metal-organic compounds
(E)-4-[4-(Dimethylamino)styryl]-1-methylpyridin-1-ium tetrakis[(Z)-4,4,4-trifluoro-3-oxo-1-(thiophen-2-yl)but-1-en-1-olato]gadolinate(III) with an unknown amount of water as solvate
aDepartment of Chemistry, Anhui University, Hefei 230601, People's Republic of China, Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230601, People's Republic of China
*Correspondence e-mail: 1277436413@qq.com
In the complex anion of the title salt, (C16H19N2)[Gd(C8H4F3S)4], the GaIII cation is O,O′-chelated by four anionic 4,4,4-trifluoro-3-oxo-1-(thiophen-2-yl)but-1-en-1-olate ligands in a distorted square-antiprismatic geometry; the 4-[4-(dimethylamino)styryl]-1-methylpyridin-1-ium cation is nearly planar, with a dihedral angle of 9.6 (5)° between the planes of the pyridine and benzene rings. In the crystal, the cations are linked with the complex anions via weak C—H⋯F and C—H⋯π interactions. Two of the four independent thiophene rings are disordered over two sites; occupancies were refined to 0.662 (10):0.338 (10). The solvent water molecules are highly disordered in a solvent-accessible void of 54 (3) Å3; the diffuse electron densities were removed from the data set using SQUEEZE [Spek (2015). Acta Cryst. C71, 9–16]. These solvent molecules are not considered in the given chemical formula and other crystal data.
Keywords: crystal structure; GdIII complex anion; 4-[4-(dimethylamino)styryl]-1-methylpyridin-1-ium cation; weak C—H⋯F interaction.
CCDC reference: 1511879
Structure description
In recent decades, the construction of lanthanide-based metal–organic complexes has attracted widespread attention due to their essential photophysical properties which have potential applications in luminescent materials (Cui et al., 2012), optical amplification (Bradley & Pollnau, 2011), magnetic materials, pressure and impact sensors, and biological systems. (Bünzli & Eliseeva, 2013). According to these excellent properties, a new pyridinium complex consisting of p-aminostyryl-pyridinium cation and a gadolinium(III) complex anion was synthesized by an ionic exchange reaction.
As shown in Fig. 1, the of the title complex contains one GdIII cation, four bidentate TTA− (4,4,4-trifluoro-1,3-dioxo-1-(thiophen-2-yl)butan-2-ide) anions and one (E)-4-(4-(dimethylamino)styryl)-1-methylpyridin-1-ium cation. The central GdIII cation is coordinated by eight oxygen atoms from four bidentate TTA− anions, which presents typical O,O-chelates. The coordination environment of the GdIII cation is shown in Fig. 2. The Gd—O bond lengths range from 2.366 (5) to 2.419 (4)°, which deviate from the average of 2.385°. Eight different bond lengths generate a distorted square antiprism with the two square planes comprising atoms (O1,O2,O8,O7) and (O3,O4,O6,O5). The dihedral angle between these planes is 0.269 (1)°.
Synthesis and crystallization
1,4-Dimethylpyridinium iodide and (E)-4-(4-(dimethylamino) styryl)-1-methylpyridin-1-ium iodide were prepared using established literature methods (Zhao et al., 1995a,b). For the preparation of the title complex, Gd(NO3)3·6H2O (0.45 g, 1 mmol) dissolved in ethanol solution was added dropwise into a 4,4,4-trifluoro-1-(thiophen-2-yl)butane-1,3-dione (HTTA, 0.89 g, 4 mmol) and aqueous NaOH (0.16 g, 4 mmol) solution that reacted to form the intermediate 4,4,4-trifluoro-1,3-dioxo-1-(thiophen-2-yl)butan-2-ide (TTA−), then (E)-4-[4-(dimethylamino)styryl]-1-methylpyridin-1-ium iodide (0.37 g, 1 mmol) was added into the solution. After refluxing for half an hour, the precipitate was filtered off and recrystallized from ethanol solution. Single crystals of the title complex were gained by slow evaporation of methanol covered with acetonitrile at room temperature. 1H NMR: (400 MHz, CD3COCD3-d6), (p.p.m.): 10.30 (d, 2H), 8.90 (d,2H), 8.14 (d, 1H), 7.68 (d, 2H), 7.43 (d, 1H), 7.25 (d, 4H), 6.85 (d, 2H),6.73 (d, 4H), 6.67–6.60 (m, 4H), 5.69 (s, 4H), 4.05 (s, 3H), 3.11 (s, 6H).
Refinement
Crystal data, data collection and structure . The residual solvent water molecules were highly disordered and could not be found and refined. The diffuse electron densities of these residual solvent molecules were removed from the data set by the SQUEEZE routine of PLATON (Spek, 2015) software, and then the generated data were used to further refine the structure.
details are summarized in Table 1Structural data
CCDC reference: 1511879
https://doi.org/10.1107/S2414314616017272/xu4016sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017272/xu4016Isup2.hkl
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).(C16H19N2)[Gd(C8H4F3S)4] | F(000) = 2548 |
Mr = 1281.27 | Dx = 1.616 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 9929 reflections |
a = 10.500 (5) Å | θ = 2.2–24.3° |
b = 21.888 (5) Å | µ = 1.51 mm−1 |
c = 23.348 (5) Å | T = 298 K |
β = 101.145 (5)° | Block, red |
V = 5265 (3) Å3 | 0.24 × 0.22 × 0.21 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 9781 independent reflections |
Radiation source: fine-focus sealed tube | 7812 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
phi and ω scans | θmax = 25.5°, θmin = 1.3° |
Absorption correction: ψ scan (SADABS; Bruker, 2007) | h = −11→12 |
Tmin = 0.713, Tmax = 0.742 | k = −25→26 |
37288 measured reflections | l = −28→28 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0384P)2 + 26.1086P] where P = (Fo2 + 2Fc2)/3 |
9781 reflections | (Δ/σ)max = 0.020 |
770 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −1.42 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S2 | 0.5249 (17) | 0.6856 (12) | 0.4449 (8) | 0.090 (3) | 0.662 (10) |
C41 | 0.494 (7) | 0.6822 (17) | 0.512 (3) | 0.086 (10) | 0.662 (10) |
H41 | 0.4114 | 0.6758 | 0.5194 | 0.103* | 0.662 (10) |
C42 | 0.604 (9) | 0.690 (3) | 0.555 (4) | 0.080 (12) | 0.662 (10) |
H42 | 0.6057 | 0.6901 | 0.5953 | 0.096* | 0.662 (10) |
C43 | 0.717 (5) | 0.697 (3) | 0.528 (2) | 0.078 (14) | 0.662 (10) |
H43 | 0.8016 | 0.7027 | 0.5483 | 0.094* | 0.662 (10) |
C44 | 0.68 (2) | 0.694 (9) | 0.467 (10) | 0.06 (2) | 0.662 (10) |
S2' | 0.748 (3) | 0.7062 (16) | 0.5382 (12) | 0.073 (5) | 0.338 (10) |
C42' | 0.509 (13) | 0.706 (3) | 0.511 (6) | 0.09 (2) | 0.338 (10) |
H42' | 0.4243 | 0.7095 | 0.5173 | 0.105* | 0.338 (10) |
C41' | 0.622 (19) | 0.709 (5) | 0.556 (9) | 0.08 (2) | 0.338 (10) |
H41' | 0.6164 | 0.7128 | 0.5955 | 0.099* | 0.338 (10) |
C43' | 0.547 (11) | 0.697 (7) | 0.454 (5) | 0.10 (4) | 0.338 (10) |
H43' | 0.4921 | 0.6910 | 0.4181 | 0.114* | 0.338 (10) |
C44' | 0.70 (4) | 0.698 (18) | 0.47 (2) | 0.06 (5) | 0.338 (10) |
S4 | 0.311 (2) | 0.7632 (9) | 0.2735 (9) | 0.077 (2) | 0.662 (10) |
C33 | 0.181 (8) | 0.808 (3) | 0.249 (3) | 0.082 (17) | 0.662 (10) |
H33 | 0.1055 | 0.8057 | 0.2640 | 0.098* | 0.662 (10) |
C34 | 0.198 (6) | 0.849 (3) | 0.2038 (19) | 0.082 (11) | 0.662 (10) |
H34 | 0.1338 | 0.8753 | 0.1855 | 0.099* | 0.662 (10) |
C35 | 0.326 (9) | 0.844 (4) | 0.190 (4) | 0.08 (3) | 0.662 (10) |
H35 | 0.3586 | 0.8664 | 0.1620 | 0.098* | 0.662 (10) |
C36 | 0.392 (9) | 0.796 (4) | 0.226 (4) | 0.06 (3) | 0.662 (10) |
S4' | 0.308 (6) | 0.852 (2) | 0.1931 (19) | 0.079 (6) | 0.338 (10) |
C34' | 0.183 (18) | 0.791 (7) | 0.263 (7) | 0.08 (2) | 0.338 (10) |
H34' | 0.1202 | 0.7746 | 0.2821 | 0.093* | 0.338 (10) |
C33' | 0.181 (11) | 0.842 (5) | 0.224 (3) | 0.07 (2) | 0.338 (10) |
H33' | 0.1099 | 0.8683 | 0.2167 | 0.087* | 0.338 (10) |
C35' | 0.319 (14) | 0.772 (6) | 0.264 (6) | 0.09 (5) | 0.338 (10) |
H35' | 0.3538 | 0.7418 | 0.2905 | 0.109* | 0.338 (10) |
C36' | 0.40 (2) | 0.795 (8) | 0.228 (8) | 0.07 (6) | 0.338 (10) |
C1 | −0.2577 (12) | 0.3626 (6) | 0.0335 (6) | 0.123 (5) | |
H1A | −0.2329 | 0.3472 | −0.0012 | 0.184* | |
H1B | −0.3507 | 0.3647 | 0.0278 | 0.184* | |
H1C | −0.2255 | 0.3359 | 0.0656 | 0.184* | |
C2 | −0.2884 (11) | 0.4743 (6) | 0.0322 (5) | 0.110 (4) | |
H2A | −0.2806 | 0.5007 | 0.0655 | 0.166* | |
H2B | −0.3763 | 0.4602 | 0.0214 | 0.166* | |
H2C | −0.2653 | 0.4965 | 0.0002 | 0.166* | |
C3 | −0.0744 (11) | 0.4306 (5) | 0.0667 (4) | 0.080 (3) | |
C4 | 0.0107 (12) | 0.3808 (5) | 0.0796 (5) | 0.103 (4) | |
H4 | −0.0209 | 0.3412 | 0.0733 | 0.123* | |
C5 | 0.1423 (12) | 0.3905 (5) | 0.1016 (5) | 0.103 (4) | |
H5 | 0.1952 | 0.3563 | 0.1105 | 0.123* | |
C6 | 0.1986 (11) | 0.4468 (5) | 0.1111 (4) | 0.081 (3) | |
C7 | 0.1139 (11) | 0.4955 (5) | 0.0988 (4) | 0.084 (3) | |
H7 | 0.1470 | 0.5348 | 0.1055 | 0.101* | |
C8 | −0.0152 (11) | 0.4888 (5) | 0.0772 (4) | 0.082 (3) | |
H8 | −0.0665 | 0.5236 | 0.0692 | 0.099* | |
C9 | 0.3388 (12) | 0.4575 (5) | 0.1357 (4) | 0.087 (3) | |
H9 | 0.3644 | 0.4976 | 0.1449 | 0.104* | |
C10 | 0.4279 (12) | 0.4159 (5) | 0.1454 (4) | 0.087 (3) | |
H10 | 0.4043 | 0.3754 | 0.1373 | 0.104* | |
C11 | 0.5645 (11) | 0.4299 (4) | 0.1686 (4) | 0.075 (3) | |
C12 | 0.6550 (12) | 0.3826 (4) | 0.1725 (4) | 0.088 (3) | |
H12 | 0.6270 | 0.3433 | 0.1613 | 0.105* | |
C13 | 0.7826 (11) | 0.3931 (4) | 0.1923 (4) | 0.083 (3) | |
H13 | 0.8412 | 0.3609 | 0.1952 | 0.100* | |
C14 | 0.7437 (11) | 0.4988 (4) | 0.2029 (4) | 0.081 (3) | |
H14 | 0.7750 | 0.5383 | 0.2107 | 0.097* | |
C15 | 0.6147 (10) | 0.4878 (4) | 0.1862 (4) | 0.077 (3) | |
H15 | 0.5571 | 0.5200 | 0.1864 | 0.092* | |
C16 | 0.9678 (10) | 0.4600 (5) | 0.2285 (5) | 0.099 (3) | |
H16A | 0.9879 | 0.4589 | 0.2704 | 0.148* | |
H16B | 0.9915 | 0.4992 | 0.2152 | 0.148* | |
H16C | 1.0154 | 0.4286 | 0.2131 | 0.148* | |
C17 | 1.1792 (11) | 0.4745 (5) | 0.4335 (5) | 0.095 (3) | |
H17 | 1.2678 | 0.4666 | 0.4427 | 0.115* | |
C18 | 1.0904 (13) | 0.4435 (5) | 0.4554 (4) | 0.092 (3) | |
H18 | 1.1132 | 0.4124 | 0.4825 | 0.111* | |
C19 | 0.9631 (8) | 0.4601 (3) | 0.4355 (3) | 0.0549 (19) | |
H19 | 0.8910 | 0.4416 | 0.4457 | 0.066* | |
C20 | 0.9601 (8) | 0.5110 (3) | 0.3961 (3) | 0.0546 (19) | |
C21 | 0.8490 (7) | 0.5459 (3) | 0.3634 (3) | 0.0472 (17) | |
C22 | 0.7215 (7) | 0.5298 (3) | 0.3675 (3) | 0.0545 (19) | |
H22 | 0.7091 | 0.5017 | 0.3957 | 0.065* | |
C23 | 0.6151 (7) | 0.5539 (3) | 0.3316 (3) | 0.0532 (18) | |
C24 | 0.4809 (9) | 0.5292 (5) | 0.3360 (4) | 0.073 (3) | |
C25 | 1.3133 (8) | 0.6296 (4) | 0.1907 (5) | 0.073 (3) | |
H25 | 1.4007 | 0.6220 | 0.2053 | 0.087* | |
C26 | 1.2682 (10) | 0.6534 (5) | 0.1378 (5) | 0.084 (3) | |
H26 | 1.3233 | 0.6646 | 0.1128 | 0.101* | |
C27 | 1.1305 (7) | 0.6606 (3) | 0.1221 (4) | 0.060 (2) | |
H27 | 1.0840 | 0.6753 | 0.0868 | 0.071* | |
C28 | 1.0779 (7) | 0.6407 (3) | 0.1718 (3) | 0.0489 (17) | |
C29 | 0.9424 (6) | 0.6419 (3) | 0.1792 (3) | 0.0432 (15) | |
C30 | 0.8405 (7) | 0.6459 (4) | 0.1295 (3) | 0.0506 (18) | |
H30 | 0.8608 | 0.6486 | 0.0925 | 0.061* | |
C31 | 0.7144 (7) | 0.6457 (3) | 0.1349 (3) | 0.0474 (17) | |
C32 | 0.6096 (8) | 0.6440 (5) | 0.0784 (3) | 0.066 (2) | |
C37 | 0.5247 (8) | 0.7746 (3) | 0.2253 (3) | 0.0493 (17) | |
C38 | 0.5972 (8) | 0.8030 (4) | 0.1872 (3) | 0.057 (2) | |
H38 | 0.5545 | 0.8292 | 0.1584 | 0.069* | |
C39 | 0.7265 (8) | 0.7933 (3) | 0.1912 (3) | 0.0536 (19) | |
C40 | 0.7969 (11) | 0.8301 (5) | 0.1504 (5) | 0.086 (3) | |
C45 | 0.7666 (7) | 0.6981 (3) | 0.4222 (3) | 0.0520 (18) | |
C46 | 0.9019 (7) | 0.7033 (4) | 0.4371 (3) | 0.0543 (19) | |
H46 | 0.9416 | 0.7006 | 0.4762 | 0.065* | |
C47 | 0.9790 (7) | 0.7124 (3) | 0.3960 (3) | 0.0485 (17) | |
C48 | 1.1227 (9) | 0.7182 (5) | 0.4182 (4) | 0.071 (2) | |
F1 | 0.4821 (6) | 0.4883 (3) | 0.3774 (3) | 0.130 (3) | |
F2 | 0.4023 (5) | 0.5737 (3) | 0.3442 (3) | 0.108 (2) | |
F3 | 0.4230 (6) | 0.5022 (3) | 0.2871 (3) | 0.115 (2) | |
F4 | 1.1657 (6) | 0.6989 (5) | 0.4695 (3) | 0.175 (4) | |
F5 | 1.1919 (6) | 0.6924 (5) | 0.3847 (4) | 0.164 (4) | |
F6 | 1.1618 (8) | 0.7730 (4) | 0.4169 (5) | 0.193 (5) | |
F7 | 0.8944 (7) | 0.7999 (3) | 0.1369 (3) | 0.128 (3) | |
F8 | 0.8487 (10) | 0.8796 (4) | 0.1753 (4) | 0.173 (4) | |
F9 | 0.7234 (8) | 0.8450 (4) | 0.1012 (3) | 0.159 (4) | |
F10 | 0.5265 (6) | 0.5973 (3) | 0.0786 (2) | 0.0957 (18) | |
F11 | 0.5367 (5) | 0.6943 (3) | 0.0729 (2) | 0.0931 (17) | |
F12 | 0.6568 (5) | 0.6376 (4) | 0.0298 (2) | 0.110 (2) | |
Gd1 | 0.76013 (3) | 0.672150 (16) | 0.279170 (14) | 0.03944 (11) | |
N1 | −0.2036 (9) | 0.4232 (4) | 0.0462 (4) | 0.095 (3) | |
N2 | 0.8261 (8) | 0.4500 (3) | 0.2079 (3) | 0.074 (2) | |
O1 | 0.6103 (4) | 0.5937 (2) | 0.2912 (2) | 0.0522 (12) | |
O2 | 0.8757 (5) | 0.5884 (2) | 0.3318 (2) | 0.0559 (13) | |
O3 | 0.7060 (5) | 0.6942 (3) | 0.3707 (2) | 0.0621 (15) | |
O4 | 0.9438 (5) | 0.7172 (2) | 0.3414 (2) | 0.0561 (13) | |
O5 | 0.5705 (4) | 0.7338 (2) | 0.2614 (2) | 0.0519 (12) | |
O6 | 0.8026 (5) | 0.7606 (2) | 0.2270 (2) | 0.0491 (12) | |
O7 | 0.6642 (4) | 0.6448 (2) | 0.17983 (18) | 0.0455 (11) | |
O8 | 0.9229 (4) | 0.6357 (2) | 0.2300 (2) | 0.0509 (12) | |
S1 | 1.1113 (2) | 0.52987 (14) | 0.38679 (13) | 0.0916 (8) | |
S3 | 1.1934 (2) | 0.61484 (13) | 0.22812 (11) | 0.0787 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2 | 0.066 (4) | 0.143 (9) | 0.064 (4) | −0.006 (4) | 0.022 (3) | −0.012 (4) |
C41 | 0.084 (17) | 0.11 (3) | 0.068 (13) | 0.00 (2) | 0.027 (12) | −0.01 (2) |
C42 | 0.08 (2) | 0.10 (4) | 0.059 (13) | 0.01 (3) | 0.025 (14) | 0.00 (3) |
C43 | 0.08 (3) | 0.09 (2) | 0.07 (2) | 0.005 (17) | 0.019 (17) | −0.004 (15) |
C44 | 0.06 (4) | 0.09 (7) | 0.05 (3) | 0.01 (4) | 0.02 (3) | 0.00 (4) |
S2' | 0.078 (11) | 0.088 (9) | 0.057 (7) | 0.005 (7) | 0.024 (8) | 0.002 (7) |
C42' | 0.08 (4) | 0.10 (6) | 0.08 (3) | 0.00 (4) | 0.03 (3) | −0.01 (5) |
C41' | 0.09 (5) | 0.10 (6) | 0.07 (3) | 0.00 (5) | 0.03 (3) | 0.00 (5) |
C43' | 0.10 (8) | 0.12 (6) | 0.07 (6) | 0.02 (5) | 0.04 (5) | 0.01 (5) |
C44' | 0.06 (8) | 0.07 (7) | 0.06 (8) | −0.01 (6) | 0.01 (4) | 0.00 (4) |
S4 | 0.063 (4) | 0.097 (5) | 0.080 (4) | 0.019 (4) | 0.032 (4) | −0.007 (5) |
C33 | 0.065 (14) | 0.09 (5) | 0.09 (5) | 0.02 (3) | 0.01 (3) | −0.01 (2) |
C34 | 0.07 (2) | 0.089 (18) | 0.09 (3) | 0.025 (14) | 0.007 (19) | −0.02 (2) |
C35 | 0.06 (4) | 0.08 (3) | 0.10 (3) | 0.017 (18) | 0.002 (18) | −0.011 (16) |
C36 | 0.05 (4) | 0.07 (4) | 0.07 (4) | 0.02 (3) | 0.01 (3) | −0.02 (3) |
S4' | 0.060 (11) | 0.082 (11) | 0.088 (11) | 0.013 (12) | 0.000 (8) | 0.002 (11) |
C34' | 0.07 (3) | 0.08 (6) | 0.08 (6) | 0.02 (4) | 0.01 (3) | 0.00 (3) |
C33' | 0.06 (3) | 0.08 (4) | 0.07 (6) | 0.03 (4) | 0.01 (4) | −0.01 (4) |
C35' | 0.07 (5) | 0.12 (7) | 0.09 (7) | 0.02 (4) | 0.03 (4) | 0.01 (4) |
C36' | 0.07 (9) | 0.08 (9) | 0.06 (7) | 0.01 (6) | 0.00 (6) | 0.01 (5) |
C1 | 0.116 (10) | 0.117 (10) | 0.120 (10) | −0.017 (8) | −0.016 (8) | −0.040 (8) |
C2 | 0.104 (9) | 0.125 (10) | 0.094 (8) | 0.030 (8) | −0.002 (7) | 0.000 (7) |
C3 | 0.095 (8) | 0.070 (6) | 0.072 (6) | 0.009 (6) | 0.011 (5) | −0.013 (5) |
C4 | 0.103 (9) | 0.061 (6) | 0.140 (10) | 0.005 (6) | 0.009 (8) | −0.021 (6) |
C5 | 0.095 (9) | 0.074 (7) | 0.135 (10) | 0.024 (6) | 0.013 (7) | 0.009 (7) |
C6 | 0.092 (8) | 0.073 (7) | 0.078 (6) | −0.004 (6) | 0.014 (5) | −0.005 (5) |
C7 | 0.100 (8) | 0.067 (6) | 0.083 (7) | 0.004 (6) | 0.013 (6) | −0.009 (5) |
C8 | 0.100 (8) | 0.072 (6) | 0.072 (6) | 0.021 (6) | 0.010 (6) | −0.006 (5) |
C9 | 0.122 (9) | 0.057 (6) | 0.085 (7) | −0.006 (6) | 0.031 (6) | −0.006 (5) |
C10 | 0.119 (9) | 0.060 (6) | 0.085 (7) | −0.011 (6) | 0.031 (6) | −0.005 (5) |
C11 | 0.098 (8) | 0.073 (6) | 0.055 (5) | −0.011 (6) | 0.018 (5) | 0.005 (4) |
C12 | 0.121 (9) | 0.056 (6) | 0.075 (6) | −0.011 (6) | −0.005 (6) | 0.005 (5) |
C13 | 0.111 (9) | 0.062 (6) | 0.068 (6) | 0.011 (6) | −0.004 (6) | 0.011 (5) |
C14 | 0.119 (9) | 0.049 (5) | 0.083 (6) | −0.013 (6) | 0.039 (6) | 0.026 (4) |
C15 | 0.091 (7) | 0.058 (6) | 0.089 (7) | −0.008 (5) | 0.036 (6) | −0.004 (5) |
C16 | 0.094 (8) | 0.097 (8) | 0.096 (8) | 0.007 (7) | −0.002 (6) | 0.006 (6) |
C17 | 0.073 (7) | 0.115 (9) | 0.088 (7) | 0.051 (7) | −0.011 (6) | 0.007 (7) |
C18 | 0.126 (10) | 0.074 (7) | 0.073 (6) | 0.039 (7) | 0.011 (7) | 0.019 (5) |
C19 | 0.062 (5) | 0.051 (4) | 0.049 (4) | 0.004 (4) | 0.004 (4) | 0.011 (3) |
C20 | 0.064 (5) | 0.047 (4) | 0.052 (4) | 0.010 (4) | 0.007 (4) | 0.003 (3) |
C21 | 0.052 (4) | 0.039 (4) | 0.052 (4) | 0.002 (3) | 0.012 (3) | 0.004 (3) |
C22 | 0.055 (5) | 0.052 (5) | 0.058 (4) | 0.000 (4) | 0.013 (4) | 0.015 (4) |
C23 | 0.052 (5) | 0.054 (5) | 0.054 (4) | −0.008 (4) | 0.013 (4) | 0.002 (4) |
C24 | 0.049 (5) | 0.091 (7) | 0.083 (6) | −0.006 (5) | 0.022 (5) | 0.017 (6) |
C25 | 0.034 (4) | 0.081 (6) | 0.109 (8) | −0.004 (4) | 0.029 (5) | −0.024 (6) |
C26 | 0.072 (7) | 0.094 (8) | 0.099 (8) | −0.013 (5) | 0.045 (6) | −0.010 (6) |
C27 | 0.042 (4) | 0.059 (5) | 0.087 (6) | 0.000 (4) | 0.035 (4) | 0.005 (4) |
C28 | 0.036 (4) | 0.050 (4) | 0.062 (4) | 0.004 (3) | 0.014 (3) | −0.005 (4) |
C29 | 0.040 (4) | 0.040 (4) | 0.051 (4) | 0.006 (3) | 0.013 (3) | 0.002 (3) |
C30 | 0.043 (4) | 0.071 (5) | 0.042 (4) | 0.009 (4) | 0.020 (3) | 0.001 (3) |
C31 | 0.057 (4) | 0.062 (4) | 0.025 (3) | 0.020 (4) | 0.013 (3) | −0.011 (3) |
C32 | 0.055 (5) | 0.094 (7) | 0.047 (4) | 0.022 (5) | 0.003 (4) | 0.001 (4) |
C37 | 0.048 (5) | 0.045 (4) | 0.053 (4) | 0.007 (4) | 0.004 (3) | −0.007 (3) |
C38 | 0.053 (5) | 0.057 (5) | 0.060 (5) | 0.013 (4) | 0.007 (4) | 0.017 (4) |
C39 | 0.069 (5) | 0.049 (4) | 0.045 (4) | 0.005 (4) | 0.014 (4) | 0.013 (3) |
C40 | 0.101 (8) | 0.080 (7) | 0.087 (7) | 0.036 (7) | 0.042 (6) | 0.040 (6) |
C45 | 0.054 (5) | 0.049 (4) | 0.052 (4) | 0.006 (4) | 0.006 (4) | 0.006 (3) |
C46 | 0.053 (5) | 0.066 (5) | 0.041 (4) | 0.000 (4) | 0.002 (3) | 0.003 (3) |
C47 | 0.055 (4) | 0.045 (4) | 0.043 (4) | −0.011 (3) | 0.004 (3) | 0.005 (3) |
C48 | 0.056 (5) | 0.090 (7) | 0.065 (5) | −0.020 (5) | 0.009 (4) | 0.008 (5) |
F1 | 0.083 (4) | 0.160 (6) | 0.148 (6) | −0.026 (4) | 0.028 (4) | 0.086 (5) |
F2 | 0.066 (4) | 0.115 (5) | 0.153 (6) | −0.001 (3) | 0.046 (4) | 0.003 (4) |
F3 | 0.087 (4) | 0.131 (6) | 0.125 (5) | −0.054 (4) | 0.014 (4) | −0.018 (4) |
F4 | 0.058 (4) | 0.350 (13) | 0.104 (5) | −0.025 (5) | −0.014 (3) | 0.093 (7) |
F5 | 0.058 (4) | 0.296 (12) | 0.135 (6) | 0.004 (5) | 0.012 (4) | −0.064 (7) |
F6 | 0.102 (6) | 0.124 (7) | 0.323 (14) | −0.062 (5) | −0.036 (7) | 0.040 (8) |
F7 | 0.132 (6) | 0.137 (6) | 0.139 (6) | 0.033 (5) | 0.086 (5) | 0.067 (5) |
F8 | 0.268 (11) | 0.096 (5) | 0.188 (8) | −0.078 (6) | 0.125 (8) | 0.002 (5) |
F9 | 0.133 (6) | 0.246 (10) | 0.106 (5) | 0.033 (6) | 0.040 (5) | 0.113 (6) |
F10 | 0.086 (4) | 0.109 (4) | 0.079 (4) | −0.017 (4) | −0.017 (3) | −0.011 (3) |
F11 | 0.087 (4) | 0.109 (4) | 0.072 (3) | 0.032 (3) | −0.013 (3) | 0.006 (3) |
F12 | 0.084 (4) | 0.202 (7) | 0.043 (3) | 0.021 (4) | 0.008 (3) | −0.012 (3) |
Gd1 | 0.03767 (18) | 0.04414 (19) | 0.03731 (17) | 0.00276 (16) | 0.00926 (12) | 0.00810 (15) |
N1 | 0.087 (6) | 0.085 (6) | 0.104 (7) | −0.003 (5) | −0.006 (5) | −0.013 (5) |
N2 | 0.108 (7) | 0.063 (5) | 0.046 (4) | −0.012 (5) | 0.000 (4) | 0.007 (3) |
O1 | 0.041 (3) | 0.058 (3) | 0.055 (3) | −0.005 (2) | 0.005 (2) | 0.014 (2) |
O2 | 0.045 (3) | 0.058 (3) | 0.063 (3) | 0.003 (2) | 0.008 (2) | 0.026 (3) |
O3 | 0.045 (3) | 0.102 (4) | 0.039 (3) | 0.005 (3) | 0.007 (2) | 0.001 (3) |
O4 | 0.052 (3) | 0.071 (3) | 0.045 (3) | −0.017 (3) | 0.009 (2) | 0.011 (2) |
O5 | 0.045 (3) | 0.061 (3) | 0.055 (3) | 0.019 (2) | 0.021 (2) | 0.017 (2) |
O6 | 0.047 (3) | 0.049 (3) | 0.053 (3) | 0.002 (2) | 0.016 (2) | 0.013 (2) |
O7 | 0.033 (2) | 0.068 (3) | 0.037 (2) | 0.008 (2) | 0.0113 (19) | 0.000 (2) |
O8 | 0.039 (3) | 0.066 (3) | 0.050 (3) | 0.015 (2) | 0.013 (2) | 0.011 (2) |
S1 | 0.0607 (15) | 0.105 (2) | 0.107 (2) | 0.0156 (14) | 0.0109 (14) | 0.0301 (16) |
S3 | 0.0507 (12) | 0.0977 (19) | 0.0861 (16) | 0.0040 (12) | 0.0097 (11) | −0.0017 (14) |
S2—C44 | 1.6 (2) | C14—H14 | 0.9300 |
S2—C41 | 1.65 (6) | C15—H15 | 0.9300 |
C41—C42 | 1.40 (12) | C16—N2 | 1.489 (12) |
C41—H41 | 0.9300 | C16—H16A | 0.9600 |
C42—C43 | 1.46 (11) | C16—H16B | 0.9600 |
C42—H42 | 0.9300 | C16—H16C | 0.9600 |
C43—C44 | 1.4 (2) | C17—C18 | 1.332 (15) |
C43—H43 | 0.9300 | C17—S1 | 1.693 (10) |
C44—C45 | 1.51 (19) | C17—H17 | 0.9300 |
S2'—C41' | 1.5 (2) | C18—C19 | 1.377 (13) |
S2'—C44' | 1.7 (5) | C18—H18 | 0.9300 |
C42'—C41' | 1.4 (2) | C19—C20 | 1.441 (10) |
C42'—C43' | 1.48 (17) | C19—H19 | 0.9300 |
C42'—H42' | 0.9300 | C20—C21 | 1.477 (10) |
C41'—H41' | 0.9300 | C20—S1 | 1.694 (8) |
C43'—C44' | 1.5 (4) | C21—O2 | 1.253 (8) |
C43'—H43' | 0.9300 | C21—C22 | 1.405 (10) |
C44'—C45 | 1.4 (4) | C22—C23 | 1.366 (10) |
S4—C36 | 1.68 (11) | C22—H22 | 0.9300 |
S4—C33 | 1.68 (7) | C23—O1 | 1.276 (8) |
C33—C34 | 1.42 (6) | C23—C24 | 1.532 (11) |
C33—H33 | 0.9300 | C24—F1 | 1.314 (10) |
C34—C35 | 1.45 (11) | C24—F2 | 1.316 (11) |
C34—H34 | 0.9300 | C24—F3 | 1.323 (11) |
C35—C36 | 1.44 (12) | C25—C26 | 1.339 (13) |
C35—H35 | 0.9300 | C25—S3 | 1.697 (9) |
C36—C37 | 1.48 (8) | C25—H25 | 0.9300 |
S4'—C33' | 1.65 (10) | C26—C27 | 1.430 (12) |
S4'—C36' | 1.66 (17) | C26—H26 | 0.9300 |
C34'—C33' | 1.44 (12) | C27—C28 | 1.446 (10) |
C34'—C35' | 1.5 (2) | C27—H27 | 0.9300 |
C34'—H34' | 0.9300 | C28—C29 | 1.467 (9) |
C33'—H33' | 0.9300 | C28—S3 | 1.704 (8) |
C35'—C36' | 1.4 (3) | C29—O8 | 1.249 (8) |
C35'—H35' | 0.9300 | C29—C30 | 1.421 (9) |
C36'—C37 | 1.43 (18) | C30—C31 | 1.354 (10) |
C1—N1 | 1.451 (13) | C30—H30 | 0.9300 |
C1—H1A | 0.9600 | C31—O7 | 1.261 (7) |
C1—H1B | 0.9600 | C31—C32 | 1.546 (10) |
C1—H1C | 0.9600 | C32—F12 | 1.331 (9) |
C2—N1 | 1.427 (13) | C32—F11 | 1.333 (10) |
C2—H2A | 0.9600 | C32—F10 | 1.346 (11) |
C2—H2B | 0.9600 | C37—O5 | 1.256 (8) |
C2—H2C | 0.9600 | C37—C38 | 1.422 (10) |
C3—N1 | 1.358 (12) | C38—C39 | 1.360 (10) |
C3—C4 | 1.403 (14) | C38—H38 | 0.9300 |
C3—C8 | 1.419 (14) | C39—O6 | 1.260 (8) |
C4—C5 | 1.394 (15) | C39—C40 | 1.541 (12) |
C4—H4 | 0.9300 | C40—F8 | 1.297 (13) |
C5—C6 | 1.367 (14) | C40—F9 | 1.297 (12) |
C5—H5 | 0.9300 | C40—F7 | 1.306 (11) |
C6—C7 | 1.382 (13) | C45—O3 | 1.249 (8) |
C6—C9 | 1.491 (14) | C45—C46 | 1.400 (10) |
C7—C8 | 1.360 (13) | C46—C47 | 1.384 (10) |
C7—H7 | 0.9300 | C46—H46 | 0.9300 |
C8—H8 | 0.9300 | C47—O4 | 1.261 (8) |
C9—C10 | 1.294 (13) | C47—C48 | 1.503 (11) |
C9—H9 | 0.9300 | C48—F4 | 1.269 (10) |
C10—C11 | 1.464 (14) | C48—F6 | 1.269 (11) |
C10—H10 | 0.9300 | C48—F5 | 1.296 (11) |
C11—C12 | 1.396 (14) | Gd1—O3 | 2.366 (5) |
C11—C15 | 1.403 (12) | Gd1—O8 | 2.373 (5) |
C12—C13 | 1.350 (14) | Gd1—O6 | 2.375 (4) |
C12—H12 | 0.9300 | Gd1—O5 | 2.375 (4) |
C13—N2 | 1.351 (12) | Gd1—O1 | 2.382 (5) |
C13—H13 | 0.9300 | Gd1—O4 | 2.391 (5) |
C14—C15 | 1.357 (13) | Gd1—O2 | 2.400 (5) |
C14—N2 | 1.365 (12) | Gd1—O7 | 2.419 (4) |
C44—S2—C41 | 94 (8) | O2—C21—C20 | 116.4 (7) |
C42—C41—S2 | 113 (5) | C22—C21—C20 | 120.2 (6) |
C42—C41—H41 | 123.3 | C23—C22—C21 | 122.6 (7) |
S2—C41—H41 | 123.3 | C23—C22—H22 | 118.7 |
C41—C42—C43 | 109 (7) | C21—C22—H22 | 118.7 |
C41—C42—H42 | 125.6 | O1—C23—C22 | 128.8 (7) |
C43—C42—H42 | 125.6 | O1—C23—C24 | 112.6 (7) |
C44—C43—C42 | 111 (10) | C22—C23—C24 | 118.4 (7) |
C44—C43—H43 | 124.6 | F1—C24—F2 | 108.3 (8) |
C42—C43—H43 | 124.6 | F1—C24—F3 | 105.6 (9) |
C43—C44—C45 | 128 (10) | F2—C24—F3 | 105.0 (8) |
C43—C44—S2 | 113 (10) | F1—C24—C23 | 114.3 (8) |
C45—C44—S2 | 119 (10) | F2—C24—C23 | 111.0 (8) |
C41'—S2'—C44' | 99 (10) | F3—C24—C23 | 112.0 (7) |
C41'—C42'—C43' | 110 (10) | C26—C25—S3 | 112.5 (7) |
C41'—C42'—H42' | 124.0 | C26—C25—H25 | 123.7 |
C43'—C42'—H42' | 125.1 | S3—C25—H25 | 123.7 |
C42'—C41'—S2' | 117 (10) | C25—C26—C27 | 116.1 (8) |
C42'—C41'—H41' | 121.5 | C25—C26—H26 | 122.0 |
S2'—C41'—H41' | 121.5 | C27—C26—H26 | 122.0 |
C42'—C43'—C44' | 105 (10) | C26—C27—C28 | 106.6 (8) |
C42'—C43'—H43' | 127.3 | C26—C27—H27 | 126.7 |
C44'—C43'—H43' | 130.0 | C28—C27—H27 | 126.7 |
C43'—C44'—S2' | 111 (10) | C27—C28—C29 | 128.3 (7) |
C36—S4—C33 | 90 (4) | C27—C28—S3 | 113.2 (5) |
C34—C33—S4 | 114 (5) | C29—C28—S3 | 118.4 (5) |
C34—C33—H33 | 124.0 | O8—C29—C30 | 123.2 (6) |
S4—C33—H33 | 122.8 | O8—C29—C28 | 116.8 (6) |
C33—C34—C35 | 112 (6) | C30—C29—C28 | 119.9 (6) |
C33—C34—H34 | 124.0 | C31—C30—C29 | 121.2 (6) |
C35—C34—H34 | 124.0 | C31—C30—H30 | 119.4 |
C36—C35—C34 | 106 (7) | C29—C30—H30 | 119.4 |
C36—C35—H35 | 127.0 | O7—C31—C30 | 130.6 (6) |
C34—C35—H35 | 127.0 | O7—C31—C32 | 111.5 (6) |
C35—C36—C37 | 124 (9) | C30—C31—C32 | 117.8 (6) |
C35—C36—S4 | 117 (7) | F12—C32—F11 | 107.9 (7) |
C37—C36—S4 | 118 (6) | F12—C32—F10 | 105.7 (8) |
C33'—S4'—C36' | 96 (9) | F11—C32—F10 | 105.5 (7) |
C33'—C34'—C35' | 97 (10) | F12—C32—C31 | 114.2 (7) |
C33'—C34'—H34' | 131.4 | F11—C32—C31 | 111.3 (7) |
C35'—C34'—H34' | 131.5 | F10—C32—C31 | 111.7 (7) |
C34'—C33'—S4' | 117 (10) | O5—C37—C38 | 123.2 (7) |
C34'—C33'—H33' | 121.3 | O5—C37—C36' | 116 (8) |
S4'—C33'—H33' | 121.3 | C38—C37—C36' | 121 (8) |
C36'—C35'—C34' | 125 (10) | O5—C37—C36 | 117 (4) |
C36'—C35'—H35' | 117.5 | C38—C37—C36 | 120 (4) |
C34'—C35'—H35' | 117.5 | C39—C38—C37 | 122.4 (7) |
C35'—C36'—C37 | 125 (10) | C39—C38—H38 | 118.8 |
C35'—C36'—S4' | 104 (10) | C37—C38—H38 | 118.8 |
C37—C36'—S4' | 131 (10) | O6—C39—C38 | 129.1 (7) |
N1—C1—H1A | 109.5 | O6—C39—C40 | 112.9 (7) |
N1—C1—H1B | 109.5 | C38—C39—C40 | 117.8 (7) |
H1A—C1—H1B | 109.5 | F8—C40—F9 | 108.2 (10) |
N1—C1—H1C | 109.5 | F8—C40—F7 | 104.5 (11) |
H1A—C1—H1C | 109.5 | F9—C40—F7 | 105.8 (9) |
H1B—C1—H1C | 109.5 | F8—C40—C39 | 111.7 (9) |
N1—C2—H2A | 109.5 | F9—C40—C39 | 113.9 (10) |
N1—C2—H2B | 109.5 | F7—C40—C39 | 112.1 (8) |
H2A—C2—H2B | 109.5 | O3—C45—C44' | 118 (10) |
N1—C2—H2C | 109.5 | O3—C45—C46 | 123.3 (7) |
H2A—C2—H2C | 109.5 | C44'—C45—C46 | 119 (10) |
H2B—C2—H2C | 109.5 | O3—C45—C44 | 113 (9) |
N1—C3—C4 | 122.4 (10) | C46—C45—C44 | 123 (9) |
N1—C3—C8 | 122.7 (9) | C47—C46—C45 | 122.7 (7) |
C4—C3—C8 | 114.9 (10) | C47—C46—H46 | 118.6 |
C5—C4—C3 | 120.4 (10) | C45—C46—H46 | 118.6 |
C5—C4—H4 | 119.8 | O4—C47—C46 | 128.0 (7) |
C3—C4—H4 | 119.8 | O4—C47—C48 | 114.9 (7) |
C6—C5—C4 | 124.3 (10) | C46—C47—C48 | 117.1 (7) |
C6—C5—H5 | 117.8 | F4—C48—F6 | 106.4 (10) |
C4—C5—H5 | 117.8 | F4—C48—F5 | 106.6 (10) |
C5—C6—C7 | 114.8 (10) | F6—C48—F5 | 100.1 (9) |
C5—C6—C9 | 124.7 (10) | F4—C48—C47 | 116.6 (7) |
C7—C6—C9 | 120.4 (10) | F6—C48—C47 | 112.3 (9) |
C8—C7—C6 | 123.4 (10) | F5—C48—C47 | 113.4 (8) |
C8—C7—H7 | 118.3 | O3—Gd1—O8 | 145.78 (17) |
C6—C7—H7 | 118.3 | O3—Gd1—O6 | 113.47 (19) |
C7—C8—C3 | 122.1 (10) | O8—Gd1—O6 | 78.58 (16) |
C7—C8—H8 | 119.0 | O3—Gd1—O5 | 72.66 (17) |
C3—C8—H8 | 119.0 | O8—Gd1—O5 | 139.85 (16) |
C10—C9—C6 | 125.6 (10) | O6—Gd1—O5 | 71.39 (16) |
C10—C9—H9 | 117.2 | O3—Gd1—O1 | 76.16 (19) |
C6—C9—H9 | 117.2 | O8—Gd1—O1 | 111.65 (18) |
C9—C10—C11 | 122.7 (10) | O6—Gd1—O1 | 147.37 (16) |
C9—C10—H10 | 118.7 | O5—Gd1—O1 | 83.11 (17) |
C11—C10—H10 | 118.7 | O3—Gd1—O4 | 70.91 (17) |
C12—C11—C15 | 116.0 (10) | O8—Gd1—O4 | 81.99 (18) |
C12—C11—C10 | 118.3 (9) | O6—Gd1—O4 | 76.49 (17) |
C15—C11—C10 | 125.7 (10) | O5—Gd1—O4 | 114.97 (19) |
C13—C12—C11 | 120.9 (9) | O1—Gd1—O4 | 134.31 (16) |
C13—C12—H12 | 119.5 | O3—Gd1—O2 | 83.09 (18) |
C11—C12—H12 | 119.5 | O8—Gd1—O2 | 69.56 (16) |
C12—C13—N2 | 120.7 (10) | O6—Gd1—O2 | 139.31 (16) |
C12—C13—H13 | 119.6 | O5—Gd1—O2 | 147.91 (16) |
N2—C13—H13 | 119.6 | O1—Gd1—O2 | 70.68 (16) |
C15—C14—N2 | 117.8 (9) | O4—Gd1—O2 | 74.64 (17) |
C15—C14—H14 | 121.1 | O3—Gd1—O7 | 142.07 (16) |
N2—C14—H14 | 121.1 | O8—Gd1—O7 | 70.05 (15) |
C14—C15—C11 | 122.8 (10) | O6—Gd1—O7 | 78.17 (17) |
C14—C15—H15 | 118.6 | O5—Gd1—O7 | 78.07 (16) |
C11—C15—H15 | 118.6 | O1—Gd1—O7 | 76.86 (16) |
N2—C16—H16A | 109.5 | O4—Gd1—O7 | 145.33 (15) |
N2—C16—H16B | 109.5 | O2—Gd1—O7 | 112.17 (17) |
H16A—C16—H16B | 109.5 | C3—N1—C2 | 121.7 (9) |
N2—C16—H16C | 109.5 | C3—N1—C1 | 120.3 (9) |
H16A—C16—H16C | 109.5 | C2—N1—C1 | 117.8 (10) |
H16B—C16—H16C | 109.5 | C13—N2—C14 | 121.5 (9) |
C18—C17—S1 | 111.9 (8) | C13—N2—C16 | 119.2 (9) |
C18—C17—H17 | 124.1 | C14—N2—C16 | 119.3 (8) |
S1—C17—H17 | 124.1 | C23—O1—Gd1 | 130.2 (4) |
C17—C18—C19 | 116.2 (9) | C21—O2—Gd1 | 136.1 (5) |
C17—C18—H18 | 121.9 | C45—O3—Gd1 | 135.7 (5) |
C19—C18—H18 | 121.9 | C47—O4—Gd1 | 128.7 (4) |
C18—C19—C20 | 108.7 (8) | C37—O5—Gd1 | 136.1 (5) |
C18—C19—H19 | 125.7 | C39—O6—Gd1 | 130.1 (5) |
C20—C19—H19 | 125.7 | C31—O7—Gd1 | 129.0 (4) |
C19—C20—C21 | 130.3 (7) | C29—O8—Gd1 | 133.5 (4) |
C19—C20—S1 | 111.4 (6) | C17—S1—C20 | 91.8 (5) |
C21—C20—S1 | 118.3 (6) | C25—S3—C28 | 91.6 (5) |
O2—C21—C22 | 123.4 (7) |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (grant No. 21071001), the Education Committee of Anhui Province (grant No. KJ2010A030), the Natural Science Foundation of Anhui Province (grant No. 1208085MB22).
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