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

Pan, J.; Yang, L.; Mao, Z.-H.; Weng, L.-L.

doi:10.1107/S1600536808002547

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o527

doi:10.1107/S1600536808002547

Open

access

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 and Ling-Ling Weng ^a ^*

^aDepartment of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China, and ^bThe Center for Testing and Analysis, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: lingling.weng@yahoo.com.cn

(Received 17 January 2008; accepted 23 January 2008; online 30 January 2008)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.043
wR(F²) = 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

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

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids drawn at the 30% probability level. The dashed line indicates a hydrogen bond.
	Fig. 2. Crystal packing of the title compound, viwed down the a axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₆H₁₇FN₂O₄·H₂O	F(000) = 712
M_r = 338.33	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24 reflections
a = 10.096 (4) Å	θ = 4.5–7.4°
b = 14.699 (5) Å	µ = 0.11 mm⁻¹
c = 11.028 (6) Å	T = 291 K
β = 94.26 (4)°	Block, yellow
V = 1632.0 (12) Å³	0.45 × 0.42 × 0.39 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.007
Radiation source: fine-focus sealed tube	θ_max = 25.4°, θ_min = 2.3°
Graphite monochromator	h = −12→12
ω/2θ scans	k = 0→17
3157 measured reflections	l = −4→13
3009 independent reflections	3 standard reflections every 300 reflections
1741 reflections with I > 2σ(I)	intensity decay: 0.8%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: mixed
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0627P)² + 0.1314P] where P = (F_o² + 2F_c²)/3
3009 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₆H₁₇FN₂O₄·H₂O	V = 1632.0 (12) Å³
M_r = 338.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.096 (4) Å	µ = 0.11 mm⁻¹
b = 14.699 (5) Å	T = 291 K
c = 11.028 (6) Å	0.45 × 0.42 × 0.39 mm
β = 94.26 (4)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.007
3157 measured reflections	3 standard reflections every 300 reflections
3009 independent reflections	intensity decay: 0.8%
1741 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
3009 reflections	Δρ_min = −0.19 e Å⁻³
235 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
F1	0.51891 (13)	0.59935 (11)	1.01305 (12)	0.0667 (4)
O1	0.07128 (14)	0.68291 (10)	1.03507 (12)	0.0451 (4)
O2	0.33328 (14)	0.56826 (12)	0.58213 (13)	0.0519 (4)
O3	−0.04405 (16)	0.62649 (11)	0.41364 (13)	0.0552 (5)
O4	0.16963 (18)	0.62837 (18)	0.37733 (15)	0.1007 (9)
N1	0.3174 (3)	0.65375 (16)	1.14712 (18)	0.0514 (5)
H1N1	0.385 (3)	0.6210 (17)	1.184 (2)	0.068 (9)*
H2N1	0.248 (3)	0.6504 (18)	1.186 (2)	0.071 (9)*
N2	0.01966 (16)	0.64366 (12)	0.77689 (13)	0.0374 (4)
C1	0.3794 (2)	0.59542 (15)	0.83243 (19)	0.0436 (5)
H1	0.4507	0.5774	0.7894	0.052*
C2	0.3970 (2)	0.61005 (15)	0.95442 (19)	0.0433 (5)
C3	0.2938 (2)	0.63708 (14)	1.02489 (17)	0.0397 (5)
C4	0.1693 (2)	0.65127 (13)	0.96495 (17)	0.0352 (5)
C5	0.1457 (2)	0.63418 (13)	0.83915 (17)	0.0333 (5)
C6	0.2533 (2)	0.60753 (13)	0.77155 (17)	0.0358 (5)
C7	0.0710 (3)	0.78037 (18)	1.0445 (3)	0.0786 (9)
H7A	0.1564	0.8008	1.0778	0.118*
H7B	0.0041	0.7990	1.0968	0.118*
H7C	0.0523	0.8064	0.9653	0.118*
C8	0.2389 (2)	0.59719 (14)	0.63888 (17)	0.0378 (5)
C9	0.1107 (2)	0.62227 (14)	0.58234 (17)	0.0401 (5)
C10	0.0092 (2)	0.64129 (14)	0.65419 (17)	0.0397 (5)
H10	−0.0738	0.6536	0.6152	0.048*
C11	−0.1031 (2)	0.65083 (17)	0.83913 (18)	0.0449 (6)
H11	−0.1233	0.7109	0.8716	0.054*
C12	−0.2192 (2)	0.5947 (2)	0.7935 (2)	0.0723 (9)
H12A	−0.2086	0.5554	0.7242	0.087*
H12B	−0.3070	0.6208	0.7971	0.087*
C13	−0.1436 (2)	0.5712 (2)	0.9108 (2)	0.0627 (7)
H13A	−0.1857	0.5830	0.9854	0.075*
H13B	−0.0873	0.5177	0.9126	0.075*
C14	0.0853 (2)	0.62535 (17)	0.44863 (19)	0.0508 (6)
C15	−0.0802 (3)	0.6314 (2)	0.28436 (19)	0.0693 (8)
H15A	−0.0528	0.5763	0.2449	0.083*
H15B	−0.0360	0.6826	0.2493	0.083*
C16	−0.2257 (2)	0.64228 (17)	0.2653 (2)	0.0589 (7)
H16A	−0.2687	0.5904	0.2979	0.088*
H16B	−0.2506	0.6471	0.1798	0.088*
H16C	−0.2523	0.6964	0.3058	0.088*
O1W	0.5509 (2)	0.44950 (16)	0.65115 (16)	0.0715 (6)
H1W	0.606 (3)	0.446 (2)	0.598 (3)	0.091 (11)*
H2W	0.486 (3)	0.488 (2)	0.621 (3)	0.097 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0396 (8)	0.1032 (12)	0.0559 (8)	0.0081 (7)	−0.0058 (6)	−0.0147 (8)
O1	0.0457 (9)	0.0567 (10)	0.0346 (7)	0.0092 (8)	0.0143 (6)	−0.0021 (7)
O2	0.0422 (9)	0.0766 (11)	0.0388 (8)	0.0138 (8)	0.0163 (7)	−0.0026 (7)
O3	0.0469 (10)	0.0891 (13)	0.0303 (8)	0.0030 (9)	0.0083 (7)	0.0013 (7)
O4	0.0523 (12)	0.215 (3)	0.0373 (10)	0.0254 (13)	0.0193 (9)	0.0150 (12)
N1	0.0482 (13)	0.0683 (15)	0.0378 (11)	0.0021 (11)	0.0036 (10)	−0.0036 (10)
N2	0.0332 (10)	0.0504 (11)	0.0298 (9)	0.0072 (8)	0.0109 (7)	0.0037 (7)
C1	0.0340 (12)	0.0527 (14)	0.0451 (13)	0.0016 (10)	0.0109 (10)	−0.0051 (10)
C2	0.0337 (12)	0.0528 (14)	0.0428 (12)	0.0019 (10)	−0.0008 (10)	−0.0034 (10)
C3	0.0449 (13)	0.0402 (12)	0.0344 (11)	−0.0043 (10)	0.0063 (9)	0.0002 (9)
C4	0.0364 (12)	0.0368 (11)	0.0340 (10)	0.0013 (9)	0.0121 (9)	0.0001 (9)
C5	0.0331 (11)	0.0336 (11)	0.0341 (10)	0.0011 (9)	0.0075 (8)	0.0031 (8)
C6	0.0337 (12)	0.0373 (12)	0.0373 (11)	−0.0026 (9)	0.0085 (9)	−0.0001 (8)
C7	0.097 (2)	0.0622 (18)	0.0805 (19)	0.0211 (17)	0.0311 (17)	−0.0148 (15)
C8	0.0384 (12)	0.0414 (12)	0.0355 (11)	−0.0007 (10)	0.0145 (9)	−0.0008 (9)
C9	0.0378 (12)	0.0518 (14)	0.0315 (11)	0.0038 (10)	0.0093 (9)	0.0018 (9)
C10	0.0350 (12)	0.0519 (14)	0.0327 (10)	0.0079 (10)	0.0069 (9)	0.0078 (9)
C11	0.0320 (12)	0.0659 (15)	0.0385 (11)	0.0082 (11)	0.0129 (9)	0.0041 (10)
C12	0.0403 (15)	0.130 (3)	0.0480 (14)	−0.0086 (15)	0.0124 (12)	0.0057 (15)
C13	0.0492 (15)	0.094 (2)	0.0469 (13)	−0.0127 (14)	0.0168 (11)	0.0119 (13)
C14	0.0444 (14)	0.0763 (17)	0.0331 (11)	0.0094 (12)	0.0123 (10)	0.0023 (11)
C15	0.0627 (18)	0.114 (2)	0.0311 (12)	0.0122 (16)	0.0048 (12)	−0.0030 (13)
C16	0.0602 (17)	0.0649 (17)	0.0508 (14)	0.0107 (13)	−0.0012 (12)	−0.0041 (12)
O1W	0.0600 (13)	0.1157 (18)	0.0396 (9)	0.0301 (12)	0.0077 (9)	−0.0035 (10)

Geometric parameters (Å, º) top

F1—C2	1.356 (2)	C7—H7B	0.96
O1—C4	1.381 (2)	C7—H7C	0.96
O1—C7	1.436 (3)	C8—C9	1.442 (3)
O2—C8	1.252 (2)	C9—C10	1.371 (3)
O3—C14	1.334 (3)	C9—C14	1.479 (3)
O3—C15	1.447 (3)	C10—H10	0.93
O4—C14	1.202 (3)	C11—C13	1.486 (3)
N1—C3	1.373 (3)	C11—C12	1.490 (3)
N1—H1N1	0.91 (3)	C11—H11	0.98
N1—H2N1	0.85 (3)	C12—C13	1.492 (4)
N2—C10	1.350 (2)	C12—H12A	0.97
N2—C5	1.408 (3)	C12—H12B	0.97
N2—C11	1.465 (3)	C13—H13A	0.97
C1—C2	1.361 (3)	C13—H13B	0.97
C1—C6	1.405 (3)	C15—C16	1.477 (3)
C1—H1	0.9300	C15—H15A	0.97
C2—C3	1.403 (3)	C15—H15B	0.97
C3—C4	1.391 (3)	C16—H16A	0.96
C4—C5	1.413 (3)	C16—H16B	0.96
C5—C6	1.418 (3)	C16—H16C	0.96
C6—C8	1.467 (3)	O1W—H1W	0.84 (3)
C7—H7A	0.96	O1W—H2W	0.91 (3)

C4—O1—C7	112.45 (17)	N2—C10—C9	125.34 (19)
C14—O3—C15	117.11 (18)	N2—C10—H10	117.3
C3—N1—H1N1	114.2 (16)	C9—C10—H10	117.3
C3—N1—H2N1	113.3 (18)	N2—C11—C13	117.9 (2)
H1N1—N1—H2N1	112 (2)	N2—C11—C12	118.3 (2)
C10—N2—C5	119.16 (17)	C13—C11—C12	60.20 (17)
C10—N2—C11	117.75 (17)	N2—C11—H11	116.3
C5—N2—C11	123.00 (15)	C13—C11—H11	116.3
C2—C1—C6	119.99 (19)	C12—C11—H11	116.3
C2—C1—H1	120.0	C11—C12—C13	59.79 (16)
C6—C1—H1	120.0	C11—C12—H12A	117.8
F1—C2—C1	120.05 (19)	C13—C12—H12A	117.8
F1—C2—C3	117.01 (18)	C11—C12—H12B	117.8
C1—C2—C3	122.9 (2)	C13—C12—H12B	117.8
N1—C3—C4	121.6 (2)	H12A—C12—H12B	114.9
N1—C3—C2	120.8 (2)	C11—C13—C12	60.01 (16)
C4—C3—C2	117.47 (18)	C11—C13—H13A	117.8
O1—C4—C3	116.36 (17)	C12—C13—H13A	117.8
O1—C4—C5	122.29 (18)	C11—C13—H13B	117.8
C3—C4—C5	121.36 (18)	C12—C13—H13B	117.8
N2—C5—C4	122.81 (18)	H13A—C13—H13B	114.9
N2—C5—C6	118.12 (17)	O4—C14—O3	122.4 (2)
C4—C5—C6	119.06 (18)	O4—C14—C9	125.0 (2)
C1—C6—C5	119.07 (18)	O3—C14—C9	112.52 (18)
C1—C6—C8	118.85 (18)	O3—C15—C16	108.7 (2)
C5—C6—C8	121.99 (18)	O3—C15—H15A	109.9
O1—C7—H7A	109.5	C16—C15—H15A	109.9
O1—C7—H7B	109.5	O3—C15—H15B	109.9
H7A—C7—H7B	109.5	C16—C15—H15B	109.9
O1—C7—H7C	109.5	H15A—C15—H15B	108.3
H7A—C7—H7C	109.5	C15—C16—H16A	109.5
H7B—C7—H7C	109.5	C15—C16—H16B	109.5
O2—C8—C9	124.20 (18)	H16A—C16—H16B	109.5
O2—C8—C6	120.70 (19)	C15—C16—H16C	109.5
C9—C8—C6	115.09 (17)	H16A—C16—H16C	109.5
C10—C9—C8	119.22 (18)	H16B—C16—H16C	109.5
C10—C9—C14	119.2 (2)	H1W—O1W—H2W	107 (3)
C8—C9—C14	121.54 (18)

Hydrogen-bond geometry (Å, º) top

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)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇FN₂O₄·H₂O
M_r	338.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	10.096 (4), 14.699 (5), 11.028 (6)
β (°)	94.26 (4)
V (Å³)	1632.0 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.42 × 0.39

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3157, 3009, 1741
R_int	0.007
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 1.04
No. of reflections	3009
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

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)

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

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fujita, M. & Chiba, K. (1998). Chem. Pharm. Bull. 46, 631–638. Web of Science CrossRef CAS PubMed Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Pittsburgh Meeting Abstract PA 104. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o527

doi:10.1107/S1600536808002547

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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