(Acetyl­acetonato-κ2O,O′)(2-bromo-4-chloro-6-{[2-(dimethyl­amino)­ethyl­imino]­meth­yl}phenolato-κ3N,N′,O)oxidovanadium(IV)

Wang, F.-M.

doi:10.1107/S1600536811015406

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m650

doi:10.1107/S1600536811015406

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(Acetylacetonato-κ²O,O′)(2-bromo-4-chloro-6-{[2-(dimethylamino)ethylimino]methyl}phenolato-κ³N,N′,O)oxidovanadium(IV)

Fu-Ming Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: wfm99999@126.com

(Received 22 April 2011; accepted 24 April 2011; online 29 April 2011)

The V^IV atom in the title complex, [V(C₁₁H₁₃BrClN₂O)(C₅H₇O₂)O], is six-coordinated by one phenolate O, one imino N and one amino N atom of the tridentate anionic Schiff base ligand, by one oxide O atom, and by two O atoms of an acetylacetonate anion, forming a distorted cis-VN₂O₄ octahedral coordination geometry. The deviation of the V atom from the plane defined by the three donor atoms of the Schiff base ligand and one O atom of the acetylacetone ligand towards the oxide O atom is 0.256 (2) Å.

Related literature

For background to oxidovanadium complexes, see: Hiromura et al. (2007 ); Seena et al. (2008 ); Rosenthal et al. (2008 ); Kurup et al. (2010 ). For similar oxidovanadium complexes with Schiff bases, see: Li et al. (1988 ); Cornman et al. (1992 ); Smith et al. (2000 ); Sarkar & Pal (2006 ).

Experimental

Crystal data

[V(C₁₁H₁₃BrClN₂O)(C₅H₇O₂)O]
M_r = 470.64
Orthorhombic, P n a 2₁
a = 20.351 (2) Å
b = 12.749 (1) Å
c = 7.410 (2) Å
V = 1922.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.76 mm⁻¹
T = 298 K
0.37 × 0.33 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.429, T_max = 0.473
7060 measured reflections
3863 independent reflections
2284 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.100
S = 0.93
3863 reflections
230 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 1475 Friedel pairs
Flack parameter: 0.028 (14)

Table 1
Selected geometric parameters (Å, °)

V1—O4	1.598 (4)
V1—O1	1.952 (4)
V1—O3	1.988 (4)
V1—N1	2.078 (5)
V1—O2	2.168 (4)
V1—N2	2.222 (5)

O4—V1—O1	100.0 (2)
O4—V1—O3	98.39 (19)
O1—V1—O3	88.92 (17)
O4—V1—N1	99.13 (19)
O1—V1—N1	88.30 (18)
O3—V1—N1	162.47 (18)
O4—V1—O2	173.0 (2)
O1—V1—O2	86.82 (17)
O3—V1—O2	82.86 (15)
N1—V1—O2	79.70 (17)
O4—V1—N2	91.3 (2)
O1—V1—N2	165.2 (2)
O3—V1—N2	98.79 (17)
N1—V1—N2	80.5 (2)
O2—V1—N2	81.70 (17)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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/S1600536811015406/hb5858sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015406/hb5858Isup2.hkl

checkCIF report

Comment top

Oxovanadium complexes have received much attention due to their structures and biological properties (Hiromura et al., 2007; Seena et al., 2008; Rosenthal et al., 2008; Kurup et al., 2010). In this paper, the title new oxovanadium(IV) complex, (I), with a Schiff base ligand is reported.

The V^IV atom in the title complex, Fig. 1, is six-coordinated by one phenolic O, one imino N, and one amino N atoms of the Schiff base ligand, by one oxo O atom, and by two O atoms of an acetylacetone ligand, forming a distorted octahedral geometry. The deviation of the V atom from the plane defined by the three donor atoms of the Schiff base ligand and one O atom of the acetylacetone ligand towards the oxo O atom is 0.256 (2) Å. The coordinate bond lengths and angles (Table 1) are comparable with those observed in similar oxovanadium(IV) complexes with Schiff bases and acetylacetone ligands (Li et al., 1988; Cornman et al., 1992; Smith et al., 2000; Sarkar & Pal, 2006).

Related literature top

For background to oxidovanadium complexes, see: Hiromura et al. (2007); Seena et al. (2008); Rosenthal et al. (2008); Kurup et al. (2010). For similar oxidovanadium complexes with Schiff bases, see: Li et al. (1988); Cornman et al. (1992); Smith et al. (2000); Sarkar & Pal (2006).

Experimental top

3-Bromo-5-chlorosalicylaldehyde (1 mmol, 0.23 g), N,N-dimethylethane-1,2-diamine (1 mmol, 0.09 g), and VO(acac)₂ (1 mmol, 0.26 g) were mixed in methanol (30 ml). The mixture was boiled under reflux for 2 h, then cooled to room temperature. Green blocks of (I) were formed after slow evaporation of the solution in air for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 the title compound, showing displacement ellipsoids drawn at the 30% probability level.

(Acetylacetonato-κ²O,O')(2-bromo-4-chloro-6-{[2- (dimethylamino)ethylimino]methyl}phenolato- κ³N,N',O)oxidovanadium(IV) top

Crystal data top

[V(C₁₁H₁₃BrClN₂O)(C₅H₇O₂)O]	D_x = 1.626 Mg m⁻³
M_r = 470.64	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1129 reflections
a = 20.351 (2) Å	θ = 2.5–24.5°
b = 12.749 (1) Å	µ = 2.76 mm⁻¹
c = 7.410 (2) Å	T = 298 K
V = 1922.6 (6) Å³	Block, green
Z = 4	0.37 × 0.33 × 0.32 mm
F(000) = 948

Data collection top

Bruker SMART CCD diffractometer	3863 independent reflections
Radiation source: fine-focus sealed tube	2284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→26
T_min = 0.429, T_max = 0.473	k = −10→16
7060 measured reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²)]
S = 0.93	(Δ/σ)_max < 0.001
3863 reflections	Δρ_max = 0.32 e Å⁻³
230 parameters	Δρ_min = −0.39 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1475 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.028 (14)

Crystal data top

[V(C₁₁H₁₃BrClN₂O)(C₅H₇O₂)O]	V = 1922.6 (6) Å³
M_r = 470.64	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 20.351 (2) Å	µ = 2.76 mm⁻¹
b = 12.749 (1) Å	T = 298 K
c = 7.410 (2) Å	0.37 × 0.33 × 0.32 mm

Data collection top

Bruker SMART CCD diffractometer	3863 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2284 reflections with I > 2σ(I)
T_min = 0.429, T_max = 0.473	R_int = 0.052
7060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.32 e Å⁻³
S = 0.93	Δρ_min = −0.39 e Å⁻³
3863 reflections	Absolute structure: Flack (1983), 1475 Friedel pairs
230 parameters	Absolute structure parameter: 0.028 (14)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
V1	0.63268 (4)	−0.04041 (7)	0.00361 (16)	0.0381 (3)
Br1	0.64969 (3)	0.21353 (5)	−0.47589 (10)	0.0583 (2)
Cl1	0.51964 (10)	0.50695 (15)	−0.0592 (3)	0.0756 (6)
N1	0.5724 (2)	0.0368 (4)	0.1869 (7)	0.0380 (12)
N2	0.6403 (2)	−0.1505 (4)	0.2353 (7)	0.0439 (14)
O1	0.62782 (18)	0.0834 (3)	−0.1510 (6)	0.0457 (11)
O2	0.70569 (18)	0.0442 (3)	0.1592 (5)	0.0476 (11)
O3	0.71095 (18)	−0.0874 (3)	−0.1350 (5)	0.0431 (10)
O4	0.57889 (17)	−0.1130 (3)	−0.0917 (6)	0.0538 (12)
C1	0.6018 (2)	0.1765 (5)	−0.1231 (8)	0.0343 (14)
C2	0.6071 (3)	0.2535 (5)	−0.2607 (8)	0.0376 (15)
C3	0.5833 (3)	0.3523 (6)	−0.2406 (9)	0.0450 (17)
H3	0.5897	0.4019	−0.3310	0.054*
C4	0.5496 (3)	0.3788 (5)	−0.0854 (10)	0.0501 (17)
C5	0.5398 (2)	0.3065 (5)	0.0468 (9)	0.0426 (15)
H5	0.5161	0.3248	0.1495	0.051*
C6	0.5652 (2)	0.2037 (4)	0.0296 (11)	0.0375 (12)
C7	0.5528 (3)	0.1311 (5)	0.1766 (8)	0.0402 (15)
H7	0.5280	0.1562	0.2728	0.048*
C8	0.5571 (3)	−0.0253 (5)	0.3450 (10)	0.0534 (19)
H8A	0.5201	−0.0709	0.3202	0.064*
H8B	0.5456	0.0203	0.4449	0.064*
C9	0.6162 (3)	−0.0896 (6)	0.3927 (9)	0.060 (2)
H9A	0.6509	−0.0436	0.4353	0.072*
H9B	0.6051	−0.1374	0.4898	0.072*
C10	0.7074 (3)	−0.1882 (6)	0.2724 (10)	0.072 (2)
H10A	0.7069	−0.2319	0.3779	0.108*
H10B	0.7359	−0.1294	0.2923	0.108*
H10C	0.7230	−0.2280	0.1711	0.108*
C11	0.5987 (3)	−0.2457 (5)	0.2077 (13)	0.076 (2)
H11A	0.5551	−0.2247	0.1734	0.113*
H11B	0.5967	−0.2852	0.3179	0.113*
H11C	0.6174	−0.2883	0.1142	0.113*
C12	0.8031 (3)	0.1328 (6)	0.2472 (10)	0.064 (2)
H12A	0.8117	0.0954	0.3572	0.097*
H12B	0.7777	0.1944	0.2733	0.097*
H12C	0.8439	0.1527	0.1923	0.097*
C13	0.7652 (3)	0.0633 (5)	0.1198 (9)	0.0422 (16)
C14	0.7966 (3)	0.0228 (5)	−0.0327 (9)	0.0459 (18)
H14	0.8394	0.0447	−0.0556	0.055*
C15	0.7685 (3)	−0.0473 (5)	−0.1516 (9)	0.0459 (17)
C16	0.8073 (3)	−0.0823 (6)	−0.3127 (10)	0.069 (2)
H16A	0.7848	−0.0620	−0.4209	0.104*
H16B	0.8121	−0.1572	−0.3101	0.104*
H16C	0.8500	−0.0501	−0.3101	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0346 (4)	0.0410 (6)	0.0388 (6)	0.0030 (4)	0.0017 (5)	−0.0003 (6)
Br1	0.0701 (4)	0.0680 (5)	0.0367 (3)	−0.0054 (3)	0.0078 (4)	−0.0003 (5)
Cl1	0.1159 (14)	0.0445 (11)	0.0665 (12)	0.0281 (11)	0.0116 (11)	0.0049 (10)
N1	0.031 (3)	0.041 (3)	0.042 (3)	−0.001 (2)	0.006 (2)	−0.001 (3)
N2	0.040 (3)	0.043 (4)	0.049 (3)	0.004 (3)	0.010 (2)	0.010 (3)
O1	0.057 (2)	0.043 (3)	0.038 (2)	0.014 (2)	0.018 (2)	0.004 (2)
O2	0.038 (2)	0.061 (3)	0.044 (3)	−0.005 (2)	0.0084 (19)	−0.012 (2)
O3	0.043 (2)	0.043 (3)	0.043 (3)	0.003 (2)	0.004 (2)	−0.006 (2)
O4	0.042 (2)	0.053 (3)	0.066 (3)	−0.002 (2)	−0.012 (2)	−0.005 (2)
C1	0.027 (3)	0.040 (4)	0.036 (4)	−0.002 (3)	−0.005 (2)	−0.001 (3)
C2	0.036 (3)	0.042 (4)	0.035 (4)	0.000 (3)	−0.002 (3)	0.002 (3)
C3	0.052 (4)	0.045 (5)	0.038 (4)	−0.004 (3)	−0.007 (3)	0.005 (3)
C4	0.053 (4)	0.042 (4)	0.056 (5)	0.005 (3)	−0.011 (3)	0.000 (4)
C5	0.047 (3)	0.049 (4)	0.033 (4)	0.004 (3)	−0.005 (3)	−0.003 (4)
C6	0.032 (2)	0.040 (3)	0.041 (3)	0.003 (2)	0.006 (4)	−0.001 (4)
C7	0.032 (3)	0.052 (5)	0.037 (4)	0.003 (3)	0.008 (3)	−0.005 (3)
C8	0.052 (4)	0.045 (4)	0.063 (5)	0.006 (3)	0.027 (3)	0.017 (4)
C9	0.068 (4)	0.062 (5)	0.051 (5)	0.012 (4)	0.020 (4)	0.021 (4)
C10	0.053 (4)	0.076 (6)	0.087 (6)	0.019 (4)	0.008 (4)	0.029 (5)
C11	0.089 (5)	0.054 (5)	0.084 (6)	−0.015 (4)	−0.001 (5)	0.006 (5)
C12	0.055 (4)	0.065 (6)	0.073 (6)	−0.008 (4)	−0.011 (4)	−0.017 (5)
C13	0.037 (4)	0.041 (4)	0.049 (4)	0.000 (3)	0.001 (3)	0.013 (3)
C14	0.032 (3)	0.050 (4)	0.056 (5)	−0.001 (3)	0.009 (3)	0.006 (3)
C15	0.051 (4)	0.045 (5)	0.042 (4)	0.017 (4)	0.007 (3)	0.019 (4)
C16	0.069 (5)	0.090 (6)	0.049 (4)	0.010 (4)	0.030 (4)	−0.001 (5)

Geometric parameters (Å, º) top

V1—O4	1.598 (4)	C6—C7	1.452 (9)
V1—O1	1.952 (4)	C7—H7	0.9300
V1—O3	1.988 (4)	C8—C9	1.497 (8)
V1—N1	2.078 (5)	C8—H8A	0.9700
V1—O2	2.168 (4)	C8—H8B	0.9700
V1—N2	2.222 (5)	C9—H9A	0.9700
Br1—C2	1.885 (6)	C9—H9B	0.9700
Cl1—C4	1.755 (7)	C10—H10A	0.9600
N1—C7	1.268 (7)	C10—H10B	0.9600
N1—C8	1.448 (8)	C10—H10C	0.9600
N2—C10	1.473 (7)	C11—H11A	0.9600
N2—C9	1.484 (8)	C11—H11B	0.9600
N2—C11	1.494 (7)	C11—H11C	0.9600
O1—C1	1.316 (6)	C12—C13	1.507 (8)
O2—C13	1.269 (6)	C12—H12A	0.9600
O3—C15	1.285 (7)	C12—H12B	0.9600
C1—C6	1.399 (9)	C12—H12C	0.9600
C1—C2	1.420 (8)	C13—C14	1.397 (8)
C2—C3	1.358 (8)	C14—C15	1.379 (8)
C3—C4	1.381 (8)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.499 (9)
C4—C5	1.360 (8)	C16—H16A	0.9600
C5—C6	1.414 (7)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600

O4—V1—O1	100.0 (2)	C6—C7—H7	116.7
O4—V1—O3	98.39 (19)	N1—C8—C9	108.6 (5)
O1—V1—O3	88.92 (17)	N1—C8—H8A	110.0
O4—V1—N1	99.13 (19)	C9—C8—H8A	110.0
O1—V1—N1	88.30 (18)	N1—C8—H8B	110.0
O3—V1—N1	162.47 (18)	C9—C8—H8B	110.0
O4—V1—O2	173.0 (2)	H8A—C8—H8B	108.4
O1—V1—O2	86.82 (17)	N2—C9—C8	111.4 (6)
O3—V1—O2	82.86 (15)	N2—C9—H9A	109.3
N1—V1—O2	79.70 (17)	C8—C9—H9A	109.3
O4—V1—N2	91.3 (2)	N2—C9—H9B	109.3
O1—V1—N2	165.2 (2)	C8—C9—H9B	109.3
O3—V1—N2	98.79 (17)	H9A—C9—H9B	108.0
N1—V1—N2	80.5 (2)	N2—C10—H10A	109.5
O2—V1—N2	81.70 (17)	N2—C10—H10B	109.5
C7—N1—C8	120.0 (5)	H10A—C10—H10B	109.5
C7—N1—V1	126.5 (4)	N2—C10—H10C	109.5
C8—N1—V1	113.3 (4)	H10A—C10—H10C	109.5
C10—N2—C9	109.3 (5)	H10B—C10—H10C	109.5
C10—N2—C11	106.6 (5)	N2—C11—H11A	109.5
C9—N2—C11	110.2 (5)	N2—C11—H11B	109.5
C10—N2—V1	114.5 (4)	H11A—C11—H11B	109.5
C9—N2—V1	104.7 (3)	N2—C11—H11C	109.5
C11—N2—V1	111.6 (4)	H11A—C11—H11C	109.5
C1—O1—V1	131.1 (4)	H11B—C11—H11C	109.5
C13—O2—V1	128.8 (4)	C13—C12—H12A	109.5
C15—O3—V1	131.3 (4)	C13—C12—H12B	109.5
O1—C1—C6	124.5 (5)	H12A—C12—H12B	109.5
O1—C1—C2	118.7 (5)	C13—C12—H12C	109.5
C6—C1—C2	116.7 (6)	H12A—C12—H12C	109.5
C3—C2—C1	122.4 (6)	H12B—C12—H12C	109.5
C3—C2—Br1	120.5 (5)	O2—C13—C14	123.5 (6)
C1—C2—Br1	117.1 (5)	O2—C13—C12	117.1 (6)
C2—C3—C4	119.7 (6)	C14—C13—C12	119.3 (5)
C2—C3—H3	120.1	C15—C14—C13	124.5 (5)
C4—C3—H3	120.1	C15—C14—H14	117.7
C5—C4—C3	120.5 (6)	C13—C14—H14	117.7
C5—C4—Cl1	120.0 (5)	O3—C15—C14	125.1 (6)
C3—C4—Cl1	119.5 (6)	O3—C15—C16	116.0 (6)
C4—C5—C6	120.6 (6)	C14—C15—C16	118.9 (6)
C4—C5—H5	119.7	C15—C16—H16A	109.5
C6—C5—H5	119.7	C15—C16—H16B	109.5
C1—C6—C5	119.9 (6)	H16A—C16—H16B	109.5
C1—C6—C7	122.7 (5)	C15—C16—H16C	109.5
C5—C6—C7	117.4 (6)	H16A—C16—H16C	109.5
N1—C7—C6	126.5 (6)	H16B—C16—H16C	109.5
N1—C7—H7	116.7

Experimental details

Crystal data
Chemical formula	[V(C₁₁H₁₃BrClN₂O)(C₅H₇O₂)O]
M_r	470.64
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	20.351 (2), 12.749 (1), 7.410 (2)
V (Å³)	1922.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.76
Crystal size (mm)	0.37 × 0.33 × 0.32

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.429, 0.473
No. of measured, independent and observed [I > 2σ(I)] reflections	7060, 3863, 2284
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.100, 0.93
No. of reflections	3863
No. of parameters	230
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.39
Absolute structure	Flack (1983), 1475 Friedel pairs
Absolute structure parameter	0.028 (14)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

V1—O4	1.598 (4)	V1—N1	2.078 (5)
V1—O1	1.952 (4)	V1—O2	2.168 (4)
V1—O3	1.988 (4)	V1—N2	2.222 (5)

O4—V1—O1	100.0 (2)	O3—V1—O2	82.86 (15)
O4—V1—O3	98.39 (19)	N1—V1—O2	79.70 (17)
O1—V1—O3	88.92 (17)	O4—V1—N2	91.3 (2)
O4—V1—N1	99.13 (19)	O1—V1—N2	165.2 (2)
O1—V1—N1	88.30 (18)	O3—V1—N2	98.79 (17)
O3—V1—N1	162.47 (18)	N1—V1—N2	80.5 (2)
O4—V1—O2	173.0 (2)	O2—V1—N2	81.70 (17)
O1—V1—O2	86.82 (17)

Acknowledgements

This work was supported financially by Dezhou University, People's Republic of China.

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