{4-Bromo-2-[(2-morpholinoeth­yl)imino­meth­yl]phenolato}iodido(methanol)zinc(II)

Cheng-Li Han

doi:10.1107/S1600536809009234

. 2009 Mar 19;65(Pt 4):m418. doi: 10.1107/S1600536809009234

{4-Bromo-2-[(2-morpholinoethyl)iminomethyl]phenolato}iodido(methanol)zinc(II)

Cheng-Li Han ^a,^*

PMCID: PMC2968908 PMID: 21582360

Abstract

The title compound, [Zn(C₁₃H₁₆BrN₂O₂)I(CH₃OH)], is a new mononuclear zinc(II) complex synthesized by the reaction of equimolar quantities of 5-bromosalicylaldehyde, 2-morpholinoethylamine and ZnI₂ in methanol. The Zn atom is four-coordinate in a distorted tetrahedral geometry, binding to a phenolate O and an imine N atom of the Schiff base ligand, the O atom of a methanol molecule and one I⁻ anion. In the crystal structure, adjacent molecules are linked through intermolecular O—H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For the structures of related zinc(II) complexes, see: Ali et al. (2008 ▶); You (2005 ▶); Zhu & Yang (2008 ▶).

Experimental

Crystal data

[Zn(C₁₃H₁₆BrN₂O₂)I(CH₄O)]
M _r = 536.50
Monoclinic,
a = 7.747 (2) Å
b = 24.977 (3) Å
c = 9.598 (2) Å
β = 100.497 (4)°
V = 1826.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 5.24 mm⁻¹
T = 298 K
0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.217, T _max = 0.231
12877 measured reflections
3928 independent reflections
2994 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.096
S = 1.03
3928 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.71 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/S1600536809009234/sj2595sup1.cif

e-65-0m418-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009234/sj2595Isup2.hkl

e-65-0m418-Isup2.hkl^{(192.6KB, hkl)}

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

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

Zn1—N1	2.014 (3)
Zn1—O3	2.023 (3)
Zn1—O1	2.078 (3)
Zn1—I1	2.5346 (9)

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N1—Zn1—O3	114.78 (13)
N1—Zn1—O1	90.15 (12)
O3—Zn1—O1	90.42 (13)
N1—Zn1—I1	130.76 (10)
O3—Zn1—I1	113.36 (9)
O1—Zn1—I1	99.31 (9)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.84 (5)	1.81 (5)	2.649 (4)	178 (7)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges a research grant from Qiqihar University.

supplementary crystallographic information

Comment

Metal complexes of the Schiff base 4-bromo-2-[(2-morpholinoethylimino)methyl]phenol have not been reported previously. In this paper, the author reports the crystal structure of the title compound, a new mononuclear zinc(II) complex, (I), Fig. 1.

In (I), the Zn atom is four-coordinate in a tetrahedral geometry, with one O and one imine N atoms of a Schiff base ligand, one O atom of a methanol molecule, and one I atom. The tetrahedral geometry is severely distorted, as evidenced by the coordinate bond lengths and angles (Table 1). The bond lengths and angles in this complex are comparable with those in the similar zinc(II) complexes (Ali et al., 2008; You, 2005; Zhu & Yang, 2008). In the crystal structure, adjacent molecules are linked through intermolecular O–H···O hydrogen bonds (Table 2), forming centrosymmetric dimers (Fig. 2).

Experimental

Equimolar quantities (1.0 mmol each) of 5-bromosalicyaldehyde, 2-morpholinoethylamine, and ZnI₂ were mixed in methanol. The mixture was stirred at reflux for 30 min and filtered. The filtrate was slowly evaporated for a few days, yielding yellow block-like crystals.