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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m718.
Published online 2009 June 6. doi:  10.1107/S1600536809019928
PMCID: PMC2969368

(4-Chloro­benzohydrazidato-κ2 N′,O)[2-(4-chloro­benzoyl­hydrazono-κ2 N,O)propionato(2−)-κO]oxidovanadium(V)

Abstract

In the crystal structure of the title compound, [VO(C7H6ClN2O)(C10H7ClN2O3)], the VV atom is N,O-chelated by the chloro­benzoyl­hydrazidate anion and O,N,O′-chelated by the (chloro­benzoyl­hydrazono)propionate dianion. The distorted octa­hedral trans-N2O4 coordination geometry is completed by the vanadyl O atom. In the crystal, mol­ecules are linked by N—H(...)O hydrogen bonds into a linear chain parallel to [010].

Related literature

For the analogous vanadyl complex without the chlorine substituent in the two ligands, see: Wong et al. (2009 [triangle]).

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Object name is e-65-0m718-scheme1.jpg

Experimental

Crystal data

  • [V(C7H6ClN2O)(C10H7ClN2O3)O]
  • M r = 475.15
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m718-efi1.jpg
  • a = 26.628 (2) Å
  • b = 5.7109 (3) Å
  • c = 24.772 (1) Å
  • β = 100.396 (3)°
  • V = 3705.2 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.86 mm−1
  • T = 119 K
  • 0.40 × 0.04 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.724, T max = 0.966
  • 11303 measured reflections
  • 4189 independent reflections
  • 2154 reflections with I > 2σ(I)
  • R int = 0.174

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.175
  • S = 0.97
  • 4189 reflections
  • 239 parameters
  • H-atom parameters constrained
  • Δρmax = 1.40 e Å−3
  • Δρmin = −1.20 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
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019928/xu2529sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019928/xu2529Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (RG020/09AFR) for supporting this study.

supplementary crystallographic information

Experimental

2-[p-Chlorobenzoylhydrazono]propionic acid was prepared from the condensation reaction of p-chlorobenzhydrazide and pyruvic acid. The compound (0.70 g, 3 mmol) and vanadyl sulfate (0.25 g, 1.5 mmol) in 20 ml of distilled water were heated for 5 h. Slow evaporation of the filtrate gave orange crystals.

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 to 1.5U(C). The nitrogen-bound H-atoms were similarly treated (N–H 0.88 Å).

All phenylene rings were refined was rigid hexagons of 1.39 Å sides.

The final difference Fourier map had a large peak/deep hole in the vicnity of the V1 atom.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of VO(C7H6ClN2O)(C10H7ClN2O3) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[V(C7H6ClN2O)(C10H7ClN2O3)O]F(000) = 1920
Mr = 475.15Dx = 1.704 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 957 reflections
a = 26.628 (2) Åθ = 2.5–23.1°
b = 5.7109 (3) ŵ = 0.86 mm1
c = 24.772 (1) ÅT = 119 K
β = 100.396 (3)°Prism, orange
V = 3705.2 (4) Å30.40 × 0.04 × 0.04 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer4189 independent reflections
Radiation source: fine-focus sealed tube2154 reflections with I > 2σ(I)
graphiteRint = 0.174
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −34→34
Tmin = 0.724, Tmax = 0.966k = −7→7
11303 measured reflectionsl = −32→30

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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0714P)2] where P = (Fo2 + 2Fc2)/3
4189 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 1.40 e Å3
0 restraintsΔρmin = −1.20 e Å3

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

xyzUiso*/Ueq
V10.66692 (3)0.32434 (15)0.27882 (4)0.0216 (3)
Cl10.44158 (5)0.7483 (2)0.46938 (6)0.0289 (4)
Cl20.84139 (5)−0.6026 (2)0.53131 (6)0.0294 (4)
O10.67515 (13)0.1122 (6)0.21738 (17)0.0236 (9)
O20.63441 (13)−0.1245 (6)0.15164 (17)0.0281 (9)
O30.62899 (12)0.4195 (6)0.33748 (16)0.0237 (9)
O40.69433 (12)0.0349 (6)0.33560 (16)0.0222 (9)
O50.65919 (13)0.5607 (6)0.24415 (18)0.0296 (10)
N10.60013 (15)0.1326 (7)0.2650 (2)0.0203 (10)
N20.56469 (15)0.1678 (7)0.2986 (2)0.0236 (11)
N30.76603 (15)0.2341 (7)0.34041 (19)0.0206 (10)
H30.79900.25550.35160.025*
N40.73671 (15)0.3820 (7)0.3060 (2)0.0215 (10)
H40.75060.51060.29580.026*
C10.63701 (18)−0.0159 (9)0.1950 (3)0.0228 (12)
C20.59319 (18)−0.0213 (9)0.2266 (2)0.0225 (12)
C30.55037 (18)−0.1879 (9)0.2136 (3)0.0280 (14)
H3A0.5521−0.30160.24350.042*
H3B0.5526−0.27020.17940.042*
H3C0.5180−0.10250.20920.042*
C40.58356 (18)0.3289 (8)0.3341 (3)0.0221 (12)
C50.55047 (11)0.4234 (5)0.37140 (15)0.0196 (12)
C60.50488 (12)0.3112 (5)0.37506 (15)0.0239 (13)
H60.49650.16710.35650.029*
C70.47159 (10)0.4100 (5)0.40592 (17)0.0249 (13)
H7A0.44040.33330.40840.030*
C80.48390 (11)0.6209 (5)0.43310 (15)0.0227 (12)
C90.52949 (12)0.7331 (5)0.42944 (15)0.0239 (12)
H90.53790.87720.44800.029*
C100.56278 (10)0.6343 (5)0.39859 (16)0.0254 (13)
H100.59390.71100.39610.031*
C110.74052 (18)0.0506 (8)0.3562 (2)0.0186 (12)
C120.76740 (11)−0.1137 (5)0.39758 (13)0.0222 (13)
C130.73990 (8)−0.3013 (5)0.41306 (14)0.0245 (13)
H130.7054−0.32490.39580.029*
C140.76286 (11)−0.4543 (5)0.45377 (15)0.0241 (12)
H140.7441−0.58250.46440.029*
C150.81333 (11)−0.4198 (5)0.47899 (13)0.0251 (13)
C160.84083 (9)−0.2323 (6)0.46350 (14)0.0273 (13)
H160.8753−0.20870.48070.033*
C170.81787 (10)−0.0792 (5)0.42280 (15)0.0251 (13)
H170.83670.04890.41220.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
V10.0156 (4)0.0218 (5)0.0292 (7)0.0012 (4)0.0087 (4)0.0014 (4)
Cl10.0244 (6)0.0351 (8)0.0291 (9)0.0057 (5)0.0097 (6)−0.0082 (6)
Cl20.0273 (7)0.0282 (7)0.0332 (10)0.0029 (6)0.0066 (6)0.0046 (7)
O10.0189 (17)0.0246 (19)0.028 (2)0.0046 (15)0.0074 (17)0.0015 (17)
O20.0217 (18)0.040 (2)0.024 (3)0.0046 (17)0.0079 (17)−0.004 (2)
O30.0151 (16)0.0256 (19)0.031 (3)−0.0022 (14)0.0067 (17)−0.0060 (18)
O40.0150 (16)0.0225 (18)0.029 (3)−0.0032 (14)0.0048 (17)−0.0022 (17)
O50.0269 (19)0.025 (2)0.039 (3)0.0037 (16)0.013 (2)0.0060 (19)
N10.018 (2)0.019 (2)0.027 (3)0.0043 (17)0.011 (2)0.003 (2)
N20.018 (2)0.024 (2)0.032 (3)0.0009 (18)0.014 (2)−0.004 (2)
N30.0137 (19)0.025 (2)0.023 (3)0.0018 (17)0.0037 (18)0.005 (2)
N40.020 (2)0.018 (2)0.028 (3)−0.0018 (17)0.009 (2)0.000 (2)
C10.016 (2)0.020 (3)0.033 (4)0.003 (2)0.004 (2)−0.001 (3)
C20.016 (2)0.021 (3)0.030 (4)0.004 (2)0.004 (2)0.003 (3)
C30.018 (2)0.032 (3)0.036 (4)−0.004 (2)0.010 (3)−0.007 (3)
C40.018 (2)0.017 (2)0.032 (4)0.000 (2)0.005 (2)0.004 (3)
C50.019 (2)0.020 (3)0.021 (3)0.002 (2)0.006 (2)−0.003 (2)
C60.022 (2)0.021 (3)0.029 (4)−0.003 (2)0.006 (2)−0.007 (3)
C70.021 (3)0.021 (3)0.034 (4)0.000 (2)0.009 (3)−0.001 (3)
C80.022 (2)0.023 (3)0.023 (3)0.005 (2)0.006 (2)−0.004 (2)
C90.026 (3)0.026 (3)0.019 (3)0.000 (2)0.003 (2)−0.005 (2)
C100.017 (2)0.028 (3)0.033 (4)−0.001 (2)0.006 (2)−0.003 (3)
C110.017 (2)0.022 (3)0.017 (3)−0.003 (2)0.005 (2)−0.004 (2)
C120.019 (2)0.018 (3)0.031 (4)0.002 (2)0.011 (2)−0.008 (2)
C130.016 (2)0.024 (3)0.036 (4)−0.003 (2)0.011 (2)−0.006 (3)
C140.026 (3)0.024 (3)0.023 (3)−0.002 (2)0.006 (2)0.000 (3)
C150.023 (3)0.027 (3)0.027 (4)0.007 (2)0.009 (3)0.002 (3)
C160.014 (2)0.032 (3)0.035 (4)−0.001 (2)0.003 (2)0.003 (3)
C170.023 (3)0.024 (3)0.029 (4)−0.003 (2)0.007 (3)0.005 (3)

Geometric parameters (Å, °)

V1—N12.064 (4)C3—H3C0.9800
V1—N41.888 (4)C4—C51.489 (5)
V1—O11.988 (4)C5—C61.3900
V1—O31.989 (3)C5—C101.3900
V1—O42.207 (4)C6—C71.3900
V1—O51.593 (4)C6—H60.9500
Cl1—C81.724 (2)C7—C81.3900
Cl2—C151.726 (3)C7—H7A0.9500
O1—C11.293 (6)C8—C91.3900
O2—C11.231 (6)C9—C101.3900
O3—C41.305 (5)C9—H90.9500
O4—C111.247 (6)C10—H100.9500
N1—C21.284 (7)C11—C121.476 (6)
N1—N21.381 (5)C12—C131.3900
N2—C41.308 (7)C12—C171.3900
N3—N41.344 (6)C13—C141.3900
N3—C111.345 (6)C13—H130.9500
N3—H30.8800C14—C151.3900
N4—H40.8800C14—H140.9500
C1—C21.518 (7)C15—C161.3900
C2—C31.475 (7)C16—C171.3900
C3—H3A0.9800C16—H160.9500
C3—H3B0.9800C17—H170.9500
O5—V1—N493.89 (19)O3—C4—C5117.5 (4)
O5—V1—O197.17 (18)N2—C4—C5118.3 (4)
N4—V1—O198.17 (16)C6—C5—C10120.0
O5—V1—O397.41 (17)C6—C5—C4119.7 (3)
N4—V1—O3106.77 (17)C10—C5—C4120.1 (3)
O1—V1—O3150.05 (14)C5—C6—C7120.0
O5—V1—N1109.67 (19)C5—C6—H6120.0
N4—V1—N1156.21 (18)C7—C6—H6120.0
O1—V1—N176.15 (15)C8—C7—C6120.0
O3—V1—N174.34 (15)C8—C7—H7A120.0
O5—V1—O4166.80 (18)C6—C7—H7A120.0
N4—V1—O473.27 (16)C9—C8—C7120.0
O1—V1—O487.83 (14)C9—C8—Cl1120.02 (18)
O3—V1—O483.82 (14)C7—C8—Cl1119.94 (18)
N1—V1—O483.36 (15)C10—C9—C8120.0
C1—O1—V1119.1 (3)C10—C9—H9120.0
C4—O3—V1115.6 (3)C8—C9—H9120.0
C11—O4—V1113.3 (3)C9—C10—C5120.0
C2—N1—N2121.6 (4)C9—C10—H10120.0
C2—N1—V1119.4 (3)C5—C10—H10120.0
N2—N1—V1119.0 (3)O4—C11—N3116.7 (5)
C4—N2—N1106.6 (4)O4—C11—C12123.9 (4)
N4—N3—C11114.1 (4)N3—C11—C12119.4 (4)
N4—N3—H3123.0C13—C12—C17120.0
C11—N3—H3123.0C13—C12—C11117.9 (3)
N3—N4—V1122.6 (3)C17—C12—C11122.0 (3)
N3—N4—H4118.7C12—C13—C14120.0
V1—N4—H4118.7C12—C13—H13120.0
O2—C1—O1125.1 (5)C14—C13—H13120.0
O2—C1—C2120.8 (5)C13—C14—C15120.0
O1—C1—C2114.1 (5)C13—C14—H14120.0
N1—C2—C3127.3 (5)C15—C14—H14120.0
N1—C2—C1110.3 (4)C16—C15—C14120.0
C3—C2—C1122.4 (5)C16—C15—Cl2119.67 (19)
C2—C3—H3A109.5C14—C15—Cl2120.29 (19)
C2—C3—H3B109.5C15—C16—C17120.0
H3A—C3—H3B109.5C15—C16—H16120.0
C2—C3—H3C109.5C17—C16—H16120.0
H3A—C3—H3C109.5C16—C17—C12120.0
H3B—C3—H3C109.5C16—C17—H17120.0
O3—C4—N2124.2 (5)C12—C17—H17120.0
O5—V1—O1—C1−101.5 (4)O1—C1—C2—N19.8 (6)
N4—V1—O1—C1163.5 (4)O2—C1—C2—C312.0 (8)
O3—V1—O1—C117.1 (6)O1—C1—C2—C3−169.0 (5)
N1—V1—O1—C17.1 (4)V1—O3—C4—N26.8 (7)
O4—V1—O1—C190.8 (4)V1—O3—C4—C5−170.4 (3)
O5—V1—O3—C4104.1 (4)N1—N2—C4—O3−4.5 (7)
N4—V1—O3—C4−159.6 (4)N1—N2—C4—C5172.6 (4)
O1—V1—O3—C4−14.5 (5)O3—C4—C5—C6−170.8 (4)
N1—V1—O3—C4−4.3 (4)N2—C4—C5—C611.9 (6)
O4—V1—O3—C4−89.1 (4)O3—C4—C5—C1015.1 (6)
O5—V1—O4—C11−14.2 (9)N2—C4—C5—C10−162.2 (4)
N4—V1—O4—C11−0.7 (3)C10—C5—C6—C70.0
O1—V1—O4—C1198.5 (3)C4—C5—C6—C7−174.2 (4)
O3—V1—O4—C11−110.3 (3)C5—C6—C7—C80.0
N1—V1—O4—C11174.8 (4)C6—C7—C8—C90.0
O5—V1—N1—C291.9 (4)C6—C7—C8—Cl1177.7 (3)
N4—V1—N1—C2−79.5 (6)C7—C8—C9—C100.0
O1—V1—N1—C2−0.8 (4)Cl1—C8—C9—C10−177.7 (3)
O3—V1—N1—C2−175.6 (4)C8—C9—C10—C50.0
O4—V1—N1—C2−90.2 (4)C6—C5—C10—C90.0
O5—V1—N1—N2−90.2 (4)C4—C5—C10—C9174.1 (4)
N4—V1—N1—N298.4 (5)V1—O4—C11—N3−1.1 (6)
O1—V1—N1—N2177.0 (4)V1—O4—C11—C12176.7 (3)
O3—V1—N1—N22.2 (3)N4—N3—C11—O43.1 (7)
O4—V1—N1—N287.6 (4)N4—N3—C11—C12−174.9 (4)
C2—N1—N2—C4178.1 (5)O4—C11—C12—C132.1 (6)
V1—N1—N2—C40.3 (5)N3—C11—C12—C13179.9 (3)
C11—N3—N4—V1−4.0 (6)O4—C11—C12—C17−174.7 (4)
O5—V1—N4—N3179.5 (4)N3—C11—C12—C173.1 (5)
O1—V1—N4—N3−82.7 (4)C17—C12—C13—C140.0
O3—V1—N4—N380.5 (4)C11—C12—C13—C14−176.9 (3)
N1—V1—N4—N3−8.6 (7)C12—C13—C14—C150.0
O4—V1—N4—N32.5 (4)C13—C14—C15—C160.0
V1—O1—C1—O2167.7 (4)C13—C14—C15—Cl2177.6 (3)
V1—O1—C1—C2−11.3 (6)C14—C15—C16—C170.0
N2—N1—C2—C3−3.4 (8)Cl2—C15—C16—C17−177.6 (3)
V1—N1—C2—C3174.5 (4)C15—C16—C17—C120.0
N2—N1—C2—C1177.9 (4)C13—C12—C17—C160.0
V1—N1—C2—C1−4.3 (6)C11—C12—C17—C16176.8 (3)
O2—C1—C2—N1−169.2 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O2i0.881.922.744 (5)156
N4—H4···O1i0.882.142.840 (5)136

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2529).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Wong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m422. [PMC free article] [PubMed]

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