[N'-(5-Bromo-2-oxidobenzyl-idene-κO)-2-chloro-benzohydrazidato-κN',O](methanol-κO)(methano-lato-κO)oxido-vanadium(V).

The V(V) atom in the title complex, [V(C(14)H(8)BrClN(2)O(2))(CH(3)O)O(CH(3)OH)], 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 octa-hedral 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 meth-oxy 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 mol-ecules are linked through inter-molecular 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 = 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

Δρmax = 0.45 e Å−3

Δρmin = −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.

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

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

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

[V(C14H8BrClN2O2)(CH3O)O(CH4O)]	F(000) = 1920
Mr = 481.60	Dx = 1.664 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.09 (2) Å	Cell parameters from 1798 reflections
b = 7.992 (6) Å	θ = 2.3–25.0°
c = 20.163 (14) Å	µ = 2.76 mm−1
β = 121.854 (7)°	T = 298 K
V = 3844 (5) Å3	Block, brown
Z = 8	0.30 × 0.27 × 0.23 mm

Bruker SMART CCD area-detector diffractometer	4081 independent reflections
Radiation source: fine-focus sealed tube	2266 reflections with I > 2σ(I)
graphite	Rint = 0.056
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→35
Tmin = 0.491, Tmax = 0.569	k = −9→9
9750 measured reflections	l = −25→25

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0359P)2] where P = (Fo2 + 2Fc2)/3
4081 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.45 e Å−3
1 restraint	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
V1	0.33992 (3)	0.48966 (10)	0.15964 (4)	0.0355 (2)
Br1	0.05406 (2)	0.13036 (7)	0.00218 (3)	0.05439 (19)
Cl1	0.44356 (6)	0.87745 (17)	0.12452 (7)	0.0663 (4)
H5	0.2799 (16)	0.809 (6)	0.1145 (18)	0.099*
N1	0.27232 (13)	0.5095 (4)	0.04108 (16)	0.0281 (8)
N2	0.28364 (14)	0.5947 (4)	−0.01011 (18)	0.0306 (8)
O1	0.28365 (12)	0.4401 (4)	0.17896 (15)	0.0428 (8)
O2	0.37010 (11)	0.6037 (3)	0.10369 (15)	0.0392 (8)
O3	0.39495 (11)	0.5587 (4)	0.25184 (14)	0.0418 (8)
O4	0.35806 (13)	0.3060 (4)	0.15302 (15)	0.0519 (9)
O5	0.30672 (12)	0.7684 (4)	0.15650 (16)	0.0441 (8)
C1	0.20329 (17)	0.3624 (5)	0.0557 (2)	0.0298 (10)
C2	0.23468 (17)	0.3619 (5)	0.1384 (2)	0.0336 (10)
C3	0.21228 (18)	0.2811 (6)	0.1779 (2)	0.0425 (12)
H3	0.2332	0.2758	0.2321	0.051*
C4	0.15989 (18)	0.2100 (6)	0.1374 (2)	0.0422 (12)
H4	0.1456	0.1574	0.1644	0.051*
C5	0.12819 (16)	0.2159 (5)	0.0566 (2)	0.0351 (11)
C6	0.14949 (17)	0.2896 (5)	0.0161 (2)	0.0346 (11)
H6	0.1281	0.2914	−0.0382	0.042*
C7	0.22241 (18)	0.4472 (5)	0.0110 (2)	0.0331 (10)
H7	0.1975	0.4580	−0.0426	0.040*
C8	0.33695 (17)	0.6358 (5)	0.0297 (2)	0.0309 (10)
C9	0.36154 (17)	0.7211 (5)	−0.0115 (2)	0.0310 (10)
C10	0.40956 (18)	0.8227 (5)	0.0260 (2)	0.0393 (11)
C11	0.43223 (19)	0.8885 (6)	−0.0144 (3)	0.0482 (13)
H11	0.4648	0.9521	0.0118	0.058*
C12	0.4068 (2)	0.8607 (6)	−0.0937 (3)	0.0546 (14)
H12	0.4218	0.9076	−0.1210	0.065*
C13	0.3589 (2)	0.7628 (6)	−0.1326 (3)	0.0530 (13)
H13	0.3420	0.7419	−0.1857	0.064*
C14	0.33694 (17)	0.6971 (5)	−0.0914 (2)	0.0393 (11)
H14	0.3043	0.6340	−0.1180	0.047*
C15	0.44932 (19)	0.4960 (8)	0.3020 (3)	0.0801 (19)
H15A	0.4502	0.3791	0.2918	0.120*
H15B	0.4597	0.5109	0.3552	0.120*
H15C	0.4752	0.5552	0.2932	0.120*
C16	0.3407 (2)	0.9086 (6)	0.1983 (3)	0.0563 (14)
H16A	0.3700	0.8736	0.2494	0.084*
H16B	0.3181	0.9920	0.2030	0.084*
H16C	0.3569	0.9547	0.1706	0.084*

	U11	U22	U33	U12	U13	U23
V1	0.0370 (5)	0.0392 (5)	0.0266 (4)	−0.0050 (4)	0.0141 (4)	0.0019 (4)
Br1	0.0345 (3)	0.0605 (4)	0.0636 (3)	−0.0119 (3)	0.0227 (3)	−0.0005 (3)
Cl1	0.0644 (9)	0.0763 (10)	0.0548 (8)	−0.0275 (8)	0.0292 (7)	−0.0141 (7)
N1	0.032 (2)	0.028 (2)	0.0254 (17)	−0.0033 (17)	0.0157 (16)	0.0003 (16)
N2	0.033 (2)	0.032 (2)	0.0292 (18)	−0.0039 (17)	0.0180 (17)	0.0002 (16)
O1	0.0400 (19)	0.058 (2)	0.0281 (15)	−0.0200 (16)	0.0165 (15)	−0.0009 (15)
O2	0.0330 (17)	0.049 (2)	0.0303 (16)	−0.0054 (15)	0.0130 (14)	0.0083 (14)
O3	0.0318 (18)	0.055 (2)	0.0286 (16)	0.0001 (16)	0.0094 (15)	0.0063 (15)
O4	0.067 (2)	0.042 (2)	0.0389 (18)	0.0046 (18)	0.0226 (17)	0.0038 (15)
O5	0.041 (2)	0.038 (2)	0.0410 (18)	−0.0035 (17)	0.0129 (15)	−0.0027 (16)
C1	0.033 (2)	0.028 (3)	0.028 (2)	−0.001 (2)	0.015 (2)	0.0011 (19)
C2	0.033 (3)	0.034 (3)	0.034 (2)	−0.005 (2)	0.018 (2)	0.000 (2)
C3	0.047 (3)	0.053 (3)	0.032 (2)	−0.012 (3)	0.024 (2)	−0.003 (2)
C4	0.045 (3)	0.045 (3)	0.047 (3)	−0.010 (2)	0.031 (3)	0.001 (2)
C5	0.031 (3)	0.036 (3)	0.038 (2)	−0.002 (2)	0.018 (2)	−0.001 (2)
C6	0.037 (3)	0.033 (3)	0.028 (2)	0.000 (2)	0.013 (2)	0.000 (2)
C7	0.034 (3)	0.037 (3)	0.025 (2)	−0.001 (2)	0.013 (2)	0.000 (2)
C8	0.035 (3)	0.031 (3)	0.033 (2)	0.001 (2)	0.022 (2)	0.002 (2)
C9	0.033 (2)	0.025 (3)	0.037 (2)	0.003 (2)	0.019 (2)	0.002 (2)
C10	0.040 (3)	0.034 (3)	0.043 (3)	0.005 (2)	0.021 (2)	0.004 (2)
C11	0.038 (3)	0.048 (3)	0.064 (3)	−0.009 (2)	0.031 (3)	0.000 (3)
C12	0.060 (3)	0.057 (4)	0.070 (4)	0.002 (3)	0.050 (3)	0.015 (3)
C13	0.054 (3)	0.069 (4)	0.046 (3)	0.001 (3)	0.033 (3)	0.009 (3)
C14	0.032 (3)	0.048 (3)	0.039 (3)	0.005 (2)	0.020 (2)	0.004 (2)
C15	0.039 (3)	0.116 (5)	0.058 (3)	0.015 (4)	0.007 (3)	0.007 (4)
C16	0.066 (4)	0.053 (4)	0.043 (3)	−0.013 (3)	0.024 (3)	−0.007 (3)

V1—O4	1.582 (3)	C4—C5	1.384 (5)
V1—O3	1.765 (3)	C4—H4	0.9300
V1—O1	1.859 (3)	C5—C6	1.374 (5)
V1—O2	1.957 (3)	C6—H6	0.9300
V1—N1	2.134 (3)	C7—H7	0.9300
V1—O5	2.403 (4)	C8—C9	1.496 (5)
Br1—C5	1.896 (4)	C9—C14	1.390 (5)
Cl1—C10	1.746 (4)	C9—C10	1.405 (6)
N1—C7	1.298 (5)	C10—C11	1.375 (6)
N1—N2	1.406 (4)	C11—C12	1.383 (6)
N2—C8	1.314 (5)	C11—H11	0.9300
O1—C2	1.328 (5)	C12—C13	1.386 (6)
O2—C8	1.301 (4)	C12—H12	0.9300
O3—C15	1.406 (5)	C13—C14	1.375 (5)
O5—C16	1.424 (5)	C13—H13	0.9300
O5—H5	0.85 (4)	C14—H14	0.9300
C1—C6	1.409 (5)	C15—H15A	0.9600
C1—C2	1.418 (5)	C15—H15B	0.9600
C1—C7	1.439 (5)	C15—H15C	0.9600
C2—C3	1.404 (5)	C16—H16A	0.9600
C3—C4	1.374 (5)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
O4—V1—O3	103.70 (15)	C5—C6—C1	120.9 (4)
O4—V1—O1	99.61 (15)	C5—C6—H6	119.6
O3—V1—O1	102.39 (13)	C1—C6—H6	119.6
O4—V1—O2	97.29 (14)	N1—C7—C1	123.8 (4)
O3—V1—O2	93.25 (13)	N1—C7—H7	118.1
O1—V1—O2	153.46 (12)	C1—C7—H7	118.1
O4—V1—N1	96.33 (13)	O2—C8—N2	123.2 (3)
O3—V1—N1	157.41 (14)	O2—C8—C9	117.8 (4)
O1—V1—N1	84.17 (13)	N2—C8—C9	119.1 (4)
O2—V1—N1	73.72 (13)	C14—C9—C10	116.9 (4)
O4—V1—O5	174.59 (12)	C14—C9—C8	119.2 (4)
O3—V1—O5	81.36 (12)	C10—C9—C8	123.9 (4)
O1—V1—O5	80.92 (13)	C11—C10—C9	121.1 (4)
O2—V1—O5	80.39 (12)	C11—C10—Cl1	115.6 (4)
N1—V1—O5	78.35 (11)	C9—C10—Cl1	123.4 (3)
C7—N1—N2	116.7 (3)	C10—C11—C12	120.4 (4)
C7—N1—V1	126.8 (3)	C10—C11—H11	119.8
N2—N1—V1	116.5 (2)	C12—C11—H11	119.8
C8—N2—N1	107.4 (3)	C11—C12—C13	119.9 (4)
C2—O1—V1	133.7 (3)	C11—C12—H12	120.0
C8—O2—V1	119.2 (2)	C13—C12—H12	120.0
C15—O3—V1	131.4 (3)	C14—C13—C12	119.0 (4)
C16—O5—V1	125.8 (3)	C14—C13—H13	120.5
C16—O5—H5	105 (4)	C12—C13—H13	120.5
V1—O5—H5	121 (4)	C13—C14—C9	122.7 (4)
C6—C1—C2	118.7 (4)	C13—C14—H14	118.7
C6—C1—C7	118.8 (3)	C9—C14—H14	118.7
C2—C1—C7	122.2 (4)	O3—C15—H15A	109.5
O1—C2—C3	119.7 (4)	O3—C15—H15B	109.5
O1—C2—C1	121.4 (3)	H15A—C15—H15B	109.5
C3—C2—C1	118.8 (4)	O3—C15—H15C	109.5
C4—C3—C2	120.9 (4)	H15A—C15—H15C	109.5
C4—C3—H3	119.6	H15B—C15—H15C	109.5
C2—C3—H3	119.6	O5—C16—H16A	109.5
C3—C4—C5	120.5 (4)	O5—C16—H16B	109.5
C3—C4—H4	119.8	H16A—C16—H16B	109.5
C5—C4—H4	119.8	O5—C16—H16C	109.5
C6—C5—C4	120.2 (4)	H16A—C16—H16C	109.5
C6—C5—Br1	120.0 (3)	H16B—C16—H16C	109.5
C4—C5—Br1	119.8 (3)

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)

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)

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)

Symmetry code: (i) .