Diaqua­bis(norfloxacinato)manganese(II) 2,2′-bipyridine solvate tetra­hydrate

Yan-Jun Wang; Qiu-Yue Lin; Jie Feng; Na Wang

doi:10.1107/S1600536809022831

. 2009 Jun 20;65(Pt 7):m806. doi: 10.1107/S1600536809022831

Diaquabis(norfloxacinato)manganese(II) 2,2′-bipyridine solvate tetrahydrate

Yan-Jun Wang ^a, Qiu-Yue Lin ^a,^*, Jie Feng ^a, Na Wang ^a

PMCID: PMC2969423 PMID: 21582730

Abstract

In the crystal structure of the title compound {systematic name: diaquabis[1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato]manganese(II) 2,2′-bipyridine solvate tetrahydrate}, [Mn(C₁₆H₁₇FN₃O₃)₂(H₂O)₂]·C₁₀H₈N₂·4H₂O, the pyridone O atom and one carboxylate O atom of the two norfloxacin ligands are bound to the Mn^II ion, which is located on an inversion centre, and occupy equatorial positions, while two aqua O atoms lie in apical positions, resulting in a distorted octahedral geometry. The crystal packing is stabilized by N—H⋯O and O—H⋯O hydrogen-bonding interactions.

Related literature

For background, see: Dukhande et al. (2006 ▶).

Experimental

Crystal data

[Mn(C₁₆H₁₇FN₃O₃)₂(H₂O)₂]·C₁₀H₈N₂·4H₂O
M _r = 955.87
Triclinic,
a = 9.5179 (4) Å
b = 11.4645 (2) Å
c = 11.6617 (2) Å
α = 118.8440 (10)°
β = 93.398 (2)°
γ = 97.258 (2)°
V = 1095.06 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 K
0.38 × 0.18 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.921, T _max = 0.981
13676 measured reflections
3856 independent reflections
3208 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.199
S = 1.07
3856 reflections
310 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.51 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/S1600536809022831/at2812sup1.cif

e-65-0m806-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022831/at2812Isup2.hkl

e-65-0m806-Isup2.hkl^{(189KB, 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—H3A⋯O3ⁱ	0.86	2.23	2.725 (4)	117
N3—H3A⋯O3W	0.86	2.54	2.992 (4)	114
O2W—H2WB⋯O2Wⁱⁱ	0.85	1.97	2.789 (5)	163
O3W—H3WA⋯O3Wⁱⁱⁱ	0.784 (19)	2.03 (2)	2.781 (6)	162 (6)
O3W—H3WB⋯N3	0.754 (19)	2.32 (4)	2.992 (4)	149 (5)
O1W—H1WA⋯N4	0.863 (19)	1.96 (2)	2.813 (4)	168 (5)
O1W—H1WB⋯O2W	0.842 (19)	2.24 (3)	3.050 (4)	162 (5)
O2W—H2WA⋯O1W	0.730 (17)	2.65 (4)	3.050 (4)	117 (4)

Open in a new tab

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

Acknowledgments

The authors thank the Natural Science Foundation of Zhejiang Province, China for financial support (grant No. Y407301).

supplementary crystallographic information

Comment

1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid (norfloxacin), is the third generation quinolone antibacterial drug with broad-spectrum antibacterial activity, especially for gram-negative bacteria. It can interfere with the synthesis of DNA, destroy the fission of cells in order to sterilize by inhibiting DNA gyrase. Manganese is an important trace element needed for normal physiological functions and development. It is also a cofactor or required metal ion for many enzymes, such as superoxide dismutase, glutamine synthetase and arginase (Dukhande et al., 2006). Synthesis, characterization and biological activity studies of the manganese complexes have become one of the most attractive research fields in modern bioinorganic chemistry.

In the title compound, the Mn(II) ion in a inversion centre is coordinated with four oxygen atoms of the norfloxacin ligands in the equatorial positions while two oxygen atoms of the water occupy the axial positions resulting in a distorted octahedral geometry around the central metal atom. The Mn—O bond distances arising from the two carbonyl oxygen atoms O1 are longer, [2.157 (2) Å], than those arising from the carboxylate oxygen atoms O2 [2.132 (2) Å]. The axial average linkages between manganese and oxygen atoms of water are substantially longer [2.212 (3) Å] than the equatorial bond distances. The bond angles O1—Mn1—O1A, O2—Mn1—O2A and O1W—Mn1—O1WA are 180° while the bond angles O2—Mn1—O1 and O2A—Mn1—O1 open up slightly from 82.73 (9)° to 97.27 (9)°, resulting in a slight distortion from the idealized octahedral geometry.

The crystal packing is stabilized by N—H···O and O—H···O hydrogen bonding interactions (Table 1).

Experimental

A mixture of 0.1 mmol norfloxacin, 0.1 mmol MnCl₂4H₂O, 0.1 mmol 2,2'-bipyridine and 10 mL distilled water was sealed in a 25 mL Teflon-lined stainless vessel and heated at 433 K for 3 d, then cooled slowly to room temperature. The solution was filtered and block yellow crystals were obtained.