[3-Chloro-N′-(2-oxidonaphthalen-1-yl­methylidene)benzohydrazidato]methanol(methanolato)oxidovanadium(V)

Wang, F.-M.

doi:10.1107/S1600536811032703

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1254

doi:10.1107/S1600536811032703

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[3-Chloro-N′-(2-oxidonaphthalen-1-ylmethylidene)benzohydrazidato]methanol(methanolato)oxidovanadium(V)

Fu-Ming Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: wfm99999@126.com

(Received 4 August 2011; accepted 12 August 2011; online 17 August 2011)

In the title complex, [V(C₁₈H₁₁ClN₂O₂)(CH₃O)O(CH₃OH)], the V^V ion is coordinated by a tridendate 3-chloro-N′-(2-oxidonaphthalen-1-ylmethylidene)benzohydrazidate ligand, one oxido ligand and by O atoms from a methanol and a methoxide ligand, forming a distorted octahedral geometry. The dihedral angle between the benzene ring and the naphthylene ring system is 6.4 (3)°. The deviation of the V^V ion from the plane defined by the three donor atoms of the tridentate ligand and the methoxy O atom towards the oxido O atom is 0.323 (2) Å. In the crystal, pairs of intermolecular O—H⋯N hydrogen bonds form centrosymmetric dimers.

Related literature

For background to hydrazones and their complexes, see: Seena et al. (2008 ); Bastos et al. (2008 ); Sarkar & Pal (2008 ); Nica et al. (2007 ). For the structure of a related oxidovanadium complex derived from N′-(5-bromo-2-hydroxybenzylidene)-2-chlorobenzohydrazide, see: Wang (2011 ). For other related oxidovanadium(V) complexes, see: Kurup et al. (2010 ); Rajak et al. (2000 ); Grüning et al. (1999 ); Mondal et al. (2009 ).

Experimental

Crystal data

[V(C₁₈H₁₁ClN₂O₂)(CH₃O)O(CH₄O)]
M_r = 452.75
Monoclinic, P 2₁ /n
a = 12.872 (3) Å
b = 7.613 (2) Å
c = 20.695 (3) Å
β = 98.931 (3)°
V = 2003.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan SADABS (Sheldrick, 1996 ) T_min = 0.890, T_max = 0.907
13592 measured reflections
4368 independent reflections
3104 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.109
S = 1.05
4368 reflections
268 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N2ⁱ	0.85 (1)	1.99 (1)	2.839 (3)	178 (4)
Symmetry code: (i) -x, -y, -z+2.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032703/lh5304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032703/lh5304Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds and their oxovanadium complexes have received much attention due to their structural and biological properties (Seena et al., 2008; Bastos et al., 2008; Sarkar & Pal, 2008; Nica et al., 2007). Recently, the author has reported a oxovanadium complex derived from N'-(5-bromo-2-hydroxybenzylidene)-2-chlorobenzohydrazide (Wang, 2011). In this paper, the crystal structure of the title compound is reported.

The V^V ion in the title complex, Fig. 1, is six-coordinated by the phenolic O, imine N, and enolic O atoms of the hydrazone ligand, by one oxo O atom, and by two O atoms respectively from a methanol molecule and a methanolate ligand, forming a distorted octahedral geometry. The dihedral angle between the benzene ring and the naphthylene ring system of the hydrazone ligand is 6.4 (3)°. The deviation of the V atom from the plane defined by the three donor atoms of the hydrazone ligand and the methoxy O atom towards the oxo O atom is 0.323 (2) Å. The bond lengths and angles at the V^V ion are comparable with those observed in similar oxovanadium(V) complexes (Kurup et al., 2010; Rajak et al., 2000; Grüning et al., 1999; Mondal et al., 2009). In the crystal, pairs of intermolecular O—H···N hydrogen bonds form centrosymmetric dimers (Fig. 2).

Related literature top

For background to hydrazone compounds and their complexes, see: Seena et al. (2008); Bastos et al. (2008); Sarkar & Pal (2008); Nica et al. (2007). For the structure of a related oxovanadium complex derived from N'-(5-bromo-2-hydroxybenzylidene)-2-chlorobenzohydrazide, see: Wang (2011). For other related oxovanadium(V) complexes, see: Kurup et al. (2010); Rajak et al. (2000); Grüning et al. (1999); Mondal et al. (2009).

Experimental top

2-Hydroxy-1-naphthaldehyde (1 mmol, 0.17 g), 3-chlorobenzohydrazide 1 mmol, 0.17 g), and VO(acac)₂ (1 mmol, 0.26 g) were mixed in methanol (30 ml). The mixture was boiled under reflux for 2 h, then cooled to room temperature. Brown block-like single crystals, suitable for X-ray diffraction, were formed after slow evaporation of the solution in air for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

[3-Chloro-N'-(2-oxidonaphthalen-1- ylmethylidene)benzohydrazidato]methanol(methanolato)oxidovanadium(V) top

Crystal data top

[V(C₁₈H₁₁ClN₂O₂)(CH₃O)O(CH₄O)]	F(000) = 928
M_r = 452.75	D_x = 1.501 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3491 reflections
a = 12.872 (3) Å	θ = 2.8–26.0°
b = 7.613 (2) Å	µ = 0.66 mm⁻¹
c = 20.695 (3) Å	T = 298 K
β = 98.931 (3)°	Block, brown
V = 2003.4 (8) Å³	0.18 × 0.17 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4368 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scan	θ_max = 27.0°, θ_min = 2.9°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −14→16
T_min = 0.890, T_max = 0.907	k = −9→9
13592 measured reflections	l = −26→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.042P)² + 0.9229P] where P = (F_o² + 2F_c²)/3
4368 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.34 e Å⁻³
1 restraint	Δρ_min = −0.43 e Å⁻³

Crystal data top

[V(C₁₈H₁₁ClN₂O₂)(CH₃O)O(CH₄O)]	V = 2003.4 (8) Å³
M_r = 452.75	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.872 (3) Å	µ = 0.66 mm⁻¹
b = 7.613 (2) Å	T = 298 K
c = 20.695 (3) Å	0.18 × 0.17 × 0.15 mm
β = 98.931 (3)°

Data collection top

Bruker SMART CCD diffractometer	4368 independent reflections
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	3104 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.907	R_int = 0.036
13592 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.34 e Å⁻³
4368 reflections	Δρ_min = −0.43 e Å⁻³
268 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
V1	0.26454 (3)	0.08667 (6)	0.99698 (2)	0.03892 (14)
Cl1	0.15025 (8)	0.45711 (15)	1.28761 (4)	0.0857 (3)
N1	0.10581 (15)	0.1236 (2)	0.95334 (9)	0.0317 (4)
N2	0.04044 (15)	0.2021 (3)	0.99338 (9)	0.0338 (5)
O1	0.26311 (14)	−0.0734 (3)	0.92934 (8)	0.0472 (5)
O2	0.19838 (13)	0.2083 (2)	1.06222 (8)	0.0417 (4)
O3	0.37183 (13)	0.0107 (3)	1.05311 (8)	0.0467 (5)
O4	0.17893 (14)	−0.1470 (3)	1.04327 (9)	0.0469 (5)
O5	0.31027 (15)	0.2518 (3)	0.96509 (10)	0.0601 (5)
C1	0.11838 (18)	0.0029 (3)	0.84704 (11)	0.0328 (5)
C2	0.21637 (19)	−0.0746 (3)	0.86749 (12)	0.0367 (6)
C3	0.2684 (2)	−0.1682 (4)	0.82235 (13)	0.0438 (6)
H3	0.3329	−0.2215	0.8365	0.053*
C4	0.2240 (2)	−0.1799 (4)	0.75880 (13)	0.0451 (7)
H4A	0.2592	−0.2412	0.7299	0.054*
C5	0.1258 (2)	−0.1019 (3)	0.73489 (12)	0.0418 (6)
C6	0.0817 (2)	−0.1125 (4)	0.66811 (13)	0.0547 (8)
H6	0.1183	−0.1709	0.6392	0.066*
C7	−0.0130 (3)	−0.0392 (5)	0.64528 (15)	0.0657 (9)
H7	−0.0405	−0.0465	0.6011	0.079*
C8	−0.0688 (2)	0.0469 (4)	0.68830 (15)	0.0626 (9)
H8	−0.1343	0.0951	0.6727	0.075*
C9	−0.0285 (2)	0.0615 (4)	0.75334 (13)	0.0476 (7)
H9	−0.0670	0.1207	0.7810	0.057*
C10	0.07055 (19)	−0.0116 (3)	0.77942 (11)	0.0360 (6)
C11	0.06312 (18)	0.0867 (3)	0.89423 (11)	0.0331 (5)
H11	−0.0072	0.1158	0.8813	0.040*
C12	0.09845 (18)	0.2435 (3)	1.04907 (11)	0.0332 (5)
C13	0.05144 (19)	0.3322 (3)	1.10122 (11)	0.0345 (5)
C14	0.1116 (2)	0.3473 (3)	1.16256 (12)	0.0403 (6)
H14	0.1790	0.2999	1.1703	0.048*
C15	0.0718 (2)	0.4319 (4)	1.21188 (13)	0.0485 (7)
C16	−0.0294 (2)	0.4999 (4)	1.20174 (14)	0.0525 (7)
H16	−0.0565	0.5546	1.2357	0.063*
C17	−0.0890 (2)	0.4853 (4)	1.14100 (14)	0.0506 (7)
H17	−0.1569	0.5308	1.1339	0.061*
C18	−0.0496 (2)	0.4041 (3)	1.09024 (13)	0.0424 (6)
H18	−0.0902	0.3972	1.0490	0.051*
C19	0.4735 (2)	0.0765 (5)	1.07551 (15)	0.0683 (10)
H19A	0.4918	0.1617	1.0450	0.102*
H19B	0.5232	−0.0183	1.0793	0.102*
H19C	0.4746	0.1308	1.1175	0.102*
C20	0.2289 (3)	−0.3005 (5)	1.0690 (2)	0.0865 (12)
H20A	0.2443	−0.3737	1.0340	0.130*
H20B	0.1835	−0.3626	1.0939	0.130*
H20C	0.2932	−0.2706	1.0970	0.130*
H4	0.1136 (9)	−0.162 (5)	1.0318 (16)	0.086 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0281 (2)	0.0508 (3)	0.0397 (2)	0.0009 (2)	0.01096 (17)	0.0007 (2)
Cl1	0.0987 (7)	0.1131 (8)	0.0431 (4)	0.0125 (6)	0.0045 (4)	−0.0194 (5)
N1	0.0312 (10)	0.0324 (11)	0.0345 (10)	0.0022 (9)	0.0144 (8)	0.0005 (8)
N2	0.0319 (11)	0.0376 (12)	0.0348 (10)	0.0026 (9)	0.0140 (9)	−0.0003 (9)
O1	0.0402 (10)	0.0614 (12)	0.0407 (10)	0.0165 (9)	0.0080 (8)	−0.0048 (9)
O2	0.0298 (9)	0.0546 (12)	0.0417 (9)	−0.0012 (8)	0.0091 (7)	−0.0083 (8)
O3	0.0282 (9)	0.0654 (13)	0.0460 (10)	−0.0008 (9)	0.0045 (8)	−0.0069 (9)
O4	0.0343 (11)	0.0462 (11)	0.0585 (12)	−0.0021 (9)	0.0016 (9)	0.0122 (9)
O5	0.0502 (12)	0.0660 (14)	0.0703 (13)	−0.0063 (11)	0.0291 (10)	0.0096 (11)
C1	0.0322 (13)	0.0325 (13)	0.0359 (12)	−0.0026 (11)	0.0124 (10)	−0.0003 (10)
C2	0.0361 (13)	0.0364 (14)	0.0400 (13)	−0.0006 (11)	0.0131 (11)	−0.0003 (11)
C3	0.0336 (14)	0.0470 (16)	0.0535 (16)	0.0038 (12)	0.0153 (12)	−0.0045 (13)
C4	0.0449 (16)	0.0456 (17)	0.0495 (16)	−0.0048 (13)	0.0225 (13)	−0.0116 (13)
C5	0.0441 (15)	0.0394 (15)	0.0447 (14)	−0.0127 (12)	0.0154 (12)	−0.0065 (12)
C6	0.0572 (19)	0.064 (2)	0.0453 (15)	−0.0155 (16)	0.0163 (14)	−0.0188 (14)
C7	0.061 (2)	0.087 (3)	0.0462 (17)	−0.0128 (19)	−0.0015 (15)	−0.0195 (17)
C8	0.0508 (18)	0.079 (2)	0.0538 (18)	0.0010 (16)	−0.0059 (15)	−0.0124 (16)
C9	0.0415 (15)	0.0559 (18)	0.0446 (15)	0.0002 (13)	0.0039 (12)	−0.0104 (13)
C10	0.0365 (14)	0.0342 (14)	0.0390 (13)	−0.0078 (11)	0.0113 (11)	−0.0027 (11)
C11	0.0285 (12)	0.0347 (13)	0.0372 (12)	−0.0003 (11)	0.0082 (10)	0.0046 (11)
C12	0.0323 (13)	0.0315 (13)	0.0382 (12)	−0.0042 (11)	0.0129 (10)	0.0017 (10)
C13	0.0358 (13)	0.0300 (13)	0.0406 (13)	−0.0053 (11)	0.0142 (11)	−0.0005 (10)
C14	0.0394 (14)	0.0429 (15)	0.0408 (14)	−0.0016 (12)	0.0134 (11)	−0.0005 (11)
C15	0.0587 (18)	0.0502 (18)	0.0392 (14)	−0.0060 (15)	0.0163 (13)	−0.0045 (12)
C16	0.063 (2)	0.0482 (18)	0.0529 (17)	−0.0029 (15)	0.0306 (15)	−0.0096 (14)
C17	0.0446 (16)	0.0410 (16)	0.071 (2)	0.0002 (13)	0.0229 (15)	−0.0087 (14)
C18	0.0435 (15)	0.0377 (15)	0.0474 (15)	−0.0021 (12)	0.0111 (12)	−0.0042 (12)
C19	0.0375 (16)	0.108 (3)	0.0586 (19)	−0.0146 (17)	0.0047 (14)	−0.0152 (19)
C20	0.070 (2)	0.065 (2)	0.111 (3)	−0.0051 (19)	−0.026 (2)	0.032 (2)

Geometric parameters (Å, º) top

V1—O5	1.576 (2)	C6—H6	0.9300
V1—O3	1.7587 (18)	C7—C8	1.392 (4)
V1—O1	1.8539 (18)	C7—H7	0.9300
V1—O2	1.9398 (17)	C8—C9	1.370 (4)
V1—N1	2.120 (2)	C8—H8	0.9300
V1—O4	2.371 (2)	C9—C10	1.419 (4)
Cl1—C15	1.738 (3)	C9—H9	0.9300
N1—C11	1.292 (3)	C11—H11	0.9300
N1—N2	1.403 (3)	C12—C13	1.480 (3)
N2—C12	1.311 (3)	C13—C14	1.385 (3)
O1—C2	1.327 (3)	C13—C18	1.397 (4)
O2—C12	1.301 (3)	C14—C15	1.371 (4)
O3—C19	1.410 (3)	C14—H14	0.9300
O4—C20	1.400 (4)	C15—C16	1.387 (4)
O4—H4	0.845 (10)	C16—C17	1.372 (4)
C1—C2	1.397 (3)	C16—H16	0.9300
C1—C10	1.443 (3)	C17—C18	1.382 (4)
C1—C11	1.443 (3)	C17—H17	0.9300
C2—C3	1.423 (3)	C18—H18	0.9300
C3—C4	1.353 (4)	C19—H19A	0.9600
C3—H3	0.9300	C19—H19B	0.9600
C4—C5	1.415 (4)	C19—H19C	0.9600
C4—H4A	0.9300	C20—H20A	0.9600
C5—C6	1.413 (4)	C20—H20B	0.9600
C5—C10	1.425 (3)	C20—H20C	0.9600
C6—C7	1.357 (4)

O5—V1—O3	103.46 (10)	C9—C8—C7	120.8 (3)
O5—V1—O1	99.70 (10)	C9—C8—H8	119.6
O3—V1—O1	101.38 (8)	C7—C8—H8	119.6
O5—V1—O2	98.26 (9)	C8—C9—C10	121.5 (3)
O3—V1—O2	94.70 (8)	C8—C9—H9	119.2
O1—V1—O2	152.31 (8)	C10—C9—H9	119.2
O5—V1—N1	96.54 (9)	C9—C10—C5	116.9 (2)
O3—V1—N1	158.57 (8)	C9—C10—C1	124.2 (2)
O1—V1—N1	82.51 (8)	C5—C10—C1	118.9 (2)
O2—V1—N1	74.64 (7)	N1—C11—C1	123.7 (2)
O5—V1—O4	174.17 (9)	N1—C11—H11	118.1
O3—V1—O4	81.55 (8)	C1—C11—H11	118.1
O1—V1—O4	82.03 (8)	O2—C12—N2	123.0 (2)
O2—V1—O4	78.18 (8)	O2—C12—C13	116.4 (2)
N1—V1—O4	78.11 (7)	N2—C12—C13	120.6 (2)
C11—N1—N2	116.49 (19)	C14—C13—C18	119.4 (2)
C11—N1—V1	127.92 (16)	C14—C13—C12	118.2 (2)
N2—N1—V1	115.56 (14)	C18—C13—C12	122.4 (2)
C12—N2—N1	108.04 (19)	C15—C14—C13	120.1 (3)
C2—O1—V1	133.04 (16)	C15—C14—H14	120.0
C12—O2—V1	118.64 (15)	C13—C14—H14	120.0
C19—O3—V1	133.9 (2)	C14—C15—C16	120.8 (3)
C20—O4—V1	124.4 (2)	C14—C15—Cl1	119.5 (2)
C20—O4—H4	112 (3)	C16—C15—Cl1	119.7 (2)
V1—O4—H4	119 (2)	C17—C16—C15	119.2 (3)
C2—C1—C10	119.4 (2)	C17—C16—H16	120.4
C2—C1—C11	119.9 (2)	C15—C16—H16	120.4
C10—C1—C11	120.6 (2)	C16—C17—C18	120.9 (3)
O1—C2—C1	122.8 (2)	C16—C17—H17	119.5
O1—C2—C3	116.6 (2)	C18—C17—H17	119.5
C1—C2—C3	120.5 (2)	C17—C18—C13	119.6 (3)
C4—C3—C2	120.1 (2)	C17—C18—H18	120.2
C4—C3—H3	120.0	C13—C18—H18	120.2
C2—C3—H3	120.0	O3—C19—H19A	109.5
C3—C4—C5	122.1 (2)	O3—C19—H19B	109.5
C3—C4—H4A	118.9	H19A—C19—H19B	109.5
C5—C4—H4A	118.9	O3—C19—H19C	109.5
C6—C5—C4	121.3 (2)	H19A—C19—H19C	109.5
C6—C5—C10	119.7 (3)	H19B—C19—H19C	109.5
C4—C5—C10	119.0 (2)	O4—C20—H20A	109.5
C7—C6—C5	121.3 (3)	O4—C20—H20B	109.5
C7—C6—H6	119.3	H20A—C20—H20B	109.5
C5—C6—H6	119.3	O4—C20—H20C	109.5
C6—C7—C8	119.7 (3)	H20A—C20—H20C	109.5
C6—C7—H7	120.1	H20B—C20—H20C	109.5
C8—C7—H7	120.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N2ⁱ	0.85 (1)	1.99 (1)	2.839 (3)	178 (4)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[V(C₁₈H₁₁ClN₂O₂)(CH₃O)O(CH₄O)]
M_r	452.75
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.872 (3), 7.613 (2), 20.695 (3)
β (°)	98.931 (3)
V (Å³)	2003.4 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.18 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan SADABS (Sheldrick, 1996)
T_min, T_max	0.890, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	13592, 4368, 3104
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.05
No. of reflections	4368
No. of parameters	268
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.43

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N2ⁱ	0.845 (10)	1.994 (11)	2.839 (3)	178 (4)

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

This work was supported financially by Dezhou University, People's Republic of China.

References

Bastos, A. M. B., da Silva, J. G., Maia, P. I. da S., Deflon, V. M., Batista, A. A., Ferreira, A. V. M., Botion, L. M., Niquet, E. & Beraldo, H. (2008). Polyhedron 27, 1787-1794. Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Grüning, C., Schmidt, H. & Rehder, D. (1999). Inorg. Chem. Commun. 2, 57–59. Google Scholar
Kurup, M. R. P., Seena, E. B. & Kuriakose, M. (2010). Struct. Chem. 21, 599–605. CSD CrossRef CAS Google Scholar
Mondal, B., Drew, M. G. B. & Ghosh, T. (2009). Inorg. Chim. Acta, 362, 3303–3308. CrossRef CAS Google Scholar
Nica, S., Rudolph, M., Görls, H. & Plass, W. (2007). Inorg. Chim. Acta 360, 1743–1752. Google Scholar
Rajak, K. K., Mondal, S. & Rath, S. P. (2000). Polyhedron 19, 931–936. Google Scholar
Sarkar, A. & Pal, S. (2008). Inorg. Chim. Acta, 361, 2296–2304. CrossRef CAS Google Scholar
Seena, E. B., Mathew, N., Kuriakose, M. & Kurup, M. R. P. (2008). Polyhedron 27, 1455–1462. 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
Wang, F.-M. (2011). Acta Cryst. E67, m433–m434. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page m1254

doi:10.1107/S1600536811032703

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[3-Chloro-N′-(2-oxidonaphthalen-1-yl­methyl­idene)benzohydrazidato]methanol(methanolato)oxidovanadium(V)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[3-Chloro-N′-(2-oxidonaphthalen-1-ylmethylidene)benzohydrazidato]methanol(methanolato)oxidovanadium(V)