Bis{2-eth­oxy-6-[2-(methyl­ammonio)ethyl­imino­meth­yl]phenolato}thio­cyanato­zinc(II) nitrate

Chen-Yi Wang; Zhi-Ping Han; Xiang Wu; Cai-Jun Yuan; Jun-Bo Zhou

doi:10.1107/S1600536810000036

. 2010 Jan 9;66(Pt 2):m120. doi: 10.1107/S1600536810000036

Bis{2-ethoxy-6-[2-(methylammonio)ethyliminomethyl]phenolato}thiocyanatozinc(II) nitrate

Chen-Yi Wang ^a,^*, Zhi-Ping Han ^a, Xiang Wu ^a, Cai-Jun Yuan ^a, Jun-Bo Zhou ^a

PMCID: PMC2979686 PMID: 21579607

Abstract

In the title compound, [Zn(NCS)(C₁₂H₁₈N₂O₂)₂]NO₃, the Zn^II ion is chelated by the phenolate O and imine N atoms from two zwitterionic Schiff base ligands and is also coordinated by the N atom of a thiocyanate ligand, giving a distorted trigonal-bipyramidal geometry. Intramolecular N—H⋯O hydrogen bonds are observed in the complex cation. The nitrate anions are linked to the complex cations through N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Zhang & Wang (2007 ▶); Adams et al. (2003 ▶).

Experimental

Crystal data

[Zn(NCS)(C₁₂H₁₈N₂O₂)₂]NO₃
M _r = 630.03
Monoclinic,
a = 10.601 (2) Å
b = 23.335 (3) Å
c = 13.749 (2) Å
β = 112.218 (3)°
V = 3148.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.841, T _max = 0.856
18443 measured reflections
6818 independent reflections
3644 reflections with I > 2σ(I)
R _int = 0.139

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.157
S = 0.91
6818 reflections
365 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.63 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 datablocks global, I. DOI: 10.1107/S1600536810000036/ci5009sup1.cif

e-66-0m120-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000036/ci5009Isup2.hkl

e-66-0m120-Isup2.hkl^{(333.7KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Zn1—O3	1.985 (2)
Zn1—O1	1.999 (3)
Zn1—N6	2.056 (4)
Zn1—N1	2.100 (3)
Zn1—N3	2.104 (3)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3	0.90	1.96	2.750 (4)	145
N2—H2B⋯O4	0.90	2.39	3.078 (4)	133
N4—H4B⋯O1	0.90	1.85	2.697 (4)	157
N4—H4B⋯O2	0.90	2.42	3.027 (5)	125
N2—H2A⋯O7ⁱ	0.90	2.01	2.898 (5)	170
N2—H2A⋯O6ⁱ	0.90	2.52	3.183 (6)	131
N4—H4A⋯O5ⁱⁱ	0.90	2.03	2.894 (5)	160
N4—H4A⋯O7ⁱⁱ	0.90	2.31	3.066 (5)	141

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the Natural Science Foundation of China (grant No. 30771696), the Natural Science Foundation of Zhejiang Province (grant No. Y407318) and the Science and Technology Plan of Huzhou (grant No. 2009 GG06).

supplementary crystallographic information

Comment

As part of our investigations into novel urease inhibitors, we have synthesized the title compound, a new Zn^II complex. The compound consists of a mononuclear zinc(II) complex cation and a nitrate anion. The Zn atom is chelated by the phenolate O and imine N atoms from two Schiff base ligands, and is coordinated by the N atom from a thiocyanate ligand, forming a trigonal-bipyramid geometry (Fig. 1). The coordinate bond lengths (Table 1) and angles are typical and are comparable with those observed in other similar zinc(II) complexes (Zhang & Wang, 2007; Adams et al., 2003). The amine N atoms of the Schiff base ligands are protonated and take no part in the coordination to the Zn^II ion.

Experimental

3-Ethoxysalicylaldehyde (0.2 mmol, 33.2 mg) and N-methylethane-1,2-diamine (0.2 mmol, 14.8 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. To this solution was added an aqueous solution (2 ml) of ammonium thiocyanate (0.2 mmol, 15.2 mg) and an aqueous solution (3 ml) of Zn(NO₃)₂.6H₂O (0.1 mmol, 29.0 mg) with stirring. The resulting mixture was stirred for another 10 min at room temperature. After keeping the filtrate in air for a week, colourless block-shaped crystals were formed at the bottom of the vessel.