catena-Poly[[bis­(2-hydr­oxy-2-phenyl­acetato-κ2 O 1,O 2)zinc(II)]-μ-1,2-di-4-pyridylethane-κ2 N:N′]

Seung Man Yu; Dong Hoon Shin; Pan-Gi Kim; Cheal Kim; Youngmee Kim

doi:10.1107/S1600536809030281

. 2009 Aug 8;65(Pt 9):m1045–m1046. doi: 10.1107/S1600536809030281

catena-Poly[[bis(2-hydroxy-2-phenylacetato-κ² O ¹,O ²)zinc(II)]-μ-1,2-di-4-pyridylethane-κ² N:N′]

Seung Man Yu ^a, Dong Hoon Shin ^a, Pan-Gi Kim ^b,^*, Cheal Kim ^a, Youngmee Kim ^c,^*

PMCID: PMC2969950 PMID: 21577407

Abstract

The title compound, [Zn(C₈H₆O₃)₂(C₁₂H₁₂N₂)]_n, consists of [Zn(Hopa)₂] (H₂opa = 2-hydroxy-2-phenylacetic acid or mandelic acid) units bridged by 1,2-di-4-pyridylethane (bpe) ligands, forming a polymeric chain developing parallel to the b axis. The bridging bpe ligand is arranged around a twofold axis passing through the middle of the ethane C—C bond. The geometry around the Zn^II ion is distorted octahedral, constructed by four O atoms from two Hopa⁻ ligands and two N atoms from two bridging bpe ligands. O—H⋯O hydrogen bonds link the chains, forming a three-dimensional network.

Related literature

Transition metal ions are the major cationic contributors to the inorganic composition of natural water and biological fluids, see: Daniele et al. (2008 ▶). For related structures, see: Balboa et al. (2008 ▶); Beghidja et al. (2005 ▶); Hao et al. (2009 ▶); Lee et al. (2008 ▶); Park et al. (2008 ▶); Shin et al. (2009 ▶); Wermester et al. (2007 ▶); Yu et al. (2008 ▶).

Experimental

Crystal data

[Zn(C₈H₆O₃)₂(C₁₂H₁₂N₂)]
M _r = 551.90
Hexagonal,
a = 11.1360 (6) Å
c = 33.110 (3) Å
V = 3555.9 (4) Å³
Z = 6
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 293 K
0.10 × 0.05 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.933, T _max = 0.944
17715 measured reflections
2347 independent reflections
2045 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.068
S = 1.04
2347 reflections
168 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 870 Friedel pairs
Flack parameter: −0.002 (16)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030281/dn2478sup1.cif

e-65-m1045-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030281/dn2478Isup2.hkl

e-65-m1045-Isup2.hkl^{(113.1KB, 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
O13—H13O⋯O12ⁱ	0.85	1.77	2.619 (3)	173

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Korea Ministry of the Environment ‘ET-Human Resource Development Project’ and the Cooperative Research Program for Agricultural Science & Technology Development (20070301–036-019–02) is gratefully acknowledged.

supplementary crystallographic information

Comment

A great attention has been paid to transition metal ions as the major cation contributors to the biologically active molecules such as amino acids, proteins, sugars, nucleotides etc (Daniele, et al., 2008). This interest has driven us to study on the interaction of the transition metal ions with fulvic acids or humic acids. As models to examine the interaction, therefore, we have previously used copper(II) and zinc(II) benzoates as building blocks and reported the structures of copper(II) and zinc(II) benzoates with quinoxaline, 6-methylquinoline, 3-methylquinoline, and di-2-pyridyl ketone(Lee et al., 2008; Yu et al., 2008; Park et al., 2008; Shin et al., 2009).

Mandelic acid (2-hydroxy-2-phenylacetic acid, H₂opa) is also one of the simplest bioactive molecules exhibiting a variety of coordinating and supramolecular interaction abilities (Balboa et al., 2008; Beghidja et al.,2005; Hao et al., 2009; Wermester et al., 2007). In order to study the interaction of the biologically active molecule mandelic acid with zinc(II) ion, in the present work, we have employed zinc(II) mandelate as a building block and 1,2-di-4-pyridylethane (bpe) as a ligand. We report herein the structure of new zinc(II) mandelate with 1,2-di-4-pyridylethane.

The crystal structure contains [Zn(Hopa)₂] units bridged by bpe ligands forming a polymeric chain developping parallel to the b axis. The bridging 1,2-di-4-pyridylethane (bpe) ligand is arranged around a two fold axis going through the middle of C26—C26ⁱⁱ bond (symmetry code: (ii) x, x-y+2, -z+1/6). The geometry around the Zn^II ion is distorted octahedral constructed by four oxygen atoms from two Hopa^- and two nitrogen atoms from two bridging bpe ligands (Fig. 1). The occurence of O-H···O hydrogen bonds links the chains to form a three dimensionnal network.

Experimental

38.0 mg (0.125 mmol) of Zn(NO₃)₂^.6H₂O and 38.4 mg (0.25 mmol) of 2-hydroxy-2-phenylacetic acid were dissolved in 4 ml water and carefully layered by 4 ml solution of a mixture of acetone, methanol and ethanol (2/2/2) of 1,2-di-4-pyridylethane ligand (46.0 mg, 0.25 mmol). Suitable crystals of the title compoundfor X-ray analysis were obtained in a few weeks.