(Ethano-lato-κO)[N'-(3-meth-oxy-2-oxidobenzyl-idene-κO(2))benzo-hydrazidato-κ(2)N',O]oxidovanadium(V).

In the title complex, [V(C(15)H(12)N(2)O(4))(C(2)H(5)O)O], the V(V) ion is coordinated by an oxide O atom, an ethano-late anion and two O atoms and one N atom from the tridentate benzo-hydrazidate dianion in a distorted square-pyramidal geometry; the V atom is displaced by 0.4748 (8) Å from the basal plane towards the axial oxide O atom. An intra-molecular O-H⋯N hydrogen bond occurs in the benzohydrazidate ligand. Weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal.

Related literature

For general background to the coordination chemistry and biochemisty of vanadium, see: Deng et al. (2007 ▶); Monfared et al. (2011 ▶); Sutradhar et al. (2006 ▶). 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 ▶); Huang et al. (2010 ▶).

Experimental

Crystal data

[V(C15H12N2O4)(n class="Chemical">C2H5O)O]

M = 396.27

Monoclinic,

a = 15.808 (5) Å

b = 6.606 (2) Å

c = 16.693 (8) Å

β = 94.107 (16)°

V = 1738.6 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.61 mm−1

T = 293 K

0.37 × 0.25 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ▶) T min = 0.834, T max = 0.924

15371 measured reflections

3968 independent reflections

3243 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.08

3968 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.22 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 datablock(s) I, global. DOI: 10.1107/S1600536812032229/xu5587sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032229/xu5587Isup2.hkl

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

[V(C15H12N2O4)(C2H5O)O]	F(000) = 816
Mr = 396.27	Dx = 1.514 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3243 reflections
a = 15.808 (5) Å	θ = 3.3–27.5°
b = 6.606 (2) Å	µ = 0.61 mm−1
c = 16.693 (8) Å	T = 293 K
β = 94.107 (16)°	Prism, dark-red
V = 1738.6 (12) Å3	0.37 × 0.25 × 0.13 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3968 independent reflections
Radiation source: fine-focus sealed tube	3243 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −19→20
Tmin = 0.834, Tmax = 0.924	k = −8→7
15371 measured reflections	l = −21→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0564P)2 + 0.3657P] where P = (Fo2 + 2Fc2)/3
3968 reflections	(Δ/σ)max = 0.001
237 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.327165 (17)	0.03858 (5)	0.379657 (17)	0.03227 (11)
O1	0.30812 (8)	0.2237 (2)	0.45811 (8)	0.0442 (3)
O2	0.35894 (10)	0.5229 (2)	0.55498 (9)	0.0496 (4)
O3	0.28941 (8)	−0.2038 (2)	0.32138 (8)	0.0407 (3)
O4	0.04552 (9)	−0.2451 (3)	0.20545 (12)	0.0782 (6)
H4B	0.0647	−0.1583	0.2368	0.117*
O5	0.36775 (9)	0.1609 (2)	0.31098 (9)	0.0516 (4)
O6	0.40591 (8)	−0.1056 (2)	0.43088 (8)	0.0435 (3)
N1	0.19698 (9)	0.0812 (2)	0.34927 (8)	0.0328 (3)
N2	0.15908 (9)	−0.0609 (2)	0.29735 (9)	0.0372 (4)
C1	0.25579 (11)	0.3816 (3)	0.46463 (10)	0.0357 (4)
C2	0.17609 (11)	0.3877 (3)	0.42268 (10)	0.0358 (4)
C3	0.12022 (13)	0.5497 (3)	0.43503 (12)	0.0472 (5)
H3A	0.0668	0.5530	0.4077	0.057*
C4	0.14474 (15)	0.7014 (4)	0.48709 (13)	0.0546 (6)
H4A	0.1078	0.8079	0.4952	0.065*
C5	0.22441 (14)	0.6982 (3)	0.52816 (12)	0.0488 (5)
H5A	0.2402	0.8029	0.5633	0.059*
C6	0.28039 (13)	0.5414 (3)	0.51739 (11)	0.0394 (4)
C7	0.38639 (16)	0.6801 (4)	0.60921 (14)	0.0617 (6)
H7A	0.4451	0.6602	0.6263	0.092*
H7B	0.3531	0.6772	0.6551	0.092*
H7C	0.3795	0.8087	0.5828	0.092*
C8	0.14914 (11)	0.2298 (3)	0.36837 (11)	0.0366 (4)
H8A	0.0938	0.2341	0.3453	0.044*
C9	0.21338 (11)	−0.2052 (3)	0.28567 (10)	0.0342 (4)
C10	0.18783 (11)	−0.3739 (3)	0.23241 (10)	0.0353 (4)
C11	0.10557 (12)	−0.3869 (4)	0.19530 (13)	0.0471 (5)
C12	0.08370 (15)	−0.5527 (4)	0.14672 (14)	0.0570 (6)
H12A	0.0287	−0.5640	0.1234	0.068*
C13	0.14231 (15)	−0.6997 (4)	0.13284 (13)	0.0541 (5)
H13A	0.1269	−0.8090	0.0998	0.065*
C14	0.22383 (15)	−0.6862 (3)	0.16759 (13)	0.0509 (5)
H14A	0.2636	−0.7851	0.1575	0.061*
C15	0.24613 (13)	−0.5261 (3)	0.21720 (11)	0.0409 (4)
H15A	0.3010	−0.5186	0.2411	0.049*
C16	0.47854 (16)	−0.2211 (5)	0.41625 (15)	0.0726 (8)
H16A	0.4651	−0.3632	0.4225	0.087*
H16B	0.5233	−0.1876	0.4569	0.087*
C17	0.51099 (16)	−0.1928 (5)	0.33759 (16)	0.0734 (8)
H17A	0.5644	−0.2613	0.3359	0.110*
H17B	0.5186	−0.0510	0.3279	0.110*
H17C	0.4713	−0.2476	0.2970	0.110*

	U11	U22	U33	U12	U13	U23
V1	0.02768 (17)	0.03613 (19)	0.03235 (17)	0.00497 (12)	−0.00236 (11)	−0.00102 (12)
O1	0.0396 (7)	0.0454 (8)	0.0458 (7)	0.0120 (6)	−0.0079 (5)	−0.0127 (6)
O2	0.0487 (8)	0.0503 (8)	0.0481 (8)	0.0044 (7)	−0.0073 (6)	−0.0160 (7)
O3	0.0343 (7)	0.0413 (7)	0.0453 (7)	0.0066 (6)	−0.0066 (5)	−0.0083 (6)
O4	0.0364 (8)	0.0960 (14)	0.0991 (14)	0.0110 (9)	−0.0166 (8)	−0.0531 (11)
O5	0.0450 (8)	0.0587 (10)	0.0510 (8)	0.0002 (7)	0.0032 (6)	0.0117 (7)
O6	0.0391 (7)	0.0507 (8)	0.0391 (7)	0.0148 (6)	−0.0069 (5)	−0.0039 (6)
N1	0.0296 (7)	0.0363 (8)	0.0319 (7)	0.0023 (6)	−0.0013 (6)	−0.0012 (6)
N2	0.0315 (8)	0.0398 (9)	0.0393 (8)	0.0004 (7)	−0.0037 (6)	−0.0058 (7)
C1	0.0397 (9)	0.0352 (9)	0.0327 (9)	0.0047 (8)	0.0053 (7)	−0.0010 (7)
C2	0.0365 (9)	0.0382 (10)	0.0329 (9)	0.0065 (8)	0.0047 (7)	0.0011 (7)
C3	0.0441 (11)	0.0514 (13)	0.0454 (11)	0.0150 (9)	−0.0011 (9)	−0.0037 (9)
C4	0.0640 (14)	0.0497 (13)	0.0499 (12)	0.0238 (11)	0.0034 (10)	−0.0062 (10)
C5	0.0661 (13)	0.0419 (11)	0.0384 (10)	0.0080 (10)	0.0030 (9)	−0.0084 (9)
C6	0.0464 (11)	0.0398 (10)	0.0319 (9)	0.0032 (8)	0.0024 (7)	−0.0022 (8)
C7	0.0697 (15)	0.0599 (15)	0.0529 (13)	0.0004 (12)	−0.0131 (11)	−0.0198 (11)
C8	0.0298 (8)	0.0419 (10)	0.0376 (9)	0.0043 (8)	−0.0002 (7)	0.0021 (8)
C9	0.0347 (9)	0.0370 (10)	0.0306 (8)	0.0002 (8)	0.0003 (7)	0.0020 (7)
C10	0.0381 (9)	0.0386 (10)	0.0294 (8)	−0.0028 (8)	0.0037 (7)	0.0005 (7)
C11	0.0383 (10)	0.0558 (12)	0.0471 (11)	−0.0018 (9)	0.0030 (8)	−0.0124 (10)
C12	0.0467 (12)	0.0691 (16)	0.0548 (13)	−0.0144 (11)	0.0012 (10)	−0.0193 (11)
C13	0.0692 (15)	0.0495 (13)	0.0442 (11)	−0.0149 (11)	0.0076 (10)	−0.0117 (9)
C14	0.0667 (14)	0.0398 (11)	0.0464 (11)	0.0052 (10)	0.0061 (10)	−0.0048 (9)
C15	0.0467 (11)	0.0382 (10)	0.0376 (10)	0.0027 (8)	0.0008 (8)	0.0014 (8)
C16	0.0608 (15)	0.094 (2)	0.0636 (15)	0.0445 (15)	0.0118 (12)	0.0132 (14)
C17	0.0587 (15)	0.087 (2)	0.0769 (18)	0.0242 (14)	0.0189 (13)	0.0034 (15)

V1—N1	2.1029 (15)	C5—C6	1.382 (3)
V1—O1	1.8325 (14)	C5—H5A	0.9300
V1—O3	1.9453 (14)	C7—H7A	0.9600
V1—O5	1.5762 (15)	C7—H7B	0.9600
V1—O6	1.7423 (13)	C7—H7C	0.9600
O1—C1	1.340 (2)	C8—H8A	0.9300
O2—C6	1.356 (2)	C9—C10	1.464 (3)
O2—C7	1.424 (3)	C10—C15	1.399 (3)
O3—C9	1.303 (2)	C10—C11	1.402 (3)
O4—C11	1.353 (3)	C11—C12	1.391 (3)
O4—H4B	0.8200	C12—C13	1.373 (3)
O6—C16	1.414 (2)	C12—H12A	0.9300
N1—C8	1.293 (2)	C13—C14	1.378 (3)
N1—N2	1.385 (2)	C13—H13A	0.9300
N2—C9	1.307 (2)	C14—C15	1.374 (3)
C1—C2	1.397 (3)	C14—H14A	0.9300
C1—C6	1.411 (3)	C15—H15A	0.9300
C2—C3	1.412 (3)	C16—C17	1.456 (3)
C2—C8	1.427 (3)	C16—H16A	0.9700
C3—C4	1.364 (3)	C16—H16B	0.9700
C3—H3A	0.9300	C17—H17A	0.9600
C4—C5	1.390 (3)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
O5—V1—O6	108.88 (8)	O2—C7—H7C	109.5
O5—V1—O1	105.89 (9)	H7A—C7—H7C	109.5
O6—V1—O1	99.34 (7)	H7B—C7—H7C	109.5
O5—V1—O3	100.64 (8)	N1—C8—C2	123.93 (16)
O6—V1—O3	88.75 (6)	N1—C8—H8A	118.0
O1—V1—O3	147.85 (6)	C2—C8—H8A	118.0
O5—V1—N1	101.43 (7)	O3—C9—N2	121.40 (17)
O6—V1—N1	147.57 (7)	O3—C9—C10	119.24 (16)
O1—V1—N1	82.81 (6)	N2—C9—C10	119.35 (16)
O3—V1—N1	74.32 (6)	C15—C10—C11	118.54 (18)
C1—O1—V1	135.34 (12)	C15—C10—C9	120.02 (17)
C6—O2—C7	117.11 (17)	C11—C10—C9	121.44 (17)
C9—O3—V1	118.32 (12)	O4—C11—C12	118.07 (19)
C11—O4—H4B	109.5	O4—C11—C10	122.61 (19)
C16—O6—V1	140.40 (14)	C12—C11—C10	119.3 (2)
C8—N1—N2	115.75 (15)	C13—C12—C11	120.8 (2)
C8—N1—V1	128.45 (12)	C13—C12—H12A	119.6
N2—N1—V1	115.61 (11)	C11—C12—H12A	119.6
C9—N2—N1	109.18 (14)	C12—C13—C14	120.3 (2)
O1—C1—C2	121.40 (17)	C12—C13—H13A	119.8
O1—C1—C6	119.24 (17)	C14—C13—H13A	119.8
C2—C1—C6	119.32 (17)	C15—C14—C13	119.7 (2)
C1—C2—C3	119.96 (18)	C15—C14—H14A	120.1
C1—C2—C8	121.00 (17)	C13—C14—H14A	120.1
C3—C2—C8	119.03 (17)	C14—C15—C10	121.2 (2)
C4—C3—C2	119.83 (19)	C14—C15—H15A	119.4
C4—C3—H3A	120.1	C10—C15—H15A	119.4
C2—C3—H3A	120.1	O6—C16—C17	115.4 (2)
C3—C4—C5	120.60 (19)	O6—C16—H16A	108.4
C3—C4—H4A	119.7	C17—C16—H16A	108.4
C5—C4—H4A	119.7	O6—C16—H16B	108.4
C6—C5—C4	120.9 (2)	C17—C16—H16B	108.4
C6—C5—H5A	119.6	H16A—C16—H16B	107.5
C4—C5—H5A	119.6	C16—C17—H17A	109.5
O2—C6—C5	125.51 (18)	C16—C17—H17B	109.5
O2—C6—C1	115.07 (17)	H17A—C17—H17B	109.5
C5—C6—C1	119.41 (18)	C16—C17—H17C	109.5
O2—C7—H7A	109.5	H17A—C17—H17C	109.5
O2—C7—H7B	109.5	H17B—C17—H17C	109.5
H7A—C7—H7B	109.5
O5—V1—O1—C1	68.39 (19)	C7—O2—C6—C5	−1.0 (3)
O6—V1—O1—C1	−178.79 (18)	C7—O2—C6—C1	−179.65 (19)
O3—V1—O1—C1	−76.1 (2)	C4—C5—C6—O2	−179.3 (2)
N1—V1—O1—C1	−31.50 (18)	C4—C5—C6—C1	−0.7 (3)
O5—V1—O3—C9	−89.56 (14)	O1—C1—C6—O2	2.8 (3)
O6—V1—O3—C9	161.46 (13)	C2—C1—C6—O2	−179.60 (17)
O1—V1—O3—C9	55.77 (18)	O1—C1—C6—C5	−175.88 (18)
N1—V1—O3—C9	9.46 (12)	C2—C1—C6—C5	1.7 (3)
O5—V1—O6—C16	−37.9 (3)	N2—N1—C8—C2	178.23 (17)
O1—V1—O6—C16	−148.3 (3)	V1—N1—C8—C2	−6.9 (3)
O3—V1—O6—C16	63.0 (3)	C1—C2—C8—N1	−5.5 (3)
N1—V1—O6—C16	120.4 (3)	C3—C2—C8—N1	175.82 (19)
O5—V1—N1—C8	−85.71 (17)	V1—O3—C9—N2	−9.5 (2)
O6—V1—N1—C8	115.25 (17)	V1—O3—C9—C10	171.59 (12)
O1—V1—N1—C8	19.13 (16)	N1—N2—C9—O3	1.2 (2)
O3—V1—N1—C8	176.30 (17)	N1—N2—C9—C10	−179.87 (15)
O5—V1—N1—N2	89.16 (14)	O3—C9—C10—C15	−3.2 (3)
O6—V1—N1—N2	−69.88 (17)	N2—C9—C10—C15	177.87 (17)
O1—V1—N1—N2	−166.00 (13)	O3—C9—C10—C11	177.21 (17)
O3—V1—N1—N2	−8.83 (11)	N2—C9—C10—C11	−1.8 (3)
C8—N1—N2—C9	−177.68 (16)	C15—C10—C11—O4	−178.9 (2)
V1—N1—N2—C9	6.78 (18)	C9—C10—C11—O4	0.7 (3)
V1—O1—C1—C2	29.7 (3)	C15—C10—C11—C12	1.9 (3)
V1—O1—C1—C6	−152.82 (15)	C9—C10—C11—C12	−178.46 (19)
O1—C1—C2—C3	175.72 (18)	O4—C11—C12—C13	178.7 (2)
C6—C1—C2—C3	−1.8 (3)	C10—C11—C12—C13	−2.0 (4)
O1—C1—C2—C8	−3.0 (3)	C11—C12—C13—C14	0.6 (4)
C6—C1—C2—C8	179.54 (17)	C12—C13—C14—C15	0.9 (3)
C1—C2—C3—C4	0.9 (3)	C13—C14—C15—C10	−0.9 (3)
C8—C2—C3—C4	179.6 (2)	C11—C10—C15—C14	−0.5 (3)
C2—C3—C4—C5	0.1 (3)	C9—C10—C15—C14	179.89 (18)
C3—C4—C5—C6	−0.2 (4)	V1—O6—C16—C17	14.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···N2	0.82	1.86	2.581 (2)	147
C8—H8A···O4i	0.93	2.31	3.236 (2)	177

Table 1

Selected bond lengths (Å)

V1—N1	2.1029 (15)
V1—O1	1.8325 (14)
V1—O3	1.9453 (14)
V1—O5	1.5762 (15)
V1—O6	1.7423 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯N2	0.82	1.86	2.581 (2)	147
C8—H8A⋯O4i	0.93	2.31	3.236 (2)	177

Symmetry code: (i) .