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

Hui-Rui Guo

doi:10.1107/S1600536808029590

. 2008 Sep 20;64(Pt 10):m1288–m1289. doi: 10.1107/S1600536808029590

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

Hui-Rui Guo ^a,^*

PMCID: PMC2959439 PMID: 21201033

Abstract

The title complex, [Zn(NCS)(C₁₃H₂₀N₂O₂)₂]NO₃, consists of a complex mononuclear Zn^II cation and a nitrate counter-anion. The Zn^II ion is five-coordinate in a trigonal-bipyramidal geometry. The thiocyanate N atom and two O atoms from two Schiff bases define the equatorial plane, and the two imine N atoms from the same two Schiff bases occupy the axial positions, with an N—Zn—N angle of 175.98 (7)°. The amine N atoms of the Schiff base ligands are protonated and are not involved in the coordination to the metal. The dihedral angle between the two substituted benzene rings is 87.7 (2)°. The nitrate counter-ions are linked to the cations through N—H⋯O hydrogen bonds.

Related literature

For background on Schiff base complexes, see: Samanta et al. (2007 ▶); Ghosh et al. (2006 ▶); Correia et al. (2006 ▶); Cai et al. (2006 ▶); Zhang et al. (2007 ▶). For Zn^II complexes with biological properties, see: Berg & Shi (1996 ▶); Tarafder et al. (2002 ▶); Osowole et al. (2008 ▶); Chohan & Kausar (1993 ▶). For related structures, see: Eltayeb et al. (2008 ▶); Odoko et al. (2006 ▶); Tatar et al. (2002 ▶).

Experimental

Crystal data

[Zn(NCS)(C₁₃H₂₀N₂O₂)₂]NO₃
M _r = 658.08
Monoclinic,
a = 12.619 (3) Å
b = 15.596 (3) Å
c = 16.373 (4) Å
β = 105.942 (3)°
V = 3098.5 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 298 (2) K
0.32 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.759, T _max = 0.784
25309 measured reflections
6704 independent reflections
4943 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.102
S = 1.03
6704 reflections
383 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.24 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/S1600536808029590/bh2194sup1.cif

e-64-m1288-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029590/bh2194Isup2.hkl

e-64-m1288-Isup2.hkl^{(328.1KB, 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
N2—H2B⋯O5	0.90	1.96	2.843 (3)	166
N2—H2A⋯O3	0.90	1.98	2.772 (2)	146
N2—H2A⋯O4	0.90	2.37	3.022 (3)	129
N4—H4A⋯O7ⁱ	0.90	2.22	3.050 (3)	153
N4—H4A⋯O5ⁱ	0.90	2.50	3.080 (3)	122
N4—H4B⋯O1	0.90	1.71	2.606 (2)	171
N4—H4B⋯O2	0.90	2.55	3.051 (3)	116

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge Yichun University for support of this research.

supplementary crystallographic information

Comment

The synthesis and structural investigation of Schiff base complexes have attracted much attention due to their interesting structures and wide potential applications (Samanta et al., 2007; Ghosh et al., 2006; Correia et al., 2006; Cai et al., 2006; Zhang et al., 2007). Zn^II complexes play an important role in biological systems (Berg & Shi, 1996; Tarafder et al., 2002; Osowole et al., 2008; Chohan & Kausar, 1993). In this paper, the crystal structure of a new Zn^II complex, (I), with the Schiff base 2-ethoxy-6-[(2-ethylammonioethylimino)methyl]phenol and thiocyanate as ligands is reported.

The asymmetric unit of (I) (Fig. 1) consists of a mononuclear Zn^II complex cation and a nitrate counteranion. The Zn^II ion is five-coordinate in a trigonal-bipyramidal geometry, with one thiocyanate N atom and two O atoms from two Schiff bases defining the base-plane, and with two imine N atoms from two Schiff bases occupying the axial positions. The coordination bond lengths and angles (Table 1) are comparable with those found in related structures (Eltayeb et al., 2008; Odoko et al., 2006; Tatar et al., 2002). The dihedral angle between the two substituted benzene rings is 87.7 (2)°. The nitrate counterions are linked to the complex cations through intermolecular N—H···O hydrogen bonds (Table 2, Fig. 2).

Experimental

The Schiff base was synthesized by condensing N-ethylethane-1,2-diamine with 3-ethoxysalicylaldehyde. The compound (0.236 g, 1.0 mmol), ammonium thiocyanate (0.076 g, 1.0 mmol), and Zn(NO₃)₂.6H₂O (0.297 g, 1.0 mmol) were heated in ethanol (30 ml) for two hours. The resulting yellow precipitate was washed with cold ethanol and dried in air. Yellow single crystals of the complex suitable for X-ray diffraction were obtained by recrystallization in methanol at room temperature over a week.