Acta Crystallographica Section E: Structure Reports Online

Acta Crystallogr Sect E Struct Rep Online. 65(Pt 2): m171-m171

(18-Crown-6-κ⁶ O)(pyrazolato-κ² N,N′)-potassium(I)

Kerstin Kunza, Hans-Wolfram Lernera, Michael Boltea*

a. Institut für Anorganische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany

Correspondence e-mail: bolte@chemie.uni-frankfurt.de

© Kunz et al. 2009

DOI: 10.1107/S1600536808043237

Published online: 10 January 2009

Abstract

The asymmetric unit of the title compound, [K(C₃H₃N₂)(C₁₂H₂₄O₆)], is composed of a potassium cation bonded to the six O atoms of a crown ether molecule and the two N atoms of a pyrazolate anion. The K⋯O distances range from 2.8416 (8) to 3.0025 (8) Å, and the two K⋯N distances are 2.7441 (11) and 2.7654 (11) Å. The K cation is displaced by 0.8437 (4) Å from the best plane through the six O atoms. The latter plane is almost perpendicular to the plane of the pyrazolate ring [dihedral angle 83.93 (3)°].

Related literature

For related literature on scorpionate complexes, see: Bieller et al. (2006 ▶); Morawitz et al. (2008 ▶); Trofimenko (1993 ▶).

Experimental

Crystal data

[K(C₃H₃N₂)(C₁₂H₂₄O₆)]

M r = 370.49

Monoclinic,

a = 11.5330 (6) Å

b = 8.2369 (5) Å

c = 20.7622 (10) Å

β = 101.612 (4)°

V = 1931.96 (18) Å³

Z = 4

Mo Kα radiation

μ = 0.31 mm⁻¹

T = 173 (2) K

0.25 × 0.12 × 0.12 mm

Data collection

STOE IPDS II two-circle-diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.919, T max = 0.966

23118 measured reflections

3602 independent reflections

3234 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.026

wR(F ²) = 0.066

S = 1.03

3602 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å⁻³

Δρmin = −0.20 e Å⁻³

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 in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2281).

supplementary crystallographic information

Comment

We report here the X-ray crystal structure analysis of the potassium pyrazolide as complex with 18-crown-6, [K(18-crown-6)(C₃H₃N₂)] or [K(18-crown-6)(pz)]. Following the first synthesis of a scorpionate complex, considerable progress has been made towards extending this area of chemistry (Trofimenko, 1993). Our studies have shown that an important factor influencing the stability of scorpionates appears to be the degree of steric crowding around the boron centre. The results of investigations in our group show that the scorpionates RB(3–R'pz)₃⁻ and RB(4–R'pz)₃⁻ decompose in the presence of transition metal salts much more easily when R and R' are bulky (Bieller et al., 2006; Morawitz et al., 2008). Now we have found that irradiation of Mn(C₅H₃)(Bpz₃)₂(THF)₂ (I) in the presence of 18-crown-6 leads to the formation of potassium pyrazolide (II).

The asymmetric unit of the title compound, [C₁₂H₂₄O₆]K⁺[C₃H₃N₂]⁻, is composed of a potassium cation bonded to the six O atoms of a crown ether molecule and the two N atoms of a pyrazolate anion. The K···O distances range from 2.8416 (8) Å to 3.0025 (8) Å, and the two K···N distances are 2.7441 (11) Å and 2.7654 (11) Å. The K cation is displaced by 0.8437 (4) Å from the best plane through the six O atoms. The latter plane is almost perpendicular to the plane of the pyrazolate ring [dihedral angle 83.93 (3) °].

Experimental

Mn(C₅H₃)(Bpz₃)₂(THF)₂ (64 mg, 75.4 µmol) was dissolved in THF (25 ml). The solution was irradiated using an UV lamp (TQ 150, λmax = 510 nm) for 16 h, whereupon the colourless solution turned orange. After stirring overnight at ambient temperature the reaction mixture was treated with 18-crown-6 (20 mg, 81.2 µmol) and was stirred for 10 minutes. After a small amount of colourless precipitate had been removed by filtration, the clear filtrate was evaporated to dryness in vacuo. Single crystals of (II) were grown from a solution of (II) in THF at -35°C.

Refinement

H atoms were geometrically positioned and refined using a riding model with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] and with Caromatic—H = 0.95Å and Cmethylene—H = 0.99 Å.

Figures

Fig. 1.View larger versionFig. 1. Perspective view 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.

Crystal data

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Data collection

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Refinement

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Special details

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

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Atomic displacement parameters (Å²)

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Geometric parameters (Å, °)

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References

Bieller, S., Haghiri, A., Bolte, M., Bats, J. W., Wagner, M. & Lerner, H.-W. (2006). Inorg. Chim. Acta, 359, 1559–1572.

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Morawitz, M., Zhang, F., Bolte, M., Bats, J. W., Lerner, H.-W. & Wagner, M. (2008). Organometallics, 27, 5067–5074.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.

Trofimenko, S. (1993). Chem. Rev.93, 943–980.

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Fig. 1.

Perspective view 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.

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[K(C₃H₃N₂)(C₁₂H₂₄O₆)] | F(000) = 792
Mr = 370.49 | Dx = 1.274 Mg m⁻³
Monoclinic, P2₁/n | Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn | Cell parameters from 23906 reflections
a = 11.5330 (6) Å | θ = 2.5–25.9°
b = 8.2369 (5) Å | µ = 0.31 mm⁻¹
c = 20.7622 (10) Å | T = 173 K
β = 101.612 (4)° | Needle, colourless
V = 1931.96 (18) Å³ | 0.25 × 0.12 × 0.12 mm
Z = 4 |

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STOE IPDS II two-circle-diffractometer | 3602 independent reflections
Radiation source: fine-focus sealed tube | 3234 reflections with I > 2σ(I)
graphite | Rint = 0.034
ω scans | θmax = 25.6°, θmin = 2.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −12→14
Tmin = 0.919, Tmax = 0.966 | k = −9→9
23118 measured reflections | l = −25→25

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Refinement on F² | Secondary atom site location: difference Fourier map
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026 | H-atom parameters constrained
wR(F²) = 0.066 | w = 1/[σ²(Fo²) + (0.036P)² + 0.3751P] where P = (Fo² + 2Fc²)/3
S = 1.03 | (Δ/σ)max = 0.001
3602 reflections | Δρmax = 0.18 e Å⁻³
218 parameters | Δρmin = −0.19 e Å⁻³
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc²λ³/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0099 (8)

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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.

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| x | y | z | Uiso*/Ueq |
K1 | 0.50031 (2) | 0.36001 (3) | 0.173982 (11) | 0.02711 (9) |
O1 | 0.70384 (7) | 0.33603 (10) | 0.10488 (4) | 0.03149 (19) |
C2 | 0.72895 (12) | 0.16959 (15) | 0.09518 (6) | 0.0375 (3) |
H2A | 0.7929 | 0.1606 | 0.0699 | 0.045* |
H2B | 0.6576 | 0.1149 | 0.0700 | 0.045* |
C3 | 0.76649 (11) | 0.09050 (15) | 0.16099 (6) | 0.0341 (3) |
H3A | 0.7879 | −0.0243 | 0.1554 | 0.041* |
H3B | 0.8366 | 0.1469 | 0.1866 | 0.041* |
O4 | 0.67091 (7) | 0.09896 (9) | 0.19483 (4) | 0.02900 (18) |
C5 | 0.69922 (11) | 0.02037 (14) | 0.25736 (6) | 0.0316 (3) |
H5A | 0.7675 | 0.0750 | 0.2856 | 0.038* |
H5B | 0.7209 | −0.0943 | 0.2517 | 0.038* |
C6 | 0.59374 (11) | 0.02826 (13) | 0.28891 (6) | 0.0312 (3) |
H6A | 0.5233 | −0.0153 | 0.2585 | 0.037* |
H6B | 0.6078 | −0.0382 | 0.3295 | 0.037* |
O7 | 0.57370 (7) | 0.19353 (9) | 0.30449 (4) | 0.02792 (18) |
C8 | 0.48115 (11) | 0.20382 (16) | 0.34087 (6) | 0.0369 (3) |
H8A | 0.5059 | 0.1486 | 0.3838 | 0.044* |
H8B | 0.4093 | 0.1489 | 0.3164 | 0.044* |
C9 | 0.45417 (11) | 0.37812 (16) | 0.35159 (6) | 0.0358 (3) |
H9A | 0.3904 | 0.3860 | 0.3770 | 0.043* |
H9B | 0.5254 | 0.4330 | 0.3768 | 0.043* |
O10 | 0.41787 (7) | 0.45411 (10) | 0.28931 (4) | 0.0337 (2) |
C11 | 0.38264 (12) | 0.61956 (15) | 0.29539 (6) | 0.0373 (3) |
H11A | 0.4487 | 0.6822 | 0.3219 | 0.045* |
H11B | 0.3143 | 0.6243 | 0.3176 | 0.045* |
C12 | 0.34937 (11) | 0.68958 (16) | 0.22762 (7) | 0.0390 (3) |
H12A | 0.2892 | 0.6198 | 0.2000 | 0.047* |
H12B | 0.3147 | 0.7989 | 0.2298 | 0.047* |
O13 | 0.45191 (7) | 0.70035 (10) | 0.19903 (4) | 0.03146 (19) |
C14 | 0.42386 (12) | 0.77471 (15) | 0.13533 (6) | 0.0396 (3) |
H14A | 0.3977 | 0.8880 | 0.1394 | 0.047* |
H14B | 0.3586 | 0.7147 | 0.1069 | 0.047* |
C15 | 0.53103 (13) | 0.77270 (14) | 0.10522 (6) | 0.0397 (3) |
H15A | 0.5160 | 0.8371 | 0.0641 | 0.048* |
H15B | 0.5988 | 0.8219 | 0.1359 | 0.048* |
O16 | 0.55811 (8) | 0.60970 (9) | 0.09139 (4) | 0.03225 (19) |
C17 | 0.65728 (12) | 0.59892 (16) | 0.05956 (6) | 0.0390 (3) |
H17A | 0.7291 | 0.6427 | 0.0887 | 0.047* |
H17B | 0.6418 | 0.6632 | 0.0184 | 0.047* |
C18 | 0.67551 (12) | 0.42399 (17) | 0.04447 (6) | 0.0396 (3) |
H18A | 0.6026 | 0.3793 | 0.0167 | 0.047* |
H18B | 0.7408 | 0.4138 | 0.0202 | 0.047* |
N21 | 0.32022 (9) | 0.19783 (12) | 0.09279 (5) | 0.0333 (2) |
N22 | 0.27171 (9) | 0.34696 (12) | 0.10107 (5) | 0.0347 (2) |
C23 | 0.16225 (12) | 0.34869 (17) | 0.06409 (6) | 0.0405 (3) |
H23 | 0.1094 | 0.4381 | 0.0609 | 0.049* |
C24 | 0.13632 (13) | 0.20214 (18) | 0.03103 (6) | 0.0444 (3) |
H24 | 0.0654 | 0.1709 | 0.0019 | 0.053* |
C25 | 0.23868 (13) | 0.11318 (16) | 0.05093 (6) | 0.0387 (3) |
H25 | 0.2499 | 0.0057 | 0.0368 | 0.046* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
K1 | 0.02916 (14) | 0.02496 (13) | 0.02754 (13) | −0.00022 (9) | 0.00652 (9) | 0.00046 (9)
O1 | 0.0406 (5) | 0.0316 (4) | 0.0228 (4) | −0.0045 (4) | 0.0075 (3) | −0.0025 (3)
C2 | 0.0438 (7) | 0.0348 (6) | 0.0376 (6) | −0.0046 (5) | 0.0171 (5) | −0.0118 (5)
C3 | 0.0315 (6) | 0.0282 (6) | 0.0451 (7) | 0.0019 (5) | 0.0140 (5) | −0.0058 (5)
O4 | 0.0277 (4) | 0.0273 (4) | 0.0321 (4) | 0.0044 (3) | 0.0064 (3) | 0.0016 (3)
C5 | 0.0347 (6) | 0.0243 (5) | 0.0333 (6) | 0.0070 (5) | 0.0008 (5) | 0.0029 (4)
C6 | 0.0368 (6) | 0.0217 (5) | 0.0335 (6) | −0.0004 (5) | 0.0030 (5) | 0.0039 (4)
O7 | 0.0281 (4) | 0.0248 (4) | 0.0323 (4) | −0.0005 (3) | 0.0096 (3) | 0.0020 (3)
C8 | 0.0344 (6) | 0.0399 (7) | 0.0404 (7) | −0.0027 (5) | 0.0172 (5) | 0.0077 (5)
C9 | 0.0364 (7) | 0.0442 (7) | 0.0308 (6) | 0.0010 (5) | 0.0161 (5) | 0.0006 (5)
O10 | 0.0379 (5) | 0.0327 (4) | 0.0324 (4) | 0.0066 (3) | 0.0114 (3) | −0.0026 (3)
C11 | 0.0365 (7) | 0.0350 (6) | 0.0440 (7) | 0.0067 (5) | 0.0166 (5) | −0.0078 (5)
C12 | 0.0308 (6) | 0.0353 (6) | 0.0506 (7) | 0.0106 (5) | 0.0076 (5) | −0.0033 (6)
O13 | 0.0326 (4) | 0.0292 (4) | 0.0309 (4) | 0.0047 (3) | 0.0022 (3) | 0.0008 (3)
C14 | 0.0527 (8) | 0.0266 (6) | 0.0340 (6) | 0.0080 (5) | −0.0041 (6) | 0.0017 (5)
C15 | 0.0595 (8) | 0.0254 (6) | 0.0309 (6) | −0.0083 (6) | 0.0010 (6) | 0.0042 (5)
O16 | 0.0400 (5) | 0.0275 (4) | 0.0293 (4) | −0.0071 (3) | 0.0070 (3) | 0.0027 (3)
C17 | 0.0415 (7) | 0.0466 (7) | 0.0294 (6) | −0.0077 (6) | 0.0086 (5) | 0.0126 (5)
C18 | 0.0452 (7) | 0.0526 (8) | 0.0224 (5) | −0.0014 (6) | 0.0104 (5) | 0.0028 (5)
N21 | 0.0387 (6) | 0.0322 (5) | 0.0298 (5) | −0.0024 (4) | 0.0092 (4) | 0.0017 (4)
N22 | 0.0397 (6) | 0.0325 (5) | 0.0331 (5) | −0.0026 (4) | 0.0099 (4) | 0.0003 (4)
C23 | 0.0384 (7) | 0.0470 (7) | 0.0373 (7) | 0.0047 (6) | 0.0107 (5) | 0.0084 (6)
C24 | 0.0434 (7) | 0.0596 (9) | 0.0271 (6) | −0.0151 (6) | −0.0002 (5) | 0.0047 (6)
C25 | 0.0556 (8) | 0.0352 (6) | 0.0265 (6) | −0.0092 (6) | 0.0107 (5) | −0.0017 (5)

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K1—N21 | 2.7441 (11) | C9—H9B | 0.9900
K1—N22 | 2.7654 (11) | O10—C11 | 1.4349 (14)
K1—O16 | 2.8416 (8) | C11—C12 | 1.4976 (19)
K1—O10 | 2.8557 (8) | C11—H11A | 0.9900
K1—O4 | 2.8877 (8) | C11—H11B | 0.9900
K1—O13 | 2.9254 (8) | C12—O13 | 1.4286 (15)
K1—O1 | 2.9938 (9) | C12—H12A | 0.9900
K1—O7 | 3.0025 (8) | C12—H12B | 0.9900
K1—C12 | 3.5242 (12) | O13—C14 | 1.4341 (14)
O1—C2 | 1.4239 (15) | C14—C15 | 1.493 (2)
O1—C18 | 1.4282 (14) | C14—H14A | 0.9900
C2—C3 | 1.4969 (18) | C14—H14B | 0.9900
C2—H2A | 0.9900 | C15—O16 | 1.4207 (15)
C2—H2B | 0.9900 | C15—H15A | 0.9900
C3—O4 | 1.4231 (14) | C15—H15B | 0.9900
C3—H3A | 0.9900 | O16—C17 | 1.4343 (15)
C3—H3B | 0.9900 | C17—C18 | 1.498 (2)
O4—C5 | 1.4284 (13) | C17—H17A | 0.9900
C5—C6 | 1.4946 (17) | C17—H17B | 0.9900
C5—H5A | 0.9900 | C18—H18A | 0.9900
C5—H5B | 0.9900 | C18—H18B | 0.9900
C6—O7 | 1.4287 (13) | N21—C25 | 1.3405 (16)
C6—H6A | 0.9900 | N21—N22 | 1.3748 (15)
C6—H6B | 0.9900 | N22—C23 | 1.3391 (17)
O7—C8 | 1.4290 (14) | C23—C24 | 1.391 (2)
C8—C9 | 1.4951 (18) | C23—H23 | 0.9500
C8—H8A | 0.9900 | C24—C25 | 1.380 (2)
C8—H8B | 0.9900 | C24—H24 | 0.9500
C9—O10 | 1.4216 (14) | C25—H25 | 0.9500
C9—H9A | 0.9900 |  |
N21—K1—N22 | 28.90 (3) | C9—C8—H8B | 109.7
N21—K1—O16 | 102.83 (3) | H8A—C8—H8B | 108.2
N22—K1—O16 | 90.65 (3) | O10—C9—C8 | 108.63 (10)
N21—K1—O10 | 107.98 (3) | O10—C9—H9A | 110.0
N22—K1—O10 | 91.60 (3) | C8—C9—H9A | 110.0
O16—K1—O10 | 117.88 (2) | O10—C9—H9B | 110.0
N21—K1—O4 | 97.94 (3) | C8—C9—H9B | 110.0
N22—K1—O4 | 126.79 (3) | H9A—C9—H9B | 108.3
O16—K1—O4 | 113.20 (2) | C9—O10—C11 | 112.02 (9)
O10—K1—O4 | 114.09 (2) | C9—O10—K1 | 123.81 (6)
N21—K1—O13 | 115.33 (3) | C11—O10—K1 | 118.66 (7)
N22—K1—O13 | 86.54 (3) | O10—C11—C12 | 107.85 (10)
O16—K1—O13 | 59.34 (2) | O10—C11—H11A | 110.1
O10—K1—O13 | 58.88 (2) | C12—C11—H11A | 110.1
O4—K1—O13 | 146.67 (2) | O10—C11—H11B | 110.1
N21—K1—O1 | 104.07 (3) | C12—C11—H11B | 110.1
N22—K1—O1 | 119.22 (3) | H11A—C11—H11B | 108.4
O16—K1—O1 | 57.10 (2) | O13—C12—C11 | 109.71 (10)
O10—K1—O1 | 147.69 (2) | O13—C12—K1 | 54.11 (5)
O4—K1—O1 | 56.39 (2) | C11—C12—K1 | 87.18 (7)
O13—K1—O1 | 110.15 (2) | O13—C12—H12A | 109.7
N21—K1—O7 | 111.90 (3) | C11—C12—H12A | 109.7
N22—K1—O7 | 122.74 (3) | K1—C12—H12A | 72.7
O16—K1—O7 | 144.82 (2) | O13—C12—H12B | 109.7
O10—K1—O7 | 56.51 (2) | C11—C12—H12B | 109.7
O4—K1—O7 | 57.65 (2) | K1—C12—H12B | 160.8
O13—K1—O7 | 107.84 (2) | H12A—C12—H12B | 108.2
O1—K1—O7 | 107.25 (2) | C12—O13—C14 | 110.96 (9)
N21—K1—C12 | 102.02 (3) | C12—O13—K1 | 102.58 (7)
N22—K1—C12 | 74.09 (3) | C14—O13—K1 | 105.13 (6)
O16—K1—C12 | 79.86 (3) | O13—C14—C15 | 109.23 (10)
O10—K1—C12 | 42.01 (3) | O13—C14—H14A | 109.8
O4—K1—C12 | 153.02 (3) | C15—C14—H14A | 109.8
O13—K1—C12 | 23.31 (3) | O13—C14—H14B | 109.8
O1—K1—C12 | 133.39 (3) | C15—C14—H14B | 109.8
O7—K1—C12 | 97.71 (3) | H14A—C14—H14B | 108.3
C2—O1—C18 | 112.41 (9) | O16—C15—C14 | 109.22 (10)
C2—O1—K1 | 109.43 (6) | O16—C15—H15A | 109.8
C18—O1—K1 | 108.93 (7) | C14—C15—H15A | 109.8
O1—C2—C3 | 108.64 (9) | O16—C15—H15B | 109.8
O1—C2—H2A | 110.0 | C14—C15—H15B | 109.8
C3—C2—H2A | 110.0 | H15A—C15—H15B | 108.3
O1—C2—H2B | 110.0 | C15—O16—C17 | 112.31 (9)
C3—C2—H2B | 110.0 | C15—O16—K1 | 118.32 (7)
H2A—C2—H2B | 108.3 | C17—O16—K1 | 122.61 (7)
O4—C3—C2 | 108.59 (10) | O16—C17—C18 | 108.32 (10)
O4—C3—H3A | 110.0 | O16—C17—H17A | 110.0
C2—C3—H3A | 110.0 | C18—C17—H17A | 110.0
O4—C3—H3B | 110.0 | O16—C17—H17B | 110.0
C2—C3—H3B | 110.0 | C18—C17—H17B | 110.0
H3A—C3—H3B | 108.4 | H17A—C17—H17B | 108.4
C3—O4—C5 | 111.62 (9) | O1—C18—C17 | 108.73 (10)
C3—O4—K1 | 122.31 (6) | O1—C18—H18A | 109.9
C5—O4—K1 | 119.86 (6) | C17—C18—H18A | 109.9
O4—C5—C6 | 108.74 (9) | O1—C18—H18B | 109.9
O4—C5—H5A | 109.9 | C17—C18—H18B | 109.9
C6—C5—H5A | 109.9 | H18A—C18—H18B | 108.3
O4—C5—H5B | 109.9 | C25—N21—N22 | 107.20 (10)
C6—C5—H5B | 109.9 | C25—N21—K1 | 175.53 (9)
H5A—C5—H5B | 108.3 | N22—N21—K1 | 76.41 (6)
O7—C6—C5 | 108.89 (9) | C23—N22—N21 | 107.35 (10)
O7—C6—H6A | 109.9 | C23—N22—K1 | 176.68 (9)
C5—C6—H6A | 109.9 | N21—N22—K1 | 74.69 (6)
O7—C6—H6B | 109.9 | N22—C23—C24 | 110.97 (12)
C5—C6—H6B | 109.9 | N22—C23—H23 | 124.5
H6A—C6—H6B | 108.3 | C24—C23—H23 | 124.5
C6—O7—C8 | 110.38 (9) | C25—C24—C23 | 103.12 (11)
C6—O7—K1 | 105.07 (6) | C25—C24—H24 | 128.4
C8—O7—K1 | 110.19 (7) | C23—C24—H24 | 128.4
O7—C8—C9 | 109.61 (9) | N21—C25—C24 | 111.35 (12)
O7—C8—H8A | 109.7 | N21—C25—H25 | 124.3
C9—C8—H8A | 109.7 | C24—C25—H25 | 124.3
O7—C8—H8B | 109.7 |  |
N21—K1—O1—C2 | −57.90 (8) | O10—C11—C12—O13 | −66.75 (13)
N22—K1—O1—C2 | −84.52 (8) | O10—C11—C12—K1 | −16.62 (9)
O16—K1—O1—C2 | −154.25 (8) | N21—K1—C12—O13 | −127.69 (7)
O10—K1—O1—C2 | 114.66 (8) | N22—K1—C12—O13 | −120.20 (7)
O4—K1—O1—C2 | 32.36 (7) | O16—K1—C12—O13 | −26.59 (6)
O13—K1—O1—C2 | 177.93 (7) | O10—K1—C12—O13 | 128.70 (8)
O7—K1—O1—C2 | 60.82 (7) | O4—K1—C12—O13 | 95.46 (8)
C12—K1—O1—C2 | 179.95 (7) | O1—K1—C12—O13 | −4.80 (8)
N21—K1—O1—C18 | 65.36 (7) | O7—K1—C12—O13 | 117.87 (7)
N22—K1—O1—C18 | 38.75 (8) | N21—K1—C12—C11 | 115.40 (8)
O16—K1—O1—C18 | −30.99 (7) | N22—K1—C12—C11 | 122.89 (8)
O10—K1—O1—C18 | −122.08 (8) | O16—K1—C12—C11 | −143.49 (8)
O4—K1—O1—C18 | 155.62 (8) | O10—K1—C12—C11 | 11.80 (7)
O13—K1—O1—C18 | −58.81 (7) | O4—K1—C12—C11 | −21.45 (11)
O7—K1—O1—C18 | −175.92 (7) | O13—K1—C12—C11 | −116.90 (11)
C12—K1—O1—C18 | −56.79 (8) | O1—K1—C12—C11 | −121.70 (7)
C18—O1—C2—C3 | 175.73 (10) | O7—K1—C12—C11 | 0.96 (8)
K1—O1—C2—C3 | −63.09 (10) | C11—C12—O13—C14 | −177.06 (10)
O1—C2—C3—O4 | 62.21 (12) | K1—C12—O13—C14 | 111.83 (9)
C2—C3—O4—C5 | 177.94 (9) | C11—C12—O13—K1 | 71.11 (10)
C2—C3—O4—K1 | −29.89 (12) | N21—K1—O13—C12 | 58.90 (7)
N21—K1—O4—C3 | 101.35 (8) | N22—K1—O13—C12 | 56.37 (7)
N22—K1—O4—C3 | 103.29 (8) | O16—K1—O13—C12 | 149.19 (7)
O16—K1—O4—C3 | −6.34 (8) | O10—K1—O13—C12 | −37.60 (7)
O10—K1—O4—C3 | −144.84 (8) | O4—K1—O13—C12 | −124.72 (7)
O13—K1—O4—C3 | −75.35 (9) | O1—K1—O13—C12 | 176.29 (7)
O1—K1—O4—C3 | −0.30 (7) | O7—K1—O13—C12 | −66.97 (7)
O7—K1—O4—C3 | −147.70 (8) | N21—K1—O13—C14 | −57.21 (8)
C12—K1—O4—C3 | −121.14 (9) | N22—K1—O13—C14 | −59.73 (7)
N21—K1—O4—C5 | −108.68 (8) | O16—K1—O13—C14 | 33.09 (7)
N22—K1—O4—C5 | −106.74 (8) | O10—K1—O13—C14 | −153.70 (8)
O16—K1—O4—C5 | 143.63 (7) | O4—K1—O13—C14 | 119.17 (8)
O10—K1—O4—C5 | 5.13 (8) | O1—K1—O13—C14 | 60.18 (8)
O13—K1—O4—C5 | 74.62 (9) | O7—K1—O13—C14 | 176.92 (7)
O1—K1—O4—C5 | 149.67 (8) | C12—K1—O13—C14 | −116.10 (10)
O7—K1—O4—C5 | 2.26 (7) | C12—O13—C14—C15 | −175.93 (9)
C12—K1—O4—C5 | 28.83 (11) | K1—O13—C14—C15 | −65.73 (10)
C3—O4—C5—C6 | −177.84 (9) | O13—C14—C15—O16 | 67.33 (12)
K1—O4—C5—C6 | 29.22 (11) | C14—C15—O16—C17 | 177.37 (9)
O4—C5—C6—O7 | −67.15 (11) | C14—C15—O16—K1 | −30.65 (12)
C5—C6—O7—C8 | −173.98 (9) | N21—K1—O16—C15 | 111.08 (8)
C5—C6—O7—K1 | 67.25 (9) | N22—K1—O16—C15 | 84.64 (8)
N21—K1—O7—C6 | 51.07 (7) | O10—K1—O16—C15 | −7.51 (9)
N22—K1—O7—C6 | 81.39 (7) | O4—K1—O16—C15 | −144.33 (8)
O16—K1—O7—C6 | −119.30 (7) | O13—K1—O16—C15 | −0.94 (8)
O10—K1—O7—C6 | 148.71 (7) | O1—K1—O16—C15 | −150.32 (9)
O4—K1—O7—C6 | −34.43 (6) | O7—K1—O16—C15 | −78.07 (9)
O13—K1—O7—C6 | 178.94 (6) | C12—K1—O16—C15 | 10.94 (8)
O1—K1—O7—C6 | −62.45 (7) | N21—K1—O16—C17 | −99.97 (8)
C12—K1—O7—C6 | 157.38 (6) | N22—K1—O16—C17 | −126.41 (8)
N21—K1—O7—C8 | −67.83 (7) | O10—K1—O16—C17 | 141.43 (8)
N22—K1—O7—C8 | −37.51 (8) | O4—K1—O16—C17 | 4.61 (9)
O16—K1—O7—C8 | 121.80 (7) | O13—K1—O16—C17 | 148.00 (9)
O10—K1—O7—C8 | 29.81 (7) | O1—K1—O16—C17 | −1.38 (8)
O4—K1—O7—C8 | −153.33 (8) | O7—K1—O16—C17 | 70.88 (9)
O13—K1—O7—C8 | 60.04 (7) | C12—K1—O16—C17 | 159.88 (8)
O1—K1—O7—C8 | 178.65 (7) | C15—O16—C17—C18 | −177.58 (10)
C12—K1—O7—C8 | 38.48 (7) | K1—O16—C17—C18 | 31.82 (12)
C6—O7—C8—C9 | −175.05 (10) | C2—O1—C18—C17 | −176.81 (10)
K1—O7—C8—C9 | −59.45 (11) | K1—O1—C18—C17 | 61.72 (11)
O7—C8—C9—O10 | 59.92 (13) | O16—C17—C18—O1 | −62.76 (13)
C8—C9—O10—C11 | 176.08 (10) | O16—K1—N21—N22 | −67.14 (6)
C8—C9—O10—K1 | −30.63 (13) | O10—K1—N21—N22 | 58.19 (6)
N21—K1—O10—C9 | 106.21 (9) | O4—K1—N21—N22 | 176.78 (6)
N22—K1—O10—C9 | 130.46 (9) | O13—K1—N21—N22 | −5.23 (7)
O16—K1—O10—C9 | −137.95 (8) | O1—K1—N21—N22 | −125.99 (6)
O4—K1—O10—C9 | −1.51 (9) | O7—K1—N21—N22 | 118.53 (6)
O13—K1—O10—C9 | −144.56 (9) | C12—K1—N21—N22 | 15.04 (6)
O1—K1—O10—C9 | −66.20 (10) | C25—N21—N22—C23 | 0.02 (12)
O7—K1—O10—C9 | 1.40 (8) | K1—N21—N22—C23 | 177.28 (9)
C12—K1—O10—C9 | −165.70 (10) | C25—N21—N22—K1 | −177.26 (9)
N21—K1—O10—C11 | −102.15 (8) | O16—K1—N22—N21 | 116.04 (6)
N22—K1—O10—C11 | −77.90 (8) | O10—K1—N22—N21 | −126.04 (6)
O16—K1—O10—C11 | 13.69 (9) | O4—K1—N22—N21 | −3.98 (7)
O4—K1—O10—C11 | 150.13 (8) | O13—K1—N22—N21 | 175.27 (6)
O13—K1—O10—C11 | 7.09 (8) | O1—K1—N22—N21 | 64.07 (6)
O1—K1—O10—C11 | 85.44 (9) | O7—K1—N22—N21 | −75.70 (6)
O7—K1—O10—C11 | 153.04 (9) | C12—K1—N22—N21 | −164.70 (6)
C12—K1—O10—C11 | −14.06 (8) | N21—N22—C23—C24 | 0.11 (14)
C9—O10—C11—C12 | 178.50 (10) | N22—C23—C24—C25 | −0.18 (14)
K1—O10—C11—C12 | 23.70 (12) | C23—C24—C25—N21 | 0.19 (14)

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