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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m799–m800.
Published online 2010 June 16. doi:  10.1107/S1600536810021458
PMCID: PMC3006768

Potassium bis­(1,1,1,5,5,5-hexa­fluoro­pentane-2,4-dionato)bis­(4,4,4-trifluoro-1-phenyl­butane-1,3-dionato)europate(III)

Abstract

In the crystal structure of the title complex, K[Eu(C5HF6O2)2(C10H6F3O2)2], the EuIII ion is in a slightly distorted square-anti­prismatic coordination geometry which is defined by eight O atoms of the anionic β-diketone ligands. The two K+ ions lie on crystallographic inversion centers. The Eu—O bond distances are in the range 2.294 (5)–2.413 (5) Å. The crystal used was a non-merohedral twin, the ratio of the twin domains being 0.5236 (5):0.4764 (5).

Related literature

For general background to and potential applications of luminescent lanthanide complexes containing β-diketonates, see: Eliseeva & Bunzli (2010 [triangle]); de Bettencourt-Dias (1997 [triangle]); Stanley et al. (2010 [triangle]); Chen & Holliday (2008 [triangle]). For similar structures, see: Nockemann et al. (2005 [triangle]); Burns & Danford (1969 [triangle]). The twin law was determined using TwinSolve (Rigaku/MSC, 2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m799-scheme1.jpg

Experimental

Crystal data

  • K[Eu(C5HF6O2)2(C10H6F3O2)2]
  • M r = 1035.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m799-efi1.jpg
  • a = 11.737 (2) Å
  • b = 12.468 (2) Å
  • c = 13.788 (3) Å
  • α = 68.457 (8)°
  • β = 71.791 (8)°
  • γ = 71.726 (8)°
  • V = 1737.1 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.07 mm−1
  • T = 100 K
  • 0.12 × 0.06 × 0.03 mm

Data collection

  • Rigaku AFC12 with Saturn 724+ CCD diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 2001 [triangle]) T min = 0.789, T max = 0.941
  • 25336 measured reflections
  • 25336 independent reflections
  • 22905 reflections with I > 2σ(I)

Refinement

  • R[F 2 > 2σ(F 2)] = 0.096
  • wR(F 2) = 0.197
  • S = 3.00
  • 25336 reflections
  • 527 parameters
  • H-atom parameters constrained
  • Δρmax = 3.65 e Å−3
  • Δρmin = −3.79 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]) within WinGX (Farrugia, 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and POV-RAY (Persistence of Vision, 2004 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021458/lh5047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021458/lh5047Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We gratefully acknowledge the Robert A. Welch Foundation (F-1631), the Petroleum Research Fund administered by the American Chemical Society (47022-G3), the National Science Foundation (CHE-0639239, CHE-0741973 and CHE-0847763), the American Heart Association (0765078Y), the UT-CNM and UT-Austin for financial support of this research. Single crystal X-ray data were collected using instrumentation purchased with funds provided by the National Science Foundation grant No. 0741973.

supplementary crystallographic information

Comment

Luminescent lanthanide complexes containing β-diketonates have many potential applications (Eliseeva & Bunzli, 2010; de Bettencourt-Dias, 1997; Stanley et al., 2010; Chen & Holliday, 2008). The solid-state crystal structure of K[Eu(hfac)2(btfac)2], where hfac = 1,1,1,5,5,5-hexafluoro-2,4-pentandionate and btfac = 4,4,4-trifluoro-1-phenyl-1,3-butanedionate, can be seen in Figure 1A. While complexes of the type A[Ln(L)4], where A = Na6+ or K+ and L = acetoacetonate derivatives, have been reported (Nockemann et al. (2005); Burns & Danford (1969)), this is the first example of a mixed ligand complex that has been structurally characterized. After removing all atoms not bound to the metal center, it is apparent that the local coordination environment around the trivalent europium ion is a slightly distorted square antiprism (Figure 1B).

Experimental

The title compound, K[Eu(hfac)2(btfac)2], was obtained as an unexpected product during the attempted synthesis of a europium tris(β-diketonate) bis(pyrazolyl)pyridine complex in which potassium tert-butoxide was used to deprotonate the β-diketone prior to complexation with the lanthanide salt.

Refinement

The data crystal was twinned, which can result in more than one entry in the reflection file for a given set of h,k,l indices. Twinning can lead to more reflections being used in the refinement than the actual number of unique reflections. The twin law was determined using TwinSolve (Rigaku/MSC, 2002). The twin resulted from a 180 degree rotation about the 0-10 direct lattice direction with twin matrix [-1.000, -0.470, 0.000; -0.001, 1.000, 0.000; 0.000, -0.540, -0.999]. The twin fraction refined to 0.4764 (5).

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Figures

Fig. 1.
(A) ORTEP diagram of K[Eu(hfac)2(btfac)2] showing the labeling scheme of selected atoms at 30% probability level. Hydrogen atoms are omitted for clarity. (B) Coordination environment around EuIII in K[Eu(hfac)2(btfac)2].

Crystal data

K[Eu(C5HF6O2)2(C10H6F3O2)2]Z = 2
Mr = 1035.47F(000) = 1004
Triclinic, P1Dx = 1.980 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 11.737 (2) ÅCell parameters from 30786 reflections
b = 12.468 (2) Åθ = 4.7–27.5°
c = 13.788 (3) ŵ = 2.07 mm1
α = 68.457 (8)°T = 100 K
β = 71.791 (8)°Block, colourless
γ = 71.726 (8)°0.12 × 0.06 × 0.03 mm
V = 1737.1 (5) Å3

Data collection

Rigaku AFC12 with Saturn 724+ CCD diffractometer25336 independent reflections
Radiation source: fine-focus sealed tube22905 reflections with I > 2σ(I)
graphiteRint = 0.0000
ω–scansθmax = 25.0°, θmin = 4.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 2001)h = −13→13
Tmin = 0.789, Tmax = 0.941k = −14→14
25336 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.096Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 3.00w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
25336 reflections(Δ/σ)max = 0.008
527 parametersΔρmax = 3.65 e Å3
0 restraintsΔρmin = −3.79 e Å3

Special details

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 > 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)

xyzUiso*/Ueq
C10.1917 (8)0.5647 (8)−0.0670 (7)0.046 (2)
C20.1678 (6)0.5603 (6)0.0491 (5)0.0270 (16)
C30.0581 (7)0.6211 (6)0.0938 (6)0.0309 (17)
H30.00180.66970.04970.037*
C40.0261 (6)0.6153 (6)0.1978 (6)0.0258 (16)
C5−0.0953 (7)0.6967 (7)0.2354 (6)0.0380 (19)
C60.6359 (8)0.1771 (7)0.1235 (6)0.041 (2)
C70.5469 (7)0.2239 (6)0.2119 (6)0.0338 (17)
C80.5666 (7)0.1706 (7)0.3098 (7)0.039 (2)
H80.63840.10920.31910.047*
C90.4860 (6)0.2006 (6)0.4008 (6)0.0296 (17)
C100.5163 (8)0.1435 (6)0.5104 (6)0.0381 (19)
C110.4273 (8)0.1526 (9)0.5946 (6)0.066 (3)
H250.34520.18630.58580.079*
C120.4490 (10)0.1155 (9)0.6927 (8)0.065 (3)
H260.38560.13150.75170.078*
C130.5696 (10)0.0513 (9)0.7066 (8)0.058 (3)
H270.58860.01980.77520.070*
C140.6554 (8)0.0375 (9)0.6180 (8)0.057 (3)
H280.7372−0.00310.62490.069*
C150.6304 (9)0.0789 (9)0.5191 (7)0.063 (3)
H290.69090.06280.45870.076*
C160.0084 (8)0.1836 (7)0.5500 (6)0.041 (2)
C170.0708 (7)0.2337 (6)0.4328 (6)0.0319 (18)
C180.0681 (9)0.1848 (8)0.3593 (7)0.050 (3)
H150.01740.13010.38090.059*
C190.1342 (8)0.2112 (6)0.2585 (7)0.040 (2)
C200.1338 (7)0.1522 (6)0.1815 (6)0.0357 (18)
C210.2254 (11)0.1550 (9)0.0945 (7)0.079 (4)
H160.28510.19880.08020.095*
C220.2341 (10)0.0944 (8)0.0250 (8)0.066 (3)
H170.30150.0934−0.03490.079*
C230.1444 (12)0.0361 (9)0.0438 (9)0.076 (4)
H180.1508−0.0062−0.00340.091*
C240.0410 (10)0.0374 (8)0.1331 (8)0.068 (3)
H19−0.02420.00110.14500.081*
C250.0430 (9)0.0959 (8)0.2015 (7)0.049 (2)
H20−0.02110.09630.26390.059*
C260.2817 (8)0.5623 (8)0.5313 (7)0.045 (2)
C270.3058 (7)0.5583 (6)0.4158 (6)0.0352 (18)
C280.3889 (6)0.6178 (6)0.3388 (6)0.0266 (16)
H220.42580.66310.35740.032*
C290.4211 (6)0.6142 (6)0.2347 (6)0.0283 (16)
C300.5014 (7)0.6967 (7)0.1520 (6)0.0388 (19)
Eu10.27159 (3)0.40232 (3)0.27527 (3)0.02047 (10)
F10.3069 (4)0.5677 (4)−0.1188 (3)0.0435 (11)
F20.1728 (5)0.4659 (5)−0.0700 (4)0.0657 (17)
F30.1194 (5)0.6532 (6)−0.1202 (4)0.088 (2)
F4−0.1848 (4)0.6928 (5)0.2024 (4)0.0598 (14)
F5−0.0824 (5)0.8077 (4)0.2013 (4)0.0570 (15)
F6−0.1285 (4)0.6694 (4)0.3418 (3)0.0407 (11)
F70.6624 (4)0.2662 (3)0.0350 (3)0.0412 (11)
F80.7376 (5)0.1090 (5)0.1463 (4)0.0737 (17)
F90.5835 (5)0.1168 (4)0.0933 (4)0.0519 (13)
F100.0912 (5)0.1121 (3)0.6036 (4)0.0563 (14)
F11−0.0526 (4)0.2664 (3)0.5961 (3)0.0385 (10)
F12−0.0690 (5)0.1203 (4)0.5625 (4)0.0638 (15)
F130.5488 (4)0.6708 (4)0.0626 (3)0.0395 (10)
F140.4382 (5)0.8067 (4)0.1321 (4)0.0584 (16)
F150.5956 (5)0.6911 (5)0.1884 (4)0.0709 (16)
F160.1628 (4)0.5698 (4)0.5792 (3)0.0427 (11)
F170.3433 (5)0.4672 (5)0.5884 (4)0.0657 (17)
F180.3105 (6)0.6547 (5)0.5334 (4)0.0800 (19)
O10.2551 (4)0.4986 (5)0.0915 (4)0.0251 (12)
O20.0837 (4)0.5516 (4)0.2704 (4)0.0269 (11)
O30.4609 (4)0.3098 (4)0.1823 (4)0.0312 (11)
O40.3868 (4)0.2735 (4)0.3960 (4)0.0358 (12)
O50.1244 (4)0.3130 (4)0.4191 (3)0.0291 (11)
O60.2076 (5)0.2811 (4)0.2196 (4)0.0368 (12)
O70.3927 (4)0.5503 (4)0.1993 (4)0.0273 (11)
O80.2463 (4)0.4963 (5)0.4063 (4)0.0302 (13)
K10.00000.50000.50000.0293 (6)
K20.50000.50000.00000.0270 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.042 (5)0.060 (6)0.039 (5)0.001 (4)−0.019 (4)−0.020 (4)
C20.023 (4)0.037 (4)0.021 (4)−0.013 (3)−0.003 (3)−0.007 (3)
C30.031 (4)0.033 (4)0.022 (4)−0.006 (3)−0.003 (3)−0.003 (3)
C40.018 (4)0.018 (3)0.035 (4)0.003 (3)−0.005 (3)−0.008 (3)
C50.037 (5)0.050 (5)0.027 (4)−0.004 (4)−0.013 (4)−0.012 (4)
C60.044 (5)0.040 (5)0.029 (4)0.002 (4)0.001 (4)−0.014 (4)
C70.029 (4)0.028 (4)0.041 (5)−0.002 (3)−0.002 (4)−0.015 (3)
C80.026 (4)0.030 (4)0.049 (5)0.005 (3)0.000 (4)−0.013 (4)
C90.026 (4)0.033 (4)0.025 (4)−0.009 (3)0.002 (3)−0.007 (3)
C100.051 (5)0.023 (4)0.034 (4)−0.004 (3)−0.010 (4)−0.003 (3)
C110.037 (5)0.099 (8)0.025 (5)0.013 (5)−0.010 (4)0.001 (5)
C120.064 (7)0.074 (7)0.051 (6)0.007 (5)−0.020 (5)−0.026 (5)
C130.060 (7)0.075 (7)0.053 (6)−0.007 (5)−0.030 (6)−0.026 (5)
C140.030 (5)0.076 (7)0.058 (6)−0.015 (4)−0.018 (5)−0.001 (5)
C150.046 (6)0.071 (7)0.024 (5)0.032 (5)−0.008 (4)0.001 (4)
C160.057 (5)0.027 (4)0.032 (4)−0.020 (4)0.003 (4)−0.001 (3)
C170.034 (4)0.017 (4)0.033 (4)−0.009 (3)0.011 (3)−0.007 (3)
C180.064 (6)0.047 (6)0.049 (6)−0.033 (5)0.014 (5)−0.031 (4)
C190.058 (5)0.032 (4)0.039 (5)−0.023 (4)−0.015 (4)−0.009 (4)
C200.048 (5)0.034 (4)0.029 (4)−0.025 (4)0.001 (4)−0.007 (3)
C210.141 (10)0.098 (8)0.032 (5)−0.096 (8)0.022 (6)−0.034 (5)
C220.080 (7)0.041 (5)0.072 (7)−0.021 (5)0.010 (6)−0.028 (5)
C230.104 (9)0.052 (6)0.068 (7)−0.019 (6)0.005 (7)−0.032 (6)
C240.088 (8)0.052 (6)0.059 (7)−0.035 (5)0.002 (6)−0.010 (5)
C250.070 (6)0.060 (6)0.033 (5)−0.044 (5)0.001 (4)−0.018 (4)
C260.050 (6)0.058 (6)0.040 (5)−0.017 (5)−0.011 (5)−0.023 (4)
C270.030 (4)0.030 (4)0.055 (5)0.004 (3)−0.018 (4)−0.025 (4)
C280.017 (4)0.028 (4)0.045 (5)−0.011 (3)−0.014 (3)−0.012 (3)
C290.026 (4)0.031 (4)0.031 (4)−0.003 (3)−0.014 (3)−0.009 (3)
C300.041 (5)0.047 (5)0.040 (5)−0.029 (4)−0.008 (4)−0.009 (4)
Eu10.01748 (16)0.02274 (16)0.02001 (16)−0.00665 (12)0.00050 (11)−0.00718 (13)
F10.047 (3)0.057 (3)0.027 (2)−0.017 (2)−0.004 (2)−0.013 (2)
F20.067 (4)0.100 (6)0.058 (4)−0.045 (3)0.001 (3)−0.046 (3)
F30.066 (4)0.129 (5)0.034 (3)0.036 (4)−0.023 (3)−0.024 (3)
F40.028 (3)0.092 (4)0.074 (4)0.013 (2)−0.025 (3)−0.052 (3)
F50.077 (4)0.025 (3)0.053 (3)−0.002 (2)−0.005 (3)−0.008 (2)
F60.027 (2)0.041 (2)0.044 (3)0.0052 (18)−0.001 (2)−0.018 (2)
F70.037 (3)0.036 (2)0.039 (3)−0.0106 (19)0.012 (2)−0.014 (2)
F80.054 (3)0.080 (4)0.051 (3)0.039 (3)−0.011 (3)−0.025 (3)
F90.069 (3)0.037 (2)0.045 (3)−0.013 (2)0.011 (3)−0.027 (2)
F100.068 (3)0.036 (2)0.038 (3)0.000 (3)0.001 (3)−0.001 (2)
F110.042 (3)0.042 (2)0.030 (2)−0.017 (2)0.006 (2)−0.016 (2)
F120.096 (4)0.060 (3)0.043 (3)−0.060 (3)0.019 (3)−0.018 (2)
F130.037 (2)0.047 (3)0.033 (2)−0.022 (2)0.007 (2)−0.011 (2)
F140.092 (4)0.031 (3)0.043 (3)−0.021 (3)0.003 (3)−0.011 (2)
F150.067 (4)0.109 (4)0.053 (3)−0.066 (3)−0.008 (3)−0.008 (3)
F160.038 (3)0.057 (3)0.031 (2)−0.011 (2)0.006 (2)−0.023 (2)
F170.051 (3)0.104 (6)0.037 (3)0.000 (3)−0.024 (3)−0.017 (3)
F180.120 (5)0.106 (5)0.051 (3)−0.075 (4)0.008 (3)−0.046 (3)
O10.024 (3)0.029 (2)0.031 (3)−0.015 (2)−0.001 (3)−0.015 (2)
O20.029 (3)0.029 (3)0.023 (3)−0.013 (2)0.003 (2)−0.009 (2)
O30.023 (3)0.028 (3)0.035 (3)−0.003 (2)0.004 (2)−0.011 (2)
O40.028 (3)0.038 (3)0.030 (3)0.007 (2)−0.004 (2)−0.012 (2)
O50.038 (3)0.033 (3)0.018 (2)−0.014 (2)0.001 (2)−0.011 (2)
O60.041 (3)0.044 (3)0.034 (3)−0.020 (2)0.002 (2)−0.020 (2)
O70.022 (3)0.034 (3)0.032 (3)−0.012 (2)−0.003 (2)−0.015 (2)
O80.028 (3)0.027 (2)0.041 (4)−0.010 (2)−0.004 (3)−0.016 (2)
K10.0263 (13)0.0289 (11)0.0318 (18)−0.0071 (10)−0.0013 (13)−0.0118 (9)
K20.0237 (12)0.0352 (11)0.0197 (16)−0.0096 (10)0.0031 (12)−0.0095 (9)

Geometric parameters (Å, °)

C1—F31.297 (9)C17—O51.260 (8)
C1—F11.322 (9)C17—C181.373 (11)
C1—F21.335 (10)C18—C191.340 (11)
C1—C21.519 (10)C18—H150.9500
C2—O11.239 (8)C19—O61.276 (9)
C2—C31.359 (10)C19—C201.499 (10)
C3—C41.345 (10)C20—C211.335 (11)
C3—H30.9500C20—C251.360 (11)
C4—O21.261 (8)C21—C221.386 (12)
C4—C51.531 (10)C21—H160.9500
C5—F41.288 (8)C22—C231.369 (15)
C5—F51.330 (9)C22—H170.9500
C5—F61.334 (8)C23—C241.435 (14)
C6—F81.284 (9)C23—H180.9500
C6—F91.339 (10)C24—C251.396 (12)
C6—F71.343 (8)C24—H190.9500
C6—C71.504 (10)C25—H200.9500
C7—O31.262 (9)C26—F171.296 (10)
C7—C81.325 (11)C26—F181.310 (9)
C8—C91.410 (10)C26—F161.334 (9)
C8—H80.9500C26—C271.545 (11)
C9—O41.236 (8)C27—O81.253 (8)
C9—C101.518 (10)C27—C281.363 (10)
C10—C111.311 (11)C28—C291.380 (10)
C10—C151.345 (12)C28—H220.9500
C11—C121.338 (12)C29—O71.239 (8)
C11—H250.9500C29—C301.524 (10)
C12—C131.423 (14)C30—F131.297 (8)
C12—H260.9500C30—F141.312 (9)
C13—C141.347 (13)C30—F151.323 (9)
C13—H270.9500Eu1—O42.294 (5)
C14—C151.361 (12)Eu1—O62.315 (5)
C14—H280.9500Eu1—O52.367 (4)
C15—H290.9500Eu1—O32.368 (4)
C16—F101.307 (10)Eu1—O82.394 (5)
C16—F111.310 (8)Eu1—O22.400 (5)
C16—F121.315 (9)Eu1—O72.412 (4)
C16—C171.531 (10)Eu1—O12.413 (5)
F3—C1—F1108.5 (7)C16—F11—K1119.4 (4)
F3—C1—F2107.2 (7)C30—F13—K2127.8 (4)
F1—C1—F2106.0 (6)C26—F16—K1121.0 (4)
F3—C1—C2113.2 (7)C2—O1—Eu1133.2 (4)
F1—C1—C2112.7 (7)C2—O1—K2125.6 (4)
F2—C1—C2108.8 (7)Eu1—O1—K298.37 (15)
O1—C2—C3128.0 (7)C4—O2—Eu1133.7 (4)
O1—C2—C1113.1 (6)C4—O2—K1129.6 (4)
C3—C2—C1118.9 (7)Eu1—O2—K195.34 (15)
C4—C3—C2122.7 (7)C7—O3—Eu1133.5 (5)
C4—C3—H3118.7C7—O3—K2122.7 (4)
C2—C3—H3118.7Eu1—O3—K298.83 (15)
O2—C4—C3128.6 (6)C9—O4—Eu1141.3 (5)
O2—C4—C5114.3 (6)C17—O5—Eu1132.8 (4)
C3—C4—C5117.1 (6)C17—O5—K1120.0 (4)
F4—C5—F5109.1 (6)Eu1—O5—K199.91 (15)
F4—C5—F6107.6 (6)C19—O6—Eu1138.0 (5)
F5—C5—F6105.5 (6)C29—O7—Eu1134.9 (5)
F4—C5—C4112.5 (6)C29—O7—K2128.1 (4)
F5—C5—C4110.0 (6)Eu1—O7—K295.88 (14)
F6—C5—C4111.9 (6)C27—O8—Eu1133.6 (5)
F8—C6—F9107.5 (7)C27—O8—K1124.7 (4)
F8—C6—F7108.2 (7)Eu1—O8—K198.81 (14)
F9—C6—F7104.3 (6)O5i—K1—O5180.0
F8—C6—C7115.2 (7)O5i—K1—O8i65.46 (14)
F9—C6—C7110.2 (7)O5—K1—O8i114.54 (14)
F7—C6—C7110.9 (6)O5i—K1—O8114.54 (14)
O3—C7—C8128.2 (7)O5—K1—O865.46 (14)
O3—C7—C6114.5 (7)O8i—K1—O8180.0
C8—C7—C6117.4 (7)O5i—K1—F674.59 (13)
C7—C8—C9123.1 (7)O5—K1—F6105.41 (13)
C7—C8—H8118.4O8i—K1—F675.14 (14)
C9—C8—H8118.4O8—K1—F6104.86 (14)
O4—C9—C8122.1 (7)O5i—K1—F6i105.41 (13)
O4—C9—C10116.4 (6)O5—K1—F6i74.59 (13)
C8—C9—C10121.5 (7)O8i—K1—F6i104.86 (14)
C11—C10—C15121.9 (8)O8—K1—F6i75.14 (14)
C11—C10—C9118.3 (7)F6—K1—F6i180.0
C15—C10—C9119.6 (7)O5i—K1—O2i62.26 (13)
C10—C11—C12121.7 (9)O5—K1—O2i117.74 (13)
C10—C11—H25119.1O8i—K1—O2i60.32 (14)
C12—C11—H25119.1O8—K1—O2i119.68 (14)
C11—C12—C13118.4 (9)F6—K1—O2i127.09 (12)
C11—C12—H26120.8F6i—K1—O2i52.91 (12)
C13—C12—H26120.8O5i—K1—O2117.74 (13)
C14—C13—C12116.9 (9)O5—K1—O262.26 (13)
C14—C13—H27121.5O8i—K1—O2119.68 (14)
C12—C13—H27121.5O8—K1—O260.32 (14)
C13—C14—C15123.0 (9)F6—K1—O252.91 (12)
C13—C14—H28118.5F6i—K1—O2127.09 (12)
C15—C14—H28118.5O2i—K1—O2180.000 (1)
C10—C15—C14117.2 (8)O5i—K1—F11i56.45 (12)
C10—C15—H29121.4O5—K1—F11i123.55 (12)
C14—C15—H29121.4O8i—K1—F11i113.43 (13)
F10—C16—F11108.0 (7)O8—K1—F11i66.57 (13)
F10—C16—F12105.7 (6)F6—K1—F11i61.25 (13)
F11—C16—F12107.2 (6)F6i—K1—F11i118.75 (13)
F10—C16—C17109.8 (7)O2i—K1—F11i110.84 (11)
F11—C16—C17112.5 (6)O2—K1—F11i69.16 (11)
F12—C16—C17113.2 (7)O5i—K1—F11123.55 (12)
O5—C17—C18128.8 (7)O5—K1—F1156.45 (12)
O5—C17—C16112.7 (7)O8i—K1—F1166.57 (13)
C18—C17—C16118.4 (7)O8—K1—F11113.43 (13)
C19—C18—C17122.5 (8)F6—K1—F11118.75 (13)
C19—C18—H15118.7F6i—K1—F1161.25 (13)
C17—C18—H15118.7O2i—K1—F1169.16 (11)
O6—C19—C18125.3 (7)O2—K1—F11110.84 (11)
O6—C19—C20113.3 (7)F11i—K1—F11180.000 (1)
C18—C19—C20121.3 (7)O5i—K1—F16i111.12 (13)
C21—C20—C25121.3 (7)O5—K1—F16i68.88 (13)
C21—C20—C19118.3 (7)O8i—K1—F16i55.40 (12)
C25—C20—C19120.3 (7)O8—K1—F16i124.60 (12)
C20—C21—C22120.5 (8)F6—K1—F16i59.70 (13)
C20—C21—H16119.7F6i—K1—F16i120.30 (13)
C22—C21—H16119.7O2i—K1—F16i108.34 (12)
C23—C22—C21119.3 (9)O2—K1—F16i71.66 (12)
C23—C22—H17120.4F11i—K1—F16i120.65 (12)
C21—C22—H17120.4F11—K1—F16i59.35 (12)
C22—C23—C24121.4 (10)O5i—K1—F1668.88 (13)
C22—C23—H18119.3O5—K1—F16111.12 (13)
C24—C23—H18119.3O8i—K1—F16124.60 (12)
C25—C24—C23115.3 (10)O8—K1—F1655.40 (12)
C25—C24—H19122.4F6—K1—F16120.30 (13)
C23—C24—H19122.4F6i—K1—F1659.70 (13)
C20—C25—C24122.0 (8)O2i—K1—F1671.66 (12)
C20—C25—H20119.0O2—K1—F16108.34 (12)
C24—C25—H20119.0F11i—K1—F1659.35 (12)
F17—C26—F18109.0 (7)F11—K1—F16120.65 (12)
F17—C26—F16107.3 (7)F16i—K1—F16180.00 (14)
F18—C26—F16106.6 (7)O1ii—K2—O1180.0
F17—C26—C27111.0 (7)O1ii—K2—O3ii65.99 (14)
F18—C26—C27111.8 (7)O1—K2—O3ii114.01 (14)
F16—C26—C27110.9 (7)O1ii—K2—O3114.01 (14)
O8—C27—C28128.3 (7)O1—K2—O365.99 (14)
O8—C27—C26113.8 (7)O3ii—K2—O3180.00 (16)
C28—C27—C26117.9 (7)O1ii—K2—F13ii105.49 (12)
C27—C28—C29122.0 (6)O1—K2—F13ii74.51 (12)
C27—C28—H22119.0O3ii—K2—F13ii107.25 (13)
C29—C28—H22119.0O3—K2—F13ii72.75 (13)
O7—C29—C28127.5 (7)O1ii—K2—F1374.51 (12)
O7—C29—C30114.9 (6)O1—K2—F13105.49 (12)
C28—C29—C30117.6 (6)O3ii—K2—F1372.75 (13)
F13—C30—F14109.0 (6)O3—K2—F13107.25 (13)
F13—C30—F15106.0 (6)F13ii—K2—F13180.0
F14—C30—F15107.1 (6)O1ii—K2—O7ii60.91 (12)
F13—C30—C29113.6 (6)O1—K2—O7ii119.09 (12)
F14—C30—C29110.4 (6)O3ii—K2—O7ii62.65 (13)
F15—C30—C29110.5 (6)O3—K2—O7ii117.35 (13)
O4—Eu1—O6104.33 (17)F13ii—K2—O7ii53.95 (11)
O4—Eu1—O576.78 (17)F13—K2—O7ii126.05 (11)
O6—Eu1—O571.91 (16)O1ii—K2—O7119.09 (12)
O4—Eu1—O370.88 (16)O1—K2—O760.91 (12)
O6—Eu1—O378.60 (17)O3ii—K2—O7117.35 (13)
O5—Eu1—O3128.55 (14)O3—K2—O762.65 (13)
O4—Eu1—O872.72 (18)F13ii—K2—O7126.05 (11)
O6—Eu1—O8149.11 (16)F13—K2—O753.95 (11)
O5—Eu1—O877.60 (16)O7ii—K2—O7180.0
O3—Eu1—O8126.22 (16)O1ii—K2—F766.14 (13)
O4—Eu1—O2139.43 (16)O1—K2—F7113.86 (13)
O6—Eu1—O294.56 (17)O3ii—K2—F7124.48 (12)
O5—Eu1—O275.54 (15)O3—K2—F755.52 (12)
O3—Eu1—O2149.11 (16)F13ii—K2—F761.71 (13)
O8—Eu1—O272.79 (16)F13—K2—F7118.29 (13)
O4—Eu1—O797.01 (17)O7ii—K2—F770.51 (12)
O6—Eu1—O7138.70 (16)O7—K2—F7109.49 (12)
O5—Eu1—O7148.45 (15)O1ii—K2—F7ii113.86 (13)
O3—Eu1—O775.60 (15)O1—K2—F7ii66.14 (13)
O8—Eu1—O771.08 (16)O3ii—K2—F7ii55.52 (12)
O2—Eu1—O791.44 (13)O3—K2—F7ii124.48 (12)
O4—Eu1—O1149.01 (16)F13ii—K2—F7ii118.29 (13)
O6—Eu1—O171.28 (16)F13—K2—F7ii61.71 (13)
O5—Eu1—O1127.16 (15)O7ii—K2—F7ii109.49 (12)
O3—Eu1—O178.24 (17)O7—K2—F7ii70.51 (12)
O8—Eu1—O1126.86 (13)F7—K2—F7ii180.0
O2—Eu1—O171.08 (16)O1ii—K2—F1125.14 (13)
O7—Eu1—O172.26 (15)O1—K2—F154.86 (13)
O4—Eu1—K2107.55 (12)O3ii—K2—F169.57 (13)
O6—Eu1—K293.08 (12)O3—K2—F1110.43 (13)
O5—Eu1—K2164.99 (11)F13ii—K2—F159.77 (12)
O3—Eu1—K244.52 (11)F13—K2—F1120.23 (12)
O8—Eu1—K2117.38 (12)O7ii—K2—F171.04 (12)
O2—Eu1—K2106.88 (10)O7—K2—F1108.96 (12)
O7—Eu1—K246.38 (11)F7—K2—F1121.13 (12)
O1—Eu1—K244.11 (10)F7ii—K2—F158.87 (12)
O4—Eu1—K192.65 (12)O1ii—K2—F1ii54.86 (13)
O6—Eu1—K1106.80 (12)O1—K2—F1ii125.14 (13)
O5—Eu1—K143.66 (10)O3ii—K2—F1ii110.43 (13)
O3—Eu1—K1163.53 (12)O3—K2—F1ii69.57 (13)
O8—Eu1—K144.13 (11)F13ii—K2—F1ii120.23 (12)
O2—Eu1—K147.16 (11)F13—K2—F1ii59.77 (12)
O7—Eu1—K1107.07 (11)O7ii—K2—F1ii108.96 (12)
O1—Eu1—K1118.19 (12)O7—K2—F1ii71.04 (12)
K2—Eu1—K1147.309 (12)F7—K2—F1ii58.87 (12)
C1—F1—K2120.3 (4)F7ii—K2—F1ii121.13 (12)
C5—F6—K1129.9 (4)F1—K2—F1ii180.0
C6—F7—K2121.4 (4)
F3—C1—C2—O1−161.2 (7)O7—C29—C30—F15−132.4 (7)
F1—C1—C2—O1−37.6 (9)C28—C29—C30—F1547.2 (9)
F2—C1—C2—O179.7 (8)C3—C2—O1—Eu120.3 (11)
F3—C1—C2—C319.0 (11)C1—C2—O1—Eu1−159.5 (5)
F1—C1—C2—C3142.6 (7)O4—Eu1—O1—C2170.4 (6)
F2—C1—C2—C3−100.1 (8)O6—Eu1—O1—C283.7 (6)
O1—C2—C3—C4−4.5 (12)O5—Eu1—O1—C235.6 (7)
C1—C2—C3—C4175.2 (7)O3—Eu1—O1—C2165.5 (6)
C2—C3—C4—O2−4.5 (12)O8—Eu1—O1—C2−67.8 (6)
C2—C3—C4—C5174.8 (7)O2—Eu1—O1—C2−18.2 (6)
O2—C4—C5—F4−132.8 (7)O7—Eu1—O1—C2−116.1 (6)
C3—C4—C5—F447.8 (9)C3—C4—O2—Eu1−2.8 (11)
O2—C4—C5—F5105.4 (7)C5—C4—O2—Eu1177.9 (4)
C3—C4—C5—F5−74.0 (9)O4—Eu1—O2—C4−176.9 (5)
O2—C4—C5—F6−11.5 (9)O6—Eu1—O2—C4−58.5 (6)
C3—C4—C5—F6169.1 (6)O5—Eu1—O2—C4−128.5 (6)
F8—C6—C7—O3165.1 (7)O3—Eu1—O2—C416.8 (7)
F9—C6—C7—O3−73.2 (8)O8—Eu1—O2—C4150.2 (6)
F7—C6—C7—O341.8 (10)O7—Eu1—O2—C480.6 (6)
F8—C6—C7—C8−15.8 (11)O1—Eu1—O2—C49.9 (6)
F9—C6—C7—C8106.0 (9)C8—C7—O3—Eu1−13.1 (12)
F7—C6—C7—C8−139.1 (8)C6—C7—O3—Eu1165.9 (5)
O3—C7—C8—C93.2 (14)O4—Eu1—O3—C710.3 (6)
C6—C7—C8—C9−175.8 (7)O6—Eu1—O3—C7−99.4 (6)
C7—C8—C9—O45.1 (13)O5—Eu1—O3—C7−43.9 (7)
C7—C8—C9—C10−175.6 (8)O8—Eu1—O3—C760.2 (7)
O4—C9—C10—C1115.6 (11)O2—Eu1—O3—C7−179.1 (6)
C8—C9—C10—C11−163.8 (9)O7—Eu1—O3—C7113.1 (7)
O4—C9—C10—C15−168.9 (8)O1—Eu1—O3—C7−172.4 (6)
C8—C9—C10—C1511.7 (12)C8—C9—O4—Eu1−3.8 (12)
C15—C10—C11—C1211.7 (16)C10—C9—O4—Eu1176.9 (5)
C9—C10—C11—C12−172.9 (9)O6—Eu1—O4—C970.1 (8)
C10—C11—C12—C13−8.0 (17)O5—Eu1—O4—C9137.2 (8)
C11—C12—C13—C143.1 (16)O3—Eu1—O4—C9−2.2 (7)
C12—C13—C14—C15−1.8 (16)O8—Eu1—O4—C9−141.9 (8)
C11—C10—C15—C14−9.7 (16)O2—Eu1—O4—C9−174.8 (7)
C9—C10—C15—C14175.0 (8)O7—Eu1—O4—C9−74.2 (8)
C13—C14—C15—C104.9 (16)O1—Eu1—O4—C9−7.3 (10)
F10—C16—C17—O5−75.9 (8)C18—C17—O5—Eu1−10.9 (13)
F11—C16—C17—O544.5 (9)C16—C17—O5—Eu1165.1 (5)
F12—C16—C17—O5166.3 (7)O4—Eu1—O5—C17−103.0 (7)
F10—C16—C17—C18100.6 (9)O6—Eu1—O5—C177.1 (6)
F11—C16—C17—C18−139.0 (8)O3—Eu1—O5—C17−51.1 (7)
F12—C16—C17—C18−17.2 (11)O8—Eu1—O5—C17−177.9 (7)
O5—C17—C18—C195.4 (15)O2—Eu1—O5—C17107.0 (7)
C16—C17—C18—C19−170.5 (8)O7—Eu1—O5—C17175.2 (6)
C17—C18—C19—O61.4 (15)O1—Eu1—O5—C1755.0 (7)
C17—C18—C19—C20177.2 (8)C18—C19—O6—Eu1−2.4 (14)
O6—C19—C20—C2115.3 (12)C20—C19—O6—Eu1−178.4 (5)
C18—C19—C20—C21−161.0 (10)O4—Eu1—O6—C1969.7 (8)
O6—C19—C20—C25−165.8 (8)O5—Eu1—O6—C19−0.9 (7)
C18—C19—C20—C2518.0 (13)O3—Eu1—O6—C19136.4 (8)
C25—C20—C21—C22−3.7 (17)O8—Eu1—O6—C19−10.5 (10)
C19—C20—C21—C22175.3 (9)O2—Eu1—O6—C19−74.1 (8)
C20—C21—C22—C233.0 (18)O7—Eu1—O6—C19−171.5 (7)
C21—C22—C23—C240.7 (18)O1—Eu1—O6—C19−142.3 (8)
C22—C23—C24—C25−3.6 (18)C28—C29—O7—Eu10.9 (11)
C21—C20—C25—C240.5 (15)C30—C29—O7—Eu1−179.5 (5)
C19—C20—C25—C24−178.4 (9)O4—Eu1—O7—C29−60.7 (6)
C23—C24—C25—C203.0 (16)O6—Eu1—O7—C29178.1 (6)
F17—C26—C27—O879.2 (8)O5—Eu1—O7—C2915.4 (8)
F18—C26—C27—O8−158.8 (7)O3—Eu1—O7—C29−128.9 (6)
F16—C26—C27—O8−40.0 (9)O8—Eu1—O7—C298.3 (6)
F17—C26—C27—C28−99.1 (8)O2—Eu1—O7—C2979.5 (6)
F18—C26—C27—C2822.8 (10)O1—Eu1—O7—C29149.1 (6)
F16—C26—C27—C28141.7 (7)C28—C27—O8—Eu118.7 (12)
O8—C27—C28—C29−1.5 (12)C26—C27—O8—Eu1−159.4 (5)
C26—C27—C28—C29176.6 (6)O4—Eu1—O8—C2786.5 (7)
C27—C28—C29—O7−8.5 (12)O6—Eu1—O8—C27175.6 (6)
C27—C28—C29—C30172.0 (7)O5—Eu1—O8—C27166.3 (7)
O7—C29—C30—F13−13.5 (10)O3—Eu1—O8—C2737.2 (7)
C28—C29—C30—F13166.1 (6)O2—Eu1—O8—C27−115.2 (7)
O7—C29—C30—F14109.3 (7)O7—Eu1—O8—C27−17.5 (6)
C28—C29—C30—F14−71.1 (9)O1—Eu1—O8—C27−66.3 (7)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5047).

References

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