1-Cyclo­propyl-6-fluoro-7-(4-nitro­so­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxylic acid

Li, T.; Tang, L.-R.; Zeng, Q.-L.; Chen, W.-J.; Huang, B.

doi:10.1107/S1600536809029729

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2053

doi:10.1107/S1600536809029729

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1-Cyclopropyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Tao Li,^a Li-Rong Tang,^b Qiao-Ling Zeng,^b Wei-Jin Chen ^a and Biao Huang ^b ^*

^aSchool of Life Sciences, Fujian Agriculture and Forestry University, Fuzhou, Fujian 350002, People's Republic of China, and ^bMaterial Engineering College, Fujian Agriculture and Forestry University, Fuzhou, Fujian 350002, People's Republic of China
^*Correspondence e-mail: ltdl@sina.com

(Received 20 June 2009; accepted 27 July 2009; online 31 July 2009)

The title compound, C₁₇H₁₇FN₄O₄, is a derivative of ciprofloxacin [1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid]. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds together with π–π electron ring interactions [centroid–centroid separations between quinoline rings of 3.5864 (11) and 3.9339 (13) Å]. A strong intramolecular O—H⋯O hydrogen bonds is present as well as an intramolecular C—H⋯F interaction.

Related literature

For the biological activity of ciprofloxacin compounds, see: Neu (1987 ). For related structures, see: Turel et al. (1996 ); Drevenšek et al. (2003 ); Li et al. (2005 ); Lou et al. (2007 ). The nitroso-group geometry is similar to that observed in 1,4-dinitrosopiperazine, see: Sekido et al. (1985 ).

Experimental

Crystal data

C₁₇H₁₇FN₄O₄
M_r = 360.35
Triclinic, $[P \overline 1]$
a = 8.378 (3) Å
b = 9.625 (4) Å
c = 10.328 (4) Å
α = 102.99 (2)°
β = 96.089 (14)°
γ = 97.392 (16)°
V = 797.0 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury CCD/AFC diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ) T_min = 0.976, T_max = 0.977
6267 measured reflections
3631 independent reflections
2568 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.207
S = 1.06
3631 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H18⋯O3	0.84	1.78	2.562 (2)	153
C15—H15A⋯O2ⁱ	0.99	2.50	3.405 (3)	151
C15—H15B⋯O3ⁱⁱ	0.99	2.51	3.385 (3)	147
C16—H16A⋯O1ⁱⁱⁱ	0.99	2.60	3.264 (3)	125
C16—H16B⋯F1	0.99	2.14	2.852 (3)	128
Symmetry codes: (i) x+1, y+1, z+1; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029729/fb2160sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029729/fb2160Isup2.hkl

checkCIF report

Comment top

Ciprofloxacin (1-cyclopropyl-6-fluoro -1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid) is used as an antibacterial agent. Ciprofloxacin is widely used in clinical practice for the treatment of certain diseases caused by some Gram negative and as well as Gram positive microorganisms (Neu, 1987). Recently, several structures containing ciprofloxacin have been reported (Turel et al., 1996; Drevenšek et al., 2003; Lou et al., 2007).

Nitrosation of amines by nitrites takes place in acid medium. The nature of the product depends on the nature of the initial amine. Commonly the secondary alkyl amines yield N-nitrosoamines. In our case, the N-nitrosation of ciprofloxacin occurs by ytterbium nitrate in nitric acid and results in the formation of ON-ciprofloxacin under hydrothermal reaction.

The title compound is composed of an essentially planar quinoline ring system [the mean deviation from best plane is 0.0274 (2) Å] which is substituted with cyclopropyl, fluoro, oxo, carboxyl and nitrosopiperazinium groups (Fig. 1). The bond distances and angles are in agreement with those in 1-cyclopropyl-6-fluoro-7- (4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (Li et al., 2005).

In the title structure, the six-membered piperazinyl ring adopts a chair conformation. The nitroso-group geometry with the NO distance equal to 1.2382 (31) Å and O—N—N bond angle of 115.583 (20)° is similar to that observed in 1,4-dinitrosopiperazine (Sekido et al., 1985).

For the hydrogen bonding, please see Tab. 1 that comprises intramolecular and intermolecular hydrogen bonds in the structure (Fig. 2). As shown in Fig. 3, the crystal packing is stabilized by π-π stacking interactions of the quinoline rings, in which the N1 ring (N1/C4—C6/C7—C13) stacks with the inversion-related N1 rings, with the centroid-centroid separations of 3.5864 (11) and 3.9339 (13) Å.

Related literature top

For the biological activity of ciprofloxacin compounds, see: Neu (1987). For related structures, see: Turel et al. (1996); Drevenšek et al. (2003); Li et al. (2005); Lou et al. (2007). The nitroso-group geometry is similar to that observed in 1,4-dinitrosopiperazine, see: Sekido et al. (1985).

Experimental top

The title compound was hydrothermally synthesized under autogenous pressure. A mixture of C₁₇H₁₈FN₃O₃.HCl (ciprofloxacin hydrochloride) (50 mg, 0.14 mmol), Yb(NO₃)₃ (72 mg, 0.2 mmol), HNO₃ (1 ml of 0.5 M), C₂H₅OH (4 ml) and H₂O (8 ml) was sealed in a stainless reactor with a Teflon liner. The mixture was heated to 393 K for one day. After cooling at a rate of 10 K h^-1 to room temperature, yellow needle crystals (average 4 mm long by 0.6 mm diameter) were separated by filtration, washed with distilled water and finally dried in air. Yield 75%, Anal. calc. for C₁₇H₁₇FN₄O₄: C, 56.66; H, 4.76; N, 15.55%; Found: C, 56.82; H, 4.75; N, 15.63%. IR (KBr pellet): 1719(s), 1627(s), 1489(m), 1454(m), 1334(m), 1339(m), 1257(s), 1152(m), 994(m), 896(m), 798(m), 743(m).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title molecule. The displacement ellipsoids are drawn at the 30% propability level
	Fig. 2. The intramolecular and intermoleclar hydrogen bonds or interactions (the dashed lines) in title compound (see Table 1). Symmetry codes: (A) x+1, y+1, z+1; (B) x+1, y+1, z; (C) x, y+1, z
	Fig. 3. The packing of title molecules, showing the π-π-electron ring interactions. The H atoms have been omitted for clarity

1-Cyclopropyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo- 1,4-dihydroquinoline-3-carboxylic acid top

Crystal data top

C₁₇H₁₇FN₄O₄	Z = 2
M_r = 360.35	F(000) = 376
Triclinic, P1	D_x = 1.502 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.378 (3) Å	Cell parameters from 771 reflections
b = 9.625 (4) Å	θ = 2.0–27.4°
c = 10.328 (4) Å	µ = 0.12 mm⁻¹
α = 102.99 (2)°	T = 293 K
β = 96.089 (14)°	Block, yellow
γ = 97.392 (16)°	0.2 × 0.2 × 0.2 mm
V = 797.0 (6) Å³

Data collection top

Rigaku Mercury CCD/AFC diffractometer	3631 independent reflections
Radiation source: fine-focus sealed tube	2568 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.4°, θ_min = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	h = −10→10
T_min = 0.976, T_max = 0.977	k = −12→12
6267 measured reflections	l = −13→11

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)] = 0.067	Hydrogen site location: difference Fourier map
wR(F²) = 0.207	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1165P)² + 0.047P] where P = (F_o² + 2F_c²)/3
3631 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³
67 constraints

Crystal data top

C₁₇H₁₇FN₄O₄	γ = 97.392 (16)°
M_r = 360.35	V = 797.0 (6) Å³
Triclinic, P1	Z = 2
a = 8.378 (3) Å	Mo Kα radiation
b = 9.625 (4) Å	µ = 0.12 mm⁻¹
c = 10.328 (4) Å	T = 293 K
α = 102.99 (2)°	0.2 × 0.2 × 0.2 mm
β = 96.089 (14)°

Data collection top

Rigaku Mercury CCD/AFC diffractometer	3631 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	2568 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.977	R_int = 0.031
6267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.207	H-atom parameters constrained
S = 1.06	Δρ_max = 0.52 e Å⁻³
3631 reflections	Δρ_min = −0.35 e Å⁻³
236 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
N1	0.14474 (19)	0.38921 (17)	0.16119 (15)	0.0330 (4)
O2	−0.1340 (2)	0.09746 (18)	−0.25939 (15)	0.0561 (5)
H18	−0.0827	0.1674	−0.2814	0.084*
O3	0.0676 (2)	0.32428 (17)	−0.25086 (13)	0.0472 (4)
C8	0.2117 (2)	0.4611 (2)	−0.03990 (18)	0.0331 (4)
F1	0.51960 (16)	0.74426 (14)	−0.07933 (12)	0.0505 (4)
C13	0.2335 (2)	0.48548 (19)	0.10118 (18)	0.0318 (4)
C11	0.4372 (2)	0.6987 (2)	0.1245 (2)	0.0342 (4)
C5	0.0120 (2)	0.2477 (2)	−0.05450 (19)	0.0356 (5)
O1	−0.1742 (2)	0.03235 (18)	−0.07173 (17)	0.0580 (5)
C12	0.3415 (2)	0.6063 (2)	0.18211 (19)	0.0344 (4)
H12A	0.3488	0.6247	0.2770	0.041*
C9	0.3081 (3)	0.5551 (2)	−0.0978 (2)	0.0372 (5)
H9A	0.2962	0.5415	−0.1925	0.045*
N2	0.5528 (2)	0.81427 (18)	0.20147 (16)	0.0380 (4)
C7	0.0944 (2)	0.3414 (2)	−0.1242 (2)	0.0361 (5)
C10	0.4184 (3)	0.6654 (2)	−0.0179 (2)	0.0361 (5)
C4	0.0408 (2)	0.2758 (2)	0.0830 (2)	0.0359 (5)
H4A	−0.0163	0.2111	0.1257	0.043*
C6	−0.1066 (3)	0.1168 (2)	−0.1269 (2)	0.0428 (5)
N3	0.7368 (3)	1.0685 (2)	0.37104 (18)	0.0492 (5)
C3	0.1612 (3)	0.4155 (2)	0.30774 (19)	0.0373 (5)
H3A	0.1132	0.4997	0.3544	0.045*
C14	0.5794 (3)	0.8301 (2)	0.3473 (2)	0.0473 (6)
H14A	0.5869	0.7346	0.3663	0.057*
H14B	0.4859	0.8666	0.3870	0.057*
C2	0.3112 (3)	0.3878 (3)	0.3816 (2)	0.0512 (6)
H2A	0.3549	0.4545	0.4696	0.061*
H2B	0.3943	0.3493	0.3283	0.061*
C15	0.7354 (3)	0.9344 (2)	0.4114 (2)	0.0487 (6)
H15A	0.7434	0.9535	0.5103	0.058*
H15B	0.8306	0.8901	0.3840	0.058*
C16	0.5548 (3)	0.9558 (3)	0.1687 (2)	0.0570 (7)
H16A	0.4633	1.0008	0.2039	0.068*
H16B	0.5390	0.9417	0.0700	0.068*
C17	0.7110 (3)	1.0550 (3)	0.2268 (2)	0.0574 (7)
H17A	0.8022	1.0156	0.1856	0.069*
H17B	0.7058	1.1509	0.2082	0.069*
C1	0.1525 (3)	0.2910 (3)	0.3709 (2)	0.0551 (7)
H1A	0.1379	0.1929	0.3111	0.066*
H1B	0.0986	0.2981	0.4524	0.066*
N4	0.7544 (3)	1.1903 (2)	0.4635 (2)	0.0654 (7)
O4	0.7463 (3)	1.3001 (2)	0.4211 (2)	0.0895 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0369 (9)	0.0264 (8)	0.0303 (8)	−0.0042 (6)	−0.0015 (7)	0.0040 (6)
O2	0.0664 (11)	0.0464 (10)	0.0397 (9)	−0.0092 (8)	−0.0087 (8)	−0.0047 (7)
O3	0.0588 (10)	0.0433 (9)	0.0306 (8)	−0.0015 (7)	−0.0052 (7)	0.0012 (6)
C8	0.0372 (10)	0.0277 (9)	0.0302 (10)	0.0036 (8)	−0.0017 (8)	0.0023 (7)
F1	0.0587 (8)	0.0475 (8)	0.0438 (7)	−0.0084 (6)	0.0111 (6)	0.0155 (6)
C13	0.0359 (10)	0.0249 (9)	0.0310 (10)	0.0015 (8)	0.0008 (8)	0.0029 (7)
C11	0.0373 (10)	0.0278 (9)	0.0340 (10)	0.0004 (8)	−0.0015 (8)	0.0061 (8)
C5	0.0382 (10)	0.0268 (10)	0.0348 (11)	0.0003 (8)	−0.0037 (8)	−0.0008 (8)
O1	0.0590 (11)	0.0456 (10)	0.0569 (10)	−0.0192 (8)	−0.0103 (8)	0.0103 (8)
C12	0.0416 (11)	0.0270 (9)	0.0295 (10)	−0.0019 (8)	0.0003 (8)	0.0025 (7)
C9	0.0455 (11)	0.0354 (10)	0.0293 (10)	0.0065 (9)	0.0029 (8)	0.0057 (8)
N2	0.0446 (10)	0.0308 (9)	0.0329 (9)	−0.0071 (7)	−0.0044 (7)	0.0074 (7)
C7	0.0390 (11)	0.0306 (10)	0.0336 (10)	0.0058 (8)	−0.0010 (8)	−0.0002 (8)
C10	0.0395 (10)	0.0312 (10)	0.0375 (11)	0.0008 (8)	0.0039 (8)	0.0115 (8)
C4	0.0361 (10)	0.0284 (10)	0.0380 (11)	−0.0023 (8)	−0.0013 (8)	0.0043 (8)
C6	0.0426 (11)	0.0340 (11)	0.0436 (12)	0.0024 (9)	−0.0064 (9)	0.0002 (9)
N3	0.0662 (13)	0.0354 (10)	0.0359 (9)	−0.0088 (9)	−0.0016 (9)	0.0013 (7)
C3	0.0473 (12)	0.0311 (10)	0.0294 (10)	−0.0022 (8)	0.0031 (8)	0.0045 (8)
C14	0.0608 (14)	0.0394 (12)	0.0337 (11)	−0.0112 (10)	−0.0030 (10)	0.0075 (9)
C2	0.0527 (14)	0.0551 (14)	0.0393 (12)	−0.0017 (11)	−0.0041 (10)	0.0086 (10)
C15	0.0607 (15)	0.0401 (12)	0.0364 (11)	−0.0056 (10)	−0.0068 (10)	0.0051 (9)
C16	0.0679 (16)	0.0395 (13)	0.0546 (14)	−0.0137 (11)	−0.0191 (12)	0.0179 (11)
C17	0.0767 (18)	0.0424 (13)	0.0451 (13)	−0.0128 (12)	−0.0004 (12)	0.0104 (10)
C1	0.0709 (16)	0.0458 (13)	0.0420 (12)	−0.0121 (12)	−0.0059 (11)	0.0150 (10)
N4	0.0859 (17)	0.0430 (12)	0.0536 (13)	−0.0081 (11)	0.0084 (12)	−0.0059 (10)
O4	0.132 (2)	0.0383 (11)	0.0856 (16)	0.0046 (12)	0.0002 (14)	0.0002 (10)

Geometric parameters (Å, º) top

N1—C4	1.346 (2)	C4—H4A	0.9500
N1—C13	1.405 (2)	N3—N4	1.315 (3)
N1—C3	1.466 (2)	N3—C15	1.442 (3)
O2—C6	1.330 (3)	N3—C17	1.456 (3)
O2—H18	0.8400	C3—C1	1.485 (3)
O3—C7	1.273 (2)	C3—C2	1.485 (3)
C8—C9	1.410 (3)	C3—H3A	1.0000
C8—C13	1.411 (3)	C14—C15	1.528 (3)
C8—C7	1.458 (3)	C14—H14A	0.9900
F1—C10	1.365 (2)	C14—H14B	0.9900
C13—C12	1.414 (3)	C2—C1	1.501 (3)
C11—C12	1.394 (3)	C2—H2A	0.9900
C11—N2	1.404 (2)	C2—H2B	0.9900
C11—C10	1.420 (3)	C15—H15A	0.9900
C5—C4	1.373 (3)	C15—H15B	0.9900
C5—C7	1.431 (3)	C16—C17	1.496 (3)
C5—C6	1.493 (3)	C16—H16A	0.9900
O1—C6	1.210 (3)	C16—H16B	0.9900
C12—H12A	0.9500	C17—H17A	0.9900
C9—C10	1.361 (3)	C17—H17B	0.9900
C9—H9A	0.9500	C1—H1A	0.9900
N2—C14	1.469 (3)	C1—H1B	0.9900
N2—C16	1.474 (3)	N4—O4	1.238 (3)

C4—N1—C13	119.38 (16)	C1—C3—C2	60.70 (16)
C4—N1—C3	120.52 (15)	N1—C3—H3A	115.5
C13—N1—C3	120.07 (15)	C1—C3—H3A	115.5
C6—O2—H18	109.5	C2—C3—H3A	115.5
C9—C8—C13	118.03 (17)	N2—C14—C15	110.91 (17)
C9—C8—C7	120.60 (17)	N2—C14—H14A	109.5
C13—C8—C7	121.36 (18)	C15—C14—H14A	109.5
N1—C13—C8	119.20 (16)	N2—C14—H14B	109.5
N1—C13—C12	120.02 (17)	C15—C14—H14B	109.5
C8—C13—C12	120.77 (17)	H14A—C14—H14B	108.0
C12—C11—N2	122.48 (18)	C3—C2—C1	59.64 (15)
C12—C11—C10	116.46 (17)	C3—C2—H2A	117.8
N2—C11—C10	120.98 (17)	C1—C2—H2A	117.8
C4—C5—C7	120.37 (17)	C3—C2—H2B	117.8
C4—C5—C6	117.68 (18)	C1—C2—H2B	117.8
C7—C5—C6	121.95 (18)	H2A—C2—H2B	114.9
C11—C12—C13	120.90 (18)	N3—C15—C14	110.6 (2)
C11—C12—H12A	119.6	N3—C15—H15A	109.5
C13—C12—H12A	119.6	C14—C15—H15A	109.5
C10—C9—C8	119.97 (18)	N3—C15—H15B	109.5
C10—C9—H9A	120.0	C14—C15—H15B	109.5
C8—C9—H9A	120.0	H15A—C15—H15B	108.1
C11—N2—C14	117.59 (15)	N2—C16—C17	111.9 (2)
C11—N2—C16	117.81 (17)	N2—C16—H16A	109.2
C14—N2—C16	111.17 (17)	C17—C16—H16A	109.2
O3—C7—C5	123.16 (18)	N2—C16—H16B	109.2
O3—C7—C8	121.43 (18)	C17—C16—H16B	109.2
C5—C7—C8	115.41 (17)	H16A—C16—H16B	107.9
C9—C10—F1	117.51 (17)	N3—C17—C16	108.62 (19)
C9—C10—C11	123.63 (18)	N3—C17—H17A	110.0
F1—C10—C11	118.81 (17)	C16—C17—H17A	110.0
N1—C4—C5	124.20 (18)	N3—C17—H17B	110.0
N1—C4—H4A	117.9	C16—C17—H17B	110.0
C5—C4—H4A	117.9	H17A—C17—H17B	108.3
O1—C6—O2	121.06 (19)	C3—C1—C2	59.66 (15)
O1—C6—C5	123.8 (2)	C3—C1—H1A	117.8
O2—C6—C5	115.15 (19)	C2—C1—H1A	117.8
N4—N3—C15	119.31 (19)	C3—C1—H1B	117.8
N4—N3—C17	125.3 (2)	C2—C1—H1B	117.8
C15—N3—C17	115.35 (18)	H1A—C1—H1B	114.9
N1—C3—C1	119.44 (18)	O4—N4—N3	115.6 (2)
N1—C3—C2	119.07 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H18···O3	0.84	1.78	2.562 (2)	153
C4—H4A···O1	0.95	2.48	2.812 (3)	101
C15—H15A···O2ⁱ	0.99	2.50	3.405 (3)	151
C15—H15B···O3ⁱⁱ	0.99	2.51	3.385 (3)	147
C16—H16A···O1ⁱⁱⁱ	0.99	2.60	3.264 (3)	125
C16—H16B···F1	0.99	2.14	2.852 (3)	128
C17—H17B···O4	0.99	2.30	2.692 (3)	102

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇FN₄O₄
M_r	360.35
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.378 (3), 9.625 (4), 10.328 (4)
α, β, γ (°)	102.99 (2), 96.089 (14), 97.392 (16)
V (Å³)	797.0 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Rigaku Mercury CCD/AFC diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.976, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	6267, 3631, 2568
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.207, 1.06
No. of reflections	3631
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.35

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H18···O3	0.84	1.78	2.562 (2)	153.4
C4—H4A···O1	0.95	2.48	2.812 (3)	100.7
C15—H15A···O2ⁱ	0.99	2.50	3.405 (3)	151.3
C15—H15B···O3ⁱⁱ	0.99	2.51	3.385 (3)	147.1
C16—H16A···O1ⁱⁱⁱ	0.99	2.60	3.264 (3)	124.8
C16—H16B···F1	0.99	2.14	2.852 (3)	127.7
C17—H17B···O4	0.99	2.30	2.692 (3)	102.1

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

Acknowledgements

The work was supported by a grant from the National Science Foundation of China (30771682).

References

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Drevenšek, P., Leban, I., Turel, I., Giester, G. & Tillmanns, E. (2003). Acta Cryst. C59, m376–m378. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, X.-W., Zhi, F., Shen, J.-H. & Hu, Y.-Q. (2005). Acta Cryst. E61, o2235–o2236. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lou, B., Boström, D. & Velaga, S. P. (2007). Acta Cryst. C63, o731–o733. Web of Science CSD CrossRef IUCr Journals Google Scholar
Neu, H. C. (1987). Am. J. Med. 82, 395-404. CAS PubMed Web of Science Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sekido, K., Okamoto, K. & Hirokawa, S. (1985). Acta Cryst. C41, 741–743. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turel, I., Leban, I., Zupancic, M., Bukovec, P. & Gruber, K. (1996). Acta Cryst. C52, 2443–2445. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o2053

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

1-Cyclo­propyl-6-fluoro-7-(4-nitro­so­piperazin-1-yl)-4-oxo-1,4-di­hydro­quinoline-3-carboxylic acid

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1-Cyclopropyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid