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(Benzohydrazidato-κ2N′,O)­[2-(benzoyl­hydrazono-κ2N,O)propion­ato-κO]oxido­vanadium(V)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 March 2009; accepted 16 March 2009; online 25 March 2009)

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[Kopka, K. & Mattes, R. (1995). Z. Naturforsch. Teil B, 50, 1281-1286.]); Sundheim et al. (1994[Sundheim, A., Theers, C. & Mattes, R. (1994). Z. Naturforsch. Teil B, 49, 176-185.]).

[Scheme 1]

Experimental

Crystal data
  • [V(C7H7N2O)(C10H8N2O3)O]

  • Mr = 406.27

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.816, Tmax = 0.982

  • 11614 measured reflections

  • 4010 independent reflections

  • 3330 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯O4i 0.87 (1) 1.97 (1) 2.823 (2) 164 (2)
N4—H4⋯O3i 0.88 (1) 2.05 (1) 2.861 (2) 154 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 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 top
Bruker SMART APEX
diffractometer
4010 independent reflections
Radiation source: fine-focus sealed tube3330 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.816, Tmax = 0.982k = 87
11614 measured reflectionsl = 3233
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 Å3
2 restraintsΔρmin = 0.38 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0342 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.39 e Å3
4010 reflectionsΔρmin = 0.38 e Å3
253 parameters
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, º) 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, º) 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 code: (i) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[V(C7H7N2O)(C10H8N2O3)O]
Mr406.27
Crystal system, space groupMonoclinic, P21/n
Temperature (K)123
a, b, c (Å)10.9424 (2), 6.2384 (1), 25.7215 (5)
β (°) 96.603 (1)
V3)1744.18 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.61
Crystal size (mm)0.35 × 0.10 × 0.03
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.816, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
11614, 4010, 3330
Rint0.027
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.091, 1.00
No. of reflections4010
No. of parameters253
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.39, 0.38

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) 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 code: (i) x+3/2, y1/2, z+3/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKopka, K. & Mattes, R. (1995). Z. Naturforsch. Teil B, 50, 1281–1286.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSundheim, A., Theers, C. & Mattes, R. (1994). Z. Naturforsch. Teil B, 49, 176–185.  CAS Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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