(4-Bromo-2-{[2-(morpholin-4-yl)ethyl-imino]-meth-yl}phenolato)dioxido-vanadium(V).

In the title mononuclear dioxidovanadium(V) complex, [V(C(13)H(16)BrN(2)O(2))O(2)], the V(V) atom is five-coordinated by one phenolate O, one imine N and one morpholine N atom of the Schiff base ligand, and by two oxide O atoms, forming a distorted square-pyramidal geometry. In the crystal, weak C-H⋯O inter-actions and a short Br⋯Br contact [3.4597 (12) Å] are observed.

Related literature

For related Schiff base complexes that we have reported recently, see: Wang (2009 ▶, 2011 ▶); Wang & Ye (2011 ▶). For similar oxidovanadium(V) complexes, see: Xie et al. (2004 ▶); Gao et al. (2005 ▶); Hartung et al. (2007 ▶); Romanowski et al. (2009 ▶).

Experimental

Crystal data

[V(C13H16BrN2O2)O2]

M = 395.13

Monoclinic,

a = 21.372 (3) Å

b = 6.0892 (15) Å

c = 11.372 (3) Å

β = 97.248 (2)°

V = 1468.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.41 mm−1

T = 298 K

0.17 × 0.13 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.595, T max = 0.665

11267 measured reflections

3204 independent reflections

2058 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.096

S = 1.02

3204 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.62 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 datablock(s) global, I. DOI: 10.1107/S1600536811035240/is2767sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035240/is2767Isup2.hkl

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

[V(C13H16BrN2O2)O2]	F(000) = 792
Mr = 395.13	Dx = 1.788 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2133 reflections
a = 21.372 (3) Å	θ = 2.7–25.1°
b = 6.0892 (15) Å	µ = 3.41 mm−1
c = 11.372 (3) Å	T = 298 K
β = 97.248 (2)°	Block, yellow
V = 1468.0 (5) Å3	0.17 × 0.13 × 0.13 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	2058 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→27
Tmin = 0.595, Tmax = 0.665	k = −7→7
11267 measured reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0418P)2] where P = (Fo2 + 2Fc2)/3
3204 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.28158 (3)	0.31216 (10)	0.45502 (5)	0.02930 (17)
Br1	0.01304 (2)	−0.30291 (9)	0.10991 (4)	0.06124 (19)
N1	0.23304 (13)	0.4015 (4)	0.2854 (2)	0.0255 (6)
N2	0.34664 (13)	0.5238 (4)	0.3783 (2)	0.0253 (7)
O1	0.21270 (13)	0.1134 (5)	0.4562 (2)	0.0482 (7)
O2	0.47871 (12)	0.5987 (5)	0.3519 (3)	0.0527 (8)
O3	0.33864 (12)	0.1419 (4)	0.4953 (2)	0.0442 (7)
O4	0.27296 (13)	0.4752 (4)	0.5634 (2)	0.0473 (7)
C1	0.15474 (16)	0.1138 (6)	0.2635 (3)	0.0290 (8)
C2	0.17008 (17)	0.0235 (6)	0.3773 (3)	0.0329 (9)
C3	0.13930 (18)	−0.1665 (6)	0.4067 (3)	0.0407 (10)
H3	0.1501	−0.2298	0.4809	0.049*
C4	0.09347 (19)	−0.2617 (6)	0.3282 (4)	0.0431 (10)
H4	0.0730	−0.3876	0.3496	0.052*
C5	0.07759 (18)	−0.1697 (7)	0.2164 (3)	0.0401 (10)
C6	0.10726 (17)	0.0147 (6)	0.1835 (3)	0.0372 (9)
H6	0.0962	0.0748	0.1085	0.045*
C7	0.18586 (17)	0.3060 (6)	0.2271 (3)	0.0307 (8)
H7	0.1702	0.3667	0.1542	0.037*
C8	0.25689 (16)	0.5992 (6)	0.2292 (3)	0.0301 (8)
H8A	0.2228	0.7031	0.2088	0.036*
H8B	0.2741	0.5587	0.1573	0.036*
C9	0.30743 (16)	0.7010 (5)	0.3164 (3)	0.0304 (8)
H9A	0.3337	0.7968	0.2751	0.036*
H9B	0.2883	0.7882	0.3737	0.036*
C10	0.38229 (17)	0.3950 (6)	0.2964 (3)	0.0351 (9)
H10A	0.3534	0.3487	0.2283	0.042*
H10B	0.3994	0.2640	0.3371	0.042*
C11	0.43528 (19)	0.5240 (7)	0.2543 (3)	0.0494 (12)
H11A	0.4573	0.4323	0.2031	0.059*
H11B	0.4181	0.6492	0.2084	0.059*
C12	0.44707 (19)	0.7346 (7)	0.4274 (4)	0.0459 (11)
H12A	0.4307	0.8634	0.3837	0.055*
H12B	0.4770	0.7837	0.4934	0.055*
C13	0.39376 (17)	0.6159 (6)	0.4741 (3)	0.0362 (9)
H13A	0.4109	0.4971	0.5252	0.043*
H13B	0.3725	0.7166	0.5219	0.043*

	U11	U22	U33	U12	U13	U23
V1	0.0394 (4)	0.0279 (4)	0.0198 (3)	−0.0050 (3)	0.0006 (3)	0.0003 (3)
Br1	0.0583 (3)	0.0709 (4)	0.0544 (3)	−0.0337 (3)	0.0067 (2)	−0.0207 (2)
N1	0.0354 (17)	0.0205 (16)	0.0202 (15)	−0.0021 (13)	0.0015 (13)	0.0013 (12)
N2	0.0338 (17)	0.0198 (16)	0.0215 (14)	−0.0002 (13)	0.0006 (12)	−0.0009 (12)
O1	0.0541 (18)	0.0570 (19)	0.0305 (15)	−0.0253 (15)	−0.0059 (13)	0.0126 (14)
O2	0.0331 (16)	0.068 (2)	0.0572 (18)	−0.0001 (15)	0.0048 (14)	0.0167 (17)
O3	0.0503 (17)	0.0344 (16)	0.0459 (16)	0.0026 (13)	−0.0017 (13)	0.0139 (13)
O4	0.0660 (19)	0.0461 (18)	0.0318 (14)	−0.0093 (15)	0.0135 (13)	−0.0113 (13)
C1	0.034 (2)	0.025 (2)	0.029 (2)	−0.0045 (16)	0.0059 (16)	−0.0027 (16)
C2	0.033 (2)	0.034 (2)	0.033 (2)	−0.0049 (18)	0.0085 (17)	−0.0014 (17)
C3	0.045 (2)	0.045 (3)	0.033 (2)	−0.011 (2)	0.0064 (18)	0.0057 (19)
C4	0.048 (3)	0.033 (2)	0.051 (3)	−0.0123 (19)	0.018 (2)	−0.003 (2)
C5	0.037 (2)	0.045 (3)	0.039 (2)	−0.0175 (19)	0.0094 (18)	−0.019 (2)
C6	0.039 (2)	0.041 (3)	0.031 (2)	−0.0065 (19)	0.0039 (17)	−0.0050 (18)
C7	0.037 (2)	0.037 (2)	0.0181 (17)	0.0017 (18)	0.0026 (15)	−0.0014 (17)
C8	0.037 (2)	0.024 (2)	0.0287 (19)	0.0028 (16)	0.0010 (16)	0.0062 (16)
C9	0.033 (2)	0.022 (2)	0.035 (2)	0.0019 (16)	0.0016 (16)	−0.0003 (17)
C10	0.045 (2)	0.030 (2)	0.030 (2)	0.0120 (18)	0.0030 (17)	0.0002 (17)
C11	0.047 (3)	0.065 (3)	0.039 (2)	0.011 (2)	0.017 (2)	0.010 (2)
C12	0.041 (2)	0.043 (3)	0.051 (3)	−0.008 (2)	−0.008 (2)	0.007 (2)
C13	0.041 (2)	0.038 (2)	0.027 (2)	−0.0040 (19)	−0.0072 (17)	−0.0010 (17)

V1—O4	1.611 (2)	C4—C5	1.392 (5)
V1—O3	1.622 (3)	C4—H4	0.9300
V1—O1	1.907 (3)	C5—C6	1.365 (5)
V1—N1	2.142 (3)	C6—H6	0.9300
V1—N2	2.159 (3)	C7—H7	0.9300
Br1—C5	1.899 (4)	C8—C9	1.504 (5)
N1—C7	1.275 (4)	C8—H8A	0.9700
N1—C8	1.483 (4)	C8—H8B	0.9700
N2—C9	1.487 (4)	C9—H9A	0.9700
N2—C13	1.497 (4)	C9—H9B	0.9700
N2—C10	1.497 (4)	C10—C11	1.505 (5)
O1—C2	1.314 (4)	C10—H10A	0.9700
O2—C12	1.423 (5)	C10—H10B	0.9700
O2—C11	1.428 (4)	C11—H11A	0.9700
C1—C2	1.406 (5)	C11—H11B	0.9700
C1—C6	1.410 (5)	C12—C13	1.502 (5)
C1—C7	1.433 (5)	C12—H12A	0.9700
C2—C3	1.392 (5)	C12—H12B	0.9700
C3—C4	1.368 (5)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
O4—V1—O3	109.41 (14)	N1—C7—C1	126.0 (3)
O4—V1—O1	102.89 (13)	N1—C7—H7	117.0
O3—V1—O1	98.38 (13)	C1—C7—H7	117.0
O4—V1—N1	116.30 (13)	N1—C8—C9	107.9 (3)
O3—V1—N1	132.70 (12)	N1—C8—H8A	110.1
O1—V1—N1	83.17 (11)	C9—C8—H8A	110.1
O4—V1—N2	94.75 (12)	N1—C8—H8B	110.1
O3—V1—N2	89.77 (12)	C9—C8—H8B	110.1
O1—V1—N2	156.74 (10)	H8A—C8—H8B	108.4
N1—V1—N2	75.39 (10)	N2—C9—C8	109.1 (3)
C7—N1—C8	116.0 (3)	N2—C9—H9A	109.9
C7—N1—V1	127.9 (2)	C8—C9—H9A	109.9
C8—N1—V1	116.1 (2)	N2—C9—H9B	109.9
C9—N2—C13	111.1 (3)	C8—C9—H9B	109.9
C9—N2—C10	112.7 (3)	H9A—C9—H9B	108.3
C13—N2—C10	107.5 (3)	N2—C10—C11	112.7 (3)
C9—N2—V1	105.7 (2)	N2—C10—H10A	109.0
C13—N2—V1	109.74 (19)	C11—C10—H10A	109.0
C10—N2—V1	110.0 (2)	N2—C10—H10B	109.0
C2—O1—V1	136.7 (2)	C11—C10—H10B	109.0
C12—O2—C11	110.0 (3)	H10A—C10—H10B	107.8
C2—C1—C6	119.5 (3)	O2—C11—C10	111.1 (3)
C2—C1—C7	121.5 (3)	O2—C11—H11A	109.4
C6—C1—C7	119.0 (3)	C10—C11—H11A	109.4
O1—C2—C3	119.3 (3)	O2—C11—H11B	109.4
O1—C2—C1	121.8 (3)	C10—C11—H11B	109.4
C3—C2—C1	118.9 (3)	H11A—C11—H11B	108.0
C4—C3—C2	121.1 (4)	O2—C12—C13	111.9 (3)
C4—C3—H3	119.4	O2—C12—H12A	109.2
C2—C3—H3	119.4	C13—C12—H12A	109.2
C3—C4—C5	119.8 (4)	O2—C12—H12B	109.2
C3—C4—H4	120.1	C13—C12—H12B	109.2
C5—C4—H4	120.1	H12A—C12—H12B	107.9
C6—C5—C4	120.9 (4)	N2—C13—C12	113.1 (3)
C6—C5—Br1	120.1 (3)	N2—C13—H13A	109.0
C4—C5—Br1	119.0 (3)	C12—C13—H13A	109.0
C5—C6—C1	119.7 (4)	N2—C13—H13B	109.0
C5—C6—H6	120.1	C12—C13—H13B	109.0
C1—C6—H6	120.1	H13A—C13—H13B	107.8

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.53	3.241 (4)	133
C11—H11A···O2ii	0.97	2.57	3.479 (5)	156

Table 1

Selected bond lengths (Å)

V1—O4	1.611 (2)
V1—O3	1.622 (3)
V1—O1	1.907 (3)
V1—N1	2.142 (3)
V1—N2	2.159 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.53	3.241 (4)	133
C11—H11A⋯O2ii	0.97	2.57	3.479 (5)	156

Symmetry codes: (i) ; (ii) .