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

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ISSN: 2056-9890

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

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 VIV 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[Hiromura, M., Nakayama, A., Adachi, Y., Doi, M. & Sakurai, H. (2007). J. Biol. Inorg. Chem. 12, 1275-1287.]); Seena et al. (2008[Seena, E. B., Mathew, N., Kuriakose, M. & Kurup, M. R. P. (2008). Polyhedron, 27, 1455-1462.]); Rosenthal et al. (2008[Rosenthal, E. C. E., Cui, H. L. & Hummert, M. (2008). Inorg. Chem. Commun. 11, 918-920.]); Kurup et al. (2010[Kurup, M. R. P., Seena, E. B. & Kuriakose, M. (2010). Struct. Chem. 21, 599-605.]). For similar oxidovanadium complexes with Schiff bases, see: Li et al. (1988[Li, X., Lah, M. S. & Pecoraro, V. L. (1988). Inorg. Chem. 27, 4657-4664.]); Cornman et al. (1992[Cornman, C. R., Kampf, J., Lah, M. S. & Pecoraro, V. L. (1992). Inorg. Chem. 31, 2035-2043.]); Smith et al. (2000[Smith, T. S., Root, C. A., Kampf, J. W., Rasmussen, P. G. & Pecoraro, V. L. (2000). J. Am. Chem. Soc. 122, 767-775.]); Sarkar & Pal (2006[Sarkar, A. & Pal, S. (2006). Polyhedron, 25, 1689-1694.]).

[Scheme 1]

Experimental

Crystal data
  • [V(C11H13BrClN2O)(C5H7O2)O]

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.429, Tmax = 0.473

  • 7060 measured reflections

  • 3863 independent reflections

  • 2284 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.39 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 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[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL.

Supporting information


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 VIV 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.

Refinement top

Hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, and with Uiso(H) set at 1.2Ueq(C) and 1.5Ueq(Cmethyl).

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
[Figure 1] 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]Dx = 1.626 Mg m3
Mr = 470.64Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 1129 reflections
a = 20.351 (2) Åθ = 2.5–24.5°
b = 12.749 (1) ŵ = 2.76 mm1
c = 7.410 (2) ÅT = 298 K
V = 1922.6 (6) Å3Block, green
Z = 40.37 × 0.33 × 0.32 mm
F(000) = 948
Data collection top
Bruker SMART CCD
diffractometer
3863 independent reflections
Radiation source: fine-focus sealed tube2284 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1526
Tmin = 0.429, Tmax = 0.473k = 1016
7060 measured reflectionsl = 99
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.100 w = 1/[σ2(Fo2)]
S = 0.93(Δ/σ)max < 0.001
3863 reflectionsΔρmax = 0.32 e Å3
230 parametersΔρmin = 0.39 e Å3
1 restraintAbsolute structure: Flack (1983), 1475 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.028 (14)
Crystal data top
[V(C11H13BrClN2O)(C5H7O2)O]V = 1922.6 (6) Å3
Mr = 470.64Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 20.351 (2) ŵ = 2.76 mm1
b = 12.749 (1) ÅT = 298 K
c = 7.410 (2) Å0.37 × 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)
Tmin = 0.429, Tmax = 0.473Rint = 0.052
7060 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.100Δρmax = 0.32 e Å3
S = 0.93Δρmin = 0.39 e Å3
3863 reflectionsAbsolute structure: Flack (1983), 1475 Friedel pairs
230 parametersAbsolute 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
xyzUiso*/Ueq
V10.63268 (4)0.04041 (7)0.00361 (16)0.0381 (3)
Br10.64969 (3)0.21353 (5)0.47589 (10)0.0583 (2)
Cl10.51964 (10)0.50695 (15)0.0592 (3)0.0756 (6)
N10.5724 (2)0.0368 (4)0.1869 (7)0.0380 (12)
N20.6403 (2)0.1505 (4)0.2353 (7)0.0439 (14)
O10.62782 (18)0.0834 (3)0.1510 (6)0.0457 (11)
O20.70569 (18)0.0442 (3)0.1592 (5)0.0476 (11)
O30.71095 (18)0.0874 (3)0.1350 (5)0.0431 (10)
O40.57889 (17)0.1130 (3)0.0917 (6)0.0538 (12)
C10.6018 (2)0.1765 (5)0.1231 (8)0.0343 (14)
C20.6071 (3)0.2535 (5)0.2607 (8)0.0376 (15)
C30.5833 (3)0.3523 (6)0.2406 (9)0.0450 (17)
H30.58970.40190.33100.054*
C40.5496 (3)0.3788 (5)0.0854 (10)0.0501 (17)
C50.5398 (2)0.3065 (5)0.0468 (9)0.0426 (15)
H50.51610.32480.14950.051*
C60.5652 (2)0.2037 (4)0.0296 (11)0.0375 (12)
C70.5528 (3)0.1311 (5)0.1766 (8)0.0402 (15)
H70.52800.15620.27280.048*
C80.5571 (3)0.0253 (5)0.3450 (10)0.0534 (19)
H8A0.52010.07090.32020.064*
H8B0.54560.02030.44490.064*
C90.6162 (3)0.0896 (6)0.3927 (9)0.060 (2)
H9A0.65090.04360.43530.072*
H9B0.60510.13740.48980.072*
C100.7074 (3)0.1882 (6)0.2724 (10)0.072 (2)
H10A0.70690.23190.37790.108*
H10B0.73590.12940.29230.108*
H10C0.72300.22800.17110.108*
C110.5987 (3)0.2457 (5)0.2077 (13)0.076 (2)
H11A0.55510.22470.17340.113*
H11B0.59670.28520.31790.113*
H11C0.61740.28830.11420.113*
C120.8031 (3)0.1328 (6)0.2472 (10)0.064 (2)
H12A0.81170.09540.35720.097*
H12B0.77770.19440.27330.097*
H12C0.84390.15270.19230.097*
C130.7652 (3)0.0633 (5)0.1198 (9)0.0422 (16)
C140.7966 (3)0.0228 (5)0.0327 (9)0.0459 (18)
H140.83940.04470.05560.055*
C150.7685 (3)0.0473 (5)0.1516 (9)0.0459 (17)
C160.8073 (3)0.0823 (6)0.3127 (10)0.069 (2)
H16A0.78480.06200.42090.104*
H16B0.81210.15720.31010.104*
H16C0.85000.05010.31010.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0346 (4)0.0410 (6)0.0388 (6)0.0030 (4)0.0017 (5)0.0003 (6)
Br10.0701 (4)0.0680 (5)0.0367 (3)0.0054 (3)0.0078 (4)0.0003 (5)
Cl10.1159 (14)0.0445 (11)0.0665 (12)0.0281 (11)0.0116 (11)0.0049 (10)
N10.031 (3)0.041 (3)0.042 (3)0.001 (2)0.006 (2)0.001 (3)
N20.040 (3)0.043 (4)0.049 (3)0.004 (3)0.010 (2)0.010 (3)
O10.057 (2)0.043 (3)0.038 (2)0.014 (2)0.018 (2)0.004 (2)
O20.038 (2)0.061 (3)0.044 (3)0.005 (2)0.0084 (19)0.012 (2)
O30.043 (2)0.043 (3)0.043 (3)0.003 (2)0.004 (2)0.006 (2)
O40.042 (2)0.053 (3)0.066 (3)0.002 (2)0.012 (2)0.005 (2)
C10.027 (3)0.040 (4)0.036 (4)0.002 (3)0.005 (2)0.001 (3)
C20.036 (3)0.042 (4)0.035 (4)0.000 (3)0.002 (3)0.002 (3)
C30.052 (4)0.045 (5)0.038 (4)0.004 (3)0.007 (3)0.005 (3)
C40.053 (4)0.042 (4)0.056 (5)0.005 (3)0.011 (3)0.000 (4)
C50.047 (3)0.049 (4)0.033 (4)0.004 (3)0.005 (3)0.003 (4)
C60.032 (2)0.040 (3)0.041 (3)0.003 (2)0.006 (4)0.001 (4)
C70.032 (3)0.052 (5)0.037 (4)0.003 (3)0.008 (3)0.005 (3)
C80.052 (4)0.045 (4)0.063 (5)0.006 (3)0.027 (3)0.017 (4)
C90.068 (4)0.062 (5)0.051 (5)0.012 (4)0.020 (4)0.021 (4)
C100.053 (4)0.076 (6)0.087 (6)0.019 (4)0.008 (4)0.029 (5)
C110.089 (5)0.054 (5)0.084 (6)0.015 (4)0.001 (5)0.006 (5)
C120.055 (4)0.065 (6)0.073 (6)0.008 (4)0.011 (4)0.017 (5)
C130.037 (4)0.041 (4)0.049 (4)0.000 (3)0.001 (3)0.013 (3)
C140.032 (3)0.050 (4)0.056 (5)0.001 (3)0.009 (3)0.006 (3)
C150.051 (4)0.045 (5)0.042 (4)0.017 (4)0.007 (3)0.019 (4)
C160.069 (5)0.090 (6)0.049 (4)0.010 (4)0.030 (4)0.001 (5)
Geometric parameters (Å, º) top
V1—O41.598 (4)C6—C71.452 (9)
V1—O11.952 (4)C7—H70.9300
V1—O31.988 (4)C8—C91.497 (8)
V1—N12.078 (5)C8—H8A0.9700
V1—O22.168 (4)C8—H8B0.9700
V1—N22.222 (5)C9—H9A0.9700
Br1—C21.885 (6)C9—H9B0.9700
Cl1—C41.755 (7)C10—H10A0.9600
N1—C71.268 (7)C10—H10B0.9600
N1—C81.448 (8)C10—H10C0.9600
N2—C101.473 (7)C11—H11A0.9600
N2—C91.484 (8)C11—H11B0.9600
N2—C111.494 (7)C11—H11C0.9600
O1—C11.316 (6)C12—C131.507 (8)
O2—C131.269 (6)C12—H12A0.9600
O3—C151.285 (7)C12—H12B0.9600
C1—C61.399 (9)C12—H12C0.9600
C1—C21.420 (8)C13—C141.397 (8)
C2—C31.358 (8)C14—C151.379 (8)
C3—C41.381 (8)C14—H140.9300
C3—H30.9300C15—C161.499 (9)
C4—C51.360 (8)C16—H16A0.9600
C5—C61.414 (7)C16—H16B0.9600
C5—H50.9300C16—H16C0.9600
O4—V1—O1100.0 (2)C6—C7—H7116.7
O4—V1—O398.39 (19)N1—C8—C9108.6 (5)
O1—V1—O388.92 (17)N1—C8—H8A110.0
O4—V1—N199.13 (19)C9—C8—H8A110.0
O1—V1—N188.30 (18)N1—C8—H8B110.0
O3—V1—N1162.47 (18)C9—C8—H8B110.0
O4—V1—O2173.0 (2)H8A—C8—H8B108.4
O1—V1—O286.82 (17)N2—C9—C8111.4 (6)
O3—V1—O282.86 (15)N2—C9—H9A109.3
N1—V1—O279.70 (17)C8—C9—H9A109.3
O4—V1—N291.3 (2)N2—C9—H9B109.3
O1—V1—N2165.2 (2)C8—C9—H9B109.3
O3—V1—N298.79 (17)H9A—C9—H9B108.0
N1—V1—N280.5 (2)N2—C10—H10A109.5
O2—V1—N281.70 (17)N2—C10—H10B109.5
C7—N1—C8120.0 (5)H10A—C10—H10B109.5
C7—N1—V1126.5 (4)N2—C10—H10C109.5
C8—N1—V1113.3 (4)H10A—C10—H10C109.5
C10—N2—C9109.3 (5)H10B—C10—H10C109.5
C10—N2—C11106.6 (5)N2—C11—H11A109.5
C9—N2—C11110.2 (5)N2—C11—H11B109.5
C10—N2—V1114.5 (4)H11A—C11—H11B109.5
C9—N2—V1104.7 (3)N2—C11—H11C109.5
C11—N2—V1111.6 (4)H11A—C11—H11C109.5
C1—O1—V1131.1 (4)H11B—C11—H11C109.5
C13—O2—V1128.8 (4)C13—C12—H12A109.5
C15—O3—V1131.3 (4)C13—C12—H12B109.5
O1—C1—C6124.5 (5)H12A—C12—H12B109.5
O1—C1—C2118.7 (5)C13—C12—H12C109.5
C6—C1—C2116.7 (6)H12A—C12—H12C109.5
C3—C2—C1122.4 (6)H12B—C12—H12C109.5
C3—C2—Br1120.5 (5)O2—C13—C14123.5 (6)
C1—C2—Br1117.1 (5)O2—C13—C12117.1 (6)
C2—C3—C4119.7 (6)C14—C13—C12119.3 (5)
C2—C3—H3120.1C15—C14—C13124.5 (5)
C4—C3—H3120.1C15—C14—H14117.7
C5—C4—C3120.5 (6)C13—C14—H14117.7
C5—C4—Cl1120.0 (5)O3—C15—C14125.1 (6)
C3—C4—Cl1119.5 (6)O3—C15—C16116.0 (6)
C4—C5—C6120.6 (6)C14—C15—C16118.9 (6)
C4—C5—H5119.7C15—C16—H16A109.5
C6—C5—H5119.7C15—C16—H16B109.5
C1—C6—C5119.9 (6)H16A—C16—H16B109.5
C1—C6—C7122.7 (5)C15—C16—H16C109.5
C5—C6—C7117.4 (6)H16A—C16—H16C109.5
N1—C7—C6126.5 (6)H16B—C16—H16C109.5
N1—C7—H7116.7

Experimental details

Crystal data
Chemical formula[V(C11H13BrClN2O)(C5H7O2)O]
Mr470.64
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)298
a, b, c (Å)20.351 (2), 12.749 (1), 7.410 (2)
V3)1922.6 (6)
Z4
Radiation typeMo Kα
µ (mm1)2.76
Crystal size (mm)0.37 × 0.33 × 0.32
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.429, 0.473
No. of measured, independent and
observed [I > 2σ(I)] reflections
7060, 3863, 2284
Rint0.052
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.100, 0.93
No. of reflections3863
No. of parameters230
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.39
Absolute structureFlack (1983), 1475 Friedel pairs
Absolute structure parameter0.028 (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—O41.598 (4)V1—N12.078 (5)
V1—O11.952 (4)V1—O22.168 (4)
V1—O31.988 (4)V1—N22.222 (5)
O4—V1—O1100.0 (2)O3—V1—O282.86 (15)
O4—V1—O398.39 (19)N1—V1—O279.70 (17)
O1—V1—O388.92 (17)O4—V1—N291.3 (2)
O4—V1—N199.13 (19)O1—V1—N2165.2 (2)
O1—V1—N188.30 (18)O3—V1—N298.79 (17)
O3—V1—N1162.47 (18)N1—V1—N280.5 (2)
O4—V1—O2173.0 (2)O2—V1—N281.70 (17)
O1—V1—O286.82 (17)
 

Acknowledgements

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

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