Ethyl 7-amino-1-cyclo­propyl-6-fluoro-8-meth­oxy-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ate monohydrate

Jia Pan; Li Yang; Zhi-Hua Mao; Ling-Ling Weng

doi:10.1107/S1600536808002547

. 2008 Jan 30;64(Pt 2):o527. doi: 10.1107/S1600536808002547

Ethyl 7-amino-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate monohydrate

Jia Pan ^a, Li Yang ^a, Zhi-Hua Mao ^b, Ling-Ling Weng ^a,^*

PMCID: PMC2960450 PMID: 21201546

Abstract

In the title compound, C₁₆H₁₇FN₂O₄·H₂O, the dihedral angle between the heterocyclic ring and the benzene ring is 5.77 (9)°, that between the heterocycle and the ethoxycarbonyl plane is 15.5 (1)°, and that between the heterocyclic ring and the cyclopropane ring is 67.75 (13)°. In the crystal structure, molecules are linked into a ribbon-like structure along the c axis by N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For general background, see: Fujita & Chiba (1998 ▶).

Experimental

Crystal data

C₁₆H₁₇FN₂O₄·H₂O
M _r = 338.33
Monoclinic,
a = 10.096 (4) Å
b = 14.699 (5) Å
c = 11.028 (6) Å
β = 94.26 (4)°
V = 1632.0 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 291 (2) K
0.45 × 0.42 × 0.39 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3157 measured reflections
3009 independent reflections
1741 reflections with I > 2σ(I)
R _int = 0.007
3 standard reflections every 300 reflections intensity decay: 0.8%

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.125
S = 1.04
3009 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002547/ci2556sup1.cif

e-64-0o527-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002547/ci2556Isup2.hkl

e-64-0o527-Isup2.hkl^{(147.7KB, 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
N1—H1N1⋯O1Wⁱ	0.91 (3)	2.15 (3)	2.930 (3)	143 (2)
N1—H2N1⋯O4ⁱⁱ	0.85 (3)	2.33 (3)	3.061 (3)	144 (2)
O1W—H1W⋯O2ⁱⁱⁱ	0.84 (3)	2.13 (3)	2.916 (3)	155 (3)
O1W—H2W⋯O2	0.91 (3)	1.96 (3)	2.864 (3)	171 (3)

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

supplementary crystallographic information

Comment

Quinolone antibacterials were found several decades ago, and some excellent antibacterials have been developed and used widely now (Fujita & Chiba, 1998). An interest in search of more potent antibacterial agents led us to design and synthesis a new type of quinoline derivatives. The title compound is one of the key intermediates and we report here its crystal structure.

The pyridinone ring is planar to within ±0.057 (2) Å (Fig. 1). The dihedral angle between the pyridine and benzene rings is 5.77 (9)°, and that between the pyridine and carboxylate plane is 15.5 (1)°. In the crystal structure, the molecules are linked into a ribbon like structure along the c axis (Fig. 2) by N—H···O and O—H···O hydrogen bonds (Table 1).

Experimental

Ethyl 7-azido-1-cyclopropyl-6-fluoro-8-methoxyl-4-oxo-1,4-dihydroquinoline-3- carboxylate (2 g, 5.8 mmol), 5% Pd/C (0.4 g) were suspended in methanol (20 ml) and the mixture was hydrogenated at 303 K for 6 h. The reaction mixture was then filtered and concentrated under vacuum. The residue obtained was purified by silica gel chromatography. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a acetyl acetate-chloroform (1.2:1 v/v) solution at room temperature.