4-(1-Cyclo­propyl-6-fluoro-4-oxo-1,4-dihydro­quinolin-7-yl)piperazin-1-ium 2,4,5-tricarb­oxy­benzene-1-carboxyl­ate monohydrate

Shi-Wei Yan; Yan-Chen Liang; Qin Liao; Guang-Hua Xin; Zhong-Li Ye

doi:10.1107/S1600536812008392

. 2012 Feb 29;68(Pt 3):o919. doi: 10.1107/S1600536812008392

4-(1-Cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2,4,5-tricarboxybenzene-1-carboxylate monohydrate

Shi-Wei Yan ^a,^*, Yan-Chen Liang ^a, Qin Liao ^a, Guang-Hua Xin ^a, Zhong-Li Ye ^a

PMCID: PMC3297959 PMID: 22412762

Abstract

In the crystal of title compound, C₁₆H₁₉FN₃O⁺·C₁₀H₅O₈ ⁻·H₂O, the water molecule and the ions are connected by intermolecular N—H⋯O and O—H⋯O hydrogen bonds and π–π stacking [centroid–centroid separation = 3.602 (1) Å] between the benzene ring and the pyridine ring, generating a three-dimensional supramolecular structure.

Related literature

For general background on 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

C₁₆H₁₉FN₃O⁺·C₁₀H₅O₈ ⁻·H₂O
M _r = 559.50
Triclinic,
a = 9.5537 (19) Å
b = 11.300 (2) Å
c = 11.686 (2) Å
α = 77.03 (3)°
β = 87.01 (3)°
γ = 88.65 (3)°
V = 1227.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.32 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.953, T _max = 0.962
12113 measured reflections
5561 independent reflections
3880 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.159
S = 0.99
5561 reflections
373 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 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 datablock(s) I, global. DOI: 10.1107/S1600536812008392/ff2056sup1.cif

e-68-0o919-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008392/ff2056Isup2.hkl

e-68-0o919-Isup2.hkl^{(272.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008392/ff2056Isup3.cml

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
O1—H1C⋯O3ⁱ	0.94	1.58	2.5170 (18)	177
O1—H1C⋯O4ⁱ	0.94	2.52	3.078 (2)	118
N1—H1B⋯O3ⁱ	0.93 (3)	2.54 (3)	3.006 (3)	111 (2)
N1—H1B⋯O1Wⁱⁱ	0.93 (3)	2.04 (3)	2.929 (3)	158 (2)
O8—H8A⋯O9ⁱⁱⁱ	1.00	1.52	2.519 (2)	178.2

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

Acknowledgments

This work was financially supported by the Science and Technology Foundation of Southwest University (grant No. SWUB2007035) and the Science and Technology Innovation Foundation for Students of Southwest University.

supplementary crystallographic information

Comment

Ciprofloxacin (cipH,1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic 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, we synthesized the complex of L from cipH ligand, and then obtained the compound 1 by reaction with 1,2,4,5-H₄betc in hydrothermal conditions. Here we report the title compound 1.

As shown in Fig. 1, compound 1 contains one [HL]⁺ cation, one [1,2,4-H₃betc]^- anion and one H₂O molecule in the asymmetric unit. Then the molecules and the ions are further linked by intermolecular N—H···O and O—H···O hydrogen-bonding interactions (Table 1) and π–π stacking (separation 3.602 (1) Å) between the benzene rings and the pyridine rings to form a three-dimensional supramolecular structure.

Experimental

A mixture of Mn(CH₃COO)₂.4H₂O(0.123 g, 0.5 mmol), cipH (0.192 g, 0.5 mmol), 1,2,4,5-H₄betc (0.127, 0.5 mmol) and distilled water (7 ml) was stirred for 20 min in air. The mixture was then transferred to a 17 ml Teflon-lined hydrothermal bomb. The bomb was kept at 423 K for 129 h under autogenous pressure. Upon cooling, colorless block of 1 was obtained from the reaction mixture.