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Acta Cryst. (2008). E64, m775-m776    [ doi:10.1107/S1600536808010611 ]

{2,2'-[Ethylenebis(nitrilomethylidyne)]diphenolato-[kappa]4O,N,N',O'}oxidovanadium(IV)

C. Wang, J.-H. Yuan, G. Xie, M.-J. Yu and J. Li

Abstract top

The title compound, [V(C16H14N2O2)O], was synthesized by the reaction of vanadyl(IV) sulfate and N,N'-bis(salicylidene)ethylenediamine under hydrothermal conditions. The asymmetric unit contains two molecules. Each VIV atom is coordinated in a square-pyramidal geometry by two N atoms and two O atoms from a ligand in the basal plane and by an oxide O atom in the apical position. Weak C-H...O hydrogen bonds lead to a three-dimensional supramolecular structure.

Comment top

In the past few decades, there has been increased interest in coordination chemistry and biochemistry of oxovanadium. The main reason is that the function of vanadium in biological system has been recognized, such as the regulation of carbohydrate metabolism (Butler & Walker, 1993; Martinez et al., 2001; Sun et al., 1996). Generally, Schiff base is coordinated to vanadium through O and N atoms (Deng et al., 2007), similar to those in the biological systems. Therefore, it is important to intensively study the relationship of syntheses and structural properties of vanadium-schiff base complexes. We report here the crystal structure of the title compound, a vanadium complex with a schiff-base ligand, N,N'-bis(salicylidene)ethylenediamine (H2salen).

In the asymmetric unit, there are two crystallographically independent molecules (Fig. 1). Each VIV atom is coordinated by two N atoms and two O atoms from a salen ligand in the equatorial plane and an oxido O atom in the apical position, resulting in a five-coordinated square-pyramidal geometry (Table 1). The V ?O bond lengths are 1.582 (2) and 1.583 (2) Å, which are in the normal range. In the crystal structure, though each salen ligand contains two phenyl ring with dihedral angles of 156.3 (4)° and 164.1 (4)°, respectively, there are no π–π interactions between the molecules. In virtue of weak intermolecular C—H···O hydrogen bonds (Table 2), a three-dimensional hydrogen-bonding network is constructed (Fig. 2).

Related literature top

For related literature, see: Butler & Walker (1993); Deng et al. (2007); Martinez et al. (2001); Sun et al. (1996).

Experimental top

A mixture of VOSO4.4H2O (1.175 g, 5 mmol), H2salen (0.725 g, 5 mmol), triethylamine (0.20 mmol) and methanol (0.50 mol) in water was stirred for 1 h, and then heated at 413 K for 3 d in a sealed 25 ml Teflon-lined stainless steel vessel under autogenous pressure. After the reaction mixture was slowly cooled to room temperature at a rate of 5 K h-1, black block crystals of the title compound were collected by filtration, washed with distilled water and dried in air.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97Å (CH2) and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the crystal packing. Hydrogen bonds are drawn as dashed lines.
{2,2'-[Ethylenebis(nitrilomethylidyne)]diphenolato- κ4O,N,N',O'}oxidovanadium(IV) top
Crystal data top
[V(C16H14N2O2)O]F000 = 684
Mr = 333.23Dx = 1.509 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9875 reflections
a = 13.648 (3) Åθ = 3.0–27.5º
b = 6.8085 (14) ŵ = 0.69 mm−1
c = 15.952 (3) ÅT = 293 (2) K
β = 98.24 (3)ºBlock, black
V = 1466.9 (5) Å30.32 × 0.21 × 0.11 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6102 independent reflections
Radiation source: rotating anode4561 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
Detector resolution: 10.0 pixels mm-1θmax = 27.5º
T = 293(2) Kθmin = 3.0º
ω scansh = −17→17
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		k = −8→8
Tmin = 0.809, Tmax = 0.930l = −20→19
14358 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043  w = 1/[σ2(Fo2) + (0.0582P)2 + 0.1081P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.109(Δ/σ)max = 0.006
S = 1.03Δρmax = 0.57 e Å−3
6102 reflectionsΔρmin = −0.43 e Å−3
397 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), 2456 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (2)
Secondary atom site location: difference Fourier map
Crystal data top
[V(C16H14N2O2)O]V = 1466.9 (5) Å3
Mr = 333.23Z = 4
Monoclinic, P21Mo Kα
a = 13.648 (3) ŵ = 0.69 mm−1
b = 6.8085 (14) ÅT = 293 (2) K
c = 15.952 (3) Å0.32 × 0.21 × 0.11 mm
β = 98.24 (3)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6102 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4561 reflections with I > 2σ(I)
Tmin = 0.809, Tmax = 0.930Rint = 0.029
14358 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.57 e Å−3
S = 1.03Δρmin = −0.43 e Å−3
6102 reflectionsAbsolute structure: Flack (1983), 2456 Friedel pairs
397 parametersFlack parameter: 0.01 (2)
2 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
V10.27998 (4)0.86758 (8)0.08474 (3)0.04713 (15)
V20.73287 (4)0.88060 (8)0.57991 (3)0.04920 (15)
N10.2175 (2)1.1335 (4)0.04608 (19)0.0488 (7)
N20.3847 (2)1.0619 (4)0.14130 (17)0.0510 (7)
N30.6545 (3)1.1035 (4)0.62647 (19)0.0596 (8)
N40.7996 (3)1.1273 (4)0.5380 (2)0.0683 (9)
O10.2286 (2)0.7938 (4)0.16192 (18)0.0759 (8)
O20.8039 (3)0.7978 (4)0.65914 (19)0.0841 (9)
O30.20463 (17)0.7577 (3)−0.01603 (15)0.0507 (6)
O40.38881 (19)0.7014 (3)0.06653 (15)0.0565 (6)
O50.61179 (19)0.7339 (3)0.56339 (14)0.0555 (6)
O60.7688 (2)0.7514 (4)0.48130 (16)0.0598 (6)
C10.1221 (3)0.8198 (5)−0.0612 (2)0.0455 (8)
C20.0694 (3)0.6938 (6)−0.1214 (2)0.0602 (10)
H20.09340.5679−0.12830.072*
C3−0.0166 (3)0.7526 (7)−0.1700 (3)0.0677 (11)
H3−0.05040.6651−0.20860.081*
C4−0.0541 (3)0.9403 (6)−0.1627 (2)0.0618 (10)
H4−0.11250.9790−0.19590.074*
C5−0.0043 (3)1.0658 (6)−0.1062 (2)0.0565 (9)
H5−0.02921.1917−0.10110.068*
C60.0835 (3)1.0116 (5)−0.0554 (2)0.0465 (8)
C70.1371 (3)1.1600 (5)−0.0042 (2)0.0508 (8)
H70.11111.2865−0.00790.061*
C80.2716 (3)1.3091 (5)0.0809 (2)0.0613 (10)
H8A0.22531.40920.09370.074*
H8B0.31071.36220.04010.074*
C90.3379 (3)1.2495 (5)0.1604 (3)0.0655 (10)
H9A0.38791.34910.17640.079*
H9B0.29961.23240.20670.079*
C100.4778 (3)1.0407 (5)0.1580 (2)0.0556 (9)
H100.51431.14530.18360.067*
C110.5313 (3)0.8654 (7)0.13993 (19)0.0540 (7)
C120.6340 (3)0.8573 (8)0.1668 (2)0.0697 (10)
H120.66570.96540.19420.084*
C130.6879 (3)0.6955 (8)0.1537 (3)0.0760 (13)
H130.75570.69310.17200.091*
C140.6415 (3)0.5350 (7)0.1133 (2)0.0702 (12)
H140.67800.42270.10580.084*
C150.5407 (3)0.5390 (6)0.0837 (2)0.0584 (9)
H150.51090.43090.05490.070*
C160.4833 (3)0.7039 (5)0.0967 (2)0.0515 (8)
C170.5307 (3)0.7501 (5)0.5992 (2)0.0506 (8)
C180.4647 (3)0.5918 (7)0.5952 (2)0.0599 (9)
H180.47900.47740.56750.072*
C190.3798 (3)0.6014 (8)0.6310 (2)0.0695 (11)
H190.33830.49260.62830.083*
C200.3545 (3)0.7698 (8)0.6711 (3)0.0798 (13)
H200.29640.77480.69520.096*
C210.4155 (3)0.9279 (7)0.6749 (2)0.0707 (12)
H210.39751.04270.70040.085*
C220.5057 (3)0.9226 (5)0.6412 (2)0.0561 (9)
C230.5682 (4)1.0928 (6)0.6496 (2)0.0658 (11)
H230.54451.20430.67380.079*
C240.7116 (5)1.2892 (6)0.6381 (3)0.0991 (19)
H24A0.66691.39880.64190.119*
H24B0.75781.28380.69030.119*
C250.7656 (5)1.3167 (7)0.5658 (4)0.119 (2)
H25A0.72261.37860.51960.143*
H25B0.82201.40230.58190.143*
C260.8629 (4)1.1322 (6)0.4880 (3)0.0761 (12)
H260.89541.25070.48280.091*
C270.8889 (3)0.9717 (6)0.4386 (3)0.0642 (11)
C280.9623 (4)0.9992 (9)0.3841 (3)0.0943 (16)
H280.99601.11800.38490.113*
C290.9831 (4)0.8558 (12)0.3318 (3)0.1094 (19)
H291.03100.87640.29670.131*
C300.9342 (4)0.6780 (9)0.3294 (3)0.0943 (16)
H300.94910.57990.29270.113*
C310.8646 (3)0.6461 (7)0.3805 (3)0.0742 (12)
H310.83270.52510.37850.089*
C320.8391 (3)0.7910 (6)0.4364 (2)0.0571 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0570 (3)0.0332 (2)0.0502 (3)−0.0080 (3)0.0042 (2)−0.0022 (3)
V20.0635 (4)0.0335 (3)0.0486 (3)0.0022 (3)0.0011 (2)−0.0011 (3)
N10.0523 (18)0.0317 (13)0.0634 (17)−0.0046 (11)0.0115 (14)−0.0086 (12)
N20.058 (2)0.0402 (15)0.0517 (15)−0.0092 (13)−0.0015 (14)−0.0046 (13)
N30.086 (3)0.0376 (15)0.0562 (17)−0.0007 (15)0.0125 (17)−0.0066 (13)
N40.070 (2)0.0378 (15)0.099 (3)−0.0036 (14)0.021 (2)−0.0029 (16)
O10.091 (2)0.0718 (18)0.0661 (16)−0.0279 (15)0.0150 (15)0.0010 (13)
O20.107 (2)0.0601 (16)0.0731 (17)0.0166 (16)−0.0276 (17)−0.0025 (14)
O30.0551 (15)0.0352 (11)0.0596 (13)−0.0047 (10)0.0002 (11)−0.0074 (10)
O40.0562 (16)0.0389 (12)0.0703 (15)−0.0014 (11)−0.0049 (12)−0.0058 (12)
O50.0669 (17)0.0444 (13)0.0576 (13)−0.0018 (11)0.0176 (12)−0.0068 (11)
O60.0676 (17)0.0475 (14)0.0673 (15)−0.0011 (12)0.0199 (13)−0.0065 (12)
C10.048 (2)0.0438 (19)0.0456 (16)−0.0060 (13)0.0084 (15)−0.0008 (13)
C20.073 (3)0.048 (2)0.058 (2)−0.0034 (18)0.004 (2)−0.0103 (18)
C30.064 (3)0.077 (3)0.060 (2)−0.013 (2)−0.001 (2)−0.011 (2)
C40.054 (2)0.083 (3)0.0466 (18)0.0014 (19)−0.0004 (16)0.0002 (18)
C50.053 (2)0.062 (2)0.0548 (19)0.0058 (18)0.0100 (17)0.0008 (18)
C60.048 (2)0.0452 (18)0.0482 (17)−0.0047 (14)0.0137 (15)−0.0017 (15)
C70.049 (2)0.0370 (17)0.068 (2)0.0027 (14)0.0119 (18)0.0022 (15)
C80.068 (3)0.0352 (17)0.080 (3)−0.0031 (15)0.007 (2)−0.0101 (16)
C90.076 (3)0.0449 (19)0.073 (2)−0.0094 (18)0.003 (2)−0.0191 (19)
C100.066 (3)0.0445 (19)0.0522 (19)−0.0122 (16)−0.0066 (17)−0.0051 (16)
C110.057 (2)0.0536 (18)0.0494 (15)−0.005 (2)0.0014 (14)0.004 (2)
C120.062 (2)0.087 (3)0.0583 (19)−0.010 (3)0.0032 (17)−0.008 (3)
C130.051 (3)0.115 (4)0.061 (2)0.003 (3)0.0072 (19)0.002 (3)
C140.066 (3)0.093 (3)0.054 (2)0.020 (2)0.017 (2)0.005 (2)
C150.065 (3)0.056 (2)0.0548 (19)0.0054 (18)0.0095 (18)−0.0010 (18)
C160.060 (2)0.0502 (19)0.0432 (17)−0.0002 (16)0.0024 (16)0.0043 (16)
C170.058 (2)0.0517 (19)0.0398 (16)0.0064 (17)−0.0009 (15)0.0057 (15)
C180.060 (3)0.066 (2)0.0493 (19)−0.0012 (19)−0.0042 (17)0.0007 (18)
C190.056 (3)0.090 (3)0.058 (2)−0.010 (2)−0.0083 (19)0.013 (2)
C200.060 (3)0.112 (4)0.067 (2)0.011 (3)0.010 (2)0.024 (3)
C210.075 (3)0.077 (3)0.061 (2)0.026 (2)0.015 (2)0.013 (2)
C220.065 (2)0.058 (2)0.0454 (16)0.0140 (17)0.0061 (16)0.0068 (16)
C230.110 (4)0.0428 (19)0.0494 (19)0.016 (2)0.026 (2)0.0037 (17)
C240.183 (6)0.037 (2)0.085 (3)−0.026 (3)0.045 (4)−0.020 (2)
C250.143 (5)0.051 (3)0.177 (6)−0.023 (3)0.071 (5)−0.035 (3)
C260.073 (3)0.048 (2)0.108 (3)−0.0116 (19)0.013 (3)0.010 (2)
C270.058 (3)0.062 (2)0.073 (3)0.0045 (19)0.010 (2)0.016 (2)
C280.087 (4)0.090 (4)0.111 (4)−0.003 (3)0.032 (3)0.030 (3)
C290.117 (4)0.123 (5)0.101 (3)0.018 (5)0.058 (3)0.015 (4)
C300.108 (4)0.100 (4)0.082 (3)0.008 (3)0.039 (3)0.001 (3)
C310.075 (3)0.076 (3)0.075 (3)0.005 (2)0.023 (2)−0.008 (2)
C320.052 (2)0.059 (2)0.058 (2)0.0048 (17)0.0010 (18)0.0065 (17)
Geometric parameters (Å, °) top
V1—O11.584 (3)C10—H100.9300
V1—O41.922 (3)C11—C121.407 (5)
V1—O31.931 (2)C11—C161.408 (5)
V1—N12.058 (3)C12—C131.358 (7)
V1—N22.059 (3)C12—H120.9300
V2—O21.582 (3)C13—C141.376 (7)
V2—O51.917 (3)C13—H130.9300
V2—O61.926 (2)C14—C151.390 (6)
V2—N32.056 (3)C14—H140.9300
V2—N42.067 (3)C15—C161.401 (5)
N1—C71.275 (4)C15—H150.9300
N1—C81.472 (4)C17—C181.401 (5)
N2—C101.268 (5)C17—C221.418 (5)
N2—C91.480 (5)C18—C191.364 (6)
N3—C231.286 (5)C18—H180.9300
N3—C241.482 (5)C19—C201.381 (7)
N4—C261.258 (5)C19—H190.9300
N4—C251.461 (6)C20—C211.357 (7)
O3—C11.316 (4)C20—H200.9300
O4—C161.311 (4)C21—C221.412 (5)
O5—C171.320 (4)C21—H210.9300
O6—C321.305 (5)C22—C231.434 (6)
C1—C21.406 (5)C23—H230.9300
C1—C61.416 (5)C24—C251.468 (6)
C2—C31.370 (6)C24—H24A0.9700
C2—H20.9300C24—H24B0.9700
C3—C41.388 (6)C25—H25A0.9700
C3—H30.9300C25—H25B0.9700
C4—C51.352 (5)C26—C271.422 (6)
C4—H40.9300C26—H260.9300
C5—C61.396 (5)C27—C321.404 (6)
C5—H50.9300C27—C281.429 (6)
C6—C71.433 (5)C28—C291.341 (8)
C7—H70.9300C28—H280.9300
C8—C91.504 (5)C29—C301.380 (9)
C8—H8A0.9700C29—H290.9300
C8—H8B0.9700C30—C311.355 (6)
C9—H9A0.9700C30—H300.9300
C9—H9B0.9700C31—C321.406 (6)
C10—C111.450 (6)C31—H310.9300
O1—V1—O4111.65 (15)C12—C11—C16119.4 (4)
O1—V1—O3106.38 (13)C12—C11—C10118.7 (4)
O4—V1—O388.68 (10)C16—C11—C10121.9 (3)
O1—V1—N1107.53 (15)C13—C12—C11121.5 (5)
O4—V1—N1140.24 (11)C13—C12—H12119.2
O3—V1—N186.73 (11)C11—C12—H12119.2
O1—V1—N2102.72 (13)C12—C13—C14119.6 (4)
O4—V1—N286.65 (11)C12—C13—H13120.2
O3—V1—N2150.17 (11)C14—C13—H13120.2
N1—V1—N278.34 (12)C13—C14—C15120.7 (4)
O2—V2—O5109.95 (15)C13—C14—H14119.7
O2—V2—O6106.92 (15)C15—C14—H14119.7
O5—V2—O688.01 (11)C14—C15—C16120.8 (4)
O2—V2—N3105.39 (15)C14—C15—H15119.6
O5—V2—N387.24 (12)C16—C15—H15119.6
O6—V2—N3147.00 (12)O4—C16—C15118.5 (3)
O2—V2—N4107.48 (17)O4—C16—C11123.6 (3)
O5—V2—N4142.21 (13)C15—C16—C11117.9 (3)
O6—V2—N486.06 (13)O5—C17—C18119.3 (3)
N3—V2—N478.04 (14)O5—C17—C22123.2 (3)
C7—N1—C8117.5 (3)C18—C17—C22117.5 (3)
C7—N1—V1126.5 (2)C19—C18—C17121.6 (4)
C8—N1—V1115.9 (2)C19—C18—H18119.2
C10—N2—C9120.3 (3)C17—C18—H18119.2
C10—N2—V1129.1 (2)C18—C19—C20121.2 (5)
C9—N2—V1110.6 (2)C18—C19—H19119.4
C23—N3—C24119.9 (4)C20—C19—H19119.4
C23—N3—V2127.4 (3)C21—C20—C19119.1 (4)
C24—N3—V2112.6 (3)C21—C20—H20120.4
C26—N4—C25116.5 (4)C19—C20—H20120.4
C26—N4—V2127.0 (3)C20—C21—C22121.7 (4)
C25—N4—V2116.5 (3)C20—C21—H21119.2
C1—O3—V1130.0 (2)C22—C21—H21119.2
C16—O4—V1132.7 (2)C21—C22—C17118.9 (4)
C17—O5—V2131.0 (2)C21—C22—C23118.9 (4)
C32—O6—V2130.3 (2)C17—C22—C23122.2 (4)
O3—C1—C2119.4 (3)N3—C23—C22125.2 (4)
O3—C1—C6123.9 (3)N3—C23—H23117.4
C2—C1—C6116.6 (3)C22—C23—H23117.4
C3—C2—C1121.4 (4)C25—C24—N3108.9 (4)
C3—C2—H2119.3C25—C24—H24A109.9
C1—C2—H2119.3N3—C24—H24A109.9
C2—C3—C4121.2 (4)C25—C24—H24B109.9
C2—C3—H3119.4N3—C24—H24B109.9
C4—C3—H3119.4H24A—C24—H24B108.3
C5—C4—C3118.8 (4)N4—C25—C24110.1 (4)
C5—C4—H4120.6N4—C25—H25A109.6
C3—C4—H4120.6C24—C25—H25A109.6
C4—C5—C6121.8 (4)N4—C25—H25B109.6
C4—C5—H5119.1C24—C25—H25B109.6
C6—C5—H5119.1H25A—C25—H25B108.2
C5—C6—C1120.2 (3)N4—C26—C27125.5 (4)
C5—C6—C7118.1 (3)N4—C26—H26117.3
C1—C6—C7121.5 (3)C27—C26—H26117.3
N1—C7—C6125.6 (3)C32—C27—C26121.9 (4)
N1—C7—H7117.2C32—C27—C28118.6 (4)
C6—C7—H7117.2C26—C27—C28119.3 (4)
N1—C8—C9108.0 (3)C29—C28—C27120.8 (5)
N1—C8—H8A110.1C29—C28—H28119.6
C9—C8—H8A110.1C27—C28—H28119.6
N1—C8—H8B110.1C28—C29—C30120.8 (5)
C9—C8—H8B110.1C28—C29—H29119.6
H8A—C8—H8B108.4C30—C29—H29119.6
N2—C9—C8106.5 (3)C31—C30—C29120.1 (5)
N2—C9—H9A110.4C31—C30—H30119.9
C8—C9—H9A110.4C29—C30—H30119.9
N2—C9—H9B110.4C30—C31—C32121.8 (5)
C8—C9—H9B110.4C30—C31—H31119.1
H9A—C9—H9B108.6C32—C31—H31119.1
N2—C10—C11124.8 (3)O6—C32—C27124.0 (4)
N2—C10—H10117.6O6—C32—C31118.1 (4)
C11—C10—H10117.6C27—C32—C31117.9 (4)
O1—V1—N1—C7−83.8 (3)C5—C6—C7—N1179.1 (3)
O4—V1—N1—C7106.3 (3)C1—C6—C7—N1−6.8 (5)
O3—V1—N1—C722.3 (3)C7—N1—C8—C9158.5 (3)
N2—V1—N1—C7176.4 (3)V1—N1—C8—C9−21.1 (4)
O1—V1—N1—C895.8 (3)C10—N2—C9—C8129.6 (4)
O4—V1—N1—C8−74.1 (3)V1—N2—C9—C8−48.7 (4)
O3—V1—N1—C8−158.1 (3)N1—C8—C9—N243.8 (4)
N2—V1—N1—C8−4.1 (3)C9—N2—C10—C11−178.4 (3)
O1—V1—N2—C10105.6 (3)V1—N2—C10—C11−0.5 (5)
O4—V1—N2—C10−5.8 (3)N2—C10—C11—C12−175.9 (3)
O3—V1—N2—C10−87.3 (4)N2—C10—C11—C163.8 (6)
N1—V1—N2—C10−148.8 (3)C16—C11—C12—C13−1.4 (6)
O1—V1—N2—C9−76.3 (3)C10—C11—C12—C13178.4 (4)
O4—V1—N2—C9172.3 (2)C11—C12—C13—C140.0 (6)
O3—V1—N2—C990.8 (3)C12—C13—C14—C151.8 (6)
N1—V1—N2—C929.3 (2)C13—C14—C15—C16−2.1 (6)
O2—V2—N3—C23−95.3 (4)V1—O4—C16—C15167.7 (2)
O5—V2—N3—C2314.7 (3)V1—O4—C16—C11−14.0 (5)
O6—V2—N3—C2396.7 (4)C14—C15—C16—O4179.1 (3)
N4—V2—N3—C23159.6 (4)C14—C15—C16—C110.6 (5)
O2—V2—N3—C2480.4 (3)C12—C11—C16—O4−177.2 (3)
O5—V2—N3—C24−169.7 (3)C10—C11—C16—O43.0 (5)
O6—V2—N3—C24−87.6 (4)C12—C11—C16—C151.1 (5)
N4—V2—N3—C24−24.7 (3)C10—C11—C16—C15−178.7 (3)
O2—V2—N4—C2685.3 (4)V2—O5—C17—C18−161.2 (2)
O5—V2—N4—C26−102.8 (4)V2—O5—C17—C2219.7 (5)
O6—V2—N4—C26−21.2 (4)O5—C17—C18—C19−179.8 (3)
N3—V2—N4—C26−172.1 (4)C22—C17—C18—C19−0.7 (5)
O2—V2—N4—C25−98.3 (4)C17—C18—C19—C201.4 (6)
O5—V2—N4—C2573.6 (5)C18—C19—C20—C21−0.1 (6)
O6—V2—N4—C25155.2 (4)C19—C20—C21—C22−2.0 (6)
N3—V2—N4—C254.3 (4)C20—C21—C22—C172.7 (5)
O1—V1—O3—C182.7 (3)C20—C21—C22—C23−178.1 (4)
O4—V1—O3—C1−165.1 (3)O5—C17—C22—C21177.8 (3)
N1—V1—O3—C1−24.6 (3)C18—C17—C22—C21−1.3 (5)
N2—V1—O3—C1−84.2 (3)O5—C17—C22—C23−1.4 (5)
O1—V1—O4—C16−89.2 (3)C18—C17—C22—C23179.5 (3)
O3—V1—O4—C16163.7 (3)C24—N3—C23—C22179.5 (4)
N1—V1—O4—C1680.4 (3)V2—N3—C23—C22−5.1 (6)
N2—V1—O4—C1613.2 (3)C21—C22—C23—N3175.6 (4)
O2—V2—O5—C1783.2 (3)C17—C22—C23—N3−5.2 (6)
O6—V2—O5—C17−169.5 (3)C23—N3—C24—C25−143.1 (5)
N3—V2—O5—C17−22.2 (3)V2—N3—C24—C2540.9 (6)
N4—V2—O5—C17−88.6 (3)C26—N4—C25—C24−166.5 (5)
O2—V2—O6—C32−82.8 (3)V2—N4—C25—C2416.8 (7)
O5—V2—O6—C32166.9 (3)N3—C24—C25—N4−36.1 (7)
N3—V2—O6—C3285.1 (4)C25—N4—C26—C27−164.8 (5)
N4—V2—O6—C3224.2 (3)V2—N4—C26—C2711.6 (7)
V1—O3—C1—C2−166.4 (2)N4—C26—C27—C325.1 (7)
V1—O3—C1—C616.0 (5)N4—C26—C27—C28179.8 (5)
O3—C1—C2—C3−179.7 (4)C32—C27—C28—C290.1 (8)
C6—C1—C2—C3−1.9 (5)C26—C27—C28—C29−174.8 (5)
C1—C2—C3—C41.1 (7)C27—C28—C29—C30−0.1 (9)
C2—C3—C4—C5−0.1 (6)C28—C29—C30—C31−0.3 (10)
C3—C4—C5—C60.0 (6)C29—C30—C31—C320.6 (8)
C4—C5—C6—C1−0.9 (5)V2—O6—C32—C27−17.4 (5)
C4—C5—C6—C7173.3 (3)V2—O6—C32—C31164.6 (3)
O3—C1—C6—C5179.5 (3)C26—C27—C32—O6−3.1 (6)
C2—C1—C6—C51.8 (5)C28—C27—C32—O6−177.8 (4)
O3—C1—C6—C75.5 (5)C26—C27—C32—C31174.9 (4)
C2—C1—C6—C7−172.1 (3)C28—C27—C32—C310.1 (6)
C8—N1—C7—C6168.6 (3)C30—C31—C32—O6177.6 (4)
V1—N1—C7—C6−11.8 (5)C30—C31—C32—C27−0.5 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O4i0.972.553.139 (3)119
C14—H14···O3ii0.932.563.364 (3)145
C24—H24B···O1iii0.972.343.178 (3)144
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z; (iii) −x+1, y+1/2, −z+1.
Table 1
Selected geometric parameters (Å, °) top
V1—O11.584 (3)V2—O21.582 (3)
V1—O41.922 (3)V2—O51.917 (3)
V1—O31.931 (2)V2—O61.926 (2)
V1—N12.058 (3)V2—N32.056 (3)
V1—N22.059 (3)V2—N42.067 (3)
O1—V1—O4111.65 (15)O2—V2—O5109.95 (15)
O1—V1—O3106.38 (13)O2—V2—O6106.92 (15)
O4—V1—O388.68 (10)O5—V2—O688.01 (11)
O1—V1—N1107.53 (15)O2—V2—N3105.39 (15)
O4—V1—N1140.24 (11)O5—V2—N387.24 (12)
O3—V1—N186.73 (11)O6—V2—N3147.00 (12)
O1—V1—N2102.72 (13)O2—V2—N4107.48 (17)
O4—V1—N286.65 (11)O5—V2—N4142.21 (13)
O3—V1—N2150.17 (11)O6—V2—N486.06 (13)
N1—V1—N278.34 (12)N3—V2—N478.04 (14)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C8—H8B···O4i0.972.553.139 (3)119
C14—H14···O3ii0.932.563.364 (3)145
C24—H24B···O1iii0.972.343.178 (3)144
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z; (iii) −x+1, y+1/2, −z+1.
Acknowledgements top

This study was supported in part by the Natural Science Foundation of Heilongjiang Province (grant No. EJG0506–01, B200606 and WC03115) and the Youth Innovation Foundation of Harbin.

references
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