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RETRACTED ARTICLE

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Tetra­kis(μ-2,4-di­fluoro­benzoato)bis­­[(2,2′-bi­pyridine)(2,4-di­fluoro­benzoato)terbium(III)]

aCollege of Food and Biological Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China, and bMaize Research Institute, Shandong Academy of Agricultural Science, Jinan 250100, People's Republic of China
*Correspondence e-mail: lujianghao001@yahoo.com.cn

(Received 29 September 2008; accepted 25 December 2008; online 8 January 2009)

In the centrosymmetric dinuclear title compound, [Tb2(C7H3F2O2)6(C10H8N2)2], the TbIII ion is coordinated by an N,N′-bidentate 2,2′-bipyridine mol­ecule, and two O,O′-bidentate 2,4-difluoro­benzoate (dfb) anions. One of the latter also bonds to the second TbIII centre through one of its O atoms. The third dfb anion bonds to one Tb atom from each of its O atoms. Thus, the three dfb species have three different coordination modes. This results in an irregular TbN2O7 coordination sphere for the metal ion. The F atoms and their associated H atoms in the simple bidentate dfb anion are disordered over two sets of sites in a 0.672 (10):0.328 (10) ratio.

Related literature

For related literature on the biological applications of carboxyl­ates as ligands, see, for example: Serre et al. (2005[Serre, C., Marrot, J. & Ferey, G. (2005). Inorg. Chem. 44, 654-658.]).

[Scheme 1]

Experimental

Crystal data
  • [Tb2(C7H3F2O2)6(C10H8N2)2]

  • Mr = 1572.77

  • Triclinic, [P \overline 1]

  • a = 11.401 (1) Å

  • b = 12.189 (1) Å

  • c = 12.588 (2) Å

  • α = 103.99 (2)°

  • β = 102.90 (2)°

  • γ = 113.58 (2)°

  • V = 1451.5 (3) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 2.52 mm−1

  • T = 293 (2) K

  • 0.44 × 0.26 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.403, Tmax = 0.632

  • 8233 measured reflections

  • 5557 independent reflections

  • 4813 reflections with I > 2σ(I)

  • Rint = 0.0210

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.078

  • S = 1.03

  • 5557 reflections

  • 434 parameters

  • H-atom parameters constrained

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.57 e Å−3

Table 1
Selected bond lengths (Å)

Tb1—N1 2.565 (3)
Tb1—N2 2.586 (4)
Tb1—O6i 2.364 (3)
Tb1—O3i 2.377 (3)
Tb1—O5 2.379 (3)
Tb1—O2 2.418 (3)
Tb1—O4 2.481 (3)
Tb1—O1 2.498 (3)
Tb1—O3 2.696 (3)
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In recent years, carboxylic acids have been widely used as polydentate ligands, which can coordinate to transition or rare earth ions yielding complexes with interesting biological properties (e.g. Serre et al., 2005). Herein, we report the synthesis and X-ray crystal structure analysis of the centrosymetric title compound, (I), Fig. 1.

The TbIII is chelated by two 2,4-difluorobezoate anions and one 4,4'-bipyridine molecule. Two cations are linked into dimer via three bridging carboxylate groups from three 2,4-difluorobezoic acid. As a result, the TbIII ion is nine-coordinated with seven O atoms and two N atoms (Table 1).

Related literature top

For related literature on the biological applications of carboxylates as ligands, see, for example: Serre et al. (2005).

Experimental top

A mixture of terbium(III) chloride (0.5 mmol), 2,4-difluorobezoic acid (1 mmol), sodium hydroxide (1 mmol), 4,4'-bipyridine (0.5 mmol), H2O (8 ml) and ethanol (8 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 433 K for three days. Colourless blocks of (I) were obtained after cooling to room temperature with a yield of 16%. Anal. Calc. for C62H34F12Tb2N4O12: C 47.41, H 2.17, N 3.57%; Found: C 47.38, H 2.19, N 3.55%.

Refinement top

The H atoms were placed in calculated positions (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The F atoms of the bidenate dfb anion are disordered over two sets of sites in a 0.672 (10):0.328 (10) ratio.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing 30% probability displacement ellipsoids. Symmetry code: (i) –x +1, –y + 2, –z + 1.
Tetrakis(µ-2,4-difluorobenzoato)bis[(2,2'-bipyridine)(2,4- difluorobenzoato)terbium(III)] top
Crystal data top
[Tb2(C7H3F2O2)6(C10H8N2)2]Z = 1
Mr = 1572.77F(000) = 768
Triclinic, P1Dx = 1.799 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.401 (1) ÅCell parameters from 5557 reflections
b = 12.189 (1) Åθ = 1.8–26.0°
c = 12.588 (2) ŵ = 2.52 mm1
α = 103.99 (2)°T = 293 K
β = 102.90 (2)°Block, colorless
γ = 113.58 (2)°0.44 × 0.26 × 0.20 mm
V = 1451.5 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer
5557 independent reflections
Radiation source: fine-focus sealed tube4813 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ϕ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1413
Tmin = 0.403, Tmax = 0.632k = 1514
8233 measured reflectionsl = 015
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0345P)2 + 0.822P]
where P = (Fo2 + 2Fc2)/3
5557 reflections(Δ/σ)max = 0.001
434 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.57 e Å3
Crystal data top
[Tb2(C7H3F2O2)6(C10H8N2)2]γ = 113.58 (2)°
Mr = 1572.77V = 1451.5 (3) Å3
Triclinic, P1Z = 1
a = 11.401 (1) ÅMo Kα radiation
b = 12.189 (1) ŵ = 2.52 mm1
c = 12.588 (2) ÅT = 293 K
α = 103.99 (2)°0.44 × 0.26 × 0.20 mm
β = 102.90 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
5557 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
4813 reflections with I > 2σ(I)
Tmin = 0.403, Tmax = 0.632Rint = 0.021
8233 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.078H-atom parameters constrained
S = 1.03Δρmax = 0.60 e Å3
5557 reflectionsΔρmin = 0.57 e Å3
434 parameters
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)
Tb10.39615 (2)0.804496 (17)0.439773 (18)0.03337 (8)
F10.8156 (4)1.1600 (3)0.2648 (3)0.0809 (11)
F20.3952 (4)0.7245 (4)0.0812 (3)0.1009 (13)
F30.7957 (4)0.9340 (4)0.8322 (3)0.0947 (13)
F41.1389 (4)1.1727 (5)0.6340 (6)0.136 (2)
F50.1318 (6)0.5659 (8)0.2091 (5)0.131 (3)0.672 (10)
F60.0100 (8)0.6768 (9)0.1480 (6)0.155 (4)0.672 (10)
F70.1797 (11)0.7301 (13)0.0303 (10)0.100 (5)0.328 (10)
F80.3317 (10)0.5145 (17)0.0353 (11)0.126 (7)0.328 (10)
O10.1421 (3)0.6937 (3)0.3366 (3)0.0459 (8)
O20.2722 (3)0.7141 (3)0.2304 (3)0.0497 (8)
O30.6259 (3)1.0197 (2)0.5936 (3)0.0361 (7)
O40.5990 (3)0.8317 (3)0.5898 (3)0.0492 (9)
O50.5614 (3)0.8920 (3)0.3552 (3)0.0392 (7)
O60.6504 (3)1.1034 (3)0.3975 (3)0.0449 (8)
N10.2901 (4)0.6091 (3)0.4973 (4)0.0459 (10)
N20.4379 (4)0.6128 (3)0.3584 (3)0.0431 (9)
C10.5204 (5)0.6201 (5)0.2990 (5)0.0539 (13)
H10.56130.69550.28500.065*
C20.5503 (7)0.5218 (6)0.2559 (5)0.0681 (17)
H20.60970.53110.21460.082*
C30.4902 (7)0.4132 (5)0.2760 (5)0.0704 (18)
H30.50760.34550.24860.085*
C40.4042 (7)0.4023 (5)0.3364 (5)0.0638 (17)
H40.36260.32700.35040.077*
C50.3780 (5)0.5031 (4)0.3773 (4)0.0446 (12)
C60.6742 (4)0.9489 (4)0.6192 (4)0.0345 (9)
C70.8260 (4)1.0066 (4)0.6802 (4)0.0385 (10)
C80.9148 (5)1.0685 (5)0.6301 (5)0.0592 (14)
H80.88201.07860.56050.071*
C91.0537 (6)1.1153 (6)0.6853 (7)0.0772 (19)
C101.1062 (6)1.1066 (6)0.7881 (8)0.086 (2)
H101.20051.14170.82420.103*
C111.0191 (6)1.0454 (7)0.8389 (6)0.0792 (19)
H111.05321.03790.90950.095*
C120.8806 (5)0.9955 (5)0.7837 (5)0.0525 (13)
C130.1575 (5)0.6867 (4)0.2397 (4)0.0385 (10)
C140.0384 (5)0.6523 (4)0.1333 (4)0.0400 (10)
C150.0962 (5)0.5956 (6)0.1252 (5)0.0591 (14)
H150.11660.57540.18770.071*0.328 (10)
C160.2018 (6)0.5664 (7)0.0283 (6)0.0759 (18)
H160.29130.52740.02670.091*0.672 (10)
C170.1771 (6)0.5947 (6)0.0640 (5)0.0720 (18)
H170.24840.57710.12980.086*
C180.0453 (7)0.6497 (6)0.0581 (5)0.0716 (17)
H180.02630.66840.12160.086*0.328 (10)
C190.0606 (6)0.6780 (5)0.0380 (5)0.0569 (14)
H190.14950.71600.03810.068*0.672 (10)
C200.6086 (4)0.9903 (4)0.3307 (4)0.0363 (10)
C210.6107 (5)0.9677 (4)0.2092 (4)0.0418 (11)
C220.7081 (6)1.0524 (5)0.1800 (5)0.0531 (13)
C230.7024 (7)1.0276 (6)0.0660 (6)0.0652 (16)
H230.77091.08590.04890.078*
C240.5965 (7)0.9176 (6)0.0230 (5)0.0681 (16)
H240.59030.90120.10070.082*
C250.5015 (6)0.8340 (6)0.0064 (5)0.0636 (15)
C260.5055 (5)0.8547 (5)0.1189 (4)0.0491 (12)
H260.43850.79390.13520.059*
C270.2154 (5)0.6091 (5)0.5643 (6)0.0599 (15)
H270.21910.68670.60220.072*
C280.1331 (6)0.5017 (6)0.5811 (6)0.0762 (19)
H280.08300.50660.62940.091*
C290.1267 (7)0.3900 (6)0.5266 (7)0.087 (2)
H290.07050.31540.53550.105*
C300.2036 (7)0.3854 (5)0.4570 (6)0.080 (2)
H300.19970.30770.41890.095*
C310.2873 (5)0.4976 (4)0.4440 (4)0.0496 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Tb10.03168 (12)0.02483 (11)0.04084 (14)0.01158 (9)0.00750 (9)0.01636 (9)
F10.075 (2)0.059 (2)0.086 (2)0.0040 (17)0.046 (2)0.0247 (18)
F20.109 (3)0.095 (3)0.055 (2)0.024 (2)0.030 (2)0.000 (2)
F30.070 (2)0.161 (4)0.069 (2)0.053 (2)0.0260 (19)0.071 (3)
F40.070 (3)0.148 (4)0.246 (6)0.052 (3)0.088 (3)0.135 (4)
F50.054 (4)0.219 (8)0.078 (4)0.016 (4)0.019 (3)0.078 (5)
F60.113 (6)0.211 (9)0.079 (5)0.015 (5)0.008 (4)0.089 (5)
F70.051 (7)0.170 (13)0.094 (9)0.037 (7)0.027 (6)0.104 (9)
F80.032 (6)0.229 (17)0.083 (9)0.030 (8)0.006 (5)0.073 (10)
O10.0388 (18)0.0500 (19)0.0408 (19)0.0129 (15)0.0084 (14)0.0241 (15)
O20.0381 (19)0.057 (2)0.0442 (19)0.0216 (16)0.0075 (15)0.0124 (16)
O30.0339 (16)0.0284 (14)0.0453 (18)0.0156 (12)0.0066 (13)0.0184 (13)
O40.0407 (18)0.0239 (15)0.064 (2)0.0096 (13)0.0056 (16)0.0193 (15)
O50.0390 (17)0.0323 (16)0.0500 (19)0.0158 (13)0.0196 (14)0.0202 (14)
O60.0522 (19)0.0304 (16)0.051 (2)0.0140 (14)0.0240 (16)0.0179 (15)
N10.037 (2)0.035 (2)0.062 (3)0.0114 (17)0.0091 (19)0.0296 (19)
N20.042 (2)0.0300 (19)0.051 (2)0.0176 (17)0.0046 (19)0.0161 (17)
C10.052 (3)0.043 (3)0.063 (3)0.025 (2)0.017 (3)0.015 (2)
C20.077 (4)0.068 (4)0.058 (4)0.051 (3)0.011 (3)0.006 (3)
C30.094 (5)0.045 (3)0.061 (4)0.048 (3)0.002 (3)0.002 (3)
C40.084 (4)0.033 (3)0.052 (3)0.030 (3)0.008 (3)0.006 (2)
C50.052 (3)0.027 (2)0.038 (3)0.020 (2)0.011 (2)0.0080 (19)
C60.033 (2)0.033 (2)0.034 (2)0.0145 (18)0.0048 (18)0.0158 (18)
C70.034 (2)0.032 (2)0.048 (3)0.0206 (19)0.007 (2)0.013 (2)
C80.050 (3)0.054 (3)0.084 (4)0.026 (3)0.025 (3)0.041 (3)
C90.046 (3)0.066 (4)0.132 (6)0.026 (3)0.037 (4)0.053 (4)
C100.036 (3)0.069 (4)0.138 (7)0.024 (3)0.009 (4)0.037 (4)
C110.055 (4)0.099 (5)0.080 (4)0.041 (4)0.002 (3)0.040 (4)
C120.042 (3)0.067 (3)0.050 (3)0.030 (3)0.009 (2)0.024 (3)
C130.039 (3)0.023 (2)0.043 (3)0.0114 (18)0.005 (2)0.0113 (19)
C140.038 (2)0.036 (2)0.035 (2)0.013 (2)0.0032 (19)0.0131 (19)
C150.042 (3)0.078 (4)0.045 (3)0.019 (3)0.010 (2)0.024 (3)
C160.040 (3)0.103 (5)0.059 (4)0.025 (3)0.001 (3)0.023 (4)
C170.057 (4)0.076 (4)0.052 (4)0.027 (3)0.016 (3)0.017 (3)
C180.080 (5)0.075 (4)0.043 (3)0.025 (3)0.009 (3)0.028 (3)
C190.051 (3)0.053 (3)0.050 (3)0.011 (2)0.010 (2)0.025 (3)
C200.031 (2)0.035 (2)0.048 (3)0.0168 (19)0.015 (2)0.020 (2)
C210.045 (3)0.043 (3)0.055 (3)0.029 (2)0.025 (2)0.026 (2)
C220.062 (3)0.043 (3)0.066 (4)0.025 (3)0.036 (3)0.027 (3)
C230.092 (5)0.068 (4)0.082 (4)0.052 (4)0.063 (4)0.048 (4)
C240.093 (5)0.079 (4)0.053 (4)0.054 (4)0.038 (3)0.026 (3)
C250.074 (4)0.060 (3)0.055 (4)0.030 (3)0.029 (3)0.014 (3)
C260.048 (3)0.051 (3)0.053 (3)0.022 (2)0.026 (2)0.023 (2)
C270.051 (3)0.054 (3)0.089 (4)0.024 (3)0.028 (3)0.047 (3)
C280.063 (4)0.076 (4)0.104 (5)0.024 (3)0.033 (4)0.068 (4)
C290.081 (5)0.054 (4)0.103 (5)0.003 (3)0.015 (4)0.059 (4)
C300.092 (5)0.034 (3)0.079 (4)0.010 (3)0.000 (4)0.030 (3)
C310.052 (3)0.028 (2)0.050 (3)0.011 (2)0.004 (2)0.022 (2)
Geometric parameters (Å, º) top
Tb1—N12.565 (3)C5—C311.463 (8)
Tb1—N22.586 (4)C6—C71.501 (6)
Tb1—O6i2.364 (3)C7—C81.377 (7)
Tb1—O3i2.377 (3)C7—C121.377 (7)
Tb1—O52.379 (3)C8—C91.382 (8)
Tb1—O22.418 (3)C8—H80.9300
Tb1—O42.481 (3)C9—C101.347 (10)
Tb1—O12.498 (3)C10—C111.367 (10)
Tb1—O32.696 (3)C10—H100.9300
F1—C221.347 (6)C11—C121.373 (8)
F2—C251.365 (7)C11—H110.9300
F3—C121.331 (6)C13—C141.508 (6)
F4—C91.344 (7)C14—C191.363 (7)
F5—C151.294 (7)C14—C151.374 (7)
F5—H150.3691C15—C161.362 (7)
F6—C181.353 (9)C15—H150.9300
F6—H180.4290C16—C171.346 (9)
F7—C191.286 (11)C16—H160.9300
F7—H190.3654C17—C181.354 (9)
F8—C161.392 (13)C17—H170.9300
F8—H160.4706C18—C191.362 (8)
O1—C131.258 (6)C18—H180.9300
O2—C131.254 (6)C19—H190.9300
O3—C61.259 (5)C20—C211.495 (6)
O3—Tb1i2.377 (3)C21—C221.372 (6)
O4—C61.239 (5)C21—C261.393 (7)
O5—C201.248 (5)C22—C231.375 (7)
O6—C201.252 (5)C23—C241.373 (9)
O6—Tb1i2.364 (3)C23—H230.9300
N1—C271.325 (7)C24—C251.351 (8)
N1—C311.347 (6)C24—H240.9300
N2—C11.315 (7)C25—C261.364 (7)
N2—C51.345 (6)C26—H260.9300
C1—C21.394 (7)C27—C281.371 (7)
C1—H10.9300C27—H270.9300
C2—C31.342 (9)C28—C291.332 (10)
C2—H20.9300C28—H280.9300
C3—C41.354 (9)C29—C301.378 (10)
C3—H30.9300C29—H290.9300
C4—C51.385 (7)C30—C311.394 (7)
C4—H40.9300C30—H300.9300
O6i—Tb1—O3i75.94 (10)C10—C9—C8122.7 (6)
O6i—Tb1—O5132.93 (10)C9—C10—C11119.2 (6)
O3i—Tb1—O574.31 (10)C9—C10—H10120.4
O6i—Tb1—O2132.91 (12)C11—C10—H10120.4
O3i—Tb1—O278.22 (11)C10—C11—C12118.9 (6)
O5—Tb1—O274.15 (11)C10—C11—H11120.5
O6i—Tb1—O484.77 (12)C12—C11—H11120.5
O3i—Tb1—O4123.24 (9)F3—C12—C11118.8 (5)
O5—Tb1—O482.03 (11)F3—C12—C7118.7 (4)
O2—Tb1—O4142.07 (12)C11—C12—C7122.4 (6)
O6i—Tb1—O184.52 (12)O2—C13—O1121.4 (4)
O3i—Tb1—O181.13 (10)O2—C13—C14118.7 (4)
O5—Tb1—O1125.07 (10)O1—C13—C14119.8 (4)
O2—Tb1—O152.89 (11)O2—C13—Tb159.2 (2)
O4—Tb1—O1149.70 (10)O1—C13—Tb162.9 (2)
O6i—Tb1—N179.45 (12)C14—C13—Tb1167.8 (3)
O3i—Tb1—N1145.03 (12)C19—C14—C15115.9 (5)
O5—Tb1—N1139.96 (12)C19—C14—C13120.2 (4)
O2—Tb1—N1101.74 (13)C15—C14—C13123.9 (4)
O4—Tb1—N178.13 (11)F5—C15—C16115.0 (6)
O1—Tb1—N172.07 (11)F5—C15—C14122.3 (5)
O6i—Tb1—N2138.65 (12)C16—C15—C14122.7 (5)
O3i—Tb1—N2145.39 (12)F5—C15—H153.3
O5—Tb1—N278.18 (11)C16—C15—H15118.3
O2—Tb1—N274.34 (12)C14—C15—H15119.0
O4—Tb1—N272.15 (11)C17—C16—C15120.4 (6)
O1—Tb1—N298.32 (12)C17—C16—F8123.5 (7)
N1—Tb1—N262.76 (14)C15—C16—F8115.9 (7)
O6i—Tb1—O370.68 (10)C17—C16—H16120.1
O3i—Tb1—O373.82 (10)C15—C16—H16119.5
O5—Tb1—O366.47 (10)F8—C16—H164.6
O2—Tb1—O3136.36 (10)C16—C17—C18117.8 (5)
O4—Tb1—O349.42 (9)C16—C17—H17121.1
O1—Tb1—O3148.14 (10)C18—C17—H17121.1
N1—Tb1—O3120.33 (11)C17—C18—F6122.6 (6)
N2—Tb1—O3113.49 (10)C17—C18—C19122.0 (6)
C15—F5—H158.4F6—C18—C19115.3 (7)
C18—F6—H188.0C17—C18—H18119.2
C19—F7—H1911.1F6—C18—H183.7
C16—F8—H169.1C19—C18—H18118.8
C13—O1—Tb190.5 (3)F7—C19—C18114.6 (7)
C13—O2—Tb194.3 (3)F7—C19—C14124.2 (6)
C6—O3—Tb1i163.2 (3)C18—C19—C14121.1 (5)
C6—O3—Tb188.4 (2)F7—C19—H194.4
Tb1i—O3—Tb1106.18 (10)C18—C19—H19119.0
C6—O4—Tb199.1 (2)C14—C19—H19119.9
C20—O5—Tb1136.0 (3)O5—C20—O6125.8 (4)
C20—O6—Tb1i134.3 (3)O5—C20—C21115.8 (4)
C27—N1—C31118.3 (4)O6—C20—C21118.4 (4)
C27—N1—Tb1119.6 (3)C22—C21—C26117.6 (5)
C31—N1—Tb1121.0 (3)C22—C21—C20124.3 (4)
C1—N2—C5117.7 (4)C26—C21—C20118.1 (4)
C1—N2—Tb1121.2 (3)F1—C22—C21119.9 (5)
C5—N2—Tb1121.1 (3)F1—C22—C23118.5 (5)
N2—C1—C2124.0 (5)C21—C22—C23121.5 (5)
N2—C1—H1118.0C24—C23—C22120.5 (5)
C2—C1—H1118.0C24—C23—H23119.7
C3—C2—C1117.5 (6)C22—C23—H23119.7
C3—C2—H2121.2C25—C24—C23117.6 (5)
C1—C2—H2121.2C25—C24—H24121.2
C2—C3—C4120.0 (5)C23—C24—H24121.2
C2—C3—H3120.0C24—C25—C26123.2 (6)
C4—C3—H3120.0C24—C25—F2118.2 (5)
C3—C4—C5120.1 (5)C26—C25—F2118.5 (5)
C3—C4—H4120.0C25—C26—C21119.4 (5)
C5—C4—H4120.0C25—C26—H26120.3
N2—C5—C4120.7 (6)C21—C26—H26120.3
N2—C5—C31116.6 (4)N1—C27—C28124.0 (6)
C4—C5—C31122.6 (5)N1—C27—H27118.0
O4—C6—O3120.9 (4)C28—C27—H27118.0
O4—C6—C7119.8 (4)C29—C28—C27118.4 (7)
O3—C6—C7119.2 (4)C29—C28—H28120.8
O4—C6—Tb156.3 (2)C27—C28—H28120.8
O3—C6—Tb166.3 (2)C28—C29—C30119.8 (5)
C7—C6—Tb1162.8 (3)C28—C29—H29120.1
C8—C7—C12118.1 (5)C30—C29—H29120.1
C8—C7—C6119.9 (4)C29—C30—C31119.7 (6)
C12—C7—C6122.0 (4)C29—C30—H30120.2
C7—C8—C9118.6 (5)C31—C30—H30120.2
C7—C8—H8120.7N1—C31—C30119.9 (6)
C9—C8—H8120.7N1—C31—C5116.7 (4)
F4—C9—C10119.3 (6)C30—C31—C5123.4 (5)
F4—C9—C8118.0 (6)
O6i—Tb1—O1—C13153.0 (3)O1—Tb1—C6—O380.4 (4)
O3i—Tb1—O1—C1376.4 (2)N1—Tb1—C6—O3142.7 (2)
O5—Tb1—O1—C1312.8 (3)N2—Tb1—C6—O3155.0 (3)
O2—Tb1—O1—C135.5 (2)C13—Tb1—C6—O370.9 (7)
O4—Tb1—O1—C13137.2 (3)O6i—Tb1—C6—C7178.3 (10)
N1—Tb1—O1—C13126.3 (3)O3i—Tb1—C6—C7104.4 (9)
N2—Tb1—O1—C1368.6 (3)O5—Tb1—C6—C734.8 (9)
O3—Tb1—O1—C13114.7 (3)O2—Tb1—C6—C722.2 (10)
C6—Tb1—O1—C13167.7 (3)O4—Tb1—C6—C782.4 (10)
O6i—Tb1—O2—C1324.4 (3)O1—Tb1—C6—C7166.9 (8)
O3i—Tb1—O2—C1382.2 (3)N1—Tb1—C6—C7104.6 (9)
O5—Tb1—O2—C13159.0 (3)N2—Tb1—C6—C742.3 (9)
O4—Tb1—O2—C13147.7 (2)O3—Tb1—C6—C7112.7 (10)
O1—Tb1—O2—C135.5 (2)C13—Tb1—C6—C741.8 (13)
N1—Tb1—O2—C1362.0 (3)O4—C6—C7—C8119.8 (5)
N2—Tb1—O2—C13119.1 (3)O3—C6—C7—C856.7 (6)
O3—Tb1—O2—C13133.1 (2)Tb1—C6—C7—C847.9 (11)
C6—Tb1—O2—C13171.4 (2)O4—C6—C7—C1257.6 (6)
O6i—Tb1—O3—C6108.2 (3)O3—C6—C7—C12126.0 (5)
O3i—Tb1—O3—C6171.4 (3)Tb1—C6—C7—C12129.5 (9)
O5—Tb1—O3—C691.8 (3)C12—C7—C8—C90.5 (8)
O2—Tb1—O3—C6119.2 (3)C6—C7—C8—C9176.9 (5)
O4—Tb1—O3—C68.2 (2)C7—C8—C9—F4178.5 (5)
O1—Tb1—O3—C6149.0 (2)C7—C8—C9—C102.2 (10)
N1—Tb1—O3—C643.6 (3)F4—C9—C10—C11178.5 (6)
N2—Tb1—O3—C627.5 (3)C8—C9—C10—C112.2 (11)
C13—Tb1—O3—C6158.5 (3)C9—C10—C11—C120.4 (10)
O6i—Tb1—O3—Tb1i80.42 (12)C10—C11—C12—F3178.8 (6)
O3i—Tb1—O3—Tb1i0.0C10—C11—C12—C71.2 (10)
O5—Tb1—O3—Tb1i79.59 (12)C8—C7—C12—F3178.9 (5)
O2—Tb1—O3—Tb1i52.25 (19)C6—C7—C12—F31.5 (7)
O4—Tb1—O3—Tb1i179.60 (19)C8—C7—C12—C111.1 (8)
O1—Tb1—O3—Tb1i39.5 (2)C6—C7—C12—C11178.6 (5)
N1—Tb1—O3—Tb1i144.96 (13)Tb1—O2—C13—O110.3 (4)
N2—Tb1—O3—Tb1i143.93 (13)Tb1—O2—C13—C14166.2 (3)
C13—Tb1—O3—Tb1i12.9 (3)Tb1—O1—C13—O29.9 (4)
C6—Tb1—O3—Tb1i171.4 (3)Tb1—O1—C13—C14166.5 (3)
O6i—Tb1—O4—C677.4 (3)O6i—Tb1—C13—O2161.4 (2)
O3i—Tb1—O4—C68.0 (3)O3i—Tb1—C13—O291.6 (3)
O5—Tb1—O4—C657.3 (3)O5—Tb1—C13—O220.4 (3)
O2—Tb1—O4—C6108.4 (3)O4—Tb1—C13—O270.9 (5)
O1—Tb1—O4—C6147.1 (3)O1—Tb1—C13—O2170.2 (4)
N1—Tb1—O4—C6157.7 (3)N1—Tb1—C13—O2120.1 (3)
N2—Tb1—O4—C6137.4 (3)N2—Tb1—C13—O257.3 (3)
O3—Tb1—O4—C68.4 (3)O3—Tb1—C13—O278.8 (3)
C13—Tb1—O4—C6151.6 (4)C6—Tb1—C13—O227.0 (7)
O6i—Tb1—O5—C2043.3 (5)O6i—Tb1—C13—O128.4 (3)
O3i—Tb1—O5—C209.4 (4)O3i—Tb1—C13—O198.2 (3)
O2—Tb1—O5—C2091.3 (4)O5—Tb1—C13—O1169.4 (2)
O4—Tb1—O5—C20118.5 (4)O2—Tb1—C13—O1170.2 (4)
O1—Tb1—O5—C2076.2 (4)O4—Tb1—C13—O199.3 (4)
N1—Tb1—O5—C20179.2 (4)N1—Tb1—C13—O150.1 (3)
N2—Tb1—O5—C20168.2 (4)N2—Tb1—C13—O1112.8 (3)
O3—Tb1—O5—C2069.5 (4)O3—Tb1—C13—O1111.0 (3)
C13—Tb1—O5—C2082.0 (4)C6—Tb1—C13—O1162.9 (5)
C6—Tb1—O5—C2096.6 (4)O6i—Tb1—C13—C1477.8 (17)
O6i—Tb1—N1—C2718.5 (4)O3i—Tb1—C13—C148.0 (17)
O3i—Tb1—N1—C2727.2 (5)O5—Tb1—C13—C1463.2 (17)
O5—Tb1—N1—C27167.3 (3)O2—Tb1—C13—C1483.6 (17)
O2—Tb1—N1—C27113.4 (4)O4—Tb1—C13—C14154.5 (15)
O4—Tb1—N1—C27105.4 (4)O1—Tb1—C13—C14106.2 (17)
O1—Tb1—N1—C2769.0 (4)N1—Tb1—C13—C14156.3 (17)
N2—Tb1—N1—C27178.8 (4)N2—Tb1—C13—C14140.9 (17)
O3—Tb1—N1—C2778.6 (4)O3—Tb1—C13—C144.8 (18)
C13—Tb1—N1—C2790.2 (4)C6—Tb1—C13—C1457 (2)
C6—Tb1—N1—C2796.1 (4)O2—C13—C14—C1914.5 (6)
O6i—Tb1—N1—C31173.7 (4)O1—C13—C14—C19162.0 (4)
O3i—Tb1—N1—C31140.5 (3)Tb1—C13—C14—C1962.3 (18)
O5—Tb1—N1—C3124.9 (4)O2—C13—C14—C15166.1 (5)
O2—Tb1—N1—C3154.3 (3)O1—C13—C14—C1517.4 (7)
O4—Tb1—N1—C3186.9 (3)Tb1—C13—C14—C15117.2 (16)
O1—Tb1—N1—C3198.7 (3)C19—C14—C15—F5179.9 (7)
N2—Tb1—N1—C3111.0 (3)C13—C14—C15—F50.6 (10)
O3—Tb1—N1—C31113.6 (3)C19—C14—C15—C160.1 (9)
C13—Tb1—N1—C3177.5 (3)C13—C14—C15—C16179.5 (5)
C6—Tb1—N1—C3196.1 (3)F5—C15—C16—C17178.9 (7)
O6i—Tb1—N2—C1147.6 (3)C14—C15—C16—C171.2 (10)
O3i—Tb1—N2—C134.8 (4)F5—C15—C16—F82.9 (13)
O5—Tb1—N2—C13.0 (4)C14—C15—C16—F8177.2 (10)
O2—Tb1—N2—C173.6 (4)C15—C16—C17—C181.6 (10)
O4—Tb1—N2—C188.3 (4)F8—C16—C17—C18177.3 (11)
O1—Tb1—N2—C1121.2 (4)C16—C17—C18—F6177.0 (8)
N1—Tb1—N2—C1173.9 (4)C16—C17—C18—C191.0 (10)
O3—Tb1—N2—C160.6 (4)C17—C18—C19—F7179.9 (10)
C13—Tb1—N2—C196.6 (4)F6—C18—C19—F71.9 (12)
C6—Tb1—N2—C172.0 (4)C17—C18—C19—C140.1 (10)
O6i—Tb1—N2—C531.1 (4)F6—C18—C19—C14178.3 (7)
O3i—Tb1—N2—C5146.5 (3)C15—C14—C19—F7179.7 (10)
O5—Tb1—N2—C5175.7 (3)C13—C14—C19—F70.9 (12)
O2—Tb1—N2—C5107.7 (3)C15—C14—C19—C180.6 (8)
O4—Tb1—N2—C590.3 (3)C13—C14—C19—C18178.9 (5)
O1—Tb1—N2—C560.1 (3)Tb1—O5—C20—O647.9 (6)
N1—Tb1—N2—C54.8 (3)Tb1—O5—C20—C21130.2 (4)
O3—Tb1—N2—C5118.1 (3)Tb1i—O6—C20—O524.7 (7)
C13—Tb1—N2—C584.8 (3)Tb1i—O6—C20—C21153.4 (3)
C6—Tb1—N2—C5106.7 (3)O5—C20—C21—C22147.8 (5)
C5—N2—C1—C20.7 (7)O6—C20—C21—C2233.9 (7)
Tb1—N2—C1—C2178.1 (4)O5—C20—C21—C2633.5 (6)
N2—C1—C2—C30.4 (9)O6—C20—C21—C26144.8 (4)
C1—C2—C3—C40.0 (9)C26—C21—C22—F1176.8 (5)
C2—C3—C4—C50.0 (9)C20—C21—C22—F14.6 (7)
C1—N2—C5—C40.7 (7)C26—C21—C22—C230.4 (8)
Tb1—N2—C5—C4178.1 (3)C20—C21—C22—C23178.3 (5)
C1—N2—C5—C31179.7 (4)F1—C22—C23—C24178.5 (5)
Tb1—N2—C5—C311.0 (5)C21—C22—C23—C241.3 (9)
C3—C4—C5—N20.4 (7)C22—C23—C24—C251.9 (9)
C3—C4—C5—C31179.3 (5)C23—C24—C25—C260.8 (9)
Tb1—O4—C6—O316.1 (5)C23—C24—C25—F2179.6 (5)
Tb1—O4—C6—C7160.3 (3)C24—C25—C26—C210.9 (9)
Tb1i—O3—C6—O4165.0 (7)F2—C25—C26—C21178.0 (5)
Tb1—O3—C6—O414.6 (4)C22—C21—C26—C251.5 (7)
Tb1i—O3—C6—C711.5 (12)C20—C21—C26—C25177.3 (5)
Tb1—O3—C6—C7161.8 (4)C31—N1—C27—C281.3 (8)
Tb1i—O3—C6—Tb1150.4 (10)Tb1—N1—C27—C28166.8 (4)
O6i—Tb1—C6—O499.4 (3)N1—C27—C28—C290.4 (9)
O3i—Tb1—C6—O4173.3 (3)C27—C28—C29—C301.1 (10)
O5—Tb1—C6—O4117.2 (3)C28—C29—C30—C310.2 (10)
O2—Tb1—C6—O4104.6 (3)C27—N1—C31—C302.2 (7)
O1—Tb1—C6—O484.5 (5)Tb1—N1—C31—C30165.7 (4)
N1—Tb1—C6—O422.3 (3)C27—N1—C31—C5175.9 (4)
N2—Tb1—C6—O440.1 (3)Tb1—N1—C31—C516.1 (5)
O3—Tb1—C6—O4164.9 (5)C29—C30—C31—N11.5 (8)
C13—Tb1—C6—O4124.1 (6)C29—C30—C31—C5176.5 (5)
O6i—Tb1—C6—O365.6 (2)N2—C5—C31—N111.0 (6)
O3i—Tb1—C6—O38.3 (3)C4—C5—C31—N1168.0 (4)
O5—Tb1—C6—O377.9 (2)N2—C5—C31—C30170.9 (5)
O2—Tb1—C6—O390.5 (3)C4—C5—C31—C3010.1 (7)
O4—Tb1—C6—O3164.9 (5)
Symmetry code: (i) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formula[Tb2(C7H3F2O2)6(C10H8N2)2]
Mr1572.77
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.401 (1), 12.189 (1), 12.588 (2)
α, β, γ (°)103.99 (2), 102.90 (2), 113.58 (2)
V3)1451.5 (3)
Z1
Radiation typeMo Kα
µ (mm1)2.52
Crystal size (mm)0.44 × 0.26 × 0.20
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.403, 0.632
No. of measured, independent and
observed [I > 2σ(I)] reflections
8233, 5557, 4813
Rint0.021
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.078, 1.03
No. of reflections5557
No. of parameters434
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.60, 0.57

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Tb1—N12.565 (3)Tb1—O22.418 (3)
Tb1—N22.586 (4)Tb1—O42.481 (3)
Tb1—O6i2.364 (3)Tb1—O12.498 (3)
Tb1—O3i2.377 (3)Tb1—O32.696 (3)
Tb1—O52.379 (3)
Symmetry code: (i) x+1, y+2, z+1.
 

Acknowledgements

This work was supported by the Natural Science Foundation of Shandong Province (grant No. Y2007D39).

References

First citationBruker (2001). SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSerre, C., Marrot, J. & Ferey, G. (2005). Inorg. Chem. 44, 654–658.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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