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Acta Cryst. (2008). E64, o2249    [ doi:10.1107/S1600536808034892 ]

Benzyl N'-(2-chlorobenzylidene)hydrazinecarbodithioate

Z.-Q. Shi, N.-N. Ji and Q.-Q. Ji

Abstract top

The asymmetric unit of the title compound, C15H13ClN2S2, contains two independent molecules, which are linked into a pseudo-centrosymmetric dimer by intermolecular N-H...S hydrogen bonds. The aromatic rings form dihedral angles of 67.06 (3) and 81.85 (2)° in the two independent molecules.

Comment top

In recent years, the intriguing coordination chemistry and increasingly important biomedical properties of ligands derived from S-benzyldithiocarbazate(SBDTC) have received much attention (Ali et al., 2001, 2002; Tarafder et al., 2001, 2008). In order to search for new ligands derived from SBDTC, the title compound, (I), was synthesized. Herewith we present its crystal structure.

In (I), all bond lengths and angles are normal (Allen et al., 1987). The C=N bond length in the independent molecules are 1.279 (3) Å(C7=N2) and 1.271 (4) Å(C22=N4), respectively, showing the double-bond character. The C=S bond lengths of 1.656 (3) Å(S2=C8) and 1.661 (3) Å(S4=C23) are intermediate between the values of 1.82Å for a C—S single bond and 1.56Å for a C=S double bond. The C=N—N angles in the independent molecule of 115.5 (2)° and 115.6 (3)° are significantly smaller than the ideal value of 120° expected for sp2-hybridized N atoms. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N bonds.

Two independent molecules are linked by N—H···S hydrogen bonds (Table 1) into pseudo-centrosymmetric dimers (Fig. 1).

Related literature top

For the biomedical properties of ligands derived from

S-benzyldithiocarbazaterelated literature, see: Ali et al. (2001, 2002); Tarafder et al. (2001, 2008). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by the reaction of hydrazinecarbodithioic acid benzyl ester(1 mmol, 198.3 mg) with 2-chloro-benzaldehyde(1 mmol, 140.6 mg) in ethanol(20 ml) under reflux conditions (343 K) for 6 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After five days yellow crystals suitable for X-ray diffraction study were obtained.

Refinement top

All H atoms were placed in idealized positions (C—H = 0.93— 0.97 Å, N—H = 0.86 Å) and refined as riding atoms. For those bound to C, Uiso(H) = 1.2 or 1.5Ueq(C). while for those bound to N, Uiso(H) = 1.2 Ueq(N).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005) and SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 (I), with displacement ellipsoids drawn at the 30% probability level. Dashed lines indicate hydrogen bonds.
Benzyl N'-(2-chlorobenzylidene)hydrazinecarbodithioate top
Crystal data top
C15H13ClN2S2Z = 4
Mr = 320.84F(000) = 664
Triclinic, P1Dx = 1.359 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.877 (2) ÅCell parameters from 1618 reflections
b = 11.906 (2) Åθ = 2.6–24.6°
c = 12.623 (3) ŵ = 0.50 mm−1
α = 68.242 (3)°T = 295 K
β = 71.116 (4)°Block, yellow
γ = 82.335 (4)°0.12 × 0.10 × 0.06 mm
V = 1568.4 (5) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5524 independent reflections
Radiation source: fine-focus sealed tube3436 reflections with I > 2σ(I)
graphiteRint = 0.026
φ and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −11→14
Tmin = 0.942, Tmax = 0.971k = −14→13
8397 measured reflectionsl = −14→14
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0533P)2 + 0.4623P]
where P = (Fo2 + 2Fc2)/3
5524 reflections(Δ/σ)max = 0.001
361 parametersΔρmax = 0.44 e Å−3
0 restraintsΔρmin = −0.46 e Å−3
Crystal data top
C15H13ClN2S2γ = 82.335 (4)°
Mr = 320.84V = 1568.4 (5) Å3
Triclinic, P1Z = 4
a = 11.877 (2) ÅMo Kα radiation
b = 11.906 (2) ŵ = 0.50 mm−1
c = 12.623 (3) ÅT = 295 K
α = 68.242 (3)°0.12 × 0.10 × 0.06 mm
β = 71.116 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5524 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		3436 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.971Rint = 0.026
8397 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.44 e Å−3
S = 0.97Δρmin = −0.46 e Å−3
5524 reflectionsAbsolute structure: ?
361 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Cl20.61916 (10)0.15814 (11)0.57081 (9)0.0994 (4)
S30.36389 (7)0.66976 (8)0.21058 (7)0.0541 (3)
S40.15028 (7)0.61729 (8)0.43141 (7)0.0566 (3)
N30.3563 (2)0.5043 (2)0.4167 (2)0.0514 (7)
H3A0.32700.46340.49140.062*
N40.4704 (2)0.4789 (2)0.3570 (2)0.0478 (7)
C160.6959 (3)0.2483 (3)0.4266 (3)0.0544 (9)
C170.6419 (3)0.3506 (3)0.3648 (3)0.0455 (8)
C180.7096 (3)0.4188 (3)0.2498 (3)0.0554 (9)
H180.67700.48880.20560.066*
C190.8242 (3)0.3835 (3)0.2014 (3)0.0606 (10)
H190.86780.42900.12440.073*
C200.8742 (3)0.2812 (4)0.2663 (3)0.0617 (10)
H200.95180.25840.23320.074*
C210.8112 (3)0.2133 (3)0.3785 (3)0.0631 (10)
H210.84520.14430.42240.076*
C220.5211 (3)0.3882 (3)0.4168 (3)0.0504 (8)
H220.48020.34490.49550.061*
C230.2902 (3)0.5914 (3)0.3608 (3)0.0441 (8)
C240.2502 (3)0.7786 (3)0.1668 (3)0.0612 (10)
H24A0.17720.73720.18610.073*
H24B0.23350.83470.20970.073*
C250.2944 (3)0.8461 (3)0.0345 (3)0.0480 (8)
C260.3717 (3)0.9404 (3)−0.0123 (3)0.0609 (10)
H260.39810.96280.03890.073*
C270.4111 (3)1.0026 (3)−0.1335 (3)0.0689 (11)
H270.46361.0661−0.16340.083*
C280.3730 (3)0.9712 (4)−0.2098 (3)0.0684 (11)
H280.39941.0132−0.29160.082*
C290.2967 (3)0.8785 (4)−0.1655 (3)0.0716 (11)
H290.27020.8573−0.21720.086*
C300.2579 (3)0.8152 (3)−0.0442 (3)0.0623 (10)
H300.20650.7509−0.01510.075*
Cl1−0.22425 (9)0.74778 (9)0.55632 (8)0.0702 (3)
S10.06032 (8)0.28590 (8)0.93397 (7)0.0589 (3)
S20.25595 (8)0.30266 (9)0.70505 (7)0.0619 (3)
N10.0603 (2)0.4336 (2)0.7232 (2)0.0497 (7)
H10.08570.46790.64690.060*
N2−0.0472 (2)0.4698 (2)0.7859 (2)0.0466 (7)
C1−0.2804 (3)0.6881 (3)0.7111 (3)0.0492 (8)
C2−0.2159 (3)0.6018 (3)0.7786 (3)0.0444 (8)
C3−0.2674 (3)0.5582 (3)0.9025 (3)0.0577 (9)
H3−0.22690.50020.95040.069*
C4−0.3772 (3)0.5999 (4)0.9548 (3)0.0728 (11)
H4−0.40980.57081.03750.087*
C5−0.4383 (3)0.6844 (4)0.8849 (4)0.0804 (13)
H5−0.51280.71180.92050.097*
C6−0.3909 (3)0.7286 (4)0.7634 (3)0.0669 (10)
H6−0.43290.78570.71640.080*
C7−0.1006 (3)0.5565 (3)0.7233 (3)0.0461 (8)
H7−0.06520.59100.64130.055*
C80.1257 (3)0.3461 (3)0.7791 (3)0.0446 (8)
C90.1668 (3)0.1677 (3)0.9769 (3)0.0613 (10)
H9A0.18020.11500.93080.074*
H9B0.24210.20300.96140.074*
C100.1176 (3)0.0961 (3)1.1086 (3)0.0476 (8)
C110.1692 (3)0.1043 (3)1.1888 (3)0.0572 (9)
H110.23250.15611.16200.069*
C120.1273 (3)0.0359 (3)1.3090 (3)0.0639 (10)
H120.16320.04151.36220.077*
C130.0338 (3)−0.0398 (3)1.3501 (3)0.0632 (10)
H130.0060−0.08541.43100.076*
C14−0.0190 (3)−0.0484 (3)1.2711 (3)0.0672 (11)
H14−0.0827−0.09991.29830.081*
C150.0231 (3)0.0200 (3)1.1512 (3)0.0617 (10)
H15−0.01320.01441.09820.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0801 (8)0.0990 (9)0.0654 (7)0.0195 (6)−0.0101 (6)0.0142 (6)
S30.0454 (5)0.0542 (6)0.0410 (5)0.0071 (4)−0.0009 (4)−0.0054 (4)
S40.0451 (5)0.0626 (6)0.0416 (5)0.0100 (4)−0.0017 (4)−0.0085 (4)
N30.0410 (16)0.0570 (18)0.0386 (15)0.0077 (13)−0.0044 (12)−0.0063 (13)
N40.0396 (15)0.0508 (17)0.0441 (16)0.0053 (13)−0.0071 (13)−0.0135 (13)
C160.046 (2)0.064 (2)0.0444 (19)0.0060 (17)−0.0116 (16)−0.0131 (17)
C170.0387 (18)0.050 (2)0.0456 (18)0.0053 (15)−0.0141 (15)−0.0155 (16)
C180.051 (2)0.056 (2)0.054 (2)0.0006 (17)−0.0130 (17)−0.0162 (17)
C190.056 (2)0.069 (3)0.052 (2)−0.005 (2)−0.0029 (18)−0.0267 (19)
C200.045 (2)0.077 (3)0.070 (3)0.012 (2)−0.0156 (19)−0.040 (2)
C210.057 (2)0.071 (3)0.063 (2)0.019 (2)−0.027 (2)−0.025 (2)
C220.047 (2)0.052 (2)0.0402 (18)0.0013 (17)−0.0081 (16)−0.0086 (16)
C230.0441 (18)0.0427 (19)0.0399 (17)0.0017 (15)−0.0081 (15)−0.0126 (15)
C240.049 (2)0.059 (2)0.051 (2)0.0140 (17)−0.0038 (17)−0.0065 (17)
C250.0372 (18)0.045 (2)0.0478 (19)0.0061 (15)−0.0070 (15)−0.0073 (16)
C260.064 (2)0.065 (2)0.051 (2)−0.010 (2)−0.0216 (18)−0.0108 (19)
C270.073 (3)0.062 (3)0.057 (2)−0.020 (2)−0.014 (2)−0.002 (2)
C280.064 (2)0.075 (3)0.048 (2)0.002 (2)−0.0136 (19)−0.004 (2)
C290.064 (2)0.093 (3)0.060 (2)0.000 (2)−0.026 (2)−0.024 (2)
C300.044 (2)0.060 (2)0.077 (3)−0.0071 (18)−0.0144 (19)−0.019 (2)
Cl10.0795 (7)0.0724 (7)0.0449 (5)0.0055 (5)−0.0195 (5)−0.0065 (4)
S10.0544 (5)0.0630 (6)0.0368 (5)0.0098 (4)−0.0037 (4)−0.0044 (4)
S20.0575 (6)0.0645 (6)0.0414 (5)0.0168 (5)−0.0038 (4)−0.0092 (4)
N10.0471 (16)0.0566 (18)0.0324 (14)0.0087 (14)−0.0064 (12)−0.0090 (13)
N20.0382 (15)0.0541 (17)0.0400 (15)0.0016 (13)−0.0064 (12)−0.0133 (13)
C10.050 (2)0.053 (2)0.0430 (19)0.0028 (17)−0.0150 (16)−0.0158 (16)
C20.0414 (18)0.048 (2)0.0406 (18)−0.0013 (15)−0.0083 (15)−0.0144 (15)
C30.056 (2)0.061 (2)0.045 (2)0.0045 (18)−0.0118 (17)−0.0111 (17)
C40.058 (2)0.092 (3)0.049 (2)0.005 (2)−0.0011 (19)−0.019 (2)
C50.050 (2)0.108 (4)0.075 (3)0.021 (2)−0.010 (2)−0.038 (3)
C60.057 (2)0.078 (3)0.065 (3)0.019 (2)−0.025 (2)−0.025 (2)
C70.0427 (18)0.050 (2)0.0369 (17)0.0004 (16)−0.0086 (15)−0.0086 (15)
C80.0452 (18)0.0440 (19)0.0380 (17)0.0020 (15)−0.0105 (15)−0.0095 (15)
C90.059 (2)0.061 (2)0.044 (2)0.0099 (18)−0.0101 (17)−0.0044 (17)
C100.053 (2)0.044 (2)0.0389 (17)0.0089 (16)−0.0134 (16)−0.0101 (15)
C110.065 (2)0.049 (2)0.053 (2)−0.0041 (18)−0.0205 (18)−0.0095 (17)
C120.076 (3)0.070 (3)0.047 (2)0.009 (2)−0.026 (2)−0.0189 (19)
C130.077 (3)0.060 (2)0.0364 (19)0.010 (2)−0.0092 (19)−0.0085 (17)
C140.066 (2)0.065 (3)0.055 (2)−0.011 (2)−0.007 (2)−0.011 (2)
C150.066 (2)0.069 (3)0.050 (2)−0.003 (2)−0.0174 (19)−0.0199 (19)
Geometric parameters (Å, °) top
Cl2—C161.742 (3)Cl1—C11.738 (3)
S3—C231.750 (3)S1—C81.751 (3)
S3—C241.815 (3)S1—C91.810 (3)
S4—C231.662 (3)S2—C81.657 (3)
N3—C231.337 (4)N1—C81.334 (4)
N3—N41.376 (3)N1—N21.375 (3)
N3—H3A0.8600N1—H10.8600
N4—C221.271 (4)N2—C71.279 (4)
C16—C171.384 (4)C1—C61.377 (5)
C16—C211.384 (5)C1—C21.390 (4)
C17—C181.399 (4)C2—C31.398 (4)
C17—C221.458 (4)C2—C71.455 (4)
C18—C191.380 (5)C3—C41.376 (5)
C18—H180.9300C3—H30.9300
C19—C201.375 (5)C4—C51.371 (5)
C19—H190.9300C4—H40.9300
C20—C211.358 (5)C5—C61.366 (5)
C20—H200.9300C5—H50.9300
C21—H210.9300C6—H60.9300
C22—H220.9300C7—H70.9300
C24—C251.503 (4)C9—C101.512 (4)
C24—H24A0.9700C9—H9A0.9700
C24—H24B0.9700C9—H9B0.9700
C25—C261.373 (4)C10—C151.374 (4)
C25—C301.379 (5)C10—C111.378 (4)
C26—C271.377 (5)C11—C121.384 (5)
C26—H260.9300C11—H110.9300
C27—C281.366 (5)C12—C131.364 (5)
C27—H270.9300C12—H120.9300
C28—C291.355 (5)C13—C141.377 (5)
C28—H280.9300C13—H130.9300
C29—C301.381 (5)C14—C151.382 (5)
C29—H290.9300C14—H140.9300
C30—H300.9300C15—H150.9300
C23—S3—C24101.41 (15)C8—S1—C9101.13 (15)
C23—N3—N4121.2 (2)C8—N1—N2121.0 (2)
C23—N3—H3A119.4C8—N1—H1119.5
N4—N3—H3A119.4N2—N1—H1119.5
C22—N4—N3115.6 (3)C7—N2—N1115.5 (3)
C17—C16—C21122.5 (3)C6—C1—C2121.8 (3)
C17—C16—Cl2120.3 (3)C6—C1—Cl1117.5 (3)
C21—C16—Cl2117.3 (3)C2—C1—Cl1120.7 (3)
C16—C17—C18116.9 (3)C1—C2—C3117.1 (3)
C16—C17—C22122.2 (3)C1—C2—C7121.8 (3)
C18—C17—C22120.9 (3)C3—C2—C7121.0 (3)
C19—C18—C17120.8 (3)C4—C3—C2121.1 (3)
C19—C18—H18119.6C4—C3—H3119.5
C17—C18—H18119.6C2—C3—H3119.5
C20—C19—C18120.3 (3)C5—C4—C3119.9 (4)
C20—C19—H19119.9C5—C4—H4120.1
C18—C19—H19119.9C3—C4—H4120.1
C21—C20—C19120.5 (3)C6—C5—C4120.6 (4)
C21—C20—H20119.8C6—C5—H5119.7
C19—C20—H20119.8C4—C5—H5119.7
C20—C21—C16119.2 (3)C5—C6—C1119.5 (4)
C20—C21—H21120.4C5—C6—H6120.3
C16—C21—H21120.4C1—C6—H6120.3
N4—C22—C17121.6 (3)N2—C7—C2120.9 (3)
N4—C22—H22119.2N2—C7—H7119.6
C17—C22—H22119.2C2—C7—H7119.6
N3—C23—S4121.1 (2)N1—C8—S2121.6 (2)
N3—C23—S3114.0 (2)N1—C8—S1113.4 (2)
S4—C23—S3124.88 (19)S2—C8—S1125.03 (19)
C25—C24—S3108.6 (2)C10—C9—S1108.5 (2)
C25—C24—H24A110.0C10—C9—H9A110.0
S3—C24—H24A110.0S1—C9—H9A110.0
C25—C24—H24B110.0C10—C9—H9B110.0
S3—C24—H24B110.0S1—C9—H9B110.0
H24A—C24—H24B108.4H9A—C9—H9B108.4
C26—C25—C30117.7 (3)C15—C10—C11118.4 (3)
C26—C25—C24121.6 (3)C15—C10—C9121.5 (3)
C30—C25—C24120.8 (3)C11—C10—C9120.0 (3)
C25—C26—C27121.3 (3)C10—C11—C12120.4 (3)
C25—C26—H26119.4C10—C11—H11119.8
C27—C26—H26119.4C12—C11—H11119.8
C28—C27—C26120.1 (3)C13—C12—C11120.6 (3)
C28—C27—H27119.9C13—C12—H12119.7
C26—C27—H27119.9C11—C12—H12119.7
C29—C28—C27119.6 (3)C12—C13—C14119.6 (3)
C29—C28—H28120.2C12—C13—H13120.2
C27—C28—H28120.2C14—C13—H13120.2
C28—C29—C30120.5 (4)C13—C14—C15119.6 (3)
C28—C29—H29119.8C13—C14—H14120.2
C30—C29—H29119.8C15—C14—H14120.2
C25—C30—C29120.9 (3)C10—C15—C14121.3 (3)
C25—C30—H30119.6C10—C15—H15119.3
C29—C30—H30119.6C14—C15—H15119.3
C23—N3—N4—C22−174.7 (3)C8—N1—N2—C7178.3 (3)
C21—C16—C17—C18−0.1 (5)C6—C1—C2—C3−0.5 (5)
Cl2—C16—C17—C18179.5 (3)Cl1—C1—C2—C3−179.9 (3)
C21—C16—C17—C22−178.8 (3)C6—C1—C2—C7178.3 (3)
Cl2—C16—C17—C220.8 (5)Cl1—C1—C2—C7−1.0 (4)
C16—C17—C18—C190.7 (5)C1—C2—C3—C4−0.3 (5)
C22—C17—C18—C19179.4 (3)C7—C2—C3—C4−179.2 (3)
C17—C18—C19—C20−0.9 (5)C2—C3—C4—C50.8 (6)
C18—C19—C20—C210.5 (6)C3—C4—C5—C6−0.6 (6)
C19—C20—C21—C160.1 (6)C4—C5—C6—C1−0.2 (6)
C17—C16—C21—C20−0.3 (6)C2—C1—C6—C50.8 (6)
Cl2—C16—C21—C20−179.9 (3)Cl1—C1—C6—C5−179.8 (3)
N3—N4—C22—C17179.8 (3)N1—N2—C7—C2179.0 (3)
C16—C17—C22—N4−176.4 (3)C1—C2—C7—N2−174.0 (3)
C18—C17—C22—N45.0 (5)C3—C2—C7—N24.8 (5)
N4—N3—C23—S4176.9 (2)N2—N1—C8—S2−179.3 (2)
N4—N3—C23—S3−2.0 (4)N2—N1—C8—S10.3 (4)
C24—S3—C23—N3−179.2 (3)C9—S1—C8—N1177.0 (2)
C24—S3—C23—S41.8 (3)C9—S1—C8—S2−3.5 (3)
C23—S3—C24—C25−174.0 (2)C8—S1—C9—C10−174.1 (2)
S3—C24—C25—C26−80.4 (4)S1—C9—C10—C1571.2 (4)
S3—C24—C25—C3099.9 (3)S1—C9—C10—C11−110.1 (3)
C30—C25—C26—C270.4 (5)C15—C10—C11—C120.9 (5)
C24—C25—C26—C27−179.4 (3)C9—C10—C11—C12−177.8 (3)
C25—C26—C27—C280.2 (6)C10—C11—C12—C13−0.6 (6)
C26—C27—C28—C29−0.1 (6)C11—C12—C13—C140.2 (6)
C27—C28—C29—C30−0.5 (6)C12—C13—C14—C15−0.1 (6)
C26—C25—C30—C29−0.9 (5)C11—C10—C15—C14−0.9 (6)
C24—C25—C30—C29178.8 (3)C9—C10—C15—C14177.8 (3)
C28—C29—C30—C251.0 (6)C13—C14—C15—C100.5 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S40.862.563.405 (3)166
N3—H3A···S20.862.603.451 (3)169
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S40.862.563.405 (3)166
N3—H3A···S20.862.603.451 (3)169
Acknowledgements top

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06–2–08).

references
References top

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