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

Sun, H.; Jiang, L.; Li, Y.-L.; Lu, X.; Xu, H.

doi:10.1107/S160053681104205X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2974

doi:10.1107/S160053681104205X

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

Hong-shun Sun,^a ^* Long Jiang,^b Yu-Long Li,^c Xin-hua Lu ^a and Hong Xu ^c

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, ^bR&D Center, Jiangsu Yabang Pharmaceutical Group, Liangchang Road East No. 6 Jingtan, Changzhou 213200, People's Republic of China, and ^cDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: njutshs@126.com

(Received 26 September 2011; accepted 12 October 2011; online 22 October 2011)

In the molecule of the title compound, C₁₅H₁₂ClF₂NO₃, the quinoline ring system is not planar, the dihedral angle between the pyridine and benzene rings being 3.55 (8)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into layers parallel to (101).

Related literature

For the antibacterial activity of quinolone derivatives, see: Fujita & Chiba (1998 ). For a related structure, see: Wang et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₂ClF₂NO₃
M_r = 327.71
Monoclinic, P 2₁ /n
a = 11.336 (2) Å
b = 7.7440 (15) Å
c = 16.157 (3) Å
β = 95.40 (3)°
V = 1412.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.914, T_max = 0.970
2741 measured reflections
2604 independent reflections
1728 reflections with I > 2σ(I)
R_int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.158
S = 1.00
2604 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1ⁱ	0.97	2.55	3.240 (4)	128
C11—H11B⋯O1ⁱⁱ	0.97	2.54	3.491 (4)	167
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681104205X/rz2646sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681104205X/rz2646Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681104205X/rz2646Isup3.cml

checkCIF report

Comment top

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

The quinoline ring system is not planar, the dihedral angle between the pyridine and benzene rings being 3.55 (8)°. The dihedral angle between the three-membered ring and the quinoline ring system is 80.5 (5)°. Bond lengths and angles agree well with those observed in the strictly related compound ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate reported recently (Wang et al., 2008). In the crystal structure, intermolecular C—H···O hydrogen bonds link molecules into layers parallel to the (101) plane.

Related literature top

For the antibacterial activity of quinolone derivatives, see: Fujita & Chiba (1998). For a related structure, see: Wang et al. (2008).

Experimental top

A solution of 3-cyclopropylamino-2-(2,4,5-trifluoro-3-chlorobenzoyl)acrylic acid ethyl ester (26.1 g, 0.075 mol) in DMF (110 ml) was treated with K₂CO₃ (22 g, 0.16 mol) and then heated to 50°C with stirring for 1 h. The resulting precipitate was filtered, washed with a mixture of ice and water, and dried to give 22 g of the title compound (yield 90%). Crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow evaporation of an acetone solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo,1995); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate top

Crystal data top

C₁₅H₁₂ClF₂NO₃	F(000) = 672
M_r = 327.71	D_x = 1.541 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.336 (2) Å	θ = 9–13°
b = 7.7440 (15) Å	µ = 0.31 mm⁻¹
c = 16.157 (3) Å	T = 293 K
β = 95.40 (3)°	Block, colourless
V = 1412.1 (5) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1728 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.4°, θ_min = 2.1°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.914, T_max = 0.970	l = −19→19
2741 measured reflections	3 standard reflections every 200 reflections
2604 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.094P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2604 reflections	Δρ_max = 0.21 e Å⁻³
200 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (3)

Crystal data top

C₁₅H₁₂ClF₂NO₃	V = 1412.1 (5) Å³
M_r = 327.71	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.336 (2) Å	µ = 0.31 mm⁻¹
b = 7.7440 (15) Å	T = 293 K
c = 16.157 (3) Å	0.30 × 0.20 × 0.10 mm
β = 95.40 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1728 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.025
T_min = 0.914, T_max = 0.970	3 standard reflections every 200 reflections
2741 measured reflections	intensity decay: 1%
2604 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2604 reflections	Δρ_min = −0.25 e Å⁻³
200 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl	0.19669 (7)	0.51225 (11)	0.40024 (6)	0.0668 (4)
N	0.44922 (19)	0.3170 (3)	0.40949 (14)	0.0419 (6)
O1	0.59434 (19)	0.1055 (3)	0.62827 (13)	0.0642 (7)
C1	0.3696 (3)	0.2253 (4)	0.62119 (19)	0.0544 (8)
H1A	0.4037	0.1728	0.6694	0.065*
F1	0.19320 (19)	0.2766 (4)	0.68412 (14)	0.0983 (8)
O2	0.79506 (19)	0.0443 (3)	0.54403 (15)	0.0651 (7)
F2	0.09874 (16)	0.4358 (3)	0.54885 (14)	0.0800 (7)
C2	0.2582 (3)	0.2886 (5)	0.6180 (2)	0.0631 (9)
O3	0.79232 (18)	0.1827 (3)	0.42263 (14)	0.0627 (6)
C3	0.2086 (3)	0.3706 (4)	0.5476 (2)	0.0570 (9)
C4	0.2681 (3)	0.3882 (4)	0.47802 (19)	0.0485 (8)
C5	0.3828 (2)	0.3153 (3)	0.47746 (17)	0.0399 (7)
C6	0.4329 (2)	0.2392 (4)	0.55187 (17)	0.0420 (7)
C7	0.5626 (2)	0.2603 (4)	0.41917 (17)	0.0436 (7)
H7A	0.6060	0.2690	0.3733	0.052*
C8	0.6190 (2)	0.1915 (4)	0.48987 (17)	0.0421 (7)
C9	0.5555 (2)	0.1703 (4)	0.56176 (17)	0.0440 (7)
C10	0.4003 (3)	0.3598 (4)	0.32426 (17)	0.0499 (8)
H10A	0.3941	0.4831	0.3109	0.060*
C11	0.3070 (3)	0.2476 (4)	0.28256 (18)	0.0569 (9)
H11A	0.2816	0.1486	0.3131	0.068*
H11B	0.2450	0.3023	0.2462	0.068*
C12	0.4275 (3)	0.2441 (5)	0.25528 (18)	0.0630 (9)
H12A	0.4393	0.2967	0.2022	0.076*
H12B	0.4759	0.1431	0.2692	0.076*
C13	0.7432 (3)	0.1294 (4)	0.49057 (19)	0.0475 (7)
C14	0.9161 (3)	0.1308 (6)	0.4192 (2)	0.0697 (10)
H14A	0.9241	0.0067	0.4261	0.084*
H14B	0.9663	0.1869	0.4632	0.084*
C15	0.9506 (4)	0.1833 (6)	0.3377 (2)	0.0891 (13)
H15A	1.0316	0.1516	0.3332	0.134*
H15B	0.9421	0.3062	0.3317	0.134*
H15C	0.9005	0.1266	0.2947	0.134*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0592 (5)	0.0603 (6)	0.0764 (6)	0.0187 (4)	−0.0166 (4)	−0.0001 (4)
N	0.0404 (13)	0.0399 (13)	0.0437 (13)	−0.0013 (10)	−0.0054 (10)	0.0007 (10)
O1	0.0579 (13)	0.0809 (17)	0.0511 (13)	0.0097 (12)	−0.0089 (10)	0.0147 (12)
C1	0.056 (2)	0.058 (2)	0.0477 (17)	−0.0018 (16)	0.0012 (15)	0.0002 (15)
F1	0.0732 (15)	0.146 (2)	0.0798 (14)	0.0125 (15)	0.0296 (12)	0.0032 (15)
O2	0.0507 (13)	0.0699 (16)	0.0727 (15)	0.0149 (11)	−0.0035 (12)	0.0137 (13)
F2	0.0461 (11)	0.0932 (16)	0.1010 (16)	0.0177 (11)	0.0077 (11)	−0.0139 (13)
C2	0.055 (2)	0.078 (2)	0.058 (2)	−0.0008 (18)	0.0145 (17)	−0.0068 (18)
O3	0.0421 (12)	0.0806 (17)	0.0646 (14)	0.0079 (11)	0.0012 (10)	0.0107 (13)
C3	0.0412 (17)	0.060 (2)	0.069 (2)	0.0050 (15)	0.0009 (16)	−0.0149 (18)
C4	0.0454 (17)	0.0388 (16)	0.0585 (19)	0.0015 (13)	−0.0102 (15)	−0.0070 (14)
C5	0.0364 (14)	0.0321 (14)	0.0493 (16)	−0.0045 (12)	−0.0057 (12)	−0.0023 (12)
C6	0.0423 (16)	0.0381 (15)	0.0440 (15)	−0.0032 (12)	−0.0039 (13)	−0.0028 (13)
C7	0.0408 (16)	0.0427 (16)	0.0470 (16)	−0.0042 (13)	0.0024 (13)	−0.0002 (14)
C8	0.0396 (15)	0.0378 (15)	0.0471 (16)	−0.0035 (12)	−0.0043 (13)	−0.0024 (13)
C9	0.0445 (16)	0.0395 (16)	0.0452 (17)	−0.0026 (13)	−0.0110 (13)	−0.0020 (14)
C10	0.0549 (18)	0.0459 (17)	0.0460 (17)	0.0000 (14)	−0.0102 (14)	0.0065 (14)
C11	0.055 (2)	0.061 (2)	0.0516 (17)	0.0007 (16)	−0.0129 (15)	0.0014 (16)
C12	0.069 (2)	0.076 (2)	0.0430 (17)	0.0012 (19)	0.0009 (16)	0.0032 (17)
C13	0.0442 (16)	0.0441 (17)	0.0526 (18)	−0.0020 (14)	−0.0044 (14)	−0.0023 (15)
C14	0.0433 (18)	0.087 (3)	0.079 (2)	0.0094 (18)	0.0044 (17)	0.005 (2)
C15	0.072 (3)	0.106 (3)	0.092 (3)	0.008 (2)	0.022 (2)	0.004 (3)

Geometric parameters (Å, º) top

Cl—C4	1.723 (3)	C7—C8	1.364 (4)
N—C7	1.353 (3)	C7—H7A	0.9300
N—C5	1.389 (4)	C8—C9	1.432 (4)
N—C10	1.473 (3)	C8—C13	1.486 (4)
O1—C9	1.229 (3)	C10—C11	1.481 (4)
C1—C2	1.351 (5)	C10—C12	1.485 (4)
C1—C6	1.390 (4)	C10—H10A	0.9800
C1—H1A	0.9300	C11—C12	1.475 (5)
F1—C2	1.357 (4)	C11—H11A	0.9700
O2—C13	1.196 (3)	C11—H11B	0.9700
F2—C3	1.346 (4)	C12—H12A	0.9700
C2—C3	1.375 (5)	C12—H12B	0.9700
O3—C13	1.342 (4)	C14—C15	1.467 (5)
O3—C14	1.466 (4)	C14—H14A	0.9700
C3—C4	1.371 (4)	C14—H14B	0.9700
C4—C5	1.418 (4)	C15—H15A	0.9600
C5—C6	1.410 (4)	C15—H15B	0.9600
C6—C9	1.483 (4)	C15—H15C	0.9600

C7—N—C5	119.0 (2)	N—C10—C12	118.7 (3)
C7—N—C10	116.8 (2)	C11—C10—C12	59.6 (2)
C5—N—C10	123.8 (2)	N—C10—H10A	116.0
C2—C1—C6	119.5 (3)	C11—C10—H10A	116.0
C2—C1—H1A	120.3	C12—C10—H10A	116.0
C6—C1—H1A	120.3	C12—C11—C10	60.3 (2)
C1—C2—F1	121.3 (3)	C12—C11—H11A	117.7
C1—C2—C3	120.5 (3)	C10—C11—H11A	117.7
F1—C2—C3	118.2 (3)	C12—C11—H11B	117.7
C13—O3—C14	114.8 (2)	C10—C11—H11B	117.7
F2—C3—C4	120.2 (3)	H11A—C11—H11B	114.9
F2—C3—C2	117.9 (3)	C11—C12—C10	60.1 (2)
C4—C3—C2	121.9 (3)	C11—C12—H12A	117.8
C3—C4—C5	119.2 (3)	C10—C12—H12A	117.8
C3—C4—Cl	114.8 (2)	C11—C12—H12B	117.8
C5—C4—Cl	125.9 (3)	C10—C12—H12B	117.8
N—C5—C6	118.3 (2)	H12A—C12—H12B	114.9
N—C5—C4	124.5 (3)	O2—C13—O3	123.1 (3)
C6—C5—C4	117.2 (3)	O2—C13—C8	125.8 (3)
C1—C6—C5	121.5 (3)	O3—C13—C8	111.1 (3)
C1—C6—C9	115.8 (3)	O3—C14—C15	107.1 (3)
C5—C6—C9	122.7 (3)	O3—C14—H14A	110.3
N—C7—C8	126.1 (3)	C15—C14—H14A	110.3
N—C7—H7A	116.9	O3—C14—H14B	110.3
C8—C7—H7A	116.9	C15—C14—H14B	110.3
C7—C8—C9	119.4 (3)	H14A—C14—H14B	108.5
C7—C8—C13	120.1 (3)	C14—C15—H15A	109.5
C9—C8—C13	120.3 (3)	C14—C15—H15B	109.5
O1—C9—C8	126.1 (3)	H15A—C15—H15B	109.5
O1—C9—C6	119.7 (3)	C14—C15—H15C	109.5
C8—C9—C6	114.2 (2)	H15A—C15—H15C	109.5
N—C10—C11	118.9 (3)	H15B—C15—H15C	109.5

C6—C1—C2—F1	179.6 (3)	C10—N—C7—C8	−170.2 (3)
C6—C1—C2—C3	−1.8 (5)	N—C7—C8—C9	1.7 (4)
C1—C2—C3—F2	−178.0 (3)	N—C7—C8—C13	178.1 (3)
F1—C2—C3—F2	0.7 (5)	C7—C8—C9—O1	177.6 (3)
C1—C2—C3—C4	1.4 (5)	C13—C8—C9—O1	1.3 (5)
F1—C2—C3—C4	−179.9 (3)	C7—C8—C9—C6	−3.9 (4)
F2—C3—C4—C5	−178.7 (3)	C13—C8—C9—C6	179.8 (2)
C2—C3—C4—C5	2.0 (5)	C1—C6—C9—O1	0.3 (4)
F2—C3—C4—Cl	5.2 (4)	C5—C6—C9—O1	179.9 (3)
C2—C3—C4—Cl	−174.1 (3)	C1—C6—C9—C8	−178.3 (2)
C7—N—C5—C6	−5.9 (4)	C5—C6—C9—C8	1.3 (4)
C10—N—C5—C6	167.3 (2)	C7—N—C10—C11	110.6 (3)
C7—N—C5—C4	172.8 (3)	C5—N—C10—C11	−62.8 (4)
C10—N—C5—C4	−13.9 (4)	C7—N—C10—C12	41.4 (4)
C3—C4—C5—N	176.6 (3)	C5—N—C10—C12	−132.0 (3)
Cl—C4—C5—N	−7.8 (4)	N—C10—C11—C12	−108.2 (3)
C3—C4—C5—C6	−4.7 (4)	N—C10—C12—C11	108.5 (3)
Cl—C4—C5—C6	170.9 (2)	C14—O3—C13—O2	−0.9 (5)
C2—C1—C6—C5	−1.1 (5)	C14—O3—C13—C8	178.5 (3)
C2—C1—C6—C9	178.4 (3)	C7—C8—C13—O2	−168.0 (3)
N—C5—C6—C1	−176.8 (3)	C9—C8—C13—O2	8.3 (5)
C4—C5—C6—C1	4.3 (4)	C7—C8—C13—O3	12.5 (4)
N—C5—C6—C9	3.6 (4)	C9—C8—C13—O3	−171.2 (2)
C4—C5—C6—C9	−175.2 (3)	C13—O3—C14—C15	174.0 (3)
C5—N—C7—C8	3.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.97	2.55	3.240 (4)	128
C11—H11B···O1ⁱⁱ	0.97	2.54	3.491 (4)	167

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂ClF₂NO₃
M_r	327.71
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.336 (2), 7.7440 (15), 16.157 (3)
β (°)	95.40 (3)
V (Å³)	1412.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.914, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	2741, 2604, 1728
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.158, 1.00
No. of reflections	2604
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.9700	2.5500	3.240 (4)	128.00
C11—H11B···O1ⁱⁱ	0.9700	2.5400	3.491 (4)	167.00

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fujita, M. & Chiba, K. (1998). Chem. Pharm. Bull. 46, 631–638. Web of Science CrossRef CAS PubMed Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, D.-C., Huang, X.-M., Liu, Y.-P. & Tang, C.-L. (2008). Acta Cryst. E64, o2214. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o2974

doi:10.1107/S160053681104205X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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