(Ethano­lato-κO)[N′-(3-meth­oxy-2-oxidobenzyl­idene-κO2)benzo­hydrazidato-κ2N′,O]oxidovanadium(V)

Chen, X.-H.; Wu, Q.-J.; Chen, L.-J.; Yang, M.-X.

doi:10.1107/S1600536812032229

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages m1101-m1102

https://doi.org/10.1107/S1600536812032229

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(Ethanolato-κO)[N′-(3-methoxy-2-oxidobenzylidene-κO²)benzohydrazidato-κ²N′,O]oxidovanadium(V)

Xiao-Hua Chen,^a ^* Qiong-Jie Wu,^b Li-Juan Chen ^c and Ming-Xing Yang ^c

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

(Received 30 June 2012; accepted 15 July 2012; online 21 July 2012)

In the title complex, [V(C₁₅H₁₂N₂O₄)(C₂H₅O)O], the V^V ion is coordinated by an oxide O atom, an ethanolate anion and two O atoms and one N atom from the tridentate benzohydrazidate dianion in a distorted square-pyramidal geometry; the V atom is displaced by 0.4748 (8) Å from the basal plane towards the axial oxide O atom. An intramolecular O—H⋯N hydrogen bond occurs in the benzohydrazidate ligand. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal.

Related literature

For general background to the coordination chemistry and biochemisty of vanadium, see: Deng et al. (2007 ); Monfared et al. (2011 ); Sutradhar et al. (2006 ). 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 ); Huang et al. (2010 ).

Experimental

Crystal data

[V(C₁₅H₁₂N₂O₄)(C₂H₅O)O]
M_r = 396.27
Monoclinic, P 2₁ /c
a = 15.808 (5) Å
b = 6.606 (2) Å
c = 16.693 (8) Å
β = 94.107 (16)°
V = 1738.6 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 293 K
0.37 × 0.25 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ) T_min = 0.834, T_max = 0.924
15371 measured reflections
3968 independent reflections
3243 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.08
3968 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—N1	2.1029 (15)
V1—O1	1.8325 (14)
V1—O3	1.9453 (14)
V1—O5	1.5762 (15)
V1—O6	1.7423 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯N2	0.82	1.86	2.581 (2)	147
C8—H8A⋯O4ⁱ	0.93	2.31	3.236 (2)	177
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536812032229/xu5587sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032229/xu5587Isup2.hkl

checkCIF report

Comment top

In the recent years, the coordination chemistry and biochemisty of vanadium has received considerable attention (Deng et al., 2007; Monfared et al., 2011; Sutradhar et al., 2006). Generally, a tridentate hydrazone ligand is coordinated to the vanadium through O and N atoms, similar to those of the biological system. So, it is important to intensively study the relation ship of the syntheses and structural properties of vanadium hydrazone complexes.

In the title complex, [VO(C₁₅H₁₂N₂O₄)(C₂H₅O)], 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 ethanol group define the coordination basal plane, with a maximum mean plane deviation of 0.030 (1) Å. The V atom is displaced towards the axial oxo O atom by 0.4748 (8) 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 the coordination chemistry and biochemisty of vanadium, see: Deng et al. (2007); Monfared et al. (2011); Sutradhar et al. (2006). 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); Huang et al. (2010).

Experimental top

VO(acac)₂ (acac = acetylacetonate) was synthesized according to the reported method of Gao et al. (1998). The synthesis of the hydrazone ligand has already been reported in the literature (Huang et al., 2010).

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

Structure description top

For general background to the coordination chemistry and biochemisty of vanadium, see: Deng et al. (2007); Monfared et al. (2011); Sutradhar et al. (2006). 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); Huang et al. (2010).

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.

(Ethanolato-κO)[N'-(3-methoxy-2- oxidobenzylidene-κO²)benzohydrazidato- κ²N',O]oxidovanadium(V) top

Crystal data top

[V(C₁₅H₁₂N₂O₄)(C₂H₅O)O]	F(000) = 816
M_r = 396.27	D_x = 1.514 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3243 reflections
a = 15.808 (5) Å	θ = 3.3–27.5°
b = 6.606 (2) Å	µ = 0.61 mm⁻¹
c = 16.693 (8) Å	T = 293 K
β = 94.107 (16)°	Prism, dark-red
V = 1738.6 (12) Å³	0.37 × 0.25 × 0.13 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3968 independent reflections
Radiation source: fine-focus sealed tube	3243 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −19→20
T_min = 0.834, T_max = 0.924	k = −8→7
15371 measured reflections	l = −21→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0564P)² + 0.3657P] where P = (F_o² + 2F_c²)/3
3968 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[V(C₁₅H₁₂N₂O₄)(C₂H₅O)O]	V = 1738.6 (12) Å³
M_r = 396.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.808 (5) Å	µ = 0.61 mm⁻¹
b = 6.606 (2) Å	T = 293 K
c = 16.693 (8) Å	0.37 × 0.25 × 0.13 mm
β = 94.107 (16)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3968 independent reflections
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	3243 reflections with I > 2σ(I)
T_min = 0.834, T_max = 0.924	R_int = 0.041
15371 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.08	Δρ_max = 0.34 e Å⁻³
3968 reflections	Δρ_min = −0.22 e Å⁻³
237 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	0.327165 (17)	0.03858 (5)	0.379657 (17)	0.03227 (11)
O1	0.30812 (8)	0.2237 (2)	0.45811 (8)	0.0442 (3)
O2	0.35894 (10)	0.5229 (2)	0.55498 (9)	0.0496 (4)
O3	0.28941 (8)	−0.2038 (2)	0.32138 (8)	0.0407 (3)
O4	0.04552 (9)	−0.2451 (3)	0.20545 (12)	0.0782 (6)
H4B	0.0647	−0.1583	0.2368	0.117*
O5	0.36775 (9)	0.1609 (2)	0.31098 (9)	0.0516 (4)
O6	0.40591 (8)	−0.1056 (2)	0.43088 (8)	0.0435 (3)
N1	0.19698 (9)	0.0812 (2)	0.34927 (8)	0.0328 (3)
N2	0.15908 (9)	−0.0609 (2)	0.29735 (9)	0.0372 (4)
C1	0.25579 (11)	0.3816 (3)	0.46463 (10)	0.0357 (4)
C2	0.17609 (11)	0.3877 (3)	0.42268 (10)	0.0358 (4)
C3	0.12022 (13)	0.5497 (3)	0.43503 (12)	0.0472 (5)
H3A	0.0668	0.5530	0.4077	0.057*
C4	0.14474 (15)	0.7014 (4)	0.48709 (13)	0.0546 (6)
H4A	0.1078	0.8079	0.4952	0.065*
C5	0.22441 (14)	0.6982 (3)	0.52816 (12)	0.0488 (5)
H5A	0.2402	0.8029	0.5633	0.059*
C6	0.28039 (13)	0.5414 (3)	0.51739 (11)	0.0394 (4)
C7	0.38639 (16)	0.6801 (4)	0.60921 (14)	0.0617 (6)
H7A	0.4451	0.6602	0.6263	0.092*
H7B	0.3531	0.6772	0.6551	0.092*
H7C	0.3795	0.8087	0.5828	0.092*
C8	0.14914 (11)	0.2298 (3)	0.36837 (11)	0.0366 (4)
H8A	0.0938	0.2341	0.3453	0.044*
C9	0.21338 (11)	−0.2052 (3)	0.28567 (10)	0.0342 (4)
C10	0.18783 (11)	−0.3739 (3)	0.23241 (10)	0.0353 (4)
C11	0.10557 (12)	−0.3869 (4)	0.19530 (13)	0.0471 (5)
C12	0.08370 (15)	−0.5527 (4)	0.14672 (14)	0.0570 (6)
H12A	0.0287	−0.5640	0.1234	0.068*
C13	0.14231 (15)	−0.6997 (4)	0.13284 (13)	0.0541 (5)
H13A	0.1269	−0.8090	0.0998	0.065*
C14	0.22383 (15)	−0.6862 (3)	0.16759 (13)	0.0509 (5)
H14A	0.2636	−0.7851	0.1575	0.061*
C15	0.24613 (13)	−0.5261 (3)	0.21720 (11)	0.0409 (4)
H15A	0.3010	−0.5186	0.2411	0.049*
C16	0.47854 (16)	−0.2211 (5)	0.41625 (15)	0.0726 (8)
H16A	0.4651	−0.3632	0.4225	0.087*
H16B	0.5233	−0.1876	0.4569	0.087*
C17	0.51099 (16)	−0.1928 (5)	0.33759 (16)	0.0734 (8)
H17A	0.5644	−0.2613	0.3359	0.110*
H17B	0.5186	−0.0510	0.3279	0.110*
H17C	0.4713	−0.2476	0.2970	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.02768 (17)	0.03613 (19)	0.03235 (17)	0.00497 (12)	−0.00236 (11)	−0.00102 (12)
O1	0.0396 (7)	0.0454 (8)	0.0458 (7)	0.0120 (6)	−0.0079 (5)	−0.0127 (6)
O2	0.0487 (8)	0.0503 (8)	0.0481 (8)	0.0044 (7)	−0.0073 (6)	−0.0160 (7)
O3	0.0343 (7)	0.0413 (7)	0.0453 (7)	0.0066 (6)	−0.0066 (5)	−0.0083 (6)
O4	0.0364 (8)	0.0960 (14)	0.0991 (14)	0.0110 (9)	−0.0166 (8)	−0.0531 (11)
O5	0.0450 (8)	0.0587 (10)	0.0510 (8)	0.0002 (7)	0.0032 (6)	0.0117 (7)
O6	0.0391 (7)	0.0507 (8)	0.0391 (7)	0.0148 (6)	−0.0069 (5)	−0.0039 (6)
N1	0.0296 (7)	0.0363 (8)	0.0319 (7)	0.0023 (6)	−0.0013 (6)	−0.0012 (6)
N2	0.0315 (8)	0.0398 (9)	0.0393 (8)	0.0004 (7)	−0.0037 (6)	−0.0058 (7)
C1	0.0397 (9)	0.0352 (9)	0.0327 (9)	0.0047 (8)	0.0053 (7)	−0.0010 (7)
C2	0.0365 (9)	0.0382 (10)	0.0329 (9)	0.0065 (8)	0.0047 (7)	0.0011 (7)
C3	0.0441 (11)	0.0514 (13)	0.0454 (11)	0.0150 (9)	−0.0011 (9)	−0.0037 (9)
C4	0.0640 (14)	0.0497 (13)	0.0499 (12)	0.0238 (11)	0.0034 (10)	−0.0062 (10)
C5	0.0661 (13)	0.0419 (11)	0.0384 (10)	0.0080 (10)	0.0030 (9)	−0.0084 (9)
C6	0.0464 (11)	0.0398 (10)	0.0319 (9)	0.0032 (8)	0.0024 (7)	−0.0022 (8)
C7	0.0697 (15)	0.0599 (15)	0.0529 (13)	0.0004 (12)	−0.0131 (11)	−0.0198 (11)
C8	0.0298 (8)	0.0419 (10)	0.0376 (9)	0.0043 (8)	−0.0002 (7)	0.0021 (8)
C9	0.0347 (9)	0.0370 (10)	0.0306 (8)	0.0002 (8)	0.0003 (7)	0.0020 (7)
C10	0.0381 (9)	0.0386 (10)	0.0294 (8)	−0.0028 (8)	0.0037 (7)	0.0005 (7)
C11	0.0383 (10)	0.0558 (12)	0.0471 (11)	−0.0018 (9)	0.0030 (8)	−0.0124 (10)
C12	0.0467 (12)	0.0691 (16)	0.0548 (13)	−0.0144 (11)	0.0012 (10)	−0.0193 (11)
C13	0.0692 (15)	0.0495 (13)	0.0442 (11)	−0.0149 (11)	0.0076 (10)	−0.0117 (9)
C14	0.0667 (14)	0.0398 (11)	0.0464 (11)	0.0052 (10)	0.0061 (10)	−0.0048 (9)
C15	0.0467 (11)	0.0382 (10)	0.0376 (10)	0.0027 (8)	0.0008 (8)	0.0014 (8)
C16	0.0608 (15)	0.094 (2)	0.0636 (15)	0.0445 (15)	0.0118 (12)	0.0132 (14)
C17	0.0587 (15)	0.087 (2)	0.0769 (18)	0.0242 (14)	0.0189 (13)	0.0034 (15)

Geometric parameters (Å, º) top

V1—N1	2.1029 (15)	C5—C6	1.382 (3)
V1—O1	1.8325 (14)	C5—H5A	0.9300
V1—O3	1.9453 (14)	C7—H7A	0.9600
V1—O5	1.5762 (15)	C7—H7B	0.9600
V1—O6	1.7423 (13)	C7—H7C	0.9600
O1—C1	1.340 (2)	C8—H8A	0.9300
O2—C6	1.356 (2)	C9—C10	1.464 (3)
O2—C7	1.424 (3)	C10—C15	1.399 (3)
O3—C9	1.303 (2)	C10—C11	1.402 (3)
O4—C11	1.353 (3)	C11—C12	1.391 (3)
O4—H4B	0.8200	C12—C13	1.373 (3)
O6—C16	1.414 (2)	C12—H12A	0.9300
N1—C8	1.293 (2)	C13—C14	1.378 (3)
N1—N2	1.385 (2)	C13—H13A	0.9300
N2—C9	1.307 (2)	C14—C15	1.374 (3)
C1—C2	1.397 (3)	C14—H14A	0.9300
C1—C6	1.411 (3)	C15—H15A	0.9300
C2—C3	1.412 (3)	C16—C17	1.456 (3)
C2—C8	1.427 (3)	C16—H16A	0.9700
C3—C4	1.364 (3)	C16—H16B	0.9700
C3—H3A	0.9300	C17—H17A	0.9600
C4—C5	1.390 (3)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600

O5—V1—O6	108.88 (8)	O2—C7—H7C	109.5
O5—V1—O1	105.89 (9)	H7A—C7—H7C	109.5
O6—V1—O1	99.34 (7)	H7B—C7—H7C	109.5
O5—V1—O3	100.64 (8)	N1—C8—C2	123.93 (16)
O6—V1—O3	88.75 (6)	N1—C8—H8A	118.0
O1—V1—O3	147.85 (6)	C2—C8—H8A	118.0
O5—V1—N1	101.43 (7)	O3—C9—N2	121.40 (17)
O6—V1—N1	147.57 (7)	O3—C9—C10	119.24 (16)
O1—V1—N1	82.81 (6)	N2—C9—C10	119.35 (16)
O3—V1—N1	74.32 (6)	C15—C10—C11	118.54 (18)
C1—O1—V1	135.34 (12)	C15—C10—C9	120.02 (17)
C6—O2—C7	117.11 (17)	C11—C10—C9	121.44 (17)
C9—O3—V1	118.32 (12)	O4—C11—C12	118.07 (19)
C11—O4—H4B	109.5	O4—C11—C10	122.61 (19)
C16—O6—V1	140.40 (14)	C12—C11—C10	119.3 (2)
C8—N1—N2	115.75 (15)	C13—C12—C11	120.8 (2)
C8—N1—V1	128.45 (12)	C13—C12—H12A	119.6
N2—N1—V1	115.61 (11)	C11—C12—H12A	119.6
C9—N2—N1	109.18 (14)	C12—C13—C14	120.3 (2)
O1—C1—C2	121.40 (17)	C12—C13—H13A	119.8
O1—C1—C6	119.24 (17)	C14—C13—H13A	119.8
C2—C1—C6	119.32 (17)	C15—C14—C13	119.7 (2)
C1—C2—C3	119.96 (18)	C15—C14—H14A	120.1
C1—C2—C8	121.00 (17)	C13—C14—H14A	120.1
C3—C2—C8	119.03 (17)	C14—C15—C10	121.2 (2)
C4—C3—C2	119.83 (19)	C14—C15—H15A	119.4
C4—C3—H3A	120.1	C10—C15—H15A	119.4
C2—C3—H3A	120.1	O6—C16—C17	115.4 (2)
C3—C4—C5	120.60 (19)	O6—C16—H16A	108.4
C3—C4—H4A	119.7	C17—C16—H16A	108.4
C5—C4—H4A	119.7	O6—C16—H16B	108.4
C6—C5—C4	120.9 (2)	C17—C16—H16B	108.4
C6—C5—H5A	119.6	H16A—C16—H16B	107.5
C4—C5—H5A	119.6	C16—C17—H17A	109.5
O2—C6—C5	125.51 (18)	C16—C17—H17B	109.5
O2—C6—C1	115.07 (17)	H17A—C17—H17B	109.5
C5—C6—C1	119.41 (18)	C16—C17—H17C	109.5
O2—C7—H7A	109.5	H17A—C17—H17C	109.5
O2—C7—H7B	109.5	H17B—C17—H17C	109.5
H7A—C7—H7B	109.5

O5—V1—O1—C1	68.39 (19)	C7—O2—C6—C5	−1.0 (3)
O6—V1—O1—C1	−178.79 (18)	C7—O2—C6—C1	−179.65 (19)
O3—V1—O1—C1	−76.1 (2)	C4—C5—C6—O2	−179.3 (2)
N1—V1—O1—C1	−31.50 (18)	C4—C5—C6—C1	−0.7 (3)
O5—V1—O3—C9	−89.56 (14)	O1—C1—C6—O2	2.8 (3)
O6—V1—O3—C9	161.46 (13)	C2—C1—C6—O2	−179.60 (17)
O1—V1—O3—C9	55.77 (18)	O1—C1—C6—C5	−175.88 (18)
N1—V1—O3—C9	9.46 (12)	C2—C1—C6—C5	1.7 (3)
O5—V1—O6—C16	−37.9 (3)	N2—N1—C8—C2	178.23 (17)
O1—V1—O6—C16	−148.3 (3)	V1—N1—C8—C2	−6.9 (3)
O3—V1—O6—C16	63.0 (3)	C1—C2—C8—N1	−5.5 (3)
N1—V1—O6—C16	120.4 (3)	C3—C2—C8—N1	175.82 (19)
O5—V1—N1—C8	−85.71 (17)	V1—O3—C9—N2	−9.5 (2)
O6—V1—N1—C8	115.25 (17)	V1—O3—C9—C10	171.59 (12)
O1—V1—N1—C8	19.13 (16)	N1—N2—C9—O3	1.2 (2)
O3—V1—N1—C8	176.30 (17)	N1—N2—C9—C10	−179.87 (15)
O5—V1—N1—N2	89.16 (14)	O3—C9—C10—C15	−3.2 (3)
O6—V1—N1—N2	−69.88 (17)	N2—C9—C10—C15	177.87 (17)
O1—V1—N1—N2	−166.00 (13)	O3—C9—C10—C11	177.21 (17)
O3—V1—N1—N2	−8.83 (11)	N2—C9—C10—C11	−1.8 (3)
C8—N1—N2—C9	−177.68 (16)	C15—C10—C11—O4	−178.9 (2)
V1—N1—N2—C9	6.78 (18)	C9—C10—C11—O4	0.7 (3)
V1—O1—C1—C2	29.7 (3)	C15—C10—C11—C12	1.9 (3)
V1—O1—C1—C6	−152.82 (15)	C9—C10—C11—C12	−178.46 (19)
O1—C1—C2—C3	175.72 (18)	O4—C11—C12—C13	178.7 (2)
C6—C1—C2—C3	−1.8 (3)	C10—C11—C12—C13	−2.0 (4)
O1—C1—C2—C8	−3.0 (3)	C11—C12—C13—C14	0.6 (4)
C6—C1—C2—C8	179.54 (17)	C12—C13—C14—C15	0.9 (3)
C1—C2—C3—C4	0.9 (3)	C13—C14—C15—C10	−0.9 (3)
C8—C2—C3—C4	179.6 (2)	C11—C10—C15—C14	−0.5 (3)
C2—C3—C4—C5	0.1 (3)	C9—C10—C15—C14	179.89 (18)
C3—C4—C5—C6	−0.2 (4)	V1—O6—C16—C17	14.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N2	0.82	1.86	2.581 (2)	147
C8—H8A···O4ⁱ	0.93	2.31	3.236 (2)	177

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[V(C₁₅H₁₂N₂O₄)(C₂H₅O)O]
M_r	396.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.808 (5), 6.606 (2), 16.693 (8)
β (°)	94.107 (16)
V (Å³)	1738.6 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.37 × 0.25 × 0.13

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (TEXRAY; Molecular Structure Corporation, 1999)
T_min, T_max	0.834, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	15371, 3968, 3243
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.08
No. of reflections	3968
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.22

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—N1	2.1029 (15)	V1—O5	1.5762 (15)
V1—O1	1.8325 (14)	V1—O6	1.7423 (13)
V1—O3	1.9453 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N2	0.82	1.86	2.581 (2)	146.8
C8—H8A···O4ⁱ	0.93	2.31	3.236 (2)	176.7

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

The authors are grateful for financial support from the Foundation of Fujian Educational Committee, China (grant No. JB10007).

References

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