Methoxo[N'-(3-meth-oxy-2-oxidobenzyl-idene)benzohydrazidato]oxidovanadium(V).

In the title complex, [V(C(15)H(12)N(2)O(4))(CH(3)O)O], the V(V) ion exhibits a distorted square-pyramidal coordination geometry; three donor atoms from a hydrazone ligand and one O atom of the deprotonated methanol define the coordination basal plane. The V(V) ion is displaced by 0.464 (1) Å from the basal plane towards the axial oxide O atom. Intra-molecular O-H⋯N hydrogen bonding occurs. Inter-molecular C-H⋯O hydrogen bonding is also observed in the crystal structure.

Related literature

For general background to hydrazones and their chelation ability, see: Liu & Gao (1998 ▶); Ma et al. (1989 ▶); Sur et al. (1993 ▶); Sun et al. (2005 ▶). For related structures, see: Chen et al. (2004 ▶); Liu et al. (2006 ▶); Ghosh et al. (2007 ▶); Seena et al. (2008 ▶). For the synthesis, see: Gao et al. (1998 ▶); Chen (2008 ▶).

Experimental

Crystal data

[V(C15H12N2O4)(CH3O)O]

M = 382.24

Monoclinic,

a = 16.194 (3) Å

b = 6.6746 (13) Å

c = 15.359 (3) Å

β = 96.89 (3)°

V = 1648.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 293 K

0.39 × 0.22 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ▶) T min = 0.845, T max = 0.909

14918 measured reflections

3686 independent reflections

2776 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.08

3686 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.39 e Å−3

Data collection: TEXRAY (Molecular Structure Corporation, 1999 ▶); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009608/xu2731sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009608/xu2731Isup2.hkl

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

[V(C15H12N2O4)(CH3O)O]	F(000) = 784
Mr = 382.24	Dx = 1.541 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2776 reflections
a = 16.194 (3) Å	θ = 3.1–27.5°
b = 6.6746 (13) Å	µ = 0.64 mm−1
c = 15.359 (3) Å	T = 293 K
β = 96.89 (3)°	Prism, dark-red
V = 1648.1 (6) Å3	0.39 × 0.22 × 0.15 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3686 independent reflections
Radiation source: fine-focus sealed tube	2776 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −21→21
Tmin = 0.845, Tmax = 0.909	k = −8→8
14918 measured reflections	l = −19→19

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) = 0.118	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.062P)2 + 0.2985P] where P = (Fo2 + 2Fc2)/3
3686 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.39 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 > σ(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	0.16311 (2)	0.04276 (6)	0.66648 (3)	0.04096 (14)
O1	0.16555 (9)	0.2270 (2)	0.57877 (11)	0.0533 (4)
O2	0.09673 (11)	0.5226 (3)	0.48044 (13)	0.0624 (5)
O3	0.21107 (9)	−0.1967 (2)	0.72412 (10)	0.0464 (4)
O4	0.46575 (11)	−0.2270 (3)	0.81503 (15)	0.0860 (7)
H4B	0.4400	−0.1379	0.7867	0.129*
O5	0.13675 (10)	0.1611 (3)	0.74736 (12)	0.0599 (5)
O6	0.07767 (10)	−0.0955 (3)	0.62167 (11)	0.0561 (4)
N1	0.29210 (10)	0.0886 (3)	0.68123 (11)	0.0377 (4)
N2	0.33889 (10)	−0.0525 (3)	0.73138 (12)	0.0411 (4)
C1	0.21307 (13)	0.3854 (3)	0.56461 (14)	0.0432 (5)
C2	0.29647 (12)	0.3942 (3)	0.59948 (13)	0.0390 (5)
C3	0.34579 (14)	0.5570 (3)	0.57913 (16)	0.0487 (6)
H3A	0.4017	0.5617	0.6015	0.058*
C4	0.31173 (16)	0.7083 (4)	0.52658 (16)	0.0562 (6)
H4A	0.3445	0.8155	0.5129	0.067*
C5	0.22816 (16)	0.7015 (4)	0.49361 (16)	0.0554 (6)
H5A	0.2052	0.8063	0.4588	0.066*
C6	0.17849 (14)	0.5428 (4)	0.51131 (15)	0.0488 (5)
C7	0.05967 (18)	0.6762 (5)	0.4246 (2)	0.0739 (8)
H7A	0.0016	0.6478	0.4095	0.111*
H7B	0.0865	0.6818	0.3722	0.111*
H7C	0.0659	0.8027	0.4544	0.111*
C8	0.33318 (12)	0.2369 (3)	0.65380 (14)	0.0406 (5)
H8A	0.3903	0.2414	0.6705	0.049*
C9	0.29058 (12)	−0.1970 (3)	0.75157 (14)	0.0397 (5)
C10	0.32708 (14)	−0.3646 (3)	0.80484 (14)	0.0431 (5)
C11	0.41233 (15)	−0.3729 (4)	0.83309 (17)	0.0577 (6)
C12	0.44452 (19)	−0.5360 (5)	0.8821 (2)	0.0744 (9)
H12A	0.5014	−0.5432	0.9001	0.089*
C13	0.3936 (2)	−0.6854 (5)	0.90395 (19)	0.0723 (8)
H13A	0.4162	−0.7932	0.9370	0.087*
C14	0.3096 (2)	−0.6792 (4)	0.87791 (17)	0.0642 (7)
H14A	0.2753	−0.7815	0.8937	0.077*
C15	0.27640 (16)	−0.5201 (4)	0.82817 (16)	0.0508 (6)
H15A	0.2195	−0.5164	0.8099	0.061*
C16	0.00782 (18)	−0.1796 (5)	0.6540 (2)	0.0879 (10)
H16A	−0.0371	−0.1897	0.6073	0.132*
H16B	−0.0088	−0.0958	0.6997	0.132*
H16C	0.0216	−0.3106	0.6771	0.132*

	U11	U22	U33	U12	U13	U23
V1	0.02696 (19)	0.0439 (2)	0.0521 (2)	−0.00458 (14)	0.00533 (14)	0.00005 (17)
O1	0.0359 (8)	0.0547 (10)	0.0670 (10)	−0.0086 (7)	−0.0028 (7)	0.0155 (9)
O2	0.0453 (9)	0.0705 (11)	0.0685 (11)	−0.0006 (8)	−0.0056 (8)	0.0233 (10)
O3	0.0364 (8)	0.0468 (9)	0.0555 (9)	−0.0077 (6)	0.0038 (6)	0.0039 (8)
O4	0.0380 (9)	0.0995 (15)	0.1183 (17)	0.0049 (10)	0.0011 (10)	0.0564 (14)
O5	0.0471 (9)	0.0652 (11)	0.0693 (11)	0.0029 (8)	0.0147 (8)	−0.0103 (9)
O6	0.0390 (8)	0.0612 (10)	0.0664 (11)	−0.0148 (7)	−0.0006 (7)	0.0052 (9)
N1	0.0290 (8)	0.0415 (9)	0.0428 (9)	−0.0003 (7)	0.0047 (7)	−0.0014 (8)
N2	0.0316 (8)	0.0416 (10)	0.0498 (10)	0.0015 (7)	0.0034 (7)	0.0016 (8)
C1	0.0384 (11)	0.0482 (12)	0.0440 (12)	−0.0035 (9)	0.0093 (9)	0.0036 (10)
C2	0.0353 (10)	0.0434 (11)	0.0395 (11)	−0.0033 (8)	0.0093 (8)	−0.0034 (10)
C3	0.0429 (12)	0.0551 (14)	0.0493 (13)	−0.0115 (10)	0.0105 (10)	0.0000 (11)
C4	0.0586 (15)	0.0576 (15)	0.0542 (14)	−0.0149 (12)	0.0146 (11)	0.0099 (13)
C5	0.0616 (15)	0.0556 (15)	0.0497 (13)	−0.0044 (12)	0.0096 (11)	0.0153 (12)
C6	0.0451 (12)	0.0575 (14)	0.0440 (12)	0.0000 (10)	0.0063 (10)	0.0059 (11)
C7	0.0635 (17)	0.083 (2)	0.0713 (18)	0.0100 (15)	−0.0089 (14)	0.0247 (17)
C8	0.0290 (9)	0.0464 (12)	0.0469 (12)	−0.0031 (8)	0.0069 (8)	−0.0045 (10)
C9	0.0355 (10)	0.0433 (11)	0.0407 (11)	0.0005 (9)	0.0067 (8)	−0.0054 (10)
C10	0.0500 (12)	0.0418 (12)	0.0392 (11)	0.0033 (9)	0.0115 (9)	−0.0041 (10)
C11	0.0471 (13)	0.0680 (16)	0.0588 (15)	0.0118 (12)	0.0101 (11)	0.0116 (14)
C12	0.0619 (17)	0.085 (2)	0.077 (2)	0.0244 (16)	0.0101 (15)	0.0246 (17)
C13	0.095 (2)	0.0673 (19)	0.0561 (16)	0.0218 (17)	0.0154 (15)	0.0142 (15)
C14	0.098 (2)	0.0459 (14)	0.0519 (15)	−0.0048 (14)	0.0225 (14)	0.0012 (13)
C15	0.0631 (15)	0.0473 (13)	0.0436 (12)	−0.0025 (11)	0.0127 (11)	−0.0072 (11)
C16	0.0597 (17)	0.101 (2)	0.103 (2)	−0.0432 (17)	0.0113 (16)	0.004 (2)

V1—O1	1.8277 (17)	C4—H4A	0.9300
V1—O3	1.9436 (16)	C5—C6	1.377 (3)
V1—O5	1.5736 (18)	C5—H5A	0.9300
V1—O6	1.7351 (16)	C7—H7A	0.9600
V1—N1	2.0963 (17)	C7—H7B	0.9600
O1—C1	1.341 (3)	C7—H7C	0.9600
O2—C6	1.358 (3)	C8—H8A	0.9300
O2—C7	1.423 (3)	C9—C10	1.467 (3)
O3—C9	1.306 (2)	C10—C15	1.397 (3)
O4—C11	1.353 (3)	C10—C11	1.398 (3)
O4—H4B	0.8200	C11—C12	1.389 (4)
O6—C16	1.406 (3)	C12—C13	1.361 (4)
N1—C8	1.292 (3)	C12—H12A	0.9300
N1—N2	1.384 (2)	C13—C14	1.372 (4)
N2—C9	1.303 (3)	C13—H13A	0.9300
C1—C2	1.393 (3)	C14—C15	1.379 (4)
C1—C6	1.406 (3)	C14—H14A	0.9300
C2—C3	1.405 (3)	C15—H15A	0.9300
C2—C8	1.426 (3)	C16—H16A	0.9600
C3—C4	1.367 (3)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
C4—C5	1.388 (3)
O5—V1—O6	107.53 (9)	O2—C7—H7A	109.5
O5—V1—O1	106.03 (9)	O2—C7—H7B	109.5
O6—V1—O1	98.75 (8)	H7A—C7—H7B	109.5
O5—V1—O3	100.64 (8)	O2—C7—H7C	109.5
O6—V1—O3	89.96 (7)	H7A—C7—H7C	109.5
O1—V1—O3	147.80 (7)	H7B—C7—H7C	109.5
O5—V1—N1	101.68 (8)	N1—C8—C2	124.10 (18)
O6—V1—N1	149.00 (8)	N1—C8—H8A	118.0
O1—V1—N1	82.66 (7)	C2—C8—H8A	118.0
O3—V1—N1	74.46 (6)	N2—C9—O3	121.3 (2)
C1—O1—V1	135.54 (14)	N2—C9—C10	118.93 (19)
C6—O2—C7	117.5 (2)	O3—C9—C10	119.78 (19)
C9—O3—V1	118.22 (14)	C15—C10—C11	118.7 (2)
C11—O4—H4B	109.5	C15—C10—C9	120.0 (2)
C16—O6—V1	135.18 (19)	C11—C10—C9	121.3 (2)
C8—N1—N2	115.74 (16)	O4—C11—C12	117.9 (2)
C8—N1—V1	128.47 (14)	O4—C11—C10	122.7 (2)
N2—N1—V1	115.67 (12)	C12—C11—C10	119.5 (3)
C9—N2—N1	109.38 (16)	C13—C12—C11	120.6 (3)
O1—C1—C2	121.3 (2)	C13—C12—H12A	119.7
O1—C1—C6	119.17 (19)	C11—C12—H12A	119.7
C2—C1—C6	119.5 (2)	C12—C13—C14	121.0 (3)
C1—C2—C3	119.8 (2)	C12—C13—H13A	119.5
C1—C2—C8	120.72 (19)	C14—C13—H13A	119.5
C3—C2—C8	119.42 (19)	C13—C14—C15	119.4 (3)
C4—C3—C2	120.2 (2)	C13—C14—H14A	120.3
C4—C3—H3A	119.9	C15—C14—H14A	120.3
C2—C3—H3A	119.9	C14—C15—C10	120.8 (3)
C3—C4—C5	119.9 (2)	C14—C15—H15A	119.6
C3—C4—H4A	120.1	C10—C15—H15A	119.6
C5—C4—H4A	120.1	O6—C16—H16A	109.5
C6—C5—C4	121.4 (2)	O6—C16—H16B	109.5
C6—C5—H5A	119.3	H16A—C16—H16B	109.5
C4—C5—H5A	119.3	O6—C16—H16C	109.5
O2—C6—C5	125.1 (2)	H16A—C16—H16C	109.5
O2—C6—C1	115.6 (2)	H16B—C16—H16C	109.5
C5—C6—C1	119.2 (2)
O5—V1—O1—C1	68.2 (2)	C7—O2—C6—C5	0.8 (4)
O6—V1—O1—C1	179.4 (2)	C7—O2—C6—C1	−178.6 (2)
O3—V1—O1—C1	−76.5 (3)	C4—C5—C6—O2	−178.7 (2)
N1—V1—O1—C1	−31.9 (2)	C4—C5—C6—C1	0.6 (4)
O5—V1—O3—C9	−90.59 (16)	O1—C1—C6—O2	2.2 (3)
O6—V1—O3—C9	161.58 (15)	C2—C1—C6—O2	−179.7 (2)
O1—V1—O3—C9	55.0 (2)	O1—C1—C6—C5	−177.2 (2)
N1—V1—O3—C9	8.72 (14)	C2—C1—C6—C5	0.9 (3)
O5—V1—O6—C16	−27.1 (3)	N2—N1—C8—C2	178.26 (18)
O1—V1—O6—C16	−137.1 (3)	V1—N1—C8—C2	−6.0 (3)
O3—V1—O6—C16	74.0 (3)	C1—C2—C8—N1	−6.8 (3)
N1—V1—O6—C16	132.6 (3)	C3—C2—C8—N1	174.9 (2)
O5—V1—N1—C8	−85.9 (2)	N1—N2—C9—O3	1.1 (3)
O6—V1—N1—C8	113.8 (2)	N1—N2—C9—C10	179.94 (17)
O1—V1—N1—C8	18.99 (19)	V1—O3—C9—N2	−8.7 (3)
O3—V1—N1—C8	176.1 (2)	V1—O3—C9—C10	172.45 (14)
O5—V1—N1—N2	89.78 (15)	N2—C9—C10—C15	179.3 (2)
O6—V1—N1—N2	−70.5 (2)	O3—C9—C10—C15	−1.9 (3)
O1—V1—N1—N2	−165.29 (15)	N2—C9—C10—C11	−0.8 (3)
O3—V1—N1—N2	−8.15 (13)	O3—C9—C10—C11	178.0 (2)
C8—N1—N2—C9	−177.45 (19)	C15—C10—C11—O4	−178.7 (3)
V1—N1—N2—C9	6.3 (2)	C9—C10—C11—O4	1.5 (4)
V1—O1—C1—C2	29.7 (3)	C15—C10—C11—C12	1.0 (4)
V1—O1—C1—C6	−152.29 (18)	C9—C10—C11—C12	−178.9 (2)
O1—C1—C2—C3	176.2 (2)	O4—C11—C12—C13	178.6 (3)
C6—C1—C2—C3	−1.8 (3)	C10—C11—C12—C13	−1.1 (5)
O1—C1—C2—C8	−2.0 (3)	C11—C12—C13—C14	0.3 (5)
C6—C1—C2—C8	180.0 (2)	C12—C13—C14—C15	0.6 (4)
C1—C2—C3—C4	1.2 (3)	C13—C14—C15—C10	−0.7 (4)
C8—C2—C3—C4	179.5 (2)	C11—C10—C15—C14	−0.1 (3)
C2—C3—C4—C5	0.3 (4)	C9—C10—C15—C14	179.7 (2)
C3—C4—C5—C6	−1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N2	0.82	1.84	2.568 (2)	147
C8—H8A···O4i	0.93	2.32	3.243 (3)	169

Table 1

Selected bond lengths (Å)

V1—O1	1.8277 (17)
V1—O3	1.9436 (16)
V1—O5	1.5736 (18)
V1—O6	1.7351 (16)
V1—N1	2.0963 (17)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯N2	0.82	1.84	2.568 (2)	147
C8—H8A⋯O4i	0.93	2.32	3.243 (3)	169

Symmetry code: (i) .