Poly[[[(1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro­quinoline-3-carboxyl­ato)manganese(II)]-μ3-4,4′-oxydibenzoato] monohydrate]

Jun Hong

doi:10.1107/S1600536807060825

. 2007 Dec 6;64(Pt 1):m21. doi: 10.1107/S1600536807060825

Poly[[[(1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato)manganese(II)]-μ₃-4,4′-oxydibenzoato] monohydrate]

Jun Hong ^a,^*

PMCID: PMC2914913 PMID: 21200557

Abstract

In the title compound, {[Mn(C₁₆H₁₈N₃O₃)(C₁₄H₈O₅)]·H₂O}_n, the unique Mn^II ion is coordinated by two O atoms from a chelating 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate ligand and three O atoms from three 4,4′-oxydibenzoate ligands, forming a distorted square-pyramidal coordination environment. In the crystal structure, centrosymmetric dinuclear manganese units are linked via 4,4′-oxydibenzoate ligands into one-dimensional chains; these chains are, in turn, connected via intermolecular N—H⋯O and O—H⋯O hydrogen bonds to form a two-dimensional supramolecular network. The O atom of the solvent water molecule is disordered over two sites with equal occupancies; the attached H atoms are common to both sites.

Related literature

For general background, see: Xiao et al. (2005 ▶). For a related structure, see: An et al. (2007 ▶).

Experimental

Crystal data

[Mn(C₁₆H₁₈N₃O₃)(C₁₄H₈O₅)]·H₂O
M _r = 648.49
Triclinic,
a = 10.208 (5) Å
b = 11.915 (5) Å
c = 13.202 (5) Å
α = 100.751 (5)°
β = 112.010 (5)°
γ = 102.318 (5)°
V = 1390.1 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.885, T _max = 0.908
13533 measured reflections
6236 independent reflections
5434 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.129
S = 1.05
6236 reflections
407 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 1990 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807060825/lh2564sup1.cif

e-64-00m21-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060825/lh2564Isup2.hkl

e-64-00m21-Isup2.hkl^{(305.2KB, 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
O1W′—H2⋯O3ⁱ	1.16	2.40	3.359 (14)	138
O1W′—H2⋯O4ⁱ	1.16	1.87	2.874 (12)	142
N3—H3B⋯O8ⁱ	0.90	1.80	2.694 (3)	169
N3—H3C⋯O4ⁱⁱ	0.90	1.83	2.716 (3)	169

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

Acknowledgments

The authors thank Jilin Normal University for supporting this work.

supplementary crystallographic information

Comment

Norfloxacin [1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylic acid, Hcf] is a member of a class of quinolones that is used to treat infections (Xiao et al. 2005; An et al. 2007). As a part of our ongoing investigations in this field, we report here the crystal structure of the title compound. In the crystal structure of the title compound, the Mn atoms are coordinated by three oxygen atoms of one Hcf ligand, one 4,4'-oxydibenzoate ligand and one oxygen atom from one symmetry related 4,4'-oxydibenzoate within a distorted square-pyramidal geometry (Figure 1). In the crystal structure, dinuclear manganese units are linked via the 4,4'-oxydibenzoate anions into a one-dimensional chain running along [-2, -3, 2]. Finally, one-dimensional chains are connected with N—H···O and O—H···O hydrogen bonds to form a two-dimensional supramolecular network.

Experimental

The title compound was prepared by a hydrothermal method. A mixture of MnCl₂ (0.07 g 0.5 mmol), norfloxacin (0.16 g 0.5 mmol), 4,4'-oxy-bisbenzoic acid (0.13 g 0.5 mmol) and water (10 ml) was stirred for 20 min and then transferred to a 23 ml Teflon reactor. The reactor was kept at 433 K for 72 h under autogenous pressure. Single crystals of were obtained after cooling to room temperature.