(5,5′-Dimethyl-2,2′-bipyridine-κ2 N,N′)(1-naphthyl­acetato-κO)(1-naphthyl­acetato-κ2 O,O′)zinc hemihydrate

Li-Li Ji; Jian-She Liu; Wen-Dong Song

doi:10.1107/S1600536811013353

. 2011 Apr 16;67(Pt 5):m606. doi: 10.1107/S1600536811013353

(5,5′-Dimethyl-2,2′-bipyridine-κ² N,N′)(1-naphthylacetato-κO)(1-naphthylacetato-κ² O,O′)zinc hemihydrate

Li-Li Ji ^a, Jian-She Liu ^a,^*, Wen-Dong Song ^b

PMCID: PMC3089144 PMID: 21754324

Abstract

In the title compound, [Zn(C₁₂H₉O₂)₂(C₁₂H₁₂N₂)]·0.5H₂O, the water molecule lies on a twofold rotation axis. The Zn^II atom is coordinated by three O atoms from two 1-naphthylacetate ligands, one monodentate and the other asymmetric bidentate chelate, and two N atoms from a 5,5′-dimethyl-2,2′-bipyridine ligand, giving an irregular environment. In the crystal, the complex molecules are interlinked through the water molecule by O—H⋯O_carboxylate hydrogen bonds, together with weak C—H⋯O and bipyridine ring π–π stacking interactions [ring centroid separation = 3.761 (2) Å], giving a two-dimensional network structure.

Related literature

For background to self-assembly of supramolecular architectures based on naphthylcarboxylate ligands, see: Kong et al. (2009 ▶); Li et al. (2009 ▶). The Zn—O distance in the second ligand [2.417 (3) Å] suggests a non-negligible (bidentate) interaction, see: Guilera & Steed (1999 ▶).

Experimental

Crystal data

[Zn(C₁₂H₉O₂)₂(C₁₂H₁₂N₂)]·0.5H₂O
M _r = 629.00
Monoclinic,
a = 32.212 (7) Å
b = 8.2668 (17) Å
c = 25.314 (5) Å
β = 117.865 (4)°
V = 5959 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.87 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.756, T _max = 0.819
21468 measured reflections
5325 independent reflections
3566 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.106
S = 0.99
5325 reflections
395 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013353/zs2105sup1.cif

e-67-0m606-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013353/zs2105Isup2.hkl

e-67-0m606-Isup2.hkl^{(260.8KB, 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
O5—H5⋯O1	0.82	2.21	2.948 (3)	150
C8—H8A⋯O4ⁱ	0.93	2.59	3.515 (6)	171

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge Donghua University for supporting this work.

supplementary crystallographic information

Comment

Self-assembly of supramolecular architectures based on naphthylcarboxylate ligands has attracted much attention during recent decades (Kong et al., 2009; Li et al., 2009). However, to our knowledge, 1-naphthylacetic acid has not been used as a potential building block in the construction of supramolecular architectures. Herein we report the structure of the title compound, the mixed ligand complex [(C₁₂H₁₂N₂)(C₁₂H₉O₂)₂]₂ . 0.5H₂O (I), from the reaction of zinc nitrate with 1-naphthylacetic acid and 5,5'-dimethyl-2,2'-bipyridyrine in a basic aqueous solution.

The asymmetric unit in (I) (Fig. 1) consists of one Zn^II complex unit and a water molecule which lies on a two-fold rotation axis (Fig. 1). The five-coordinate Zn centre comprises three O atoms from two 1-naphthylacetate ligands and two N atoms from a 5,5'-dimethyl-2,2'-bipyridyrine ligand. There are two coordination modes for the 1-naphthylacetate ligands in the structure: one monodentate the other asymmetric bidentate chelate. The Zn1-O4 distance in the second ligand [2.417 (3) Å] suggests a non-negligible (bidentate) interaction (Guilera & Steed, 1999) whereas the Zn1—O5 distance in the first ligand [2.587 (3)] is considered beyond the distance maximum for a bidentate interaction. In the crystal, the supramolecular network is stabilized by water O—H···O_carboxyl, hydrogen bonds together with weak intermolecular aromatic C8—H···O_carboxyl interactions (Table 1), giving a two-dimensional network structure. In addition the inter-ring separation between the pyridine rings of two adjacent 5,5'-dimethyl-2,2'-bipyridine ligands is 3.761 (2) Å, indicating weak π-π stacking interactions (Fig. 2).

Experimental

A mixture of 1-naphthylacetic acid (0.110 g, 0.5 mmol), 5,5'-dimethyl-2,2'-bipyridine (0.092 g, 0.5 mmol), zinc nitrate hexahydrate (0.075 g, 0.25 mmol), NaOH (0.08 g, 0.2 mmol) and water (10 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 423 K for 3 days, and then cooled to room temperature at a rate of 10 K h^-1. The colorless crystals obtained were washed with water and dried in air (yield 47% based on zinc).