{2-[(2-Amino-cyclo-hex-yl)imino-meth-yl]phenolato}dioxidovanadium(V).

In the title dioxidovanadium complex, [V(C(13)H(17)N(2)O)O(2)], the V(V) atom is in a square-based pyramidal coordination: the basal plane is defined by the phenolate O, imine N and amine N atoms of the tridentate Schiff base ligand, and by one oxide O atom. The apical position is occupied by the other oxide O atom. In the crystal, mol-ecules are connected by N-H⋯O and N-H⋯(O,O) hydrogen bonds, forming a tetra-mer.

Related literature

For related structures and their proporties, see: Agarwal & Prasad (2006 ▶); Chohan & Sumrra (2010 ▶); Huo et al. (2004 ▶); Jing et al. (2005 ▶); Lodyga-Chruscinska et al. (2008 ▶); Xie et al. (2004 ▶); Yuan et al. (2009 ▶).

Experimental

Crystal data

[V(C13H17N2O)O2]

M = 300.23

Tetragonal,

a = 19.120 (9) Å

c = 15.421 (3) Å

V = 5638 (4) Å3

Z = 16

Mo Kα radiation

μ = 0.71 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.854, T max = 0.871

19404 measured reflections

2537 independent reflections

1487 reflections with I > 2σ(I)

R int = 0.172

Refinement

R[F 2 > 2σ(F 2)] = 0.099

wR(F 2) = 0.203

S = 1.08

2537 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011592/hb6676sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011592/hb6676Isup2.hkl

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

[V(C13H17N2O)O2]	Dx = 1.415 Mg m−3
Mr = 300.23	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 1125 reflections
a = 19.120 (9) Å	θ = 2.7–24.5°
c = 15.421 (3) Å	µ = 0.71 mm−1
V = 5638 (4) Å3	T = 298 K
Z = 16	Block, yellow
F(000) = 2496	0.23 × 0.20 × 0.20 mm

Bruker SMART 1000 CCD diffractometer	2537 independent reflections
Radiation source: fine-focus sealed tube	1487 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.172
ω scan	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −23→23
Tmin = 0.854, Tmax = 0.871	k = −23→23
19404 measured reflections	l = −18→18

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)] = 0.099	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0708P)2 + 16.0234P] where P = (Fo2 + 2Fc2)/3
2537 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.30 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	0.04762 (6)	0.08630 (6)	0.66104 (7)	0.0417 (4)
N1	0.1074 (3)	0.0188 (3)	0.5792 (4)	0.0574 (17)
N2	0.0524 (3)	0.1379 (3)	0.5413 (3)	0.0424 (14)
H2A	0.0122	0.1616	0.5337	0.051*
H2B	0.0872	0.1695	0.5436	0.051*
O1	0.0854 (3)	0.0299 (3)	0.7510 (3)	0.0589 (14)
O2	−0.0330 (2)	0.0631 (2)	0.6543 (3)	0.0581 (14)
O3	0.0526 (3)	0.1602 (2)	0.7122 (3)	0.0596 (14)
C1	0.1142 (4)	−0.0770 (4)	0.6803 (5)	0.062 (2)
C2	0.0962 (4)	−0.0379 (4)	0.7536 (5)	0.057 (2)
C3	0.0907 (5)	−0.0727 (5)	0.8315 (6)	0.078 (3)
H3	0.0788	−0.0477	0.8811	0.093*
C4	0.1022 (6)	−0.1422 (6)	0.8374 (7)	0.109 (4)
H4	0.0984	−0.1643	0.8909	0.130*
C5	0.1195 (6)	−0.1808 (5)	0.7646 (8)	0.111 (4)
H5	0.1271	−0.2287	0.7692	0.133*
C6	0.1251 (5)	−0.1488 (5)	0.6875 (7)	0.094 (3)
H6	0.1365	−0.1748	0.6384	0.112*
C7	0.1238 (4)	−0.0435 (5)	0.5984 (5)	0.073 (3)
H7	0.1441	−0.0701	0.5546	0.087*
C8	0.1201 (5)	0.0398 (6)	0.4903 (6)	0.094 (3)
H8	0.1107	−0.0015	0.4546	0.112*
C9	0.0635 (4)	0.0936 (4)	0.4666 (5)	0.063 (2)
H9	0.0202	0.0670	0.4586	0.075*
C10	0.0774 (7)	0.1306 (6)	0.3813 (6)	0.110 (4)
H10A	0.0630	0.0998	0.3346	0.132*
H10B	0.0478	0.1717	0.3788	0.132*
C11	0.1431 (8)	0.1505 (8)	0.3664 (10)	0.167 (7)
H11A	0.1534	0.1903	0.4032	0.200*
H11B	0.1465	0.1661	0.3067	0.200*
C12	0.1999 (6)	0.0933 (7)	0.3823 (7)	0.115 (4)
H12A	0.1972	0.0579	0.3373	0.137*
H12B	0.2461	0.1141	0.3804	0.137*
C13	0.1873 (5)	0.0597 (7)	0.4717 (8)	0.134 (5)
H13A	0.2170	0.0187	0.4764	0.161*
H13B	0.2023	0.0926	0.5158	0.161*

	U11	U22	U33	U12	U13	U23
V1	0.0364 (7)	0.0422 (8)	0.0467 (7)	0.0001 (6)	0.0060 (6)	−0.0070 (6)
N1	0.056 (4)	0.066 (4)	0.050 (4)	0.032 (3)	0.012 (3)	0.003 (3)
N2	0.033 (3)	0.039 (3)	0.055 (4)	−0.001 (3)	0.000 (3)	0.006 (3)
O1	0.072 (4)	0.055 (3)	0.049 (3)	0.009 (3)	−0.008 (3)	−0.004 (3)
O2	0.054 (3)	0.049 (3)	0.071 (4)	−0.002 (2)	0.009 (3)	−0.005 (3)
O3	0.082 (4)	0.047 (3)	0.050 (3)	−0.010 (3)	0.008 (3)	−0.007 (2)
C1	0.076 (6)	0.061 (5)	0.048 (5)	0.010 (4)	0.013 (4)	−0.001 (4)
C2	0.057 (5)	0.064 (6)	0.050 (5)	0.002 (4)	−0.003 (4)	0.005 (4)
C3	0.105 (7)	0.073 (6)	0.055 (6)	0.018 (5)	0.010 (5)	0.002 (5)
C4	0.160 (11)	0.085 (8)	0.080 (7)	0.024 (7)	0.023 (7)	0.025 (7)
C5	0.167 (11)	0.051 (6)	0.115 (10)	0.037 (6)	0.030 (8)	0.003 (6)
C6	0.150 (10)	0.055 (6)	0.076 (7)	0.040 (6)	0.022 (6)	0.015 (5)
C7	0.073 (6)	0.097 (7)	0.048 (5)	0.044 (5)	0.005 (4)	−0.012 (5)
C8	0.095 (8)	0.124 (8)	0.062 (6)	0.045 (6)	0.034 (5)	0.014 (6)
C9	0.083 (6)	0.063 (5)	0.043 (4)	0.028 (5)	0.003 (4)	0.002 (4)
C10	0.161 (12)	0.115 (9)	0.054 (6)	0.037 (8)	0.029 (7)	0.036 (6)
C11	0.142 (13)	0.200 (16)	0.158 (13)	−0.015 (12)	0.024 (10)	0.123 (12)
C12	0.111 (9)	0.135 (10)	0.098 (8)	−0.012 (8)	0.034 (7)	0.026 (7)
C13	0.058 (7)	0.215 (14)	0.129 (10)	0.002 (7)	−0.005 (7)	0.079 (10)

V1—O2	1.607 (5)	C5—H5	0.9300
V1—O3	1.621 (5)	C6—H6	0.9300
V1—O1	1.900 (5)	C7—H7	0.9300
V1—N2	2.095 (5)	C8—C13	1.370 (12)
V1—N1	2.137 (6)	C8—C9	1.536 (11)
N1—C7	1.267 (9)	C8—H8	0.9800
N1—C8	1.448 (10)	C9—C10	1.517 (11)
N2—C9	1.447 (8)	C9—H9	0.9800
N2—H2A	0.9000	C10—C11	1.332 (15)
N2—H2B	0.9000	C10—H10A	0.9700
O1—C2	1.314 (8)	C10—H10B	0.9700
C1—C6	1.394 (11)	C11—C12	1.561 (17)
C1—C2	1.398 (10)	C11—H11A	0.9700
C1—C7	1.428 (11)	C11—H11B	0.9700
C2—C3	1.377 (11)	C12—C13	1.541 (13)
C3—C4	1.350 (12)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.383 (13)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.342 (13)
O2—V1—O3	109.2 (3)	N1—C7—H7	116.7
O2—V1—O1	104.8 (2)	C1—C7—H7	116.7
O3—V1—O1	96.7 (2)	C13—C8—N1	115.6 (9)
O2—V1—N2	96.6 (2)	C13—C8—C9	115.2 (9)
O3—V1—N2	90.9 (2)	N1—C8—C9	107.0 (6)
O1—V1—N2	153.4 (2)	C13—C8—H8	106.1
O2—V1—N1	108.0 (2)	N1—C8—H8	106.1
O3—V1—N1	141.5 (3)	C9—C8—H8	106.1
O1—V1—N1	83.4 (2)	N2—C9—C10	116.3 (7)
N2—V1—N1	75.0 (2)	N2—C9—C8	107.8 (6)
C7—N1—C8	116.1 (7)	C10—C9—C8	113.3 (7)
C7—N1—V1	124.2 (5)	N2—C9—H9	106.2
C8—N1—V1	118.8 (5)	C10—C9—H9	106.2
C9—N2—V1	115.6 (4)	C8—C9—H9	106.2
C9—N2—H2A	108.4	C11—C10—C9	116.6 (11)
V1—N2—H2A	108.4	C11—C10—H10A	108.1
C9—N2—H2B	108.4	C9—C10—H10A	108.1
V1—N2—H2B	108.4	C11—C10—H10B	108.1
H2A—N2—H2B	107.4	C9—C10—H10B	108.1
C2—O1—V1	129.9 (5)	H10A—C10—H10B	107.3
C6—C1—C2	119.9 (8)	C10—C11—C12	115.4 (11)
C6—C1—C7	119.5 (8)	C10—C11—H11A	108.4
C2—C1—C7	120.5 (7)	C12—C11—H11A	108.4
O1—C2—C3	119.4 (7)	C10—C11—H11B	108.4
O1—C2—C1	122.8 (7)	C12—C11—H11B	108.4
C3—C2—C1	117.9 (8)	H11A—C11—H11B	107.5
C4—C3—C2	121.4 (9)	C13—C12—C11	108.9 (10)
C4—C3—H3	119.3	C13—C12—H12A	109.9
C2—C3—H3	119.3	C11—C12—H12A	109.9
C3—C4—C5	120.7 (10)	C13—C12—H12B	109.9
C3—C4—H4	119.7	C11—C12—H12B	109.9
C5—C4—H4	119.7	H12A—C12—H12B	108.3
C6—C5—C4	119.7 (9)	C8—C13—C12	116.7 (9)
C6—C5—H5	120.1	C8—C13—H13A	108.1
C4—C5—H5	120.1	C12—C13—H13A	108.1
C5—C6—C1	120.4 (9)	C8—C13—H13B	108.1
C5—C6—H6	119.8	C12—C13—H13B	108.1
C1—C6—H6	119.8	H13A—C13—H13B	107.3
N1—C7—C1	126.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2i	0.90	2.26	3.099 (7)	155
N2—H2B···O3i	0.90	2.55	3.229 (7)	133
N2—H2A···O3ii	0.90	2.07	2.948 (7)	166

Table 1

Selected bond lengths (Å)

V1—O2	1.607 (5)
V1—O3	1.621 (5)
V1—O1	1.900 (5)
V1—N2	2.095 (5)
V1—N1	2.137 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2i	0.90	2.26	3.099 (7)	155
N2—H2B⋯O3i	0.90	2.55	3.229 (7)	133
N2—H2A⋯O3ii	0.90	2.07	2.948 (7)	166

Symmetry codes: (i) ; (ii) .