Poly[bis­[μ-1-cyclo­propyl-6-fluoro-4-oxido-7-(1-piperazin­yl)-1,4-dihydro­quinoline-3-carboxyl­ato]nickel(II)]

Zhe An; Lan-Ru Liu; Ya-Qin Liu

doi:10.1107/S1600536807065555

. 2007 Dec 12;64(Pt 1):m176. doi: 10.1107/S1600536807065555

Poly[bis[μ-1-cyclopropyl-6-fluoro-4-oxido-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylato]nickel(II)]

Zhe An ^a, Lan-Ru Liu ^a, Ya-Qin Liu ^b,^*

PMCID: PMC2915111 PMID: 21200524

Abstract

In the title compound, [Ni(C₁₇H₁₇FN₃O₃)₂]_n, the Ni^II atom exists in a distorted trans-NiN₂O₄ octahedral geometry defined by two monodentate N-bonded and two bidentate O,O-bonded 1-cyclopropyl-6-fluoro-4-oxido-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylate (ciprofloxacinium) monoanions. The extended two-dimensional structure is a square grid. The Ni atom lies on a center of inversion.

Related literature

For the manganese, zinc and copper complexes of the ciprofloxacinium (cf) anion, see: Xiao et al. (2005 ▶); An et al. (2007 ▶). For background on the medicinal uses of Hcf, see: Mizuki et al. (1996 ▶).

Experimental

Crystal data

[Ni(C₁₇H₁₇FN₃O₃)₂]
M _r = 719.38
Monoclinic,
a = 5.9999 (6) Å
b = 21.437 (2) Å
c = 13.2287 (14) Å
β = 101.886 (2)°
V = 1665.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 295 (2) K
0.34 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.810, T _max = 0.892
8098 measured reflections
2890 independent reflections
2466 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.173
S = 1.00
2890 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.92 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065555/cs2060sup1.cif

e-64-0m176-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065555/cs2060Isup2.hkl

e-64-0m176-Isup2.hkl^{(141.9KB, 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
N3—H3N⋯O2ⁱ	0.861 (10)	2.48 (4)	3.184 (4)	139 (5)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support by the Science Foundation of Qiqihar Medical University (grant No. 20044405).

supplementary crystallographic information

Comment

Ciprofloxacin (1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo -7-(1-piperazinyl)-3-quinoline carboxylic acid, H-cf) is a member of a class of quinolones that is used to treat infections (Mizuki et al., 1996). Manganese(II), zinc(II) and copper(II) derivatives of H-cf have been reported (Xiao et al., 2005; An et al., 2007). The title compound nickel(II) derivative is a two-dimensional coordination polymer in which the anion acts in a bridging mode (Fig. 1).

The Ni(II) atom is coordinated by four oxygen atoms and two N atoms from four cf ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating approximately in the bc plane (Fig. 2).

Experimental

A mixture of Ni(NO₃)₂.6H₂O (0.07 g, 0.25 mmol), ciprofloxacin hydrochloride (0.19 g, 0.5 mmol), and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Green single crystals of the title compound suitable for X-ray analysis were obtained from the reaction mixture after cooling. Green blocks of (I) with a yield of 21%. Anal. Calc. for C₃₄H₃₄F₂N₆O₆Ni: C 56.77, H 4.73, N 11.69%, O 13.36; Found: C 56.73, H 4.78, N 11.64%, O 13.40.