Methoxo[N′-(3-meth­oxy-2-oxidobenzyl­idene)benzohydrazidato]oxidovanadium(V)

Huang, S.-M.; Jiang, F.-F.; Chen, X.-H.; Wu, Q.-J.

doi:10.1107/S1600536810009608

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m456

doi:10.1107/S1600536810009608

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Methoxo[N′-(3-methoxy-2-oxidobenzylidene)benzohydrazidato]oxidovanadium(V)

Shu-Mei Huang,^a Fei-Feng Jiang,^a Xiao-Hua Chen ^a ^* and Qiong-Jie Wu ^b

^aCollege of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350007, People's Republic of China, and ^bCollege of Life Science, Fujian Agriculture and Forestry University, Fuzhou, Fujian 350002, People's Republic of China
^*Correspondence e-mail: xiaohuachen03@163.com

(Received 1 March 2010; accepted 14 March 2010; online 27 March 2010)

In the title complex, [V(C₁₅H₁₂N₂O₄)(CH₃O)O], the V^V ion exhibits a distorted square-pyramidal coordination geometry; three donor atoms from a hydrazone ligand and one O atom of the deprotonated methanol define the coordination basal plane. The V^V ion is displaced by 0.464 (1) Å from the basal plane towards the axial oxide O atom. Intramolecular O—H⋯N hydrogen bonding occurs. Intermolecular C—H⋯O hydrogen bonding is also observed in the crystal structure.

Related literature

For general background to hydrazones and their chelation ability, see: Liu & Gao (1998 ); Ma et al. (1989 ); Sur et al. (1993 ); Sun et al. (2005 ). For related structures, see: Chen et al. (2004 ); Liu et al. (2006 ); Ghosh et al. (2007 ); Seena et al. (2008 ). For the synthesis, see: Gao et al. (1998 ); Chen (2008 ).

Experimental

Crystal data

[V(C₁₅H₁₂N₂O₄)(CH₃O)O]
M_r = 382.24
Monoclinic, P 2₁ /c
a = 16.194 (3) Å
b = 6.6746 (13) Å
c = 15.359 (3) Å
β = 96.89 (3)°
V = 1648.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 293 K
0.39 × 0.22 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ) T_min = 0.845, T_max = 0.909
14918 measured reflections
3686 independent reflections
2776 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.08
3686 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O1	1.8277 (17)
V1—O3	1.9436 (16)
V1—O5	1.5736 (18)
V1—O6	1.7351 (16)
V1—N1	2.0963 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯N2	0.82	1.84	2.568 (2)	147
C8—H8A⋯O4ⁱ	0.93	2.32	3.243 (3)	169
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009608/xu2731sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009608/xu2731Isup2.hkl

checkCIF report

Comment top

Hydrazones are of interest owing to their capacity for chelating to transition (Sur et al., 1993; Sun, et al., 2005), lanthanide (Ma et al., 1989) and main group (Liu & Gao 1998) metals.

The V^V ion exists in a distorted square-pyramidal coordination geometry. Three donor atoms (O1, O3 and N1) of the hydrozone ligand and O6 atom from the methanol group define the coordination basal plane, with a maximum mean plane deviation of 0.0215 (9) Å. The V atom is displaced towards the axial oxo O atom by 0.464 (1)Å from the basal plane. Bond distances (Table 1) and bond angles around V1 atom are compared with those in reported oxovanadium complexes (Chen et al., 2004; Seena et al., 2008; Liu et al.,2006; Ghosh et al., 2007). In the crystal structure there are the intramolecular O—H···N hydrogen bonding and intermolecular C—H···O hydrogen bonding (Table 2).

Related literature top

For general background to hydrazones and their chelation ability, see: Liu & Gao (1998); Ma et al. (1989); Sur et al. (1993); Sun et al. (2005). For related structures, see: Chen et al. (2004); Liu et al. (2006); Ghosh et al. (2007); Seena et al. (2008). For the synthesis, see: Gao et al. (1998); Chen (2008).

Experimental top

VO(acac)₂ (acac = acetylacetonate) was synthesized according to the reported method (Gao et al., 1998). The hydrazone ligand (L) was prepared by following a similar procedure reported by Chen (2008).

The title compound was prepared by reacting H₂L (0.1 mmol) with VO(acac)₂ (0.1 mmol) in methnol/water solution (10 ml) with stirring. The solution was filtered and allowed to stand at room temperature for one week, dark-red crystals of complex (I) were obtained.

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms. A dashed line indicates the intramoleculat hydrogen bonding.

Methoxo[N'-(3-methoxy-2- oxidobenzylidene)benzohydrazidato]oxidovanadium(V) top

Crystal data top

[V(C₁₅H₁₂N₂O₄)(CH₃O)O]	F(000) = 784
M_r = 382.24	D_x = 1.541 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2776 reflections
a = 16.194 (3) Å	θ = 3.1–27.5°
b = 6.6746 (13) Å	µ = 0.64 mm⁻¹
c = 15.359 (3) Å	T = 293 K
β = 96.89 (3)°	Prism, dark-red
V = 1648.1 (6) Å³	0.39 × 0.22 × 0.15 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3686 independent reflections
Radiation source: fine-focus sealed tube	2776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −21→21
T_min = 0.845, T_max = 0.909	k = −8→8
14918 measured reflections	l = −19→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.062P)² + 0.2985P] where P = (F_o² + 2F_c²)/3
3686 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[V(C₁₅H₁₂N₂O₄)(CH₃O)O]	V = 1648.1 (6) Å³
M_r = 382.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.194 (3) Å	µ = 0.64 mm⁻¹
b = 6.6746 (13) Å	T = 293 K
c = 15.359 (3) Å	0.39 × 0.22 × 0.15 mm
β = 96.89 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3686 independent reflections
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	2776 reflections with I > 2σ(I)
T_min = 0.845, T_max = 0.909	R_int = 0.051
14918 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.08	Δρ_max = 0.33 e Å⁻³
3686 reflections	Δρ_min = −0.39 e Å⁻³
228 parameters

Special details top

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 > 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	0.16311 (2)	0.04276 (6)	0.66648 (3)	0.04096 (14)
O1	0.16555 (9)	0.2270 (2)	0.57877 (11)	0.0533 (4)
O2	0.09673 (11)	0.5226 (3)	0.48044 (13)	0.0624 (5)
O3	0.21107 (9)	−0.1967 (2)	0.72412 (10)	0.0464 (4)
O4	0.46575 (11)	−0.2270 (3)	0.81503 (15)	0.0860 (7)
H4B	0.4400	−0.1379	0.7867	0.129*
O5	0.13675 (10)	0.1611 (3)	0.74736 (12)	0.0599 (5)
O6	0.07767 (10)	−0.0955 (3)	0.62167 (11)	0.0561 (4)
N1	0.29210 (10)	0.0886 (3)	0.68123 (11)	0.0377 (4)
N2	0.33889 (10)	−0.0525 (3)	0.73138 (12)	0.0411 (4)
C1	0.21307 (13)	0.3854 (3)	0.56461 (14)	0.0432 (5)
C2	0.29647 (12)	0.3942 (3)	0.59948 (13)	0.0390 (5)
C3	0.34579 (14)	0.5570 (3)	0.57913 (16)	0.0487 (6)
H3A	0.4017	0.5617	0.6015	0.058*
C4	0.31173 (16)	0.7083 (4)	0.52658 (16)	0.0562 (6)
H4A	0.3445	0.8155	0.5129	0.067*
C5	0.22816 (16)	0.7015 (4)	0.49361 (16)	0.0554 (6)
H5A	0.2052	0.8063	0.4588	0.066*
C6	0.17849 (14)	0.5428 (4)	0.51131 (15)	0.0488 (5)
C7	0.05967 (18)	0.6762 (5)	0.4246 (2)	0.0739 (8)
H7A	0.0016	0.6478	0.4095	0.111*
H7B	0.0865	0.6818	0.3722	0.111*
H7C	0.0659	0.8027	0.4544	0.111*
C8	0.33318 (12)	0.2369 (3)	0.65380 (14)	0.0406 (5)
H8A	0.3903	0.2414	0.6705	0.049*
C9	0.29058 (12)	−0.1970 (3)	0.75157 (14)	0.0397 (5)
C10	0.32708 (14)	−0.3646 (3)	0.80484 (14)	0.0431 (5)
C11	0.41233 (15)	−0.3729 (4)	0.83309 (17)	0.0577 (6)
C12	0.44452 (19)	−0.5360 (5)	0.8821 (2)	0.0744 (9)
H12A	0.5014	−0.5432	0.9001	0.089*
C13	0.3936 (2)	−0.6854 (5)	0.90395 (19)	0.0723 (8)
H13A	0.4162	−0.7932	0.9370	0.087*
C14	0.3096 (2)	−0.6792 (4)	0.87791 (17)	0.0642 (7)
H14A	0.2753	−0.7815	0.8937	0.077*
C15	0.27640 (16)	−0.5201 (4)	0.82817 (16)	0.0508 (6)
H15A	0.2195	−0.5164	0.8099	0.061*
C16	0.00782 (18)	−0.1796 (5)	0.6540 (2)	0.0879 (10)
H16A	−0.0371	−0.1897	0.6073	0.132*
H16B	−0.0088	−0.0958	0.6997	0.132*
H16C	0.0216	−0.3106	0.6771	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.02696 (19)	0.0439 (2)	0.0521 (2)	−0.00458 (14)	0.00533 (14)	0.00005 (17)
O1	0.0359 (8)	0.0547 (10)	0.0670 (10)	−0.0086 (7)	−0.0028 (7)	0.0155 (9)
O2	0.0453 (9)	0.0705 (11)	0.0685 (11)	−0.0006 (8)	−0.0056 (8)	0.0233 (10)
O3	0.0364 (8)	0.0468 (9)	0.0555 (9)	−0.0077 (6)	0.0038 (6)	0.0039 (8)
O4	0.0380 (9)	0.0995 (15)	0.1183 (17)	0.0049 (10)	0.0011 (10)	0.0564 (14)
O5	0.0471 (9)	0.0652 (11)	0.0693 (11)	0.0029 (8)	0.0147 (8)	−0.0103 (9)
O6	0.0390 (8)	0.0612 (10)	0.0664 (11)	−0.0148 (7)	−0.0006 (7)	0.0052 (9)
N1	0.0290 (8)	0.0415 (9)	0.0428 (9)	−0.0003 (7)	0.0047 (7)	−0.0014 (8)
N2	0.0316 (8)	0.0416 (10)	0.0498 (10)	0.0015 (7)	0.0034 (7)	0.0016 (8)
C1	0.0384 (11)	0.0482 (12)	0.0440 (12)	−0.0035 (9)	0.0093 (9)	0.0036 (10)
C2	0.0353 (10)	0.0434 (11)	0.0395 (11)	−0.0033 (8)	0.0093 (8)	−0.0034 (10)
C3	0.0429 (12)	0.0551 (14)	0.0493 (13)	−0.0115 (10)	0.0105 (10)	0.0000 (11)
C4	0.0586 (15)	0.0576 (15)	0.0542 (14)	−0.0149 (12)	0.0146 (11)	0.0099 (13)
C5	0.0616 (15)	0.0556 (15)	0.0497 (13)	−0.0044 (12)	0.0096 (11)	0.0153 (12)
C6	0.0451 (12)	0.0575 (14)	0.0440 (12)	0.0000 (10)	0.0063 (10)	0.0059 (11)
C7	0.0635 (17)	0.083 (2)	0.0713 (18)	0.0100 (15)	−0.0089 (14)	0.0247 (17)
C8	0.0290 (9)	0.0464 (12)	0.0469 (12)	−0.0031 (8)	0.0069 (8)	−0.0045 (10)
C9	0.0355 (10)	0.0433 (11)	0.0407 (11)	0.0005 (9)	0.0067 (8)	−0.0054 (10)
C10	0.0500 (12)	0.0418 (12)	0.0392 (11)	0.0033 (9)	0.0115 (9)	−0.0041 (10)
C11	0.0471 (13)	0.0680 (16)	0.0588 (15)	0.0118 (12)	0.0101 (11)	0.0116 (14)
C12	0.0619 (17)	0.085 (2)	0.077 (2)	0.0244 (16)	0.0101 (15)	0.0246 (17)
C13	0.095 (2)	0.0673 (19)	0.0561 (16)	0.0218 (17)	0.0154 (15)	0.0142 (15)
C14	0.098 (2)	0.0459 (14)	0.0519 (15)	−0.0048 (14)	0.0225 (14)	0.0012 (13)
C15	0.0631 (15)	0.0473 (13)	0.0436 (12)	−0.0025 (11)	0.0127 (11)	−0.0072 (11)
C16	0.0597 (17)	0.101 (2)	0.103 (2)	−0.0432 (17)	0.0113 (16)	0.004 (2)

Geometric parameters (Å, º) top

V1—O1	1.8277 (17)	C4—H4A	0.9300
V1—O3	1.9436 (16)	C5—C6	1.377 (3)
V1—O5	1.5736 (18)	C5—H5A	0.9300
V1—O6	1.7351 (16)	C7—H7A	0.9600
V1—N1	2.0963 (17)	C7—H7B	0.9600
O1—C1	1.341 (3)	C7—H7C	0.9600
O2—C6	1.358 (3)	C8—H8A	0.9300
O2—C7	1.423 (3)	C9—C10	1.467 (3)
O3—C9	1.306 (2)	C10—C15	1.397 (3)
O4—C11	1.353 (3)	C10—C11	1.398 (3)
O4—H4B	0.8200	C11—C12	1.389 (4)
O6—C16	1.406 (3)	C12—C13	1.361 (4)
N1—C8	1.292 (3)	C12—H12A	0.9300
N1—N2	1.384 (2)	C13—C14	1.372 (4)
N2—C9	1.303 (3)	C13—H13A	0.9300
C1—C2	1.393 (3)	C14—C15	1.379 (4)
C1—C6	1.406 (3)	C14—H14A	0.9300
C2—C3	1.405 (3)	C15—H15A	0.9300
C2—C8	1.426 (3)	C16—H16A	0.9600
C3—C4	1.367 (3)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
C4—C5	1.388 (3)

O5—V1—O6	107.53 (9)	O2—C7—H7A	109.5
O5—V1—O1	106.03 (9)	O2—C7—H7B	109.5
O6—V1—O1	98.75 (8)	H7A—C7—H7B	109.5
O5—V1—O3	100.64 (8)	O2—C7—H7C	109.5
O6—V1—O3	89.96 (7)	H7A—C7—H7C	109.5
O1—V1—O3	147.80 (7)	H7B—C7—H7C	109.5
O5—V1—N1	101.68 (8)	N1—C8—C2	124.10 (18)
O6—V1—N1	149.00 (8)	N1—C8—H8A	118.0
O1—V1—N1	82.66 (7)	C2—C8—H8A	118.0
O3—V1—N1	74.46 (6)	N2—C9—O3	121.3 (2)
C1—O1—V1	135.54 (14)	N2—C9—C10	118.93 (19)
C6—O2—C7	117.5 (2)	O3—C9—C10	119.78 (19)
C9—O3—V1	118.22 (14)	C15—C10—C11	118.7 (2)
C11—O4—H4B	109.5	C15—C10—C9	120.0 (2)
C16—O6—V1	135.18 (19)	C11—C10—C9	121.3 (2)
C8—N1—N2	115.74 (16)	O4—C11—C12	117.9 (2)
C8—N1—V1	128.47 (14)	O4—C11—C10	122.7 (2)
N2—N1—V1	115.67 (12)	C12—C11—C10	119.5 (3)
C9—N2—N1	109.38 (16)	C13—C12—C11	120.6 (3)
O1—C1—C2	121.3 (2)	C13—C12—H12A	119.7
O1—C1—C6	119.17 (19)	C11—C12—H12A	119.7
C2—C1—C6	119.5 (2)	C12—C13—C14	121.0 (3)
C1—C2—C3	119.8 (2)	C12—C13—H13A	119.5
C1—C2—C8	120.72 (19)	C14—C13—H13A	119.5
C3—C2—C8	119.42 (19)	C13—C14—C15	119.4 (3)
C4—C3—C2	120.2 (2)	C13—C14—H14A	120.3
C4—C3—H3A	119.9	C15—C14—H14A	120.3
C2—C3—H3A	119.9	C14—C15—C10	120.8 (3)
C3—C4—C5	119.9 (2)	C14—C15—H15A	119.6
C3—C4—H4A	120.1	C10—C15—H15A	119.6
C5—C4—H4A	120.1	O6—C16—H16A	109.5
C6—C5—C4	121.4 (2)	O6—C16—H16B	109.5
C6—C5—H5A	119.3	H16A—C16—H16B	109.5
C4—C5—H5A	119.3	O6—C16—H16C	109.5
O2—C6—C5	125.1 (2)	H16A—C16—H16C	109.5
O2—C6—C1	115.6 (2)	H16B—C16—H16C	109.5
C5—C6—C1	119.2 (2)

O5—V1—O1—C1	68.2 (2)	C7—O2—C6—C5	0.8 (4)
O6—V1—O1—C1	179.4 (2)	C7—O2—C6—C1	−178.6 (2)
O3—V1—O1—C1	−76.5 (3)	C4—C5—C6—O2	−178.7 (2)
N1—V1—O1—C1	−31.9 (2)	C4—C5—C6—C1	0.6 (4)
O5—V1—O3—C9	−90.59 (16)	O1—C1—C6—O2	2.2 (3)
O6—V1—O3—C9	161.58 (15)	C2—C1—C6—O2	−179.7 (2)
O1—V1—O3—C9	55.0 (2)	O1—C1—C6—C5	−177.2 (2)
N1—V1—O3—C9	8.72 (14)	C2—C1—C6—C5	0.9 (3)
O5—V1—O6—C16	−27.1 (3)	N2—N1—C8—C2	178.26 (18)
O1—V1—O6—C16	−137.1 (3)	V1—N1—C8—C2	−6.0 (3)
O3—V1—O6—C16	74.0 (3)	C1—C2—C8—N1	−6.8 (3)
N1—V1—O6—C16	132.6 (3)	C3—C2—C8—N1	174.9 (2)
O5—V1—N1—C8	−85.9 (2)	N1—N2—C9—O3	1.1 (3)
O6—V1—N1—C8	113.8 (2)	N1—N2—C9—C10	179.94 (17)
O1—V1—N1—C8	18.99 (19)	V1—O3—C9—N2	−8.7 (3)
O3—V1—N1—C8	176.1 (2)	V1—O3—C9—C10	172.45 (14)
O5—V1—N1—N2	89.78 (15)	N2—C9—C10—C15	179.3 (2)
O6—V1—N1—N2	−70.5 (2)	O3—C9—C10—C15	−1.9 (3)
O1—V1—N1—N2	−165.29 (15)	N2—C9—C10—C11	−0.8 (3)
O3—V1—N1—N2	−8.15 (13)	O3—C9—C10—C11	178.0 (2)
C8—N1—N2—C9	−177.45 (19)	C15—C10—C11—O4	−178.7 (3)
V1—N1—N2—C9	6.3 (2)	C9—C10—C11—O4	1.5 (4)
V1—O1—C1—C2	29.7 (3)	C15—C10—C11—C12	1.0 (4)
V1—O1—C1—C6	−152.29 (18)	C9—C10—C11—C12	−178.9 (2)
O1—C1—C2—C3	176.2 (2)	O4—C11—C12—C13	178.6 (3)
C6—C1—C2—C3	−1.8 (3)	C10—C11—C12—C13	−1.1 (5)
O1—C1—C2—C8	−2.0 (3)	C11—C12—C13—C14	0.3 (5)
C6—C1—C2—C8	180.0 (2)	C12—C13—C14—C15	0.6 (4)
C1—C2—C3—C4	1.2 (3)	C13—C14—C15—C10	−0.7 (4)
C8—C2—C3—C4	179.5 (2)	C11—C10—C15—C14	−0.1 (3)
C2—C3—C4—C5	0.3 (4)	C9—C10—C15—C14	179.7 (2)
C3—C4—C5—C6	−1.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N2	0.82	1.84	2.568 (2)	147
C8—H8A···O4ⁱ	0.93	2.32	3.243 (3)	169

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[V(C₁₅H₁₂N₂O₄)(CH₃O)O]
M_r	382.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.194 (3), 6.6746 (13), 15.359 (3)
β (°)	96.89 (3)
V (Å³)	1648.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.39 × 0.22 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (TEXRAY; Molecular Structure Corporation, 1999)
T_min, T_max	0.845, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	14918, 3686, 2776
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.08
No. of reflections	3686
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.39

Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEX (McArdle, 1995).

Selected bond lengths (Å) top

V1—O1	1.8277 (17)	V1—O6	1.7351 (16)
V1—O3	1.9436 (16)	V1—N1	2.0963 (17)
V1—O5	1.5736 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N2	0.82	1.84	2.568 (2)	146.7
C8—H8A···O4ⁱ	0.93	2.32	3.243 (3)	169.0

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors acknowledge financial support from the Undergraduate Students' Extracurricular Technology Project of Fujian Normal University, China (grant No. BKL2009–045).

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