Methano­ldioxido{1-[(2RS)-(2-oxidoprop­yl)iminometh­yl]-2-naphtholato}molybdenium(VI)

Monadi Niaz; Sheikhshoaie Iran; Rezaeifard Abdolreza

doi:10.1107/S160053681000262X

. 2010 Jan 27;66(Pt 2):m202. doi: 10.1107/S160053681000262X

Methanoldioxido{1-[(2RS)-(2-oxidopropyl)iminomethyl]-2-naphtholato}molybdenium(VI)

Monadi Niaz ^a, Sheikhshoaie Iran ^b,^*, Rezaeifard Abdolreza ^c

PMCID: PMC2979794 PMID: 21579666

Abstract

Crystals of the title compound, [Mo(C₁₄H₁₃NO₂)O₂(CH₄O)], were obtained by recrystallization from methanol. The Mo^VI atom is coordinated by two oxide O atoms and by two O atoms and one N atom of the tridentate 1-[(2-oxidopropyl)iminomethyl]-2-naphtholate Schiff base ligand. The coordination sphere is completed by the O atom of a methanol molecule, yielding a distorted octahedron. O—H⋯O hydrogen bonding yields centrosymmetric dimers.

Related literature

For related structures with O= Mo^VI=O units and for the synthesis, see: Arnaiz et al. (2000 ▶); Holm et al. (1996 ▶); Syamal & Maurya (1989 ▶). For the prperties of related compounds, see: Arnold et al. (2001 ▶); Bagherzadeh et al. (2009 ▶); Bruno et al. (2006 ▶); Holm (1987 ▶); Maurya et al. (1997 ▶); Schurig & Betschinger (1992 ▶); Sheikhshoaie et al. (2009 ▶).

Experimental

Crystal data

[Mo(C₁₄H₁₃NO₂)O₂(CH₄O)]
M _r = 387.24
Monoclinic,
a = 7.9064 (5) Å
b = 15.078 (1) Å
c = 12.6796 (8) Å
β = 93.959 (1)°
V = 1507.96 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 100 K
0.19 × 0.16 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.849, T _max = 0.870
18948 measured reflections
4393 independent reflections
3951 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.023
wR(F ²) = 0.056
S = 1.01
4393 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000262X/fi2095sup1.cif

e-66-0m202-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000262X/fi2095Isup2.hkl

e-66-0m202-Isup2.hkl^{(215.3KB, 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
O5—H5O⋯O2ⁱ	0.85	1.82	2.6667 (16)	179

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the Shahid Bahonar University of Kerman for financial support of this work.

supplementary crystallographic information

Comment

Transition metal oxo compounds containing Schiff base ligands have been in the focus of scientific interest for many years. These compounds are involved in oxygen transfer chemistry in both biological and industrial processes (Maurya et al., 1997), effective catalysts for epoxidation (Bagherzadeh et al., 2009; Holm, 1987; Schurig & Betschinger, 1992; Arnold et al., 2001). The success of molybdenum(VI) complexes in reactions to produce racemic epoxides led to the belief that some derivatives of these complexes could be applied as chiral catalysts (Bruno et al., 2006), and oxidation catalysis (Sheikhshoaie et al., 2009). Continuing our interest in the structural chemistry of dioxomolybdenum(VI) Schiff base complexes, we have synthesized and structurally characterized the title complex.

The molecular structure of the title complex is illustrated in Figure 1. The Mo^VI ion is in a distored octahedral environment being coordinated by two oxido O atoms (O4 and O3), three atoms (two oxygen and one nitrogen atoms) of the tridentate Schiff base ligand and one oxygen atom from methanol. The oxido-O atoms are in cis position with short Mo=O bonds (1.7001 (12) and 1.7140 (12)Å, respectively). The OH group of the methanol molecule acts as H bond donor, yielding centrosymmetric dimers (Fig. 2).

Experimental

To a solution of 0.229 mg (1 mmol) of tridentate Schiff base ligand 1-((E)-(2-hydroxypropylimino)methyl)naphthalen-2-ol) in 15 ml dry methanol was added a solution of 0.327 mg (1 mmol) of MoO2(acac)2 in 10 ml dry methanol, and refluxed for an additional 2 h. {[(1-amino-2-hydroxypropane)nitilomethylidyne-(2-naphthalato)]-dioxidomolybdenum(VI)(Methanol)} was obtained as a yellow microcrystalline precipitate. The precipitate was filtered off, washed with 5 ml absolute ethanol. Small yellow crystals formed upon recrystallisation from methanol.