{(E)-2-[3-(Dimethyl­ammonio)propyl­iminometh­yl]phenolato}diiodidozinc(II)

Xue-Wen Zhu; Xu-Zhao Yang

doi:10.1107/S1600536808023659

. 2008 Jul 31;64(Pt 8):m1090–m1091. doi: 10.1107/S1600536808023659

{(E)-2-[3-(Dimethylammonio)propyliminomethyl]phenolato}diiodidozinc(II)

Xue-Wen Zhu ^a,^*, Xu-Zhao Yang ^a

PMCID: PMC2961998 PMID: 21203068

Abstract

The title complex, [ZnI₂(C₁₂H₁₈N₂O)], is a mononuclear zinc(II) compound derived from the zwitterionic form of the Schiff base (E)-2-[(3-dimethylaminopropylimino)methyl]phenol. The Zn^II atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two iodide ions in a tetrahedral coordination geometry. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008 ▶); Biswas et al. (2008 ▶); Chen et al. (2008 ▶); Darensbourg & Frantz (2007 ▶); Habibi et al. (2007 ▶); Kawamoto et al. (2008 ▶); Lipscomb & Sträter (1996 ▶); Tomat et al. (2007 ▶); Wu et al. (2008 ▶); Yuan et al. (2007 ▶). For related structures, see: Qiu (2006a ▶,b ▶); Wei et al. (2007 ▶); Zhu et al. (2007 ▶).

Experimental

Crystal data

[ZnI₂(C₁₂H₁₈N₂O)]
M _r = 525.45
Orthorhombic,
a = 13.892 (3) Å
b = 16.640 (2) Å
c = 7.372 (3) Å
V = 1704.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 5.06 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.431, T _max = 0.463 (expected range = 0.375–0.402)
12154 measured reflections
3669 independent reflections
3271 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.100
S = 1.04
3669 reflections
165 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.82 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ▶), 1660 Friedel pairs
Flack parameter: 0.00 (4)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536808023659/sj2522sup1.cif

e-64-m1090-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023659/sj2522Isup2.hkl

e-64-m1090-Isup2.hkl^{(179.9KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Zn1—O1	1.952 (4)
Zn1—N1	2.010 (6)
Zn1—I2	2.5550 (11)
Zn1—I1	2.5615 (11)

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O1—Zn1—N1	94.3 (2)
O1—Zn1—I2	112.17 (16)
N1—Zn1—I2	113.02 (16)
O1—Zn1—I1	112.90 (16)
N1—Zn1—I1	106.74 (18)
I2—Zn1—I1	115.67 (4)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.91	1.91	2.772 (8)	157

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Schiff bases have widely been used as versatile ligands in coordination chemistry (Biswas et al., 2008; Wu et al., 2008; Kawamoto et al., 2008; Ali et al., 2008; Habibi et al., 2007), and their metal complexes are of great interest in many fields (Chen et al., 2008; Yuan et al., 2007; Tomat et al., 2007; Darensbourg & Frantz, 2007). Zinc(II) is an important element in biological systems and functions as the active site of hydrolytic enzymes, such as carboxypeptidase and carbonic anhydrase where it is in a hard-donor coordination environment of nitrogen and oxygen ligands (Lipscomb & Sträter, 1996). In this paper, a new zinc(II) complex, (I), Fig. 1, of the Schiff base ligand (E)-2-[(3-dimethylaminopropylimino)methyl]phenol has been synthesized and structurally characterized.

The Zn^II atom in (I) is four-coordinated by the imine N and phenolate O atoms of the zwitterionic form of the Schiff base ligand, and by two I^- ions, in a tetrahedral coordination geometry. The coordinate bond lengths (Table 1) are typical and comparable to the corresponding values observed in other similar zinc(II) Schiff base complexes (Zhu et al., 2007; Wei et al., 2007; Qiu, 2006a,b).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 2), forming chains running along the b axis (Fig. 2).

Experimental

The Schiff base compound was prepared by the condensation of equimolar amounts of salicylaldehyde with N,N-dimethylpropane-1,3-diamine in a methanol solution. The complex was prepared by the following method. To an anhydrous methanol solution (5 ml) of ZnI₂ (31.9 mg, 0.1 mmol) was added a methanol solution (10 ml) of the Schiff base compound (20.6 mg, 0.1 mmol) with stirring. The mixture was stirred for 30 min at room temperature and filtered. Upon keeping the filtrate in air for a few days, colorless block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.