.002 (2)
C7	0.053 (4)	0.049 (3)	0.086 (4)	0.016 (3)	0.010 (3)	−0.016 (3)
C8	0.067 (4)	0.036 (3)	0.067 (3)	−0.002 (3)	0.025 (3)	−0.002 (3)
C9	0.037 (3)	0.086 (4)	0.087 (4)	0.005 (3)	0.020 (3)	−0.009 (3)
Sb1	0.0548 (2)	0.0476 (2)	0.02970 (16)	−0.00836 (19)	−0.00802 (13)	0.00297 (16)
F2	0.061 (2)	0.122 (3)	0.073 (2)	−0.047 (2)	−0.0221 (17)	0.033 (2)
F3	0.174 (4)	0.082 (3)	0.066 (2)	−0.044 (3)	−0.035 (2)	0.042 (2)
F4	0.168 (4)	0.075 (2)	0.052 (2)	0.032 (2)	−0.020 (2)	−0.0256 (17)
F5	0.0550 (18)	0.0594 (18)	0.0543 (17)	−0.0083 (15)	0.0017 (14)	0.0162 (14)
F6	0.073 (2)	0.107 (3)	0.0574 (19)	0.006 (2)	0.0167 (17)	−0.0204 (18)
F7	0.0533 (19)	0.100 (3)	0.0583 (19)	0.0218 (18)	−0.0133 (15)	−0.0114 (18)

Geometric parameters (Å, º)

F1—N1	1.353 (4)	C7—H7B	0.97
O2—C2	1.290 (5)	C7—H7C	0.97
O2—C7	1.466 (6)	C8—H8A	0.97
O4—C4	1.291 (5)	C8—H8B	0.97
O4—C8	1.454 (5)	C8—H8C	0.97
O6—C6	1.285 (5)	C9—H9A	0.97
O6—C9	1.463 (6)	C9—H9B	0.97
N1—C2	1.349 (6)	C9—H9C	0.97
N1—C6	1.356 (6)	Sb1—F3	1.845 (3)
N3—C2	1.291 (5)	Sb1—F6	1.846 (3)
N3—C4	1.344 (5)	Sb1—F4	1.852 (3)
N5—C4	1.327 (5)	Sb1—F5	1.853 (3)
N5—C6	1.292 (5)	Sb1—F2	1.860 (3)
C7—H7A	0.97	Sb1—F7	1.866 (3)
F1—N1—C2	119.2 (4)	H8A—C8—H8B	109.5
F1—N1—C6	119.2 (4)	O4—C8—H8C	109.5
C2—N1—C6	121.6 (4)	H8A—C8—H8C	109.5
C2—N3—C4	115.4 (4)	H8B—C8—H8C	109.5
C4—N5—C6	116.1 (4)	O6—C9—H9A	109.5
N1—C2—N3	120.2 (4)	O6—C9—H9B	109.5
N3—C4—N5	127.1 (4)	H9A—C9—H9B	109.5
N1—C6—N5	119.6 (4)	O6—C9—H9C	109.5
C2—O2—C7	116.1 (4)	H9A—C9—H9C	109.5
C4—O4—C8	117.7 (4)	H9B—C9—H9C	109.5
C6—O6—C9	116.0 (4)	F3—Sb1—F6	89.48 (18)
O2—C2—N3	124.9 (4)	F3—Sb1—F4	90.99 (19)
O2—C2—N1	114.9 (4)	F6—Sb1—F4	178.80 (18)
O4—C4—N5	119.7 (4)	F3—Sb1—F5	179.63 (19)
O4—C4—N3	113.2 (4)	F6—Sb1—F5	90.76 (15)
O6—C6—N5	125.4 (4)	F4—Sb1—F5	88.77 (16)
O6—C6—N1	115.0 (4)	F3—Sb1—F2	91.59 (17)
O2—C7—H7A	109.5	F6—Sb1—F2	91.05 (17)
O2—C7—H7B	109.5	F4—Sb1—F2	90.03 (19)
H7A—C7—H7B	109.5	F5—Sb1—F2	88.69 (13)
O2—C7—H7C	109.5	F3—Sb1—F7	90.16 (17)
H7A—C7—H7C	109.5	F6—Sb1—F7	88.07 (14)
H7B—C7—H7C	109.5	F4—Sb1—F7	90.83 (17)
O4—C8—H8A	109.5	F5—Sb1—F7	89.56 (14)
O4—C8—H8B	109.5	F2—Sb1—F7	178.03 (15)
C7—O2—C2—N3	1.5 (6)	C6—N5—C4—N3	−0.9 (6)
C7—O2—C2—N1	−179.1 (4)	C2—N3—C4—O4	−178.8 (4)
C4—N3—C2—O2	179.4 (4)	C2—N3—C4—N5	0.8 (6)
C4—N3—C2—N1	0.0 (5)	C9—O6—C6—N5	1.3 (6)
F1—N1—C2—O2	−2.3 (5)	C9—O6—C6—N1	−179.0 (4)
C6—N1—C2—O2	−180.0 (3)	C4—N5—C6—O6	−180.0 (4)
F1—N1—C2—N3	177.1 (3)	C4—N5—C6—N1	0.3 (6)
C6—N1—C2—N3	−0.5 (6)	C2—N1—C6—O6	−179.4 (4)
C8—O4—C4—N5	−1.0 (6)	F1—N1—C6—O6	3.0 (5)
C8—O4—C4—N3	178.6 (4)	C2—N1—C6—N5	0.4 (6)
C6—N5—C4—O4	178.6 (4)	F1—N1—C6—N5	−177.3 (4)