[N′-(3-Eth­oxy-2-oxidobenzyl­idene-κO2)-4-methyl­benzohydrazidato-κ2O,N′](methano­lato-κO)oxidovanadium(V)

Wang, C.-Y.; Wu, X.; Cao, F.; Yuan, C.-J.

doi:10.1107/S1600536811041547

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1538

doi:10.1107/S1600536811041547

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[N′-(3-Ethoxy-2-oxidobenzylidene-κO²)-4-methylbenzohydrazidato-κ²O,N′](methanolato-κO)oxidovanadium(V)

Chen-Yi Wang,^a ^* Xiang Wu,^a Feng Cao ^a and Cai-Jun Yuan ^a

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 8 October 2011; accepted 10 October 2011; online 12 October 2011)

The title oxidovanadium(V) complex, [V(C₁₇H₁₆N₂O₃)(CH₃O)O], was obtained by the reaction of 3-ethoxy-2-hydroxybenzaldehyde, 4-methylbenzohydrazide and vanadyl sulfate in methanol. The V^V atom is coordinated by the O,N,O′-tridentate Schiff base ligand, one methanolate O atom and one oxide O atom, forming a distorted VO₄N square-pyramidal coordination geometry. The oxide O atom lies at the apex of the square pyramid and the N atom of the ligand and the methanolate O atom are trans. The dihedral angle between the benzene rings of the ligand is 1.8 (3)°.

Related literature

For background to Schiff base complexes, see: Wang (2009 ); Wang & Ye (2011 ). For similar vanadium(V) complexes, see: Wang et al. (2011 ); Deng et al. (2005 ); Gao et al. (2005 ); Huo et al. (2004 ).

Experimental

Crystal data

[V(C₁₇H₁₆N₂O₃)(CH₃O)O]
M_r = 394.29
Monoclinic, P 2₁ /c
a = 7.6954 (16) Å
b = 28.345 (3) Å
c = 8.3877 (18) Å
β = 105.175 (2)°
V = 1765.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.842, T_max = 0.856
14022 measured reflections
4044 independent reflections
2986 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.110
S = 1.05
4044 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O5	1.5813 (17)
V1—O4	1.7499 (17)
V1—O1	1.8326 (16)
V1—O3	1.9170 (16)
V1—N1	2.1031 (19)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041547/hb6443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041547/hb6443Isup2.hkl

checkCIF report

Comment top

As part of our investigations into new Schiff base complexes and urease inhibition (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, (I), a new mononuclear oxovanadium(V) complex, Fig. 1. The V atom in the complex is five-coordinated by the O,N,O-tridentate Schiff base ligand, one methanolate O atom, and one oxide O atom, forming a distorted square-pyramidal geometry. The oxide O atom lies on the apical position of the square-pyramidal geometry. The dihedral angle between the two benzene rings is 1.8 (3)°. The V–O and V–N bond lengths (Table 1) are typical and are comparable with those observed in other similar vanadium complexes (Wang et al., 2011; Deng et al., 2005; Gao et al., 2005; Huo et al., 2004).

Related literature top

For background to Schiff base complexes, see: Wang (2009); Wang & Ye (2011). For similar vanadium(V) complexes, see: Wang et al. (2011); Deng et al. (2005); Gao et al. (2005); Huo et al. (2004).

Experimental top

3-Ethoxy-2-hydroxybenzaldehyde (1.0 mmol, 0.17 g), 4-methylbenzohydrazide (1.0 mmol, 0.15 g), and vanadyl sulfate (1.0 mmol, 0.16 g) were dissolved in methanol (30 ml). The mixture was stirred at room temperature for 10 min to give a clear brown solution. After keeping the solution in air for a week, brown block-shaped crystals were formed at the bottom of the vessel.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.

[N'-(3-Ethoxy-2-oxidobenzylidene-κO²)-4- methylbenzohydrazidato-κ²O,N'](methanolato- κO)oxidovanadium(V) top

Crystal data top

[V(C₁₇H₁₆N₂O₃)(CH₃O)O]	F(000) = 816
M_r = 394.29	D_x = 1.483 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3023 reflections
a = 7.6954 (16) Å	θ = 2.6–25.0°
b = 28.345 (3) Å	µ = 0.59 mm⁻¹
c = 8.3877 (18) Å	T = 298 K
β = 105.175 (2)°	Block, brown
V = 1765.8 (6) Å³	0.30 × 0.27 × 0.27 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4044 independent reflections
Radiation source: fine-focus sealed tube	2986 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.842, T_max = 0.856	k = −36→35
14022 measured reflections	l = −10→10

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0473P)² + 0.4204P] where P = (F_o² + 2F_c²)/3
4044 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[V(C₁₇H₁₆N₂O₃)(CH₃O)O]	V = 1765.8 (6) Å³
M_r = 394.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6954 (16) Å	µ = 0.59 mm⁻¹
b = 28.345 (3) Å	T = 298 K
c = 8.3877 (18) Å	0.30 × 0.27 × 0.27 mm
β = 105.175 (2)°

Data collection top

Bruker SMART CCD diffractometer	4044 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2986 reflections with I > 2σ(I)
T_min = 0.842, T_max = 0.856	R_int = 0.039
14022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.05	Δρ_max = 0.27 e Å⁻³
4044 reflections	Δρ_min = −0.30 e Å⁻³
238 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	0.23672 (5)	0.414915 (13)	0.47578 (5)	0.03413 (14)
N1	0.1850 (2)	0.34208 (6)	0.4771 (2)	0.0333 (4)
N2	0.0915 (3)	0.32243 (7)	0.3264 (2)	0.0386 (5)
O1	0.3948 (2)	0.40199 (5)	0.67570 (19)	0.0407 (4)
O2	0.5797 (2)	0.42530 (6)	0.9805 (2)	0.0477 (5)
O3	0.1583 (2)	0.39594 (6)	0.24884 (19)	0.0411 (4)
O4	0.3495 (2)	0.46251 (6)	0.4152 (2)	0.0478 (4)
O5	0.0567 (2)	0.43456 (6)	0.5082 (2)	0.0479 (4)
C1	0.3177 (3)	0.32665 (8)	0.7653 (3)	0.0342 (5)
C2	0.4022 (3)	0.37085 (8)	0.7972 (3)	0.0340 (5)
C3	0.5005 (3)	0.38212 (9)	0.9597 (3)	0.0386 (6)
C4	0.5096 (3)	0.34910 (10)	1.0833 (3)	0.0466 (6)
H4	0.5724	0.3564	1.1910	0.056*
C5	0.4279 (3)	0.30551 (10)	1.0504 (3)	0.0498 (7)
H5	0.4376	0.2839	1.1358	0.060*
C6	0.3330 (3)	0.29378 (9)	0.8939 (3)	0.0422 (6)
H6	0.2789	0.2643	0.8726	0.051*
C7	0.2177 (3)	0.31382 (8)	0.6028 (3)	0.0350 (5)
H7	0.1731	0.2832	0.5860	0.042*
C8	0.0825 (3)	0.35451 (8)	0.2130 (3)	0.0336 (5)
C9	−0.0137 (3)	0.34495 (8)	0.0398 (3)	0.0324 (5)
C10	−0.0244 (3)	0.37956 (9)	−0.0791 (3)	0.0411 (6)
H10	0.0317	0.4085	−0.0499	0.049*
C11	−0.1182 (3)	0.37113 (9)	−0.2405 (3)	0.0449 (6)
H11	−0.1248	0.3947	−0.3188	0.054*
C12	−0.2024 (3)	0.32857 (9)	−0.2889 (3)	0.0388 (6)
C13	−0.1894 (3)	0.29402 (9)	−0.1695 (3)	0.0439 (6)
H13	−0.2440	0.2649	−0.1994	0.053*
C14	−0.0972 (3)	0.30194 (8)	−0.0072 (3)	0.0393 (6)
H14	−0.0911	0.2783	0.0710	0.047*
C15	−0.3043 (4)	0.32044 (11)	−0.4656 (3)	0.0559 (7)
H15A	−0.3865	0.3461	−0.5028	0.084*
H15B	−0.3704	0.2914	−0.4740	0.084*
H15C	−0.2212	0.3186	−0.5331	0.084*
C16	0.6757 (4)	0.43846 (10)	1.1461 (3)	0.0546 (7)
H16A	0.7681	0.4153	1.1917	0.065*
H16B	0.5935	0.4399	1.2161	0.065*
C17	0.7590 (4)	0.48552 (11)	1.1390 (4)	0.0727 (10)
H17A	0.8465	0.4833	1.0761	0.109*
H17B	0.8169	0.4959	1.2490	0.109*
H17C	0.6674	0.5078	1.0873	0.109*
C18	0.2882 (4)	0.50506 (11)	0.3339 (4)	0.0795 (11)
H18A	0.1982	0.4985	0.2333	0.119*
H18B	0.3873	0.5213	0.3090	0.119*
H18C	0.2373	0.5244	0.4040	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0416 (2)	0.0292 (2)	0.0292 (2)	−0.00241 (17)	0.00511 (16)	0.00033 (17)
N1	0.0382 (10)	0.0303 (10)	0.0294 (10)	−0.0005 (8)	0.0050 (8)	−0.0002 (8)
N2	0.0492 (12)	0.0339 (11)	0.0280 (10)	−0.0048 (9)	0.0018 (8)	−0.0042 (8)
O1	0.0486 (10)	0.0349 (9)	0.0324 (9)	−0.0063 (7)	−0.0004 (7)	0.0007 (7)
O2	0.0515 (10)	0.0465 (11)	0.0352 (10)	0.0005 (8)	−0.0063 (8)	−0.0065 (8)
O3	0.0569 (10)	0.0346 (9)	0.0302 (9)	−0.0100 (8)	0.0086 (7)	−0.0009 (7)
O4	0.0544 (10)	0.0414 (10)	0.0427 (10)	−0.0136 (8)	0.0042 (8)	0.0062 (8)
O5	0.0524 (10)	0.0444 (10)	0.0480 (11)	0.0074 (8)	0.0151 (8)	0.0006 (8)
C1	0.0334 (11)	0.0370 (13)	0.0315 (12)	0.0051 (10)	0.0071 (9)	0.0009 (10)
C2	0.0355 (12)	0.0344 (12)	0.0304 (12)	0.0080 (10)	0.0057 (9)	0.0025 (10)
C3	0.0381 (12)	0.0412 (14)	0.0339 (13)	0.0079 (10)	0.0049 (10)	−0.0038 (10)
C4	0.0488 (14)	0.0608 (18)	0.0259 (13)	0.0095 (13)	0.0021 (10)	0.0025 (12)
C5	0.0573 (16)	0.0549 (17)	0.0357 (14)	0.0058 (13)	0.0093 (12)	0.0144 (13)
C6	0.0450 (13)	0.0436 (15)	0.0381 (14)	0.0015 (11)	0.0110 (11)	0.0085 (11)
C7	0.0397 (12)	0.0291 (12)	0.0353 (13)	−0.0004 (9)	0.0084 (10)	0.0010 (10)
C8	0.0378 (12)	0.0325 (12)	0.0309 (12)	−0.0002 (10)	0.0094 (9)	−0.0009 (10)
C9	0.0358 (12)	0.0339 (12)	0.0277 (12)	0.0035 (9)	0.0086 (9)	−0.0019 (10)
C10	0.0516 (14)	0.0368 (14)	0.0353 (13)	−0.0018 (11)	0.0124 (11)	−0.0004 (11)
C11	0.0546 (15)	0.0486 (15)	0.0337 (14)	0.0082 (12)	0.0157 (11)	0.0093 (12)
C12	0.0367 (12)	0.0491 (15)	0.0304 (13)	0.0055 (11)	0.0083 (10)	−0.0018 (11)
C13	0.0478 (14)	0.0448 (15)	0.0359 (14)	−0.0070 (11)	0.0054 (11)	−0.0056 (11)
C14	0.0466 (13)	0.0382 (14)	0.0306 (13)	−0.0010 (11)	0.0058 (10)	0.0024 (10)
C15	0.0592 (16)	0.071 (2)	0.0323 (14)	0.0095 (15)	0.0031 (12)	−0.0006 (14)
C16	0.0515 (15)	0.0630 (18)	0.0385 (15)	0.0086 (14)	−0.0072 (12)	−0.0153 (13)
C17	0.071 (2)	0.062 (2)	0.067 (2)	−0.0001 (16)	−0.0148 (16)	−0.0230 (17)
C18	0.069 (2)	0.062 (2)	0.092 (3)	−0.0136 (16)	−0.0071 (18)	0.0393 (18)

Geometric parameters (Å, º) top

V1—O5	1.5813 (17)	C8—C9	1.473 (3)
V1—O4	1.7499 (17)	C9—C10	1.386 (3)
V1—O1	1.8326 (16)	C9—C14	1.386 (3)
V1—O3	1.9170 (16)	C10—C11	1.378 (3)
V1—N1	2.1031 (19)	C10—H10	0.9300
N1—C7	1.295 (3)	C11—C12	1.380 (3)
N1—N2	1.396 (2)	C11—H11	0.9300
N2—C8	1.305 (3)	C12—C13	1.385 (3)
O1—C2	1.338 (3)	C12—C15	1.502 (3)
O2—C3	1.358 (3)	C13—C14	1.379 (3)
O2—C16	1.441 (3)	C13—H13	0.9300
O3—C8	1.311 (3)	C14—H14	0.9300
O4—C18	1.405 (3)	C15—H15A	0.9600
C1—C2	1.405 (3)	C15—H15B	0.9600
C1—C6	1.407 (3)	C15—H15C	0.9600
C1—C7	1.426 (3)	C16—C17	1.488 (4)
C2—C3	1.412 (3)	C16—H16A	0.9700
C3—C4	1.384 (3)	C16—H16B	0.9700
C4—C5	1.381 (4)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.366 (3)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—H7	0.9300	C18—H18C	0.9600

O5—V1—O4	107.58 (9)	C10—C9—C14	118.8 (2)
O5—V1—O1	108.34 (9)	C10—C9—C8	120.0 (2)
O4—V1—O1	99.14 (8)	C14—C9—C8	121.2 (2)
O5—V1—O3	101.98 (8)	C11—C10—C9	120.1 (2)
O4—V1—O3	88.79 (7)	C11—C10—H10	119.9
O1—V1—O3	144.43 (8)	C9—C10—H10	119.9
O5—V1—N1	99.74 (8)	C10—C11—C12	121.7 (2)
O4—V1—N1	150.14 (8)	C10—C11—H11	119.1
O1—V1—N1	83.11 (7)	C12—C11—H11	119.1
O3—V1—N1	73.70 (7)	C11—C12—C13	117.8 (2)
C7—N1—N2	115.75 (19)	C11—C12—C15	120.6 (2)
C7—N1—V1	127.94 (16)	C13—C12—C15	121.7 (2)
N2—N1—V1	116.11 (13)	C14—C13—C12	121.3 (2)
C8—N2—N1	107.35 (18)	C14—C13—H13	119.3
C2—O1—V1	135.60 (15)	C12—C13—H13	119.3
C3—O2—C16	117.1 (2)	C13—C14—C9	120.3 (2)
C8—O3—V1	118.96 (14)	C13—C14—H14	119.8
C18—O4—V1	132.35 (17)	C9—C14—H14	119.8
C2—C1—C6	120.2 (2)	C12—C15—H15A	109.5
C2—C1—C7	121.1 (2)	C12—C15—H15B	109.5
C6—C1—C7	118.7 (2)	H15A—C15—H15B	109.5
O1—C2—C1	121.2 (2)	C12—C15—H15C	109.5
O1—C2—C3	119.4 (2)	H15A—C15—H15C	109.5
C1—C2—C3	119.4 (2)	H15B—C15—H15C	109.5
O2—C3—C4	125.5 (2)	O2—C16—C17	108.1 (2)
O2—C3—C2	115.9 (2)	O2—C16—H16A	110.1
C4—C3—C2	118.6 (2)	C17—C16—H16A	110.1
C5—C4—C3	121.6 (2)	O2—C16—H16B	110.1
C5—C4—H4	119.2	C17—C16—H16B	110.1
C3—C4—H4	119.2	H16A—C16—H16B	108.4
C6—C5—C4	120.7 (2)	C16—C17—H17A	109.5
C6—C5—H5	119.6	C16—C17—H17B	109.5
C4—C5—H5	119.6	H17A—C17—H17B	109.5
C5—C6—C1	119.5 (2)	C16—C17—H17C	109.5
C5—C6—H6	120.3	H17A—C17—H17C	109.5
C1—C6—H6	120.3	H17B—C17—H17C	109.5
N1—C7—C1	124.2 (2)	O4—C18—H18A	109.5
N1—C7—H7	117.9	O4—C18—H18B	109.5
C1—C7—H7	117.9	H18A—C18—H18B	109.5
N2—C8—O3	121.5 (2)	O4—C18—H18C	109.5
N2—C8—C9	120.5 (2)	H18A—C18—H18C	109.5
O3—C8—C9	118.0 (2)	H18B—C18—H18C	109.5

Experimental details

Crystal data
Chemical formula	[V(C₁₇H₁₆N₂O₃)(CH₃O)O]
M_r	394.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.6954 (16), 28.345 (3), 8.3877 (18)
β (°)	105.175 (2)
V (Å³)	1765.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.30 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.842, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	14022, 4044, 2986
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.110, 1.05
No. of reflections	4044
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

V1—O5	1.5813 (17)	V1—O3	1.9170 (16)
V1—O4	1.7499 (17)	V1—N1	2.1031 (19)
V1—O1	1.8326 (16)

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Applied Research Project on Nonprofit Tchnology of Zhejiang Province (No. 2010 C32060), the Zhejiang Provincial Natural Science Foundation of China (No. Y407318), and the Technological Innovation Project (sinfonietta talent plan) of College Students in Zhejiang Province (No. 2010R42525 & No. 2011R425027).

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