supplementary materials


Acta Cryst. (2009). E65, m1441    [ doi:10.1107/S1600536809043591 ]

[2-Oxido-1-naphthaldehyde (2-hydroxybenzoyl)hydrazonato]diphenyltin(IV)

J. Li, H. Yin, L. Wen and J. Cui

Abstract top

In the title compound, [Sn(C6H5)2(C18H12N2O3)], the SnIV atom has a distorted trigonal-bipyramidal geometry. The Schiff base molecule is coordinated to the SnIV atom in a tridentate fashion via the azomethine N atom, the hydroxy O atom and the carbonyl O atom. The complex involves an intramolecular O-H...N hydrogen bond.

Comment top

The molecular structure of the title compound is shown in Fig. 1. The SnIV atom is five-coordinated by two O atoms, two C atoms and one N atom. The distortion around the SnIV atom is a result of the constraints imposed by the Sn1–N2–N1–C1–O1 and Sn1–N2–C8–C9–C10–O3 rings. The dihedral angles between the two benzene rings (C19 to C24 and C25 to C30) and the O3–Sn1–N2 plane are 61.5 (1) and 67.2 (1)°, respectively. The Sn1—N2 distance is 2.154 (3) Å, close to the sum of the covalent radii (2.15 Å; Sanderson, 1967), indicating a strong Sn—N interaction. The O atoms coordinate to the Sn atom with one shorter and one longer Sn—O bond. Very similar structural parameters were observed in the compound studied by Yearwood et al. (2002). The angles at Sn1 confirm that the complex has a distorted trigonal-bipyramidal geometry.

Related literature top

For related structures, see: Chen et al. (2006); Yearwood et al. (2002). For atomic covalent radii, see: Sanderson (1967).

Experimental top

2-Hydroxybenzhydrazide (5 mol) was added to 30 ml ethanol. The mixture was stirred for 0.5 h and then 2-hyroxy-1-naphthyldehyde (5 mol) was added, generating a yellow sediment immediately. The product was recrystallized from ethanol and DMF mixed solvent to get yellow crystals of 2-hydroxy-1-naphthaldehyde 2-benzoylhydrazone (L). The preparation of the title compound was carried out under nitrogen atmosphere. L (4 mmol) was added to a mixture of ethanol and benzene (v/v 1:3, 30 ml) with sodium ethoxide (4 mmol). The mixture was stirred for 0.5 h and then dichlorodiphenyltin (4 mmol) was added. The mixture was stirred for 12 h under reflux. After cooling to room temperature, the mixture was filtered and evaporated to dryness. The resulting solid was then recrystallized from dichloromethane-hexane (v/v 1:1). Analysis, calculated for C30H22N2O3Sn: C 62.42, H 3.84, N 4.85, O 8.32%; found: C 62.30, H 3.75, N 4.92, O 8.28%.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and O—H = 0.82 Å and with Uiso(H) = 1.2(1.5 for hydroxyl)Ueq(C, O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the title compound.
[2-Oxido-1-naphthaldehyde (2-hydroxybenzoyl)hydrazonato]diphenyltin(IV) top
Crystal data top
[Sn(C6H5)2(C18H12N2O3)]F(000) = 1160
Mr = 577.19Dx = 1.518 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4435 reflections
a = 9.418 (1) Åθ = 2.5–24.5°
b = 11.0861 (12) ŵ = 1.05 mm1
c = 25.668 (2) ÅT = 293 K
β = 109.547 (2)°Block, colorless
V = 2525.5 (4) Å30.43 × 0.29 × 0.20 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD
diffractometer
4435 independent reflections
Radiation source: fine-focus sealed tube3263 reflections with I > 2σ(I)
graphiteRint = 0.031
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.662, Tmax = 0.818k = 1113
12414 measured reflectionsl = 3030
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0238P)2 + 1.7663P]
where P = (Fo2 + 2Fc2)/3
4435 reflections(Δ/σ)max = 0.003
325 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
[Sn(C6H5)2(C18H12N2O3)]V = 2525.5 (4) Å3
Mr = 577.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.418 (1) ŵ = 1.05 mm1
b = 11.0861 (12) ÅT = 293 K
c = 25.668 (2) Å0.43 × 0.29 × 0.20 mm
β = 109.547 (2)°
Data collection top
Siemens SMART 1000 CCD
diffractometer
4435 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3263 reflections with I > 2σ(I)
Tmin = 0.662, Tmax = 0.818Rint = 0.031
12414 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.073Δρmax = 0.43 e Å3
S = 1.03Δρmin = 0.33 e Å3
4435 reflectionsAbsolute structure: ?
325 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.89811 (3)0.74107 (2)0.920886 (10)0.04851 (10)
N10.8396 (4)0.4718 (2)0.91811 (11)0.0465 (8)
N20.8343 (3)0.5736 (2)0.94938 (11)0.0434 (7)
O10.9135 (3)0.6067 (2)0.86422 (10)0.0647 (8)
O20.7809 (4)0.2520 (2)0.88057 (12)0.0834 (10)
H20.78480.30890.90150.125*
O30.8815 (3)0.8048 (2)0.99407 (10)0.0589 (7)
C10.8817 (4)0.4984 (3)0.87560 (14)0.0459 (9)
C20.8935 (4)0.4009 (3)0.83892 (14)0.0493 (9)
C30.8422 (5)0.2849 (3)0.84222 (15)0.0576 (11)
C40.8529 (6)0.1978 (4)0.80504 (18)0.0794 (14)
H40.81930.11980.80750.095*
C50.9126 (7)0.2261 (5)0.7647 (2)0.0918 (17)
H50.91660.16760.73920.110*
C60.9665 (7)0.3391 (5)0.7614 (2)0.1001 (19)
H61.01000.35730.73470.120*
C70.9554 (6)0.4251 (4)0.79798 (17)0.0753 (14)
H70.99050.50250.79540.090*
C80.7840 (4)0.5562 (3)0.99031 (14)0.0449 (9)
H80.75500.47790.99500.054*
C90.7683 (4)0.6439 (3)1.02883 (13)0.0428 (9)
C100.8202 (4)0.7625 (3)1.02946 (14)0.0482 (9)
C110.8110 (5)0.8440 (3)1.07056 (15)0.0557 (10)
H110.84600.92251.07080.067*
C120.7523 (5)0.8097 (4)1.10938 (16)0.0609 (11)
H120.74960.86481.13640.073*
C130.6946 (5)0.6924 (4)1.11023 (16)0.0561 (11)
C140.7010 (4)0.6071 (3)1.07003 (15)0.0507 (10)
C150.6398 (5)0.4933 (4)1.07211 (17)0.0640 (12)
H150.64010.43631.04550.077*
C160.5797 (6)0.4627 (4)1.1119 (2)0.0826 (15)
H160.54100.38561.11220.099*
C170.5756 (6)0.5453 (5)1.1519 (2)0.0878 (16)
H170.53460.52421.17900.105*
C180.6327 (6)0.6582 (4)1.15106 (18)0.0751 (14)
H180.63080.71371.17800.090*
C191.1244 (4)0.7942 (3)0.93967 (14)0.0444 (9)
C201.2167 (5)0.8207 (3)0.99286 (15)0.0572 (11)
H201.17790.81791.02170.069*
C211.3657 (5)0.8514 (4)1.0035 (2)0.0748 (13)
H211.42750.86611.03960.090*
C221.4234 (6)0.8602 (4)0.9612 (2)0.0763 (13)
H221.52360.88210.96860.092*
C231.3339 (6)0.8371 (4)0.9084 (2)0.0707 (13)
H231.37230.84450.87960.085*
C241.1862 (5)0.8026 (3)0.89768 (16)0.0585 (11)
H241.12680.78460.86160.070*
C250.7141 (4)0.8331 (3)0.86445 (15)0.0508 (10)
C260.6817 (5)0.9491 (4)0.87485 (19)0.0700 (12)
H260.74120.98680.90710.084*
C270.5624 (6)1.0113 (5)0.8384 (2)0.0913 (16)
H270.54361.09070.84590.110*
C280.4723 (6)0.9565 (7)0.7916 (2)0.0969 (19)
H280.39110.99800.76740.116*
C290.5006 (6)0.8424 (7)0.7803 (2)0.0976 (18)
H290.43860.80500.74840.117*
C300.6228 (5)0.7797 (4)0.81640 (18)0.0751 (13)
H300.64270.70130.80790.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.05637 (18)0.04439 (15)0.04495 (15)0.01070 (14)0.01717 (12)0.00358 (12)
N10.058 (2)0.0411 (16)0.0412 (17)0.0028 (14)0.0175 (16)0.0055 (13)
N20.048 (2)0.0421 (16)0.0400 (17)0.0043 (14)0.0142 (15)0.0034 (13)
O10.094 (2)0.0545 (16)0.0572 (17)0.0219 (15)0.0407 (17)0.0132 (13)
O20.138 (3)0.0483 (16)0.079 (2)0.0149 (18)0.057 (2)0.0112 (15)
O30.080 (2)0.0532 (15)0.0504 (16)0.0166 (14)0.0309 (15)0.0128 (12)
C10.048 (3)0.046 (2)0.039 (2)0.0072 (18)0.0094 (18)0.0046 (16)
C20.054 (3)0.054 (2)0.036 (2)0.0022 (19)0.0113 (19)0.0059 (17)
C30.071 (3)0.053 (2)0.045 (2)0.008 (2)0.014 (2)0.0043 (18)
C40.114 (4)0.057 (3)0.067 (3)0.009 (3)0.029 (3)0.016 (2)
C50.120 (5)0.091 (4)0.065 (3)0.017 (3)0.032 (3)0.029 (3)
C60.142 (6)0.111 (4)0.064 (3)0.014 (4)0.056 (4)0.025 (3)
C70.097 (4)0.079 (3)0.057 (3)0.018 (3)0.037 (3)0.015 (2)
C80.051 (3)0.041 (2)0.044 (2)0.0003 (17)0.0162 (19)0.0026 (16)
C90.043 (2)0.045 (2)0.037 (2)0.0062 (17)0.0096 (17)0.0028 (15)
C100.047 (2)0.050 (2)0.044 (2)0.0035 (19)0.0112 (17)0.0021 (18)
C110.062 (3)0.050 (2)0.052 (2)0.002 (2)0.016 (2)0.0086 (18)
C120.068 (3)0.063 (3)0.053 (3)0.011 (2)0.021 (2)0.010 (2)
C130.060 (3)0.059 (2)0.052 (2)0.013 (2)0.023 (2)0.0021 (19)
C140.051 (3)0.052 (2)0.050 (2)0.0134 (19)0.018 (2)0.0057 (18)
C150.082 (4)0.058 (3)0.066 (3)0.005 (2)0.044 (3)0.003 (2)
C160.112 (5)0.071 (3)0.091 (4)0.001 (3)0.069 (3)0.007 (3)
C170.118 (5)0.089 (4)0.084 (4)0.014 (3)0.071 (4)0.014 (3)
C180.097 (4)0.077 (3)0.068 (3)0.016 (3)0.050 (3)0.003 (2)
C190.052 (2)0.0325 (18)0.047 (2)0.0046 (16)0.0141 (19)0.0030 (15)
C200.063 (3)0.062 (3)0.044 (2)0.007 (2)0.014 (2)0.0018 (18)
C210.059 (3)0.078 (3)0.068 (3)0.011 (3)0.004 (3)0.002 (2)
C220.055 (3)0.067 (3)0.106 (4)0.008 (2)0.027 (3)0.003 (3)
C230.076 (4)0.063 (3)0.089 (4)0.010 (2)0.048 (3)0.002 (2)
C240.067 (3)0.063 (2)0.047 (2)0.010 (2)0.022 (2)0.0004 (19)
C250.050 (3)0.056 (2)0.045 (2)0.0142 (19)0.0134 (19)0.0039 (17)
C260.059 (3)0.066 (3)0.077 (3)0.002 (2)0.012 (3)0.005 (2)
C270.080 (4)0.081 (4)0.106 (5)0.008 (3)0.021 (4)0.023 (3)
C280.058 (4)0.141 (6)0.088 (4)0.008 (4)0.019 (3)0.052 (4)
C290.070 (4)0.153 (6)0.055 (3)0.024 (4)0.001 (3)0.007 (4)
C300.076 (3)0.087 (3)0.054 (3)0.019 (3)0.011 (2)0.006 (2)
Geometric parameters (Å, °) top
Sn1—O12.121 (2)C13—C181.411 (5)
Sn1—O32.061 (2)C13—C141.415 (5)
Sn1—N22.154 (3)C14—C151.396 (5)
Sn1—C192.106 (4)C15—C161.366 (5)
Sn1—C252.113 (4)C15—H150.9300
N1—C11.313 (4)C16—C171.387 (6)
N1—N21.395 (4)C16—H160.9300
N2—C81.303 (4)C17—C181.365 (6)
O1—C11.294 (4)C17—H170.9300
O2—C31.348 (5)C18—H180.9300
O2—H20.8200C19—C201.383 (5)
O3—C101.315 (4)C19—C241.389 (5)
C1—C21.462 (5)C20—C211.380 (6)
C2—C31.386 (5)C20—H200.9300
C2—C71.388 (5)C21—C221.370 (6)
C3—C41.384 (5)C21—H210.9300
C4—C51.371 (6)C22—C231.359 (6)
C4—H40.9300C22—H220.9300
C5—C61.364 (7)C23—C241.378 (6)
C5—H50.9300C23—H230.9300
C6—C71.366 (6)C24—H240.9300
C6—H60.9300C25—C261.368 (5)
C7—H70.9300C25—C301.379 (5)
C8—C91.429 (5)C26—C271.382 (6)
C8—H80.9300C26—H260.9300
C9—C101.401 (5)C27—C281.360 (7)
C9—C141.461 (5)C27—H270.9300
C10—C111.414 (5)C28—C291.344 (8)
C11—C121.346 (5)C28—H280.9300
C11—H110.9300C29—C301.397 (7)
C12—C131.413 (6)C29—H290.9300
C12—H120.9300C30—H300.9300
O3—Sn1—C1994.31 (12)C18—C13—C14119.4 (4)
O3—Sn1—C2599.45 (13)C12—C13—C14119.6 (3)
C19—Sn1—C25123.88 (13)C15—C14—C13117.2 (3)
O3—Sn1—O1155.42 (10)C15—C14—C9124.3 (3)
C19—Sn1—O193.27 (12)C13—C14—C9118.4 (3)
C25—Sn1—O195.61 (13)C16—C15—C14122.2 (4)
O3—Sn1—N282.61 (10)C16—C15—H15118.9
C19—Sn1—N2122.65 (12)C14—C15—H15118.9
C25—Sn1—N2113.00 (13)C15—C16—C17120.7 (4)
O1—Sn1—N273.63 (10)C15—C16—H16119.6
C1—N1—N2112.1 (3)C17—C16—H16119.6
C8—N2—N1115.9 (3)C18—C17—C16119.0 (4)
C8—N2—Sn1128.2 (2)C18—C17—H17120.5
N1—N2—Sn1115.7 (2)C16—C17—H17120.5
C1—O1—Sn1115.0 (2)C17—C18—C13121.4 (4)
C3—O2—H2109.5C17—C18—H18119.3
C10—O3—Sn1133.8 (2)C13—C18—H18119.3
O1—C1—N1123.6 (3)C20—C19—C24117.7 (4)
O1—C1—C2117.9 (3)C20—C19—Sn1122.6 (3)
N1—C1—C2118.6 (3)C24—C19—Sn1119.7 (3)
C3—C2—C7118.0 (3)C21—C20—C19120.6 (4)
C3—C2—C1122.9 (3)C21—C20—H20119.7
C7—C2—C1119.1 (4)C19—C20—H20119.7
O2—C3—C4117.6 (4)C22—C21—C20120.5 (4)
O2—C3—C2122.6 (3)C22—C21—H21119.8
C4—C3—C2119.9 (4)C20—C21—H21119.8
C5—C4—C3120.2 (5)C23—C22—C21119.9 (5)
C5—C4—H4119.9C23—C22—H22120.1
C3—C4—H4119.9C21—C22—H22120.1
C6—C5—C4120.8 (4)C22—C23—C24120.0 (4)
C6—C5—H5119.6C22—C23—H23120.0
C4—C5—H5119.6C24—C23—H23120.0
C5—C6—C7118.9 (5)C23—C24—C19121.3 (4)
C5—C6—H6120.5C23—C24—H24119.3
C7—C6—H6120.5C19—C24—H24119.3
C6—C7—C2122.2 (5)C26—C25—C30117.7 (4)
C6—C7—H7118.9C26—C25—Sn1120.3 (3)
C2—C7—H7118.9C30—C25—Sn1121.9 (3)
N2—C8—C9127.4 (3)C25—C26—C27121.4 (5)
N2—C8—H8116.3C25—C26—H26119.3
C9—C8—H8116.3C27—C26—H26119.3
C10—C9—C8122.0 (3)C28—C27—C26120.0 (5)
C10—C9—C14119.2 (3)C28—C27—H27120.0
C8—C9—C14118.8 (3)C26—C27—H27120.0
O3—C10—C9124.0 (3)C29—C28—C27120.1 (5)
O3—C10—C11115.9 (3)C29—C28—H28120.0
C9—C10—C11120.0 (3)C27—C28—H28120.0
C12—C11—C10121.0 (4)C28—C29—C30120.3 (5)
C12—C11—H11119.5C28—C29—H29119.9
C10—C11—H11119.5C30—C29—H29119.9
C11—C12—C13121.8 (4)C25—C30—C29120.5 (5)
C11—C12—H12119.1C25—C30—H30119.7
C13—C12—H12119.1C29—C30—H30119.7
C18—C13—C12121.0 (4)
C1—N1—N2—C8175.7 (3)C11—C12—C13—C18179.6 (4)
C1—N1—N2—Sn10.9 (4)C11—C12—C13—C141.3 (6)
O3—Sn1—N2—C811.5 (3)C18—C13—C14—C152.1 (6)
C19—Sn1—N2—C8101.9 (3)C12—C13—C14—C15178.8 (4)
C25—Sn1—N2—C885.7 (3)C18—C13—C14—C9178.8 (4)
O1—Sn1—N2—C8174.9 (3)C12—C13—C14—C90.3 (6)
O3—Sn1—N2—N1172.4 (2)C10—C9—C14—C15177.3 (4)
C19—Sn1—N2—N182.1 (3)C8—C9—C14—C154.9 (6)
C25—Sn1—N2—N190.4 (3)C10—C9—C14—C131.8 (5)
O1—Sn1—N2—N11.2 (2)C8—C9—C14—C13176.0 (3)
O3—Sn1—O1—C114.0 (5)C13—C14—C15—C161.8 (7)
C19—Sn1—O1—C1121.8 (3)C9—C14—C15—C16179.2 (4)
C25—Sn1—O1—C1113.7 (3)C14—C15—C16—C170.7 (8)
N2—Sn1—O1—C11.3 (3)C15—C16—C17—C180.0 (8)
C19—Sn1—O3—C10137.9 (3)C16—C17—C18—C130.4 (8)
C25—Sn1—O3—C1096.7 (3)C12—C13—C18—C17179.4 (5)
O1—Sn1—O3—C1030.3 (5)C14—C13—C18—C171.5 (7)
N2—Sn1—O3—C1015.5 (3)O3—Sn1—C19—C2017.9 (3)
Sn1—O1—C1—N11.4 (5)C25—Sn1—C19—C20122.4 (3)
Sn1—O1—C1—C2178.6 (3)O1—Sn1—C19—C20138.7 (3)
N2—N1—C1—O10.3 (5)N2—Sn1—C19—C2066.0 (3)
N2—N1—C1—C2179.7 (3)O3—Sn1—C19—C24162.6 (3)
O1—C1—C2—C3170.6 (4)C25—Sn1—C19—C2458.2 (3)
N1—C1—C2—C39.4 (6)O1—Sn1—C19—C2440.8 (3)
O1—C1—C2—C77.9 (6)N2—Sn1—C19—C24113.5 (3)
N1—C1—C2—C7172.1 (4)C24—C19—C20—C211.6 (6)
C7—C2—C3—O2179.7 (4)Sn1—C19—C20—C21177.9 (3)
C1—C2—C3—O21.8 (6)C19—C20—C21—C222.3 (7)
C7—C2—C3—C40.5 (6)C20—C21—C22—C230.9 (7)
C1—C2—C3—C4178.0 (4)C21—C22—C23—C241.2 (7)
O2—C3—C4—C5179.3 (5)C22—C23—C24—C191.9 (7)
C2—C3—C4—C50.6 (7)C20—C19—C24—C230.5 (6)
C3—C4—C5—C61.9 (8)Sn1—C19—C24—C23180.0 (3)
C4—C5—C6—C72.1 (9)O3—Sn1—C25—C2637.8 (3)
C5—C6—C7—C21.1 (9)C19—Sn1—C25—C2664.0 (4)
C3—C2—C7—C60.2 (7)O1—Sn1—C25—C26161.7 (3)
C1—C2—C7—C6178.4 (5)N2—Sn1—C25—C26123.7 (3)
N1—N2—C8—C9179.4 (3)O3—Sn1—C25—C30142.1 (3)
Sn1—N2—C8—C94.6 (6)C19—Sn1—C25—C30116.1 (3)
N2—C8—C9—C105.8 (6)O1—Sn1—C25—C3018.4 (3)
N2—C8—C9—C14176.5 (4)N2—Sn1—C25—C3056.2 (4)
Sn1—O3—C10—C911.6 (6)C30—C25—C26—C270.4 (7)
Sn1—O3—C10—C11169.6 (3)Sn1—C25—C26—C27179.7 (4)
C8—C9—C10—O32.8 (6)C25—C26—C27—C281.4 (8)
C14—C9—C10—O3179.5 (3)C26—C27—C28—C291.0 (8)
C8—C9—C10—C11176.0 (3)C27—C28—C29—C300.3 (8)
C14—C9—C10—C111.7 (5)C26—C25—C30—C290.9 (7)
O3—C10—C11—C12179.0 (4)Sn1—C25—C30—C29179.0 (4)
C9—C10—C11—C120.2 (6)C28—C29—C30—C251.2 (8)
C10—C11—C12—C131.4 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.892.611 (5)146
Table 1
Selected geometric parameters (Å)
top
Sn1—O12.121 (2)Sn1—C192.106 (4)
Sn1—O32.061 (2)Sn1—C252.113 (4)
Sn1—N22.154 (3)
Table 2
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.892.611 (5)146
Acknowledgements top

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

references
References top

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