(4-Chloro­benzohydrazidato-κ2N′,O)[2-(4-chloro­benzoyl­hydrazono-κ2N,O)propionato(2−)-κO]oxidovanadium(V)

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

doi:10.1107/S1600536809019928

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m718

doi:10.1107/S1600536809019928

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(4-Chlorobenzohydrazidato-κ²N′,O)[2-(4-chlorobenzoylhydrazono-κ²N,O)propionato(2−)-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 21 May 2009; accepted 26 May 2009; online 6 June 2009)

In the crystal structure of the title compound, [VO(C₇H₆ClN₂O)(C₁₀H₇ClN₂O₃)], the V^V 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 ).

Experimental

Crystal data

[V(C₇H₆ClN₂O)(C₁₀H₇ClN₂O₃)O]
M_r = 475.15
Monoclinic, C 2/c
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 ) 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[F² > 2σ(F²)] = 0.059
wR(F²) = 0.175
S = 0.97
4189 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 1.40 e Å⁻³
Δρ_min = −1.20 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—N1	2.064 (4)
V1—N4	1.888 (4)
V1—O1	1.988 (4)
V1—O3	1.989 (3)
V1—O4	2.207 (4)
V1—O5	1.593 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2ⁱ	0.88	1.92	2.744 (5)	156
N4—H4⋯O1ⁱ	0.88	2.14	2.840 (5)	136
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536809019928/xu2529sup1.cif

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

checkCIF report

Related literature top

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

Experimental top

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.

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(C₇H₆ClN₂O)(C₁₀H₇ClN₂O₃) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

(4-Chlorobenzohydrazidato-κ²N',O)[2-(4- chlorobenzoylhydrazono-κ²N,O)propionato(2-)- κO]oxidovanadium(V) top

Crystal data top

[V(C₇H₆ClN₂O)(C₁₀H₇ClN₂O₃)O]	F(000) = 1920
M_r = 475.15	D_x = 1.704 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 957 reflections
a = 26.628 (2) Å	θ = 2.5–23.1°
b = 5.7109 (3) Å	µ = 0.86 mm⁻¹
c = 24.772 (1) Å	T = 119 K
β = 100.396 (3)°	Prism, orange
V = 3705.2 (4) Å³	0.40 × 0.04 × 0.04 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	4189 independent reflections
Radiation source: fine-focus sealed tube	2154 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.174
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→34
T_min = 0.724, T_max = 0.966	k = −7→7
11303 measured reflections	l = −32→30

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0714P)²] where P = (F_o² + 2F_c²)/3
4189 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 1.40 e Å⁻³
0 restraints	Δρ_min = −1.20 e Å⁻³

Crystal data top

[V(C₇H₆ClN₂O)(C₁₀H₇ClN₂O₃)O]	V = 3705.2 (4) Å³
M_r = 475.15	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.628 (2) Å	µ = 0.86 mm⁻¹
b = 5.7109 (3) Å	T = 119 K
c = 24.772 (1) Å	0.40 × 0.04 × 0.04 mm
β = 100.396 (3)°

Data collection top

Bruker SMART APEX diffractometer	4189 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2154 reflections with I > 2σ(I)
T_min = 0.724, T_max = 0.966	R_int = 0.174
11303 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 0.97	Δρ_max = 1.40 e Å⁻³
4189 reflections	Δρ_min = −1.20 e Å⁻³
239 parameters

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

	x	y	z	U_iso*/U_eq
V1	0.66692 (3)	0.32434 (15)	0.27882 (4)	0.0216 (3)
Cl1	0.44158 (5)	0.7483 (2)	0.46938 (6)	0.0289 (4)
Cl2	0.84139 (5)	−0.6026 (2)	0.53131 (6)	0.0294 (4)
O1	0.67515 (13)	0.1122 (6)	0.21738 (17)	0.0236 (9)
O2	0.63441 (13)	−0.1245 (6)	0.15164 (17)	0.0281 (9)
O3	0.62899 (12)	0.4195 (6)	0.33748 (16)	0.0237 (9)
O4	0.69433 (12)	0.0349 (6)	0.33560 (16)	0.0222 (9)
O5	0.65919 (13)	0.5607 (6)	0.24415 (18)	0.0296 (10)
N1	0.60013 (15)	0.1326 (7)	0.2650 (2)	0.0203 (10)
N2	0.56469 (15)	0.1678 (7)	0.2986 (2)	0.0236 (11)
N3	0.76603 (15)	0.2341 (7)	0.34041 (19)	0.0206 (10)
H3	0.7990	0.2555	0.3516	0.025*
N4	0.73671 (15)	0.3820 (7)	0.3060 (2)	0.0215 (10)
H4	0.7506	0.5106	0.2958	0.026*
C1	0.63701 (18)	−0.0159 (9)	0.1950 (3)	0.0228 (12)
C2	0.59319 (18)	−0.0213 (9)	0.2266 (2)	0.0225 (12)
C3	0.55037 (18)	−0.1879 (9)	0.2136 (3)	0.0280 (14)
H3A	0.5521	−0.3016	0.2435	0.042*
H3B	0.5526	−0.2702	0.1794	0.042*
H3C	0.5180	−0.1025	0.2092	0.042*
C4	0.58356 (18)	0.3289 (8)	0.3341 (3)	0.0221 (12)
C5	0.55047 (11)	0.4234 (5)	0.37140 (15)	0.0196 (12)
C6	0.50488 (12)	0.3112 (5)	0.37506 (15)	0.0239 (13)
H6	0.4965	0.1671	0.3565	0.029*
C7	0.47159 (10)	0.4100 (5)	0.40592 (17)	0.0249 (13)
H7A	0.4404	0.3333	0.4084	0.030*
C8	0.48390 (11)	0.6209 (5)	0.43310 (15)	0.0227 (12)
C9	0.52949 (12)	0.7331 (5)	0.42944 (15)	0.0239 (12)
H9	0.5379	0.8772	0.4480	0.029*
C10	0.56278 (10)	0.6343 (5)	0.39859 (16)	0.0254 (13)
H10	0.5939	0.7110	0.3961	0.031*
C11	0.74052 (18)	0.0506 (8)	0.3562 (2)	0.0186 (12)
C12	0.76740 (11)	−0.1137 (5)	0.39758 (13)	0.0222 (13)
C13	0.73990 (8)	−0.3013 (5)	0.41306 (14)	0.0245 (13)
H13	0.7054	−0.3249	0.3958	0.029*
C14	0.76286 (11)	−0.4543 (5)	0.45377 (15)	0.0241 (12)
H14	0.7441	−0.5825	0.4644	0.029*
C15	0.81333 (11)	−0.4198 (5)	0.47899 (13)	0.0251 (13)
C16	0.84083 (9)	−0.2323 (6)	0.46350 (14)	0.0273 (13)
H16	0.8753	−0.2087	0.4807	0.033*
C17	0.81787 (10)	−0.0792 (5)	0.42280 (15)	0.0251 (13)
H17	0.8367	0.0489	0.4122	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0156 (4)	0.0218 (5)	0.0292 (7)	0.0012 (4)	0.0087 (4)	0.0014 (4)
Cl1	0.0244 (6)	0.0351 (8)	0.0291 (9)	0.0057 (5)	0.0097 (6)	−0.0082 (6)
Cl2	0.0273 (7)	0.0282 (7)	0.0332 (10)	0.0029 (6)	0.0066 (6)	0.0046 (7)
O1	0.0189 (17)	0.0246 (19)	0.028 (2)	0.0046 (15)	0.0074 (17)	0.0015 (17)
O2	0.0217 (18)	0.040 (2)	0.024 (3)	0.0046 (17)	0.0079 (17)	−0.004 (2)
O3	0.0151 (16)	0.0256 (19)	0.031 (3)	−0.0022 (14)	0.0067 (17)	−0.0060 (18)
O4	0.0150 (16)	0.0225 (18)	0.029 (3)	−0.0032 (14)	0.0048 (17)	−0.0022 (17)
O5	0.0269 (19)	0.025 (2)	0.039 (3)	0.0037 (16)	0.013 (2)	0.0060 (19)
N1	0.018 (2)	0.019 (2)	0.027 (3)	0.0043 (17)	0.011 (2)	0.003 (2)
N2	0.018 (2)	0.024 (2)	0.032 (3)	0.0009 (18)	0.014 (2)	−0.004 (2)
N3	0.0137 (19)	0.025 (2)	0.023 (3)	0.0018 (17)	0.0037 (18)	0.005 (2)
N4	0.020 (2)	0.018 (2)	0.028 (3)	−0.0018 (17)	0.009 (2)	0.000 (2)
C1	0.016 (2)	0.020 (3)	0.033 (4)	0.003 (2)	0.004 (2)	−0.001 (3)
C2	0.016 (2)	0.021 (3)	0.030 (4)	0.004 (2)	0.004 (2)	0.003 (3)
C3	0.018 (2)	0.032 (3)	0.036 (4)	−0.004 (2)	0.010 (3)	−0.007 (3)
C4	0.018 (2)	0.017 (2)	0.032 (4)	0.000 (2)	0.005 (2)	0.004 (3)
C5	0.019 (2)	0.020 (3)	0.021 (3)	0.002 (2)	0.006 (2)	−0.003 (2)
C6	0.022 (2)	0.021 (3)	0.029 (4)	−0.003 (2)	0.006 (2)	−0.007 (3)
C7	0.021 (3)	0.021 (3)	0.034 (4)	0.000 (2)	0.009 (3)	−0.001 (3)
C8	0.022 (2)	0.023 (3)	0.023 (3)	0.005 (2)	0.006 (2)	−0.004 (2)
C9	0.026 (3)	0.026 (3)	0.019 (3)	0.000 (2)	0.003 (2)	−0.005 (2)
C10	0.017 (2)	0.028 (3)	0.033 (4)	−0.001 (2)	0.006 (2)	−0.003 (3)
C11	0.017 (2)	0.022 (3)	0.017 (3)	−0.003 (2)	0.005 (2)	−0.004 (2)
C12	0.019 (2)	0.018 (3)	0.031 (4)	0.002 (2)	0.011 (2)	−0.008 (2)
C13	0.016 (2)	0.024 (3)	0.036 (4)	−0.003 (2)	0.011 (2)	−0.006 (3)
C14	0.026 (3)	0.024 (3)	0.023 (3)	−0.002 (2)	0.006 (2)	0.000 (3)
C15	0.023 (3)	0.027 (3)	0.027 (4)	0.007 (2)	0.009 (3)	0.002 (3)
C16	0.014 (2)	0.032 (3)	0.035 (4)	−0.001 (2)	0.003 (2)	0.003 (3)
C17	0.023 (3)	0.024 (3)	0.029 (4)	−0.003 (2)	0.007 (3)	0.005 (3)

Geometric parameters (Å, º) top

V1—N1	2.064 (4)	C3—H3C	0.9800
V1—N4	1.888 (4)	C4—C5	1.489 (5)
V1—O1	1.988 (4)	C5—C6	1.3900
V1—O3	1.989 (3)	C5—C10	1.3900
V1—O4	2.207 (4)	C6—C7	1.3900
V1—O5	1.593 (4)	C6—H6	0.9500
Cl1—C8	1.724 (2)	C7—C8	1.3900
Cl2—C15	1.726 (3)	C7—H7A	0.9500
O1—C1	1.293 (6)	C8—C9	1.3900
O2—C1	1.231 (6)	C9—C10	1.3900
O3—C4	1.305 (5)	C9—H9	0.9500
O4—C11	1.247 (6)	C10—H10	0.9500
N1—C2	1.284 (7)	C11—C12	1.476 (6)
N1—N2	1.381 (5)	C12—C13	1.3900
N2—C4	1.308 (7)	C12—C17	1.3900
N3—N4	1.344 (6)	C13—C14	1.3900
N3—C11	1.345 (6)	C13—H13	0.9500
N3—H3	0.8800	C14—C15	1.3900
N4—H4	0.8800	C14—H14	0.9500
C1—C2	1.518 (7)	C15—C16	1.3900
C2—C3	1.475 (7)	C16—C17	1.3900
C3—H3A	0.9800	C16—H16	0.9500
C3—H3B	0.9800	C17—H17	0.9500

O5—V1—N4	93.89 (19)	O3—C4—C5	117.5 (4)
O5—V1—O1	97.17 (18)	N2—C4—C5	118.3 (4)
N4—V1—O1	98.17 (16)	C6—C5—C10	120.0
O5—V1—O3	97.41 (17)	C6—C5—C4	119.7 (3)
N4—V1—O3	106.77 (17)	C10—C5—C4	120.1 (3)
O1—V1—O3	150.05 (14)	C5—C6—C7	120.0
O5—V1—N1	109.67 (19)	C5—C6—H6	120.0
N4—V1—N1	156.21 (18)	C7—C6—H6	120.0
O1—V1—N1	76.15 (15)	C8—C7—C6	120.0
O3—V1—N1	74.34 (15)	C8—C7—H7A	120.0
O5—V1—O4	166.80 (18)	C6—C7—H7A	120.0
N4—V1—O4	73.27 (16)	C9—C8—C7	120.0
O1—V1—O4	87.83 (14)	C9—C8—Cl1	120.02 (18)
O3—V1—O4	83.82 (14)	C7—C8—Cl1	119.94 (18)
N1—V1—O4	83.36 (15)	C10—C9—C8	120.0
C1—O1—V1	119.1 (3)	C10—C9—H9	120.0
C4—O3—V1	115.6 (3)	C8—C9—H9	120.0
C11—O4—V1	113.3 (3)	C9—C10—C5	120.0
C2—N1—N2	121.6 (4)	C9—C10—H10	120.0
C2—N1—V1	119.4 (3)	C5—C10—H10	120.0
N2—N1—V1	119.0 (3)	O4—C11—N3	116.7 (5)
C4—N2—N1	106.6 (4)	O4—C11—C12	123.9 (4)
N4—N3—C11	114.1 (4)	N3—C11—C12	119.4 (4)
N4—N3—H3	123.0	C13—C12—C17	120.0
C11—N3—H3	123.0	C13—C12—C11	117.9 (3)
N3—N4—V1	122.6 (3)	C17—C12—C11	122.0 (3)
N3—N4—H4	118.7	C12—C13—C14	120.0
V1—N4—H4	118.7	C12—C13—H13	120.0
O2—C1—O1	125.1 (5)	C14—C13—H13	120.0
O2—C1—C2	120.8 (5)	C13—C14—C15	120.0
O1—C1—C2	114.1 (5)	C13—C14—H14	120.0
N1—C2—C3	127.3 (5)	C15—C14—H14	120.0
N1—C2—C1	110.3 (4)	C16—C15—C14	120.0
C3—C2—C1	122.4 (5)	C16—C15—Cl2	119.67 (19)
C2—C3—H3A	109.5	C14—C15—Cl2	120.29 (19)
C2—C3—H3B	109.5	C15—C16—C17	120.0
H3A—C3—H3B	109.5	C15—C16—H16	120.0
C2—C3—H3C	109.5	C17—C16—H16	120.0
H3A—C3—H3C	109.5	C16—C17—C12	120.0
H3B—C3—H3C	109.5	C16—C17—H17	120.0
O3—C4—N2	124.2 (5)	C12—C17—H17	120.0

O5—V1—O1—C1	−101.5 (4)	O1—C1—C2—N1	9.8 (6)
N4—V1—O1—C1	163.5 (4)	O2—C1—C2—C3	12.0 (8)
O3—V1—O1—C1	17.1 (6)	O1—C1—C2—C3	−169.0 (5)
N1—V1—O1—C1	7.1 (4)	V1—O3—C4—N2	6.8 (7)
O4—V1—O1—C1	90.8 (4)	V1—O3—C4—C5	−170.4 (3)
O5—V1—O3—C4	104.1 (4)	N1—N2—C4—O3	−4.5 (7)
N4—V1—O3—C4	−159.6 (4)	N1—N2—C4—C5	172.6 (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—C6	11.9 (6)
O4—V1—O3—C4	−89.1 (4)	O3—C4—C5—C10	15.1 (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—C7	0.0
O1—V1—O4—C11	98.5 (3)	C4—C5—C6—C7	−174.2 (4)
O3—V1—O4—C11	−110.3 (3)	C5—C6—C7—C8	0.0
N1—V1—O4—C11	174.8 (4)	C6—C7—C8—C9	0.0
O5—V1—N1—C2	91.9 (4)	C6—C7—C8—Cl1	177.7 (3)
N4—V1—N1—C2	−79.5 (6)	C7—C8—C9—C10	0.0
O1—V1—N1—C2	−0.8 (4)	Cl1—C8—C9—C10	−177.7 (3)
O3—V1—N1—C2	−175.6 (4)	C8—C9—C10—C5	0.0
O4—V1—N1—C2	−90.2 (4)	C6—C5—C10—C9	0.0
O5—V1—N1—N2	−90.2 (4)	C4—C5—C10—C9	174.1 (4)
N4—V1—N1—N2	98.4 (5)	V1—O4—C11—N3	−1.1 (6)
O1—V1—N1—N2	177.0 (4)	V1—O4—C11—C12	176.7 (3)
O3—V1—N1—N2	2.2 (3)	N4—N3—C11—O4	3.1 (7)
O4—V1—N1—N2	87.6 (4)	N4—N3—C11—C12	−174.9 (4)
C2—N1—N2—C4	178.1 (5)	O4—C11—C12—C13	2.1 (6)
V1—N1—N2—C4	0.3 (5)	N3—C11—C12—C13	179.9 (3)
C11—N3—N4—V1	−4.0 (6)	O4—C11—C12—C17	−174.7 (4)
O5—V1—N4—N3	179.5 (4)	N3—C11—C12—C17	3.1 (5)
O1—V1—N4—N3	−82.7 (4)	C17—C12—C13—C14	0.0
O3—V1—N4—N3	80.5 (4)	C11—C12—C13—C14	−176.9 (3)
N1—V1—N4—N3	−8.6 (7)	C12—C13—C14—C15	0.0
O4—V1—N4—N3	2.5 (4)	C13—C14—C15—C16	0.0
V1—O1—C1—O2	167.7 (4)	C13—C14—C15—Cl2	177.6 (3)
V1—O1—C1—C2	−11.3 (6)	C14—C15—C16—C17	0.0
N2—N1—C2—C3	−3.4 (8)	Cl2—C15—C16—C17	−177.6 (3)
V1—N1—C2—C3	174.5 (4)	C15—C16—C17—C12	0.0
N2—N1—C2—C1	177.9 (4)	C13—C12—C17—C16	0.0
V1—N1—C2—C1	−4.3 (6)	C11—C12—C17—C16	176.8 (3)
O2—C1—C2—N1	−169.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.88	1.92	2.744 (5)	156
N4—H4···O1ⁱ	0.88	2.14	2.840 (5)	136

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

Experimental details

Crystal data
Chemical formula	[V(C₇H₆ClN₂O)(C₁₀H₇ClN₂O₃)O]
M_r	475.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	119
a, b, c (Å)	26.628 (2), 5.7109 (3), 24.772 (1)
β (°)	100.396 (3)
V (Å³)	3705.2 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.40 × 0.04 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.724, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	11303, 4189, 2154
R_int	0.174
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.175, 0.97
No. of reflections	4189
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.40, −1.20

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

Selected bond lengths (Å) top

V1—N1	2.064 (4)	V1—O3	1.989 (3)
V1—N4	1.888 (4)	V1—O4	2.207 (4)
V1—O1	1.988 (4)	V1—O5	1.593 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱ	0.88	1.92	2.744 (5)	156
N4—H4···O1ⁱ	0.88	2.14	2.840 (5)	136

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

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Wong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m422. Web of Science CSD CrossRef IUCr Journals Google Scholar

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