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The title complex, (C7H11N2)[Eu(C8H4F3O2S)4] or [DMAP][Eu(TTA)4], features a trivalent EuIII cation that is eight-coordinated by eight O atoms derived from four chelating β-diketonate ligands. The range of Eu—O bond distances is 2.3594 (18)–2.4896 (18) Å. The coordination polyhedron is based on a distorted tetra­gonal anti­prism. N—H...O hydrogen bonding connects the cation to the anion. There is twofold flip disorder of two thienyl rings with occupancies in the approximate ratio 2:1; one CF3 group is equally disordered over two orientations, and another shows extensive disorder, modelled in four different orientations with unequal occupancies.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045667/tk2189sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045667/tk2189Isup2.hkl
Contains datablock I

CCDC reference: 663621

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.032
  • wR factor = 0.085
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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Alert level B PLAT215_ALERT_3_B Disordered F5 has ADP max/min Ratio ....... 4.80 PLAT215_ALERT_3_B Disordered F5' has ADP max/min Ratio ....... 4.80 PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.90 Ratio PLAT220_ALERT_2_B Large Non-Solvent F Ueq(max)/Ueq(min) ... 3.66 Ratio
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.50 prola PLAT213_ALERT_2_C Atom C11 has ADP max/min Ratio ............. 3.80 prola PLAT213_ALERT_2_C Atom F10 has ADP max/min Ratio ............. 3.20 prola PLAT213_ALERT_2_C Atom F10A has ADP max/min Ratio ............. 3.20 prola PLAT213_ALERT_2_C Atom F10B has ADP max/min Ratio ............. 3.20 prola PLAT213_ALERT_2_C Atom F10C has ADP max/min Ratio ............. 3.20 prola PLAT213_ALERT_2_C Atom C17' has ADP max/min Ratio ............. 3.80 prola PLAT215_ALERT_3_C Disordered F6 has ADP max/min Ratio ....... 3.10 PLAT215_ALERT_3_C Disordered F6' has ADP max/min Ratio ....... 3.10 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F5 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for F5' PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT301_ALERT_3_C Main Residue Disorder ......................... 20.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 11.60 Deg. F4' -C16 -F4 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.40 Deg. F5 -C16 -F5' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. F6' -C16 -F6 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 3.00 Deg. C28 -C29 -C28' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.50 Deg. F12B -C32 -F11A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.20 Deg. F12B -C32 -F12C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 21.90 Deg. F10A -C32 -F10 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.20 Deg. F10A -C32 -F11B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.20 Deg. F10 -C32 -F10C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 42.60 Deg. F11B -C32 -F11C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 20.70 Deg. F12C -C32 -F12 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 33.60 Deg. F12A -C32 -F12 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.30 Deg. F10C -C32 -F10B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.50 Deg. F12A -C32 -F10B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.90 Deg. F11A -C32 -F11 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 21.80 Deg. F11C -C32 -F11 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 76
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 36 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 31 ALERT type 2 Indicator that the structure model may be wrong or deficient 8 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The structure of the title complex, [DMAP][Eu(TTA)4] (I), Fig. 1, shows the trivalent Eu cation to be 8-coordinated by eight O atoms derived from four chelating β-diketonate ligands. The coordination polyhedron can be best described as a distorted tetragonal antiprism in which the square planes are defined by the O1, O2, O5 & O6 atoms and the atoms O3, O4, O7 & O8. The 4-dimethylaminopyridinium cation forms a N—H···O hydrogen bond to the O6 atom (Table 1). Complex (I) has intensive photoluminescence (PL) at room temperature. The corresponding 4-aminopyridinium complex, [4-aminopyridinium][Eu(TTA)4] has mechanoluminescence (ML) properties (Chen et al., 2001), which was attributed to the disorder in the thienyl rings and CF3 groups (Sweeting & Rheingold, 1987). However, (I) also has disorder in the thienyl rings and CF3 groups (see Experimental) but does not exhibit ML.

Related literature top

For the corresponding 4-aminopyridinium complex, see Chen et al. (2001). For related literature, see: Bauer et al. (1964); Sweeting & Rheingold (1987).

Experimental top

All chemicals were of analytical grade and were used without further purification. Complex (I) was prepared according to method C in Bauer et al., 1964. Pale-yellow products were obtained. Purification by recrystallization was accomplished by room temperature evaporation of a CH2Cl2 solution of (I). Single crystal suitable for X-ray analysis were obtained from an EtOH solution of (I); m. pt. 422 K.

Refinement top

Two of the four thienyl rings as well as the four CF3 groups are disordered. The positional disorder of F atoms, F4, F5 and F6, was modelled anisotropically over two positions with site occupancy factors for the primed and unprimed atoms equalling 0.5 (from refinement). The F10, F11 and F12 atoms were modelled over four positions with the site occupancy factors of 0.472, 0.274, 0.099 and 0.156 for atoms (F10, F11, F12), (F10A, F11A, F12A), (F10B, F11B, F12B) and (F10C, F11C, F12C), respectively, as determined from least-squares refinement; of these, the F10, F11, & F12 atoms were refined with anisotropic displacement parameters.

Two of the four thienyl rings were disordered and modelled anisotropically over two orientations with refined occupancy factors of S3:S3'=0.668 (5):0.332 and S4:S4'=0.656 (4):0.344, respectively, obtained from least-squares refinement.

The N1—H atom was located by difference Fourier synthesis and refined without constraint so that N—H = 0.87 Å. The C-bound H atoms were included in the riding model approximation with C—H = 0.95 - 0.98 Å, and with Uiso(H) = 1.2Ueq(C). The highest residual electron density peak is 0.78 Å from the Eu atom, and the deepest hole is 0.62 Å from the S2 atom.

Structure description top

The structure of the title complex, [DMAP][Eu(TTA)4] (I), Fig. 1, shows the trivalent Eu cation to be 8-coordinated by eight O atoms derived from four chelating β-diketonate ligands. The coordination polyhedron can be best described as a distorted tetragonal antiprism in which the square planes are defined by the O1, O2, O5 & O6 atoms and the atoms O3, O4, O7 & O8. The 4-dimethylaminopyridinium cation forms a N—H···O hydrogen bond to the O6 atom (Table 1). Complex (I) has intensive photoluminescence (PL) at room temperature. The corresponding 4-aminopyridinium complex, [4-aminopyridinium][Eu(TTA)4] has mechanoluminescence (ML) properties (Chen et al., 2001), which was attributed to the disorder in the thienyl rings and CF3 groups (Sweeting & Rheingold, 1987). However, (I) also has disorder in the thienyl rings and CF3 groups (see Experimental) but does not exhibit ML.

For the corresponding 4-aminopyridinium complex, see Chen et al. (2001). For related literature, see: Bauer et al. (1964); Sweeting & Rheingold (1987).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1998); software used to prepare material for publication: SHELXTL (Siemens, 1998).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. H atoms have been omitted for clarity.
4-Dimethylaminopyridinium tetrakis[3,3,3-trifluoro-1-(2-thienylcarbonyl)prop-1-en-2-olato]europate(III) top
Crystal data top
(C7H11N2)[Eu(C8H4F3O2S)4]Dx = 1.738 Mg m3
Mr = 1159.83Melting point: 422 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 77909 reflections
a = 20.0202 (4) Åθ = 3.0–27.5°
b = 18.9160 (3) ŵ = 1.71 mm1
c = 23.4108 (4) ÅT = 93 K
V = 8865.7 (3) Å3Block, light yellow
Z = 80.62 × 0.45 × 0.23 mm
F(000) = 4592
Data collection top
Rigaku R-AXIS RAPID
diffractometer
10137 independent reflections
Radiation source: Rotating Anode9604 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: numerical
(ABSCOR; Higashi, 1999)
h = 2521
Tmin = 0.418, Tmax = 0.695k = 2424
82834 measured reflectionsl = 3030
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0426P)2 + 19.8P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
10137 reflectionsΔρmax = 1.29 e Å3
725 parametersΔρmin = 1.10 e Å3
76 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00046 (5)
Crystal data top
(C7H11N2)[Eu(C8H4F3O2S)4]V = 8865.7 (3) Å3
Mr = 1159.83Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 20.0202 (4) ŵ = 1.71 mm1
b = 18.9160 (3) ÅT = 93 K
c = 23.4108 (4) Å0.62 × 0.45 × 0.23 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
10137 independent reflections
Absorption correction: numerical
(ABSCOR; Higashi, 1999)
9604 reflections with I > 2σ(I)
Tmin = 0.418, Tmax = 0.695Rint = 0.048
82834 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03276 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0426P)2 + 19.8P]
where P = (Fo2 + 2Fc2)/3
10137 reflectionsΔρmax = 1.29 e Å3
725 parametersΔρmin = 1.10 e Å3
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
xyzUiso*/UeqOcc. (<1)
Eu0.597426 (6)0.721987 (6)0.360975 (5)0.01510 (6)
S10.60799 (4)0.57483 (4)0.17677 (3)0.03073 (16)
S20.39615 (5)0.83825 (6)0.44619 (5)0.0506 (3)
F10.39394 (12)0.59604 (15)0.43360 (8)0.0594 (7)
F20.34744 (12)0.57253 (18)0.35390 (9)0.0750 (10)
F30.35621 (11)0.67993 (16)0.38226 (13)0.0737 (8)
F70.58142 (9)0.56142 (11)0.53956 (8)0.0405 (5)
F80.65626 (10)0.63695 (11)0.56345 (7)0.0402 (5)
F90.68492 (10)0.53054 (10)0.54391 (7)0.0390 (5)
O10.57171 (10)0.64663 (11)0.28185 (8)0.0270 (4)
O20.49679 (9)0.66181 (10)0.38064 (8)0.0228 (4)
O30.52853 (9)0.79803 (11)0.41529 (8)0.0232 (4)
O40.66577 (9)0.79900 (10)0.41878 (8)0.0220 (4)
O50.68395 (9)0.63666 (10)0.35019 (8)0.0215 (4)
O60.61699 (9)0.65975 (10)0.45317 (7)0.0199 (4)
O70.53810 (9)0.79814 (11)0.29734 (8)0.0243 (4)
O80.67192 (8)0.76383 (10)0.29028 (7)0.0172 (3)
N10.53190 (12)0.78441 (13)0.03754 (10)0.0228 (5)
N20.37594 (13)0.73141 (14)0.14289 (10)0.0276 (5)
C10.5848 (2)0.5117 (2)0.12886 (14)0.0430 (8)
H10.61120.49790.09700.052*
C20.5244 (2)0.4834 (2)0.14134 (15)0.0509 (10)
H20.50390.44770.11890.061*
C30.49566 (16)0.51149 (15)0.18959 (11)0.0280 (6)
H30.45340.49720.20410.034*
C40.53614 (15)0.56404 (15)0.21516 (11)0.0246 (5)
C50.52640 (13)0.60478 (14)0.26746 (11)0.0218 (5)
C60.46612 (14)0.59541 (16)0.29869 (11)0.0273 (6)
H60.43150.56750.28260.033*
C70.45655 (14)0.62543 (16)0.35122 (11)0.0251 (6)
C80.38772 (15)0.61804 (15)0.37990 (10)0.0425 (9)
C90.3482 (2)0.8823 (3)0.4915 (2)0.0627 (13)
H90.30080.88090.49030.075*
C100.3826 (3)0.9204 (2)0.5301 (2)0.0659 (14)
H100.36060.94720.55870.079*
C110.45524 (16)0.91853 (16)0.52591 (13)0.0331 (7)
H110.48700.94340.54830.040*
C120.46776 (16)0.86778 (15)0.47749 (13)0.0300 (6)
C130.53184 (14)0.84155 (14)0.45560 (11)0.0231 (5)
C140.59243 (15)0.86281 (16)0.48075 (12)0.0279 (6)
H140.59160.89570.51140.034*
C150.65323 (14)0.83693 (15)0.46199 (11)0.0243 (5)
C160.71490 (14)0.85150 (14)0.49939 (11)0.0351 (7)
C210.70624 (11)0.58265 (12)0.37441 (10)0.0169 (5)
C220.69243 (12)0.56499 (14)0.43225 (11)0.0198 (5)
H220.71250.52390.44810.024*
C230.65101 (12)0.60529 (14)0.46600 (10)0.0190 (5)
C240.64375 (11)0.58252 (12)0.52873 (10)0.0281 (6)
C290.54665 (12)0.82280 (13)0.24797 (10)0.0205 (5)
C300.60626 (13)0.81424 (15)0.21592 (11)0.0217 (5)
H300.60730.82950.17730.026*
C310.66273 (12)0.78427 (13)0.23958 (10)0.0178 (5)
C320.72446 (12)0.77568 (12)0.20115 (9)0.0268 (6)
C330.49300 (14)0.72594 (14)0.11988 (12)0.0227 (5)
H330.50210.69750.15240.027*
C340.54349 (13)0.74485 (15)0.08441 (11)0.0231 (5)
H340.58780.73000.09270.028*
C350.46985 (14)0.80629 (16)0.02486 (11)0.0251 (5)
H350.46280.83380.00860.030*
C360.41688 (14)0.79004 (16)0.05877 (12)0.0242 (5)
H360.37350.80650.04920.029*
C370.42670 (13)0.74846 (14)0.10856 (10)0.0199 (5)
C380.38690 (17)0.68721 (18)0.19277 (14)0.0374 (7)
H38A0.40210.64030.18060.045*
H38B0.34510.68260.21420.045*
H38C0.42090.70890.21720.045*
C390.30806 (14)0.7547 (2)0.12963 (15)0.0341 (7)
H39A0.30720.80640.12640.041*
H39B0.27770.73970.16020.041*
H39C0.29370.73370.09340.041*
S30.76027 (15)0.55120 (13)0.26924 (11)0.0207 (5)0.668 (4)
C170.8112 (8)0.4800 (7)0.2609 (5)0.021 (3)0.668 (4)
H170.83330.46830.22630.025*0.668 (4)
C180.8162 (7)0.4416 (8)0.3103 (5)0.022 (2)0.668 (4)
H180.83840.39740.31270.026*0.668 (4)
C190.7845 (7)0.4749 (6)0.3580 (5)0.0195 (18)0.668 (4)
H190.78700.45850.39630.023*0.668 (4)
C200.74887 (11)0.53566 (11)0.34022 (8)0.0169 (5)0.668 (4)
S40.41641 (14)0.8617 (2)0.25791 (17)0.0364 (8)0.656 (5)
C250.3827 (7)0.9126 (9)0.2054 (5)0.032 (3)0.656 (5)
H250.33610.92180.20450.039*0.656 (5)
C260.4241 (5)0.9401 (11)0.1645 (7)0.033 (3)0.656 (5)
H260.41350.97470.13640.039*0.656 (5)
C270.4867 (5)0.9055 (8)0.1732 (4)0.031 (3)0.656 (5)
H270.52280.91010.14720.037*0.656 (5)
C280.4912 (6)0.864 (2)0.2234 (13)0.0240 (17)0.656 (5)
F40.7630 (6)0.8826 (11)0.4694 (7)0.025 (2)0.50
F50.7102 (15)0.8890 (16)0.5472 (8)0.085 (4)0.50
F60.738 (8)0.792 (5)0.522 (8)0.0916 (12)0.50
F100.7128 (4)0.7831 (6)0.14554 (14)0.045 (2)0.472 (7)
F110.7484 (3)0.7097 (2)0.2073 (3)0.0290 (12)0.472 (7)
F120.7734 (3)0.8167 (4)0.2210 (4)0.0457 (18)0.472 (7)
S3'0.7835 (4)0.4610 (3)0.3669 (3)0.0217 (11)0.332 (4)
C17'0.8212 (15)0.4430 (17)0.3035 (6)0.030 (7)0.332 (4)
H17'0.85370.40710.29770.036*0.332 (4)
C18'0.7980 (17)0.4876 (16)0.2619 (10)0.022 (3)0.332 (4)
H18'0.80330.47790.22240.026*0.332 (4)
C19'0.7653 (14)0.5498 (12)0.2824 (4)0.042 (8)0.332 (4)
H19'0.75640.59190.26150.050*0.332 (4)
C20'0.74887 (11)0.53566 (11)0.34022 (8)0.0169 (5)0.332 (4)
S4'0.4999 (3)0.9122 (4)0.1631 (3)0.0231 (10)0.344 (5)
C25'0.4167 (5)0.929 (2)0.1690 (14)0.032 (6)0.344 (5)
H25'0.39390.94830.13710.038*0.344 (5)
C26'0.3811 (14)0.9151 (17)0.2177 (10)0.031 (4)0.344 (5)
H26'0.33880.93260.22940.037*0.344 (5)
C27'0.4254 (7)0.8673 (10)0.2461 (10)0.027 (5)0.344 (5)
H27'0.41230.84160.27910.033*0.344 (5)
C28'0.4902 (11)0.861 (4)0.222 (3)0.0240 (17)0.344 (5)
F4'0.7693 (6)0.8701 (11)0.4706 (7)0.037 (4)0.50
F5'0.6989 (15)0.9023 (15)0.5362 (9)0.085 (4)0.50
F6'0.738 (8)0.792 (5)0.522 (8)0.0916 (12)0.50
F10A0.7067 (9)0.7574 (9)0.1485 (3)0.045 (2)0.274 (5)
F11A0.7679 (5)0.7273 (5)0.2187 (4)0.0290 (12)0.274 (5)
F12A0.7570 (6)0.8368 (4)0.1960 (6)0.0457 (18)0.274 (5)
F10B0.7361 (11)0.8384 (5)0.1770 (10)0.0447 (4)0.099 (5)
F11B0.7135 (8)0.7314 (9)0.1580 (6)0.0290 (12)0.099 (5)
F12B0.7814 (6)0.7573 (14)0.2261 (7)0.0457 (18)0.099 (5)
F10C0.7226 (11)0.8152 (12)0.1542 (7)0.045 (2)0.156 (7)
F11C0.7331 (8)0.7072 (3)0.1903 (7)0.0290 (12)0.156 (7)
F12C0.7822 (6)0.7938 (14)0.2251 (10)0.0457 (18)0.156 (7)
H1N0.5629 (19)0.798 (2)0.0139 (16)0.036 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Eu0.01078 (8)0.01810 (8)0.01641 (8)0.00051 (4)0.00067 (4)0.00262 (4)
S10.0312 (4)0.0349 (4)0.0261 (3)0.0025 (3)0.0008 (3)0.0050 (3)
S20.0327 (4)0.0486 (6)0.0705 (7)0.0121 (4)0.0194 (4)0.0144 (5)
F10.0613 (14)0.0929 (19)0.0240 (9)0.0511 (13)0.0071 (9)0.0015 (10)
F20.0443 (13)0.143 (3)0.0381 (11)0.0603 (16)0.0124 (10)0.0339 (14)
F30.0276 (11)0.102 (2)0.091 (2)0.0076 (13)0.0156 (12)0.0096 (17)
F70.0346 (10)0.0516 (12)0.0353 (10)0.0055 (9)0.0185 (8)0.0140 (9)
F80.0487 (11)0.0538 (12)0.0182 (8)0.0156 (9)0.0056 (7)0.0067 (8)
F90.0433 (11)0.0482 (12)0.0254 (8)0.0211 (9)0.0091 (7)0.0135 (8)
O10.0211 (9)0.0323 (11)0.0275 (10)0.0061 (8)0.0037 (8)0.0129 (8)
O20.0188 (9)0.0296 (10)0.0200 (8)0.0077 (7)0.0003 (7)0.0015 (7)
O30.0203 (9)0.0272 (10)0.0222 (9)0.0053 (8)0.0034 (7)0.0040 (7)
O40.0201 (9)0.0260 (10)0.0199 (8)0.0049 (7)0.0025 (7)0.0060 (7)
O50.0227 (9)0.0206 (9)0.0213 (8)0.0063 (7)0.0064 (7)0.0032 (7)
O60.0154 (8)0.0259 (9)0.0186 (8)0.0041 (7)0.0020 (7)0.0014 (7)
O70.0176 (9)0.0365 (11)0.0186 (9)0.0092 (8)0.0017 (7)0.0015 (8)
O80.0135 (8)0.0209 (9)0.0173 (8)0.0008 (7)0.0029 (6)0.0009 (7)
N10.0189 (11)0.0314 (13)0.0182 (10)0.0043 (9)0.0057 (9)0.0001 (9)
N20.0202 (12)0.0327 (13)0.0299 (13)0.0003 (10)0.0084 (9)0.0018 (10)
C10.060 (2)0.043 (2)0.0259 (15)0.0079 (17)0.0065 (15)0.0089 (14)
C20.072 (3)0.045 (2)0.0353 (18)0.017 (2)0.0010 (17)0.0150 (15)
C30.0364 (15)0.0262 (14)0.0215 (12)0.0120 (12)0.0059 (11)0.0002 (10)
C40.0313 (14)0.0242 (13)0.0181 (12)0.0016 (11)0.0064 (10)0.0005 (10)
C50.0243 (13)0.0204 (12)0.0208 (12)0.0012 (10)0.0073 (10)0.0001 (9)
C60.0257 (13)0.0363 (16)0.0198 (12)0.0111 (12)0.0066 (10)0.0002 (11)
C70.0225 (13)0.0327 (15)0.0200 (12)0.0090 (11)0.0038 (10)0.0049 (10)
C80.0318 (16)0.068 (3)0.0276 (15)0.0248 (17)0.0035 (13)0.0087 (15)
C90.044 (2)0.063 (3)0.081 (3)0.023 (2)0.035 (2)0.021 (2)
C100.074 (3)0.053 (3)0.071 (3)0.026 (2)0.049 (3)0.005 (2)
C110.0384 (16)0.0310 (15)0.0298 (14)0.0119 (13)0.0288 (13)0.0072 (12)
C120.0351 (16)0.0225 (14)0.0325 (14)0.0069 (12)0.0168 (12)0.0036 (11)
C130.0294 (14)0.0174 (12)0.0226 (12)0.0029 (10)0.0117 (10)0.0027 (9)
C140.0349 (15)0.0243 (14)0.0246 (13)0.0074 (11)0.0131 (11)0.0071 (11)
C150.0278 (14)0.0260 (14)0.0192 (12)0.0108 (11)0.0049 (10)0.0029 (10)
C160.0389 (17)0.0465 (19)0.0199 (13)0.0188 (14)0.0010 (12)0.0048 (12)
C210.0121 (10)0.0171 (11)0.0216 (11)0.0004 (9)0.0009 (9)0.0032 (9)
C220.0184 (12)0.0211 (12)0.0199 (11)0.0022 (9)0.0023 (9)0.0010 (9)
C230.0161 (11)0.0238 (13)0.0169 (11)0.0020 (9)0.0008 (9)0.0007 (9)
C240.0283 (14)0.0357 (16)0.0202 (12)0.0087 (12)0.0052 (10)0.0045 (11)
C290.0178 (12)0.0251 (13)0.0187 (11)0.0061 (10)0.0071 (9)0.0064 (10)
C300.0196 (12)0.0308 (14)0.0147 (11)0.0054 (10)0.0045 (9)0.0029 (10)
C310.0146 (11)0.0222 (12)0.0166 (11)0.0009 (9)0.0018 (9)0.0034 (9)
C320.0163 (12)0.0425 (17)0.0214 (13)0.0063 (11)0.0006 (10)0.0003 (11)
C330.0207 (13)0.0273 (14)0.0201 (12)0.0035 (10)0.0019 (10)0.0024 (10)
C340.0158 (12)0.0316 (14)0.0217 (12)0.0014 (10)0.0007 (9)0.0029 (10)
C350.0271 (13)0.0303 (14)0.0178 (11)0.0012 (11)0.0003 (10)0.0017 (10)
C360.0181 (12)0.0303 (14)0.0244 (13)0.0025 (11)0.0018 (10)0.0011 (11)
C370.0165 (12)0.0227 (13)0.0204 (12)0.0014 (9)0.0030 (9)0.0012 (10)
C380.0379 (17)0.0353 (17)0.0391 (17)0.0011 (14)0.0202 (14)0.0118 (13)
C390.0142 (13)0.0458 (19)0.0422 (17)0.0004 (13)0.0076 (12)0.0040 (14)
S30.0214 (9)0.0209 (7)0.0198 (7)0.0003 (5)0.0043 (7)0.0022 (5)
C170.014 (7)0.023 (3)0.027 (3)0.001 (3)0.011 (3)0.005 (2)
C180.017 (4)0.017 (4)0.031 (3)0.005 (3)0.003 (3)0.006 (3)
C190.020 (3)0.013 (4)0.025 (4)0.003 (3)0.006 (3)0.003 (2)
C200.0157 (11)0.0171 (12)0.0178 (11)0.0011 (9)0.0022 (9)0.0018 (9)
S40.0205 (7)0.0557 (16)0.0331 (13)0.0192 (9)0.0067 (8)0.0065 (9)
C250.029 (4)0.050 (5)0.019 (5)0.026 (3)0.010 (3)0.010 (4)
C260.039 (4)0.034 (7)0.025 (4)0.009 (4)0.007 (3)0.000 (3)
C270.017 (4)0.045 (6)0.031 (6)0.013 (4)0.003 (3)0.017 (3)
C280.0202 (13)0.032 (4)0.0197 (18)0.0102 (15)0.0070 (12)0.007 (2)
F40.013 (3)0.031 (5)0.031 (3)0.008 (4)0.006 (2)0.005 (3)
F50.030 (8)0.165 (9)0.061 (6)0.020 (4)0.003 (4)0.081 (7)
F60.108 (2)0.084 (2)0.0825 (19)0.0538 (18)0.0709 (19)0.0522 (16)
F100.035 (3)0.086 (7)0.0133 (11)0.030 (5)0.0074 (11)0.016 (2)
F110.019 (3)0.0490 (19)0.019 (3)0.0160 (17)0.0099 (17)0.0033 (16)
F120.0167 (19)0.061 (4)0.060 (3)0.011 (2)0.0093 (17)0.018 (3)
S3'0.0210 (16)0.017 (2)0.027 (2)0.0032 (17)0.0002 (13)0.0028 (13)
C17'0.025 (9)0.027 (12)0.038 (10)0.002 (7)0.019 (7)0.021 (8)
C18'0.007 (10)0.041 (9)0.018 (6)0.006 (5)0.004 (4)0.006 (6)
C19'0.029 (7)0.039 (10)0.058 (15)0.011 (6)0.016 (9)0.030 (9)
C20'0.0157 (11)0.0171 (12)0.0178 (11)0.0011 (9)0.0022 (9)0.0018 (9)
S4'0.018 (2)0.0314 (14)0.0198 (16)0.0093 (14)0.0012 (15)0.0003 (11)
C25'0.030 (8)0.033 (11)0.033 (11)0.010 (7)0.019 (7)0.006 (6)
C26'0.032 (7)0.045 (8)0.017 (8)0.009 (6)0.002 (6)0.012 (7)
C27'0.037 (9)0.009 (5)0.035 (11)0.003 (5)0.009 (6)0.005 (5)
C28'0.0202 (13)0.032 (4)0.0197 (18)0.0102 (15)0.0070 (12)0.007 (2)
F4'0.027 (4)0.051 (9)0.032 (4)0.010 (3)0.003 (3)0.004 (4)
F5'0.030 (8)0.165 (9)0.061 (6)0.020 (4)0.003 (4)0.081 (7)
F6'0.108 (2)0.084 (2)0.0825 (19)0.0538 (18)0.0709 (19)0.0522 (16)
F10A0.035 (3)0.086 (7)0.0133 (11)0.030 (5)0.0074 (11)0.016 (2)
F11A0.019 (3)0.0490 (19)0.019 (3)0.0160 (17)0.0099 (17)0.0033 (16)
F12A0.0167 (19)0.061 (4)0.060 (3)0.011 (2)0.0093 (17)0.018 (3)
F10B0.0349 (5)0.0858 (5)0.0133 (4)0.0300 (6)0.0074 (4)0.0159 (6)
F11B0.019 (3)0.0490 (19)0.019 (3)0.0160 (17)0.0099 (17)0.0033 (16)
F12B0.0167 (19)0.061 (4)0.060 (3)0.011 (2)0.0093 (17)0.018 (3)
F10C0.035 (3)0.086 (7)0.0133 (11)0.030 (5)0.0074 (11)0.016 (2)
F11C0.019 (3)0.0490 (19)0.019 (3)0.0160 (17)0.0099 (17)0.0033 (16)
F12C0.0167 (19)0.061 (4)0.060 (3)0.011 (2)0.0093 (17)0.018 (3)
Geometric parameters (Å, º) top
Eu—O22.3594 (18)C23—C241.537 (3)
Eu—O32.3639 (18)C29—C301.419 (4)
Eu—O82.3642 (17)C29—C281.4700 (19)
Eu—O52.3810 (18)C29—C28'1.470 (2)
Eu—O72.3885 (19)C30—C311.381 (3)
Eu—O12.3935 (18)C30—H300.9500
Eu—O42.4135 (18)C31—C321.537 (3)
Eu—O62.4896 (18)C32—F12B1.327 (3)
S1—C11.703 (4)C32—F11A1.327 (3)
S1—C41.708 (3)C32—F10A1.328 (3)
S2—C91.655 (4)C32—F12C1.330 (3)
S2—C121.704 (4)C32—F101.330 (3)
F1—C81.330 (2)C32—F11B1.330 (3)
F2—C81.327 (2)C32—F10C1.331 (3)
F3—C81.331 (3)C32—F11C1.331 (3)
F7—C241.335 (2)C32—F12A1.333 (3)
F8—C241.335 (2)C32—F121.334 (3)
F9—C241.331 (2)C32—F10B1.334 (3)
O1—C51.250 (3)C32—F111.344 (3)
O2—C71.264 (3)C33—C341.356 (4)
O3—C131.254 (3)C33—C371.419 (4)
O4—C151.265 (3)C33—H330.9500
O5—C211.251 (3)C34—H340.9500
O6—C231.271 (3)C35—C361.360 (4)
O7—C291.258 (3)C35—H350.9500
O8—C311.262 (3)C36—C371.420 (4)
N1—C351.343 (4)C36—H360.9500
N1—C341.348 (4)C38—H38A0.9800
N1—H1N0.87 (4)C38—H38B0.9800
N2—C371.335 (3)C38—H38C0.9800
N2—C381.453 (4)C39—H39A0.9800
N2—C391.462 (4)C39—H39B0.9800
C1—C21.354 (6)C39—H39C0.9800
C1—H10.9500S3—C171.700 (3)
C2—C31.374 (5)S3—C201.703 (2)
C2—H20.9500C17—C181.369 (3)
C3—C41.415 (4)C17—H170.9500
C3—H30.9500C18—C191.429 (3)
C4—C51.460 (4)C18—H180.9500
C5—C61.422 (4)C19—C201.416 (3)
C6—C71.368 (4)C19—H190.9500
C6—H60.9500S4—C251.701 (3)
C7—C81.539 (4)S4—C281.702 (3)
C9—C101.346 (7)C25—C261.369 (3)
C9—H90.9500C25—H250.9500
C10—C111.457 (6)C26—C271.429 (3)
C10—H100.9500C26—H260.9500
C11—C121.507 (4)C27—C281.418 (3)
C11—H110.9500C27—H270.9500
C12—C131.468 (4)S3'—C17'1.699 (3)
C13—C141.407 (4)C17'—C18'1.369 (3)
C14—C151.383 (4)C17'—H17'0.9500
C14—H140.9500C18'—C19'1.430 (3)
C15—C161.539 (4)C18'—H18'0.9500
C16—F4'1.328 (3)C19'—H19'0.9500
C16—F41.329 (3)S4'—C28'1.699 (3)
C16—F51.329 (3)S4'—C25'1.699 (3)
C16—F5'1.329 (3)C25'—C26'1.369 (3)
C16—F6'1.330 (3)C25'—H25'0.9500
C16—F61.330 (3)C26'—C27'1.430 (3)
C21—C221.422 (3)C26'—H26'0.9500
C21—C201.4694 (13)C27'—C28'1.421 (3)
C22—C231.376 (3)C27'—H27'0.9500
C22—H220.9500
O2—Eu—O371.96 (7)F12B—C32—F11A28.5 (10)
O2—Eu—O8146.80 (6)F12B—C32—F10A124.8 (11)
O3—Eu—O8122.74 (6)F11A—C32—F10A106.4 (7)
O2—Eu—O5108.35 (7)F12B—C32—F12C30.2 (13)
O3—Eu—O5153.38 (6)F11A—C32—F12C58.6 (12)
O8—Eu—O572.17 (6)F10A—C32—F12C133.7 (13)
O2—Eu—O789.32 (7)F12B—C32—F10127.5 (9)
O3—Eu—O771.24 (7)F11A—C32—F10119.3 (5)
O8—Eu—O771.04 (6)F10A—C32—F1021.9 (8)
O5—Eu—O7134.78 (6)F12C—C32—F10122.5 (13)
O2—Eu—O171.34 (6)F12B—C32—F11B108.1 (7)
O3—Eu—O1130.78 (7)F11A—C32—F11B84.7 (7)
O8—Eu—O178.07 (6)F10A—C32—F11B24.2 (9)
O5—Eu—O170.77 (7)F12C—C32—F11B128.7 (13)
O7—Eu—O176.67 (7)F10—C32—F11B45.1 (8)
O2—Eu—O4131.75 (6)F12B—C32—F10C122.4 (13)
O3—Eu—O470.25 (7)F11A—C32—F10C131.4 (10)
O8—Eu—O480.37 (6)F10A—C32—F10C51.1 (12)
O5—Eu—O493.22 (7)F12C—C32—F10C103.2 (16)
O7—Eu—O4105.52 (7)F10—C32—F10C29.2 (10)
O1—Eu—O4156.25 (6)F11B—C32—F10C73.8 (12)
O2—Eu—O674.75 (6)F12B—C32—F11C73.6 (12)
O3—Eu—O685.02 (6)F11A—C32—F11C45.8 (8)
O8—Eu—O6131.75 (6)F10A—C32—F11C66.7 (9)
O5—Eu—O669.94 (6)F12C—C32—F11C102.6 (12)
O7—Eu—O6154.71 (6)F10—C32—F11C86.4 (7)
O1—Eu—O6115.04 (7)F11B—C32—F11C42.6 (10)
O4—Eu—O673.15 (6)F10C—C32—F11C113.1 (11)
C1—S1—C491.91 (16)F12B—C32—F12A81.3 (9)
C9—S2—C1292.7 (2)F11A—C32—F12A107.9 (5)
C5—O1—Eu137.88 (18)F10A—C32—F12A105.8 (7)
C7—O2—Eu134.49 (17)F12C—C32—F12A52.4 (13)
C13—O3—Eu140.66 (18)F10—C32—F12A84.6 (7)
C15—O4—Eu132.68 (17)F11B—C32—F12A123.9 (9)
C21—O5—Eu139.92 (15)F10C—C32—F12A56.7 (13)
C23—O6—Eu132.25 (15)F11C—C32—F12A139.7 (8)
C29—O7—Eu136.81 (16)F12B—C32—F1250.8 (10)
C31—O8—Eu132.00 (16)F11A—C32—F1279.2 (5)
C35—N1—C34120.7 (2)F10A—C32—F12132.2 (9)
C35—N1—H1N115 (2)F12C—C32—F1220.7 (11)
C34—N1—H1N124 (2)F10—C32—F12114.1 (5)
C37—N2—C38120.5 (3)F11B—C32—F12138.8 (8)
C37—N2—C39120.4 (2)F10C—C32—F1288.9 (12)
C38—N2—C39119.0 (2)F11C—C32—F12122.5 (7)
C2—C1—S1112.2 (3)F12A—C32—F1233.6 (6)
C2—C1—H1123.9F12B—C32—F10B105.7 (8)
S1—C1—H1123.9F11A—C32—F10B129.0 (9)
C1—C2—C3113.5 (3)F10A—C32—F10B83.4 (9)
C1—C2—H2123.2F12C—C32—F10B78.4 (15)
C3—C2—H2123.2F10—C32—F10B61.4 (11)
C2—C3—C4112.3 (3)F11B—C32—F10B105.4 (8)
C2—C3—H3123.9F10C—C32—F10B32.3 (11)
C4—C3—H3123.9F11C—C32—F10B139.5 (11)
C3—C4—C5130.5 (3)F12A—C32—F10B26.5 (9)
C3—C4—S1110.1 (2)F12—C32—F10B60.2 (11)
C5—C4—S1119.4 (2)F12B—C32—F1153.3 (11)
O1—C5—C6123.8 (2)F11A—C32—F1124.9 (4)
O1—C5—C4117.6 (2)F10A—C32—F1187.4 (7)
C6—C5—C4118.6 (2)F12C—C32—F1183.3 (12)
C7—C6—C5122.0 (2)F10—C32—F11105.4 (4)
C7—C6—H6119.0F11B—C32—F1163.7 (8)
C5—C6—H6119.0F10C—C32—F11128.3 (10)
O2—C7—C6128.8 (3)F11C—C32—F1121.8 (6)
O2—C7—C8112.5 (2)F12A—C32—F11129.8 (5)
C6—C7—C8118.7 (2)F12—C32—F11103.9 (4)
F2—C8—F1106.7 (2)F10B—C32—F11143.9 (8)
F2—C8—F3107.5 (3)C34—C33—C37120.2 (2)
F1—C8—F3106.3 (3)C34—C33—H33119.9
F2—C8—C7113.8 (2)C37—C33—H33119.9
F1—C8—C7110.9 (2)N1—C34—C33121.1 (2)
F3—C8—C7111.3 (2)N1—C34—H34119.5
C10—C9—S2113.7 (3)C33—C34—H34119.5
C10—C9—H9123.2N1—C35—C36121.5 (3)
S2—C9—H9123.2N1—C35—H35119.2
C9—C10—C11117.0 (3)C36—C35—H35119.2
C9—C10—H10121.5C35—C36—C37119.8 (3)
C11—C10—H10121.5C35—C36—H36120.1
C10—C11—C12103.4 (3)C37—C36—H36120.1
C10—C11—H11128.3N2—C37—C33121.8 (2)
C12—C11—H11128.3N2—C37—C36121.5 (3)
C13—C12—C11128.6 (3)C33—C37—C36116.7 (2)
C13—C12—S2118.3 (2)N2—C38—H38A109.5
C11—C12—S2113.1 (2)N2—C38—H38B109.5
O3—C13—C14123.2 (2)H38A—C38—H38B109.5
O3—C13—C12116.0 (3)N2—C38—H38C109.5
C14—C13—C12120.7 (2)H38A—C38—H38C109.5
C15—C14—C13121.6 (3)H38B—C38—H38C109.5
C15—C14—H14119.2N2—C39—H39A109.5
C13—C14—H14119.2N2—C39—H39B109.5
O4—C15—C14129.0 (3)H39A—C39—H39B109.5
O4—C15—C16113.4 (2)N2—C39—H39C109.5
C14—C15—C16117.5 (2)H39A—C39—H39C109.5
F4'—C16—F411.6 (19)H39B—C39—H39C109.5
F4'—C16—F5110 (2)C17—S3—C2093.2 (4)
F4—C16—F5105 (2)C18—C17—S3111.6 (7)
F4'—C16—F5'110 (2)C18—C17—H17124.2
F4—C16—F5'101 (2)S3—C17—H17124.2
F5—C16—F5'18.4 (18)C17—C18—C19113.2 (9)
F4'—C16—F6'98 (8)C17—C18—H18123.4
F4—C16—F6'109 (8)C19—C18—H18123.4
F5—C16—F6'98 (9)C20—C19—C18110.6 (7)
F5'—C16—F6'116 (9)C20—C19—H19124.7
F4'—C16—F698 (8)C18—C19—H19124.7
F4—C16—F6109 (8)C19—C20—C21128.6 (5)
F5—C16—F698 (9)C19—C20—S3111.0 (5)
F5'—C16—F6116 (9)C21—C20—S3120.33 (18)
F6'—C16—F60 (10)C25—S4—C2889.6 (5)
F4'—C16—C15114.6 (9)C26—C25—S4118.8 (11)
F4—C16—C15111.1 (8)C26—C25—H25120.6
F5—C16—C15121.2 (11)S4—C25—H25120.6
F5'—C16—C15107.8 (10)C25—C26—C27104.8 (13)
F6'—C16—C15111 (7)C25—C26—H26127.6
F6—C16—C15111 (7)C27—C26—H26127.6
O5—C21—C22123.66 (19)C28—C27—C26115.5 (10)
O5—C21—C20117.0 (2)C28—C27—H27122.2
C22—C21—C20119.3 (2)C26—C27—H27122.2
C23—C22—C21122.3 (2)C27—C28—C29131.7 (6)
C23—C22—H22118.9C27—C28—S4110.4 (5)
C21—C22—H22118.9C29—C28—S4117.8 (3)
O6—C23—C22129.5 (2)C18'—C17'—S3'110.3 (15)
O6—C23—C24113.7 (2)C18'—C17'—H17'124.9
C22—C23—C24116.8 (2)S3'—C17'—H17'124.9
F9—C24—F7107.9 (2)C17'—C18'—C19'115 (2)
F9—C24—F8106.9 (2)C17'—C18'—H18'122.4
F7—C24—F8106.9 (2)C19'—C18'—H18'122.4
F9—C24—C23113.80 (19)C18'—C19'—H19'127.2
F7—C24—C23110.72 (19)C28'—S4'—C25'85.9 (10)
F8—C24—C23110.3 (2)C26'—C25'—S4'123 (2)
O7—C29—C30123.9 (2)C26'—C25'—H25'118.6
O7—C29—C28116.9 (5)S4'—C25'—H25'118.6
C30—C29—C28119.2 (5)C25'—C26'—C27'101 (2)
O7—C29—C28'117.2 (10)C25'—C26'—H26'129.7
C30—C29—C28'118.9 (10)C27'—C26'—H26'129.7
C28—C29—C28'3 (6)C28'—C27'—C26'116 (2)
C31—C30—C29121.6 (2)C28'—C27'—H27'122.1
C31—C30—H30119.2C26'—C27'—H27'122.1
C29—C30—H30119.2C27'—C28'—C29125.5 (12)
O8—C31—C30128.5 (2)C27'—C28'—S4'112.1 (13)
O8—C31—C32113.6 (2)C29—C28'—S4'121.9 (4)
C30—C31—C32117.8 (2)
O2—Eu—O1—C51.7 (3)S2—C12—C13—C14178.4 (2)
O3—Eu—O1—C542.0 (3)O3—C13—C14—C150.4 (4)
O8—Eu—O1—C5165.2 (3)C12—C13—C14—C15177.9 (3)
O5—Eu—O1—C5119.8 (3)Eu—O4—C15—C1421.0 (5)
O7—Eu—O1—C592.1 (3)Eu—O4—C15—C16155.28 (17)
O4—Eu—O1—C5169.6 (2)C13—C14—C15—O48.0 (5)
O6—Eu—O1—C564.1 (3)C13—C14—C15—C16168.1 (2)
O3—Eu—O2—C7133.8 (3)O4—C15—C16—F4'45.6 (11)
O8—Eu—O2—C711.0 (3)C14—C15—C16—F4'137.7 (11)
O5—Eu—O2—C774.3 (3)O4—C15—C16—F457.6 (10)
O7—Eu—O2—C763.3 (3)C14—C15—C16—F4125.7 (11)
O1—Eu—O2—C712.8 (3)O4—C15—C16—F5178 (2)
O4—Eu—O2—C7173.7 (2)C14—C15—C16—F52 (2)
O6—Eu—O2—C7136.5 (3)O4—C15—C16—F5'167.9 (18)
O2—Eu—O3—C13138.9 (3)C14—C15—C16—F5'15.4 (18)
O8—Eu—O3—C1374.3 (3)O4—C15—C16—F6'64 (9)
O5—Eu—O3—C1343.8 (4)C14—C15—C16—F6'113 (9)
O7—Eu—O3—C13125.5 (3)O4—C15—C16—F664 (9)
O1—Eu—O3—C13177.6 (3)C14—C15—C16—F6113 (9)
O4—Eu—O3—C1310.5 (3)Eu—O5—C21—C2218.8 (4)
O6—Eu—O3—C1363.4 (3)Eu—O5—C21—C20161.13 (18)
O2—Eu—O4—C1523.4 (3)O5—C21—C22—C232.3 (4)
O3—Eu—O4—C1517.0 (2)C20—C21—C22—C23177.6 (2)
O8—Eu—O4—C15147.1 (3)Eu—O6—C23—C224.7 (4)
O5—Eu—O4—C15141.6 (2)Eu—O6—C23—C24175.31 (14)
O7—Eu—O4—C1580.0 (3)C21—C22—C23—O63.5 (4)
O1—Eu—O4—C15172.1 (2)C21—C22—C23—C24176.5 (2)
O6—Eu—O4—C1573.7 (2)O6—C23—C24—F9172.8 (2)
O2—Eu—O5—C2146.7 (3)C22—C23—C24—F97.1 (3)
O3—Eu—O5—C2139.5 (3)O6—C23—C24—F765.4 (3)
O8—Eu—O5—C21168.2 (3)C22—C23—C24—F7114.6 (2)
O7—Eu—O5—C21154.9 (2)O6—C23—C24—F852.7 (3)
O1—Eu—O5—C21108.5 (3)C22—C23—C24—F8127.3 (2)
O4—Eu—O5—C2189.4 (3)Eu—O7—C29—C306.9 (4)
O6—Eu—O5—C2118.7 (3)Eu—O7—C29—C28174 (2)
O2—Eu—O6—C23106.0 (2)Eu—O7—C29—C28'171 (4)
O3—Eu—O6—C23178.7 (2)O7—C29—C30—C317.3 (4)
O8—Eu—O6—C2350.8 (2)C28—C29—C30—C31172 (2)
O5—Eu—O6—C2310.5 (2)C28'—C29—C30—C31175 (4)
O7—Eu—O6—C23158.7 (2)Eu—O8—C31—C3027.7 (4)
O1—Eu—O6—C2345.6 (2)Eu—O8—C31—C32154.24 (15)
O4—Eu—O6—C23110.5 (2)C29—C30—C31—O83.4 (4)
O2—Eu—O7—C29134.9 (3)C29—C30—C31—C32178.7 (2)
O3—Eu—O7—C29154.0 (3)C35—N1—C34—C330.2 (4)
O8—Eu—O7—C2917.8 (2)C37—C33—C34—N10.8 (4)
O5—Eu—O7—C2919.3 (3)C34—N1—C35—C360.6 (4)
O1—Eu—O7—C2963.9 (3)N1—C35—C36—C370.6 (4)
O4—Eu—O7—C2991.7 (3)C38—N2—C37—C331.6 (4)
O6—Eu—O7—C29175.0 (2)C39—N2—C37—C33179.2 (3)
O2—Eu—O8—C3129.9 (3)C38—N2—C37—C36178.3 (3)
O3—Eu—O8—C3178.2 (2)C39—N2—C37—C360.7 (4)
O5—Eu—O8—C31126.3 (2)C34—C33—C37—N2179.3 (3)
O7—Eu—O8—C3126.9 (2)C34—C33—C37—C360.8 (4)
O1—Eu—O8—C3152.9 (2)C35—C36—C37—N2180.0 (3)
O4—Eu—O8—C31137.1 (2)C35—C36—C37—C330.1 (4)
O6—Eu—O8—C31165.9 (2)C20—S3—C17—C184.1 (15)
C4—S1—C1—C20.2 (3)S3—C17—C18—C197 (2)
S1—C1—C2—C30.3 (5)C17—C18—C19—C207 (2)
C1—C2—C3—C40.2 (5)C18—C19—C20—C21176.0 (9)
C2—C3—C4—C5177.2 (3)C18—C19—C20—S33.8 (15)
C2—C3—C4—S10.0 (4)O5—C21—C20—C19174.5 (10)
C1—S1—C4—C30.1 (2)C22—C21—C20—C195.6 (10)
C1—S1—C4—C5177.4 (2)O5—C21—C20—S35.7 (3)
Eu—O1—C5—C66.7 (4)C22—C21—C20—S3174.2 (2)
Eu—O1—C5—C4174.05 (19)C17—S3—C20—C190.1 (11)
C3—C4—C5—O1177.2 (3)C17—S3—C20—C21179.9 (7)
S1—C4—C5—O10.3 (3)C28—S4—C25—C267 (2)
C3—C4—C5—C63.4 (4)S4—C25—C26—C2710 (2)
S1—C4—C5—C6179.6 (2)C25—C26—C27—C289 (3)
O1—C5—C6—C78.3 (5)C26—C27—C28—C29178 (4)
C4—C5—C6—C7172.4 (3)C26—C27—C28—S44 (4)
Eu—O2—C7—C616.2 (5)O7—C29—C28—C27171 (4)
Eu—O2—C7—C8161.58 (18)C30—C29—C28—C278 (6)
C5—C6—C7—O22.8 (5)C28'—C29—C28—C2792 (22)
C5—C6—C7—C8174.8 (3)O7—C29—C28—S411 (4)
O2—C7—C8—F2171.5 (3)C30—C29—C28—S4170 (2)
C6—C7—C8—F210.5 (4)C28'—C29—C28—S486 (15)
O2—C7—C8—F151.2 (3)C25—S4—C28—C271 (3)
C6—C7—C8—F1130.8 (3)C25—S4—C28—C29177 (3)
O2—C7—C8—F366.9 (3)S3'—C17'—C18'—C19'18 (4)
C6—C7—C8—F3111.1 (3)C28'—S4'—C25'—C26'16 (5)
C12—S2—C9—C100.8 (4)S4'—C25'—C26'—C27'18 (4)
S2—C9—C10—C111.2 (5)C25'—C26'—C27'—C28'10 (6)
C9—C10—C11—C122.7 (5)C26'—C27'—C28'—C29171 (6)
C10—C11—C12—C13176.1 (3)C26'—C27'—C28'—S4'0 (8)
C10—C11—C12—S23.2 (3)O7—C29—C28'—C27'5 (10)
C9—S2—C12—C13177.0 (3)C30—C29—C28'—C27'173 (6)
C9—S2—C12—C112.5 (3)C28—C29—C28'—C27'89 (24)
Eu—O3—C13—C145.4 (4)O7—C29—C28'—S4'166 (5)
Eu—O3—C13—C12172.08 (19)C30—C29—C28'—S4'16 (9)
C11—C12—C13—O3178.5 (3)C28—C29—C28'—S4'81 (12)
S2—C12—C13—O30.8 (3)C25'—S4'—C28'—C27'8 (6)
C11—C12—C13—C140.9 (4)C25'—S4'—C28'—C29179 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O6i0.87 (4)1.96 (4)2.814 (3)168 (4)
Symmetry code: (i) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formula(C7H11N2)[Eu(C8H4F3O2S)4]
Mr1159.83
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)93
a, b, c (Å)20.0202 (4), 18.9160 (3), 23.4108 (4)
V3)8865.7 (3)
Z8
Radiation typeMo Kα
µ (mm1)1.71
Crystal size (mm)0.62 × 0.45 × 0.23
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionNumerical
(ABSCOR; Higashi, 1999)
Tmin, Tmax0.418, 0.695
No. of measured, independent and
observed [I > 2σ(I)] reflections
82834, 10137, 9604
Rint0.048
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.085, 1.00
No. of reflections10137
No. of parameters725
No. of restraints76
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0426P)2 + 19.8P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.29, 1.10

Computer programs: RAPID-AUTO (Rigaku, 2006), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O6i0.87 (4)1.96 (4)2.814 (3)168 (4)
Symmetry code: (i) x, y+3/2, z1/2.
 

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