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

Volume 64
Part 2
Page o527
February 2008

Received 17 January 2008
Accepted 23 January 2008
Online 30 January 2008

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.126
Data-to-parameter ratio = 12.8
Details

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

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-HO and O-HO 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
= 94.26 (4)°
V = 1632.0 (12) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.007
3 standard reflections every 300 reflections intensity decay: 0.8%

Refinement

R[F² > 2(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
_max = 0.20 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O1Wⁱ	0.91 (3)	2.15 (3)	2.930 (3)	143 (2)
N1-H2N1O4ⁱⁱ	0.85 (3)	2.33 (3)	3.061 (3)	144 (2)
O1W-H1WO2ⁱⁱⁱ	0.84 (3)	2.13 (3)	2.916 (3)	155 (3)
O1W-H2WO2	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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2556 ).

References

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

organic compounds