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

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

doi:10.1107/S1600536809009520

metal-organic compounds

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Volume 65| Part 4| April 2009| Page m422

doi:10.1107/S1600536809009520

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

Hon Wee Wong,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^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 V^V 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 ); Sundheim et al. (1994 ).

Experimental

Crystal data

[V(C₇H₇N₂O)(C₁₀H₈N₂O₃)O]
M_r = 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 ) 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[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
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

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.

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

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
M_r = 406.27	D_x = 1.547 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3550 reflections
a = 10.9424 (2) Å	θ = 2.9–28.0°
b = 6.2384 (1) Å	µ = 0.61 mm⁻¹
c = 25.7215 (5) Å	T = 123 K
β = 96.603 (1)°	Prism, red
V = 1744.18 (5) Å³	0.35 × 0.10 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4010 independent reflections
Radiation source: fine-focus sealed tube	3330 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.816, T_max = 0.982	k = −8→7
11614 measured reflections	l = −32→33

Refinement top

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0443P)² + 0.9013P] where P = (F_o² + 2F_c²)/3
4010 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.39 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[V(C₇H₇N₂O)(C₁₀H₈N₂O₃)O]	V = 1744.18 (5) Å³
M_r = 406.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9424 (2) Å	µ = 0.61 mm⁻¹
b = 6.2384 (1) Å	T = 123 K
c = 25.7215 (5) Å	0.35 × 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)
T_min = 0.816, T_max = 0.982	R_int = 0.027
11614 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.39 e Å⁻³
4010 reflections	Δρ_min = −0.38 e Å⁻³
253 parameters

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

	x	y	z	U_iso*/U_eq
V1	0.63939 (3)	0.51362 (5)	0.667678 (11)	0.02025 (10)
O1	0.71456 (13)	0.3013 (2)	0.65899 (5)	0.0310 (3)
O2	0.47660 (11)	0.4125 (2)	0.63552 (5)	0.0252 (3)
O3	0.77761 (11)	0.7223 (2)	0.66978 (4)	0.0227 (3)
O4	0.87206 (11)	0.9694 (2)	0.62563 (5)	0.0250 (3)
O5	0.53800 (11)	0.7850 (2)	0.69541 (4)	0.0229 (3)
N1	0.49712 (13)	0.6388 (3)	0.56603 (5)	0.0230 (3)
N2	0.60460 (13)	0.6815 (2)	0.59808 (5)	0.0200 (3)
N3	0.57784 (13)	0.6090 (2)	0.76970 (5)	0.0204 (3)
H3	0.582 (2)	0.584 (4)	0.8033 (4)	0.039 (6)*
N4	0.63345 (14)	0.4678 (2)	0.73974 (6)	0.0213 (3)
H4	0.6650 (17)	0.363 (3)	0.7597 (7)	0.029 (6)*
C1	0.32064 (16)	0.4069 (3)	0.56296 (7)	0.0235 (4)
C2	0.26918 (17)	0.4956 (3)	0.51595 (7)	0.0271 (4)
H2	0.3101	0.6096	0.5006	0.033*
C3	0.15882 (18)	0.4191 (3)	0.49134 (8)	0.0316 (4)
H3A	0.1242	0.4805	0.4592	0.038*
C4	0.09839 (18)	0.2527 (3)	0.51358 (8)	0.0346 (5)
H4A	0.0221	0.2011	0.4968	0.041*
C5	0.14961 (19)	0.1621 (4)	0.56019 (8)	0.0366 (5)
H5	0.1086	0.0477	0.5754	0.044*
C6	0.26067 (19)	0.2380 (3)	0.58478 (8)	0.0330 (5)
H6	0.2959	0.1747	0.6166	0.040*
C7	0.43810 (16)	0.4902 (3)	0.58978 (7)	0.0221 (4)
C8	0.67646 (16)	0.8356 (3)	0.58852 (7)	0.0217 (4)
C9	0.78589 (16)	0.8481 (3)	0.62982 (6)	0.0212 (4)
C10	0.65613 (17)	0.9934 (3)	0.54563 (7)	0.0273 (4)
H10A	0.6174	0.9223	0.5139	0.041*
H10B	0.7352	1.0546	0.5388	0.041*
H10C	0.6022	1.1080	0.5557	0.041*
C11	0.52823 (15)	0.7794 (3)	0.74341 (6)	0.0191 (3)
C12	0.46480 (15)	0.9478 (3)	0.77016 (7)	0.0207 (4)
C13	0.41422 (15)	1.1174 (3)	0.73968 (7)	0.0235 (4)
H13	0.4241	1.1237	0.7035	0.028*
C14	0.34966 (17)	1.2765 (3)	0.76211 (8)	0.0297 (4)
H14	0.3142	1.3913	0.7413	0.036*
C15	0.33666 (18)	1.2683 (3)	0.81518 (8)	0.0341 (5)
H15	0.2914	1.3766	0.8305	0.041*
C16	0.38955 (18)	1.1029 (4)	0.84576 (8)	0.0335 (5)
H16	0.3821	1.1002	0.8822	0.040*
C17	0.45334 (17)	0.9412 (3)	0.82367 (7)	0.0275 (4)
H17	0.4889	0.8270	0.8447	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.02461 (16)	0.02017 (17)	0.01501 (15)	0.00332 (12)	−0.00179 (11)	−0.00063 (11)
O1	0.0386 (8)	0.0277 (7)	0.0250 (7)	0.0083 (6)	−0.0030 (6)	−0.0049 (6)
O2	0.0300 (7)	0.0264 (7)	0.0178 (6)	−0.0041 (6)	−0.0026 (5)	0.0027 (5)
O3	0.0242 (6)	0.0258 (7)	0.0172 (6)	0.0014 (5)	−0.0019 (5)	−0.0025 (5)
O4	0.0224 (6)	0.0308 (7)	0.0215 (6)	−0.0022 (5)	0.0014 (5)	−0.0059 (5)
O5	0.0279 (6)	0.0242 (7)	0.0165 (6)	0.0053 (5)	0.0026 (5)	0.0028 (5)
N1	0.0215 (7)	0.0289 (8)	0.0172 (7)	−0.0031 (6)	−0.0030 (6)	0.0004 (6)
N2	0.0206 (7)	0.0252 (8)	0.0137 (6)	0.0013 (6)	−0.0007 (5)	−0.0025 (6)
N3	0.0226 (7)	0.0220 (8)	0.0160 (7)	0.0002 (6)	0.0002 (6)	0.0015 (6)
N4	0.0241 (7)	0.0199 (8)	0.0190 (7)	0.0034 (6)	−0.0016 (6)	0.0014 (6)
C1	0.0243 (9)	0.0263 (9)	0.0196 (8)	−0.0021 (7)	0.0010 (7)	−0.0026 (7)
C2	0.0265 (9)	0.0267 (10)	0.0273 (9)	−0.0012 (8)	−0.0003 (7)	0.0026 (8)
C3	0.0283 (10)	0.0350 (11)	0.0292 (10)	0.0044 (9)	−0.0060 (8)	−0.0004 (9)
C4	0.0261 (10)	0.0374 (12)	0.0386 (11)	−0.0060 (9)	−0.0035 (8)	−0.0076 (9)
C5	0.0387 (11)	0.0377 (12)	0.0330 (11)	−0.0150 (10)	0.0019 (9)	−0.0001 (9)
C6	0.0381 (11)	0.0372 (12)	0.0224 (9)	−0.0108 (9)	−0.0021 (8)	0.0017 (8)
C7	0.0256 (9)	0.0230 (9)	0.0173 (8)	0.0005 (7)	0.0007 (7)	−0.0019 (7)
C8	0.0229 (8)	0.0244 (9)	0.0176 (8)	0.0020 (7)	0.0016 (7)	−0.0030 (7)
C9	0.0222 (8)	0.0236 (9)	0.0176 (8)	0.0049 (7)	0.0009 (6)	−0.0065 (7)
C10	0.0277 (9)	0.0282 (10)	0.0249 (9)	−0.0042 (8)	−0.0024 (7)	0.0036 (8)
C11	0.0180 (8)	0.0206 (8)	0.0180 (8)	−0.0017 (7)	−0.0004 (6)	0.0006 (7)
C12	0.0154 (8)	0.0232 (9)	0.0236 (9)	−0.0025 (7)	0.0036 (6)	−0.0017 (7)
C13	0.0186 (8)	0.0254 (9)	0.0266 (9)	−0.0025 (7)	0.0027 (7)	0.0008 (7)
C14	0.0227 (9)	0.0252 (10)	0.0408 (11)	0.0006 (8)	0.0023 (8)	0.0005 (8)
C15	0.0262 (10)	0.0337 (11)	0.0436 (12)	0.0012 (8)	0.0095 (9)	−0.0120 (9)
C16	0.0339 (10)	0.0403 (12)	0.0280 (10)	−0.0011 (9)	0.0109 (8)	−0.0078 (9)
C17	0.0267 (9)	0.0329 (10)	0.0235 (9)	0.0014 (8)	0.0053 (7)	−0.0009 (8)

Geometric parameters (Å, º) top

V1—O1	1.589 (1)	C3—H3A	0.9500
V1—O2	1.979 (1)	C4—C5	1.384 (3)
V1—O3	1.992 (1)	C4—H4A	0.9500
V1—O5	2.188 (1)	C5—C6	1.387 (3)
V1—N2	2.071 (1)	C5—H5	0.9500
V1—N4	1.884 (2)	C6—H6	0.9500
O2—C7	1.297 (2)	C8—C10	1.476 (3)
O3—C9	1.304 (2)	C8—C9	1.509 (2)
O4—C9	1.223 (2)	C10—H10A	0.9800
O5—C11	1.252 (2)	C10—H10B	0.9800
N1—C7	1.319 (2)	C10—H10C	0.9800
N1—N2	1.382 (2)	C11—C12	1.473 (2)
N2—C8	1.283 (2)	C12—C13	1.393 (3)
N3—C11	1.341 (2)	C12—C17	1.397 (2)
N3—N4	1.359 (2)	C13—C14	1.382 (3)
N3—H3	0.874 (9)	C13—H13	0.9500
N4—H4	0.879 (9)	C14—C15	1.389 (3)
C1—C2	1.389 (3)	C14—H14	0.9500
C1—C6	1.393 (3)	C15—C16	1.383 (3)
C1—C7	1.481 (2)	C15—H15	0.9500
C2—C3	1.382 (3)	C16—C17	1.385 (3)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.389 (3)	C17—H17	0.9500

O1—V1—N4	95.10 (7)	C4—C5—H5	120.0
O1—V1—O2	97.53 (7)	C6—C5—H5	120.0
N4—V1—O2	103.39 (6)	C5—C6—C1	120.22 (19)
O1—V1—O3	98.34 (7)	C5—C6—H6	119.9
N4—V1—O3	100.63 (6)	C1—C6—H6	119.9
O2—V1—O3	149.76 (5)	O2—C7—N1	123.88 (16)
O1—V1—N2	110.29 (6)	O2—C7—C1	117.71 (16)
N4—V1—N2	154.60 (6)	N1—C7—C1	118.41 (15)
O2—V1—N2	74.50 (5)	N2—C8—C10	126.85 (16)
O3—V1—N2	75.90 (5)	N2—C8—C9	110.97 (15)
O1—V1—O5	168.87 (6)	C10—C8—C9	122.07 (16)
N4—V1—O5	73.77 (5)	O4—C9—O3	124.44 (16)
O2—V1—O5	85.25 (5)	O4—C9—C8	121.82 (16)
O3—V1—O5	84.11 (5)	O3—C9—C8	113.73 (15)
N2—V1—O5	80.84 (5)	C8—C10—H10A	109.5
C7—O2—V1	116.27 (11)	C8—C10—H10B	109.5
C9—O3—V1	119.54 (11)	H10A—C10—H10B	109.5
C11—O5—V1	113.82 (11)	C8—C10—H10C	109.5
C7—N1—N2	106.71 (14)	H10A—C10—H10C	109.5
C8—N2—N1	121.87 (15)	H10B—C10—H10C	109.5
C8—N2—V1	119.25 (12)	O5—C11—N3	116.36 (15)
N1—N2—V1	118.51 (11)	O5—C11—C12	122.63 (15)
C11—N3—N4	114.16 (14)	N3—C11—C12	121.00 (15)
C11—N3—H3	127.7 (16)	C13—C12—C17	120.13 (16)
N4—N3—H3	118.0 (16)	C13—C12—C11	117.19 (15)
N3—N4—V1	121.87 (11)	C17—C12—C11	122.68 (16)
N3—N4—H4	108.9 (13)	C14—C13—C12	119.97 (17)
V1—N4—H4	129.3 (13)	C14—C13—H13	120.0
C2—C1—C6	119.31 (17)	C12—C13—H13	120.0
C2—C1—C7	120.58 (16)	C13—C14—C15	119.90 (19)
C6—C1—C7	120.11 (17)	C13—C14—H14	120.0
C3—C2—C1	120.43 (18)	C15—C14—H14	120.0
C3—C2—H2	119.8	C16—C15—C14	120.17 (18)
C1—C2—H2	119.8	C16—C15—H15	119.9
C2—C3—C4	120.11 (19)	C14—C15—H15	119.9
C2—C3—H3A	119.9	C15—C16—C17	120.52 (18)
C4—C3—H3A	119.9	C15—C16—H16	119.7
C5—C4—C3	119.82 (19)	C17—C16—H16	119.7
C5—C4—H4A	120.1	C16—C17—C12	119.28 (18)
C3—C4—H4A	120.1	C16—C17—H17	120.4
C4—C5—C6	120.10 (19)	C12—C17—H17	120.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[V(C₇H₇N₂O)(C₁₀H₈N₂O₃)O]
M_r	406.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	10.9424 (2), 6.2384 (1), 25.7215 (5)
β (°)	96.603 (1)
V (Å³)	1744.18 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.35 × 0.10 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.816, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	11614, 4010, 3330
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.091, 1.00
No. of reflections	4010
No. of parameters	253
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+3/2, y−1/2, −z+3/2.

Acknowledgements

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

References

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