[3-Chloro-N'-(2-oxidonaphthalen-1-yl-methylidene)benzohydrazidato]methanol(methanolato)oxidovanadium(V).

In the title complex, [V(C(18)H(11)ClN(2)O(2))(CH(3)O)O(CH(3)OH)], 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 octa-hedral geometry. The dihedral angle between the benzene ring and the naphthyl-ene 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 meth-oxy O atom towards the oxido O atom is 0.323 (2) Å. In the crystal, pairs of inter-molecular 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 = 452.75

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.05

4368 reflections

268 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.43 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032703/lh5304sup1.cif

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

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

[V(C18H11ClN2O2)(CH3O)O(CH4O)]	F(000) = 928
Mr = 452.75	Dx = 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

Bruker SMART CCD diffractometer	4368 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scan	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −14→16
Tmin = 0.890, Tmax = 0.907	k = −9→9
13592 measured reflections	l = −26→26

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(Fo2) + (0.042P)2 + 0.9229P] where P = (Fo2 + 2Fc2)/3
4368 reflections	(Δ/σ)max < 0.001
268 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.43 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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)

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) .