(Methoxo-κO)oxidobis(quinolin-8-olato-κ2N,O)vanadium(V)

Guo, Z.; Li, L.; Wang, C.; Xu, T.; Li, J.

doi:10.1107/S1600536809031560

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1075

doi:10.1107/S1600536809031560

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(Methoxo-κO)oxidobis(quinolin-8-olato-κ²N,O)vanadium(V)

Zhenghua Guo,^a Lianzhi Li,^a ^* Chengyuan Wang,^b Tao Xu ^a and Jinghong Li ^a

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and ^bResearch Center of Medical Chemistry & Chemical Biology, Chongqing Technology and Business University, Chongqing 400067, People's Republic of China
^*Correspondence e-mail: lilianzhi1963@yahoo.com.cn

(Received 20 July 2009; accepted 11 August 2009; online 15 August 2009)

In the title complex, [V(C₉H₆NO)₂(CH₃O)O], the central V^V atom is coordinated by the O atoms from the oxido and methoxo ligands and the N and O atoms of two bis-chelating quinolin-8-olate ligands, forming a distorted octahedral environment. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds connect molecules into centrosymmetric dimers which are, in turn, linked by weak C—H⋯π interactions into chains along the b axis.

Related literature

For the properties of vanadium compounds, see: Crans et al. (2004 ); Diego et al. (2003 ); Thompson & Orvig (2006 ). For the structures of oxidovandium complexes see: Hoshina et al. (1998 ); Otieno et al. (1996 ).

Experimental

Crystal data

[V(C₉H₆NO)₂(CH₃O)O]
M_r = 386.27
Monoclinic, P 2₁ /c
a = 14.0405 (16) Å
b = 8.0019 (1) Å
c = 15.5920 (18) Å
β = 110.560 (1)°
V = 1640.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 298 K
0.44 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.768, T_max = 0.900
7660 measured reflections
2893 independent reflections
1378 reflections with I > 2σ(I)
R_int = 0.102

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.230
S = 1.00
2893 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected bond angles (°)

O3—V1—O2	101.9 (2)
O3—V1—O1	91.4 (2)
O2—V1—O1	156.3 (2)
O3—V1—N1	164.3 (2)
O2—V1—N1	85.35 (19)
O1—V1—N1	77.40 (19)
O4—V1—N2	170.1 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O4ⁱ	0.93	2.54	3.355 (8)	146
C19—H19B⋯Cgⁱⁱ	0.96	2.84	3.520 (9)	128
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z. Cg is the centroid of the N2/C10–C14 ring.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031560/lh2870sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031560/lh2870Isup2.hkl

checkCIF report

Comment top

Vanadium is a biologically essential trace element, encountered in metalloenzymes such as haloperoxidases or nitrogenases. Its coordination chemistry has received increasing attention due to the fact that vanadium compounds in various oxidation states have insulin-mimetic properties (Diego et al., 2003; Crans et al., 2004; Thompson & Orvig, 2006). We report here the synthesis and crystal structure of the title complex.

In the molecular structure (Fig.1.), the central V^V atom is six-coordinated by the O atoms of the oxo and methoxo ligands and the N atoms and O atoms of two 8-hydroxyquinolato ligands, forming a distorted octahedral environment (Table 1). The V=O bond distance is 1.602 (4) Å which is typical for oxovandium complexes (Hoshina et al., 1998; Otieno et al., 1996). The mean planes of the chelated rings defined by N1/C5—C6/O1/V1 and N2/C14—C15/O2/V1 form a dihedral angle of 82.02 (18)°.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds connect molecules into centrosymmetric dimers (Fig. 2) which are, in turn, linked by weak C—H···π interactions into chains along the b axis.

Related literature top

For the properties of vanadium compounds, see: Crans et al. (2004); Diego et al. (2003); Thompson & Orvig (2006). For the structures of oxovandium complexes see: Hoshina et al. (1998); Otieno et al. (1996). Cg is the centroid of the N2/C10–C14 ring.

Experimental top

8-Hydroxyquinoline (1 mmol, 145.16 mg) was dissolved in hot methanol (10 ml) and added dropwise to a methanol solution (3 ml) of VOSO₄.3H₂O (1 mmol, 225.4 mg). The mixture was then stirred at 323 K for 4 h. The solution was held at room temperature for 15 days, whereupon brown needle crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

(Methoxo-κO)oxidobis(quinolin-8-olato-κ²N,O)vanadium(V) top

Crystal data top

[V(C₉H₆NO)₂(CH₃O)O]	F(000) = 792
M_r = 386.27	D_x = 1.564 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1311 reflections
a = 14.0405 (16) Å	θ = 2.7–25.3°
b = 8.0019 (1) Å	µ = 0.63 mm⁻¹
c = 15.5920 (18) Å	T = 298 K
β = 110.560 (1)°	Needle, brown
V = 1640.2 (3) Å³	0.44 × 0.18 × 0.17 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2893 independent reflections
Radiation source: fine-focus sealed tube	1378 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.102
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.768, T_max = 0.900	k = −9→6
7660 measured reflections	l = −18→18

Refinement top

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1126P)²] where P = (F_o² + 2F_c²)/3
2893 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[V(C₉H₆NO)₂(CH₃O)O]	V = 1640.2 (3) Å³
M_r = 386.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.0405 (16) Å	µ = 0.63 mm⁻¹
b = 8.0019 (1) Å	T = 298 K
c = 15.5920 (18) Å	0.44 × 0.18 × 0.17 mm
β = 110.560 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2893 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1378 reflections with I > 2σ(I)
T_min = 0.768, T_max = 0.900	R_int = 0.102
7660 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.230	H-atom parameters constrained
S = 1.00	Δρ_max = 0.81 e Å⁻³
2893 reflections	Δρ_min = −0.69 e Å⁻³
235 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
V1	0.26796 (9)	0.67329 (14)	0.24257 (8)	0.0458 (5)
N1	0.3527 (4)	0.4493 (6)	0.3065 (4)	0.0403 (13)
N2	0.1379 (4)	0.4855 (6)	0.1896 (4)	0.0446 (14)
O1	0.2435 (3)	0.6607 (6)	0.3552 (3)	0.0536 (13)
O2	0.2803 (3)	0.5922 (6)	0.1345 (3)	0.0479 (12)
O3	0.1746 (3)	0.8276 (6)	0.2010 (4)	0.0592 (14)
O4	0.3700 (3)	0.7827 (5)	0.2732 (3)	0.0522 (13)
C1	0.4069 (5)	0.3432 (8)	0.2784 (5)	0.0504 (18)
H1	0.4035	0.3502	0.2178	0.060*
C2	0.4686 (5)	0.2221 (9)	0.3334 (6)	0.059 (2)
H2	0.5043	0.1480	0.3100	0.071*
C3	0.4762 (5)	0.2133 (8)	0.4233 (6)	0.058 (2)
H3	0.5189	0.1345	0.4618	0.069*
C4	0.4199 (5)	0.3227 (8)	0.4578 (5)	0.0426 (16)
C5	0.3577 (5)	0.4370 (7)	0.3952 (4)	0.0370 (15)
C6	0.2987 (5)	0.5570 (8)	0.4210 (5)	0.0427 (17)
C7	0.3040 (5)	0.5595 (9)	0.5099 (4)	0.0522 (19)
H7	0.2661	0.6366	0.5292	0.063*
C8	0.3665 (6)	0.4458 (10)	0.5716 (5)	0.060 (2)
H8	0.3695	0.4498	0.6321	0.072*
C9	0.4238 (5)	0.3288 (9)	0.5485 (5)	0.056 (2)
H9	0.4646	0.2549	0.5921	0.067*
C10	0.0644 (5)	0.4382 (8)	0.2193 (6)	0.061 (2)
H10	0.0650	0.4782	0.2755	0.073*
C11	−0.0131 (6)	0.3317 (10)	0.1701 (8)	0.078 (3)
H11	−0.0625	0.3005	0.1940	0.094*
C12	−0.0177 (6)	0.2729 (10)	0.0881 (8)	0.081 (3)
H12	−0.0704	0.2023	0.0550	0.097*
C13	0.0588 (6)	0.3196 (9)	0.0526 (6)	0.061 (2)
C14	0.1326 (5)	0.4281 (8)	0.1072 (5)	0.0467 (18)
C15	0.2132 (5)	0.4850 (8)	0.0794 (5)	0.0440 (17)
C16	0.2162 (6)	0.4307 (9)	−0.0033 (5)	0.058 (2)
H16	0.2679	0.4669	−0.0232	0.070*
C17	0.1425 (8)	0.3222 (11)	−0.0570 (6)	0.078 (3)
H17	0.1458	0.2859	−0.1125	0.094*
C18	0.0657 (7)	0.2675 (9)	−0.0307 (7)	0.076 (3)
H18	0.0172	0.1948	−0.0683	0.092*
C19	0.1912 (6)	1.0013 (10)	0.2138 (7)	0.088 (3)
H19A	0.1692	1.0385	0.2623	0.132*
H19B	0.1534	1.0588	0.1582	0.132*
H19C	0.2624	1.0246	0.2295	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0373 (7)	0.0496 (8)	0.0487 (8)	0.0070 (6)	0.0128 (6)	0.0060 (6)
N1	0.031 (3)	0.048 (3)	0.045 (4)	0.007 (3)	0.017 (3)	0.002 (3)
N2	0.034 (3)	0.044 (3)	0.057 (4)	0.010 (3)	0.018 (3)	0.014 (3)
O1	0.046 (3)	0.060 (3)	0.056 (3)	0.021 (2)	0.020 (3)	0.007 (3)
O2	0.035 (3)	0.058 (3)	0.050 (3)	−0.002 (2)	0.015 (2)	0.008 (2)
O3	0.044 (3)	0.060 (3)	0.072 (4)	0.012 (2)	0.018 (3)	0.014 (3)
O4	0.041 (3)	0.050 (3)	0.061 (3)	−0.003 (2)	0.012 (3)	0.004 (2)
C1	0.051 (4)	0.051 (4)	0.055 (5)	0.012 (4)	0.027 (4)	−0.001 (4)
C2	0.047 (5)	0.054 (5)	0.086 (7)	0.013 (4)	0.036 (5)	−0.001 (4)
C3	0.042 (4)	0.045 (4)	0.081 (6)	0.009 (3)	0.016 (4)	0.013 (4)
C4	0.033 (4)	0.045 (4)	0.048 (5)	0.001 (3)	0.010 (3)	0.012 (4)
C5	0.027 (3)	0.042 (4)	0.043 (4)	0.000 (3)	0.013 (3)	0.006 (3)
C6	0.028 (4)	0.049 (4)	0.048 (5)	−0.001 (3)	0.009 (3)	−0.002 (4)
C7	0.049 (5)	0.077 (5)	0.034 (4)	0.002 (4)	0.019 (4)	−0.005 (4)
C8	0.059 (5)	0.084 (6)	0.035 (4)	−0.012 (5)	0.014 (4)	0.001 (4)
C9	0.038 (4)	0.068 (5)	0.052 (5)	0.002 (4)	0.006 (4)	0.024 (4)
C10	0.040 (4)	0.055 (5)	0.098 (7)	0.010 (4)	0.037 (5)	0.013 (5)
C11	0.043 (5)	0.059 (6)	0.139 (10)	0.002 (4)	0.039 (6)	0.019 (6)
C12	0.033 (5)	0.050 (5)	0.135 (10)	0.000 (4)	−0.002 (6)	0.018 (6)
C13	0.046 (5)	0.053 (5)	0.064 (6)	0.004 (4)	−0.006 (4)	0.004 (4)
C14	0.039 (4)	0.036 (4)	0.057 (5)	0.009 (3)	0.006 (4)	0.010 (4)
C15	0.032 (4)	0.044 (4)	0.048 (5)	0.009 (3)	0.004 (4)	0.010 (4)
C16	0.056 (5)	0.070 (5)	0.047 (5)	0.018 (4)	0.017 (4)	−0.002 (4)
C17	0.089 (7)	0.069 (6)	0.059 (6)	0.013 (5)	0.004 (6)	−0.018 (5)
C18	0.071 (6)	0.043 (5)	0.077 (7)	0.002 (4)	−0.022 (5)	0.001 (5)
C19	0.061 (6)	0.072 (6)	0.135 (9)	0.015 (5)	0.040 (6)	0.016 (6)
C19	0.061 (6)	0.072 (6)	0.135 (9)	0.015 (5)	0.040 (6)	0.016 (6)

Geometric parameters (Å, º) top

V1—O4	1.602 (4)	C7—C8	1.390 (9)
V1—O3	1.752 (5)	C7—H7	0.9300
V1—O2	1.870 (5)	C8—C9	1.363 (9)
V1—O1	1.907 (5)	C8—H8	0.9300
V1—N1	2.188 (5)	C9—H9	0.9300
V1—N2	2.284 (6)	C10—C11	1.383 (11)
N1—C1	1.314 (7)	C10—H10	0.9300
N1—C5	1.364 (7)	C11—C12	1.341 (12)
N2—C10	1.326 (8)	C11—H11	0.9300
N2—C14	1.342 (8)	C12—C13	1.421 (12)
O1—C6	1.335 (7)	C12—H12	0.9300
O2—C15	1.339 (8)	C13—C14	1.390 (10)
O3—C19	1.412 (9)	C13—C18	1.400 (12)
C1—C2	1.380 (9)	C14—C15	1.422 (9)
C1—H1	0.9300	C15—C16	1.375 (9)
C2—C3	1.369 (10)	C16—C17	1.385 (11)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.408 (9)	C17—C18	1.353 (12)
C3—H3	0.9300	C17—H17	0.9300
C4—C9	1.397 (9)	C18—H18	0.9300
C4—C5	1.397 (8)	C19—H19A	0.9600
C5—C6	1.416 (8)	C19—H19B	0.9600
C6—C7	1.362 (8)	C19—H19C	0.9600

O4—V1—O3	101.5 (2)	C6—C7—C8	119.4 (7)
O4—V1—O2	95.9 (2)	C6—C7—H7	120.3
O3—V1—O2	101.9 (2)	C8—C7—H7	120.3
O4—V1—O1	100.7 (2)	C9—C8—C7	123.7 (7)
O3—V1—O1	91.4 (2)	C9—C8—H8	118.1
O2—V1—O1	156.3 (2)	C7—C8—H8	118.1
O4—V1—N1	91.5 (2)	C8—C9—C4	118.3 (7)
O3—V1—N1	164.3 (2)	C8—C9—H9	120.8
O2—V1—N1	85.35 (19)	C4—C9—H9	120.8
O1—V1—N1	77.40 (19)	N2—C10—C11	122.6 (8)
O4—V1—N2	170.1 (2)	N2—C10—H10	118.7
O3—V1—N2	86.0 (2)	C11—C10—H10	118.7
O2—V1—N2	76.2 (2)	C12—C11—C10	120.8 (8)
O1—V1—N2	85.3 (2)	C12—C11—H11	119.6
N1—V1—N2	82.15 (19)	C10—C11—H11	119.6
C1—N1—C5	117.5 (6)	C11—C12—C13	119.2 (8)
C1—N1—V1	131.5 (5)	C11—C12—H12	120.4
C5—N1—V1	110.4 (4)	C13—C12—H12	120.4
C10—N2—C14	116.6 (6)	C14—C13—C18	118.4 (8)
C10—N2—V1	133.1 (5)	C14—C13—C12	115.4 (8)
C14—N2—V1	109.9 (4)	C18—C13—C12	126.2 (9)
C6—O1—V1	119.8 (4)	N2—C14—C13	125.4 (7)
C15—O2—V1	122.2 (4)	N2—C14—C15	113.6 (6)
C19—O3—V1	125.2 (5)	C13—C14—C15	121.0 (8)
N1—C1—C2	123.9 (7)	O2—C15—C16	123.9 (6)
N1—C1—H1	118.1	O2—C15—C14	117.8 (6)
C2—C1—H1	118.1	C16—C15—C14	118.3 (7)
C3—C2—C1	118.6 (6)	C15—C16—C17	120.1 (8)
C3—C2—H2	120.7	C15—C16—H16	119.9
C1—C2—H2	120.7	C17—C16—H16	119.9
C2—C3—C4	120.5 (7)	C18—C17—C16	121.7 (8)
C2—C3—H3	119.7	C18—C17—H17	119.1
C4—C3—H3	119.7	C16—C17—H17	119.1
C9—C4—C5	118.5 (6)	C17—C18—C13	120.4 (8)
C9—C4—C3	125.5 (7)	C17—C18—H18	119.8
C5—C4—C3	115.9 (6)	C13—C18—H18	119.8
N1—C5—C4	123.6 (6)	O3—C19—H19A	109.5
N1—C5—C6	114.3 (6)	O3—C19—H19B	109.5
C4—C5—C6	122.0 (6)	H19A—C19—H19B	109.5
O1—C6—C7	125.6 (6)	O3—C19—H19C	109.5
O1—C6—C5	116.3 (6)	H19A—C19—H19C	109.5
C7—C6—C5	118.1 (6)	H19B—C19—H19C	109.5

O4—V1—N1—C1	−80.2 (6)	C9—C4—C5—N1	175.8 (6)
O3—V1—N1—C1	133.7 (9)	C3—C4—C5—N1	−2.3 (9)
O2—V1—N1—C1	15.5 (6)	C9—C4—C5—C6	−0.4 (9)
O1—V1—N1—C1	179.1 (6)	C3—C4—C5—C6	−178.5 (6)
N2—V1—N1—C1	92.2 (6)	V1—O1—C6—C7	165.8 (5)
O4—V1—N1—C5	90.4 (4)	V1—O1—C6—C5	−12.9 (7)
O3—V1—N1—C5	−55.8 (10)	N1—C5—C6—O1	2.5 (8)
O2—V1—N1—C5	−173.9 (4)	C4—C5—C6—O1	179.1 (5)
O1—V1—N1—C5	−10.3 (4)	N1—C5—C6—C7	−176.3 (6)
N2—V1—N1—C5	−97.2 (4)	C4—C5—C6—C7	0.3 (9)
O3—V1—N2—C10	−74.5 (6)	O1—C6—C7—C8	−178.6 (6)
O2—V1—N2—C10	−177.7 (6)	C5—C6—C7—C8	0.1 (10)
O1—V1—N2—C10	17.3 (6)	C6—C7—C8—C9	−0.3 (11)
N1—V1—N2—C10	95.2 (6)	C7—C8—C9—C4	0.2 (11)
O3—V1—N2—C14	97.8 (4)	C5—C4—C9—C8	0.2 (10)
O2—V1—N2—C14	−5.4 (4)	C3—C4—C9—C8	178.1 (6)
O1—V1—N2—C14	−170.4 (4)	C14—N2—C10—C11	1.6 (10)
N1—V1—N2—C14	−92.5 (4)	V1—N2—C10—C11	173.5 (5)
O4—V1—O1—C6	−76.6 (5)	N2—C10—C11—C12	−1.0 (12)
O3—V1—O1—C6	−178.6 (5)	C10—C11—C12—C13	0.8 (12)
O2—V1—O1—C6	56.9 (7)	C11—C12—C13—C14	−1.3 (11)
N1—V1—O1—C6	12.6 (4)	C11—C12—C13—C18	179.0 (8)
N2—V1—O1—C6	95.6 (5)	C10—N2—C14—C13	−2.3 (9)
O4—V1—O2—C15	178.2 (5)	V1—N2—C14—C13	−176.0 (5)
O3—V1—O2—C15	−78.7 (5)	C10—N2—C14—C15	179.5 (5)
O1—V1—O2—C15	44.0 (7)	V1—N2—C14—C15	5.8 (6)
N1—V1—O2—C15	87.2 (5)	C18—C13—C14—N2	−178.1 (6)
N2—V1—O2—C15	4.1 (4)	C12—C13—C14—N2	2.1 (10)
O4—V1—O3—C19	−12.4 (7)	C18—C13—C14—C15	0.0 (10)
O2—V1—O3—C19	−111.0 (6)	C12—C13—C14—C15	−179.8 (6)
O1—V1—O3—C19	88.8 (6)	V1—O2—C15—C16	175.9 (5)
N1—V1—O3—C19	132.9 (8)	V1—O2—C15—C14	−2.3 (8)
N2—V1—O3—C19	174.0 (6)	N2—C14—C15—O2	−3.1 (8)
C5—N1—C1—C2	−0.5 (10)	C13—C14—C15—O2	178.6 (6)
V1—N1—C1—C2	169.5 (5)	N2—C14—C15—C16	178.6 (6)
N1—C1—C2—C3	−1.6 (11)	C13—C14—C15—C16	0.3 (10)
C1—C2—C3—C4	1.8 (11)	O2—C15—C16—C17	−178.7 (6)
C2—C3—C4—C9	−177.9 (7)	C14—C15—C16—C17	−0.5 (10)
C2—C3—C4—C5	0.0 (9)	C15—C16—C17—C18	0.4 (12)
C1—N1—C5—C4	2.5 (9)	C16—C17—C18—C13	−0.1 (13)
V1—N1—C5—C4	−169.6 (5)	C14—C13—C18—C17	−0.1 (11)
C1—N1—C5—C6	179.0 (6)	C12—C13—C18—C17	179.6 (8)
V1—N1—C5—C6	6.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4ⁱ	0.93	2.54	3.355 (8)	146
C19—H19B···Cgⁱⁱ	0.96	2.84	3.520 (9)	128

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[V(C₉H₆NO)₂(CH₃O)O]
M_r	386.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.0405 (16), 8.0019 (1), 15.5920 (18)
β (°)	110.560 (1)
V (Å³)	1640.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.44 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.768, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	7660, 2893, 1378
R_int	0.102
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.230, 1.00
No. of reflections	2893
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.69

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Selected bond angles (º) top

O3—V1—O2	101.9 (2)	O2—V1—N1	85.35 (19)
O3—V1—O1	91.4 (2)	O1—V1—N1	77.40 (19)
O2—V1—O1	156.3 (2)	O4—V1—N2	170.1 (2)
O3—V1—N1	164.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O4ⁱ	0.93	2.54	3.355 (8)	145.8
C19—H19B···Cgⁱⁱ	0.96	2.84	3.520 (9)	128

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z.

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (No. Y2004B02) for a research grant.

References

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