[N'-(3,5-Diiodo-2-oxidobenzyl-idene-κO)-4-methyl-benzohydrazidato-κN',O](methanol-κO)(methano-lato-κO)oxidovanadium(V).

In the title mol-ecule, [V(C(15)H(10)I(2)N(2)O(2))(CH(3)O)O(CH(3)OH)], the V(V) atom is coordinated by one N and two O atoms from an N'-(3,5-diiodo-2-oxidobenzyl-idene-κO)-4-methyl-benzo-hydra-zidate (L) ligand, one oxide O atom, one methano-late [V-O = 1.761 (3) Å] and one methanol [V-O = 2.383 (4) Å] O atom in a distorted octa-hedral geometry. In the L ligand, the two benzene rings are nearly parallel, forming a dihedral angle of 2.0 (1)°. In the crystal, inter-molecular O-H⋯N hydrogen bonds link pairs of mol-ecules into centrosymmetric dimers which exhibit π-π inter-actions between the aromatic rings [centroid-centroid distance = 3.677 (5) Å].

Related literature

For background to oxidovanadium complexes, see: Chohan et al. (2010 ▶); Chohan & Sumrra (2010 ▶); Sharma et al. (2010 ▶); Tian et al. (2010 ▶). For similar oxidovanadium(V) complexes, see: Wang (2011 ▶); Rajak et al. (2000 ▶); Mondal et al. (2009 ▶).

Experimental

Crystal data

[V(C15H10I2N2O2)(CH3O)O(CH4O)]

M = 634.07

Triclinic,

a = 7.890 (5) Å

b = 10.030 (6) Å

c = 13.628 (8) Å

α = 81.857 (5)°

β = 84.777 (6)°

γ = 85.286 (5)°

V = 1060.5 (11) Å3

Z = 2

Mo Kα radiation

μ = 3.41 mm−1

T = 298 K

0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.595, T max = 0.685

7706 measured reflections

4283 independent reflections

3146 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.090

S = 1.02

4283 reflections

250 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.00 e Å−3

Δρmin = −1.01 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 datablocks global, I. DOI: 10.1107/S1600536811010385/cv5063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010385/cv5063Isup2.hkl

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

[V(C15H10I2N2O2)(CH3O)O(CH4O)]	Z = 2
Mr = 634.07	F(000) = 604
Triclinic, P1	Dx = 1.986 Mg m−3
a = 7.890 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.030 (6) Å	Cell parameters from 2583 reflections
c = 13.628 (8) Å	θ = 2.7–25.0°
α = 81.857 (5)°	µ = 3.41 mm−1
β = 84.777 (6)°	T = 298 K
γ = 85.286 (5)°	Block, red
V = 1060.5 (11) Å3	0.17 × 0.13 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	4283 independent reflections
Radiation source: fine-focus sealed tube	3146 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.595, Tmax = 0.685	k = −12→12
7706 measured reflections	l = −17→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.03P)2 + 1.6979P] where P = (Fo2 + 2Fc2)/3
4283 reflections	(Δ/σ)max < 0.001
250 parameters	Δρmax = 1.00 e Å−3
1 restraint	Δρmin = −1.01 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	0.23465 (11)	0.25458 (7)	0.54517 (6)	0.0344 (2)
I1	0.54984 (5)	−0.39607 (4)	0.86399 (3)	0.06551 (15)
I2	0.39530 (6)	0.20017 (4)	0.87434 (3)	0.06716 (16)
N1	0.2307 (5)	0.0559 (4)	0.5077 (3)	0.0311 (9)
N2	0.1714 (5)	0.0473 (4)	0.4152 (3)	0.0346 (9)
O1	0.1488 (5)	0.2762 (3)	0.4147 (2)	0.0423 (8)
O2	0.2580 (5)	0.1637 (3)	0.6730 (2)	0.0428 (8)
O3	0.4296 (4)	0.2723 (3)	0.5122 (3)	0.0497 (9)
O4	−0.0568 (5)	0.2139 (3)	0.5921 (3)	0.0439 (8)
O5	0.1603 (4)	0.4154 (3)	0.5753 (3)	0.0417 (8)
C1	0.3464 (6)	−0.0661 (4)	0.6552 (3)	0.0348 (11)
C2	0.4118 (6)	−0.1917 (5)	0.7000 (4)	0.0379 (11)
H2	0.4156	−0.2667	0.6666	0.046*
C3	0.4699 (6)	−0.2047 (5)	0.7927 (4)	0.0410 (12)
C4	0.4695 (7)	−0.0928 (5)	0.8431 (4)	0.0459 (13)
H4A	0.5129	−0.1016	0.9051	0.055*
C5	0.4040 (6)	0.0303 (5)	0.7998 (4)	0.0394 (12)
C6	0.3362 (6)	0.0472 (5)	0.7069 (3)	0.0344 (11)
C7	0.2817 (6)	−0.0561 (4)	0.5582 (4)	0.0337 (11)
H7	0.2768	−0.1353	0.5307	0.040*
C8	0.1344 (6)	0.1705 (5)	0.3713 (4)	0.0353 (11)
C9	0.0718 (6)	0.1932 (5)	0.2712 (4)	0.0378 (11)
C10	0.0142 (7)	0.3222 (5)	0.2310 (4)	0.0489 (14)
H10	0.0172	0.3939	0.2671	0.059*
C11	−0.0475 (7)	0.3452 (6)	0.1377 (4)	0.0585 (16)
H11	−0.0874	0.4321	0.1128	0.070*
C12	−0.0512 (7)	0.2434 (7)	0.0813 (4)	0.0559 (15)
C13	0.0081 (8)	0.1157 (6)	0.1213 (4)	0.0622 (17)
H13	0.0079	0.0447	0.0842	0.075*
C14	0.0677 (8)	0.0905 (6)	0.2149 (4)	0.0521 (14)
H14	0.1054	0.0031	0.2400	0.062*
C15	−0.1196 (9)	0.2677 (8)	−0.0205 (5)	0.083 (2)
H15A	−0.0267	0.2622	−0.0707	0.125*
H15B	−0.1781	0.3558	−0.0301	0.125*
H15C	−0.1975	0.2006	−0.0252	0.125*
C16	0.2549 (9)	0.5282 (6)	0.5792 (6)	0.076 (2)
H16A	0.3014	0.5199	0.6427	0.114*
H16B	0.1815	0.6094	0.5702	0.114*
H16C	0.3462	0.5318	0.5275	0.114*
C17	−0.1589 (9)	0.2807 (7)	0.6648 (5)	0.075 (2)
H17A	−0.1085	0.2616	0.7273	0.112*
H17B	−0.2716	0.2491	0.6724	0.112*
H17C	−0.1654	0.3763	0.6437	0.112*
H4	−0.087 (10)	0.134 (3)	0.599 (6)	0.088*

	U11	U22	U33	U12	U13	U23
V1	0.0406 (5)	0.0279 (4)	0.0370 (5)	−0.0040 (3)	−0.0089 (4)	−0.0077 (3)
I1	0.0621 (3)	0.0531 (2)	0.0724 (3)	0.00130 (19)	−0.0126 (2)	0.0238 (2)
I2	0.0971 (4)	0.0637 (3)	0.0486 (3)	−0.0046 (2)	−0.0270 (2)	−0.02184 (19)
N1	0.035 (2)	0.032 (2)	0.028 (2)	−0.0051 (16)	−0.0065 (17)	−0.0065 (16)
N2	0.040 (2)	0.036 (2)	0.030 (2)	−0.0071 (17)	−0.0084 (18)	−0.0070 (17)
O1	0.058 (2)	0.0309 (17)	0.040 (2)	−0.0039 (15)	−0.0132 (17)	−0.0030 (14)
O2	0.061 (2)	0.0335 (18)	0.036 (2)	0.0048 (16)	−0.0160 (17)	−0.0096 (14)
O3	0.044 (2)	0.049 (2)	0.060 (2)	−0.0112 (17)	0.0022 (18)	−0.0205 (18)
O4	0.042 (2)	0.044 (2)	0.049 (2)	−0.0068 (17)	−0.0020 (17)	−0.0133 (17)
O5	0.046 (2)	0.0276 (16)	0.054 (2)	−0.0019 (14)	−0.0085 (17)	−0.0089 (15)
C1	0.036 (3)	0.034 (2)	0.034 (3)	−0.008 (2)	−0.007 (2)	0.002 (2)
C2	0.038 (3)	0.036 (3)	0.040 (3)	−0.008 (2)	−0.004 (2)	−0.003 (2)
C3	0.036 (3)	0.041 (3)	0.043 (3)	−0.007 (2)	−0.005 (2)	0.009 (2)
C4	0.046 (3)	0.058 (3)	0.034 (3)	−0.010 (3)	−0.012 (3)	0.003 (2)
C5	0.045 (3)	0.042 (3)	0.034 (3)	−0.008 (2)	−0.010 (2)	−0.006 (2)
C6	0.033 (3)	0.039 (3)	0.032 (3)	−0.009 (2)	−0.002 (2)	−0.006 (2)
C7	0.036 (3)	0.029 (2)	0.038 (3)	−0.005 (2)	−0.005 (2)	−0.006 (2)
C8	0.033 (3)	0.038 (3)	0.035 (3)	−0.008 (2)	−0.003 (2)	0.000 (2)
C9	0.033 (3)	0.048 (3)	0.032 (3)	−0.010 (2)	−0.003 (2)	0.000 (2)
C10	0.050 (3)	0.052 (3)	0.045 (3)	−0.010 (3)	−0.010 (3)	0.000 (3)
C11	0.054 (4)	0.069 (4)	0.050 (4)	−0.011 (3)	−0.016 (3)	0.016 (3)
C12	0.041 (3)	0.089 (5)	0.036 (3)	−0.009 (3)	−0.009 (3)	0.003 (3)
C13	0.076 (5)	0.077 (4)	0.037 (3)	−0.009 (4)	−0.016 (3)	−0.010 (3)
C14	0.065 (4)	0.056 (3)	0.036 (3)	−0.003 (3)	−0.013 (3)	−0.002 (2)
C15	0.075 (5)	0.127 (6)	0.046 (4)	−0.008 (4)	−0.023 (4)	0.008 (4)
C16	0.073 (5)	0.037 (3)	0.122 (6)	−0.015 (3)	−0.007 (4)	−0.021 (3)
C17	0.069 (5)	0.069 (4)	0.087 (5)	−0.008 (3)	0.013 (4)	−0.026 (4)

V1—O3	1.580 (4)	C5—C6	1.402 (6)
V1—O5	1.761 (3)	C7—H7	0.9300
V1—O2	1.865 (3)	C8—C9	1.475 (6)
V1—O1	1.938 (3)	C9—C14	1.372 (7)
V1—N1	2.130 (4)	C9—C10	1.389 (7)
V1—O4	2.383 (4)	C10—C11	1.385 (7)
I1—C3	2.100 (5)	C10—H10	0.9300
I2—C5	2.097 (5)	C11—C12	1.366 (8)
N1—C7	1.286 (6)	C11—H11	0.9300
N1—N2	1.400 (5)	C12—C13	1.381 (8)
N2—C8	1.317 (6)	C12—C15	1.514 (8)
O1—C8	1.302 (5)	C13—C14	1.383 (7)
O2—C6	1.319 (5)	C13—H13	0.9300
O4—C17	1.426 (7)	C14—H14	0.9300
O4—H4	0.85 (4)	C15—H15A	0.9600
O5—C16	1.416 (6)	C15—H15B	0.9600
C1—C2	1.400 (6)	C15—H15C	0.9600
C1—C6	1.413 (6)	C16—H16A	0.9600
C1—C7	1.447 (6)	C16—H16B	0.9600
C2—C3	1.368 (7)	C16—H16C	0.9600
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.396 (7)	C17—H17B	0.9600
C4—C5	1.373 (7)	C17—H17C	0.9600
C4—H4A	0.9300
O3—V1—O5	102.77 (17)	N1—C7—C1	123.9 (4)
O3—V1—O2	98.49 (18)	N1—C7—H7	118.1
O5—V1—O2	99.38 (15)	C1—C7—H7	118.1
O3—V1—O1	98.80 (18)	O1—C8—N2	121.8 (4)
O5—V1—O1	96.85 (15)	O1—C8—C9	117.6 (4)
O2—V1—O1	152.99 (14)	N2—C8—C9	120.7 (4)
O3—V1—N1	96.54 (16)	C14—C9—C10	117.8 (5)
O5—V1—N1	159.79 (16)	C14—C9—C8	122.4 (5)
O2—V1—N1	83.42 (14)	C10—C9—C8	119.8 (5)
O1—V1—N1	74.12 (14)	C11—C10—C9	120.7 (5)
O3—V1—O4	176.43 (15)	C11—C10—H10	119.7
O5—V1—O4	80.79 (14)	C9—C10—H10	119.7
O2—V1—O4	81.04 (15)	C12—C11—C10	121.7 (6)
O1—V1—O4	80.42 (14)	C12—C11—H11	119.2
N1—V1—O4	79.89 (13)	C10—C11—H11	119.2
C7—N1—N2	116.4 (4)	C11—C12—C13	117.3 (5)
C7—N1—V1	127.8 (3)	C11—C12—C15	121.9 (6)
N2—N1—V1	115.7 (3)	C13—C12—C15	120.8 (6)
C8—N2—N1	108.5 (4)	C12—C13—C14	121.8 (6)
C8—O1—V1	119.9 (3)	C12—C13—H13	119.1
C6—O2—V1	133.0 (3)	C14—C13—H13	119.1
C17—O4—V1	123.2 (3)	C9—C14—C13	120.7 (5)
C17—O4—H4	107 (5)	C9—C14—H14	119.7
V1—O4—H4	119 (6)	C13—C14—H14	119.7
C16—O5—V1	128.6 (4)	C12—C15—H15A	109.5
C2—C1—C6	119.8 (4)	C12—C15—H15B	109.5
C2—C1—C7	119.1 (4)	H15A—C15—H15B	109.5
C6—C1—C7	120.9 (4)	C12—C15—H15C	109.5
C3—C2—C1	120.4 (4)	H15A—C15—H15C	109.5
C3—C2—H2	119.8	H15B—C15—H15C	109.5
C1—C2—H2	119.8	O5—C16—H16A	109.5
C2—C3—C4	120.8 (5)	O5—C16—H16B	109.5
C2—C3—I1	120.1 (4)	H16A—C16—H16B	109.5
C4—C3—I1	119.0 (4)	O5—C16—H16C	109.5
C5—C4—C3	119.0 (5)	H16A—C16—H16C	109.5
C5—C4—H4A	120.5	H16B—C16—H16C	109.5
C3—C4—H4A	120.5	O4—C17—H17A	109.5
C4—C5—C6	122.2 (4)	O4—C17—H17B	109.5
C4—C5—I2	120.3 (4)	H17A—C17—H17B	109.5
C6—C5—I2	117.5 (3)	O4—C17—H17C	109.5
O2—C6—C5	120.1 (4)	H17A—C17—H17C	109.5
O2—C6—C1	122.1 (4)	H17B—C17—H17C	109.5
C5—C6—C1	117.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N2i	0.85 (4)	2.03 (5)	2.858 (5)	168 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N2i	0.85 (4)	2.03 (5)	2.858 (5)	168 (8)

Symmetry code: (i) .