Poly[diaqua­[3,5-bis­(trifluoro­meth­yl)pyrazolido]potassium]

Phan, H.N.; Lerner, H.-W.; Bolte, M.

doi:10.1107/S1600536810027133

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m928

https://doi.org/10.1107/S1600536810027133

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Poly[diaqua[3,5-bis(trifluoromethyl)pyrazolido]potassium]

Hien Ngoc Phan,^a Hans-Wolfram Lerner ^a and Michael Bolte ^a ^*

^aInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 7 July 2010; accepted 8 July 2010; online 14 July 2010)

The asymmetric unit of the title compound, [K(C₅HF₆N₂)(H₂O)₂]_n, is composed of two 3,5-bis(trifluoromethyl)pyrazolide anions, two potassium cations and four water molecules. The water molecules and 3,5-bis(trifluoromethyl)pyrazolide anions act as bridges between the potassium cations. Each potassium cation is surrounded by four O atoms [K—O = 2.705 (3)–2.767 (3) Å] and four F atoms [K—F = 2.870 (7)–3.215 (13) Å]. The water molecules and the 3,5-bis(trifluoromethyl)pyrazolide anions are connected by O—H⋯N hydrogen bonds, forming layers in the ab plane. All –CF₃ groups show rotational disorder between two orientations each.

Related literature

For related literature on pyrazolides, see: Bieller et al. (2006 ).

Experimental

Crystal data

[K(C₅HF₆N₂)(H₂O)₂]
M_r = 278.21
Triclinic, $[P \overline 1]$
a = 9.7453 (9) Å
b = 9.8179 (10) Å
c = 12.5243 (14) Å
α = 67.756 (8)°
β = 78.178 (8)°
γ = 88.758 (8)°
V = 1083.53 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 173 K
0.41 × 0.40 × 0.38 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.802, T_max = 0.815
11313 measured reflections
4027 independent reflections
3316 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.124
S = 1.13
4027 reflections
425 parameters
704 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N11ⁱ	0.82 (2)	2.10 (2)	2.906 (4)	167 (4)
O1—H1B⋯N12ⁱⁱ	0.82 (2)	2.09 (2)	2.896 (4)	168 (4)
O2—H2A⋯N2	0.82 (2)	2.12 (1)	2.929 (4)	173 (5)
O2—H2B⋯N2ⁱⁱⁱ	0.81 (2)	2.07 (1)	2.879 (4)	173 (5)
O3—H3A⋯N12	0.82 (2)	2.05 (1)	2.868 (4)	173 (4)
O3—H3B⋯N1	0.82 (2)	2.09 (1)	2.910 (4)	177 (4)
O4—H4A⋯N11ⁱ	0.82 (2)	2.08 (1)	2.891 (4)	175 (4)
O4—H4B⋯N1ⁱ	0.82 (2)	2.07 (1)	2.884 (4)	174 (4)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810027133/cv2744sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027133/cv2744Isup2.hkl

checkCIF report

Comment top

Recently we have reported the structures of pyrazolides which possess substituents in a 3- or 4-position (Bieller et al., 2006). In this paper we report the synthesis and the crystal structure of the 3,5-substituted potassium pyrazolide [K(H₂O)₂][3,5-(CF₃)₂C₃HN₂] (I). The starting matrial for the synthesis of (I), 3,5-bis(trifluoromethyl)pyrazole, was prepared from hexafluoroacetylacetone CF₃COCH₂COCF₃ and hydrazine hydrate N₂H₄^.H₂O. By a following reaction of one equivalent of KH and one equivalent of 3,5-bis(trifluoromethyl)pyrazole in ethanol the potassium pyrazolide (I) was accessible in nearly quantitive yield.

The asymmetric unit of the title compound is composed of two 3,5-bis(trifluoromethyl)pyrazolide anions, two potassium cations and four water molecules. The water molecules and 3,5-bis(trifluoromethyl)pyrazolide anions act as bridges between the potassium cations. Each potassium cation is bonded to four O atoms and four F atoms. The K—O distances range from 2.705 (3)Å (K2—O4) to 2.767 (3)Å (K1—O3) and the K—F distances range from 2.870 (7)Å (K2—F162) to 3.215 (13)Å (K2—F17'). The water molecules and the 3,5-bis(trifluoromethyl)pyrazolide anions are connected by O—H···N hydrogen bonds forming layers in the ab plane The CF₃ groups show rotational disorder.

Related literature top

For related literature on pyrazolides, see: Bieller et al. (2006).

Experimental top

3,5-Bis(trifluoromethyl)pyrazole: Hydrazine hydrate N₂H₄^.H₂O (2.65 g, 52.87 mmol) and hexafluoroacetylacetone CF₃COCH₂COCF₃ (10.0 g, 6.8 ml, 48.06 mmol) were combined in ethanol (100 ml) under ambient conditions, forming a clear solution. The solution was heated under reflux for 5 h. After addition of a small amount of Na₂SO₄ the reaction mixture was heated again for 6 h. After removing the solvent pure, colorless 3,5-bis(trifluoromethyl)pyrazole was obtained by sublimation (373 K, normal pressure) in 79% yield.

Potassium 3,5-bis(trifluoromethyl)pyrazolide (I): To a slurry of KH (138 mg, 3.44 mmol) in 15 ml of tetrahydrofuran was added a solution of 3,5-bis(trifluoromethyl)pyrazole (820 mg, 4.02 mmol) in 15 ml tetrahydrofuran at 273 K. The resulting solution was allowed to warm up to room temperature. After removing the solvent in vacuo the obtained residue was recrystallized from wet tetrahydrofuran (yield 92%).

Structure description top

For related literature on pyrazolides, see: Bieller et al. (2006).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the asymmetric unit of the title compound with the atom numbering scheme; displacement ellipsoids are at the 50% probability level; H atoms are drawn as small spheres of arbitrary radii. Only major components of the disordered CF₃ groups are shown.
	Fig. 2. A portion of the packing diagram showing the layer structure. Only major components of the disordered CF₃ groups are shown.

Poly[diaqua[3,5-bis(trifluoromethyl)pyrazolido]potassium] top

Crystal data top

[K(C₅HF₆N₂)(H₂O)₂]	Z = 4
M_r = 278.21	F(000) = 552
Triclinic, P1	D_x = 1.705 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7453 (9) Å	Cell parameters from 10340 reflections
b = 9.8179 (10) Å	θ = 3.6–25.7°
c = 12.5243 (14) Å	µ = 0.56 mm⁻¹
α = 67.756 (8)°	T = 173 K
β = 78.178 (8)°	Block, colourless
γ = 88.758 (8)°	0.41 × 0.40 × 0.38 mm
V = 1083.53 (19) Å³

Data collection top

Stoe IPDS II two-circle diffractometer	4027 independent reflections
Radiation source: fine-focus sealed tube	3316 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 25.6°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −11→11
T_min = 0.802, T_max = 0.815	k = −11→11
11313 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0432P)² + 1.5007P] where P = (F_o² + 2F_c²)/3
4027 reflections	(Δ/σ)_max < 0.001
425 parameters	Δρ_max = 0.55 e Å⁻³
704 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[K(C₅HF₆N₂)(H₂O)₂]	γ = 88.758 (8)°
M_r = 278.21	V = 1083.53 (19) Å³
Triclinic, P1	Z = 4
a = 9.7453 (9) Å	Mo Kα radiation
b = 9.8179 (10) Å	µ = 0.56 mm⁻¹
c = 12.5243 (14) Å	T = 173 K
α = 67.756 (8)°	0.41 × 0.40 × 0.38 mm
β = 78.178 (8)°

Data collection top

Stoe IPDS II two-circle diffractometer	4027 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	3316 reflections with I > 2σ(I)
T_min = 0.802, T_max = 0.815	R_int = 0.039
11313 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	704 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.55 e Å⁻³
4027 reflections	Δρ_min = −0.34 e Å⁻³
425 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
K1	0.39698 (8)	0.67416 (8)	0.37909 (7)	0.0306 (2)
K2	0.08656 (8)	0.81180 (8)	0.61839 (8)	0.0317 (2)
O1	0.3599 (3)	0.8616 (3)	0.4958 (2)	0.0302 (6)
H1A	0.368 (5)	0.9497 (17)	0.455 (3)	0.036*
H1B	0.410 (4)	0.841 (5)	0.544 (3)	0.036*
O2	0.1232 (3)	0.6242 (3)	0.5002 (3)	0.0341 (6)
H2A	0.104 (5)	0.539 (2)	0.547 (3)	0.041*
H2B	0.075 (4)	0.630 (5)	0.453 (3)	0.041*
O3	0.3856 (3)	0.3788 (3)	0.5015 (2)	0.0298 (6)
H3A	0.407 (4)	0.337 (4)	0.456 (3)	0.036*
H3B	0.314 (3)	0.335 (4)	0.549 (3)	0.036*
O4	0.1246 (3)	1.1129 (3)	0.4996 (3)	0.0322 (6)
H4A	0.199 (3)	1.128 (5)	0.452 (3)	0.039*
H4B	0.128 (5)	1.152 (4)	0.546 (3)	0.039*
N1	0.1337 (3)	0.2318 (3)	0.6765 (3)	0.0326 (7)
N2	0.0336 (3)	0.3299 (3)	0.6808 (3)	0.0338 (7)
C3	−0.0136 (4)	0.3079 (4)	0.7954 (4)	0.0359 (9)
C4	0.0550 (4)	0.1969 (4)	0.8683 (4)	0.0378 (9)
H4	0.0428	0.1606	0.9518	0.045*
C5	0.1458 (4)	0.1523 (4)	0.7882 (3)	0.0306 (8)
C6	−0.1252 (5)	0.3993 (5)	0.8265 (4)	0.0512 (12)
C7	0.2477 (4)	0.0352 (5)	0.8098 (4)	0.0435 (10)
N11	0.3789 (3)	0.1607 (3)	0.3208 (3)	0.0332 (7)
N12	0.4741 (3)	0.2560 (3)	0.3258 (3)	0.0319 (7)
C13	0.5380 (4)	0.3394 (4)	0.2138 (3)	0.0287 (8)
C14	0.4871 (4)	0.3002 (4)	0.1328 (3)	0.0356 (9)
H14	0.5142	0.3398	0.0491	0.043*
C15	0.3864 (4)	0.1881 (4)	0.2058 (3)	0.0339 (8)
C16	0.6470 (4)	0.4559 (4)	0.1921 (3)	0.0367 (9)
C17	0.2902 (5)	0.1001 (5)	0.1750 (4)	0.0492 (11)
F61	−0.2511 (7)	0.3608 (16)	0.8164 (17)	0.083 (3)	0.69 (4)
F62	−0.141 (2)	0.3797 (16)	0.9412 (6)	0.083 (3)	0.69 (4)
F63	−0.1015 (14)	0.5433 (9)	0.7639 (14)	0.072 (3)	0.69 (4)
F61'	−0.233 (2)	0.413 (3)	0.768 (3)	0.064 (6)	0.31 (4)
F62'	−0.188 (3)	0.354 (2)	0.9391 (12)	0.062 (5)	0.31 (4)
F63'	−0.076 (3)	0.5390 (19)	0.796 (2)	0.053 (5)	0.31 (4)
F71	0.259 (2)	−0.040 (2)	0.7424 (16)	0.073 (4)	0.48 (3)
F72	0.3831 (9)	0.0999 (13)	0.7868 (15)	0.063 (4)	0.48 (3)
F73	0.2264 (18)	−0.053 (2)	0.9224 (9)	0.053 (3)	0.48 (3)
F71'	0.1992 (18)	−0.0831 (11)	0.7881 (14)	0.062 (3)	0.52 (3)
F72'	0.3724 (13)	0.0738 (14)	0.7403 (16)	0.085 (5)	0.52 (3)
F73'	0.2595 (19)	−0.0300 (18)	0.9222 (9)	0.048 (3)	0.52 (3)
F161	0.6176 (13)	0.5317 (19)	0.2597 (15)	0.074 (4)	0.56 (3)
F162	0.7721 (8)	0.3939 (10)	0.2141 (13)	0.060 (3)	0.56 (3)
F163	0.6807 (15)	0.5469 (16)	0.0798 (8)	0.056 (3)	0.56 (3)
F16'	0.5838 (12)	0.5759 (11)	0.2114 (14)	0.052 (3)	0.44 (3)
F16"	0.737 (2)	0.4186 (15)	0.2627 (18)	0.077 (5)	0.44 (3)
F16*	0.7155 (19)	0.5199 (18)	0.0808 (10)	0.051 (3)	0.44 (3)
F171	0.1522 (14)	0.085 (3)	0.240 (3)	0.072 (6)	0.31 (3)
F172	0.327 (3)	−0.0401 (16)	0.204 (2)	0.054 (5)	0.31 (3)
F173	0.276 (3)	0.147 (2)	0.0655 (13)	0.069 (5)	0.31 (3)
F17'	0.1599 (10)	0.1422 (15)	0.1863 (15)	0.083 (3)	0.69 (3)
F17"	0.2852 (16)	−0.0440 (8)	0.2354 (12)	0.071 (3)	0.69 (3)
F17*	0.3321 (18)	0.1236 (12)	0.0586 (5)	0.083 (3)	0.69 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0294 (4)	0.0256 (4)	0.0395 (5)	0.0024 (3)	−0.0082 (3)	−0.0150 (3)
K2	0.0276 (4)	0.0264 (4)	0.0422 (5)	0.0031 (3)	−0.0106 (3)	−0.0126 (4)
O1	0.0291 (13)	0.0230 (12)	0.0404 (16)	0.0028 (10)	−0.0151 (11)	−0.0101 (12)
O2	0.0285 (14)	0.0260 (13)	0.0490 (18)	0.0002 (11)	−0.0149 (12)	−0.0122 (13)
O3	0.0251 (13)	0.0299 (14)	0.0362 (16)	−0.0018 (10)	−0.0002 (11)	−0.0177 (12)
O4	0.0236 (13)	0.0334 (14)	0.0474 (18)	0.0031 (11)	−0.0082 (12)	−0.0238 (13)
N1	0.0297 (16)	0.0310 (16)	0.0386 (19)	0.0058 (13)	−0.0028 (13)	−0.0176 (15)
N2	0.0324 (16)	0.0315 (17)	0.0379 (19)	0.0099 (13)	−0.0064 (14)	−0.0147 (15)
C3	0.034 (2)	0.0299 (19)	0.038 (2)	−0.0014 (16)	0.0058 (16)	−0.0143 (17)
C4	0.047 (2)	0.034 (2)	0.027 (2)	0.0008 (17)	0.0003 (17)	−0.0107 (17)
C5	0.0298 (18)	0.0280 (19)	0.032 (2)	0.0000 (14)	−0.0046 (15)	−0.0102 (16)
C6	0.050 (3)	0.040 (2)	0.058 (3)	0.005 (2)	0.009 (2)	−0.022 (2)
C7	0.049 (3)	0.038 (2)	0.037 (2)	0.0113 (19)	−0.0088 (19)	−0.0077 (19)
N11	0.0379 (17)	0.0306 (16)	0.0335 (18)	−0.0010 (13)	−0.0097 (14)	−0.0134 (14)
N12	0.0391 (17)	0.0276 (16)	0.0333 (18)	0.0013 (13)	−0.0119 (14)	−0.0141 (14)
C13	0.0320 (18)	0.0254 (18)	0.0281 (19)	0.0057 (14)	−0.0059 (15)	−0.0101 (15)
C14	0.052 (2)	0.031 (2)	0.0240 (19)	0.0079 (17)	−0.0116 (17)	−0.0091 (16)
C15	0.047 (2)	0.0271 (19)	0.032 (2)	0.0101 (16)	−0.0173 (17)	−0.0121 (16)
C16	0.037 (2)	0.034 (2)	0.033 (2)	−0.0007 (16)	−0.0033 (17)	−0.0082 (18)
C17	0.065 (3)	0.041 (2)	0.052 (3)	0.005 (2)	−0.029 (2)	−0.019 (2)
F61	0.041 (3)	0.077 (5)	0.118 (7)	0.014 (3)	0.012 (4)	−0.040 (5)
F62	0.096 (7)	0.077 (5)	0.065 (4)	0.016 (5)	0.023 (3)	−0.038 (3)
F63	0.071 (5)	0.039 (3)	0.084 (6)	0.020 (3)	0.012 (4)	−0.015 (3)
F61'	0.045 (7)	0.082 (10)	0.084 (10)	0.027 (6)	−0.025 (6)	−0.048 (8)
F62'	0.057 (9)	0.052 (7)	0.050 (7)	0.007 (6)	0.033 (5)	−0.013 (5)
F63'	0.061 (8)	0.029 (6)	0.066 (9)	0.008 (5)	0.001 (6)	−0.021 (5)
F71	0.094 (8)	0.079 (7)	0.074 (7)	0.056 (6)	−0.040 (6)	−0.052 (6)
F72	0.033 (3)	0.061 (5)	0.068 (6)	0.009 (3)	0.001 (4)	0.000 (4)
F73	0.044 (6)	0.048 (6)	0.048 (5)	−0.003 (4)	−0.014 (3)	0.007 (4)
F71'	0.087 (7)	0.050 (4)	0.067 (6)	0.030 (4)	−0.036 (5)	−0.033 (4)
F72'	0.060 (5)	0.068 (5)	0.080 (7)	0.038 (4)	0.018 (5)	0.007 (5)
F73'	0.052 (7)	0.049 (5)	0.048 (4)	0.008 (4)	−0.027 (3)	−0.015 (3)
F161	0.070 (5)	0.080 (7)	0.084 (7)	−0.031 (4)	0.018 (5)	−0.061 (6)
F162	0.044 (3)	0.052 (4)	0.074 (6)	−0.004 (3)	−0.031 (3)	−0.004 (3)
F163	0.049 (5)	0.046 (5)	0.048 (4)	−0.002 (4)	−0.010 (3)	0.009 (3)
F16'	0.054 (5)	0.042 (4)	0.060 (6)	−0.006 (3)	0.005 (4)	−0.027 (4)
F16"	0.080 (7)	0.058 (5)	0.083 (8)	−0.026 (5)	−0.052 (7)	0.003 (5)
F16*	0.049 (7)	0.049 (6)	0.047 (5)	−0.006 (4)	0.016 (4)	−0.022 (4)
F171	0.046 (6)	0.090 (10)	0.094 (11)	−0.011 (6)	−0.009 (6)	−0.053 (8)
F172	0.067 (9)	0.030 (6)	0.073 (9)	−0.003 (5)	−0.029 (7)	−0.022 (5)
F173	0.082 (9)	0.069 (8)	0.056 (7)	−0.011 (6)	−0.054 (6)	−0.003 (5)
F17'	0.070 (4)	0.080 (5)	0.126 (7)	0.011 (3)	−0.064 (4)	−0.046 (5)
F17"	0.089 (6)	0.041 (3)	0.088 (6)	−0.010 (3)	−0.048 (5)	−0.013 (3)
F17*	0.126 (7)	0.085 (4)	0.062 (4)	−0.007 (5)	−0.049 (4)	−0.040 (3)

Geometric parameters (Å, º) top

K1—O3	2.711 (3)	C5—C7	1.486 (5)
K1—O1	2.729 (3)	C6—F62'	1.319 (12)
K1—O2	2.738 (3)	C6—F63	1.330 (8)
K1—O3ⁱ	2.767 (3)	C6—F61	1.336 (8)
K1—F16'	2.923 (9)	C6—F63'	1.347 (12)
K1—F72ⁱ	2.953 (8)	C6—F62	1.351 (8)
K1—F161	2.992 (10)	C6—F61'	1.382 (11)
K1—F17"ⁱⁱ	2.998 (7)	C7—F71	1.304 (8)
K1—F172ⁱⁱ	3.004 (14)	C7—F72'	1.309 (8)
K1—F61'ⁱⁱⁱ	3.016 (11)	C7—F73	1.321 (10)
K1—F72'ⁱ	3.078 (14)	C7—F73'	1.336 (10)
K1—F61ⁱⁱⁱ	3.196 (14)	C7—F71'	1.401 (9)
K1—H2B	3.08 (4)	C7—F72	1.403 (9)
K1—H3A	3.08 (4)	N11—C15	1.347 (5)
K2—O4^iv	2.705 (3)	N11—N12	1.359 (4)
K2—O1	2.739 (3)	N12—C13	1.349 (5)
K2—O2	2.745 (3)	C13—C14	1.391 (5)
K2—O4	2.754 (3)	C13—C16	1.486 (5)
K2—F162ⁱ	2.870 (7)	C14—C15	1.388 (6)
K2—F16"ⁱ	2.938 (13)	C14—H14	0.9500
K2—F63	2.972 (8)	C15—C17	1.487 (6)
K2—F63'	2.978 (15)	C16—F161	1.312 (7)
K2—F171ⁱⁱⁱ	3.026 (12)	C16—F16"	1.319 (9)
K2—F71'ⁱⁱ	3.075 (8)	C16—F163	1.325 (9)
K2—F71ⁱⁱ	3.199 (13)	C16—F16*	1.326 (10)
K2—F17'ⁱⁱⁱ	3.215 (13)	C16—F162	1.383 (7)
K2—H1A	3.05 (4)	C16—F16'	1.396 (8)
K2—H1B	3.08 (4)	C17—F173	1.309 (12)
K2—H4A	3.08 (4)	C17—F17'	1.323 (8)
O1—H1A	0.817 (12)	C17—F17"	1.324 (8)
O1—H1B	0.818 (12)	C17—F172	1.344 (12)
O2—H2A	0.817 (12)	C17—F17*	1.360 (8)
O2—H2B	0.813 (12)	C17—F171	1.401 (11)
O3—K1ⁱ	2.767 (3)	F61—K1ⁱⁱⁱ	3.196 (14)
O3—H3A	0.818 (12)	F61'—K1ⁱⁱⁱ	3.016 (11)
O3—H3B	0.819 (12)	F71—K2^v	3.199 (13)
O4—K2^iv	2.705 (3)	F72—K1ⁱ	2.953 (8)
O4—H4A	0.816 (12)	F71'—K2^v	3.075 (8)
O4—H4B	0.817 (12)	F72'—K1ⁱ	3.078 (14)
N1—C5	1.348 (5)	F162—K2ⁱ	2.870 (7)
N1—N2	1.363 (4)	F16"—K2ⁱ	2.938 (13)
N2—C3	1.349 (5)	F171—K2ⁱⁱⁱ	3.026 (12)
C3—C4	1.390 (6)	F172—K1^v	3.004 (14)
C3—C6	1.480 (6)	F17'—K2ⁱⁱⁱ	3.215 (13)
C4—C5	1.390 (5)	F17"—K1^v	2.998 (7)
C4—H4	0.9500

O3—K1—O1	120.18 (8)	F71'ⁱⁱ—K2—F17'ⁱⁱⁱ	67.3 (4)
O3—K1—O2	79.20 (8)	F71ⁱⁱ—K2—F17'ⁱⁱⁱ	78.5 (4)
O1—K1—O2	74.08 (8)	O4^iv—K2—H1A	110.8 (7)
O3—K1—O3ⁱ	73.56 (8)	O1—K2—H1A	15.0 (4)
O1—K1—O3ⁱ	75.98 (7)	O2—K2—H1A	82.4 (7)
O2—K1—O3ⁱ	120.62 (9)	O4—K2—H1A	60.0 (5)
O3—K1—F16'	78.1 (2)	F162ⁱ—K2—H1A	90.6 (6)
O1—K1—F16'	147.4 (2)	F16"ⁱ—K2—H1A	82.5 (6)
O2—K1—F16'	138.4 (2)	F63—K2—H1A	148.9 (6)
O3ⁱ—K1—F16'	85.3 (4)	F63'—K2—H1A	146.8 (7)
O3—K1—F72ⁱ	135.5 (3)	F171ⁱⁱⁱ—K2—H1A	135.2 (7)
O1—K1—F72ⁱ	83.5 (4)	F71'ⁱⁱ—K2—H1A	82.8 (9)
O2—K1—F72ⁱ	145.3 (3)	F71ⁱⁱ—K2—H1A	69.8 (9)
O3ⁱ—K1—F72ⁱ	77.4 (3)	F17'ⁱⁱⁱ—K2—H1A	142.1 (7)
F16'—K1—F72ⁱ	66.4 (4)	O4^iv—K2—H1B	134.5 (5)
O3—K1—F161	68.8 (3)	O1—K2—H1B	14.7 (5)
O1—K1—F161	142.8 (2)	O2—K2—H1B	81.1 (7)
O2—K1—F161	140.27 (17)	O4—K2—H1B	80.8 (8)
O3ⁱ—K1—F161	72.6 (4)	F162ⁱ—K2—H1B	65.2 (6)
F16'—K1—F161	14.2 (2)	F16"ⁱ—K2—H1B	57.7 (8)
F72ⁱ—K1—F161	70.7 (4)	F63—K2—H1B	128.9 (8)
O3—K1—F17"ⁱⁱ	154.3 (3)	F63'—K2—H1B	123.7 (9)
O1—K1—F17"ⁱⁱ	69.4 (3)	F171ⁱⁱⁱ—K2—H1B	140.6 (8)
O2—K1—F17"ⁱⁱ	81.3 (3)	F71'ⁱⁱ—K2—H1B	72.3 (7)
O3ⁱ—K1—F17"ⁱⁱ	131.5 (2)	F71ⁱⁱ—K2—H1B	61.4 (7)
F16'—K1—F17"ⁱⁱ	106.5 (5)	F17'ⁱⁱⁱ—K2—H1B	139.6 (6)
F72ⁱ—K1—F17"ⁱⁱ	66.0 (4)	H1A—K2—H1B	25.4 (8)
F161—K1—F17"ⁱⁱ	119.6 (5)	O4^iv—K2—H4A	81.5 (8)
O3—K1—F172ⁱⁱ	157.4 (5)	O1—K2—H4A	60.5 (5)
O1—K1—F172ⁱⁱ	74.9 (5)	O2—K2—H4A	110.9 (7)
O2—K1—F172ⁱⁱ	90.2 (5)	O4—K2—H4A	14.8 (5)
O3ⁱ—K1—F172ⁱⁱ	128.7 (5)	F162ⁱ—K2—H4A	125.7 (8)
F16'—K1—F172ⁱⁱ	97.7 (6)	F16"ⁱ—K2—H4A	123.9 (7)
F72ⁱ—K1—F172ⁱⁱ	58.1 (5)	F63—K2—H4A	163.1 (7)
F161—K1—F172ⁱⁱ	110.5 (6)	F63'—K2—H4A	167.5 (7)
F17"ⁱⁱ—K1—F172ⁱⁱ	9.5 (4)	F171ⁱⁱⁱ—K2—H4A	93.4 (7)
O3—K1—F61'ⁱⁱⁱ	83.0 (6)	F71'ⁱⁱ—K2—H4A	79.4 (9)
O1—K1—F61'ⁱⁱⁱ	135.1 (3)	F71ⁱⁱ—K2—H4A	68.9 (9)
O2—K1—F61'ⁱⁱⁱ	73.7 (6)	F17'ⁱⁱⁱ—K2—H4A	104.0 (6)
O3ⁱ—K1—F61'ⁱⁱⁱ	148.4 (3)	H1A—K2—H4A	45.5 (7)
F16'—K1—F61'ⁱⁱⁱ	69.2 (5)	H1B—K2—H4A	67.6 (9)
F72ⁱ—K1—F61'ⁱⁱⁱ	107.0 (8)	K1—O1—K2	106.24 (9)
F161—K1—F61'ⁱⁱⁱ	79.4 (5)	K1—O1—H1A	116 (3)
F17"ⁱⁱ—K1—F61'ⁱⁱⁱ	75.5 (6)	K2—O1—H1A	105 (3)
F172ⁱⁱ—K1—F61'ⁱⁱⁱ	74.8 (8)	K1—O1—H1B	110 (3)
O3—K1—F72'ⁱ	136.4 (2)	K2—O1—H1B	107 (3)
O1—K1—F72'ⁱ	71.0 (4)	H1A—O1—H1B	111 (4)
O2—K1—F72'ⁱ	139.7 (2)	K1—O2—K2	105.85 (9)
O3ⁱ—K1—F72'ⁱ	68.9 (4)	K1—O2—H2A	113 (3)
F16'—K1—F72'ⁱ	77.5 (4)	K2—O2—H2A	110 (3)
F72ⁱ—K1—F72'ⁱ	14.0 (2)	K1—O2—H2B	107 (3)
F161—K1—F72'ⁱ	79.4 (3)	K2—O2—H2B	119 (3)
F17"ⁱⁱ—K1—F72'ⁱ	68.2 (4)	H2A—O2—H2B	102 (4)
F172ⁱⁱ—K1—F72'ⁱ	62.0 (6)	K1—O3—K1ⁱ	106.44 (8)
F61'ⁱⁱⁱ—K1—F72'ⁱ	120.2 (9)	K1—O3—H3A	110 (3)
O3—K1—F61ⁱⁱⁱ	92.7 (3)	K1ⁱ—O3—H3A	103 (3)
O1—K1—F61ⁱⁱⁱ	132.49 (19)	K1—O3—H3B	121 (3)
O2—K1—F61ⁱⁱⁱ	80.5 (2)	K1ⁱ—O3—H3B	108 (3)
O3ⁱ—K1—F61ⁱⁱⁱ	150.58 (15)	H3A—O3—H3B	108 (4)
F16'—K1—F61ⁱⁱⁱ	66.2 (4)	K2^iv—O4—K2	105.09 (9)
F72ⁱ—K1—F61ⁱⁱⁱ	96.5 (5)	K2^iv—O4—H4A	109 (3)
F161—K1—F61ⁱⁱⁱ	78.2 (4)	K2—O4—H4A	106 (3)
F17"ⁱⁱ—K1—F61ⁱⁱⁱ	67.5 (4)	K2^iv—O4—H4B	116 (3)
F172ⁱⁱ—K1—F61ⁱⁱⁱ	65.6 (5)	K2—O4—H4B	110 (3)
F61'ⁱⁱⁱ—K1—F61ⁱⁱⁱ	11.0 (5)	H4A—O4—H4B	111 (5)
F72'ⁱ—K1—F61ⁱⁱⁱ	109.4 (5)	C5—N1—N2	107.6 (3)
O3—K1—H2B	83.5 (8)	C3—N2—N1	107.1 (3)
O1—K1—H2B	83.4 (7)	N2—C3—C4	111.6 (3)
O2—K1—H2B	14.6 (5)	N2—C3—C6	118.8 (4)
O3ⁱ—K1—H2B	134.9 (5)	C4—C3—C6	129.6 (4)
F16'—K1—H2B	127.6 (7)	C5—C4—C3	102.4 (3)
F72ⁱ—K1—H2B	139.6 (8)	C5—C4—H4	128.8
F161—K1—H2B	133.5 (8)	C3—C4—H4	128.8
F17"ⁱⁱ—K1—H2B	73.7 (8)	N1—C5—C4	111.3 (3)
F172ⁱⁱ—K1—H2B	81.7 (9)	N1—C5—C7	119.1 (3)
F61'ⁱⁱⁱ—K1—H2B	60.1 (7)	C4—C5—C7	129.6 (4)
F72'ⁱ—K1—H2B	139.5 (8)	F62'—C6—F63	118.9 (12)
F61ⁱⁱⁱ—K1—H2B	66.2 (5)	F62'—C6—F61	82.4 (10)
O3—K1—H3A	14.5 (5)	F63—C6—F61	107.1 (6)
O1—K1—H3A	134.5 (5)	F62'—C6—F63'	105.6 (11)
O2—K1—H3A	87.1 (7)	F63—C6—F62	106.9 (7)
O3ⁱ—K1—H3A	79.2 (8)	F61—C6—F62	104.9 (6)
F16'—K1—H3A	64.9 (6)	F62'—C6—F61'	104.8 (9)
F72ⁱ—K1—H3A	127.0 (7)	F63'—C6—F61'	104.6 (10)
F161—K1—H3A	57.1 (7)	F62'—C6—C3	116.1 (11)
F17"ⁱⁱ—K1—H3A	148.8 (8)	F63—C6—C3	114.6 (6)
F172ⁱⁱ—K1—H3A	147.5 (8)	F61—C6—C3	112.7 (5)
F61'ⁱⁱⁱ—K1—H3A	73.4 (9)	F63'—C6—C3	111.6 (12)
F72'ⁱ—K1—H3A	132.1 (8)	F62—C6—C3	110.0 (6)
F61ⁱⁱⁱ—K1—H3A	82.1 (7)	F61'—C6—C3	113.1 (8)
H2B—K1—H3A	88.1 (11)	F71—C7—F73	111.2 (9)
O4^iv—K2—O1	119.89 (9)	F72'—C7—F73'	110.1 (8)
O4^iv—K2—O2	79.81 (8)	F72'—C7—F71'	104.3 (7)
O1—K2—O2	73.82 (8)	F73'—C7—F71'	101.9 (7)
O4^iv—K2—O4	74.91 (9)	F71—C7—F72	104.5 (7)
O1—K2—O4	74.86 (8)	F73—C7—F72	103.4 (7)
O2—K2—O4	121.46 (9)	F71—C7—C5	115.6 (5)
O4^iv—K2—F162ⁱ	152.75 (19)	F72'—C7—C5	115.0 (5)
O1—K2—F162ⁱ	78.0 (2)	F73—C7—C5	111.8 (9)
O2—K2—F162ⁱ	86.8 (3)	F73'—C7—C5	114.7 (8)
O4—K2—F162ⁱ	132.0 (2)	F71'—C7—C5	109.6 (5)
O4^iv—K2—F16"ⁱ	148.2 (3)	F72—C7—C5	109.3 (6)
O1—K2—F16"ⁱ	68.5 (4)	C15—N11—N12	107.1 (3)
O2—K2—F16"ⁱ	73.4 (5)	C13—N12—N11	107.4 (3)
O4—K2—F16"ⁱ	134.2 (2)	N12—C13—C14	111.5 (3)
F162ⁱ—K2—F16"ⁱ	14.9 (3)	N12—C13—C16	119.3 (3)
O4^iv—K2—F63	82.9 (4)	C14—C13—C16	129.2 (3)
O1—K2—F63	134.4 (2)	C15—C14—C13	102.1 (3)
O2—K2—F63	72.5 (3)	C15—C14—H14	129.0
O4—K2—F63	150.2 (3)	C13—C14—H14	129.0
F162ⁱ—K2—F63	70.4 (4)	N11—C15—C14	111.9 (3)
F16"ⁱ—K2—F63	73.0 (4)	N11—C15—C17	118.3 (4)
O4^iv—K2—F63'	91.8 (6)	C14—C15—C17	129.8 (4)
O1—K2—F63'	131.8 (6)	F161—C16—F16"	74.0 (7)
O2—K2—F63'	78.0 (5)	F161—C16—F163	109.9 (8)
O4—K2—F63'	152.7 (5)	F161—C16—F16*	120.8 (10)
F162ⁱ—K2—F63'	62.0 (6)	F16"—C16—F16*	110.0 (8)
F16"ⁱ—K2—F63'	66.3 (7)	F161—C16—F162	104.9 (6)
F63—K2—F63'	9.8 (4)	F163—C16—F162	103.5 (6)
O4^iv—K2—F171ⁱⁱⁱ	70.5 (5)	F16"—C16—F16'	103.7 (7)
O1—K2—F171ⁱⁱⁱ	147.0 (3)	F16*—C16—F16'	101.1 (7)
O2—K2—F171ⁱⁱⁱ	138.2 (3)	F161—C16—C13	114.8 (5)
O4—K2—F171ⁱⁱⁱ	78.8 (6)	F16"—C16—C13	115.6 (5)
F162ⁱ—K2—F171ⁱⁱⁱ	106.5 (7)	F163—C16—C13	112.7 (7)
F16"ⁱ—K2—F171ⁱⁱⁱ	120.8 (9)	F16*—C16—C13	114.9 (9)
F63—K2—F171ⁱⁱⁱ	75.2 (5)	F162—C16—C13	110.3 (5)
F63'—K2—F171ⁱⁱⁱ	74.3 (7)	F16'—C16—C13	110.0 (5)
O4^iv—K2—F71'ⁱⁱ	135.0 (2)	F17'—C17—F17"	107.7 (6)
O1—K2—F71'ⁱⁱ	84.2 (4)	F173—C17—F172	106.8 (12)
O2—K2—F71'ⁱⁱ	145.2 (2)	F17'—C17—F17*	104.7 (6)
O4—K2—F71'ⁱⁱ	76.3 (2)	F17"—C17—F17*	107.3 (7)
F162ⁱ—K2—F71'ⁱⁱ	62.0 (3)	F173—C17—F171	103.8 (9)
F16"ⁱ—K2—F71'ⁱⁱ	73.6 (4)	F172—C17—F171	103.0 (9)
F63—K2—F71'ⁱⁱ	107.6 (5)	F173—C17—C15	118.0 (9)
F63'—K2—F71'ⁱⁱ	98.4 (6)	F17'—C17—C15	112.7 (5)
F171ⁱⁱⁱ—K2—F71'ⁱⁱ	70.4 (5)	F17"—C17—C15	114.7 (6)
O4^iv—K2—F71ⁱⁱ	136.31 (19)	F172—C17—C15	111.1 (11)
O1—K2—F71ⁱⁱ	72.3 (4)	F17*—C17—C15	109.0 (6)
O2—K2—F71ⁱⁱ	140.0 (2)	F171—C17—C15	112.9 (8)
O4—K2—F71ⁱⁱ	68.3 (3)	C6—F61—K1ⁱⁱⁱ	139.0 (9)
F162ⁱ—K2—F71ⁱⁱ	66.0 (4)	C6—F63—K2	152.7 (9)
F16"ⁱ—K2—F71ⁱⁱ	75.0 (4)	C6—F61'—K1ⁱⁱⁱ	153.2 (11)
F63—K2—F71ⁱⁱ	119.9 (6)	C6—F63'—K2	149.8 (16)
F63'—K2—F71ⁱⁱ	110.4 (7)	C7—F71—K2^v	144.1 (11)
F171ⁱⁱⁱ—K2—F71ⁱⁱ	79.7 (5)	C7—F72—K1ⁱ	147.6 (8)
F71'ⁱⁱ—K2—F71ⁱⁱ	13.2 (2)	C7—F71'—K2^v	147.7 (7)
O4^iv—K2—F17'ⁱⁱⁱ	78.53 (18)	C7—F72'—K1ⁱ	143.7 (12)
O1—K2—F17'ⁱⁱⁱ	150.29 (16)	C16—F161—K1	146.9 (10)
O2—K2—F17'ⁱⁱⁱ	135.21 (19)	C16—F162—K2ⁱ	146.9 (8)
O4—K2—F17'ⁱⁱⁱ	89.6 (3)	C16—F16'—K1	145.8 (8)
F162ⁱ—K2—F17'ⁱⁱⁱ	95.1 (4)	C16—F16"—K2ⁱ	145.9 (13)
F16"ⁱ—K2—F17'ⁱⁱⁱ	109.1 (6)	C17—F171—K2ⁱⁱⁱ	151.7 (11)
F63—K2—F17'ⁱⁱⁱ	66.3 (4)	C17—F172—K1^v	151.2 (16)
F63'—K2—F17'ⁱⁱⁱ	64.1 (6)	C17—F17'—K2ⁱⁱⁱ	139.8 (8)
F171ⁱⁱⁱ—K2—F17'ⁱⁱⁱ	12.2 (5)	C17—F17"—K1^v	154.6 (8)

O3—K1—O1—K2	−66.68 (11)	F61'—C6—F61—K1ⁱⁱⁱ	40 (2)
O2—K1—O1—K2	0.29 (9)	C3—C6—F61—K1ⁱⁱⁱ	−56.9 (15)
O3ⁱ—K1—O1—K2	−127.82 (10)	F62'—C6—F63—K2	119 (3)
F16'—K1—O1—K2	175.4 (6)	F61—C6—F63—K2	−151 (3)
F72ⁱ—K1—O1—K2	153.5 (2)	F63'—C6—F63—K2	62 (4)
F161—K1—O1—K2	−160.9 (7)	F62—C6—F63—K2	97 (3)
F17"ⁱⁱ—K1—O1—K2	86.8 (3)	F61'—C6—F63—K2	−138 (3)
F172ⁱⁱ—K1—O1—K2	94.9 (5)	C3—C6—F63—K2	−25 (3)
F61'ⁱⁱⁱ—K1—O1—K2	45.9 (10)	O4^iv—K2—F63—C6	143 (3)
F72'ⁱ—K1—O1—K2	160.0 (4)	O1—K2—F63—C6	18 (3)
F61ⁱⁱⁱ—K1—O1—K2	60.8 (4)	O2—K2—F63—C6	62 (3)
O4^iv—K2—O1—K1	−68.00 (11)	O4—K2—F63—C6	−175 (2)
O2—K2—O1—K1	−0.29 (9)	F162ⁱ—K2—F63—C6	−31 (3)
O4—K2—O1—K1	−130.19 (10)	F16"ⁱ—K2—F63—C6	−16 (3)
F162ⁱ—K2—O1—K1	89.8 (3)	F63'—K2—F63—C6	−61 (4)
F16"ⁱ—K2—O1—K1	77.8 (4)	F171ⁱⁱⁱ—K2—F63—C6	−145 (3)
F63—K2—O1—K1	43.4 (6)	F71'ⁱⁱ—K2—F63—C6	−82 (3)
F63'—K2—O1—K1	56.3 (7)	F71ⁱⁱ—K2—F63—C6	−76 (3)
F171ⁱⁱⁱ—K2—O1—K1	−168.3 (12)	F17'ⁱⁱⁱ—K2—F63—C6	−136 (3)
F71'ⁱⁱ—K2—O1—K1	152.4 (2)	F62'—C6—F61'—K1ⁱⁱⁱ	−113 (5)
F71ⁱⁱ—K2—O1—K1	158.2 (3)	F63—C6—F61'—K1ⁱⁱⁱ	128 (5)
F17'ⁱⁱⁱ—K2—O1—K1	169.0 (5)	F61—C6—F61'—K1ⁱⁱⁱ	−81 (5)
O3—K1—O2—K2	125.63 (10)	F63'—C6—F61'—K1ⁱⁱⁱ	136 (5)
O1—K1—O2—K2	−0.29 (9)	F62—C6—F61'—K1ⁱⁱⁱ	−125 (5)
O3ⁱ—K1—O2—K2	62.23 (12)	C3—C6—F61'—K1ⁱⁱⁱ	14 (5)
F16'—K1—O2—K2	−176.3 (5)	F62'—C6—F63'—K2	176 (4)
F72ⁱ—K1—O2—K2	−52.0 (7)	F63—C6—F63'—K2	−54 (3)
F161—K1—O2—K2	162.0 (7)	F61—C6—F63'—K2	−93 (4)
F17"ⁱⁱ—K1—O2—K2	−71.3 (3)	F62—C6—F63'—K2	160 (4)
F172ⁱⁱ—K1—O2—K2	−74.5 (5)	F61'—C6—F63'—K2	−74 (4)
F61'ⁱⁱⁱ—K1—O2—K2	−148.6 (6)	C3—C6—F63'—K2	49 (4)
F72'ⁱ—K1—O2—K2	−30.8 (7)	O4^iv—K2—F63'—C6	76 (4)
F61ⁱⁱⁱ—K1—O2—K2	−139.7 (3)	O1—K2—F63'—C6	−58 (4)
O4^iv—K2—O2—K1	125.69 (10)	O2—K2—F63'—C6	−3 (4)
O1—K2—O2—K1	0.29 (9)	O4—K2—F63'—C6	136 (3)
O4—K2—O2—K1	60.53 (12)	F162ⁱ—K2—F63'—C6	−95 (4)
F162ⁱ—K2—O2—K1	−78.2 (2)	F16"ⁱ—K2—F63'—C6	−80 (4)
F16"ⁱ—K2—O2—K1	−71.6 (4)	F63—K2—F63'—C6	52 (3)
F63—K2—O2—K1	−148.6 (4)	F171ⁱⁱⁱ—K2—F63'—C6	146 (4)
F63'—K2—O2—K1	−140.2 (6)	F71'ⁱⁱ—K2—F63'—C6	−148 (4)
F171ⁱⁱⁱ—K2—O2—K1	170.5 (10)	F71ⁱⁱ—K2—F63'—C6	−142 (3)
F71'ⁱⁱ—K2—O2—K1	−52.8 (6)	F17'ⁱⁱⁱ—K2—F63'—C6	153 (4)
F71ⁱⁱ—K2—O2—K1	−32.7 (7)	F72'—C7—F71—K2^v	−150 (3)
F17'ⁱⁱⁱ—K2—O2—K1	−172.2 (3)	F73—C7—F71—K2^v	90 (2)
O1—K1—O3—K1ⁱ	−62.37 (11)	F73'—C7—F71—K2^v	106 (2)
O2—K1—O3—K1ⁱ	−126.65 (10)	F71'—C7—F71—K2^v	46.7 (18)
O3ⁱ—K1—O3—K1ⁱ	0.0	F72—C7—F71—K2^v	−159 (2)
F16'—K1—O3—K1ⁱ	88.5 (3)	C5—C7—F71—K2^v	−39 (3)
F72ⁱ—K1—O3—K1ⁱ	51.4 (5)	F71—C7—F72—K1ⁱ	73 (2)
F161—K1—O3—K1ⁱ	77.3 (4)	F72'—C7—F72—K1ⁱ	55.2 (18)
F17"ⁱⁱ—K1—O3—K1ⁱ	−168.1 (7)	F73—C7—F72—K1ⁱ	−171 (2)
F172ⁱⁱ—K1—O3—K1ⁱ	169.9 (13)	F73'—C7—F72—K1ⁱ	−166 (2)
F61'ⁱⁱⁱ—K1—O3—K1ⁱ	158.6 (5)	F71'—C7—F72—K1ⁱ	90 (2)
F72'ⁱ—K1—O3—K1ⁱ	31.3 (7)	C5—C7—F72—K1ⁱ	−51 (2)
F61ⁱⁱⁱ—K1—O3—K1ⁱ	153.52 (18)	F71—C7—F71'—K2^v	−56.2 (17)
O4^iv—K2—O4—K2^iv	0.0	F72'—C7—F71'—K2^v	−72 (2)
O1—K2—O4—K2^iv	127.42 (11)	F73—C7—F71'—K2^v	164 (2)
O2—K2—O4—K2^iv	67.68 (11)	F73'—C7—F71'—K2^v	173 (2)
F162ⁱ—K2—O4—K2^iv	−174.8 (4)	F72—C7—F71'—K2^v	−91 (2)
F16"ⁱ—K2—O4—K2^iv	165.0 (7)	C5—C7—F71'—K2^v	51 (2)
F63—K2—O4—K2^iv	−43.3 (8)	F71—C7—F72'—K1ⁱ	152 (3)
F63'—K2—O4—K2^iv	−63.2 (12)	F73—C7—F72'—K1ⁱ	−102 (2)
F171ⁱⁱⁱ—K2—O4—K2^iv	−72.7 (5)	F73'—C7—F72'—K1ⁱ	−91 (2)
F71'ⁱⁱ—K2—O4—K2^iv	−145.0 (4)	F71'—C7—F72'—K1ⁱ	161 (2)
F71ⁱⁱ—K2—O4—K2^iv	−156.0 (4)	F72—C7—F72'—K1ⁱ	−45.6 (19)
F17'ⁱⁱⁱ—K2—O4—K2^iv	−78.21 (16)	C5—C7—F72'—K1ⁱ	41 (3)
C5—N1—N2—C3	−0.2 (4)	F16"—C16—F161—K1	−150 (3)
N1—N2—C3—C4	0.7 (4)	F163—C16—F161—K1	89 (2)
N1—N2—C3—C6	−179.3 (3)	F16*—C16—F161—K1	106 (2)
N2—C3—C4—C5	−0.9 (4)	F162—C16—F161—K1	−160 (2)
C6—C3—C4—C5	179.1 (4)	F16'—C16—F161—K1	49 (2)
N2—N1—C5—C4	−0.4 (4)	C13—C16—F161—K1	−39 (3)
N2—N1—C5—C7	179.5 (3)	O3—K1—F161—C16	79 (2)
C3—C4—C5—N1	0.8 (4)	O1—K1—F161—C16	−168.4 (17)
C3—C4—C5—C7	−179.2 (4)	O2—K1—F161—C16	41 (3)
N2—C3—C6—F62'	166.4 (16)	O3ⁱ—K1—F161—C16	158 (2)
C4—C3—C6—F62'	−13.6 (17)	F16'—K1—F161—C16	−50.1 (19)
N2—C3—C6—F63	−49.0 (12)	F72ⁱ—K1—F161—C16	−120 (2)
C4—C3—C6—F63	131.0 (11)	F17"ⁱⁱ—K1—F161—C16	−74 (2)
N2—C3—C6—F61	73.8 (10)	F172ⁱⁱ—K1—F161—C16	−77 (2)
C4—C3—C6—F61	−106.2 (11)	F61'ⁱⁱⁱ—K1—F161—C16	−7 (2)
N2—C3—C6—F63'	−72.5 (15)	F72'ⁱ—K1—F161—C16	−131 (2)
C4—C3—C6—F63'	107.5 (14)	F61ⁱⁱⁱ—K1—F161—C16	−18 (2)
N2—C3—C6—F62	−169.4 (10)	F161—C16—F162—K2ⁱ	67 (2)
C4—C3—C6—F62	10.6 (11)	F16"—C16—F162—K2ⁱ	48.6 (15)
N2—C3—C6—F61'	45.1 (18)	F163—C16—F162—K2ⁱ	−178.1 (18)
C4—C3—C6—F61'	−134.9 (18)	F16*—C16—F162—K2ⁱ	−172.5 (16)
N1—C5—C7—F71	−37.7 (14)	F16'—C16—F162—K2ⁱ	86.4 (18)
C4—C5—C7—F71	142.3 (14)	C13—C16—F162—K2ⁱ	−57.4 (17)
N1—C5—C7—F72'	46.2 (14)	F161—C16—F16'—K1	−49.2 (15)
C4—C5—C7—F72'	−133.9 (14)	F16"—C16—F16'—K1	−68 (2)
N1—C5—C7—F73	−166.2 (10)	F163—C16—F16'—K1	168.2 (18)
C4—C5—C7—F73	13.7 (11)	F16*—C16—F16'—K1	178 (2)
N1—C5—C7—F73'	175.3 (9)	F162—C16—F16'—K1	−88.0 (19)
C4—C5—C7—F73'	−4.7 (10)	C13—C16—F16'—K1	55.9 (19)
N1—C5—C7—F71'	−70.8 (9)	O3—K1—F16'—C16	−2.9 (16)
C4—C5—C7—F71'	109.1 (9)	O1—K1—F16'—C16	125.8 (13)
N1—C5—C7—F72	79.8 (9)	O2—K1—F16'—C16	−61 (2)
C4—C5—C7—F72	−100.2 (10)	O3ⁱ—K1—F16'—C16	71.3 (17)
C15—N11—N12—C13	−0.1 (4)	F72ⁱ—K1—F16'—C16	149.6 (19)
N11—N12—C13—C14	−0.4 (4)	F161—K1—F16'—C16	44.6 (13)
N11—N12—C13—C16	179.1 (3)	F17"ⁱⁱ—K1—F16'—C16	−156.8 (17)
N12—C13—C14—C15	0.7 (4)	F172ⁱⁱ—K1—F16'—C16	−160.3 (18)
C16—C13—C14—C15	−178.7 (4)	F61'ⁱⁱⁱ—K1—F16'—C16	−89.8 (18)
N12—N11—C15—C14	0.6 (4)	F72'ⁱ—K1—F16'—C16	140.7 (18)
N12—N11—C15—C17	−178.8 (3)	F61ⁱⁱⁱ—K1—F16'—C16	−101.3 (17)
C13—C14—C15—N11	−0.8 (4)	F161—C16—F16"—K2ⁱ	153 (3)
C13—C14—C15—C17	178.5 (4)	F163—C16—F16"—K2ⁱ	−104 (2)
N12—C13—C16—F161	−40.9 (13)	F16*—C16—F16"—K2ⁱ	−90 (2)
C14—C13—C16—F161	138.5 (12)	F162—C16—F16"—K2ⁱ	−46 (2)
N12—C13—C16—F16"	42.5 (15)	F16'—C16—F16"—K2ⁱ	163 (2)
C14—C13—C16—F16"	−138.1 (15)	C13—C16—F16"—K2ⁱ	42 (3)
N12—C13—C16—F163	−167.7 (8)	F173—C17—F171—K2ⁱⁱⁱ	−104 (4)
C14—C13—C16—F163	11.8 (9)	F17'—C17—F171—K2ⁱⁱⁱ	−71 (4)
N12—C13—C16—F16*	172.3 (9)	F17"—C17—F171—K2ⁱⁱⁱ	139 (4)
C14—C13—C16—F16*	−8.2 (11)	F172—C17—F171—K2ⁱⁱⁱ	145 (4)
N12—C13—C16—F162	77.3 (8)	F17*—C17—F171—K2ⁱⁱⁱ	−115 (4)
C14—C13—C16—F162	−103.3 (8)	C15—C17—F171—K2ⁱⁱⁱ	25 (5)
N12—C13—C16—F16'	−74.5 (9)	F173—C17—F172—K1^v	−177 (3)
C14—C13—C16—F16'	105.0 (9)	F17'—C17—F172—K1^v	−89 (4)
N11—C15—C17—F173	165.3 (15)	F17"—C17—F172—K1^v	−51 (3)
C14—C15—C17—F173	−14.0 (16)	F17*—C17—F172—K1^v	163 (3)
N11—C15—C17—F17'	75.8 (9)	F171—C17—F172—K1^v	−68 (4)
C14—C15—C17—F17'	−103.5 (9)	C15—C17—F172—K1^v	53 (3)
N11—C15—C17—F17"	−48.0 (10)	F173—C17—F17'—K2ⁱⁱⁱ	−171.6 (16)
C14—C15—C17—F17"	132.7 (9)	F17"—C17—F17'—K2ⁱⁱⁱ	71.9 (14)
N11—C15—C17—F172	−70.9 (13)	F172—C17—F17'—K2ⁱⁱⁱ	85.4 (18)
C14—C15—C17—F172	109.8 (13)	F17*—C17—F17'—K2ⁱⁱⁱ	−174.0 (10)
N11—C15—C17—F17*	−168.3 (8)	F171—C17—F17'—K2ⁱⁱⁱ	40.8 (17)
C14—C15—C17—F17*	12.3 (9)	C15—C17—F17'—K2ⁱⁱⁱ	−55.7 (14)
N11—C15—C17—F171	44.2 (16)	F173—C17—F17"—K1^v	123 (3)
C14—C15—C17—F171	−135.2 (16)	F17'—C17—F17"—K1^v	−150 (2)
F62'—C6—F61—K1ⁱⁱⁱ	−172.1 (17)	F172—C17—F17"—K1^v	62 (4)
F63—C6—F61—K1ⁱⁱⁱ	70.0 (16)	F17*—C17—F17"—K1^v	98 (3)
F63'—C6—F61—K1ⁱⁱⁱ	84.2 (19)	F171—C17—F17"—K1^v	−135 (3)
F62—C6—F61—K1ⁱⁱⁱ	−176.6 (12)	C15—C17—F17"—K1^v	−23 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x, −y+1, −z+1; (iv) −x, −y+2, −z+1; (v) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N11ⁱⁱ	0.82 (2)	2.10 (2)	2.906 (4)	167 (4)
O1—H1B···N12ⁱ	0.82 (2)	2.09 (2)	2.896 (4)	168 (4)
O2—H2A···N2	0.82 (2)	2.12 (1)	2.929 (4)	173 (5)
O2—H2B···N2ⁱⁱⁱ	0.81 (2)	2.07 (1)	2.879 (4)	173 (5)
O3—H3A···N12	0.82 (2)	2.05 (1)	2.868 (4)	173 (4)
O3—H3B···N1	0.82 (2)	2.09 (1)	2.910 (4)	177 (4)
O4—H4A···N11ⁱⁱ	0.82 (2)	2.08 (1)	2.891 (4)	175 (4)
O4—H4B···N1ⁱⁱ	0.82 (2)	2.07 (1)	2.884 (4)	174 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[K(C₅HF₆N₂)(H₂O)₂]
M_r	278.21
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.7453 (9), 9.8179 (10), 12.5243 (14)
α, β, γ (°)	67.756 (8), 78.178 (8), 88.758 (8)
V (Å³)	1083.53 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.41 × 0.40 × 0.38

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.802, 0.815
No. of measured, independent and observed [I > 2σ(I)] reflections	11313, 4027, 3316
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.124, 1.13
No. of reflections	4027
No. of parameters	425
No. of restraints	704
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.34

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N11ⁱ	0.82 (2)	2.104 (16)	2.906 (4)	167 (4)
O1—H1B···N12ⁱⁱ	0.82 (2)	2.090 (15)	2.896 (4)	168 (4)
O2—H2A···N2	0.82 (2)	2.117 (14)	2.929 (4)	173 (5)
O2—H2B···N2ⁱⁱⁱ	0.81 (2)	2.071 (14)	2.879 (4)	173 (5)
O3—H3A···N12	0.82 (2)	2.054 (14)	2.868 (4)	173 (4)
O3—H3B···N1	0.82 (2)	2.092 (13)	2.910 (4)	177 (4)
O4—H4A···N11ⁱ	0.82 (2)	2.076 (13)	2.891 (4)	175 (4)
O4—H4B···N1ⁱ	0.82 (2)	2.070 (13)	2.884 (4)	174 (4)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1.

References

Bieller, S., Haghiri, A., Bolte, M., Bats, J. W., Wagner, M. & Lerner, H.-W. (2006). Inorg. Chim. Acta, 359, 1559–1572. Web of Science CSD CrossRef CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar

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