Di-μ-oxido-bis­[(2-eth­oxy-6-{[2-(2-hy­droxy­ethyl­amino)­ethyl­imino]­meth­yl}phenolato-κ3N,N′,O1)oxidovanadium(V)]

Wang, F.-M.

doi:10.1107/S160053681105094X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages m26-m27

doi:10.1107/S160053681105094X

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Di-μ-oxido-bis[(2-ethoxy-6-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenolato-κ³N,N′,O¹)oxidovanadium(V)]

Fu-Ming Wang ^a ^*

^aKey Laboratory of Coordination Chemistry and Functional Materials in Universities of Shandong, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: wfm99999@126.com

(Received 26 November 2011; accepted 27 November 2011; online 10 December 2011)

In the title centrosymmetric dinuclear dioxidovanadium(V) complex, [V₂(C₁₃H₁₉N₂O₃)₂O₄], the V^V ion is coordinated by an N,N′,O-tridendate 2-ethoxy-6-{[2-(2-hydroxyethylamino)ethylimino]methyl}phenolate ligand and three oxide O atoms, forming a distorted cis-VN₂O₄ octahedral geometry. The bridging O atoms show one short and one long bond to their two attached V^V atoms. The dihedral angle between the benzene ring of the ligand and the V₂O₂ plane is 75.2 (3)°. The deviation of the V^V ion from the plane defined by the three donor atoms of the tridentate ligand and one bridging oxide O atom is 0.337 (2) Å towards the terminal oxide O atom. Two N—H⋯O hydrogen bonds help to establish the conformation of the dimer. In the crystal, the complex molecules are linked by O—H⋯O hydrogen bonds, forming [100] chains.

Related literature

For background to vanadium complexes with Schiff base ligands, see: Kwiatkowski et al. (2006 ); Mondal et al. (2007 ); Rayati et al. (2007 , 2008 ); Mikuriya & Matsunami (2005 ).

Experimental

Crystal data

[V₂(C₁₃H₁₉N₂O₃)₂O₄]
M_r = 668.48
Monoclinic, P 2₁ /n
a = 9.907 (3) Å
b = 6.793 (2) Å
c = 22.279 (3) Å
β = 94.886 (2)°
V = 1493.9 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 298 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.875, T_max = 0.892
11652 measured reflections
3246 independent reflections
2485 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.172
S = 1.05
3246 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.85 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O5	1.634 (2)
V1—O4ⁱ	1.678 (2)
V1—O1	1.918 (2)
V1—N1	2.149 (3)
V1—N2	2.188 (3)
V1—O4	2.351 (2)
Symmetry code: (i) -x+1, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.90 (1)	2.20 (3)	3.033 (4)	154 (5)
O3—H3⋯O5ⁱⁱ	0.82	2.00	2.793 (4)	164
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+2, -z.

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/S160053681105094X/hb6538sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681105094X/hb6538Isup2.hkl

checkCIF report

Comment top

Schiff base compounds and their oxovanadium complexes have received much attention due to their structures and biological properties (Kwiatkowski et al., 2006; Mondal et al., 2007; Rayati et al., 2008; Rayati et al., 2007; Mikuriya & Matsunami, 2005). In this paper, the crystal structure of the title compound, (I), is reported.

The title complex is a centrosymmetric dinuclear dioxovanadium(V) compound, Fig. 1. The inversion center lies in the midpoint of the two V atoms. The V^V ion is coordinated by the phenolic O, imine N, and amine N atoms of a tridendate Schiff base ligand, and three oxo O atoms, forming a distorted octahedral geometry. The dihedral angle between the benzene ring and the V₂O₂ plane is 75.2 (3)°. The deviation of the V^V ion from the plane defined by the three donor atoms of the tridentate ligand and one bridging oxo O atom towards the terminal oxo O atom is 0.337 (2) Å. The coordinate bond lengths (Table 1) are comparable with those observed in similar oxovanadium(V) complexes cited above.

In the crystal, the complex molecules are linked through intermolecular O—H···O hydrogen bonds (Table 2), to form chains along the a axis (Fig. 2).

Related literature top

For background to vanadium complexes with Schiff base ligands, see: Kwiatkowski et al. (2006); Mondal et al. (2007); Rayati et al. (2007, 2008); Mikuriya & Matsunami (2005).

Experimental top

2-Hydroxy-3-ethoxybenzaldehyde (1 mmol, 0.17 g), 2-(2-aminoethylamino)ethanol (1 mmol, 0.10 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. Brown blocks 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 complex with displacement ellipsoids are drawn at the 30% probability level. Unlabeled atoms are at the symmetry position (1-x, 2-y, -z).
	Fig. 2. Molecular packing of the title complex, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Di-µ-oxido-bis[(2-ethoxy-6-{[2-(2- hydroxyethylamino)ethylimino]methyl}phenolato- κ³N,N',O¹)oxidovanadium(V)] top

Crystal data top

[V₂(C₁₃H₁₉N₂O₃)₂O₄]	F(000) = 696
M_r = 668.48	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2450 reflections
a = 9.907 (3) Å	θ = 2.2–24.3°
b = 6.793 (2) Å	µ = 0.69 mm⁻¹
c = 22.279 (3) Å	T = 298 K
β = 94.886 (2)°	Block, brown
V = 1493.9 (7) Å³	0.20 × 0.18 × 0.17 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	3246 independent reflections
Radiation source: fine-focus sealed tube	2485 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scan	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.875, T_max = 0.892	k = −8→8
11652 measured reflections	l = −28→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0952P)² + 1.1945P] where P = (F_o² + 2F_c²)/3
3246 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 1.85 e Å⁻³
1 restraint	Δρ_min = −0.54 e Å⁻³

Crystal data top

[V₂(C₁₃H₁₉N₂O₃)₂O₄]	V = 1493.9 (7) Å³
M_r = 668.48	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.907 (3) Å	µ = 0.69 mm⁻¹
b = 6.793 (2) Å	T = 298 K
c = 22.279 (3) Å	0.20 × 0.18 × 0.17 mm
β = 94.886 (2)°

Data collection top

Bruker SMART CCD diffractometer	3246 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2485 reflections with I > 2σ(I)
T_min = 0.875, T_max = 0.892	R_int = 0.042
11652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.85 e Å⁻³
3246 reflections	Δρ_min = −0.54 e Å⁻³
195 parameters

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	0.62902 (5)	0.97199 (8)	0.04516 (3)	0.0309 (2)
N1	0.6461 (3)	1.2263 (4)	0.10267 (13)	0.0347 (6)
N2	0.7184 (3)	1.1915 (4)	−0.01144 (13)	0.0342 (6)
O1	0.5187 (2)	0.8713 (3)	0.10484 (10)	0.0351 (5)
O2	0.4234 (3)	0.5847 (4)	0.16733 (11)	0.0424 (6)
O3	0.9657 (4)	1.1068 (7)	−0.12850 (17)	0.0885 (12)
H3	1.0385	1.0881	−0.1090	0.133*
O4	0.4359 (2)	1.1593 (3)	0.01421 (10)	0.0351 (5)
O5	0.7765 (2)	0.8771 (4)	0.06738 (12)	0.0432 (6)
C1	0.5369 (3)	0.8873 (5)	0.16463 (14)	0.0329 (7)
C2	0.5987 (3)	1.0530 (5)	0.19418 (16)	0.0368 (8)
C3	0.6073 (4)	1.0645 (6)	0.25808 (17)	0.0456 (9)
H3A	0.6472	1.1735	0.2777	0.055*
C4	0.5572 (4)	0.9157 (7)	0.29065 (17)	0.0504 (10)
H4	0.5622	0.9257	0.3324	0.060*
C5	0.4984 (4)	0.7486 (6)	0.26289 (16)	0.0436 (9)
H5	0.4681	0.6463	0.2861	0.052*
C6	0.4852 (3)	0.7358 (5)	0.19995 (16)	0.0364 (8)
C7	0.3486 (4)	0.4418 (6)	0.19921 (19)	0.0488 (10)
H7A	0.2764	0.5054	0.2187	0.059*
H7B	0.4081	0.3757	0.2297	0.059*
C8	0.2907 (4)	0.2954 (6)	0.1524 (2)	0.0548 (11)
H8A	0.2139	0.3527	0.1297	0.082*
H8B	0.2630	0.1784	0.1722	0.082*
H8C	0.3586	0.2625	0.1258	0.082*
C9	0.6390 (3)	1.2243 (5)	0.16017 (16)	0.0372 (8)
H9	0.6610	1.3394	0.1814	0.045*
C10	0.6735 (4)	1.4124 (5)	0.07187 (18)	0.0425 (9)
H10A	0.7142	1.5073	0.1005	0.051*
H10B	0.5899	1.4676	0.0532	0.051*
C11	0.7699 (4)	1.3655 (6)	0.02438 (17)	0.0459 (9)
H11A	0.7769	1.4780	−0.0020	0.055*
H11B	0.8594	1.3375	0.0436	0.055*
C12	0.8244 (4)	1.0959 (6)	−0.04668 (18)	0.0435 (9)
H12A	0.8988	1.0540	−0.0184	0.052*
H12B	0.7852	0.9785	−0.0659	0.052*
C13	0.8814 (4)	1.2206 (7)	−0.0943 (2)	0.0576 (11)
H13A	0.8079	1.2757	−0.1206	0.069*
H13B	0.9330	1.3286	−0.0754	0.069*
H2	0.646 (3)	1.215 (8)	−0.0374 (18)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0304 (3)	0.0253 (3)	0.0364 (4)	−0.0012 (2)	−0.0004 (2)	−0.0007 (2)
N1	0.0345 (14)	0.0279 (14)	0.0410 (16)	−0.0009 (11)	−0.0006 (12)	0.0005 (12)
N2	0.0301 (14)	0.0284 (15)	0.0437 (17)	−0.0034 (11)	0.0016 (12)	−0.0007 (12)
O1	0.0376 (12)	0.0345 (13)	0.0326 (12)	−0.0052 (10)	−0.0006 (10)	0.0003 (10)
O2	0.0471 (14)	0.0381 (14)	0.0427 (14)	−0.0078 (11)	0.0080 (11)	0.0048 (11)
O3	0.064 (2)	0.126 (4)	0.077 (2)	−0.002 (2)	0.0099 (18)	−0.019 (3)
O4	0.0361 (12)	0.0300 (12)	0.0390 (13)	−0.0020 (10)	0.0019 (10)	−0.0017 (10)
O5	0.0346 (13)	0.0363 (14)	0.0572 (16)	0.0015 (10)	−0.0039 (11)	0.0035 (12)
C1	0.0283 (16)	0.0367 (18)	0.0330 (17)	0.0040 (13)	−0.0011 (13)	0.0007 (14)
C2	0.0327 (17)	0.0387 (19)	0.0380 (19)	0.0019 (14)	−0.0029 (14)	−0.0006 (15)
C3	0.044 (2)	0.053 (2)	0.039 (2)	0.0049 (18)	−0.0068 (16)	−0.0089 (17)
C4	0.048 (2)	0.070 (3)	0.033 (2)	0.004 (2)	−0.0021 (16)	0.0011 (19)
C5	0.0390 (19)	0.050 (2)	0.042 (2)	0.0036 (17)	0.0042 (15)	0.0068 (17)
C6	0.0311 (17)	0.0367 (18)	0.0417 (19)	0.0040 (14)	0.0050 (14)	0.0032 (15)
C7	0.049 (2)	0.041 (2)	0.059 (3)	−0.0024 (17)	0.0194 (19)	0.0069 (18)
C8	0.052 (2)	0.042 (2)	0.072 (3)	−0.0074 (18)	0.018 (2)	0.002 (2)
C9	0.0330 (17)	0.0333 (18)	0.044 (2)	−0.0001 (14)	−0.0042 (14)	−0.0083 (15)
C10	0.045 (2)	0.0276 (18)	0.054 (2)	−0.0045 (15)	0.0008 (17)	−0.0031 (16)
C11	0.048 (2)	0.035 (2)	0.055 (2)	−0.0168 (16)	0.0055 (17)	−0.0032 (17)
C12	0.0335 (17)	0.042 (2)	0.056 (2)	0.0006 (15)	0.0055 (16)	−0.0030 (18)
C13	0.044 (2)	0.070 (3)	0.061 (3)	0.005 (2)	0.0186 (19)	0.010 (2)

Geometric parameters (Å, º) top

V1—O5	1.634 (2)	C3—H3A	0.9300
V1—O4ⁱ	1.678 (2)	C4—C5	1.396 (6)
V1—O1	1.918 (2)	C4—H4	0.9300
V1—N1	2.149 (3)	C5—C6	1.400 (5)
V1—N2	2.188 (3)	C5—H5	0.9300
V1—O4	2.351 (2)	C7—C8	1.518 (6)
N1—C9	1.289 (4)	C7—H7A	0.9700
N1—C10	1.475 (4)	C7—H7B	0.9700
N2—C11	1.492 (4)	C8—H8A	0.9600
N2—C12	1.510 (4)	C8—H8B	0.9600
N2—H2	0.895 (10)	C8—H8C	0.9600
O1—C1	1.333 (4)	C9—H9	0.9300
O2—C6	1.371 (4)	C10—C11	1.518 (5)
O2—C7	1.444 (4)	C10—H10A	0.9700
O3—C13	1.408 (5)	C10—H10B	0.9700
O3—H3	0.8200	C11—H11A	0.9700
O4—V1ⁱ	1.678 (2)	C11—H11B	0.9700
C1—C2	1.417 (5)	C12—C13	1.505 (5)
C1—C6	1.417 (5)	C12—H12A	0.9700
C2—C3	1.421 (5)	C12—H12B	0.9700
C2—C9	1.463 (5)	C13—H13A	0.9700
C3—C4	1.363 (6)	C13—H13B	0.9700

O5—V1—O4ⁱ	107.58 (12)	O2—C6—C5	125.2 (3)
O5—V1—O1	101.35 (12)	O2—C6—C1	114.5 (3)
O4ⁱ—V1—O1	98.86 (10)	C5—C6—C1	120.3 (3)
O5—V1—N1	96.52 (12)	O2—C7—C8	106.4 (3)
O4ⁱ—V1—N1	154.55 (11)	O2—C7—H7A	110.4
O1—V1—N1	83.89 (11)	C8—C7—H7A	110.4
O5—V1—N2	92.77 (12)	O2—C7—H7B	110.4
O4ⁱ—V1—N2	93.15 (11)	C8—C7—H7B	110.4
O1—V1—N2	157.67 (11)	H7A—C7—H7B	108.6
N1—V1—N2	77.33 (11)	C7—C8—H8A	109.5
O5—V1—O4	170.41 (10)	C7—C8—H8B	109.5
O4ⁱ—V1—O4	78.97 (11)	H8A—C8—H8B	109.5
O1—V1—O4	84.19 (9)	C7—C8—H8C	109.5
N1—V1—O4	76.14 (9)	H8A—C8—H8C	109.5
N2—V1—O4	79.70 (9)	H8B—C8—H8C	109.5
C9—N1—C10	119.9 (3)	N1—C9—C2	124.3 (3)
C9—N1—V1	125.2 (2)	N1—C9—H9	117.9
C10—N1—V1	114.8 (2)	C2—C9—H9	117.9
C11—N2—C12	113.4 (3)	N1—C10—C11	107.2 (3)
C11—N2—V1	111.6 (2)	N1—C10—H10A	110.3
C12—N2—V1	109.9 (2)	C11—C10—H10A	110.3
C11—N2—H2	115 (3)	N1—C10—H10B	110.3
C12—N2—H2	107 (3)	C11—C10—H10B	110.3
V1—N2—H2	99 (3)	H10A—C10—H10B	108.5
C1—O1—V1	128.8 (2)	N2—C11—C10	109.4 (3)
C6—O2—C7	117.9 (3)	N2—C11—H11A	109.8
C13—O3—H3	109.5	C10—C11—H11A	109.8
V1ⁱ—O4—V1	101.03 (11)	N2—C11—H11B	109.8
O1—C1—C2	123.0 (3)	C10—C11—H11B	109.8
O1—C1—C6	118.1 (3)	H11A—C11—H11B	108.2
C2—C1—C6	118.8 (3)	C13—C12—N2	116.3 (3)
C1—C2—C3	119.7 (3)	C13—C12—H12A	108.2
C1—C2—C9	121.2 (3)	N2—C12—H12A	108.2
C3—C2—C9	118.6 (3)	C13—C12—H12B	108.2
C4—C3—C2	119.9 (4)	N2—C12—H12B	108.2
C4—C3—H3A	120.0	H12A—C12—H12B	107.4
C2—C3—H3A	120.0	O3—C13—C12	110.3 (4)
C3—C4—C5	121.7 (4)	O3—C13—H13A	109.6
C3—C4—H4	119.2	C12—C13—H13A	109.6
C5—C4—H4	119.2	O3—C13—H13B	109.6
C4—C5—C6	119.6 (4)	C12—C13—H13B	109.6
C4—C5—H5	120.2	H13A—C13—H13B	108.1
C6—C5—H5	120.2

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90 (1)	2.20 (3)	3.033 (4)	154 (5)
O3—H3···O5ⁱⁱ	0.82	2.00	2.793 (4)	164

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[V₂(C₁₃H₁₉N₂O₃)₂O₄]
M_r	668.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.907 (3), 6.793 (2), 22.279 (3)
β (°)	94.886 (2)
V (Å³)	1493.9 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.875, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	11652, 3246, 2485
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.172, 1.05
No. of reflections	3246
No. of parameters	195
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.85, −0.54

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

Selected bond lengths (Å) top

V1—O5	1.634 (2)	V1—N1	2.149 (3)
V1—O4ⁱ	1.678 (2)	V1—N2	2.188 (3)
V1—O1	1.918 (2)	V1—O4	2.351 (2)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.895 (10)	2.20 (3)	3.033 (4)	154 (5)
O3—H3···O5ⁱⁱ	0.82	2.00	2.793 (4)	164

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+2, −z.

Acknowledgements

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

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