Aqua­[N′-(3-eth­oxy-2-oxidobenzyl-κO)furan-1-carbohydrazidato-κ2 N′,O]dioxido­molybdenum(VI)–4,4′-bipyridine (2/1)

Ngui Khiong Ngan; Richard Chee Seng Wong; Kong Mun Lo; Seik Weng Ng

doi:10.1107/S1600536811017260

. 2011 May 14;67(Pt 6):m748. doi: 10.1107/S1600536811017260

Aqua[N′-(3-ethoxy-2-oxidobenzyl-κO)furan-1-carbohydrazidato-κ² N′,O]dioxidomolybdenum(VI)–4,4′-bipyridine (2/1)

Ngui Khiong Ngan ^a, Richard Chee Seng Wong ^a, Kong Mun Lo ^a, Seik Weng Ng ^a,^*

PMCID: PMC3120460 PMID: 21754639

Abstract

The Mo^VI atom in the title co-crystal, [Mo(C₁₄H₁₂N₂O₄)O₂(H₂O)]·0.5C₁₀H₈N₂, is O,N,O′-chelated by the deprotonated Schiff base and coordinated by the oxide and water O atoms in an octahedral geometry. The five-membered chelate ring is planar (r.m.s. deviation = 0.019 Å), but the six-membered chelate ring is puckered (r.m.s. deviation = 0.108 Å). Two mononuclear molecules are linked across a center of inversion by an O—H_water⋯O hydrogen bond; adjacent dinuclear units are linked by an water–4,4′-bipyridine O—H⋯N hydrogen bond, generating a linear chain structure. The 4,4′-bipyridine molecule is disordered over two positions in a 1:1 ratio.

Related literature

For a related Mo^VIO₂–4′,4-bipyridine adduct, see: Dinda et al. (2006 ▶).

Experimental

Crystal data

[Mo(C₁₄H₁₂N₂O₄)O₂(H₂O)]·0.5C₁₀H₈N₂
M _r = 496.30
Triclinic,
a = 7.9237 (1) Å
b = 10.1869 (1) Å
c = 13.3215 (2) Å
α = 78.7841 (5)°
β = 78.4605 (5)°
γ = 69.5728 (5)°
V = 978.15 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 100 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.649, T _max = 0.746
9175 measured reflections
4445 independent reflections
4266 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.076
S = 0.98
4445 reflections
275 parameters
24 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017260/jh2290sup1.cif

e-67-0m748-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017260/jh2290Isup2.hkl

e-67-0m748-Isup2.hkl^{(217.7KB, 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
O1w—H11⋯N3	0.83 (1)	1.86 (1)	2.689 (3)	174 (3)
O1w—H12⋯N1ⁱ	0.84 (1)	1.97 (1)	2.794 (2)	167 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

supplementary crystallographic information

Comment

The Schiff bases that are synthesized by condensing salicylaldehyde (and its substituted analogs) with aroylhydrazides (and their substituted analogs) function as terdentate O,N,O'-chelates to a wide range of metal ions. A large number of metal derivatives have been reported; in octahedral systems, the ligand generally exists as a doubly-deprotonated species that chelates in a fac manner. A dioxomolybdenum(VI) derivative is known in which 4,4'-bipyridine binds to two metal atoms (Dinda et al., 2006). In the present study, a furan-type of Schiff base leads to a water-coordinated derivative in which 4,4'-bipyridine interacts indirectly, through the water molecule, in an outer-sphere coordination mode. The Mo^VI atom in the co-crystal, MoO₂(H₂O)(C₁₄H₁₂N₂O₄)^.0.5C₁₀H₁₀N₂, is O,N,O'-chelated by the deprotonated Schiff base and coordinated by the oxo and water O atoms in an octahedral geometry (Scheme I, Fig. 1). The five-membed chelate ring is planar [r.m.s. deviation 0.019 Å] but the six-membered chelate ring is puckered [r.m.s. deviation 0.108 Å]. Two mononuclear molecules are linked across a center-of-inversion by an O–H_water···O hydrogen bond; adjacent dinuclear units are linked by an O–H_water···N_{4,4'-bipyridine} hydrogen bond to generate a linear chain structure (Table 1). The 4,4'-bipyridine molecule is disordered over two positions in a 1:1 ratio.

Experimental

3-Ethoxysalicylaldehyde (0.166 g, 1 mmol) and 2-furoylhydrazide (0.120 g, 1 mmol) were condensed in methanol (100 ml). The solution was heated to give a yellow coloration. The cool solution yielded the desired Schiff base as a yellow compound. The ligand (0.270 g, 1 mmol) and di(acetylacetonato)dioxomolybdenum(VI) (0.328 g, 1 mmol) were dissolved in heated in methanol for an hour. To the orange solution was added 4,4'-bipyridine (0.08 g, 0.5 mmol); heating was continued for another hour. The solution was filtered and set aside for the growth of crystals, m.p. 495–497 K.