4-(3-Carb­oxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-carb­oxy­benzoate–benzene-1,4-dicarb­oxy­lic acid (2/1)

Shi-Wei Yan; Hai-Yan Chen; Guang-Ju Zhang; Qin Liao; Yan-Chen Liang

doi:10.1107/S1600536811009524

. 2011 Mar 19;67(Pt 4):o909. doi: 10.1107/S1600536811009524

4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 4-carboxybenzoate–benzene-1,4-dicarboxylic acid (2/1)

Shi-Wei Yan ^a,^*, Hai-Yan Chen ^a, Guang-Ju Zhang ^a, Qin Liao ^a, Yan-Chen Liang ^a

PMCID: PMC3099834 PMID: 21754183

Abstract

In the title compound, C₁₆H₁₉FN₃O₃ ⁺·C₈H₅O₄ ⁻·0.5C₈H₆O₄, the benzene-1,4-dicarboxylic acid molecule is located on a centre of symmetry. In the crystal, the molecules and ions are connected by intermolecular C—H⋯O and O—H⋯O hydrogen bonds and π–π stacking interactions [with a centroid–centroid distance of 3.402 (2) Å], generating a three-dimensional supramolecular structure.

Related literature

For general background to the use of quinolones in the treatment of infections, see: Barbas et al. (2006 ▶); Basavoju et al.(2006 ▶); Xiao et al. (2005 ▶).

Experimental

Crystal data

C₁₆H₁₉FN₃O₃ ⁺·C₈H₅O₄ ⁻·0.5C₈H₆O₄
M _r = 568.53
Triclinic,
a = 9.8901 (15) Å
b = 10.2420 (16) Å
c = 13.665 (2) Å
α = 89.304 (2)°
β = 74.672 (2)°
γ = 71.677 (2)°
V = 1263.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 K
0.46 × 0.45 × 0.36 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.948, T _max = 0.959
10704 measured reflections
5143 independent reflections
4031 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.137
S = 1.00
5143 reflections
394 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009524/ff2003sup1.cif

e-67-0o909-sup1.cif^{(26.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009524/ff2003Isup2.hkl

e-67-0o909-Isup2.hkl^{(251.8KB, 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
C15—H15B⋯O1ⁱ	0.97	2.38	3.274 (2)	153
O5—H5B⋯O7ⁱⁱ	0.97 (3)	1.70 (3)	2.6648 (15)	169 (2)

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

Acknowledgments

This work was supported by the Science and Technology Foundation of Southwest University (SWUB2007035).

supplementary crystallographic information

Comment

Norfloxacin [1–Ethyl–6–fluoro–1,4–dihydro–4–oxo–7–(piperazin–1–yl)quinoline–3–carbo–xylic acid] is member of a class of quinolones used to treat infections (Xiao et al., 2005; Barbas et al., 2006; Basavoju et al., 2006). In this paper,the structure of the title compound, 1, is described (Fig. 1). In compound 1, benzene-1,4-dicarboxylic acid is located on the centre of symmetry. The molecules and the ions are linked by intermolecular C—H···O and O—H···O hydrogen-bonding interactions (C···O = 3.273 (2) Å, O···O = 2.6648 (18) Å) and π—π stacking between the benzene ring of [H₂norf]⁺ and aromatic ring of 1,4-H₂bdc with the centroid-centroid distance of 3.402 (2) Å, generating a three-dimensional supramolecular structure.

Experimental

A mixture of Mn(CH₃COO)₂.4H₂O (0.061 g, 0.25 mmol), Norfloxacin (0.080 g, 0.25 mmol) and distilled water (10 ml) was stirred for 20 min. in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 393 K for 96 h under autogenous pressure. Upon cooling, yellow block of 1 were obtained from the reaction mixture.