Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Oct 12;67(Pt 11):m1538. doi: 10.1107/S1600536811041547

[N′-(3-Eth­oxy-2-oxidobenzyl­idene-κO 2)-4-methyl­benzohydrazidato-κ2 O,N′](methano­lato-κO)oxidovanadium(V)

Chen-Yi Wang a,*, Xiang Wu a, Feng Cao a, Cai-Jun Yuan a
PMCID: PMC3246962  PMID: 22219782

Abstract

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 VV 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 ▶).graphic file with name e-67-m1538-scheme1.jpg

Experimental

Crystal data

  • [V(C17H16N2O3)(CH3O)O]

  • M r = 394.29

  • Monoclinic, Inline graphic

  • 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[F 2 > 2σ(F 2)] = 0.045

  • wR(F 2) = 0.110

  • S = 1.05

  • 4044 reflections

  • 238 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.30 e Å−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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041547/hb6443sup1.cif

e-67-m1538-sup1.cif (18KB, cif)

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

e-67-m1538-Isup2.hkl (198.2KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)
Open in a new tab

Acknowledgments

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).

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

Hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with Uiso(H) set at 1.2 or 1.5Ueq(C).

Figures

Fig. 1.

Fig. 1.

Open in a new tab

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

Crystal data

[V(C17H16N2O3)(CH3O)O] F(000) = 816
Mr = 394.29 Dx = 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
Open in a new tab

Data collection

Bruker SMART CCD diffractometer 4044 independent reflections
Radiation source: fine-focus sealed tube 2986 reflections with I > 2σ(I)
graphite Rint = 0.039
ω scans θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −9→9
Tmin = 0.842, Tmax = 0.856 k = −36→35
14022 measured reflections l = −10→10
Open in a new tab

Refinement

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(Fo2) + (0.0473P)2 + 0.4204P] where P = (Fo2 + 2Fc2)/3
4044 reflections (Δ/σ)max = 0.001
238 parameters Δρmax = 0.27 e Å−3
0 restraints Δρmin = −0.30 e Å−3
Open in a new tab

Special details

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.
Open in a new tab

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

x y z Uiso*/Ueq
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*
Open in a new tab

Atomic displacement parameters (Å2)

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)
Open in a new tab

Geometric parameters (Å, °)

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
Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6443).

References

  1. Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  2. Deng, Z.-P., Gao, S., Huo, L.-H. & Zhao, H. (2005). Acta Cryst. E61, m2214–m2216. [DOI] [PubMed]
  3. Gao, S., Huo, L.-H., Deng, Z.-P. & Zhao, H. (2005). Acta Cryst. E61, m978–m980. [DOI] [PubMed]
  4. Huo, L.-H., Gao, S., Liu, J.-W., Zhao, H. & Ng, S. W. (2004). Acta Cryst. E60, m606–m608.
  5. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Wang, C.-Y. (2009). J. Coord. Chem. 62, 2860–2868.
  8. Wang, C.-Y., Hu, J.-J., Tu, H.-Y., Zhu, P.-F. & Sheng, S.-J. (2011). Acta Cryst. E67, m1475–m1476. [DOI] [PMC free article] [PubMed]
  9. Wang, C. Y. & Ye, J. Y. (2011). Russ. J. Coord. Chem. 37, 235–241.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041547/hb6443sup1.cif

e-67-m1538-sup1.cif (18KB, cif)

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

e-67-m1538-Isup2.hkl (198.2KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES