Dibromido{2-[2-(piperidinium-1-yl)ethyl­imino­meth­yl]phenolato}zinc(II) monohydrate

Yi-Jun Wei; Feng-Wu Wang; Qi-Yong Zhu

doi:10.1107/S1600536808015730

. 2008 Jun 7;64(Pt 7):m859–m860. doi: 10.1107/S1600536808015730

Dibromido{2-[2-(piperidinium-1-yl)ethyliminomethyl]phenolato}zinc(II) monohydrate

Yi-Jun Wei ^a,^*, Feng-Wu Wang ^a, Qi-Yong Zhu ^a

PMCID: PMC2961651 PMID: 21202736

Abstract

The asymmetric unit of the title compound, [ZnBr₂(C₁₄H₂₀N₂O)]·H₂O, consists of a mononuclear Schiff base zinc(II) complex molecule and a solvent water molecule. The Zn^II atom is four-coordinated in an approximately tetrahedral geometry, binding to the imine N and phenolate O atoms of the neutral zwitterionic Schiff base ligand and to two terminal Br⁻ anions. In the crystal structure, molecules are linked through intermolecular O—H⋯Br and O—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For the background to Schiff base zinc(II) complexes, see: Bhosekar et al. (2006 ▶); Chisholm et al. (2001 ▶); Jian et al. (2004 ▶); Lacroix et al. (1996 ▶); Tatar et al. (2002 ▶). For related structures, see: Ma, Gu et al. (2006 ▶); Ma, Lv et al. (2006 ▶); Peng & Hou (2006 ▶); Peng et al. (2006 ▶); Wei et al. (2007 ▶); Zhang et al. (2008 ▶); Zhu et al. (2007 ▶).

Experimental

Crystal data

[ZnBr₂(C₁₄H₂₀N₂O)]·H₂O
M _r = 475.53
Triclinic,
a = 9.2997 (18) Å
b = 10.1776 (17) Å
c = 11.1667 (18) Å
α = 71.510 (2)°
β = 71.215 (2)°
γ = 67.571 (2)°
V = 901.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 5.80 mm⁻¹
T = 298 (2) K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.390, T _max = 0.422 (expected range = 0.326–0.352)
5468 measured reflections
3983 independent reflections
2891 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.091
S = 1.02
3983 reflections
199 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536808015730/sj2508sup1.cif

e-64-0m859-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015730/sj2508Isup2.hkl

e-64-0m859-Isup2.hkl^{(195.2KB, hkl)}

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

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

Zn1—O1	1.936 (2)
Zn1—N1	2.024 (3)
Zn1—Br1	2.3417 (7)
Zn1—Br2	2.3991 (7)

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O1—Zn1—N1	93.91 (11)
O1—Zn1—Br1	116.12 (8)
N1—Zn1—Br1	113.04 (8)
O1—Zn1—Br2	109.78 (8)
N1—Zn1—Br2	108.84 (9)
Br1—Zn1—Br2	113.42 (2)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.90 (4)	1.89 (4)	2.777 (4)	169 (4)
O2—H2A⋯Br2ⁱ	0.85 (4)	2.57 (4)	3.399 (3)	165 (4)
O2—H2B⋯O1ⁱⁱ	0.86 (3)	1.93 (4)	2.762 (4)	165 (5)

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

Acknowledgments

The authors thank the Education Office of Anhui Province, People’s Republic of China, for research grant No. KJ2007A126ZC.

supplementary crystallographic information

Comment

Zinc(II) complexes derived from Schiff base ligands have been studied extensively due to their interesting structures and wide applications (Lacroix et al., 1996; Chisholm et al., 2001; Jian et al., 2004; Tatar et al., 2002; Bhosekar et al., 2006). Recently, we have reported two Schiff base zinc(II) complexes with bromide ligands (Wei et al., 2007; Zhu et al., 2007). As a continuation of our work on the structures of such complexes, we report herein the crystal structure of the new title complex, (I), which is isostructural with the zinc(II) complex with chloride ligands (Zhang et al., 2008).

The tetrahedral coordination sphere of Zn^II atom in (I) is formed by the imine N and phenolate O atoms of the Schiff base ligand and by two terminal Br^- anions (Fig. 1). The coordinate bond distances (Table 1) are typical and comparable with the values in other similar zinc(II) complexes (Peng & Hou, 2006; Peng et al., 2006; Ma, Gu et al., 2006; Ma, Lv et al., 2006). The O1—Zn1—N1 and O1—Zn1—Br1 bond angles deviate most from ideal tetrahedral geometry with values of 93.91 (11) and 116.12 (8)°, respectively. The other angles in the coordination sphere are in the range 108.84 (9)–113.42 (2)° (Table 1).

In the crystal structure of (I), molecules are linked through intermolecular O—H···Br and O—H···O hydrogen bonds (Table 2), forming chains running along the b axis (Fig. 2).

Experimental

Compound (I) was obtained by stirring of salicylaldehyde (0.1 mmol, 12.2 mg), 2-piperidin-1-ylethylamine (0.1 mmol, 12.8 mg), and zinc(II) bromide (0.1 mmol, 22.5 mg) in methanol (20 ml) for 30 min at room temperature. The reaction mixture was fitered. Yellow block-shaped single crystals suitable for X-ray diffraction formed from the filtrate after one day.