Ethyl 7-chloro-1-cyclo­propyl-6-fluoro-8-nitro-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ate

Raed A Al-Qawasmeh

doi:10.1107/S1600536812011373

. 2012 Jul 25;68(Pt 8):o2533. doi: 10.1107/S1600536812011373

Ethyl 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Raed A Al-Qawasmeh ^a,^*

PMCID: PMC3414979 PMID: 22904966

Abstract

In the title compound, C₁₅H₁₂ClFN₂O₅, molecules are packed in the crystal lattice in a parallel fashion sustained by various C—H⋯O [C⋯O = 3.065 (5)–3.537 (5) Å] and C—H⋯Cl [3.431 (5)–3.735 (4) Å] interactions.

Related literature

For the biological activities of fluoroquinolone derivatives, see: Li et al. (2000 ▶); Mitscher (2005 ▶). For the synthesis of the title compound, see: Al-Qawasmeh et al. (2009 ▶); Al-Hiari et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₂ClFN₂O₅
M _r = 354.72
Triclinic,
a = 8.2339 (16) Å
b = 9.1523 (18) Å
c = 10.736 (2) Å
α = 85.60 (3)°
β = 81.20 (3)°
γ = 74.13 (3)°
V = 768.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 291 K
0.96 × 0.35 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.857, T _max = 1.000
4468 measured reflections
2713 independent reflections
1617 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.195
S = 1.05
2713 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011373/ds2180sup1.cif

e-68-o2533-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011373/ds2180Isup2.hkl

e-68-o2533-Isup2.hkl^{(133.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812011373/ds2180Isup3.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
C14—H14A⋯O1ⁱ	0.97	2.54	3.489 (4)	167
C14—H14B⋯O1ⁱⁱ	0.97	2.51	3.471 (5)	172
C15—H15A⋯O2ⁱⁱⁱ	0.98	2.58	3.537 (5)	165
C4—H4A⋯O2^iv	0.93	2.71	3.065 (5)	104
C13—H13A⋯O4ⁱⁱ	0.97	2.71	3.439 (5)	132
C11—H11A⋯Cl1^v	0.97	2.91	3.431 (5)	115
C13—H13A⋯Cl1^vi	0.97	2.89	3.735 (4)	146

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

Acknowledgments

The author gratefully acknowledges financial support from the Deanship of Scientific Research at the University of Jordan (grant No. 7/1005/2006). Dr Murad AlDamen is acknowledged for collecting the data.

supplementary crystallographic information

Comment

Fluoroquinolone derivatives have been widely investigated as drugs against bacterial infections. Ciprofloxacine, one derivative of fluoroquinolone, represents one of the most effective antiinfectious drugs currently in clinical use (Li et al., 2000; Mitscher 2005). In the present paper, we describe the title compound, I, which has been synthesized from 2,4,-di chloro-5-fluoro-3-nitrobenzoic acid according to the published literature (Al-Hiari et al., 2006) and (Al-Qawasmeh et al., 2009). The title compound is an important synthetic intermediate for the synthesis of the analogues of the antimicrobial drug ciprofloxcaine. The title molecule crystallizes in the centrosymmetric triclinic space group P-1. In the crystal structure of (I), the molecules are held together by C—H···O [3.065 (5)-3.537 (5) Å] and C—H···Cl [3.431 (5)-3.735 (4) Å] (Table 1).

Experimental

The title compound was synthesized according to the published literature (Al-Hiari et al., 2006) and it has been recrystallized from hot ethanol to produce a yellow crystalline material