Methanol{2-meth­oxy-6-[(2-oxidoprop­yl)imino­meth­yl]phenolato}dioxidomolyb­denum(VI)

Samira Saeednia; Iran Sheikhshoaie; Helen Stoeckli-Evans

doi:10.1107/S1600536809047485

. 2009 Nov 18;65(Pt 12):m1591. doi: 10.1107/S1600536809047485

Methanol{2-methoxy-6-[(2-oxidopropyl)iminomethyl]phenolato}dioxidomolybdenum(VI)

Samira Saeednia ^a, Iran Sheikhshoaie ^a,^*, Helen Stoeckli-Evans ^b

PMCID: PMC2972118 PMID: 21578621

Abstract

In the structure of the title compound, [Mo(C₁₁H₁₃NO₃)O₂(CH₃OH)], the Mo^VI ion is octahedrally coordinated by two oxide O atoms, the N atom and two deprotonated OH groups of the tridentate Schiff base ligand 2-methoxy-6-[(2-oxidopropyl)iminomethyl]phenolate and by a methanol O atom. In the crystal structure, two complexes are linked via O—H⋯O hydrogen bonds, yielding a centrosymmetric arrangement involving the methanol hydroxy group and one of the ligand O atoms coordinated to the Mo^VI ion.

Related literature

For molybdenum (VI) Schiff base complexes in bioinorganic chemistry, see: Holm et al. (1996 ▶) and as oxidation catalysts, see: Arnaiz et al. (2000 ▶); Sheikhshoaie et al. (2009 ▶). For similar structures, see: Abbasi et al. (2008 ▶); Monadi et al. (2009 ▶); Syamal & Maurya (1989 ▶). graphic file with name e-65-m1591-scheme1.jpg

Experimental

Crystal data

[Mo(C₁₁H₁₃NO₃)O₂(CH₄O)]
M _r = 367.21
Monoclinic,
a = 6.7551 (5) Å
b = 15.8357 (14) Å
c = 13.1198 (10) Å
β = 98.287 (9)°
V = 1388.79 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 173 K
0.38 × 0.38 × 0.34 mm

Data collection

Stoe IPDS diffractometer
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T _min = 0.625, T _max = 0.716
10555 measured reflections
2666 independent reflections
2601 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.063
S = 1.16
2666 reflections
187 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047485/fi2093sup1.cif

e-65-m1591-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047485/fi2093Isup2.hkl

e-65-m1591-Isup2.hkl^{(130.9KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6O⋯O1ⁱ	0.83 (3)	1.81 (3)	2.639 (2)	176 (2)

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Various molybdenum(VI) Schiff base complexes have been studied due to their importance in the domains of bioinorganic chemistry (Holm et al., (1996), analytical chemistry, oxidation catalyst (Arnaiz et al., 2000; Sheikhshoaie et al., 2009) and structural chemistry (Abbasi et al., 2008; Monadi et al., 2009; Syamal & Maurya, 1989). In continuation of our interest in this line of research we have prepared the title compound, synthesized by the reaction of MoO₂(acac)₂ and the Schiff base ligand 2-[(2-hydroxy-propylimino)-methyl]-phenol in methanol.

The molecular structure of the title compound is illustrated in Fig. 1 and geometrical parameters are available in the supplementary material as well as in the deposited CIF. The molybdenum atom, Mo1, has a distorted octahedral coordination, being coordinated by the N and two O-atoms of the tridentate Schiff base ligand (N1, O1 and O2), two oxido O-atoms (O4 and O5), and by the O-atom (O6) of the coordinating methanol molecule. The Mo—O and Mo—N bond distances are similar to those reported for the molybdenum (VI) Schiff base complex, {1,1'-[(2,2-Dimethylpropane-1,3-diyl)bis(nitrilomethylidyne)] di-2-naphtholato}dioxidomolybdenum(VI) dichloromethane 1.75-solvate, (Monadi et al., 2009).

In the crystal, complexes are linked via hydrogen bonds, O6—H6O···O1ⁱ [symmetry operation (i) = -x, -y, -z], involving the methanol hydroxy group and a ligand O-atom coordinating to the second Mo atom so forming centrosymmetric dimers (Table 1 and Fig. 2).

Experimental

The title compound was prepared by adding MoO₂(acac)₂ (0.327 g) to a dry methanolic solution (30 ml) of 2-[(2-hydroxy-propylimino)-methyl]-phenol (0.209 g); a 1:1 equimolar ratio. The mixture was then refluxed for 5 h. On cooling a yellow crystalline powder formed, which were filtered off. Crystals of the title complex, suitable for X-ray analysis, were obtained as yellow blocks by slow evaporation at room temperature of a solution in methanol.