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Acta Cryst. (2007). E63, m2566    [ doi:10.1107/S1600536807045667 ]

4-Dimethylaminopyridinium tetrakis[3,3,3-trifluoro-1-(2-thienylcarbonyl)prop-1-en-2-olato]europate(III)

X.-C. Wei, Y.-K. Bian, K.-B. Yu and D.-Y. He

Abstract top

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 [beta]-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.

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 0.78Å from the Eu atom, and the deepest hole is 0.62 Å from the S2 atom.

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 m−3
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 = 3.0–27.5º
b = 18.9160 (3) ŵ = 1.71 mm−1
c = 23.4108 (4) ÅT = 93 (2) K
V = 8865.7 (3) Å3Block, light yellow
Z = 80.62 × 0.45 × 0.23 mm
F000 = 4592
Data collection top
Rigaku R-AXIS RAPID
diffractometer		10137 independent reflections
Radiation source: Rotating Anode9604 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
T = 93(2) Kθmax = 27.5º
ω scansθmin = 3.0º
Absorption correction: numerical
(ABSCOR; Higashi, 1999)		h = −25→21
Tmin = 0.418, Tmax = 0.695k = −24→24
82834 measured reflectionsl = −30→30
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 Å−3
725 parametersΔρmin = −1.10 e Å−3
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
a = 20.0202 (4) ŵ = 1.71 mm−1
b = 18.9160 (3) ÅT = 93 (2) 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 Å−3
725 parametersΔρmin = −1.10 e Å−3
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 > 2sigma(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)
H350.46280.8338−0.00860.030*
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, °) 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—C14−178.4 (2)
O3—Eu—O1—C5−42.0 (3)O3—C13—C14—C150.4 (4)
O8—Eu—O1—C5−165.2 (3)C12—C13—C14—C15177.9 (3)
O5—Eu—O1—C5119.8 (3)Eu—O4—C15—C14−21.0 (5)
O7—Eu—O1—C5−92.1 (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—C16−168.1 (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—C7−74.3 (3)O4—C15—C16—F457.6 (10)
O7—Eu—O2—C763.3 (3)C14—C15—C16—F4−125.7 (11)
O1—Eu—O2—C7−12.8 (3)O4—C15—C16—F5−178 (2)
O4—Eu—O2—C7173.7 (2)C14—C15—C16—F5−2(2)
O6—Eu—O2—C7−136.5 (3)O4—C15—C16—F5'167.9 (18)
O2—Eu—O3—C13138.9 (3)C14—C15—C16—F5'−15.4 (18)
O8—Eu—O3—C13−74.3 (3)O4—C15—C16—F6'−64 (9)
O5—Eu—O3—C1343.8 (4)C14—C15—C16—F6'113 (9)
O7—Eu—O3—C13−125.5 (3)O4—C15—C16—F6−64 (9)
O1—Eu—O3—C13−177.6 (3)C14—C15—C16—F6113 (9)
O4—Eu—O3—C13−10.5 (3)Eu—O5—C21—C22−18.8 (4)
O6—Eu—O3—C1363.4 (3)Eu—O5—C21—C20161.13 (18)
O2—Eu—O4—C15−23.4 (3)O5—C21—C22—C232.3 (4)
O3—Eu—O4—C1517.0 (2)C20—C21—C22—C23−177.6 (2)
O8—Eu—O4—C15147.1 (3)Eu—O6—C23—C224.7 (4)
O5—Eu—O4—C15−141.6 (2)Eu—O6—C23—C24−175.31 (14)
O7—Eu—O4—C1580.0 (3)C21—C22—C23—O63.5 (4)
O1—Eu—O4—C15172.1 (2)C21—C22—C23—C24−176.5 (2)
O6—Eu—O4—C15−73.7 (2)O6—C23—C24—F9−172.8 (2)
O2—Eu—O5—C21−46.7 (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—F7−114.6 (2)
O7—Eu—O5—C21−154.9 (2)O6—C23—C24—F8−52.7 (3)
O1—Eu—O5—C21−108.5 (3)C22—C23—C24—F8127.3 (2)
O4—Eu—O5—C2189.4 (3)Eu—O7—C29—C30−6.9 (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—C31−7.3 (4)
O8—Eu—O6—C23−50.8 (2)C28—C29—C30—C31172 (2)
O5—Eu—O6—C23−10.5 (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—C32−154.24 (15)
O4—Eu—O6—C23−110.5 (2)C29—C30—C31—O8−3.4 (4)
O2—Eu—O7—C29−134.9 (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—N1−0.8 (4)
O5—Eu—O7—C29−19.3 (3)C34—N1—C35—C360.6 (4)
O1—Eu—O7—C29−63.9 (3)N1—C35—C36—C37−0.6 (4)
O4—Eu—O7—C2991.7 (3)C38—N2—C37—C33−1.6 (4)
O6—Eu—O7—C29175.0 (2)C39—N2—C37—C33−179.2 (3)
O2—Eu—O8—C3129.9 (3)C38—N2—C37—C36178.3 (3)
O3—Eu—O8—C31−78.2 (2)C39—N2—C37—C360.7 (4)
O5—Eu—O8—C31126.3 (2)C34—C33—C37—N2−179.3 (3)
O7—Eu—O8—C31−26.9 (2)C34—C33—C37—C360.8 (4)
O1—Eu—O8—C3152.9 (2)C35—C36—C37—N2−180.0 (3)
O4—Eu—O8—C31−137.1 (2)C35—C36—C37—C33−0.1 (4)
O6—Eu—O8—C31165.9 (2)C20—S3—C17—C184.1 (15)
C4—S1—C1—C20.2 (3)S3—C17—C18—C19−7(2)
S1—C1—C2—C3−0.3 (5)C17—C18—C19—C207(2)
C1—C2—C3—C40.2 (5)C18—C19—C20—C21176.0 (9)
C2—C3—C4—C5−177.2 (3)C18—C19—C20—S3−3.8 (15)
C2—C3—C4—S10.0 (4)O5—C21—C20—C19174.5 (10)
C1—S1—C4—C3−0.1 (2)C22—C21—C20—C19−5.6 (10)
C1—S1—C4—C5177.4 (2)O5—C21—C20—S3−5.7 (3)
Eu—O1—C5—C66.7 (4)C22—C21—C20—S3174.2 (2)
Eu—O1—C5—C4−174.05 (19)C17—S3—C20—C19−0.1 (11)
C3—C4—C5—O1177.2 (3)C17—S3—C20—C21−179.9 (7)
S1—C4—C5—O10.3 (3)C28—S4—C25—C26−7(2)
C3—C4—C5—C6−3.4 (4)S4—C25—C26—C2710 (2)
S1—C4—C5—C6179.6 (2)C25—C26—C27—C28−9(3)
O1—C5—C6—C7−8.3 (5)C26—C27—C28—C29−178 (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—C8−161.58 (18)C30—C29—C28—C27−8(6)
C5—C6—C7—O2−2.8 (5)C28'—C29—C28—C27−92 (22)
C5—C6—C7—C8174.8 (3)O7—C29—C28—S4−11 (4)
O2—C7—C8—F2−171.5 (3)C30—C29—C28—S4170 (2)
C6—C7—C8—F210.5 (4)C28'—C29—C28—S486 (15)
O2—C7—C8—F1−51.2 (3)C25—S4—C28—C271(3)
C6—C7—C8—F1130.8 (3)C25—S4—C28—C29−177 (3)
O2—C7—C8—F366.9 (3)S3'—C17'—C18'—C19'18 (4)
C6—C7—C8—F3−111.1 (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—C12−2.7 (5)C26'—C27'—C28'—C29171 (6)
C10—C11—C12—C13−176.1 (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—C11−2.5 (3)C28—C29—C28'—C27'−89 (24)
Eu—O3—C13—C145.4 (4)O7—C29—C28'—S4'166 (5)
Eu—O3—C13—C12−172.08 (19)C30—C29—C28'—S4'−16 (9)
C11—C12—C13—O3178.5 (3)C28—C29—C28'—S4'81 (12)
S2—C12—C13—O3−0.8 (3)C25'—S4'—C28'—C27'−8(6)
C11—C12—C13—C140.9 (4)C25'—S4'—C28'—C29−179 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O6i0.87 (4)1.96 (4)2.814 (3)168 (4)
Symmetry codes: (i) x, −y+3/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O6i0.87 (4)1.96 (4)2.814 (3)168 (4)
Symmetry codes: (i) x, −y+3/2, z−1/2.
Acknowledgements top

This work was supported by the Interdisciplinary Innovation Research Fund for Young Scholars, Lanzhou University, China (grant No. LZU824606), and the Research Award Fund for Outstanding Young Teachers in Higher Education Institutions, China (grant No. 2002363).

references
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