(Acetyl-acetonato-κO,O')(2-bromo-4-chloro-6-{[2-(dimethyl-amino)-ethyl-imino]-meth-yl}phenolato-κN,N',O)oxidovanadium(IV).

The V(IV) atom in the title complex, [V(C(11)H(13)BrClN(2)O)(C(5)H(7)O(2))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 acetyl-acetonate anion, forming a distorted cis-VN(2)O(4) octa-hedral 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 acetyl-acetone 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 = 470.64

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 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 ▶), 1475 Friedel pairs

Flack parameter: 0.028 (14)

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/S1600536811015406/hb5858sup1.cif

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

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

[V(C11H13BrClN2O)(C5H7O2)O]	Dx = 1.626 Mg m−3
Mr = 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

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

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(Fo2)]
S = 0.93	(Δ/σ)max < 0.001
3863 reflections	Δρmax = 0.32 e Å−3
230 parameters	Δρmin = −0.39 e Å−3
1 restraint	Absolute structure: Flack (1983), 1475 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.028 (14)

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	0.63268 (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*

	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)

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

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)