{2-[1-(2-Amino-2-methyl-propyl-imino)eth-yl]phenolato-κN,N',O}dioxidovanadium(V).

In the crystal structure of the title compound, [V(C(12)H(17)N(2)O)O(2)], the vanadium(V) centre is five-coordinate in a distorted square-pyramidal environment. The three atoms of the deprotonated Schiff base and a double-bonded O atom comprise the basal plane. N-H⋯O hydrogen bonds lead to a zigzag chain structure parallel to [001].

Related literature

For general background, see: Carter-Franklin et al. (2003 ▶); Eady (2003 ▶); Evangelou (2002 ▶); Mendz (1991 ▶); Mokry & Carrano (1993 ▶); Parekh et al. (2006 ▶); Rehder et al. (2002 ▶, 2003 ▶); Shahzadi et al. (2007 ▶). For related structures, see: Kwiatkowski et al. (2003 ▶, 2007 ▶); Rao et al. (1981 ▶). For synthesis, see: Kwiatkowski et al. (2003 ▶). For the calculation of square-pyramidal geometries, see: Holmes (1984 ▶).

Experimental

Crystal data

[V(C12H17N2O)O2]

M = 288.22

Orthorhombic,

a = 11.1198 (6) Å

b = 15.7408 (8) Å

c = 7.6448 (3) Å

V = 1338.10 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.74 mm−1

T = 295 (2) K

0.20 × 0.04 × 0.04 mm

Data collection

Oxford Diffraction Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.941, T max = 0.964

11574 measured reflections

2126 independent reflections

1387 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.051

S = 0.83

2126 reflections

167 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 849 Friedel pairs

Flack parameter: 0.23 (2)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042839/ng2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042839/ng2526Isup2.hkl

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

[V(C12H17N2O)O2]	F(000) = 600
Mr = 288.22	Dx = 1.431 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2126 reflections
a = 11.1198 (6) Å	θ = 3.2–25.1°
b = 15.7408 (8) Å	µ = 0.74 mm−1
c = 7.6448 (3) Å	T = 295 K
V = 1338.10 (11) Å3	Needle, white
Z = 4	0.2 × 0.04 × 0.04 mm

Oxford Diffraction Ruby CCD diffractometer	2126 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1387 reflections with I > 2σ(I)
graphite	Rint = 0.071
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.2°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −18→18
Tmin = 0.941, Tmax = 0.964	l = −9→7
11574 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.051	w = 1/[σ2(Fo2) + (0.0211P)2] where P = (Fo2 + 2Fc2)/3
S = 0.83	(Δ/σ)max < 0.001
2126 reflections	Δρmax = 0.19 e Å−3
167 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 849 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.23 (2)

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
C1	0.3317 (3)	0.3973 (2)	0.5333 (4)	0.0380 (8)
C2	0.2695 (3)	0.37563 (19)	0.6865 (4)	0.0354 (8)
C3	0.3314 (3)	0.37812 (17)	0.8474 (6)	0.0512 (8)
H3A	0.2903	0.3651	0.9499	0.061*
C4	0.4498 (3)	0.3992 (2)	0.8561 (6)	0.0560 (10)
H4A	0.4887	0.4012	0.9637	0.067*
C5	0.5121 (3)	0.4175 (2)	0.7045 (6)	0.0602 (11)
H5A	0.5931	0.4319	0.7101	0.072*
C6	0.4544 (3)	0.4145 (2)	0.5448 (5)	0.0510 (10)
H6A	0.4982	0.4240	0.4431	0.061*
C7	0.1437 (3)	0.34815 (19)	0.6801 (4)	0.0399 (8)
N8	0.0753 (2)	0.36544 (15)	0.5463 (3)	0.0378 (7)
C9	−0.0510 (3)	0.3371 (2)	0.5463 (4)	0.0422 (9)
H9A	−0.0956	0.3677	0.6353	0.051*
H9B	−0.0549	0.2770	0.5733	0.051*
C10	−0.1063 (3)	0.3534 (2)	0.3683 (4)	0.0407 (9)
N11	−0.06106 (19)	0.44045 (15)	0.3205 (5)	0.0408 (6)
H11A	−0.0946	0.4790	0.3925	0.049*
H11B	−0.0844	0.4528	0.2107	0.049*
V12	0.12859 (4)	0.45059 (3)	0.33674 (6)	0.03758 (15)
O13	0.27910 (18)	0.39910 (13)	0.3758 (3)	0.0456 (6)
O14	0.1359 (2)	0.45725 (14)	0.1236 (2)	0.0467 (6)
O15	0.1372 (2)	0.54432 (13)	0.4218 (2)	0.0483 (6)
C26	0.0950 (3)	0.29854 (18)	0.8337 (6)	0.0592 (9)
H26A	0.0162	0.2776	0.8060	0.089*
H26B	0.0905	0.3349	0.9343	0.089*
H26C	0.1474	0.2516	0.8584	0.089*
C27	−0.0620 (3)	0.2904 (2)	0.2305 (5)	0.0536 (9)
H27A	0.0243	0.2886	0.2320	0.080*
H27B	−0.0890	0.3081	0.1170	0.080*
H27C	−0.0933	0.2349	0.2559	0.080*
C28	−0.2434 (3)	0.3536 (2)	0.3770 (5)	0.0699 (12)
H28A	−0.2697	0.3960	0.4587	0.105*
H28B	−0.2713	0.2988	0.4143	0.105*
H28C	−0.2756	0.3661	0.2633	0.105*

	U11	U22	U33	U12	U13	U23
C1	0.039 (2)	0.0260 (19)	0.049 (2)	0.0093 (17)	0.0054 (19)	0.0025 (17)
C2	0.041 (2)	0.0303 (19)	0.035 (2)	0.0077 (17)	0.0034 (17)	−0.0038 (16)
C3	0.064 (2)	0.0462 (19)	0.043 (2)	0.0081 (17)	0.007 (3)	0.005 (3)
C4	0.058 (3)	0.056 (2)	0.054 (3)	0.0082 (19)	−0.009 (3)	−0.016 (3)
C5	0.039 (2)	0.053 (3)	0.089 (3)	−0.0058 (19)	−0.002 (3)	−0.005 (2)
C6	0.050 (3)	0.051 (2)	0.052 (2)	0.001 (2)	0.009 (2)	0.003 (2)
C7	0.056 (2)	0.0311 (19)	0.033 (2)	0.0004 (19)	0.0127 (18)	−0.0038 (14)
N8	0.0384 (19)	0.0394 (17)	0.0355 (16)	0.0009 (14)	0.0112 (14)	−0.0026 (14)
C9	0.053 (3)	0.039 (2)	0.0346 (19)	−0.0049 (19)	0.0174 (18)	−0.0038 (17)
C10	0.038 (2)	0.0445 (19)	0.040 (2)	−0.0079 (17)	0.0074 (17)	−0.0095 (18)
N11	0.0423 (14)	0.0400 (14)	0.0400 (13)	0.0048 (13)	−0.0037 (18)	−0.0058 (18)
V12	0.0404 (3)	0.0357 (3)	0.0366 (3)	0.0011 (3)	0.0062 (4)	0.0047 (4)
O13	0.0417 (13)	0.0517 (14)	0.0434 (17)	0.0064 (10)	0.0104 (11)	0.0074 (12)
O14	0.0508 (14)	0.0579 (14)	0.0315 (11)	0.0065 (16)	0.0078 (11)	0.0070 (11)
O15	0.0559 (16)	0.0353 (13)	0.0538 (12)	−0.0029 (13)	0.0005 (11)	−0.0044 (11)
C26	0.082 (3)	0.0554 (19)	0.0399 (16)	−0.0127 (18)	0.015 (3)	0.005 (3)
C27	0.067 (2)	0.047 (2)	0.0469 (18)	−0.008 (2)	0.013 (2)	−0.007 (2)
C28	0.046 (2)	0.085 (3)	0.078 (3)	−0.017 (2)	0.004 (2)	−0.004 (3)

C1—O13	1.339 (4)	C10—N11	1.504 (4)
C1—C6	1.393 (5)	C10—C28	1.527 (4)
C1—C2	1.402 (4)	C10—C27	1.529 (4)
C2—C3	1.410 (5)	N11—V12	2.118 (2)
C2—C7	1.465 (4)	N11—H11A	0.9000
C3—C4	1.359 (4)	N11—H11B	0.9000
C3—H3A	0.9300	V12—O15	1.6151 (19)
C4—C5	1.380 (5)	V12—O14	1.6352 (18)
C4—H4A	0.9300	V12—O13	1.883 (2)
C5—C6	1.380 (4)	C26—H26A	0.9600
C5—H5A	0.9300	C26—H26B	0.9600
C6—H6A	0.9300	C26—H26C	0.9600
C7—N8	1.304 (4)	C27—H27A	0.9600
C7—C26	1.510 (4)	C27—H27B	0.9600
N8—C9	1.473 (4)	C27—H27C	0.9600
N8—V12	2.171 (3)	C28—H28A	0.9600
C9—C10	1.515 (4)	C28—H28B	0.9600
C9—H9A	0.9700	C28—H28C	0.9600
C9—H9B	0.9700
O13—C1—C6	118.7 (3)	C10—N11—V12	112.76 (17)
O13—C1—C2	122.7 (3)	C10—N11—H11A	109.0
C6—C1—C2	118.5 (3)	V12—N11—H11A	109.0
C1—C2—C3	118.7 (3)	C10—N11—H11B	109.0
C1—C2—C7	121.0 (3)	V12—N11—H11B	109.0
C3—C2—C7	120.2 (3)	H11A—N11—H11B	107.8
C4—C3—C2	121.5 (4)	O15—V12—O14	109.85 (10)
C4—C3—H3A	119.2	O15—V12—O13	106.06 (11)
C2—C3—H3A	119.2	O14—V12—O13	98.12 (10)
C3—C4—C5	119.7 (4)	O15—V12—N11	98.71 (11)
C3—C4—H4A	120.1	O14—V12—N11	89.77 (13)
C5—C4—H4A	120.1	O13—V12—N11	149.49 (10)
C6—C5—C4	120.1 (4)	O15—V12—N8	106.46 (9)
C6—C5—H5A	119.9	O14—V12—N8	142.05 (11)
C4—C5—H5A	119.9	O13—V12—N8	81.94 (9)
C5—C6—C1	121.2 (3)	N11—V12—N8	74.05 (12)
C5—C6—H6A	119.4	C1—O13—V12	122.65 (18)
C1—C6—H6A	119.4	C7—C26—H26A	109.5
N8—C7—C2	121.4 (3)	C7—C26—H26B	109.5
N8—C7—C26	120.6 (3)	H26A—C26—H26B	109.5
C2—C7—C26	118.0 (3)	C7—C26—H26C	109.5
C7—N8—C9	119.5 (3)	H26A—C26—H26C	109.5
C7—N8—V12	123.3 (2)	H26B—C26—H26C	109.5
C9—N8—V12	116.56 (19)	C10—C27—H27A	109.5
N8—C9—C10	109.6 (2)	C10—C27—H27B	109.5
N8—C9—H9A	109.8	H27A—C27—H27B	109.5
C10—C9—H9A	109.8	C10—C27—H27C	109.5
N8—C9—H9B	109.8	H27A—C27—H27C	109.5
C10—C9—H9B	109.8	H27B—C27—H27C	109.5
H9A—C9—H9B	108.2	C10—C28—H28A	109.5
N11—C10—C9	103.7 (3)	C10—C28—H28B	109.5
N11—C10—C28	110.0 (2)	H28A—C28—H28B	109.5
C9—C10—C28	111.5 (3)	C10—C28—H28C	109.5
N11—C10—C27	108.4 (3)	H28A—C28—H28C	109.5
C9—C10—C27	112.2 (3)	H28B—C28—H28C	109.5
C28—C10—C27	110.7 (3)
O13—C1—C2—C3	−178.0 (3)	N8—C9—C10—C27	74.2 (3)
C6—C1—C2—C3	4.6 (4)	C9—C10—N11—V12	53.3 (3)
O13—C1—C2—C7	4.0 (4)	C28—C10—N11—V12	172.7 (2)
C6—C1—C2—C7	−173.4 (3)	C27—C10—N11—V12	−66.2 (3)
C1—C2—C3—C4	−1.5 (4)	C10—N11—V12—O15	−139.7 (2)
C7—C2—C3—C4	176.6 (3)	C10—N11—V12—O14	110.2 (3)
C2—C3—C4—C5	−0.9 (5)	C10—N11—V12—O13	4.5 (4)
C3—C4—C5—C6	0.0 (5)	C10—N11—V12—N8	−35.0 (2)
C4—C5—C6—C1	3.4 (6)	C7—N8—V12—O15	−66.8 (3)
O13—C1—C6—C5	176.9 (3)	C9—N8—V12—O15	103.9 (2)
C2—C1—C6—C5	−5.6 (5)	C7—N8—V12—O14	130.5 (2)
C1—C2—C7—N8	−20.0 (4)	C9—N8—V12—O14	−58.7 (3)
C3—C2—C7—N8	162.0 (3)	C7—N8—V12—O13	37.6 (2)
C1—C2—C7—C26	159.8 (3)	C9—N8—V12—O13	−151.6 (2)
C3—C2—C7—C26	−18.2 (4)	C7—N8—V12—N11	−161.4 (3)
C2—C7—N8—C9	−179.5 (3)	C9—N8—V12—N11	9.3 (2)
C26—C7—N8—C9	0.8 (4)	C6—C1—O13—V12	−136.7 (2)
C2—C7—N8—V12	−9.0 (4)	C2—C1—O13—V12	45.9 (4)
C26—C7—N8—V12	171.2 (2)	O15—V12—O13—C1	50.2 (2)
C7—N8—C9—C10	−172.0 (3)	O14—V12—O13—C1	163.6 (2)
V12—N8—C9—C10	16.9 (3)	N11—V12—O13—C1	−92.8 (3)
N8—C9—C10—N11	−42.6 (3)	N8—V12—O13—C1	−54.7 (2)
N8—C9—C10—C28	−161.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11A···O14i	0.90	2.08	2.942 (4)	159
N11—H11B···O15ii	0.90	2.29	3.173 (4)	168
C26—H26B···O14iii	0.96	2.46	3.370 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11A⋯O14i	0.90	2.08	2.942 (4)	159
N11—H11B⋯O15ii	0.90	2.29	3.173 (4)	168

Symmetry codes: (i) ; (ii) .