Aqua­{6,6′-dieth­oxy-2,2′-[ethane-1,2-diyl­bis(nitrilo­methanylyl­idene)]diphen­olato}zinc

Chen-Yi Wang; Xiang Wu; Juan-Juan Hu; Zhi-Ping Han

doi:10.1107/S1600536811031497

. 2011 Aug 11;67(Pt 9):m1220. doi: 10.1107/S1600536811031497

Aqua{6,6′-diethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato}zinc

Chen-Yi Wang ^a,^*, Xiang Wu ^a, Juan-Juan Hu ^b, Zhi-Ping Han ^a

PMCID: PMC3200652 PMID: 22065396

Abstract

The mononuclear zinc title complex, [Zn(C₂₀H₂₂N₂O₄)(H₂O)], was obtained by the reaction of 3-ethoxysalicylaldehyde, ethane-1,2-diamine, and zinc acetate in methanol. The Zn atom is five-coordinated by two phenolate O and two imine N atoms of the tetradentate Schiff base ligand and by one water O atom, forming a square-pyramidal geometry. In the crystal, pairs of molecules are linked via intermolecular O—H⋯O hydrogen bonds, forming dimers.

Related literature

For Schiff base complexes reported by our group, see: Wang (2009 ▶); Wang & Ye (2011 ▶). For similar zinc complexes, see: Meyer & Roesky (2007 ▶); Chu et al. (2008 ▶); Szlyk et al. (2005 ▶); Reglinski et al. (2002 ▶).

Experimental

Crystal data

[Zn(C₂₀H₂₂N₂O₄)(H₂O)]
M _r = 437.78
Monoclinic,
a = 13.545 (3) Å
b = 11.550 (2) Å
c = 14.327 (3) Å
β = 115.656 (3)°
V = 2020.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.762, T _max = 0.788
10161 measured reflections
3724 independent reflections
2607 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.085
S = 1.01
3724 reflections
261 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031497/hg5074sup1.cif

e-67-m1220-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031497/hg5074Isup2.hkl

e-67-m1220-Isup2.hkl^{(182.6KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Zn1—O1	1.9737 (19)
Zn1—O2	1.9990 (18)
Zn1—O5	2.040 (2)
Zn1—N2	2.075 (2)
Zn1—N1	2.080 (2)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O3ⁱ	0.85 (1)	2.41 (2)	3.128 (3)	143 (3)
O5—H5A⋯O1ⁱ	0.85 (1)	2.03 (2)	2.781 (3)	147 (3)
O5—H5B⋯O4ⁱ	0.84 (1)	2.42 (2)	3.104 (3)	139 (3)
O5—H5B⋯O2ⁱ	0.84 (1)	1.96 (2)	2.722 (2)	149 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Natural Science Foundation of Zhejiang Province (No. Y407318) and the Applied Research Project on Nonprofit Technology of Zhejiang Province (No. 2010 C32060).

supplementary crystallographic information

Comment

As part of our investigations into Schiff base complexes (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, a new mononuclear zinc(II) complex, Fig. 1. The Zn atom in the complex is five-coordinated by two phenolate O and two imine N atoms of the Schiff base ligand, and by one water O atom, forming a square pyramidal geometry. The Zn atom deviates from the least squares plane defined by the four basal donor atoms by 0.449 (2) Å. The Zn–O and Zn–N bond lengths (Table 1) are typical and are comparable with those observed in other similar zinc(II) complexes (Meyer & Roesky, 2007; Chu et al., 2008; Szlyk et al., 2005; Reglinski et al., 2002).

In the crystal structure, adjacent two molecules are linked via intermolecular O—H···O hydrogen bonds, to form a dimer (Table 1, Fig. 2).

Experimental

3-Ethoxysalicylaldehyde (1.0 mmol, 0.166 g) and ethane-1,2-diamine (0.5 mmol, 0.030 g) were dissolved in MeOH (30 ml), to the mixture was added with stirring an aqueous solution (5 ml) of zinc acetate dihydrate (0.5 mmol, 0.110 g). The final mixture was stirred at room temperature for 10 min to give a clear colorless solution. After keeping the solution in air for a week, colorless block-shaped crystals were formed at the bottom of the vessel.