metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 66| Part 7| July 2010| Pages m799-m800

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

aDepartment of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station, A5300, Austin, Texas 78712, USA
*Correspondence e-mail: bholliday@cm.utexas.edu

(Received 12 May 2010; accepted 4 June 2010; online 16 June 2010)

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[Eliseeva, S. V. & Bunzli, J.-C. G. (2010). Chem. Soc. Rev. 39, 189-227.]); de Bettencourt-Dias (1997[Bettencourt-Dias, A. de (1997). J. Chem. Soc. Dalton Trans. pp. 2229-2241.]); Stanley et al. (2010[Stanley, J. M., Zhu, X., Yang, X. & Holliday, B. J. (2010). Inorg. Chem. 49, 2035-2037.]); Chen & Holliday (2008[Chen, X.-Y. & Holliday, B. J. (2008). J. Am. Chem. Soc. 130, 1546-1547.]). For similar structures, see: Nockemann et al. (2005[Nockemann, P., Beurer, E., Driesen, K., Van Deun, R., Van Hecke, K., Van Meervelt, L. & Binnemans, K. (2005). Chem. Commun. pp. 4354-4356.]); Burns & Danford (1969[Burns, J. H. & Danford, M. D. (1969). Inorg. Chem. 8, 1780-1784.]). The twin law was determined using TwinSolve (Rigaku/MSC, 2002[Rigaku/MSC (2002). TwinSolve. Rigaku/MSC, The Woodlands, Texas, USA.]).

[Scheme 1]

Experimental

Crystal data
  • K[Eu(C5HF6O2)2(C10H6F3O2)2]

  • Mr = 1035.47

  • Triclinic, [P \overline 1]

  • 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[Higashi, T. (2001). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.789, Tmax = 0.941

  • 25336 measured reflections

  • 25336 independent reflections

  • 22905 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.096

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Eu1—O4 2.294 (5)
Eu1—O6 2.315 (5)
Eu1—O5 2.367 (4)
Eu1—O3 2.368 (4)
Eu1—O8 2.394 (5)
Eu1—O2 2.400 (5)
Eu1—O7 2.412 (4)
Eu1—O1 2.413 (5)

Data collection: CrystalClear (Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]) within WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and POV-RAY (Persistence of Vision, 2004[Persistence of Vision (2004). Persistence of Vision (TM) Raytracer (POV-RAY). Persistence of Vision Pty. Ltd, Williamstown, Victoria, Australia. http://www.povray.org/ .]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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].
Potassium bis(1,1,1,5,5,5-hexafluoropentane-2,4-dionato)bis(4,4,4-trifluoro-1- phenylbutane-1,3-dionato)europate(III) top
Crystal data top
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 top
Rigaku AFC12 with Saturn 724+ CCD
diffractometer
25336 independent reflections
Radiation source: fine-focus sealed tube22905 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
ω–scansθmax = 25.0°, θmin = 4.7°
Absorption correction: multi-scan
(ABSCOR; Higashi, 2001)
h = 1313
Tmin = 0.789, Tmax = 0.941k = 1414
25336 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.096Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 3.00 w = 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
Crystal data top
K[Eu(C5HF6O2)2(C10H6F3O2)2]γ = 71.726 (8)°
Mr = 1035.47V = 1737.1 (5) Å3
Triclinic, P1Z = 2
a = 11.737 (2) ÅMo Kα radiation
b = 12.468 (2) ŵ = 2.07 mm1
c = 13.788 (3) ÅT = 100 K
α = 68.457 (8)°0.12 × 0.06 × 0.03 mm
β = 71.791 (8)°
Data collection top
Rigaku AFC12 with Saturn 724+ CCD
diffractometer
25336 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 2001)
22905 reflections with I > 2σ(I)
Tmin = 0.789, Tmax = 0.941Rint = 0.000
25336 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0960 restraints
wR(F2) = 0.197H-atom parameters constrained
S = 3.00Δρmax = 3.65 e Å3
25336 reflectionsΔρmin = 3.79 e Å3
527 parameters
Special details top

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

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
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)
C50.0953 (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)
H280.73720.00310.62490.069*
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)
H170.30150.09340.03490.079*
C230.1444 (12)0.0361 (9)0.0438 (9)0.076 (4)
H180.15080.00620.00340.091*
C240.0410 (10)0.0374 (8)0.1331 (8)0.068 (3)
H190.02420.00110.14500.081*
C250.0430 (9)0.0959 (8)0.2015 (7)0.049 (2)
H200.02110.09630.26390.059*
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)
F40.1848 (4)0.6928 (5)0.2024 (4)0.0598 (14)
F50.0824 (5)0.8077 (4)0.2013 (4)0.0570 (15)
F60.1285 (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)
F110.0526 (4)0.2664 (3)0.5961 (3)0.0385 (10)
F120.0690 (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) top
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, º) top
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—O1161.2 (7)O7—C29—C30—F15132.4 (7)
F1—C1—C2—O137.6 (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—Eu1159.5 (5)
F1—C1—C2—C3142.6 (7)O4—Eu1—O1—C2170.4 (6)
F2—C1—C2—C3100.1 (8)O6—Eu1—O1—C283.7 (6)
O1—C2—C3—C44.5 (12)O5—Eu1—O1—C235.6 (7)
C1—C2—C3—C4175.2 (7)O3—Eu1—O1—C2165.5 (6)
C2—C3—C4—O24.5 (12)O8—Eu1—O1—C267.8 (6)
C2—C3—C4—C5174.8 (7)O2—Eu1—O1—C218.2 (6)
O2—C4—C5—F4132.8 (7)O7—Eu1—O1—C2116.1 (6)
C3—C4—C5—F447.8 (9)C3—C4—O2—Eu12.8 (11)
O2—C4—C5—F5105.4 (7)C5—C4—O2—Eu1177.9 (4)
C3—C4—C5—F574.0 (9)O4—Eu1—O2—C4176.9 (5)
O2—C4—C5—F611.5 (9)O6—Eu1—O2—C458.5 (6)
C3—C4—C5—F6169.1 (6)O5—Eu1—O2—C4128.5 (6)
F8—C6—C7—O3165.1 (7)O3—Eu1—O2—C416.8 (7)
F9—C6—C7—O373.2 (8)O8—Eu1—O2—C4150.2 (6)
F7—C6—C7—O341.8 (10)O7—Eu1—O2—C480.6 (6)
F8—C6—C7—C815.8 (11)O1—Eu1—O2—C49.9 (6)
F9—C6—C7—C8106.0 (9)C8—C7—O3—Eu113.1 (12)
F7—C6—C7—C8139.1 (8)C6—C7—O3—Eu1165.9 (5)
O3—C7—C8—C93.2 (14)O4—Eu1—O3—C710.3 (6)
C6—C7—C8—C9175.8 (7)O6—Eu1—O3—C799.4 (6)
C7—C8—C9—O45.1 (13)O5—Eu1—O3—C743.9 (7)
C7—C8—C9—C10175.6 (8)O8—Eu1—O3—C760.2 (7)
O4—C9—C10—C1115.6 (11)O2—Eu1—O3—C7179.1 (6)
C8—C9—C10—C11163.8 (9)O7—Eu1—O3—C7113.1 (7)
O4—C9—C10—C15168.9 (8)O1—Eu1—O3—C7172.4 (6)
C8—C9—C10—C1511.7 (12)C8—C9—O4—Eu13.8 (12)
C15—C10—C11—C1211.7 (16)C10—C9—O4—Eu1176.9 (5)
C9—C10—C11—C12172.9 (9)O6—Eu1—O4—C970.1 (8)
C10—C11—C12—C138.0 (17)O5—Eu1—O4—C9137.2 (8)
C11—C12—C13—C143.1 (16)O3—Eu1—O4—C92.2 (7)
C12—C13—C14—C151.8 (16)O8—Eu1—O4—C9141.9 (8)
C11—C10—C15—C149.7 (16)O2—Eu1—O4—C9174.8 (7)
C9—C10—C15—C14175.0 (8)O7—Eu1—O4—C974.2 (8)
C13—C14—C15—C104.9 (16)O1—Eu1—O4—C97.3 (10)
F10—C16—C17—O575.9 (8)C18—C17—O5—Eu110.9 (13)
F11—C16—C17—O544.5 (9)C16—C17—O5—Eu1165.1 (5)
F12—C16—C17—O5166.3 (7)O4—Eu1—O5—C17103.0 (7)
F10—C16—C17—C18100.6 (9)O6—Eu1—O5—C177.1 (6)
F11—C16—C17—C18139.0 (8)O3—Eu1—O5—C1751.1 (7)
F12—C16—C17—C1817.2 (11)O8—Eu1—O5—C17177.9 (7)
O5—C17—C18—C195.4 (15)O2—Eu1—O5—C17107.0 (7)
C16—C17—C18—C19170.5 (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—Eu12.4 (14)
O6—C19—C20—C2115.3 (12)C20—C19—O6—Eu1178.4 (5)
C18—C19—C20—C21161.0 (10)O4—Eu1—O6—C1969.7 (8)
O6—C19—C20—C25165.8 (8)O5—Eu1—O6—C190.9 (7)
C18—C19—C20—C2518.0 (13)O3—Eu1—O6—C19136.4 (8)
C25—C20—C21—C223.7 (17)O8—Eu1—O6—C1910.5 (10)
C19—C20—C21—C22175.3 (9)O2—Eu1—O6—C1974.1 (8)
C20—C21—C22—C233.0 (18)O7—Eu1—O6—C19171.5 (7)
C21—C22—C23—C240.7 (18)O1—Eu1—O6—C19142.3 (8)
C22—C23—C24—C253.6 (18)C28—C29—O7—Eu10.9 (11)
C21—C20—C25—C240.5 (15)C30—C29—O7—Eu1179.5 (5)
C19—C20—C25—C24178.4 (9)O4—Eu1—O7—C2960.7 (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—O8158.8 (7)O3—Eu1—O7—C29128.9 (6)
F16—C26—C27—O840.0 (9)O8—Eu1—O7—C298.3 (6)
F17—C26—C27—C2899.1 (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—C291.5 (12)C26—C27—O8—Eu1159.4 (5)
C26—C27—C28—C29176.6 (6)O4—Eu1—O8—C2786.5 (7)
C27—C28—C29—O78.5 (12)O6—Eu1—O8—C27175.6 (6)
C27—C28—C29—C30172.0 (7)O5—Eu1—O8—C27166.3 (7)
O7—C29—C30—F1313.5 (10)O3—Eu1—O8—C2737.2 (7)
C28—C29—C30—F13166.1 (6)O2—Eu1—O8—C27115.2 (7)
O7—C29—C30—F14109.3 (7)O7—Eu1—O8—C2717.5 (6)
C28—C29—C30—F1471.1 (9)O1—Eu1—O8—C2766.3 (7)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaK[Eu(C5HF6O2)2(C10H6F3O2)2]
Mr1035.47
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)11.737 (2), 12.468 (2), 13.788 (3)
α, β, γ (°)68.457 (8), 71.791 (8), 71.726 (8)
V3)1737.1 (5)
Z2
Radiation typeMo Kα
µ (mm1)2.07
Crystal size (mm)0.12 × 0.06 × 0.03
Data collection
DiffractometerRigaku AFC12 with Saturn 724+ CCD
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 2001)
Tmin, Tmax0.789, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections
25336, 25336, 22905
Rint0.000
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.096, 0.197, 3.00
No. of reflections25336
No. of parameters527
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)3.65, 3.79

Computer programs: CrystalClear (Rigaku/MSC, 2008), SIR97 (Altomare et al., 1999) within WinGX (Farrugia, 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and POV-RAY (Persistence of Vision, 2004).

Selected bond lengths (Å) top
Eu1—O42.294 (5)Eu1—O82.394 (5)
Eu1—O62.315 (5)Eu1—O22.400 (5)
Eu1—O52.367 (4)Eu1—O72.412 (4)
Eu1—O32.368 (4)Eu1—O12.413 (5)
 

Acknowledgements

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.

References

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Volume 66| Part 7| July 2010| Pages m799-m800
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