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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): m422.
Published online 2009 March 25. doi:  10.1107/S1600536809009520
PMCID: PMC2968822

(Benzohydrazidato-κ2 N′,O)­[2-(benzoyl­hydrazono-κ2 N,O)propion­ato-κO]oxido­vanadium(V)

Abstract

The VV atom in the title compound, [VO(C7H7N2O)(C10H8N2O3)], is N,O-chelated by the benzohydrazidate anion and O,N,O′-chelated by the 2-(benzoyl­hydrazono)propionate dianion. The distorted octa­hedral trans-N2O4 coordination geometry is completed by the vandadyl O atom. Mol­ecules are linked by N—H(...)O hydrogen bonds into a supra­molecular chain structure parallel to [010].

Related literature

For other benzoyl­hydrazido–oxovanadium compounds, see: Kopka & Mattes (1995 [triangle]); Sundheim et al. (1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m422-scheme1.jpg

Experimental

Crystal data

  • [V(C7H7N2O)(C10H8N2O3)O]
  • M r = 406.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m422-efi1.jpg
  • a = 10.9424 (2) Å
  • b = 6.2384 (1) Å
  • c = 25.7215 (5) Å
  • β = 96.603 (1)°
  • V = 1744.18 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.61 mm−1
  • T = 123 K
  • 0.35 × 0.10 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.816, T max = 0.982
  • 11614 measured reflections
  • 4010 independent reflections
  • 3330 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.091
  • S = 1.00
  • 4010 reflections
  • 253 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009520/tk2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009520/tk2396Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (grant Nos. FS339/2008 A and PS206/2008 A) for supporting this study.

supplementary crystallographic information

Experimental

2-[Benzoylhydrazono]propionic acid (0.66 g, 3.2 mmol), prepared from the condensation reaction of benzhydrazide and pyruvic acid, was dissolved in of ethanol (50 ml). It was then mixed with vanadyl sulfate (0.26 g, 1.6 mmol) in distilled water (20 ml) and the mixture was heated for 5 h. Upon slow evaporation of the filtrate, red crystals formed.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2-1.5U(C).

The nitrogen-bound H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±0.01 Å; their Uiso values were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of VO(C7H7N2O)(C10H8N2O3) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[V(C7H7N2O)(C10H8N2O3)O]F(000) = 832
Mr = 406.27Dx = 1.547 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3550 reflections
a = 10.9424 (2) Åθ = 2.9–28.0°
b = 6.2384 (1) ŵ = 0.61 mm1
c = 25.7215 (5) ÅT = 123 K
β = 96.603 (1)°Prism, red
V = 1744.18 (5) Å30.35 × 0.10 × 0.03 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer4010 independent reflections
Radiation source: fine-focus sealed tube3330 reflections with I > 2σ(I)
graphiteRint = 0.027
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.816, Tmax = 0.982k = −8→7
11614 measured reflectionsl = −32→33

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0443P)2 + 0.9013P] where P = (Fo2 + 2Fc2)/3
4010 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.39 e Å3
2 restraintsΔρmin = −0.38 e Å3

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

xyzUiso*/Ueq
V10.63939 (3)0.51362 (5)0.667678 (11)0.02025 (10)
O10.71456 (13)0.3013 (2)0.65899 (5)0.0310 (3)
O20.47660 (11)0.4125 (2)0.63552 (5)0.0252 (3)
O30.77761 (11)0.7223 (2)0.66978 (4)0.0227 (3)
O40.87206 (11)0.9694 (2)0.62563 (5)0.0250 (3)
O50.53800 (11)0.7850 (2)0.69541 (4)0.0229 (3)
N10.49712 (13)0.6388 (3)0.56603 (5)0.0230 (3)
N20.60460 (13)0.6815 (2)0.59808 (5)0.0200 (3)
N30.57784 (13)0.6090 (2)0.76970 (5)0.0204 (3)
H30.582 (2)0.584 (4)0.8033 (4)0.039 (6)*
N40.63345 (14)0.4678 (2)0.73974 (6)0.0213 (3)
H40.6650 (17)0.363 (3)0.7597 (7)0.029 (6)*
C10.32064 (16)0.4069 (3)0.56296 (7)0.0235 (4)
C20.26918 (17)0.4956 (3)0.51595 (7)0.0271 (4)
H20.31010.60960.50060.033*
C30.15882 (18)0.4191 (3)0.49134 (8)0.0316 (4)
H3A0.12420.48050.45920.038*
C40.09839 (18)0.2527 (3)0.51358 (8)0.0346 (5)
H4A0.02210.20110.49680.041*
C50.14961 (19)0.1621 (4)0.56019 (8)0.0366 (5)
H50.10860.04770.57540.044*
C60.26067 (19)0.2380 (3)0.58478 (8)0.0330 (5)
H60.29590.17470.61660.040*
C70.43810 (16)0.4902 (3)0.58978 (7)0.0221 (4)
C80.67646 (16)0.8356 (3)0.58852 (7)0.0217 (4)
C90.78589 (16)0.8481 (3)0.62982 (6)0.0212 (4)
C100.65613 (17)0.9934 (3)0.54563 (7)0.0273 (4)
H10A0.61740.92230.51390.041*
H10B0.73521.05460.53880.041*
H10C0.60221.10800.55570.041*
C110.52823 (15)0.7794 (3)0.74341 (6)0.0191 (3)
C120.46480 (15)0.9478 (3)0.77016 (7)0.0207 (4)
C130.41422 (15)1.1174 (3)0.73968 (7)0.0235 (4)
H130.42411.12370.70350.028*
C140.34966 (17)1.2765 (3)0.76211 (8)0.0297 (4)
H140.31421.39130.74130.036*
C150.33666 (18)1.2683 (3)0.81518 (8)0.0341 (5)
H150.29141.37660.83050.041*
C160.38955 (18)1.1029 (4)0.84576 (8)0.0335 (5)
H160.38211.10020.88220.040*
C170.45334 (17)0.9412 (3)0.82367 (7)0.0275 (4)
H170.48890.82700.84470.033*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
V10.02461 (16)0.02017 (17)0.01501 (15)0.00332 (12)−0.00179 (11)−0.00063 (11)
O10.0386 (8)0.0277 (7)0.0250 (7)0.0083 (6)−0.0030 (6)−0.0049 (6)
O20.0300 (7)0.0264 (7)0.0178 (6)−0.0041 (6)−0.0026 (5)0.0027 (5)
O30.0242 (6)0.0258 (7)0.0172 (6)0.0014 (5)−0.0019 (5)−0.0025 (5)
O40.0224 (6)0.0308 (7)0.0215 (6)−0.0022 (5)0.0014 (5)−0.0059 (5)
O50.0279 (6)0.0242 (7)0.0165 (6)0.0053 (5)0.0026 (5)0.0028 (5)
N10.0215 (7)0.0289 (8)0.0172 (7)−0.0031 (6)−0.0030 (6)0.0004 (6)
N20.0206 (7)0.0252 (8)0.0137 (6)0.0013 (6)−0.0007 (5)−0.0025 (6)
N30.0226 (7)0.0220 (8)0.0160 (7)0.0002 (6)0.0002 (6)0.0015 (6)
N40.0241 (7)0.0199 (8)0.0190 (7)0.0034 (6)−0.0016 (6)0.0014 (6)
C10.0243 (9)0.0263 (9)0.0196 (8)−0.0021 (7)0.0010 (7)−0.0026 (7)
C20.0265 (9)0.0267 (10)0.0273 (9)−0.0012 (8)−0.0003 (7)0.0026 (8)
C30.0283 (10)0.0350 (11)0.0292 (10)0.0044 (9)−0.0060 (8)−0.0004 (9)
C40.0261 (10)0.0374 (12)0.0386 (11)−0.0060 (9)−0.0035 (8)−0.0076 (9)
C50.0387 (11)0.0377 (12)0.0330 (11)−0.0150 (10)0.0019 (9)−0.0001 (9)
C60.0381 (11)0.0372 (12)0.0224 (9)−0.0108 (9)−0.0021 (8)0.0017 (8)
C70.0256 (9)0.0230 (9)0.0173 (8)0.0005 (7)0.0007 (7)−0.0019 (7)
C80.0229 (8)0.0244 (9)0.0176 (8)0.0020 (7)0.0016 (7)−0.0030 (7)
C90.0222 (8)0.0236 (9)0.0176 (8)0.0049 (7)0.0009 (6)−0.0065 (7)
C100.0277 (9)0.0282 (10)0.0249 (9)−0.0042 (8)−0.0024 (7)0.0036 (8)
C110.0180 (8)0.0206 (8)0.0180 (8)−0.0017 (7)−0.0004 (6)0.0006 (7)
C120.0154 (8)0.0232 (9)0.0236 (9)−0.0025 (7)0.0036 (6)−0.0017 (7)
C130.0186 (8)0.0254 (9)0.0266 (9)−0.0025 (7)0.0027 (7)0.0008 (7)
C140.0227 (9)0.0252 (10)0.0408 (11)0.0006 (8)0.0023 (8)0.0005 (8)
C150.0262 (10)0.0337 (11)0.0436 (12)0.0012 (8)0.0095 (9)−0.0120 (9)
C160.0339 (10)0.0403 (12)0.0280 (10)−0.0011 (9)0.0109 (8)−0.0078 (9)
C170.0267 (9)0.0329 (10)0.0235 (9)0.0014 (8)0.0053 (7)−0.0009 (8)

Geometric parameters (Å, °)

V1—O11.589 (1)C3—H3A0.9500
V1—O21.979 (1)C4—C51.384 (3)
V1—O31.992 (1)C4—H4A0.9500
V1—O52.188 (1)C5—C61.387 (3)
V1—N22.071 (1)C5—H50.9500
V1—N41.884 (2)C6—H60.9500
O2—C71.297 (2)C8—C101.476 (3)
O3—C91.304 (2)C8—C91.509 (2)
O4—C91.223 (2)C10—H10A0.9800
O5—C111.252 (2)C10—H10B0.9800
N1—C71.319 (2)C10—H10C0.9800
N1—N21.382 (2)C11—C121.473 (2)
N2—C81.283 (2)C12—C131.393 (3)
N3—C111.341 (2)C12—C171.397 (2)
N3—N41.359 (2)C13—C141.382 (3)
N3—H30.874 (9)C13—H130.9500
N4—H40.879 (9)C14—C151.389 (3)
C1—C21.389 (3)C14—H140.9500
C1—C61.393 (3)C15—C161.383 (3)
C1—C71.481 (2)C15—H150.9500
C2—C31.382 (3)C16—C171.385 (3)
C2—H20.9500C16—H160.9500
C3—C41.389 (3)C17—H170.9500
O1—V1—N495.10 (7)C4—C5—H5120.0
O1—V1—O297.53 (7)C6—C5—H5120.0
N4—V1—O2103.39 (6)C5—C6—C1120.22 (19)
O1—V1—O398.34 (7)C5—C6—H6119.9
N4—V1—O3100.63 (6)C1—C6—H6119.9
O2—V1—O3149.76 (5)O2—C7—N1123.88 (16)
O1—V1—N2110.29 (6)O2—C7—C1117.71 (16)
N4—V1—N2154.60 (6)N1—C7—C1118.41 (15)
O2—V1—N274.50 (5)N2—C8—C10126.85 (16)
O3—V1—N275.90 (5)N2—C8—C9110.97 (15)
O1—V1—O5168.87 (6)C10—C8—C9122.07 (16)
N4—V1—O573.77 (5)O4—C9—O3124.44 (16)
O2—V1—O585.25 (5)O4—C9—C8121.82 (16)
O3—V1—O584.11 (5)O3—C9—C8113.73 (15)
N2—V1—O580.84 (5)C8—C10—H10A109.5
C7—O2—V1116.27 (11)C8—C10—H10B109.5
C9—O3—V1119.54 (11)H10A—C10—H10B109.5
C11—O5—V1113.82 (11)C8—C10—H10C109.5
C7—N1—N2106.71 (14)H10A—C10—H10C109.5
C8—N2—N1121.87 (15)H10B—C10—H10C109.5
C8—N2—V1119.25 (12)O5—C11—N3116.36 (15)
N1—N2—V1118.51 (11)O5—C11—C12122.63 (15)
C11—N3—N4114.16 (14)N3—C11—C12121.00 (15)
C11—N3—H3127.7 (16)C13—C12—C17120.13 (16)
N4—N3—H3118.0 (16)C13—C12—C11117.19 (15)
N3—N4—V1121.87 (11)C17—C12—C11122.68 (16)
N3—N4—H4108.9 (13)C14—C13—C12119.97 (17)
V1—N4—H4129.3 (13)C14—C13—H13120.0
C2—C1—C6119.31 (17)C12—C13—H13120.0
C2—C1—C7120.58 (16)C13—C14—C15119.90 (19)
C6—C1—C7120.11 (17)C13—C14—H14120.0
C3—C2—C1120.43 (18)C15—C14—H14120.0
C3—C2—H2119.8C16—C15—C14120.17 (18)
C1—C2—H2119.8C16—C15—H15119.9
C2—C3—C4120.11 (19)C14—C15—H15119.9
C2—C3—H3A119.9C15—C16—C17120.52 (18)
C4—C3—H3A119.9C15—C16—H16119.7
C5—C4—C3119.82 (19)C17—C16—H16119.7
C5—C4—H4A120.1C16—C17—C12119.28 (18)
C3—C4—H4A120.1C16—C17—H17120.4
C4—C5—C6120.10 (19)C12—C17—H17120.4

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.87 (1)1.97 (1)2.823 (2)164 (2)
N4—H4···O3i0.88 (1)2.05 (1)2.861 (2)154 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2396).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kopka, K. & Mattes, R. (1995). Z. Naturforsch. Teil B, 50, 1281–1286.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sundheim, A., Theers, C. & Mattes, R. (1994). Z. Naturforsch. Teil B, 49, 176–185.
  • Westrip, S. P. (2009). publCIF In preparation.

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