Tetra­kis(μ-2,4-difluoro­benzoato)bis­[(2,4-difluoro­benzoato)(1,10-phenanthroline)gadolinium(III)]

Wang, S.-B.; He, H.-M.; Li, S.; Tang, K.

doi:10.1107/S1600536808004431

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m516

doi:10.1107/S1600536808004431

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Tetrakis(μ-2,4-difluorobenzoato)bis[(2,4-difluorobenzoato)(1,10-phenanthroline)gadolinium(III)]

Shou-Bin Wang,^a ^* Hong-Mei He,^b Sheng Li ^b and Kun Tang ^b

^aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475003, People's Republic of China, and ^bCollege of Medicine, Henan University, Kaifeng 475003, People's Republic of China
^*Correspondence e-mail: wangsb6688@sina.com

(Received 2 February 2008; accepted 14 February 2008; online 5 March 2008)

In the title compound, [Gd₂(C₇H₃F₂O₂)₆(C₁₂H₈N₂)₂], the asymmetric unit comprises one Gd³⁺ cation chelated by two 2,4-difluorobenzoate and one 1,10-phenanthroline ligands. Two cations are linked into a centrosymmetric dimer via three bridging carboxylate groups of 2,4-difluorobenzoate ligands. Each Gd³⁺ ion is nine-coordinated by seven O atoms and two N atoms.

Related literature

For related literature, see: Church & Halvorson (1959 ); Chung et al. (1971 ); Okabe & Oya (2000 ); Serre et al. (2005 ); Pocker & Fong (1980 ); Scapin et al. (1997 ).

Experimental

Crystal data

[Gd₂(C₇H₃F₂O₂)₆(C₁₂H₈N₂)₂]
M_r = 1617.47
Monoclinic, P 2₁ /n
a = 15.132 (3) Å
b = 13.663 (3) Å
c = 15.286 (3) Å
β = 109.364 (2)°
V = 2981.6 (9) Å³
Z = 2
Mo Kα radiation
μ = 2.31 mm⁻¹
T = 295 (2) K
0.33 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.516, T_max = 0.837
15634 measured reflections
5535 independent reflections
4598 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.095
S = 1.00
5535 reflections
433 parameters
H-atom parameters constrained
Δρ_max = 1.69 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004431/cf2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004431/cf2184Isup2.hkl

checkCIF report

Comment top

In recent years, carboxylates have been widely used as polydentate ligands, which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science (Church & Halvorson, 1959; Chung et al., 1971) and in biological systems (Okabe & Oya, 2000; Serre et al., 2005; Pocker & Fong, 1980; Scapin et al., 1997). Here we report the synthesis and X-ray crystal structure analysis of the title compound.

The molecular structure is shown in Fig. 1. Gd(III) is chelated by two 2,4-difluorobenzoate and one 1,10-phenanthroline ligands. Two cations are linked into a dimer via three bridging carboxylate groups of 2,4-difluorobenzoate ligands. Each Gd(III) ion is nine-coordinated by seven O atoms and two N atoms.

Related literature top

For related literature, see: Church & Halvorson (1959); Chung et al. (1971); Okabe & Oya (2000); Serre et al. (2005); Pocker & Fong (1980); Scapin et al. (1997).

Experimental top

A mixture of gadolinium(III) chloride (0.5 mmol), 2,4-difluorobenzoic acid (1 mmol), sodium hydroxide (1 mmol), 1,10-phenanthroline (0.5 mmol), water (8 ml) and ethanol (8 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 433 K for three days. Colorless crystals were obtained after cooling to room temperature, with a yield of 16%. Anal. Calc. for C₃₃H₁₇F₆GdN₂O₆: C 48.98, H 2.10, N 3.46%; Found: C 48.88, H 2.12, N 3.98%.

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

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. Unlabeled atoms are at the symmetry position (-x + 2, -y, -z + 2).

Tetrakis(µ-2,4-difluorobenzoato)bis[(2,4-difluorobenzoato)(1,10- phenanthroline)gadolinium(III)] top

Crystal data top

[Gd₂(C₇H₃F₂O₂)₆(C₁₂H₈N₂)₂]	F(000) = 1580
M_r = 1617.47	D_x = 1.802 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5535 reflections
a = 15.132 (3) Å	θ = 2.1–25.5°
b = 13.663 (3) Å	µ = 2.31 mm⁻¹
c = 15.286 (3) Å	T = 295 K
β = 109.364 (2)°	Block, colourless
V = 2981.6 (9) Å³	0.33 × 0.14 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	5535 independent reflections
Radiation source: fine-focus sealed tube	4598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→18
T_min = 0.516, T_max = 0.837	k = −16→16
15634 measured reflections	l = −17→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0528P)² + 4.39P] where P = (F_o² + 2F_c²)/3
5535 reflections	(Δ/σ)_max = 0.008
433 parameters	Δρ_max = 1.69 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Gd₂(C₇H₃F₂O₂)₆(C₁₂H₈N₂)₂]	V = 2981.6 (9) Å³
M_r = 1617.47	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.132 (3) Å	µ = 2.31 mm⁻¹
b = 13.663 (3) Å	T = 295 K
c = 15.286 (3) Å	0.33 × 0.14 × 0.08 mm
β = 109.364 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5535 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4598 reflections with I > 2σ(I)
T_min = 0.516, T_max = 0.837	R_int = 0.037
15634 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.00	Δρ_max = 1.69 e Å⁻³
5535 reflections	Δρ_min = −0.64 e Å⁻³
433 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

	x	y	z	U_iso*/U_eq
Gd1	0.997885 (14)	0.144628 (14)	0.957975 (13)	0.02862 (9)
C1	1.1346 (3)	0.2166 (3)	0.8849 (3)	0.0373 (10)
C2	1.2110 (3)	0.2446 (3)	0.8476 (3)	0.0428 (11)
C3	1.1982 (4)	0.2280 (4)	0.7539 (4)	0.0530 (13)
H3	1.1411	0.2041	0.7152	0.064*
C4	1.2694 (5)	0.2467 (5)	0.7181 (4)	0.0725 (19)
H4	1.2606	0.2353	0.6558	0.087*
C5	1.3513 (5)	0.2816 (5)	0.7747 (5)	0.076 (2)
C6	1.3667 (5)	0.2995 (6)	0.8637 (6)	0.095 (3)
H6	1.4243	0.3240	0.9009	0.113*
C7	1.2965 (4)	0.2815 (5)	0.9009 (4)	0.0667 (17)
C8	0.9247 (3)	−0.0549 (3)	0.8221 (3)	0.0316 (9)
C9	0.9086 (3)	−0.0732 (3)	0.7207 (3)	0.0328 (9)
C10	0.9380 (3)	−0.0029 (3)	0.6705 (3)	0.0413 (11)
H10	0.9713	0.0512	0.7013	0.050*
C11	0.9189 (4)	−0.0117 (4)	0.5764 (3)	0.0573 (14)
H11	0.9399	0.0351	0.5437	0.069*
C12	0.8686 (5)	−0.0904 (5)	0.5324 (3)	0.0656 (17)
C13	0.8377 (4)	−0.1626 (4)	0.5768 (3)	0.0541 (14)
H13	0.8030	−0.2153	0.5446	0.065*
C14	0.8605 (3)	−0.1536 (3)	0.6721 (3)	0.0407 (11)
C15	0.8390 (3)	0.0592 (3)	1.0120 (3)	0.0344 (9)
C16	0.7585 (3)	0.0448 (3)	1.0482 (3)	0.0422 (11)
C17	0.7753 (5)	0.0095 (4)	1.1374 (4)	0.0631 (16)
H17	0.8347	−0.0130	1.1717	0.076*
C18	0.7040 (6)	0.0075 (5)	1.1760 (5)	0.085 (2)
H18	0.7150	−0.0182	1.2350	0.102*
C19	0.6197 (6)	0.0427 (6)	1.1277 (6)	0.092 (3)
C20	0.5978 (4)	0.0755 (5)	1.0382 (5)	0.0761 (19)
H20	0.5378	0.0968	1.0048	0.091*
C21	0.6685 (4)	0.0755 (4)	0.9998 (4)	0.0532 (13)
C22	0.9877 (4)	0.3346 (4)	1.1111 (3)	0.0454 (12)
H22	1.0244	0.2895	1.1532	0.054*
C23	0.9628 (4)	0.4212 (4)	1.1453 (4)	0.0553 (14)
H23	0.9809	0.4318	1.2089	0.066*
C24	0.9121 (4)	0.4896 (4)	1.0857 (4)	0.0548 (14)
H24	0.8961	0.5479	1.1082	0.066*
C25	0.8838 (3)	0.4726 (3)	0.9899 (4)	0.0440 (11)
C26	0.9099 (3)	0.3819 (3)	0.9608 (3)	0.0371 (10)
C27	0.8324 (4)	0.5425 (4)	0.9223 (4)	0.0569 (15)
H27	0.8156	0.6020	0.9418	0.068*
C28	0.8081 (4)	0.5232 (4)	0.8309 (4)	0.0547 (14)
H28	0.7764	0.5704	0.7882	0.066*
C29	0.8303 (3)	0.4316 (3)	0.7986 (4)	0.0452 (11)
C30	0.8798 (3)	0.3602 (3)	0.8629 (3)	0.0361 (10)
C31	0.8017 (4)	0.4072 (4)	0.7045 (4)	0.0551 (14)
H31	0.7696	0.4526	0.6600	0.066*
C32	0.8213 (4)	0.3157 (5)	0.6782 (4)	0.0598 (15)
H32	0.8018	0.2980	0.6160	0.072*
C33	0.8708 (4)	0.2504 (4)	0.7466 (3)	0.0480 (12)
H33	0.8836	0.1887	0.7281	0.058*
F1	1.3151 (4)	0.3046 (6)	0.9873 (4)	0.153 (3)
F2	1.4208 (3)	0.3002 (4)	0.7394 (4)	0.133 (2)
F3	0.8319 (2)	−0.2247 (2)	0.71639 (19)	0.0520 (7)
F4	0.8467 (4)	−0.0971 (4)	0.4386 (2)	0.1107 (16)
F5	0.6472 (2)	0.1067 (3)	0.9116 (2)	0.0688 (9)
F6	0.5496 (4)	0.0443 (4)	1.1648 (4)	0.141 (2)
N1	0.9615 (2)	0.3134 (3)	1.0209 (2)	0.0331 (8)
N2	0.9010 (3)	0.2706 (3)	0.8367 (2)	0.0355 (8)
O1	1.1385 (2)	0.2404 (3)	0.9662 (2)	0.0486 (8)
O2	1.0671 (2)	0.1674 (2)	0.8334 (2)	0.0418 (7)
O3	0.9197 (2)	0.0335 (2)	0.84238 (19)	0.0360 (7)
O4	0.9422 (2)	−0.1250 (2)	0.8774 (2)	0.0398 (7)
O5	0.8436 (2)	0.1391 (2)	0.9743 (2)	0.0440 (8)
O6	0.8994 (2)	−0.0069 (2)	1.0241 (2)	0.0449 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Gd1	0.03159 (14)	0.02662 (13)	0.02902 (13)	−0.00158 (8)	0.01190 (9)	−0.00349 (8)
C1	0.043 (3)	0.030 (2)	0.045 (3)	−0.0028 (19)	0.022 (2)	−0.0029 (19)
C2	0.046 (3)	0.036 (3)	0.055 (3)	−0.009 (2)	0.029 (2)	−0.006 (2)
C3	0.060 (3)	0.056 (3)	0.054 (3)	−0.016 (3)	0.034 (3)	−0.004 (2)
C4	0.087 (5)	0.082 (5)	0.071 (4)	−0.032 (4)	0.056 (4)	−0.020 (3)
C5	0.075 (4)	0.088 (5)	0.094 (5)	−0.041 (4)	0.065 (4)	−0.042 (4)
C6	0.060 (4)	0.118 (7)	0.118 (6)	−0.048 (4)	0.047 (4)	−0.043 (5)
C7	0.062 (4)	0.089 (5)	0.058 (3)	−0.031 (3)	0.031 (3)	−0.033 (3)
C8	0.028 (2)	0.033 (2)	0.034 (2)	−0.0040 (17)	0.0107 (17)	−0.0075 (18)
C9	0.034 (2)	0.034 (2)	0.028 (2)	0.0058 (18)	0.0075 (17)	−0.0058 (17)
C10	0.049 (3)	0.039 (3)	0.039 (2)	0.005 (2)	0.020 (2)	−0.002 (2)
C11	0.081 (4)	0.058 (3)	0.042 (3)	0.010 (3)	0.032 (3)	0.006 (3)
C12	0.095 (5)	0.072 (4)	0.031 (3)	0.014 (3)	0.021 (3)	−0.009 (3)
C13	0.067 (4)	0.054 (3)	0.034 (3)	0.004 (3)	0.006 (2)	−0.019 (2)
C14	0.046 (3)	0.035 (3)	0.038 (2)	0.008 (2)	0.011 (2)	−0.0043 (19)
C15	0.031 (2)	0.040 (2)	0.033 (2)	0.0016 (19)	0.0113 (18)	−0.0068 (19)
C16	0.047 (3)	0.031 (2)	0.057 (3)	−0.001 (2)	0.029 (2)	−0.001 (2)
C17	0.089 (5)	0.047 (3)	0.071 (4)	0.018 (3)	0.051 (3)	0.011 (3)
C18	0.117 (6)	0.069 (4)	0.103 (5)	0.022 (4)	0.081 (5)	0.028 (4)
C19	0.104 (6)	0.080 (5)	0.134 (7)	0.002 (4)	0.095 (6)	0.020 (5)
C20	0.049 (3)	0.073 (4)	0.120 (6)	−0.006 (3)	0.047 (4)	0.006 (4)
C21	0.044 (3)	0.044 (3)	0.079 (4)	−0.006 (2)	0.030 (3)	0.005 (3)
C22	0.053 (3)	0.041 (3)	0.045 (3)	−0.003 (2)	0.020 (2)	−0.010 (2)
C23	0.065 (3)	0.055 (3)	0.056 (3)	−0.012 (3)	0.033 (3)	−0.024 (3)
C24	0.057 (3)	0.038 (3)	0.078 (4)	−0.004 (2)	0.034 (3)	−0.023 (3)
C25	0.035 (2)	0.031 (2)	0.070 (3)	−0.0048 (19)	0.023 (2)	−0.010 (2)
C26	0.030 (2)	0.032 (2)	0.053 (3)	−0.0045 (18)	0.018 (2)	−0.006 (2)
C27	0.044 (3)	0.029 (3)	0.095 (5)	0.004 (2)	0.019 (3)	−0.006 (3)
C28	0.040 (3)	0.036 (3)	0.082 (4)	0.003 (2)	0.012 (3)	0.011 (3)
C29	0.035 (2)	0.037 (3)	0.062 (3)	0.001 (2)	0.014 (2)	0.010 (2)
C30	0.030 (2)	0.031 (2)	0.049 (3)	−0.0040 (17)	0.015 (2)	−0.0011 (19)
C31	0.049 (3)	0.054 (3)	0.059 (3)	0.007 (3)	0.015 (3)	0.023 (3)
C32	0.062 (4)	0.073 (4)	0.039 (3)	0.008 (3)	0.010 (3)	0.009 (3)
C33	0.055 (3)	0.051 (3)	0.037 (3)	0.010 (2)	0.013 (2)	0.000 (2)
F1	0.123 (4)	0.247 (7)	0.102 (4)	−0.105 (5)	0.056 (3)	−0.058 (4)
F2	0.114 (4)	0.163 (5)	0.174 (5)	−0.081 (4)	0.116 (4)	−0.077 (4)
F3	0.0626 (18)	0.0388 (15)	0.0505 (16)	−0.0103 (13)	0.0131 (14)	−0.0080 (13)
F4	0.176 (5)	0.118 (4)	0.0343 (18)	−0.005 (3)	0.030 (2)	−0.014 (2)
F5	0.0458 (18)	0.080 (2)	0.076 (2)	0.0011 (17)	0.0149 (17)	0.0107 (19)
F6	0.130 (4)	0.150 (5)	0.206 (6)	0.017 (3)	0.141 (4)	0.043 (4)
N1	0.0321 (19)	0.0286 (18)	0.042 (2)	0.0002 (15)	0.0168 (16)	−0.0034 (16)
N2	0.038 (2)	0.033 (2)	0.0369 (19)	0.0011 (16)	0.0140 (16)	−0.0016 (16)
O1	0.053 (2)	0.054 (2)	0.0486 (19)	−0.0209 (17)	0.0298 (17)	−0.0205 (16)
O2	0.0395 (18)	0.0489 (19)	0.0399 (17)	−0.0076 (15)	0.0170 (15)	−0.0039 (15)
O3	0.0447 (18)	0.0327 (16)	0.0306 (15)	−0.0033 (13)	0.0124 (13)	−0.0070 (12)
O4	0.057 (2)	0.0307 (16)	0.0282 (15)	−0.0037 (14)	0.0100 (14)	−0.0012 (13)
O5	0.0467 (19)	0.0359 (18)	0.057 (2)	−0.0036 (14)	0.0269 (17)	0.0006 (15)
O6	0.0462 (19)	0.049 (2)	0.0405 (18)	0.0153 (16)	0.0155 (15)	0.0000 (15)

Geometric parameters (Å, º) top

Gd1—O3	2.332 (3)	C15—C16	1.509 (6)
Gd1—O4ⁱ	2.391 (3)	C16—C21	1.382 (7)
Gd1—O6ⁱ	2.397 (3)	C16—C17	1.388 (7)
Gd1—O5	2.429 (3)	C17—C18	1.391 (9)
Gd1—O1	2.465 (3)	C17—H17	0.930
Gd1—O2	2.479 (3)	C18—C19	1.334 (11)
Gd1—N2	2.597 (4)	C18—H18	0.930
Gd1—N1	2.627 (3)	C19—F6	1.359 (7)
Gd1—O6	2.921 (4)	C19—C20	1.372 (10)
C1—O2	1.257 (5)	C20—C21	1.381 (8)
C1—O1	1.267 (5)	C20—H20	0.930
C1—C2	1.499 (6)	C21—F5	1.346 (6)
C2—C7	1.376 (7)	C22—N1	1.334 (6)
C2—C3	1.398 (7)	C22—C23	1.395 (7)
C3—C4	1.385 (7)	C22—H22	0.930
C3—H3	0.930	C23—C24	1.353 (8)
C4—C5	1.342 (9)	C23—H23	0.930
C4—H4	0.930	C24—C25	1.402 (7)
C5—C6	1.325 (10)	C24—H24	0.930
C5—F2	1.355 (6)	C25—C26	1.416 (6)
C6—C7	1.383 (9)	C25—C27	1.431 (7)
C6—H6	0.930	C26—N1	1.362 (6)
C7—F1	1.295 (7)	C26—C30	1.444 (7)
C8—O4	1.246 (5)	C27—C28	1.348 (8)
C8—O3	1.256 (5)	C27—H27	0.930
C8—C9	1.507 (5)	C28—C29	1.426 (7)
C9—C14	1.390 (6)	C28—H28	0.930
C9—C10	1.391 (6)	C29—C31	1.398 (8)
C10—C11	1.376 (6)	C29—C30	1.411 (6)
C10—H10	0.930	C30—N2	1.358 (5)
C11—C12	1.360 (8)	C31—C32	1.375 (8)
C11—H11	0.930	C31—H31	0.930
C12—C13	1.364 (9)	C32—C33	1.390 (7)
C12—F4	1.364 (6)	C32—H32	0.930
C13—C14	1.387 (7)	C33—N2	1.329 (6)
C13—H13	0.930	C33—H33	0.930
C14—F3	1.335 (6)	O4—Gd1ⁱ	2.391 (3)
C15—O5	1.247 (5)	O6—Gd1ⁱ	2.397 (3)
C15—O6	1.255 (5)

O3—Gd1—O4ⁱ	130.13 (10)	F3—C14—C13	117.3 (4)
O3—Gd1—O6ⁱ	73.87 (11)	F3—C14—C9	120.3 (4)
O4ⁱ—Gd1—O6ⁱ	77.68 (10)	C13—C14—C9	122.4 (5)
O3—Gd1—O5	78.14 (11)	O5—C15—O6	123.2 (4)
O4ⁱ—Gd1—O5	85.99 (12)	O5—C15—C16	117.4 (4)
O6ⁱ—Gd1—O5	124.91 (11)	O6—C15—C16	119.3 (4)
O3—Gd1—O1	126.62 (10)	C21—C16—C17	117.4 (5)
O4ⁱ—Gd1—O1	89.20 (11)	C21—C16—C15	122.3 (4)
O6ⁱ—Gd1—O1	83.97 (12)	C17—C16—C15	119.9 (5)
O5—Gd1—O1	148.60 (11)	C16—C17—C18	120.6 (6)
O3—Gd1—O2	74.75 (10)	C16—C17—H17	119.7
O4ⁱ—Gd1—O2	135.54 (11)	C18—C17—H17	119.7
O6ⁱ—Gd1—O2	76.31 (11)	C19—C18—C17	119.5 (6)
O5—Gd1—O2	138.42 (11)	C19—C18—H18	120.3
O1—Gd1—O2	52.79 (10)	C17—C18—H18	120.3
O3—Gd1—N2	82.32 (11)	C18—C19—F6	120.7 (7)
O4ⁱ—Gd1—N2	138.85 (11)	C18—C19—C20	122.7 (6)
O6ⁱ—Gd1—N2	142.42 (11)	F6—C19—C20	116.5 (8)
O5—Gd1—N2	76.13 (11)	C19—C20—C21	117.4 (6)
O1—Gd1—N2	87.58 (12)	C19—C20—H20	121.3
O2—Gd1—N2	69.53 (11)	C21—C20—H20	121.3
O3—Gd1—N1	137.20 (11)	F5—C21—C20	117.7 (5)
O4ⁱ—Gd1—N1	76.43 (11)	F5—C21—C16	119.9 (5)
O6ⁱ—Gd1—N1	148.65 (11)	C20—C21—C16	122.4 (6)
O5—Gd1—N1	70.40 (11)	N1—C22—C23	123.1 (5)
O1—Gd1—N1	78.31 (11)	N1—C22—H22	118.4
O2—Gd1—N1	111.36 (11)	C23—C22—H22	118.4
N2—Gd1—N1	62.75 (11)	C24—C23—C22	119.8 (5)
O3—Gd1—O6	67.18 (9)	C24—C23—H23	120.1
O4ⁱ—Gd1—O6	67.33 (10)	C22—C23—H23	120.1
O6ⁱ—Gd1—O6	77.87 (11)	C23—C24—C25	119.9 (5)
O5—Gd1—O6	47.51 (10)	C23—C24—H24	120.1
O1—Gd1—O6	152.79 (11)	C25—C24—H24	120.1
O2—Gd1—O6	138.53 (10)	C24—C25—C26	116.9 (5)
N2—Gd1—O6	119.04 (10)	C24—C25—C27	123.2 (5)
N1—Gd1—O6	107.62 (10)	C26—C25—C27	119.8 (5)
O2—C1—O1	121.1 (4)	N1—C26—C25	123.1 (4)
O2—C1—C2	117.8 (4)	N1—C26—C30	118.1 (4)
O1—C1—C2	121.1 (4)	C25—C26—C30	118.8 (4)
C7—C2—C3	116.7 (5)	C28—C27—C25	121.0 (5)
C7—C2—C1	124.1 (4)	C28—C27—H27	119.5
C3—C2—C1	119.1 (4)	C25—C27—H27	119.5
C4—C3—C2	120.9 (5)	C27—C28—C29	121.0 (5)
C4—C3—H3	119.6	C27—C28—H28	119.5
C2—C3—H3	119.6	C29—C28—H28	119.5
C5—C4—C3	119.0 (5)	C31—C29—C30	117.6 (5)
C5—C4—H4	120.5	C31—C29—C28	122.5 (5)
C3—C4—H4	120.5	C30—C29—C28	119.9 (5)
C6—C5—C4	122.6 (6)	N2—C30—C29	122.7 (4)
C6—C5—F2	118.5 (6)	N2—C30—C26	117.8 (4)
C4—C5—F2	118.9 (6)	C29—C30—C26	119.4 (4)
C5—C6—C7	119.4 (6)	C32—C31—C29	119.7 (5)
C5—C6—H6	120.3	C32—C31—H31	120.2
C7—C6—H6	120.3	C29—C31—H31	120.2
F1—C7—C2	122.5 (5)	C31—C32—C33	118.6 (5)
F1—C7—C6	116.0 (6)	C31—C32—H32	120.7
C2—C7—C6	121.4 (5)	C33—C32—H32	120.7
O4—C8—O3	126.0 (4)	N2—C33—C32	124.1 (5)
O4—C8—C9	119.7 (4)	N2—C33—H33	117.9
O3—C8—C9	114.2 (4)	C32—C33—H33	117.9
C14—C9—C10	117.2 (4)	C22—N1—C26	117.1 (4)
C14—C9—C8	123.9 (4)	C22—N1—Gd1	122.8 (3)
C10—C9—C8	118.7 (4)	C26—N1—Gd1	119.9 (3)
C11—C10—C9	121.5 (5)	C33—N2—C30	117.3 (4)
C11—C10—H10	119.3	C33—N2—Gd1	121.4 (3)
C9—C10—H10	119.3	C30—N2—Gd1	121.3 (3)
C12—C11—C10	118.3 (5)	C1—O1—Gd1	93.1 (3)
C12—C11—H11	120.8	C1—O2—Gd1	92.7 (3)
C10—C11—H11	120.8	C8—O3—Gd1	139.2 (3)
C11—C12—C13	123.7 (5)	C8—O4—Gd1ⁱ	136.2 (3)
C11—C12—F4	118.3 (6)	C15—O5—Gd1	106.2 (3)
C13—C12—F4	118.1 (6)	C15—O6—Gd1ⁱ	174.2 (3)
C12—C13—C14	116.8 (5)	C15—O6—Gd1	82.5 (3)
C12—C13—H13	121.6	Gd1ⁱ—O6—Gd1	102.13 (11)
C14—C13—H13	121.6

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Gd₂(C₇H₃F₂O₂)₆(C₁₂H₈N₂)₂]
M_r	1617.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	15.132 (3), 13.663 (3), 15.286 (3)
β (°)	109.364 (2)
V (Å³)	2981.6 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.31
Crystal size (mm)	0.33 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.516, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	15634, 5535, 4598
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.095, 1.00
No. of reflections	5535
No. of parameters	433
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.69, −0.64

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

Acknowledgements

The authors acknowledge the financial support of Henan University (grant No. 05YBGG013).

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chung, L., Rajan, K. S., Merdinger, E. & Crecz, N. (1971). Biophys. J. 11, 469–475. CrossRef CAS Web of Science PubMed Google Scholar
Church, B. S. & Halvorson, H. (1959). Nature (London), 183, 124–125. CrossRef PubMed CAS Web of Science Google Scholar
Okabe, N. & Oya, N. (2000). Acta Cryst. C56, 1416–1417. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pocker, Y. & Fong, C. T. O. (1980). Biochemistry, 19, 2045–2049. CrossRef CAS PubMed Web of Science Google Scholar
Scapin, G., Reddy, S. G., Zheng, R. & Blanchard, J. S. (1997). Biochemistry, 36, 15081–15088. CrossRef CAS PubMed Web of Science Google Scholar
Serre, C., Marrot, J. & Ferey, G. (2005). Inorg. Chem. 44, 654–658. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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