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Acta Cryst. (2009). E65, m422    [ doi:10.1107/S1600536809009520 ]

(Benzohydrazidato-[kappa]2N',O)[2-(benzoylhydrazono-[kappa]2N,O)propionato-[kappa]O]oxidovanadium(V)

H. W. Wong, K. M. Lo and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
(Benzohydrazidato-κ2N',O)[2-(benzoylhydrazono- κ2N,O)propionato-κO]oxidovanadium(V) top
Crystal data top
[V(C7H7N2O)(C10H8N2O3)O]F(000) = 832
Mr = 406.27Dx = 1.547 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		4010 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 top
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 = 1.00 w = 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 Å−3
2 restraintsΔρmin = −0.38 e Å−3
Crystal data top
[V(C7H7N2O)(C10H8N2O3)O]V = 1744.18 (5) Å3
Mr = 406.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.9424 (2) ŵ = 0.61 mm−1
b = 6.2384 (1) ÅT = 123 K
c = 25.7215 (5) Å0.35 × 0.10 × 0.03 mm
β = 96.603 (1)°
Data collection top
Bruker SMART APEX
diffractometer		4010 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3330 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.982Rint = 0.027
11614 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091Δρmax = 0.39 e Å−3
S = 1.00Δρmin = −0.38 e Å−3
4010 reflectionsAbsolute structure: ?
253 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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.

Sundheim, A., Theers, C. & Mattes, R. (1994). Z. Naturforsch. Teil B, 49, 176–185.

Westrip, S. P. (2009). publCIF. In preparation.