[N′-(5-Bromo-2-oxidobenzyl­idene-κO)-2-chloro­benzohydrazidato-κ2 N′,O](methanol-κO)(methano­lato-κO)oxido­vanadium(V)

Fu-Ming Wang

doi:10.1107/S1600536811008774

. 2011 Mar 12;67(Pt 4):m433–m434. doi: 10.1107/S1600536811008774

[N′-(5-Bromo-2-oxidobenzylidene-κO)-2-chlorobenzohydrazidato-κ² N′,O](methanol-κO)(methanolato-κO)oxidovanadium(V)

Fu-Ming Wang ^a,^*

PMCID: PMC3099792 PMID: 21753958

Abstract

The V^V atom in the title complex, [V(C₁₄H₈BrClN₂O₂)(CH₃O)O(CH₃OH)], is six-coordinated by one phenolate O, one imine N and one enolic O atom of the hydrazone ligand, one oxide O atom, one methanol O atom and one methoxide O atom in a distorted octahedral geometry. The dihedral angle between the two benzene rings of the hydrazone ligand is 13.2 (3)°. The deviation of the V atom towards the oxide O atom from the plane defined by the three donor atoms of the hydrazone ligand and the methoxy O atom is 0.318 (2) Å. Bond lengths are comparable with those observed in similar oxidovanadium(V) complexes with hydrazone ligands. In the crystal, pairs of molecules are linked through intermolecular O—H⋯N hydrogen bonds, forming dimers.

Related literature

For background to hydrazone compounds and their complexes, see: Seena et al. (2008 ▶); Bastos et al. (2008 ▶); Sarkar & Pal (2008 ▶); Nica et al. (2007 ▶). For similar oxidovanadium(V) complexes, see: Kurup et al. (2010 ▶); Rajak et al. (2000 ▶); Grüning et al. (1999 ▶); Mondal et al. (2009 ▶).

Experimental

Crystal data

[V(C₁₄H₈BrClN₂O₂)(CH₃O)O(CH₄O)]
M _r = 481.60
Monoclinic,
a = 28.09 (2) Å
b = 7.992 (6) Å
c = 20.163 (14) Å
β = 121.854 (7)°
V = 3844 (5) Å³
Z = 8
Mo Kα radiation
μ = 2.76 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.491, T _max = 0.569
9750 measured reflections
4081 independent reflections
2266 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.103
S = 1.02
4081 reflections
240 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008774/qm2003sup1.cif

e-67-0m433-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008774/qm2003Isup2.hkl

e-67-0m433-Isup2.hkl^{(200.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected bond lengths (Å).

V1—O4	1.582 (3)
V1—O3	1.765 (3)
V1—O1	1.859 (3)
V1—O2	1.957 (3)
V1—N1	2.134 (3)
V1—O5	2.403 (4)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2ⁱ	0.85 (4)	2.06 (4)	2.906 (4)	178 (5)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Hydrazone compounds and their oxovanadium complexes have received much attention due to their structures and biological properties (Seena et al., 2008; Bastos et al., 2008; Sarkar & Pal, 2008; Nica et al., 2007). In this paper, the title new oxovanadium(V) complex with a hydrazone ligand is reported.

The V^V atom in the title complex, Fig. 1, is six-coordinated by one phenolic O, one imine N, and one enolic O atoms of the hydrazone ligand, by one oxo O atom, and by two O atoms respectively from a methanol molecule and a methoxide ligand, forming a distorted octahedral geometry. The dihedral angle between the two benzene rings of the hydrazone ligand is 13.2 (3)°. The deviation of the V atom from the plane defined by the three donor atoms of the hydrazone ligand and the methoxy O atom towards the oxo O atom is 0.318 (2) Å. The coordinate bond lengths and angles (Table 1) are comparable with those observed in similar oxovanadium(V) complexes (Kurup et al., 2010; Rajak et al., 2000; Grüning et al., 1999; Mondal et al., 2009). In the crystal structure, adjacent two molecules are linked through intermolecular O—H···N hydrogen bonds (Table 2), to form a dimer, as shown in Fig. 2.

Experimental

5-Bromosalicylaldehyde (1 mmol, 0.20 g), 2-chlorobenzohydrazide 1 mmol, 0.17 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 block-like single crystals, suitable for X-ray diffraction, were formed after slow evaporation of the solution in air for a few days.