[N'-(3-Eth-oxy-2-oxidobenzyl-idene)-4-hy-droxy-3-meth-oxy-benzohydrazidato](methanol)dioxidomolybdenum(VI).

In the title dioxidomolybdenum(VI) complex, [Mo(C(17)H(16)N(2)O(5))O(2)(CH(3)OH)], the Mo(VI) atom is coordinated by the phenolate O, imine N and enolic O atoms of the tridentate hydrazone ligand, one methanol O atom, and two oxide O atoms, forming a distorted octa-hedral coordination geometry. The oxide O atoms adopt a cis conformation: one is trans to the methanol O atom and the other is trans to the ligand N atom. The dihedral angle between the two benzene rings in the hydrazone ligand is 4.0 (3)°. In the crystal, mol-ecules are linked by O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For background to molybdenum complexes with hydrazone ligands, see: Dinda et al. (2003 ▶); Vrdoljak et al. (2005 ▶); Debel et al. (2008 ▶). For similar complexes, see: Sheikhshoaie et al. (2011 ▶); Gao et al. (2004 ▶); Saeednia et al. (2009 ▶).

Experimental

Crystal data

[Mo(C17H16N2O5)O2(CH4O)]

M = 488.30

Monoclinic,

a = 10.054 (2) Å

b = 16.401 (3) Å

c = 12.233 (3) Å

β = 101.946 (2)°

V = 1973.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.71 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.853, T max = 0.871

11140 measured reflections

4300 independent reflections

3162 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.093

S = 1.03

4300 reflections

269 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.69 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/S1600536812008549/hb6656sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008549/hb6656Isup2.hkl

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

[Mo(C17H16N2O5)O2(CH4O)]	F(000) = 992
Mr = 488.30	Dx = 1.643 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.054 (2) Å	Cell parameters from 2809 reflections
b = 16.401 (3) Å	θ = 2.7–25.1°
c = 12.233 (3) Å	µ = 0.71 mm−1
β = 101.946 (2)°	T = 298 K
V = 1973.5 (7) Å3	Block, yellow
Z = 4	0.23 × 0.21 × 0.20 mm

Bruker SMART CCD diffractometer	4300 independent reflections
Radiation source: fine-focus sealed tube	3162 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scan	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→10
Tmin = 0.853, Tmax = 0.871	k = −13→20
11140 measured reflections	l = −15→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0346P)2 + 1.5131P] where P = (Fo2 + 2Fc2)/3
4300 reflections	(Δ/σ)max < 0.001
269 parameters	Δρmax = 0.62 e Å−3
1 restraint	Δρmin = −0.69 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
Mo1	0.20815 (3)	0.10239 (2)	0.35081 (2)	0.02894 (11)
N1	0.4173 (3)	0.05321 (18)	0.3574 (2)	0.0250 (7)
N2	0.5200 (3)	0.08381 (18)	0.4423 (2)	0.0260 (7)
O1	0.1607 (2)	0.00584 (16)	0.2626 (2)	0.0354 (6)
O2	−0.0005 (3)	−0.07464 (17)	0.1042 (2)	0.0449 (7)
O3	0.3379 (2)	0.15737 (15)	0.4761 (2)	0.0332 (6)
O4	0.9131 (2)	0.23736 (17)	0.7064 (2)	0.0410 (7)
O5	0.7908 (3)	0.3165 (2)	0.8463 (2)	0.0507 (8)
H5	0.8685	0.3204	0.8357	0.076*
O6	0.2310 (3)	0.00410 (17)	0.4948 (2)	0.0357 (6)
O7	0.0629 (2)	0.12772 (16)	0.3944 (2)	0.0381 (7)
O8	0.2216 (3)	0.16890 (18)	0.2489 (2)	0.0459 (7)
C1	0.3597 (4)	−0.0307 (2)	0.1922 (3)	0.0337 (9)
C2	0.2189 (4)	−0.0313 (2)	0.1862 (3)	0.0307 (9)
C3	0.1332 (4)	−0.0746 (2)	0.0993 (3)	0.0355 (9)
C4	0.1891 (4)	−0.1132 (3)	0.0195 (3)	0.0460 (11)
H4	0.1330	−0.1412	−0.0384	0.055*
C5	0.3281 (5)	−0.1108 (3)	0.0245 (3)	0.0519 (12)
H5A	0.3638	−0.1364	−0.0309	0.062*
C6	0.4132 (4)	−0.0715 (3)	0.1099 (3)	0.0440 (11)
H6A	0.5065	−0.0717	0.1134	0.053*
C7	−0.0893 (4)	−0.1285 (3)	0.0308 (4)	0.0546 (13)
H7A	−0.0566	−0.1842	0.0420	0.065*
H7B	−0.0922	−0.1136	−0.0464	0.065*
C8	0.4533 (4)	0.0069 (2)	0.2837 (3)	0.0318 (9)
H8	0.5456	−0.0029	0.2898	0.038*
C9	0.4682 (3)	0.1391 (2)	0.4979 (3)	0.0261 (8)
C10	0.5546 (3)	0.1847 (2)	0.5889 (3)	0.0251 (8)
C11	0.6961 (3)	0.1855 (2)	0.6019 (3)	0.0276 (8)
H11	0.7371	0.1563	0.5527	0.033*
C12	0.7752 (3)	0.2295 (2)	0.6876 (3)	0.0288 (8)
C13	0.7136 (4)	0.2728 (2)	0.7621 (3)	0.0347 (9)
C14	0.5754 (4)	0.2711 (3)	0.7500 (3)	0.0431 (11)
H14	0.5351	0.2992	0.8007	0.052*
C15	0.4948 (4)	0.2285 (2)	0.6640 (3)	0.0357 (9)
H15	0.4008	0.2289	0.6560	0.043*
C16	0.9849 (4)	0.1843 (3)	0.6466 (4)	0.0459 (11)
H16A	0.9636	0.1287	0.6605	0.069*
H16B	1.0809	0.1931	0.6708	0.069*
H16C	0.9585	0.1955	0.5680	0.069*
C17	0.1822 (5)	0.0181 (3)	0.5950 (4)	0.0558 (12)
H17A	0.2257	0.0655	0.6322	0.084*
H17B	0.2025	−0.0284	0.6433	0.084*
H17C	0.0857	0.0265	0.5767	0.084*
C18	−0.2272 (5)	−0.1219 (3)	0.0562 (4)	0.0709 (16)
H18A	−0.2235	−0.1373	0.1325	0.106*
H18B	−0.2886	−0.1574	0.0076	0.106*
H18C	−0.2586	−0.0666	0.0450	0.106*
H6	0.303 (3)	−0.024 (3)	0.511 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Mo1	0.02297 (16)	0.0324 (2)	0.02923 (16)	0.00327 (15)	0.00036 (11)	−0.00289 (16)
N1	0.0226 (14)	0.0258 (18)	0.0255 (14)	0.0006 (13)	0.0022 (11)	−0.0011 (13)
N2	0.0231 (14)	0.0284 (19)	0.0250 (14)	−0.0023 (13)	0.0014 (12)	−0.0044 (13)
O1	0.0278 (13)	0.0443 (17)	0.0327 (13)	−0.0031 (12)	0.0028 (11)	−0.0133 (12)
O2	0.0377 (16)	0.0480 (19)	0.0451 (16)	−0.0068 (13)	0.0001 (13)	−0.0127 (14)
O3	0.0254 (13)	0.0348 (16)	0.0366 (14)	0.0043 (11)	0.0001 (11)	−0.0101 (12)
O4	0.0257 (13)	0.0491 (19)	0.0464 (16)	−0.0047 (13)	0.0033 (12)	−0.0179 (14)
O5	0.0381 (16)	0.067 (2)	0.0477 (17)	−0.0168 (16)	0.0106 (13)	−0.0329 (16)
O6	0.0380 (15)	0.0371 (17)	0.0331 (14)	0.0124 (12)	0.0094 (12)	0.0000 (12)
O7	0.0253 (13)	0.0424 (17)	0.0457 (15)	0.0103 (12)	0.0055 (11)	−0.0024 (13)
O8	0.0429 (16)	0.0486 (19)	0.0431 (16)	0.0050 (14)	0.0017 (13)	0.0102 (14)
C1	0.035 (2)	0.033 (2)	0.0323 (19)	0.0005 (18)	0.0052 (16)	−0.0063 (17)
C2	0.036 (2)	0.030 (2)	0.0248 (18)	0.0018 (17)	0.0026 (15)	−0.0005 (16)
C3	0.039 (2)	0.031 (2)	0.034 (2)	−0.0017 (18)	0.0019 (17)	−0.0013 (17)
C4	0.051 (3)	0.047 (3)	0.038 (2)	−0.003 (2)	0.0029 (19)	−0.017 (2)
C5	0.055 (3)	0.060 (3)	0.042 (2)	0.004 (2)	0.014 (2)	−0.024 (2)
C6	0.036 (2)	0.053 (3)	0.044 (2)	0.004 (2)	0.0085 (18)	−0.015 (2)
C7	0.050 (3)	0.050 (3)	0.055 (3)	−0.007 (2)	−0.011 (2)	−0.014 (2)
C8	0.0244 (18)	0.038 (2)	0.0326 (19)	0.0040 (17)	0.0042 (15)	−0.0066 (18)
C9	0.0266 (18)	0.027 (2)	0.0237 (17)	−0.0015 (16)	0.0028 (14)	0.0021 (16)
C10	0.0284 (18)	0.021 (2)	0.0251 (16)	0.0006 (15)	0.0035 (14)	0.0007 (15)
C11	0.0303 (18)	0.027 (2)	0.0261 (17)	0.0027 (16)	0.0081 (14)	−0.0029 (16)
C12	0.0262 (18)	0.029 (2)	0.0297 (18)	−0.0013 (16)	0.0019 (15)	0.0006 (16)
C13	0.035 (2)	0.039 (3)	0.0302 (19)	−0.0065 (18)	0.0065 (16)	−0.0095 (18)
C14	0.040 (2)	0.050 (3)	0.042 (2)	0.001 (2)	0.0143 (18)	−0.018 (2)
C15	0.0254 (19)	0.040 (3)	0.042 (2)	−0.0021 (17)	0.0084 (16)	−0.0104 (19)
C16	0.031 (2)	0.051 (3)	0.058 (3)	0.001 (2)	0.0139 (19)	−0.009 (2)
C17	0.050 (3)	0.062 (3)	0.059 (3)	0.009 (2)	0.021 (2)	0.007 (3)
C18	0.046 (3)	0.082 (4)	0.078 (4)	−0.014 (3)	−0.001 (3)	−0.011 (3)

Mo1—O8	1.683 (3)	C5—C6	1.367 (5)
Mo1—O7	1.707 (2)	C5—H5A	0.9300
Mo1—O1	1.920 (2)	C6—H6A	0.9300
Mo1—O3	2.009 (2)	C7—C18	1.487 (6)
Mo1—N1	2.238 (3)	C7—H7A	0.9700
Mo1—O6	2.364 (3)	C7—H7B	0.9700
N1—C8	1.286 (4)	C8—H8	0.9300
N1—N2	1.398 (4)	C9—C10	1.467 (4)
N2—C9	1.305 (4)	C10—C15	1.397 (5)
O1—C2	1.347 (4)	C10—C11	1.399 (5)
O2—C3	1.358 (4)	C11—C12	1.380 (5)
O2—C7	1.432 (4)	C11—H11	0.9300
O3—C9	1.316 (4)	C12—C13	1.398 (5)
O4—C12	1.364 (4)	C13—C14	1.366 (5)
O4—C16	1.425 (4)	C14—C15	1.378 (5)
O5—C13	1.360 (4)	C14—H14	0.9300
O5—H5	0.8200	C15—H15	0.9300
O6—C17	1.430 (5)	C16—H16A	0.9600
O6—H6	0.847 (10)	C16—H16B	0.9600
C1—C2	1.402 (5)	C16—H16C	0.9600
C1—C6	1.405 (5)	C17—H17A	0.9600
C1—C8	1.444 (5)	C17—H17B	0.9600
C2—C3	1.413 (5)	C17—H17C	0.9600
C3—C4	1.377 (5)	C18—H18A	0.9600
C4—C5	1.386 (6)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
O8—Mo1—O7	106.19 (13)	C18—C7—H7A	110.1
O8—Mo1—O1	99.61 (12)	O2—C7—H7B	110.1
O7—Mo1—O1	104.31 (12)	C18—C7—H7B	110.1
O8—Mo1—O3	97.79 (12)	H7A—C7—H7B	108.4
O7—Mo1—O3	96.60 (11)	N1—C8—C1	124.3 (3)
O1—Mo1—O3	147.72 (10)	N1—C8—H8	117.9
O8—Mo1—N1	92.37 (12)	C1—C8—H8	117.9
O7—Mo1—N1	159.23 (11)	N2—C9—O3	122.7 (3)
O1—Mo1—N1	81.09 (10)	N2—C9—C10	120.8 (3)
O3—Mo1—N1	71.19 (10)	O3—C9—C10	116.5 (3)
O8—Mo1—O6	169.67 (11)	C15—C10—C11	119.1 (3)
O7—Mo1—O6	83.73 (11)	C15—C10—C9	119.6 (3)
O1—Mo1—O6	80.25 (10)	C11—C10—C9	121.3 (3)
O3—Mo1—O6	77.86 (10)	C12—C11—C10	120.3 (3)
N1—Mo1—O6	77.38 (9)	C12—C11—H11	119.9
C8—N1—N2	117.5 (3)	C10—C11—H11	119.9
C8—N1—Mo1	125.9 (2)	O4—C12—C11	125.7 (3)
N2—N1—Mo1	116.2 (2)	O4—C12—C13	114.5 (3)
C9—N2—N1	108.9 (3)	C11—C12—C13	119.8 (3)
C2—O1—Mo1	132.1 (2)	O5—C13—C14	120.1 (3)
C3—O2—C7	117.9 (3)	O5—C13—C12	120.1 (3)
C9—O3—Mo1	121.0 (2)	C14—C13—C12	119.8 (3)
C12—O4—C16	117.4 (3)	C13—C14—C15	121.1 (4)
C13—O5—H5	109.5	C13—C14—H14	119.4
C17—O6—Mo1	122.1 (2)	C15—C14—H14	119.4
C17—O6—H6	108 (3)	C14—C15—C10	119.9 (3)
Mo1—O6—H6	120 (3)	C14—C15—H15	120.1
C2—C1—C6	119.4 (3)	C10—C15—H15	120.1
C2—C1—C8	122.2 (3)	O4—C16—H16A	109.5
C6—C1—C8	118.3 (3)	O4—C16—H16B	109.5
O1—C2—C1	122.6 (3)	H16A—C16—H16B	109.5
O1—C2—C3	117.7 (3)	O4—C16—H16C	109.5
C1—C2—C3	119.7 (3)	H16A—C16—H16C	109.5
O2—C3—C4	125.7 (3)	H16B—C16—H16C	109.5
O2—C3—C2	115.0 (3)	O6—C17—H17A	109.5
C4—C3—C2	119.3 (4)	O6—C17—H17B	109.5
C3—C4—C5	120.7 (4)	H17A—C17—H17B	109.5
C3—C4—H4	119.6	O6—C17—H17C	109.5
C5—C4—H4	119.6	H17A—C17—H17C	109.5
C6—C5—C4	120.9 (4)	H17B—C17—H17C	109.5
C6—C5—H5A	119.6	C7—C18—H18A	109.5
C4—C5—H5A	119.6	C7—C18—H18B	109.5
C5—C6—C1	120.0 (4)	H18A—C18—H18B	109.5
C5—C6—H6A	120.0	C7—C18—H18C	109.5
C1—C6—H6A	120.0	H18A—C18—H18C	109.5
O2—C7—C18	108.1 (4)	H18B—C18—H18C	109.5
O2—C7—H7A	110.1

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···N2i	0.85 (1)	2.01 (1)	2.853 (4)	175 (5)
O5—H5···O4	0.82	2.20	2.646 (4)	114
O5—H5···O7ii	0.82	2.12	2.828 (3)	145

Table 1

Selected bond lengths (Å)

Mo1—O8	1.683 (3)
Mo1—O7	1.707 (2)
Mo1—O1	1.920 (2)
Mo1—O3	2.009 (2)
Mo1—N1	2.238 (3)
Mo1—O6	2.364 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯N2i	0.85 (1)	2.01 (1)	2.853 (4)	175 (5)
O5—H5⋯O4	0.82	2.20	2.646 (4)	114
O5—H5⋯O7ii	0.82	2.12	2.828 (3)	145

Symmetry codes: (i) ; (ii) .