Bis[2,4-penta­nedionato(1−)]bis­[4,4,5,5-tetra­methyl­-2-(4-pyrid­yl)-imidazoline-1-oxyl 3-oxide]manganese(II)

Liu, Y.; He, Q.; Zhang, X.; Xue, Z.; Lv, C.

doi:10.1107/S1600536808038440

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1604

doi:10.1107/S1600536808038440

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: Bis[2,4-pentanedionato(1−)]bis[4,4,5,5-tetramethyl-2-(4-pyridyl)-imidazoline-1-oxyl 3-oxide]manganese(II)

Ying Liu,^a ^* Qingpeng He,^a Xianxi Zhang,^a Zechun Xue ^a and Chunyan Lv ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: yllctu@yahoo.com.cn

(Received 9 November 2008; accepted 18 November 2008; online 22 November 2008)

In the title compound, [Mn(C₅H₇O₂)₂(C₁₂H₁₆N₃O₂)], the manganese(II) cation (site symmetry $[\overline{1}]$ ) is hexacoordinated by four O and two N atoms in a distorted trans-MnN₂O₄ octahedral geometry. The four O atoms belonging to two 2,4-pentanedionate anions lie in the equatorial plane and the two N atoms occupy the axial coordination sites.

Related literature

For related structures, see: Caruso et al. (2005 ); Iskander et al. (2001 ); Rajak et al. (2000 ); Sangeetha et al. (2000 ); Sutradhar et al. (2006 ).

Experimental

Crystal data

[Mn(C₅H₇O₂)₂(C₁₂H₁₆N₃O₂)]
M_r = 721.71
Triclinic, $[P \overline 1]$
a = 7.277 (3) Å
b = 9.7167 (15) Å
c = 13.2643 (15) Å
α = 97.978 (10)°
β = 103.342 (10)°
γ = 92.869 (10)°
V = 900.4 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 (2) K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.951, T_max = 0.970
6210 measured reflections
3264 independent reflections
2511 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.00
3264 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O1	1.9964 (17)
Mn1—O3	2.0597 (17)
Mn1—N1	2.242 (2)

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 global, I. DOI: 10.1107/S1600536808038440/hb2842sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038440/hb2842Isup2.hkl

checkCIF report

Comment top

To design different kinds of metal-based coordination architectures with appropriate organic radicals and co-ligands has been an important subject during the last decade because of its potential usages for molecule-based magnetic materials and optical devices. Varying the organic units, such as tridentate nitronyl nitroxide radical, and bidentate nitroxide radical could results in a large number of building blocks with the potentional applications. In this paper, we report the structure of the title compound, (I).

As shown in Fig. 1, the manganese(II) cation is hexacoordinated with four O and two N atoms showing a slightly distorted octahedral geometry. The Mn(II) cation lies on an inversion centre. The four oxygen atoms belonging to two 2,4-pentanedionate lie in the equatorial plane and the two nitrogen atoms lie in the axial coordination sites (Table 1).

Related literature top

For related structures, see: Caruso et al. (2005); Iskander et al. (2001); Rajak et al. (2000); Sangeetha et al. (2000); Sutradhar et al. (2006).

Experimental top

A mixture of manganese(II) acetylacetonate (1 mmol) and 2-(4-pyridyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (1 mmol) in 20 ml methanol was refluxed for several hours. The above cooled solution was filtered and the filtrate was kept in an ice box. One week later, brown blocks of (I) were obtained with a yield of ca 3%. Anal. Calc. for C₃₄H₄₆N₆MnO₈: C 56.48, H 6.31, N 11.55%; Found: C 56.53, H 6.37, N 11.64%.

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) around Mn(II), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms. The unlabelled atoms are generated by the symmetry operation (-x, -y, -z).

Bis[2,4-pentanedionato(1-)]bis[4,4,5,5-tetramethyl-2-(4-pyridyl)imidazoline-1- oxyl 3-oxide]manganese(II) top

Crystal data top

[Mn(C₅H₇O₂)₂(C₁₂H₁₆N₃O₂)]	Z = 1
M_r = 721.71	F(000) = 381
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.277 (3) Å	Cell parameters from 3264 reflections
b = 9.7167 (15) Å	θ = 2.9–25.5°
c = 13.2643 (15) Å	µ = 0.42 mm⁻¹
α = 97.978 (10)°	T = 293 K
β = 103.342 (10)°	Block, brown
γ = 92.869 (10)°	0.12 × 0.10 × 0.08 mm
V = 900.4 (4) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3264 independent reflections
Radiation source: fine-focus sealed tube	2511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→8
T_min = 0.951, T_max = 0.970	k = −11→11
6210 measured reflections	l = −11→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.07P)²] where P = (F_o² + 2F_c²)/3
3264 reflections	(Δ/σ)_max = 0.007
229 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Mn(C₅H₇O₂)₂(C₁₂H₁₆N₃O₂)]	γ = 92.869 (10)°
M_r = 721.71	V = 900.4 (4) Å³
Triclinic, P1	Z = 1
a = 7.277 (3) Å	Mo Kα radiation
b = 9.7167 (15) Å	µ = 0.42 mm⁻¹
c = 13.2643 (15) Å	T = 293 K
α = 97.978 (10)°	0.12 × 0.10 × 0.08 mm
β = 103.342 (10)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3264 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2511 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.970	R_int = 0.033
6210 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.00	Δρ_max = 0.58 e Å⁻³
3264 reflections	Δρ_min = −0.51 e Å⁻³
229 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
Mn1	0.0000	0.0000	0.0000	0.0236 (6)
C1	−0.0486 (4)	0.2828 (3)	0.0582 (2)	0.0237 (6)
C2	0.2048 (4)	0.2371 (3)	−0.0432 (2)	0.0249 (6)
C3	0.3726 (4)	0.2936 (3)	−0.0812 (2)	0.0343 (7)
H3A	0.4838	0.2496	−0.0522	0.052*
H3B	0.3946	0.3926	−0.0589	0.052*
H3C	0.3449	0.2741	−0.1564	0.052*
C4	0.1139 (4)	0.3210 (3)	0.0232 (2)	0.0264 (6)
H4	0.1672	0.4122	0.0467	0.032*
C5	−0.1320 (4)	0.3856 (3)	0.1294 (2)	0.0319 (7)
H5A	−0.2665	0.3830	0.1019	0.048*
H5B	−0.0754	0.4781	0.1327	0.048*
H5C	−0.1066	0.3607	0.1985	0.048*
C6	0.1703 (4)	0.1166 (3)	0.2387 (2)	0.0220 (6)
H6	0.0417	0.1238	0.2338	0.026*
C7	0.4138 (4)	0.0539 (3)	0.1578 (2)	0.0232 (6)
H7	0.4539	0.0187	0.0984	0.028*
C8	0.5526 (4)	0.0956 (3)	0.2535 (2)	0.0246 (6)
H8	0.6802	0.0871	0.2560	0.030*
C9	0.2971 (4)	0.1612 (3)	0.3371 (2)	0.0222 (6)
H9	0.2526	0.1967	0.3950	0.027*
C10	0.4944 (4)	0.1510 (3)	0.3461 (2)	0.0222 (6)
C11	0.6315 (4)	0.1986 (3)	0.4507 (2)	0.0222 (6)
C12	0.9181 (3)	0.2690 (3)	0.58642 (19)	0.0210 (6)
C13	0.7430 (4)	0.2984 (3)	0.6343 (2)	0.0232 (6)
C14	0.7504 (4)	0.2549 (3)	0.7443 (2)	0.0307 (7)
H14A	0.6361	0.2770	0.7652	0.046*
H14B	0.8576	0.3046	0.7948	0.046*
H14C	0.7620	0.1564	0.7404	0.046*
C15	0.6888 (4)	0.4434 (3)	0.6352 (2)	0.0328 (7)
H15A	0.6878	0.4715	0.5685	0.049*
H15B	0.7786	0.5045	0.6894	0.049*
H15C	0.5648	0.4483	0.6483	0.049*
C16	1.0020 (4)	0.1369 (3)	0.6128 (2)	0.0254 (6)
H16A	0.9033	0.0623	0.5969	0.038*
H16B	1.0634	0.1492	0.6861	0.038*
H16C	1.0930	0.1147	0.5722	0.038*
C17	1.0770 (4)	0.3830 (3)	0.6102 (2)	0.0260 (6)
H17A	1.1689	0.3565	0.5711	0.039*
H17B	1.1363	0.3975	0.6838	0.039*
H17C	1.0271	0.4677	0.5908	0.039*
N1	0.2243 (3)	0.0629 (2)	0.14911 (16)	0.0214 (5)
N2	0.5856 (3)	0.2134 (2)	0.54863 (17)	0.0250 (5)
N3	0.8188 (3)	0.2417 (2)	0.46660 (17)	0.0221 (5)
O1	−0.1368 (2)	0.16513 (17)	0.03794 (14)	0.0254 (4)
O2	0.9120 (3)	0.25072 (19)	0.39302 (14)	0.0277 (4)
O3	0.1567 (2)	0.11183 (18)	−0.07693 (14)	0.0259 (4)
O4	0.4265 (3)	0.1723 (2)	0.56899 (15)	0.0351 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0270 (15)	0.0192 (14)	0.0214 (15)	0.0067 (11)	0.0002 (11)	0.0001 (11)
C1	0.0267 (14)	0.0198 (13)	0.0197 (14)	0.0041 (10)	−0.0057 (11)	0.0045 (10)
C2	0.0244 (14)	0.0214 (13)	0.0246 (15)	0.0003 (10)	−0.0055 (11)	0.0087 (11)
C3	0.0301 (16)	0.0276 (15)	0.0445 (19)	−0.0007 (12)	0.0041 (14)	0.0122 (13)
C4	0.0316 (15)	0.0180 (13)	0.0256 (15)	0.0005 (11)	−0.0013 (12)	0.0040 (11)
C5	0.0373 (17)	0.0220 (14)	0.0327 (17)	0.0074 (12)	0.0012 (13)	0.0017 (12)
C6	0.0193 (13)	0.0234 (13)	0.0245 (15)	0.0035 (10)	0.0056 (11)	0.0061 (11)
C7	0.0246 (14)	0.0242 (13)	0.0212 (15)	0.0045 (10)	0.0052 (11)	0.0045 (11)
C8	0.0208 (14)	0.0270 (14)	0.0258 (16)	0.0026 (10)	0.0051 (11)	0.0044 (11)
C9	0.0238 (14)	0.0234 (13)	0.0199 (14)	0.0033 (10)	0.0055 (11)	0.0038 (10)
C10	0.0233 (14)	0.0217 (13)	0.0209 (15)	0.0006 (10)	0.0035 (11)	0.0045 (10)
C11	0.0230 (14)	0.0260 (13)	0.0178 (14)	0.0022 (10)	0.0051 (11)	0.0030 (11)
C12	0.0201 (13)	0.0256 (14)	0.0151 (14)	0.0009 (10)	0.0007 (10)	0.0026 (10)
C13	0.0224 (14)	0.0268 (14)	0.0185 (14)	0.0038 (11)	0.0009 (11)	0.0029 (11)
C14	0.0270 (15)	0.0405 (17)	0.0236 (16)	0.0033 (12)	0.0035 (12)	0.0060 (12)
C15	0.0292 (16)	0.0346 (16)	0.0330 (18)	0.0106 (12)	0.0046 (13)	0.0017 (13)
C16	0.0225 (14)	0.0250 (14)	0.0284 (16)	0.0034 (10)	0.0040 (12)	0.0058 (11)
C17	0.0254 (14)	0.0254 (14)	0.0254 (16)	0.0013 (11)	0.0031 (12)	0.0034 (11)
N1	0.0236 (12)	0.0185 (11)	0.0221 (13)	0.0025 (8)	0.0051 (10)	0.0039 (9)
N2	0.0175 (12)	0.0340 (13)	0.0225 (13)	0.0003 (9)	0.0038 (9)	0.0040 (10)
N3	0.0192 (11)	0.0260 (11)	0.0206 (12)	0.0014 (9)	0.0038 (10)	0.0041 (9)
O1	0.0261 (10)	0.0207 (9)	0.0268 (11)	0.0038 (7)	0.0006 (8)	0.0039 (8)
O2	0.0235 (10)	0.0367 (11)	0.0239 (11)	0.0013 (8)	0.0087 (8)	0.0033 (8)
O3	0.0280 (10)	0.0210 (9)	0.0258 (11)	−0.0002 (7)	0.0011 (8)	0.0031 (8)
O4	0.0205 (10)	0.0555 (14)	0.0309 (12)	−0.0011 (9)	0.0076 (9)	0.0113 (10)

Geometric parameters (Å, º) top

Mn1—O1ⁱ	1.9964 (17)	C9—C10	1.422 (4)
Mn1—O1	1.9964 (17)	C9—H9	0.9300
Mn1—O3	2.0597 (17)	C10—C11	1.508 (4)
Mn1—O3ⁱ	2.0597 (17)	C11—N3	1.365 (3)
Mn1—N1	2.242 (2)	C11—N2	1.405 (3)
Mn1—N1ⁱ	2.242 (2)	C12—C16	1.498 (3)
C1—O1	1.246 (3)	C12—C17	1.507 (3)
C1—C4	1.417 (4)	C12—N3	1.566 (3)
C1—C5	1.524 (4)	C12—C13	1.571 (4)
C2—O3	1.241 (3)	C13—C15	1.482 (4)
C2—C4	1.415 (4)	C13—N2	1.527 (3)
C2—C3	1.530 (4)	C13—C14	1.564 (4)
C3—H3A	0.9600	C14—H14A	0.9600
C3—H3B	0.9600	C14—H14B	0.9600
C3—H3C	0.9600	C14—H14C	0.9600
C4—H4	0.9300	C15—H15A	0.9600
C5—H5A	0.9600	C15—H15B	0.9600
C5—H5B	0.9600	C15—H15C	0.9600
C5—H5C	0.9600	C16—H16A	0.9600
C6—N1	1.379 (3)	C16—H16B	0.9600
C6—C9	1.412 (4)	C16—H16C	0.9600
C6—H6	0.9300	C17—H17A	0.9600
C7—N1	1.364 (3)	C17—H17B	0.9600
C7—C8	1.421 (4)	C17—H17C	0.9600
C7—H7	0.9300	N2—O4	1.304 (3)
C8—C10	1.434 (4)	N3—O2	1.320 (3)
C8—H8	0.9300

O1ⁱ—Mn1—O1	180.0	N3—C11—N2	108.1 (2)
O1ⁱ—Mn1—O3	87.80 (7)	N3—C11—C10	126.2 (2)
O1—Mn1—O3	92.20 (7)	N2—C11—C10	125.6 (2)
O1ⁱ—Mn1—O3ⁱ	92.20 (7)	C16—C12—C17	108.1 (2)
O1—Mn1—O3ⁱ	87.80 (7)	C16—C12—N3	106.9 (2)
O3—Mn1—O3ⁱ	180.0	C17—C12—N3	110.9 (2)
O1ⁱ—Mn1—N1	90.40 (7)	C16—C12—C13	112.5 (2)
O1—Mn1—N1	89.60 (7)	C17—C12—C13	117.4 (2)
O3—Mn1—N1	89.56 (7)	N3—C12—C13	100.45 (18)
O3ⁱ—Mn1—N1	90.44 (7)	C15—C13—N2	103.7 (2)
O1ⁱ—Mn1—N1ⁱ	89.60 (7)	C15—C13—C14	109.2 (2)
O1—Mn1—N1ⁱ	90.40 (7)	N2—C13—C14	112.0 (2)
O3—Mn1—N1ⁱ	90.44 (7)	C15—C13—C12	114.0 (2)
O3ⁱ—Mn1—N1ⁱ	89.56 (7)	N2—C13—C12	100.01 (19)
N1—Mn1—N1ⁱ	180.0	C14—C13—C12	116.9 (2)
O1—C1—C4	125.9 (2)	C13—C14—H14A	109.5
O1—C1—C5	112.3 (2)	C13—C14—H14B	109.5
C4—C1—C5	121.8 (2)	H14A—C14—H14B	109.5
O3—C2—C4	123.9 (2)	C13—C14—H14C	109.5
O3—C2—C3	113.3 (2)	H14A—C14—H14C	109.5
C4—C2—C3	122.8 (2)	H14B—C14—H14C	109.5
C2—C3—H3A	109.5	C13—C15—H15A	109.5
C2—C3—H3B	109.5	C13—C15—H15B	109.5
H3A—C3—H3B	109.5	H15A—C15—H15B	109.5
C2—C3—H3C	109.5	C13—C15—H15C	109.5
H3A—C3—H3C	109.5	H15A—C15—H15C	109.5
H3B—C3—H3C	109.5	H15B—C15—H15C	109.5
C2—C4—C1	127.8 (2)	C12—C16—H16A	109.5
C2—C4—H4	116.1	C12—C16—H16B	109.5
C1—C4—H4	116.1	H16A—C16—H16B	109.5
C1—C5—H5A	109.5	C12—C16—H16C	109.5
C1—C5—H5B	109.5	H16A—C16—H16C	109.5
H5A—C5—H5B	109.5	H16B—C16—H16C	109.5
C1—C5—H5C	109.5	C12—C17—H17A	109.5
H5A—C5—H5C	109.5	C12—C17—H17B	109.5
H5B—C5—H5C	109.5	H17A—C17—H17B	109.5
N1—C6—C9	124.4 (2)	C12—C17—H17C	109.5
N1—C6—H6	117.8	H17A—C17—H17C	109.5
C9—C6—H6	117.8	H17B—C17—H17C	109.5
N1—C7—C8	123.1 (2)	C7—N1—C6	116.8 (2)
N1—C7—H7	118.5	C7—N1—Mn1	124.50 (17)
C8—C7—H7	118.5	C6—N1—Mn1	118.67 (16)
C7—C8—C10	119.5 (2)	O4—N2—C11	127.6 (2)
C7—C8—H8	120.2	O4—N2—C13	120.6 (2)
C10—C8—H8	120.2	C11—N2—C13	111.6 (2)
C6—C9—C10	118.6 (2)	O2—N3—C11	126.1 (2)
C6—C9—H9	120.7	O2—N3—C12	122.78 (18)
C10—C9—H9	120.7	C11—N3—C12	110.91 (19)
C9—C10—C8	117.6 (2)	C1—O1—Mn1	118.40 (17)
C9—C10—C11	119.2 (2)	C2—O3—Mn1	119.22 (17)
C8—C10—C11	123.2 (2)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Mn(C₅H₇O₂)₂(C₁₂H₁₆N₃O₂)]
M_r	721.71
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.277 (3), 9.7167 (15), 13.2643 (15)
α, β, γ (°)	97.978 (10), 103.342 (10), 92.869 (10)
V (Å³)	900.4 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.951, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	6210, 3264, 2511
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.00
No. of reflections	3264
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.51

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

Selected bond lengths (Å) top

Mn1—O1	1.9964 (17)	Mn1—N1	2.242 (2)
Mn1—O3	2.0597 (17)

Acknowledgements

The authors thank the National Ministry of Science and Technology of China (grant No. 2001CB6105-07).

References

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