Bis[2-(2-pyridylmethyl­eneamino)benzene­sulfonato-κ3N,N′,O]manganese(II) dihydrate

Zhao, C.-Q.; Ou-Yang, M.; Huang, X.-R.; Jiang, Y.-M.

doi:10.1107/S1600536809030670

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1055-m1056

doi:10.1107/S1600536809030670

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Bis[2-(2-pyridylmethyleneamino)benzenesulfonato-κ³N,N′,O]manganese(II) dihydrate

Cheng-Qiang Zhao,^a,^b Miao Ou-Yang,^c Xue-Ren Huang ^a and Yi-Min Jiang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, Guangxi 541004, People's Republic of China, ^bDepartment of Chemistry and Life Science, Hechi University, Yizhou, Guangxi 546300, People's Republic of China, and ^cLeizhou No. 1 Middle School, Leizhou, Guangdong 524200, People's Republic of China
^*Correspondence e-mail: 442976264@qq.com

(Received 26 June 2009; accepted 2 August 2009; online 8 August 2009)

The title complex, [Mn(C₁₂H₉N₂O₃S)₂]·2H₂O, is isotypic with the previously reported Zn^II and Cd^II species. The complex was prepared by the reaction of the potassium salt of 2-(2-pyridylmethyleneamino)benzenesulfonic acid with MnCl₂·6H₂O in methanol. The complex displays twofold symmetry, with the ligands coordinated in a tridentate meridional-like arrangement through pyridyl N, imine N, and sulfonate O atoms. The metal center has a strongly distorted octahedral coordination geometry. The uncoordinated water molecules and the complexes participate in a hydrogen-bonding network, forming a two-dimensional structure parallel to the ab plane.

Related literature

For the synthesis of the ligand, see: Casella & Gullotti (1986 ). For the structures of the Zn^II and Cd^II analogues, see: Cai et al. (2008 ); Ou-Yang et al. (2008 ). For related Schiff bases complexes, see: Correia et al. (2003 ); Li et al. (2007 , 2008 ); Ou-Yang et al. (2009 ); Zhang et al. (2005 ).

Experimental

Crystal data

[Mn(C₁₂H₉N₂O₃S)₂]·2H₂O
M_r = 613.52
Orthorhombic, P b c n
a = 20.041 (10) Å
b = 7.918 (4) Å
c = 16.409 (8) Å
V = 2604 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 296 K
0.49 × 0.34 × 0.21 mm

Data collection

SMART APEX CCD diffractometer
Absorption correction: none
13313 measured reflections
2320 independent reflections
1950 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.01
2320 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1W⋯O3ⁱ	0.85	2.14	2.993 (3)	179
O4—H2W⋯O2	0.84	2.11	2.866 (3)	151
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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/S1600536809030670/bh2236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030670/bh2236Isup2.hkl

checkCIF report

Comment top

In the past decades, Schiff-base complexes containing sulfonate have received much attention owing to the diverse coordination modes and bridging ability (Zhang et al., 2005; Li et al., 2007; Ou-Yang et al., 2009). Herein, we prepared a mononuclear Mn(II) complex, which is isostructural with [Zn(Paba)₂].2 H₂O and [Cd(Paba)₂].2 H₂O, whose structures were described in details (Cai et al., 2008; Ou-Yang et al., 2008). The six-coordinated Mn^II ion lies on a twofold axis, and two deprotonated PabaH anions coordinate to Mn in a meridional arrangement as N,N',O-tridentate donor ligands. The coordination mode of the complex is similar to that observed in other complexes with N,N',O-tridentate donor ligands (Li et al., 2007, 2008; Correia et al., 2003).

The O—H donor groups from the lattice water molecules and the SO acceptor groups of the Paba ligands participate in the hydrogen bonding through which the complex completes a two-dimensional network parallel to the ab plane (Fig. 2).

Related literature top

For the synthesis of the ligand, see: Casella & Gullotti (1986). For the structures of the Zn^II and Cd^II analogues, see: Cai et al. (2008); Ou-Yang et al. (2008). For related Schiff bases complexes, see: Correia et al. (2003); Li et al. (2007, 2008); Ou-Yang et al. (2009); Zhang et al. (2005).

Experimental top

The potassium salt of 2-(2-pyridylmethyleneamino)benzenesulfonic acid (PabaK) was synthesized according to the literature methods (Casella & Gullotti, 1986). The ligand PabaK (1 mmol, 0.30 g) was dissolved in methanol (10 ml). To this solution, MnCl₂ 6 H₂O (0.5 mmol, 0.12 g) was added, and the resulting mixture was stirred at 333 K for 4 h. Then the mixture was filtrated and the filtrate was left to stand at room temperature. Yellow crystals suitable for X-ray diffraction were obtained after a week in a yield of 55%. Elemental analysis: found C 46.87, H 4.04, N 9.05, S 10.42%; calc. C 46.94, H 3.59, N 9.13, S 10.43%.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 the title complex, showing the atom-numbering scheme. The water molecule and all H atoms have been omitted for clarity. Symmetry code for 'A' labelled atoms: 2 - x, y, 1/2 - z.
	Fig. 2. Packing of the title complex, showing the two-dimensional network in the ab plane, linked via hydrogen bonds (dashed lines).

Bis[2-(2-pyridylmethyleneamino)benzenesulfonato-κ³N,N',O]manganese(II) dihydrate top

Crystal data top

[Mn(C₁₂H₉N₂O₃S)₂]·2H₂O	F(000) = 1260
M_r = 613.52	D_x = 1.565 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4677 reflections
a = 20.041 (10) Å	θ = 2.5–28.5°
b = 7.918 (4) Å	µ = 0.72 mm⁻¹
c = 16.409 (8) Å	T = 296 K
V = 2604 (2) Å³	Block, yellow
Z = 4	0.49 × 0.34 × 0.21 mm

Data collection top

SMART APEX CCD diffractometer	1950 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 25.1°, θ_min = 2.5°
ϕ and ω scans	h = −21→23
13313 measured reflections	k = −9→9
2320 independent reflections	l = −19→19

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) = 0.092	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0512P)² + 1.5899P] where P = (F_o² + 2F_c²)/3
2320 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Mn(C₁₂H₉N₂O₃S)₂]·2H₂O	V = 2604 (2) Å³
M_r = 613.52	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 20.041 (10) Å	µ = 0.72 mm⁻¹
b = 7.918 (4) Å	T = 296 K
c = 16.409 (8) Å	0.49 × 0.34 × 0.21 mm

Data collection top

SMART APEX CCD diffractometer	1950 reflections with I > 2σ(I)
13313 measured reflections	R_int = 0.028
2320 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.01	Δρ_max = 0.47 e Å⁻³
2320 reflections	Δρ_min = −0.41 e Å⁻³
177 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mn1	1.0000	0.18060 (6)	0.2500	0.02835 (15)
S1	0.87380 (3)	0.32706 (7)	0.33859 (3)	0.03333 (17)
O1	0.94725 (8)	0.3323 (2)	0.33645 (9)	0.0381 (4)
O2	0.84921 (9)	0.1575 (2)	0.32866 (10)	0.0508 (5)
O3	0.84826 (8)	0.4155 (2)	0.40879 (9)	0.0466 (4)
N1	0.99221 (9)	−0.0275 (2)	0.15711 (11)	0.0352 (4)
N2	0.90694 (8)	0.2347 (2)	0.16781 (10)	0.0303 (4)
C1	1.03597 (13)	−0.1521 (3)	0.14852 (14)	0.0444 (6)
H1	1.0708	−0.1601	0.1858	0.053*
C2	1.03222 (15)	−0.2704 (3)	0.08686 (15)	0.0495 (6)
H2	1.0641	−0.3553	0.0826	0.059*
C3	0.98074 (14)	−0.2607 (3)	0.03207 (16)	0.0503 (6)
H3	0.9767	−0.3399	−0.0095	0.060*
C4	0.93496 (13)	−0.1310 (3)	0.03971 (14)	0.0440 (6)
H4	0.8998	−0.1210	0.0031	0.053*
C5	0.94222 (11)	−0.0165 (3)	0.10256 (12)	0.0329 (5)
C6	0.89698 (11)	0.1272 (3)	0.11156 (13)	0.0360 (5)
H6	0.8610	0.1400	0.0762	0.043*
C7	0.86610 (10)	0.3806 (3)	0.17345 (12)	0.0321 (5)
C8	0.84533 (12)	0.4702 (3)	0.10524 (14)	0.0440 (6)
H8	0.8560	0.4311	0.0534	0.053*
C9	0.80902 (13)	0.6167 (4)	0.11399 (15)	0.0536 (7)
H9	0.7950	0.6754	0.0680	0.064*
C10	0.79326 (14)	0.6770 (4)	0.19056 (17)	0.0542 (7)
H10	0.7695	0.7772	0.1960	0.065*
C11	0.81279 (12)	0.5887 (3)	0.25907 (14)	0.0432 (6)
H11	0.8014	0.6283	0.3106	0.052*
C12	0.84920 (10)	0.4420 (3)	0.25118 (11)	0.0319 (5)
O4	0.79877 (12)	−0.0889 (4)	0.44087 (15)	0.1140 (12)
H1W	0.7570	−0.0869	0.4320	0.171*
H2W	0.8166	−0.0498	0.3988	0.171*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0279 (3)	0.0336 (3)	0.0235 (2)	0.000	−0.00482 (17)	0.000
S1	0.0326 (3)	0.0437 (3)	0.0236 (3)	0.0002 (2)	0.0001 (2)	0.0008 (2)
O1	0.0316 (8)	0.0540 (10)	0.0287 (8)	0.0050 (7)	−0.0044 (6)	−0.0070 (7)
O2	0.0606 (12)	0.0486 (11)	0.0431 (10)	−0.0120 (9)	−0.0038 (8)	0.0083 (8)
O3	0.0434 (9)	0.0699 (12)	0.0267 (8)	0.0085 (8)	0.0051 (7)	−0.0043 (8)
N1	0.0409 (10)	0.0350 (10)	0.0297 (9)	0.0024 (8)	−0.0067 (8)	−0.0015 (8)
N2	0.0280 (9)	0.0384 (10)	0.0245 (8)	0.0003 (8)	−0.0007 (7)	−0.0004 (7)
C1	0.0503 (15)	0.0428 (14)	0.0401 (13)	0.0087 (12)	−0.0108 (11)	−0.0008 (10)
C2	0.0684 (17)	0.0356 (13)	0.0445 (14)	0.0116 (12)	−0.0024 (13)	−0.0030 (11)
C3	0.0721 (18)	0.0382 (13)	0.0406 (13)	0.0020 (13)	−0.0054 (13)	−0.0095 (11)
C4	0.0510 (15)	0.0466 (14)	0.0345 (12)	−0.0044 (11)	−0.0110 (11)	−0.0076 (10)
C5	0.0350 (11)	0.0369 (12)	0.0269 (10)	−0.0033 (9)	−0.0028 (9)	−0.0003 (9)
C6	0.0318 (11)	0.0488 (13)	0.0273 (11)	−0.0008 (10)	−0.0067 (9)	−0.0017 (10)
C7	0.0243 (11)	0.0435 (13)	0.0284 (10)	0.0018 (9)	−0.0006 (8)	0.0017 (9)
C8	0.0398 (13)	0.0621 (16)	0.0302 (11)	0.0098 (12)	0.0019 (10)	0.0066 (11)
C9	0.0495 (15)	0.0690 (18)	0.0421 (14)	0.0200 (14)	0.0001 (12)	0.0159 (13)
C10	0.0497 (16)	0.0556 (17)	0.0574 (16)	0.0213 (13)	0.0015 (13)	0.0089 (13)
C11	0.0380 (13)	0.0517 (15)	0.0398 (13)	0.0107 (11)	0.0045 (10)	−0.0024 (11)
C12	0.0257 (11)	0.0415 (12)	0.0284 (11)	−0.0003 (9)	0.0002 (8)	0.0014 (9)
O4	0.0640 (15)	0.182 (3)	0.0956 (19)	−0.0353 (17)	−0.0233 (13)	0.075 (2)

Geometric parameters (Å, º) top

Mn1—O1	2.1382 (16)	C3—C4	1.383 (4)
Mn1—O1ⁱ	2.1382 (16)	C3—H3	0.9300
Mn1—N1	2.250 (2)	C4—C5	1.381 (3)
Mn1—N1ⁱ	2.250 (2)	C4—H4	0.9300
Mn1—N2ⁱ	2.3412 (19)	C5—C6	1.463 (3)
Mn1—N2	2.3412 (19)	C6—H6	0.9300
S1—O2	1.4395 (19)	C7—C8	1.389 (3)
S1—O3	1.4420 (17)	C7—C12	1.406 (3)
S1—O1	1.4729 (18)	C8—C9	1.376 (4)
S1—C12	1.769 (2)	C8—H8	0.9300
N1—C1	1.327 (3)	C9—C10	1.381 (4)
N1—C5	1.346 (3)	C9—H9	0.9300
N2—C6	1.271 (3)	C10—C11	1.380 (3)
N2—C7	1.418 (3)	C10—H10	0.9300
C1—C2	1.381 (3)	C11—C12	1.378 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.371 (4)	O4—H1W	0.8495
C2—H2	0.9300	O4—H2W	0.8364

O1—Mn1—O1ⁱ	111.67 (10)	C1—C2—H2	120.6
O1—Mn1—N1	145.73 (6)	C2—C3—C4	118.8 (2)
O1ⁱ—Mn1—N1	89.79 (7)	C2—C3—H3	120.6
O1—Mn1—N1ⁱ	89.79 (7)	C4—C3—H3	120.6
O1ⁱ—Mn1—N1ⁱ	145.73 (6)	C5—C4—C3	119.0 (2)
N1—Mn1—N1ⁱ	85.83 (10)	C5—C4—H4	120.5
O1—Mn1—N2ⁱ	84.77 (6)	C3—C4—H4	120.5
O1ⁱ—Mn1—N2ⁱ	83.42 (7)	N1—C5—C4	122.2 (2)
N1—Mn1—N2ⁱ	125.42 (7)	N1—C5—C6	116.40 (18)
N1ⁱ—Mn1—N2ⁱ	71.86 (7)	C4—C5—C6	121.4 (2)
O1—Mn1—N2	83.42 (6)	N2—C6—C5	119.80 (19)
O1ⁱ—Mn1—N2	84.77 (6)	N2—C6—H6	120.1
N1—Mn1—N2	71.86 (7)	C5—C6—H6	120.1
N1ⁱ—Mn1—N2	125.42 (7)	C8—C7—C12	118.8 (2)
N2ⁱ—Mn1—N2	158.90 (9)	C8—C7—N2	122.43 (19)
O2—S1—O3	114.95 (11)	C12—C7—N2	118.65 (18)
O2—S1—O1	111.44 (11)	C9—C8—C7	120.3 (2)
O3—S1—O1	111.11 (9)	C9—C8—H8	119.8
O2—S1—C12	107.02 (10)	C7—C8—H8	119.8
O3—S1—C12	107.40 (11)	C8—C9—C10	120.5 (2)
O1—S1—C12	104.18 (9)	C8—C9—H9	119.8
S1—O1—Mn1	119.62 (9)	C10—C9—H9	119.8
C1—N1—C5	117.98 (19)	C11—C10—C9	120.1 (2)
C1—N1—Mn1	124.77 (15)	C11—C10—H10	120.0
C5—N1—Mn1	117.04 (14)	C9—C10—H10	120.0
C6—N2—C7	120.13 (18)	C12—C11—C10	120.0 (2)
C6—N2—Mn1	114.88 (15)	C12—C11—H11	120.0
C7—N2—Mn1	124.83 (13)	C10—C11—H11	120.0
N1—C1—C2	123.1 (2)	C11—C12—C7	120.3 (2)
N1—C1—H1	118.5	C11—C12—S1	120.34 (16)
C2—C1—H1	118.5	C7—C12—S1	119.38 (17)
C3—C2—C1	118.9 (2)	H1W—O4—H2W	105.8
C3—C2—H2	120.6

O2—S1—O1—Mn1	41.05 (13)	C2—C3—C4—C5	−0.5 (4)
O3—S1—O1—Mn1	170.64 (10)	C1—N1—C5—C4	0.9 (3)
C12—S1—O1—Mn1	−74.01 (13)	Mn1—N1—C5—C4	175.90 (17)
O1ⁱ—Mn1—O1—S1	115.14 (11)	C1—N1—C5—C6	−177.0 (2)
N1—Mn1—O1—S1	−10.02 (18)	Mn1—N1—C5—C6	−2.0 (2)
N1ⁱ—Mn1—O1—S1	−92.28 (11)	C3—C4—C5—N1	−0.5 (4)
N2ⁱ—Mn1—O1—S1	−164.08 (11)	C3—C4—C5—C6	177.4 (2)
N2—Mn1—O1—S1	33.44 (10)	C7—N2—C6—C5	175.63 (19)
O1—Mn1—N1—C1	−137.89 (18)	Mn1—N2—C6—C5	0.1 (3)
O1ⁱ—Mn1—N1—C1	91.6 (2)	N1—C5—C6—N2	1.3 (3)
N1ⁱ—Mn1—N1—C1	−54.42 (17)	C4—C5—C6—N2	−176.7 (2)
N2ⁱ—Mn1—N1—C1	9.8 (2)	C6—N2—C7—C8	−40.0 (3)
N2—Mn1—N1—C1	176.1 (2)	Mn1—N2—C7—C8	135.02 (19)
O1—Mn1—N1—C5	47.5 (2)	C6—N2—C7—C12	143.7 (2)
O1ⁱ—Mn1—N1—C5	−83.05 (16)	Mn1—N2—C7—C12	−41.3 (3)
N1ⁱ—Mn1—N1—C5	130.97 (18)	C12—C7—C8—C9	0.2 (4)
N2ⁱ—Mn1—N1—C5	−164.81 (14)	N2—C7—C8—C9	−176.1 (2)
N2—Mn1—N1—C5	1.52 (15)	C7—C8—C9—C10	0.5 (4)
O1—Mn1—N2—C6	−156.78 (16)	C8—C9—C10—C11	−1.3 (4)
O1ⁱ—Mn1—N2—C6	90.65 (16)	C9—C10—C11—C12	1.3 (4)
N1—Mn1—N2—C6	−0.84 (15)	C10—C11—C12—C7	−0.6 (4)
N1ⁱ—Mn1—N2—C6	−71.75 (17)	C10—C11—C12—S1	−179.4 (2)
N2ⁱ—Mn1—N2—C6	146.83 (16)	C8—C7—C12—C11	−0.1 (3)
O1—Mn1—N2—C7	27.95 (16)	N2—C7—C12—C11	176.3 (2)
O1ⁱ—Mn1—N2—C7	−84.62 (16)	C8—C7—C12—S1	178.73 (17)
N1—Mn1—N2—C7	−176.11 (17)	N2—C7—C12—S1	−4.8 (3)
N1ⁱ—Mn1—N2—C7	112.98 (16)	O2—S1—C12—C11	124.5 (2)
N2ⁱ—Mn1—N2—C7	−28.44 (15)	O3—S1—C12—C11	0.6 (2)
C5—N1—C1—C2	−0.4 (4)	O1—S1—C12—C11	−117.32 (19)
Mn1—N1—C1—C2	−174.95 (19)	O2—S1—C12—C7	−54.3 (2)
N1—C1—C2—C3	−0.6 (4)	O3—S1—C12—C7	−178.25 (17)
C1—C2—C3—C4	1.0 (4)	O1—S1—C12—C7	63.82 (19)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1W···O3ⁱⁱ	0.85	2.14	2.993 (3)	179
O4—H2W···O2	0.84	2.11	2.866 (3)	151

Symmetry code: (ii) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₂H₉N₂O₃S)₂]·2H₂O
M_r	613.52
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	296
a, b, c (Å)	20.041 (10), 7.918 (4), 16.409 (8)
V (Å³)	2604 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.49 × 0.34 × 0.21

Data collection
Diffractometer	SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13313, 2320, 1950
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.01
No. of reflections	2320
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.41

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1W···O3ⁱ	0.85	2.14	2.993 (3)	179.3
O4—H2W···O2	0.84	2.11	2.866 (3)	150.6

Symmetry code: (i) −x+3/2, y−1/2, z.

Acknowledgements

This work was funded by the Guangxi Science Foundation of the Guangxi Zhuang Autonomous Region of the People's Republic of China (grant No. 0731053).

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