(Methano­lato-κO)[N′-(3-meth­oxy-2-oxidobenzyl­idene-κO2)-4-nitro­benzo­hydrazidato-κ2N′,O]oxidovanadium(V)

Wang, C.-Y.; Tu, H.-Y.; Zhu, P.-F.; Sheng, S.-J.

doi:10.1107/S1600536811040207

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1495

doi:10.1107/S1600536811040207

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(Methanolato-κO)[N′-(3-methoxy-2-oxidobenzylidene-κO²)-4-nitrobenzohydrazidato-κ²N′,O]oxidovanadium(V)

Chen-Yi Wang,^a ^* Hai-Yu Tu,^a Pei-Fei Zhu ^a and Su-Jun Sheng ^a

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

(Received 28 September 2011; accepted 29 September 2011; online 5 October 2011)

The title oxidovanadium(V) complex, [V(C₁₅H₁₁N₃O₅)(CH₃O)O], was obtained by the reaction of 2-hydroxy-3-methoxybenzaldehyde, 4-nitrobenzohydrazide and vanadyl sulfate in methanol. The V^V atom is five-coordinated by the two O and one N donor atoms of the Schiff base ligand, one methanolate O atom and one oxido O atom, forming a distorted square-pyramidal geometry.

Related literature

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

Experimental

Crystal data

[V(C₁₅H₁₁N₃O₅)(CH₃O)O]
M_r = 411.24
Triclinic, $[P \overline 1]$
a = 6.410 (3) Å
b = 10.253 (3) Å
c = 13.490 (3) Å
α = 71.111 (2)°
β = 87.998 (2)°
γ = 86.473 (2)°
V = 837.2 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.883, T_max = 0.883
6739 measured reflections
3538 independent reflections
2686 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.115
S = 1.15
3538 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O6	1.566 (2)
V1—O7	1.743 (2)
V1—O1	1.816 (2)
V1—O3	1.922 (2)
V1—N1	2.095 (3)

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/S1600536811040207/qm2033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040207/qm2033Isup2.hkl

checkCIF report

Comment top

As part of our investigations into new Schiff base complexes (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, a new mononuclear oxovanadium(V) complex, Fig. 1. The V atom in the complex is five-coordinated by the NNO donor atoms of the Schiff base ligand, one methoxy O atom, and one oxo O atom, forming a square pyramidal geometry. The V–O and V–N bond lengths (Table 1) are typical and are comparable with those observed in other similar vanadium complexes (Deng et al., 2005; Gao et al., 2005; Huo et al., 2004).

Related literature top

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

Experimental top

2-Hydroxy-3-methoxybenzaldehyde (1.0 mmol, 0.15 g), 4-nitrobenzohydrazide (1.0 mmol, 0.18 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 the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

(Methanolato-κO)[N'-(3-methoxy-2-oxidobenzylidene-κO²)-4-nitrobenzohydrazidato-κ²N',O]oxidovanadium(V) top

Crystal data top

[V(C₁₅H₁₁N₃O₅)(CH₃O)O]	Z = 2
M_r = 411.24	F(000) = 420
Triclinic, P1	D_x = 1.631 Mg m⁻³
a = 6.410 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.253 (3) Å	Cell parameters from 2551 reflections
c = 13.490 (3) Å	θ = 3.0–28.2°
α = 71.111 (2)°	µ = 0.64 mm⁻¹
β = 87.998 (2)°	T = 298 K
γ = 86.473 (2)°	Block, brown
V = 837.2 (5) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3538 independent reflections
Radiation source: fine-focus sealed tube	2686 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.883, T_max = 0.883	k = −13→13
6739 measured reflections	l = −17→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0313P)² + 0.6271P] where P = (F_o² + 2F_c²)/3
3538 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[V(C₁₅H₁₁N₃O₅)(CH₃O)O]	γ = 86.473 (2)°
M_r = 411.24	V = 837.2 (5) Å³
Triclinic, P1	Z = 2
a = 6.410 (3) Å	Mo Kα radiation
b = 10.253 (3) Å	µ = 0.64 mm⁻¹
c = 13.490 (3) Å	T = 298 K
α = 71.111 (2)°	0.20 × 0.20 × 0.20 mm
β = 87.998 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3538 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2686 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.883	R_int = 0.029
6739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.15	Δρ_max = 0.47 e Å⁻³
3538 reflections	Δρ_min = −0.37 e Å⁻³
246 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	0.33384 (8)	0.75890 (6)	0.64666 (4)	0.03741 (18)
N1	0.2573 (4)	0.7590 (2)	0.7989 (2)	0.0367 (6)
N2	0.3794 (4)	0.8370 (3)	0.8399 (2)	0.0400 (6)
N3	1.1433 (5)	1.2126 (3)	0.8496 (3)	0.0533 (8)
O1	0.1727 (3)	0.6105 (2)	0.68310 (17)	0.0450 (6)
O2	−0.0923 (4)	0.4642 (3)	0.62674 (19)	0.0571 (7)
O3	0.5567 (3)	0.8465 (2)	0.68799 (17)	0.0438 (6)
O4	1.1239 (4)	1.2504 (3)	0.9257 (2)	0.0785 (9)
O5	1.2866 (4)	1.2421 (3)	0.7875 (3)	0.0847 (10)
O6	0.1922 (4)	0.8862 (2)	0.58276 (19)	0.0564 (6)
O7	0.5102 (3)	0.7131 (2)	0.56069 (17)	0.0469 (6)
C1	−0.0354 (5)	0.6150 (3)	0.8311 (2)	0.0376 (7)
C2	0.0009 (5)	0.5759 (3)	0.7423 (2)	0.0372 (7)
C3	−0.1420 (5)	0.4947 (3)	0.7153 (3)	0.0413 (8)
C4	−0.3148 (5)	0.4535 (3)	0.7785 (3)	0.0497 (9)
H4	−0.4103	0.4001	0.7610	0.060*
C5	−0.3481 (5)	0.4906 (4)	0.8679 (3)	0.0541 (9)
H5	−0.4649	0.4610	0.9102	0.065*
C6	−0.2115 (5)	0.5703 (3)	0.8950 (3)	0.0480 (9)
H6	−0.2353	0.5947	0.9552	0.058*
C7	−0.2465 (6)	0.4031 (4)	0.5845 (3)	0.0626 (11)
H7A	−0.2655	0.3107	0.6301	0.094*
H7B	−0.2013	0.4008	0.5165	0.094*
H7C	−0.3764	0.4566	0.5787	0.094*
C8	0.1051 (5)	0.7005 (3)	0.8586 (2)	0.0388 (7)
H8	0.0856	0.7146	0.9231	0.047*
C9	0.5315 (5)	0.8793 (3)	0.7736 (2)	0.0370 (7)
C10	0.6881 (4)	0.9669 (3)	0.7941 (2)	0.0364 (7)
C11	0.8536 (5)	1.0068 (3)	0.7247 (3)	0.0452 (8)
H11	0.8644	0.9799	0.6651	0.054*
C12	1.0030 (5)	1.0865 (3)	0.7439 (3)	0.0482 (9)
H12	1.1167	1.1119	0.6984	0.058*
C13	0.9818 (5)	1.1275 (3)	0.8302 (3)	0.0400 (8)
C14	0.8183 (5)	1.0912 (4)	0.8996 (3)	0.0532 (9)
H14	0.8062	1.1209	0.9579	0.064*
C15	0.6721 (5)	1.0095 (4)	0.8809 (3)	0.0522 (9)
H15	0.5607	0.9827	0.9278	0.063*
C16	0.6484 (6)	0.7807 (4)	0.4806 (3)	0.0659 (11)
H16A	0.5745	0.8560	0.4301	0.099*
H16B	0.7069	0.7170	0.4471	0.099*
H16C	0.7586	0.8156	0.5097	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0382 (3)	0.0428 (3)	0.0366 (3)	−0.0148 (2)	0.0045 (2)	−0.0186 (2)
N1	0.0344 (14)	0.0391 (14)	0.0411 (16)	−0.0128 (11)	0.0014 (12)	−0.0175 (12)
N2	0.0377 (14)	0.0468 (15)	0.0426 (16)	−0.0183 (12)	0.0045 (12)	−0.0219 (13)
N3	0.0438 (18)	0.0463 (17)	0.071 (2)	−0.0160 (14)	−0.0103 (16)	−0.0175 (16)
O1	0.0440 (13)	0.0521 (13)	0.0486 (14)	−0.0239 (10)	0.0104 (11)	−0.0271 (11)
O2	0.0540 (15)	0.0696 (16)	0.0620 (17)	−0.0260 (12)	−0.0003 (12)	−0.0370 (14)
O3	0.0393 (12)	0.0557 (14)	0.0466 (14)	−0.0223 (10)	0.0103 (10)	−0.0280 (11)
O4	0.079 (2)	0.095 (2)	0.080 (2)	−0.0395 (17)	−0.0057 (16)	−0.0476 (18)
O5	0.0576 (17)	0.104 (2)	0.107 (2)	−0.0502 (17)	0.0142 (17)	−0.048 (2)
O6	0.0608 (15)	0.0550 (15)	0.0543 (16)	−0.0038 (12)	−0.0042 (12)	−0.0183 (12)
O7	0.0485 (13)	0.0544 (14)	0.0464 (14)	−0.0212 (11)	0.0156 (11)	−0.0264 (11)
C1	0.0349 (17)	0.0403 (17)	0.0357 (18)	−0.0124 (13)	0.0003 (14)	−0.0077 (14)
C2	0.0336 (17)	0.0352 (16)	0.0416 (19)	−0.0111 (13)	−0.0011 (14)	−0.0092 (14)
C3	0.0410 (18)	0.0393 (17)	0.044 (2)	−0.0108 (14)	−0.0085 (15)	−0.0113 (15)
C4	0.0394 (19)	0.049 (2)	0.060 (2)	−0.0207 (15)	−0.0070 (17)	−0.0134 (18)
C5	0.0399 (19)	0.064 (2)	0.057 (2)	−0.0249 (17)	0.0075 (17)	−0.0141 (19)
C6	0.047 (2)	0.057 (2)	0.041 (2)	−0.0201 (16)	0.0067 (16)	−0.0144 (17)
C7	0.066 (2)	0.060 (2)	0.074 (3)	−0.0171 (19)	−0.020 (2)	−0.034 (2)
C8	0.0394 (18)	0.0453 (18)	0.0340 (18)	−0.0129 (14)	0.0038 (14)	−0.0145 (15)
C9	0.0347 (17)	0.0406 (17)	0.0398 (19)	−0.0091 (13)	0.0008 (14)	−0.0174 (15)
C10	0.0338 (16)	0.0357 (16)	0.0429 (19)	−0.0095 (13)	0.0006 (14)	−0.0159 (14)
C11	0.0415 (18)	0.052 (2)	0.050 (2)	−0.0153 (15)	0.0088 (16)	−0.0269 (17)
C12	0.0362 (18)	0.052 (2)	0.058 (2)	−0.0175 (15)	0.0131 (16)	−0.0183 (18)
C13	0.0322 (17)	0.0385 (17)	0.051 (2)	−0.0094 (13)	−0.0069 (15)	−0.0151 (15)
C14	0.054 (2)	0.069 (2)	0.051 (2)	−0.0239 (18)	0.0049 (17)	−0.0351 (19)
C15	0.045 (2)	0.072 (2)	0.051 (2)	−0.0265 (17)	0.0119 (17)	−0.0320 (19)
C16	0.069 (3)	0.069 (3)	0.063 (3)	−0.025 (2)	0.028 (2)	−0.023 (2)

Geometric parameters (Å, º) top

V1—O6	1.566 (2)	C4—H4	0.9300
V1—O7	1.743 (2)	C5—C6	1.368 (4)
V1—O1	1.816 (2)	C5—H5	0.9300
V1—O3	1.922 (2)	C6—H6	0.9300
V1—N1	2.095 (3)	C7—H7A	0.9600
N1—C8	1.290 (4)	C7—H7B	0.9600
N1—N2	1.397 (3)	C7—H7C	0.9600
N2—C9	1.295 (4)	C8—H8	0.9300
N3—O5	1.206 (4)	C9—C10	1.477 (4)
N3—O4	1.209 (4)	C10—C15	1.375 (4)
N3—C13	1.476 (4)	C10—C11	1.380 (4)
O1—C2	1.334 (3)	C11—C12	1.380 (4)
O2—C3	1.353 (4)	C11—H11	0.9300
O2—C7	1.428 (4)	C12—C13	1.360 (4)
O3—C9	1.306 (3)	C12—H12	0.9300
O7—C16	1.398 (4)	C13—C14	1.367 (4)
C1—C2	1.390 (4)	C14—C15	1.376 (4)
C1—C6	1.402 (4)	C14—H14	0.9300
C1—C8	1.431 (4)	C15—H15	0.9300
C2—C3	1.406 (4)	C16—H16A	0.9600
C3—C4	1.375 (4)	C16—H16B	0.9600
C4—C5	1.383 (5)	C16—H16C	0.9600

O6—V1—O7	108.77 (12)	C1—C6—H6	120.3
O6—V1—O1	106.79 (12)	O2—C7—H7A	109.5
O7—V1—O1	99.86 (10)	O2—C7—H7B	109.5
O6—V1—O3	101.83 (11)	H7A—C7—H7B	109.5
O7—V1—O3	88.11 (10)	O2—C7—H7C	109.5
O1—V1—O3	145.77 (10)	H7A—C7—H7C	109.5
O6—V1—N1	99.57 (12)	H7B—C7—H7C	109.5
O7—V1—N1	149.12 (11)	N1—C8—C1	123.6 (3)
O1—V1—N1	82.96 (9)	N1—C8—H8	118.2
O3—V1—N1	74.03 (9)	C1—C8—H8	118.2
C8—N1—N2	115.3 (2)	N2—C9—O3	122.9 (3)
C8—N1—V1	128.1 (2)	N2—C9—C10	120.1 (3)
N2—N1—V1	116.50 (18)	O3—C9—C10	117.0 (3)
C9—N2—N1	106.9 (2)	C15—C10—C11	119.4 (3)
O5—N3—O4	123.5 (3)	C15—C10—C9	121.3 (3)
O5—N3—C13	117.9 (3)	C11—C10—C9	119.3 (3)
O4—N3—C13	118.6 (3)	C12—C11—C10	119.9 (3)
C2—O1—V1	134.51 (19)	C12—C11—H11	120.1
C3—O2—C7	117.9 (3)	C10—C11—H11	120.1
C9—O3—V1	118.25 (18)	C13—C12—C11	119.2 (3)
C16—O7—V1	136.8 (2)	C13—C12—H12	120.4
C2—C1—C6	119.8 (3)	C11—C12—H12	120.4
C2—C1—C8	120.8 (3)	C12—C13—C14	122.2 (3)
C6—C1—C8	119.3 (3)	C12—C13—N3	118.4 (3)
O1—C2—C1	121.3 (2)	C14—C13—N3	119.3 (3)
O1—C2—C3	118.9 (3)	C13—C14—C15	118.2 (3)
C1—C2—C3	119.8 (3)	C13—C14—H14	120.9
O2—C3—C4	126.0 (3)	C15—C14—H14	120.9
O2—C3—C2	114.8 (3)	C10—C15—C14	121.0 (3)
C4—C3—C2	119.2 (3)	C10—C15—H15	119.5
C3—C4—C5	120.7 (3)	C14—C15—H15	119.5
C3—C4—H4	119.7	O7—C16—H16A	109.5
C5—C4—H4	119.7	O7—C16—H16B	109.5
C6—C5—C4	120.9 (3)	H16A—C16—H16B	109.5
C6—C5—H5	119.5	O7—C16—H16C	109.5
C4—C5—H5	119.5	H16A—C16—H16C	109.5
C5—C6—C1	119.5 (3)	H16B—C16—H16C	109.5
C5—C6—H6	120.3

Experimental details

Crystal data
Chemical formula	[V(C₁₅H₁₁N₃O₅)(CH₃O)O]
M_r	411.24
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.410 (3), 10.253 (3), 13.490 (3)
α, β, γ (°)	71.111 (2), 87.998 (2), 86.473 (2)
V (Å³)	837.2 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.883, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	6739, 3538, 2686
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.115, 1.15
No. of reflections	3538
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.37

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

Selected bond lengths (Å) top

V1—O6	1.566 (2)	V1—O3	1.922 (2)
V1—O7	1.743 (2)	V1—N1	2.095 (3)
V1—O1	1.816 (2)

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Applied Research Project on Nonprofit Technology 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 (Nos. 2010R42525 and 2011R425027).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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