Diiodido{2-(morpholin-4-yl)-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3 N,N′,N′′}zinc

Nura Suleiman Gwaram; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536811014656

. 2011 Apr 22;67(Pt 5):m628. doi: 10.1107/S1600536811014656

Diiodido{2-(morpholin-4-yl)-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³ N,N′,N′′}zinc

Nura Suleiman Gwaram ^a, Hamid Khaledi ^a,^*, Hapipah Mohd Ali ^a

PMCID: PMC3089331 PMID: 21754337

Abstract

In the title compound, [ZnI₂(C₁₃H₁₉N₃O)], the Zn^II ion is five-coordinated in a distorted square-pyramidal geometry, in which the basal plane is defined by three N atoms from the Schiff base ligand and one iodide ion. A second iodide ligand, situated in the apical position, completes the coordination geometry. In the crystal structure, C—H⋯O hydrogen bonds link a pair of molecules around an inversion centre into a dimer.

Related literature

For the structure of an analogous ZnCl₂ complex, see: Ikmal Hisham et al. (2011 ▶). For square-pyramidal ZnI₂ complexes with N,N′,N′′-tridentate ligands, see: Drew & Hollis (1978 ▶); Yousefi (2010 ▶). For a description of the geometry of complexes with five-coordinated metal ions, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[ZnI₂(C₁₃H₁₉N₃O)]
M _r = 552.48
Triclinic,
a = 8.8874 (3) Å
b = 10.3117 (4) Å
c = 10.3643 (4) Å
α = 68.8810 (18)°
β = 81.959 (2)°
γ = 66.3990 (17)°
V = 811.91 (6) Å³
Z = 2
Mo Kα radiation
μ = 5.31 mm⁻¹
T = 100 K
0.17 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.465, T _max = 0.646
7292 measured reflections
3517 independent reflections
3260 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.018
wR(F ²) = 0.045
S = 1.05
3517 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −1.23 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014656/hy2422sup1.cif

e-67-0m628-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014656/hy2422Isup2.hkl

e-67-0m628-Isup2.hkl^{(172.4KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Zn1—N1	2.205 (2)
Zn1—N2	2.093 (2)
Zn1—N3	2.269 (2)
Zn1—I1	2.6018 (4)
Zn1—I2	2.6506 (4)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.99	2.55	3.491 (3)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant No. FP004/2010B).

supplementary crystallographic information

Comment

The title compound (Fig. 1) was obtained via the complexation of Zn^II ion with the in situ prepared Schiff base, 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine, and two iodide ions. Similar to what was observed in an analogous ZnCl₂ complex (Ikmal Hisham et al., 2011), the Schiff base acts as an N,N',N''-tridentate chelate ligand, along with two halide ligands, make a distorted square-pyramidal geometry around the metal ion (τ = 0.24, Addison et al., 1984). The Zn—I and Zn—N interatomic distances (Table 1) are comparable to the values reported for similar structures (Drew & Hollis, 1978; Yousefi, 2010). In the crystal, a pair of the molecules, related by a symmetry operation -x + 1, -y + 2, -z + 2, are linked through C—H···O hydrogen bonds into a centrosymmetric dimer (Table 2).

Experimental

A mixture of 2-acetylpyridine (0.20 g, 1.65 mmol) and 4-(2-aminoethyl)morpholine (0.21 g, 1.65 mmol) in ethanol (20 ml) was refluxed for 2 h, followed by addition of a solution of zinc(II) acetate dihydrate (0.36 g, 1.65 mmol) and potassium iodide (0.54 g, 3.3 mmol) in a minimum amount of water. The resulting solution was refluxed for 30 min and then left at room temperature. Brown crystals of the title complex were obtained in a few days.