Poly[bis­[μ2-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro­pyrido[2,3-d]pyrimidine-6-carboxyl­ato]nickel(II)]

Zhe An; Ling Zhu

doi:10.1107/S1600536809055408

. 2010 Jan 9;66(Pt 2):m123. doi: 10.1107/S1600536809055408

Poly[bis[μ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]nickel(II)]

Zhe An ^a,^*, Ling Zhu ^a

PMCID: PMC2979888 PMID: 21579609

Abstract

The title compound, [Ni(C₁₄H₁₆N₅O₃)₂]_n or [Ni(ppa)₂]_n, where ppa is 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate, was synthesized under hydrothermal conditions. The Ni^II atom (site symmetry Inline graphic ) exhibits a distorted trans-NiN₂O₄ octahedral geometry defined by two monodentate N-bonded and two bidentate O,O′-bonded ppa monoanions. The extended two-dimensional structure is a square grid. An intermolecular N—H⋯O hydrogen bond occurs.

Related literature

For manganese, cobalt and zinc complexes of the ppa anion, see: Huang et al. (2008 ▶); Xu et al. (2009 ▶); Qi et al. (2009 ▶), respectively. For background to the medicinal uses of pipemidic acid, see: Mizuki et al. (1996 ▶).

Experimental

Crystal data

[Ni(C₁₄H₁₆N₅O₃)₂]
M _r = 663.35
Monoclinic,
a = 6.1249 (6) Å
b = 21.250 (2) Å
c = 12.5511 (12) Å
β = 101.846 (2)°
V = 1598.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 296 K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.764, T _max = 0.868
7593 measured reflections
2762 independent reflections
2389 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.199
S = 1.00
2762 reflections
209 parameters
1 restraint
H-atom parameters not refined
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536809055408/hb5292sup1.cif

e-66-0m123-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055408/hb5292Isup2.hkl

e-66-0m123-Isup2.hkl^{(135.6KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Ni1—O2	2.013 (3)
Ni1—O1	2.051 (3)
Ni1—N5ⁱ	2.207 (3)

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Symmetry code: (i) Inline graphic .

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯O3ⁱⁱ	0.90 (4)	2.29 (4)	3.161 (5)	163 (5)

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Symmetry code: (ii) Inline graphic .

Acknowledgments

The authors acknowledge financial support from the program for talent introduction in Guangdong Higher Education Institutions (grant No. 201191) and the scientific research start-up funds for talent introduction in Maoming University (grant No. 208058).

supplementary crystallographic information

Comment

Pipemidic acid (Hppa, C₁₄H₁₆N₅O₃, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3-d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The manganese, cobalt and zinc complexes of the ppa anion have been reported (Huang et al., 2008; Xu et al. 2009; Qi Xu et al.2009). The title nickel(II) complex, (I), is reported here (Fig. 1).

The nickel(II) atom is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (Fig. 2).

Experimental

A mixture of Ni(CH₃COO)₂.4H₂O (0.063 g, 0.25 mmol), Hppa (0.15 g, 0.5 mmol), sodium hydroxide (0.04 g, 1 mmol) and water (15 ml) was stirred for 30 min in air. The mixture was then transferred to a 25 ml Teflon-lined hydrothermal bomb. The bomb was kept at 443 K for 72 h under autogenous pressure. Upon cooling, green prisms of (I) were obtained from the reaction mixture.