metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[1,2-Bis(pyridin-2-ylmeth­­oxy)benzene-κ4N,O,O′,N′]bis­­(nitrato-κO)cobalt(II)

aPharmaceutical College, Heilongjiang University of Traditional Chinese Medicine, Harbin 150040, People's Republic of China, bCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and cEngineering Research Center of Pesticides of Heilongjiang Province, Heilongjiang University, Harbin 150080, People's Republic of China
*Correspondence e-mail: hgf1000@163.com

(Received 5 April 2011; accepted 8 April 2011; online 16 April 2011)

In the title compound, [Co(NO3)2(C18H16N2O2)], the CoII ion is six-coordinated in a distorted octa­hedral environment defined by two O and two N atoms from the ligand and by two O atoms from two nitrate anions. A two-dimensional network parallel to the ab plane is built up by C—H⋯O hydrogen bonds, which link adjacent mol­ecules in the crystal structure.

Related literature

For the synthesis and general backround to flexible pyridyl-based ligands, see: Liu et al. (2010a[Liu, Y., Yan, P.-F., Yu, Y.-H., Hou, G.-F. & Gao, J.-S. (2010a). Cryst. Growth Des. 10, 1559-1568.],b[Liu, Y., Yan, P.-F., Yu, Y.-H., Hou, G.-F. & Gao, J.-S. (2010b). Inorg. Chem. Commun. 13, 630-632.]). For a related structure, see: Yu et al. (2010[Yu, Y.-H., Gao, J.-S., Wang, L.-X., Liu, Y. & Hou, G.-F. (2010). Acta Cryst. E66, m872.]).

[Scheme 1]

Experimental

Crystal data
  • [Co(NO3)2(C18H16N2O2)]

  • Mr = 475.28

  • Triclinic, [P \overline 1]

  • a = 8.6281 (17) Å

  • b = 10.701 (2) Å

  • c = 10.921 (2) Å

  • α = 78.77 (3)°

  • β = 79.04 (3)°

  • γ = 78.55 (3)°

  • V = 957.2 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.95 mm−1

  • T = 291 K

  • 0.24 × 0.21 × 0.19 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.803, Tmax = 0.840

  • 9403 measured reflections

  • 4317 independent reflections

  • 2942 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.098

  • S = 1.04

  • 4317 reflections

  • 280 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6A⋯O3i 0.97 2.46 3.241 (3) 138
C13—H13A⋯O6ii 0.97 2.42 3.296 (4) 150
C17—H17⋯O7iii 0.93 2.58 3.469 (4) 160
C18—H18⋯O7 0.93 2.56 2.970 (4) 107
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z; (iii) -x+1, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In recent, our group has employed the flexible N-heterocyclic ligands reacting with transition metal to construct several supramolecular architectures (Liu et al. 2010a, 2010b; Yu et al. 2010). As a part of our continuing work for bipyridyl aromatic ligands, we report the crystal structure of the title compound here.

1,2-Bis(pyridin-2-ylmethoxy)benzene molecule act as a chelating ligand to coordinate with CoII ion forming a discrete structure. Two nitrate anions also coordinate to the center CoII ion, resulting the CoII ion is six-coordinated in a distorted octahedral environment (Figure 1).

A two-dimensional network, which parallel to ab plane, is built up by the C—H···O hydrogen bonds linking these isolated complexes (Figure 2, Tbale 1).

Related literature top

For the synthesis and general backround to flexible pyridyl-based ligands, see: Liu et al. (2010a,b). For a related structure, see: Yu et al. (2010).

Experimental top

The 1,2-Bis(pyridin-2-ylmethoxy)benzene was synthesized by the reaction of ο-dihydroxybenzene and 2-chloromethylpyridine hydrochloride under nitrogen atmosphere and alkaline condition (Liu et al., 2010a). Title ligand (0.58 g, 2 mmol) and Co(NO3)2.H2O (0.44 g, 2 mmol) were dissolved in 15 ml e thanol, and then the mixture keep stirring for 30 minute. The resulting solution was filtered, and the filtrate was allowed to stand in a desiccator at room temperature for several days. Red block crystals were obtained.

Refinement top

The reflection data (4 0 5) had been omitted in the refinement. H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C), C—H = 0.97 Å (methene C), and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound, showing the atom-labellingscheme and displacement ellipsoids drawn at 50% probability level.
[Figure 2] Fig. 2. A partial packing view, showing the planar structure parallelled ab plane. Dashed lines indicate the hydrogen bonds and, no involving H atoms have been omitted for clarity.
[1,2-Bis(pyridin-2-ylmethoxy)benzene- κ4N,O,O',N']bis(nitrato-κO)cobalt(II) top
Crystal data top
[Co(NO3)2(C18H16N2O2)]Z = 2
Mr = 475.28F(000) = 486
Triclinic, P1Dx = 1.649 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6281 (17) ÅCell parameters from 6221 reflections
b = 10.701 (2) Åθ = 3.0–27.5°
c = 10.921 (2) ŵ = 0.95 mm1
α = 78.77 (3)°T = 291 K
β = 79.04 (3)°Block, red
γ = 78.55 (3)°0.24 × 0.21 × 0.19 mm
V = 957.2 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4317 independent reflections
Radiation source: fine-focus sealed tube2942 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1111
Tmin = 0.803, Tmax = 0.840k = 1313
9403 measured reflectionsl = 1412
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0345P)2 + 0.4119P]
where P = (Fo2 + 2Fc2)/3
4317 reflections(Δ/σ)max < 0.001
280 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Co(NO3)2(C18H16N2O2)]γ = 78.55 (3)°
Mr = 475.28V = 957.2 (3) Å3
Triclinic, P1Z = 2
a = 8.6281 (17) ÅMo Kα radiation
b = 10.701 (2) ŵ = 0.95 mm1
c = 10.921 (2) ÅT = 291 K
α = 78.77 (3)°0.24 × 0.21 × 0.19 mm
β = 79.04 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4317 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2942 reflections with I > 2σ(I)
Tmin = 0.803, Tmax = 0.840Rint = 0.033
9403 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.30 e Å3
4317 reflectionsΔρmin = 0.44 e Å3
280 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
xyzUiso*/Ueq
C10.0687 (3)0.3713 (3)0.2950 (3)0.0486 (7)
H10.00150.42860.25790.058*
C20.2202 (3)0.4199 (3)0.3487 (3)0.0554 (7)
H20.25120.50830.34840.066*
C30.3259 (3)0.3361 (3)0.4030 (3)0.0555 (8)
H30.42890.36670.44080.067*
C40.2763 (3)0.2067 (3)0.4004 (2)0.0477 (7)
H40.34590.14840.43560.057*
C50.1215 (3)0.1633 (2)0.3447 (2)0.0372 (5)
C60.0689 (3)0.0228 (2)0.3402 (3)0.0443 (6)
H6A0.07680.02540.42550.053*
H6B0.13830.00670.29560.053*
C70.1666 (3)0.1270 (2)0.2818 (3)0.0440 (6)
C80.0924 (3)0.2336 (3)0.3200 (3)0.0506 (7)
H80.01790.22430.34520.061*
C90.1852 (4)0.3553 (3)0.3201 (3)0.0591 (8)
H90.13650.42830.34500.071*
C100.3477 (4)0.3692 (3)0.2842 (3)0.0573 (8)
H100.40860.45150.28680.069*
C110.4228 (3)0.2613 (3)0.2436 (3)0.0504 (7)
H110.53300.27060.21770.060*
C120.3307 (3)0.1406 (2)0.2426 (2)0.0425 (6)
C130.5543 (3)0.0297 (3)0.1678 (3)0.0501 (7)
H13A0.59460.07890.09920.060*
H13B0.60770.07160.23920.060*
C140.5874 (3)0.1051 (3)0.1271 (2)0.0431 (6)
C150.7396 (3)0.1244 (3)0.0648 (3)0.0591 (8)
H150.81750.05460.04490.071*
C160.7728 (4)0.2473 (4)0.0331 (3)0.0686 (10)
H160.87340.26240.00890.082*
C170.6556 (4)0.3484 (3)0.0643 (3)0.0654 (9)
H170.67680.43250.04630.078*
C180.5062 (4)0.3233 (3)0.1226 (3)0.0542 (7)
H180.42650.39240.14140.065*
Co10.22927 (4)0.16895 (4)0.22727 (4)0.04752 (14)
N10.0169 (2)0.2441 (2)0.29360 (19)0.0399 (5)
N20.4706 (2)0.2029 (2)0.15346 (19)0.0417 (5)
N30.2919 (2)0.2222 (3)0.4483 (2)0.0494 (6)
N40.1734 (3)0.2913 (3)0.0118 (3)0.0585 (7)
O10.0897 (2)0.00028 (17)0.2786 (2)0.0574 (6)
O20.3876 (2)0.02515 (17)0.2020 (2)0.0546 (5)
O30.2818 (2)0.1180 (2)0.41373 (19)0.0591 (5)
O40.3220 (3)0.2203 (3)0.5536 (2)0.0902 (9)
O50.2706 (3)0.3219 (2)0.3710 (2)0.0711 (6)
O60.1839 (2)0.1745 (2)0.04378 (19)0.0600 (5)
O70.1811 (3)0.3725 (3)0.0520 (3)0.0840 (8)
O80.1569 (3)0.3154 (3)0.1235 (2)0.1009 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0457 (15)0.0407 (15)0.0580 (17)0.0091 (12)0.0044 (13)0.0063 (13)
C20.0514 (16)0.0496 (17)0.0618 (18)0.0043 (13)0.0104 (14)0.0126 (14)
C30.0373 (14)0.070 (2)0.0531 (17)0.0016 (14)0.0013 (13)0.0109 (15)
C40.0342 (13)0.0594 (18)0.0448 (15)0.0084 (12)0.0036 (11)0.0005 (13)
C50.0324 (12)0.0445 (14)0.0340 (12)0.0096 (10)0.0045 (10)0.0021 (11)
C60.0319 (12)0.0455 (15)0.0522 (15)0.0147 (11)0.0007 (11)0.0009 (12)
C70.0453 (14)0.0359 (14)0.0508 (15)0.0122 (11)0.0026 (12)0.0061 (12)
C80.0515 (15)0.0435 (16)0.0602 (17)0.0209 (13)0.0058 (13)0.0064 (13)
C90.080 (2)0.0359 (15)0.068 (2)0.0218 (15)0.0189 (17)0.0047 (14)
C100.074 (2)0.0354 (15)0.0637 (19)0.0036 (14)0.0168 (16)0.0099 (13)
C110.0520 (16)0.0444 (16)0.0535 (16)0.0015 (13)0.0103 (13)0.0094 (13)
C120.0447 (14)0.0338 (13)0.0496 (15)0.0117 (11)0.0034 (12)0.0070 (11)
C130.0313 (12)0.0565 (17)0.0586 (17)0.0069 (12)0.0021 (12)0.0053 (14)
C140.0326 (12)0.0611 (17)0.0369 (13)0.0166 (12)0.0047 (10)0.0032 (12)
C150.0362 (14)0.091 (2)0.0493 (16)0.0195 (15)0.0026 (12)0.0036 (16)
C160.0487 (17)0.106 (3)0.0537 (18)0.0442 (19)0.0098 (14)0.0134 (19)
C170.076 (2)0.075 (2)0.0544 (18)0.0507 (19)0.0187 (16)0.0144 (16)
C180.0658 (18)0.0554 (18)0.0467 (15)0.0321 (15)0.0092 (14)0.0016 (13)
Co10.03625 (19)0.0440 (2)0.0571 (2)0.01247 (15)0.00876 (16)0.00555 (17)
N10.0346 (10)0.0406 (12)0.0432 (12)0.0088 (9)0.0029 (9)0.0040 (9)
N20.0417 (11)0.0469 (13)0.0372 (11)0.0196 (10)0.0020 (9)0.0005 (9)
N30.0327 (11)0.0671 (17)0.0470 (14)0.0159 (11)0.0004 (10)0.0050 (13)
N40.0333 (11)0.0727 (19)0.0576 (16)0.0093 (12)0.0030 (11)0.0084 (14)
O10.0376 (9)0.0350 (10)0.0902 (15)0.0131 (8)0.0185 (10)0.0082 (10)
O20.0345 (9)0.0371 (10)0.0862 (14)0.0092 (8)0.0084 (9)0.0098 (9)
O30.0589 (12)0.0505 (12)0.0645 (13)0.0210 (10)0.0053 (10)0.0035 (10)
O40.0743 (16)0.159 (3)0.0483 (13)0.0396 (17)0.0144 (12)0.0176 (15)
O50.0630 (13)0.0517 (13)0.0877 (16)0.0118 (10)0.0046 (12)0.0102 (12)
O60.0488 (11)0.0600 (13)0.0646 (13)0.0102 (10)0.0015 (10)0.0032 (11)
O70.0663 (15)0.0733 (17)0.114 (2)0.0218 (13)0.0009 (14)0.0223 (16)
O80.0746 (16)0.156 (3)0.0518 (14)0.0088 (17)0.0101 (12)0.0219 (16)
Geometric parameters (Å, º) top
C1—N11.347 (3)C13—O21.410 (3)
C1—C21.371 (4)C13—C141.492 (4)
C1—H10.9300C13—H13A0.9700
C2—C31.379 (4)C13—H13B0.9700
C2—H20.9300C14—N21.335 (3)
C3—C41.370 (4)C14—C151.394 (3)
C3—H30.9300C15—C161.366 (5)
C4—C51.388 (3)C15—H150.9300
C4—H40.9300C16—C171.373 (5)
C5—N11.343 (3)C16—H160.9300
C5—C61.489 (4)C17—C181.378 (4)
C6—O11.403 (3)C17—H170.9300
C6—H6A0.9700C18—N21.348 (3)
C6—H6B0.9700C18—H180.9300
C7—C81.375 (4)Co1—O62.101 (2)
C7—C121.386 (4)Co1—O32.114 (2)
C7—O11.388 (3)Co1—N12.156 (2)
C8—C91.387 (4)Co1—N22.159 (2)
C8—H80.9300Co1—O22.2825 (19)
C9—C101.369 (4)Co1—O12.2876 (19)
C9—H90.9300N3—O41.223 (3)
C10—C111.392 (4)N3—O51.230 (3)
C10—H100.9300N3—O31.268 (3)
C11—C121.374 (4)N4—O81.226 (3)
C11—H110.9300N4—O71.233 (4)
C12—O21.382 (3)N4—O61.272 (3)
N1—C1—C2123.0 (3)C16—C15—C14119.1 (3)
N1—C1—H1118.5C16—C15—H15120.5
C2—C1—H1118.5C14—C15—H15120.5
C1—C2—C3119.1 (3)C15—C16—C17119.1 (3)
C1—C2—H2120.4C15—C16—H16120.5
C3—C2—H2120.4C17—C16—H16120.5
C4—C3—C2118.7 (3)C16—C17—C18119.1 (3)
C4—C3—H3120.7C16—C17—H17120.5
C2—C3—H3120.7C18—C17—H17120.5
C3—C4—C5119.5 (3)N2—C18—C17122.8 (3)
C3—C4—H4120.2N2—C18—H18118.6
C5—C4—H4120.2C17—C18—H18118.6
N1—C5—C4122.1 (2)O6—Co1—O3167.12 (8)
N1—C5—C6118.6 (2)O6—Co1—N192.66 (8)
C4—C5—C6119.3 (2)O3—Co1—N191.78 (8)
O1—C6—C5110.0 (2)O6—Co1—N290.83 (8)
O1—C6—H6A109.7O3—Co1—N291.54 (8)
C5—C6—H6A109.7N1—Co1—N2149.17 (8)
O1—C6—H6B109.7O6—Co1—O285.45 (9)
C5—C6—H6B109.7O3—Co1—O283.28 (9)
H6A—C6—H6B108.2N1—Co1—O2139.03 (8)
C8—C7—C12120.7 (2)N2—Co1—O271.79 (8)
C8—C7—O1125.1 (2)O6—Co1—O184.09 (9)
C12—C7—O1114.2 (2)O3—Co1—O185.79 (8)
C7—C8—C9118.7 (3)N1—Co1—O172.04 (7)
C7—C8—H8120.6N2—Co1—O1138.79 (8)
C9—C8—H8120.6O2—Co1—O167.05 (6)
C10—C9—C8120.7 (3)C5—N1—C1117.6 (2)
C10—C9—H9119.6C5—N1—Co1120.29 (17)
C8—C9—H9119.6C1—N1—Co1121.93 (17)
C9—C10—C11120.6 (3)C14—N2—C18117.5 (2)
C9—C10—H10119.7C14—N2—Co1120.61 (17)
C11—C10—H10119.7C18—N2—Co1121.64 (19)
C12—C11—C10118.6 (3)O4—N3—O5123.2 (3)
C12—C11—H11120.7O4—N3—O3120.1 (3)
C10—C11—H11120.7O5—N3—O3116.7 (2)
C11—C12—O2125.1 (2)O8—N4—O7124.7 (3)
C11—C12—C7120.6 (2)O8—N4—O6118.6 (3)
O2—C12—C7114.3 (2)O7—N4—O6116.7 (3)
O2—C13—C14108.7 (2)C7—O1—C6117.91 (19)
O2—C13—H13A110.0C7—O1—Co1121.70 (15)
C14—C13—H13A110.0C6—O1—Co1118.14 (15)
O2—C13—H13B110.0C12—O2—C13118.1 (2)
C14—C13—H13B110.0C12—O2—Co1121.94 (14)
H13A—C13—H13B108.3C13—O2—Co1118.68 (16)
N2—C14—C15122.4 (3)N3—O3—Co1106.43 (17)
N2—C14—C13118.6 (2)N4—O6—Co1107.7 (2)
C15—C14—C13118.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O3i0.972.463.241 (3)138
C13—H13A···O6ii0.972.423.296 (4)150
C17—H17···O7iii0.932.583.469 (4)160
C18—H18···O70.932.562.970 (4)107
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Co(NO3)2(C18H16N2O2)]
Mr475.28
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)8.6281 (17), 10.701 (2), 10.921 (2)
α, β, γ (°)78.77 (3), 79.04 (3), 78.55 (3)
V3)957.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.95
Crystal size (mm)0.24 × 0.21 × 0.19
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.803, 0.840
No. of measured, independent and
observed [I > 2σ(I)] reflections
9403, 4317, 2942
Rint0.033
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.098, 1.04
No. of reflections4317
No. of parameters280
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.44

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O3i0.972.463.241 (3)138
C13—H13A···O6ii0.972.423.296 (4)150
C17—H17···O7iii0.932.583.469 (4)160
C18—H18···O70.932.562.970 (4)107
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z; (iii) x+1, y+1, z.
 

Acknowledgements

The authors thank the Special Funds for the Research of Scientific and Technological Innovative Talents of Harbin Municipal Science and Technology Bureau (2009­RFXXG027), the Science and Technology Planning Project of Heilongjiang Province (GZ08A401) and Heilongjiang University for supporting this study.

References

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