1-Ethyl-6-fluoro-7-(4-methyl­piperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate hexa­hydrate

An, Z.; Liang, Q.-C.

doi:10.1107/S1600536808000421

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o441

doi:10.1107/S1600536808000421

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1-Ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate hexahydrate

Zhe An ^a and Qing-Cheng Liang ^b ^*

^aSchool of Pharmaceutical Science, Harbin Medical University, Harbin, 150086, People's Republic of China, and ^bSecond Hospital, Harbin Medical University, Harbin, 150086, People's Republic of China
^*Correspondence e-mail: liangqingcheng@126.com

(Received 14 December 2007; accepted 7 January 2008; online 16 January 2008)

In the title compound, C₁₇H₂₀FN₃O₃·6H₂O, the pefloxacin (pef) neutral zwitterion is accompanied by six water molecules of hydration. An extensive network of O—H⋯O and N—H⋯O hydrogen bonds help to establish the crystal packing.

Related literature

For metal complexes of the pef anion, see: Baenziger et al. (1986 ); An, Huang & Qi (2007 ); An, Qi & Huang (2007 ). For background on the medicinal uses of Hpef, see: Mizuki et al. (1996 ).

Experimental

Crystal data

C₁₇H₂₀FN₃O₃·6H₂O
M_r = 441.46
Monoclinic, P 2₁ /n
a = 8.0925 (15) Å
b = 24.075 (5) Å
c = 10.8006 (19) Å
β = 92.064 (3)°
V = 2102.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 (2) K
0.34 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.960, T_max = 0.978
10920 measured reflections
3743 independent reflections
2239 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.134
S = 1.02
3743 reflections
312 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O1	0.857 (10)	1.866 (12)	2.700 (3)	164 (3)
O1W—H1W2⋯O3W	0.85 (3)	2.201 (16)	3.017 (3)	162 (3)
O2W—H2W1⋯O2	0.851 (10)	1.881 (13)	2.722 (3)	170 (4)
O2W—H2W2⋯O6W	0.86 (3)	1.91 (3)	2.765 (3)	171 (3)
O3W—H3W2⋯O1ⁱ	0.852 (10)	1.896 (13)	2.730 (3)	166 (3)
O3W—H3W1⋯O2W	0.86 (3)	1.82 (3)	2.679 (3)	175 (3)
O6W—H6W1⋯O1Wⁱ	0.86 (3)	1.92 (3)	2.765 (4)	170 (4)
O6W—H6W2⋯O4Wⁱⁱ	0.847 (10)	2.17 (3)	3.007 (4)	170 (4)
N3—H3N⋯O3Wⁱⁱⁱ	0.910 (10)	1.847 (13)	2.730 (3)	163 (3)
O4W—H4W1⋯O3	0.86 (3)	1.89 (3)	2.739 (3)	169 (3)
O4W—H4W2⋯O5Wⁱⁱ	0.85 (3)	1.959 (15)	2.783 (3)	163 (3)
O5W—H5W1⋯O2	0.85 (3)	1.97 (3)	2.792 (3)	164 (4)
O5W—H5W1⋯O3	0.85 (3)	2.63 (4)	3.142 (3)	120 (3)
O5W—H5W2⋯O5Wⁱⁱ	0.84 (3)	2.06 (2)	2.769 (5)	142 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y, -z+2; (iii) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808000421/hb2680sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000421/hb2680Isup2.hkl

checkCIF report

Comment top

Pefloxacin (Hpef, C₁₇H₂₀FN₃O₃, 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline -3-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The silver(I), manganese(II) and cobalt(II) derivatives of the pefloxacin (pef) anion have been reported (Baenziger et al., 1986; An, Huang & Qi, 2007; An, Qi & Huang, 2007).

We attempted to prepare a nickel(II) complex of pef, but the title compound, (I), arose instead. The neutral Hpef zwitterion shows nominal proton transfer from O1 or O2 to N3. Consequently the C1—O1 [1.264 (3) Å] and C1—O2 [1.245 (3) Å] bond lengths are very similar. The bond angle sum for N1 of 360° indicates sp² hybridization for this atom. The N2/N3/C11—C14 ring is a typical chair.

The components of (I) are linked by O—H···O and O—H···N hydrogen bonds (Table 1) involving all the potential donors, generating a three-dimensional supramolecular network.

Related literature top

For metal complexes of the pef anion, see: Baenziger et al. (1986); An, Huang & Qi (2007); An, Qi & Huang (2007). For background on the medicinal uses of Hpef, see: Mizuki et al. (1996).

Experimental top

A mixture of Ni(NO₃)₂.6H₂O (0.075 g, 0.25 mmol), Hpef (0.17 g, 0.5 mmol), and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 423 K for 72 h under autogenous pressure. The targeted Ni²⁺ complex was not synthesized and colorless prisms of (I) were obtained from the reaction mixture after cooling.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top

Fig. 1. The asymmetric unit of (I), showing 50% displacement ellipsoids.

1-Ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline- 3-carboxylate hexahydrate top

Crystal data top

C₁₇H₂₀FN₃O₃·6H₂O	F(000) = 944
M_r = 441.46	D_x = 1.394 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10069 reflections
a = 8.0925 (15) Å	θ = 2.1–25.1°
b = 24.075 (5) Å	µ = 0.12 mm⁻¹
c = 10.8006 (19) Å	T = 296 K
β = 92.064 (3)°	Prism, colorless
V = 2102.9 (7) Å³	0.34 × 0.26 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3743 independent reflections
Radiation source: fine-focus sealed tube	2239 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
T_min = 0.960, T_max = 0.978	k = −25→28
10920 measured reflections	l = −8→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0593P)² + 0.0315P] where P = (F_o² + 2F_c²)/3
3743 reflections	(Δ/σ)_max < 0.001
312 parameters	Δρ_max = 0.22 e Å⁻³
19 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₂₀FN₃O₃·6H₂O	V = 2102.9 (7) Å³
M_r = 441.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0925 (15) Å	µ = 0.12 mm⁻¹
b = 24.075 (5) Å	T = 296 K
c = 10.8006 (19) Å	0.34 × 0.26 × 0.18 mm
β = 92.064 (3)°

Data collection top

Bruker SMART CCD diffractometer	3743 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2239 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.978	R_int = 0.051
10920 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	19 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
3743 reflections	Δρ_min = −0.20 e Å⁻³
312 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.

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

	x	y	z	U_iso*/U_eq
F1	0.4982 (2)	0.12293 (6)	0.56081 (13)	0.0524 (5)
O1	0.9475 (3)	−0.18675 (8)	0.62111 (17)	0.0512 (5)
O2	0.9816 (3)	−0.13364 (8)	0.78658 (17)	0.0548 (6)
O3	0.7598 (2)	−0.04158 (7)	0.76314 (16)	0.0436 (5)
O1W	1.0319 (4)	−0.28815 (9)	0.7094 (2)	0.0761 (7)
H1W1	1.010 (5)	−0.2538 (6)	0.695 (3)	0.114*
H1W2	1.104 (4)	−0.2906 (13)	0.768 (3)	0.114*
O2W	1.0567 (3)	−0.19330 (10)	0.9952 (2)	0.0687 (7)
H2W1	1.042 (4)	−0.1772 (13)	0.9256 (17)	0.103*
H2W2	1.121 (4)	−0.1734 (12)	1.042 (2)	0.103*
O3W	1.2764 (3)	−0.26876 (9)	0.92250 (17)	0.0558 (6)
H3W2	1.318 (4)	−0.2872 (11)	0.9835 (19)	0.084*
H3W1	1.204 (3)	−0.2460 (12)	0.950 (2)	0.084*
O4W	0.6261 (3)	0.02774 (10)	0.9339 (2)	0.0637 (6)
O5W	1.0677 (3)	−0.04707 (12)	0.9484 (2)	0.0817 (8)
H5W1	1.022 (4)	−0.0705 (13)	0.899 (3)	0.123*
H5W2	0.997 (3)	−0.0308 (15)	0.990 (4)	0.123*
O6W	1.2719 (3)	−0.13973 (11)	1.1601 (3)	0.0914 (9)
H6W1	1.360 (3)	−0.1585 (13)	1.176 (4)	0.137*
H6W2	1.298 (5)	−0.1066 (7)	1.143 (4)	0.137*
N1	0.8676 (2)	−0.05154 (8)	0.39571 (18)	0.0325 (5)
N2	0.5711 (3)	0.12232 (8)	0.31502 (18)	0.0351 (5)
N3	0.4587 (3)	0.20866 (9)	0.1516 (2)	0.0399 (6)
H3N	0.552 (2)	0.2224 (11)	0.119 (2)	0.060*
C1	0.9405 (3)	−0.14034 (11)	0.6754 (3)	0.0361 (6)
C2	0.8807 (3)	−0.09193 (10)	0.6006 (2)	0.0318 (6)
C3	0.7935 (3)	−0.04596 (10)	0.6512 (2)	0.0320 (6)
C4	0.7415 (3)	−0.00337 (10)	0.5619 (2)	0.0303 (6)
C5	0.6494 (3)	0.04228 (10)	0.6011 (2)	0.0350 (6)
H5	0.6234	0.0454	0.6840	0.042*
C6	0.5981 (3)	0.08168 (11)	0.5202 (2)	0.0354 (6)
C7	0.6356 (3)	0.08101 (11)	0.3938 (2)	0.0327 (6)
C8	0.7274 (3)	0.03613 (10)	0.3540 (2)	0.0318 (6)
H8	0.7556	0.0341	0.2714	0.038*
C9	0.7785 (3)	−0.00614 (10)	0.4361 (2)	0.0294 (6)
C10	0.9112 (3)	−0.09195 (10)	0.4773 (2)	0.0337 (6)
H10	0.9671	−0.1225	0.4467	0.040*
C11	0.6038 (3)	0.18058 (10)	0.3458 (2)	0.0404 (7)
H11B	0.7100	0.1916	0.3149	0.048*
H11A	0.6076	0.1853	0.4351	0.048*
C12	0.4696 (4)	0.21632 (11)	0.2885 (2)	0.0422 (7)
H12B	0.3646	0.2067	0.3233	0.051*
H12A	0.4924	0.2550	0.3076	0.051*
C13	0.4413 (3)	0.14871 (11)	0.1185 (2)	0.0390 (7)
H13B	0.4475	0.1445	0.0295	0.047*
H13A	0.3338	0.1355	0.1424	0.047*
C14	0.5745 (3)	0.11382 (11)	0.1818 (2)	0.0391 (7)
H14B	0.5560	0.0749	0.1627	0.047*
H14A	0.6818	0.1243	0.1522	0.047*
C15	0.3210 (4)	0.24236 (14)	0.0946 (3)	0.0607 (9)
H15A	0.3180	0.2374	0.0064	0.091*
H15B	0.3387	0.2809	0.1138	0.091*
H15C	0.2179	0.2305	0.1270	0.091*
C16	0.9107 (3)	−0.05917 (12)	0.2649 (2)	0.0390 (7)
H16B	1.0083	−0.0824	0.2617	0.047*
H16A	0.9375	−0.0233	0.2299	0.047*
C17	0.7735 (4)	−0.08525 (15)	0.1874 (3)	0.0642 (10)
H17A	0.7489	−0.1213	0.2198	0.096*
H17B	0.8072	−0.0888	0.1035	0.096*
H17C	0.6766	−0.0623	0.1895	0.096*
H4W1	0.657 (4)	0.0071 (13)	0.874 (2)	0.096*
H4W2	0.709 (3)	0.0325 (14)	0.984 (2)	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0657 (11)	0.0498 (11)	0.0420 (10)	0.0227 (9)	0.0072 (8)	−0.0003 (7)
O1	0.0692 (14)	0.0320 (12)	0.0515 (13)	0.0057 (10)	−0.0116 (10)	0.0010 (9)
O2	0.0748 (15)	0.0505 (13)	0.0380 (13)	0.0082 (11)	−0.0155 (10)	0.0037 (9)
O3	0.0604 (13)	0.0411 (12)	0.0293 (11)	0.0039 (10)	0.0017 (9)	0.0017 (8)
O1W	0.097 (2)	0.0451 (14)	0.0843 (19)	−0.0009 (14)	−0.0253 (14)	0.0077 (12)
O2W	0.0744 (18)	0.0650 (16)	0.0660 (16)	0.0009 (13)	−0.0099 (13)	0.0230 (12)
O3W	0.0567 (15)	0.0574 (15)	0.0531 (14)	−0.0038 (11)	−0.0015 (10)	0.0151 (10)
O4W	0.0667 (15)	0.0719 (17)	0.0519 (15)	0.0112 (13)	−0.0060 (11)	−0.0213 (11)
O5W	0.091 (2)	0.081 (2)	0.0720 (19)	−0.0046 (16)	−0.0108 (14)	−0.0229 (12)
O6W	0.107 (2)	0.0690 (18)	0.096 (2)	0.0147 (16)	−0.0310 (17)	−0.0081 (16)
N1	0.0363 (13)	0.0324 (12)	0.0290 (12)	0.0011 (10)	0.0018 (9)	−0.0018 (10)
N2	0.0484 (14)	0.0282 (12)	0.0280 (12)	−0.0011 (11)	−0.0074 (10)	−0.0007 (9)
N3	0.0408 (15)	0.0389 (14)	0.0400 (14)	0.0036 (11)	0.0015 (11)	0.0076 (10)
C1	0.0346 (16)	0.0341 (16)	0.0395 (17)	−0.0036 (13)	−0.0005 (12)	0.0017 (13)
C2	0.0330 (15)	0.0322 (15)	0.0298 (15)	−0.0020 (12)	−0.0040 (11)	0.0008 (11)
C3	0.0324 (15)	0.0327 (15)	0.0305 (15)	−0.0051 (12)	−0.0031 (11)	−0.0002 (12)
C4	0.0325 (15)	0.0285 (14)	0.0295 (14)	−0.0049 (12)	−0.0025 (11)	−0.0001 (11)
C5	0.0409 (16)	0.0380 (16)	0.0258 (14)	0.0016 (13)	−0.0013 (11)	−0.0029 (12)
C6	0.0377 (16)	0.0359 (16)	0.0325 (15)	0.0056 (13)	−0.0003 (12)	−0.0046 (12)
C7	0.0316 (14)	0.0332 (15)	0.0327 (15)	−0.0062 (12)	−0.0045 (11)	0.0026 (12)
C8	0.0338 (15)	0.0317 (15)	0.0299 (14)	−0.0024 (12)	0.0026 (11)	0.0000 (11)
C9	0.0278 (14)	0.0304 (14)	0.0299 (14)	−0.0053 (12)	0.0009 (11)	−0.0011 (11)
C10	0.0340 (15)	0.0266 (14)	0.0405 (16)	0.0019 (12)	−0.0015 (12)	−0.0020 (12)
C11	0.0492 (18)	0.0333 (16)	0.0378 (16)	−0.0046 (14)	−0.0090 (12)	−0.0014 (12)
C12	0.0522 (19)	0.0367 (16)	0.0379 (17)	0.0030 (14)	0.0035 (13)	−0.0014 (12)
C13	0.0450 (17)	0.0415 (17)	0.0304 (15)	−0.0026 (14)	−0.0021 (12)	0.0020 (12)
C14	0.0504 (17)	0.0338 (16)	0.0329 (16)	0.0014 (13)	−0.0010 (12)	0.0005 (12)
C15	0.053 (2)	0.061 (2)	0.068 (2)	0.0162 (17)	−0.0062 (16)	0.0190 (16)
C16	0.0476 (17)	0.0404 (16)	0.0294 (15)	0.0017 (13)	0.0086 (12)	−0.0007 (12)
C17	0.073 (2)	0.077 (2)	0.0430 (19)	−0.019 (2)	0.0019 (16)	−0.0111 (16)

Geometric parameters (Å, º) top

F1—C6	1.363 (3)	C3—C4	1.459 (3)
C1—O1	1.264 (3)	C4—C5	1.402 (3)
C1—O2	1.245 (3)	C4—C9	1.404 (3)
C3—O3	1.253 (3)	C5—C6	1.345 (3)
O1W—H1W1	0.857 (10)	C5—H5	0.9300
O1W—H1W2	0.85 (3)	C6—C7	1.409 (3)
O2W—H2W1	0.851 (10)	C7—C8	1.388 (3)
O2W—H2W2	0.86 (3)	C8—C9	1.402 (3)
O3W—H3W2	0.852 (10)	C8—H8	0.9300
O3W—H3W1	0.86 (3)	C10—H10	0.9300
O4W—H4W1	0.86 (3)	C11—C12	1.501 (4)
O4W—H4W2	0.851 (10)	C11—H11B	0.9700
O5W—H5W1	0.85 (3)	C11—H11A	0.9700
O5W—H5W2	0.84 (3)	C12—H12B	0.9700
O6W—H6W1	0.86 (3)	C12—H12A	0.9700
O6W—H6W2	0.847 (10)	C13—C14	1.510 (4)
N1—C10	1.351 (3)	C13—H13B	0.9700
N1—C9	1.388 (3)	C13—H13A	0.9700
N1—C16	1.479 (3)	C14—H14B	0.9700
N2—C7	1.397 (3)	C14—H14A	0.9700
N2—C14	1.454 (3)	C15—H15A	0.9600
N2—C11	1.463 (3)	C15—H15B	0.9600
N3—C12	1.490 (3)	C15—H15C	0.9600
N3—C13	1.492 (3)	C16—C17	1.504 (4)
N3—C15	1.493 (3)	C16—H16B	0.9700
N3—H3N	0.910 (10)	C16—H16A	0.9700
C1—C2	1.489 (4)	C17—H17A	0.9600
C2—C10	1.363 (3)	C17—H17B	0.9600
C2—C3	1.431 (3)	C17—H17C	0.9600

H1W1—O1W—H1W2	109.3 (17)	N1—C10—C2	125.8 (2)
H2W1—O2W—H2W2	109.4 (16)	N1—C10—H10	117.1
H3W2—O3W—H3W1	108.6 (16)	C2—C10—H10	117.1
H4W1—O4W—H4W2	108.2 (16)	N2—C11—C12	109.5 (2)
H5W1—O5W—H5W2	110.9 (18)	N2—C11—H11B	109.8
H6W1—O6W—H6W2	109.4 (17)	C12—C11—H11B	109.8
C10—N1—C9	119.2 (2)	N2—C11—H11A	109.8
C10—N1—C16	118.0 (2)	C12—C11—H11A	109.8
C9—N1—C16	122.7 (2)	H11B—C11—H11A	108.2
C7—N2—C14	118.8 (2)	N3—C12—C11	110.8 (2)
C7—N2—C11	118.89 (19)	N3—C12—H12B	109.5
C14—N2—C11	110.49 (19)	C11—C12—H12B	109.5
C12—N3—C13	111.04 (19)	N3—C12—H12A	109.5
C12—N3—C15	111.0 (2)	C11—C12—H12A	109.5
C13—N3—C15	111.4 (2)	H12B—C12—H12A	108.1
C12—N3—H3N	108.4 (19)	N3—C13—C14	111.7 (2)
C13—N3—H3N	109.5 (19)	N3—C13—H13B	109.3
C15—N3—H3N	105.3 (19)	C14—C13—H13B	109.3
O2—C1—O1	123.2 (2)	N3—C13—H13A	109.3
O2—C1—C2	119.5 (2)	C14—C13—H13A	109.3
O1—C1—C2	117.3 (2)	H13B—C13—H13A	107.9
C10—C2—C3	118.9 (2)	N2—C14—C13	109.3 (2)
C10—C2—C1	117.6 (2)	N2—C14—H14B	109.8
C3—C2—C1	123.6 (2)	C13—C14—H14B	109.8
O3—C3—C2	124.1 (2)	N2—C14—H14A	109.8
O3—C3—C4	120.7 (2)	C13—C14—H14A	109.8
C2—C3—C4	115.2 (2)	H14B—C14—H14A	108.3
C5—C4—C9	117.6 (2)	N3—C15—H15A	109.5
C5—C4—C3	119.7 (2)	N3—C15—H15B	109.5
C9—C4—C3	122.7 (2)	H15A—C15—H15B	109.5
C6—C5—C4	120.8 (2)	N3—C15—H15C	109.5
C6—C5—H5	119.6	H15A—C15—H15C	109.5
C4—C5—H5	119.6	H15B—C15—H15C	109.5
C5—C6—F1	118.5 (2)	N1—C16—C17	112.9 (2)
C5—C6—C7	123.3 (2)	N1—C16—H16B	109.0
F1—C6—C7	118.1 (2)	C17—C16—H16B	109.0
C8—C7—N2	123.9 (2)	N1—C16—H16A	109.0
C8—C7—C6	116.4 (2)	C17—C16—H16A	109.0
N2—C7—C6	119.5 (2)	H16B—C16—H16A	107.8
C7—C8—C9	121.2 (2)	C16—C17—H17A	109.5
C7—C8—H8	119.4	C16—C17—H17B	109.5
C9—C8—H8	119.4	H17A—C17—H17B	109.5
N1—C9—C8	121.2 (2)	C16—C17—H17C	109.5
N1—C9—C4	118.2 (2)	H17A—C17—H17C	109.5
C8—C9—C4	120.6 (2)	H17B—C17—H17C	109.5

O2—C1—C2—C10	149.2 (3)	C10—N1—C9—C8	−178.5 (2)
O1—C1—C2—C10	−30.5 (3)	C16—N1—C9—C8	−1.6 (3)
O2—C1—C2—C3	−30.8 (4)	C10—N1—C9—C4	1.9 (3)
O1—C1—C2—C3	149.5 (2)	C16—N1—C9—C4	178.8 (2)
C10—C2—C3—O3	−179.6 (2)	C7—C8—C9—N1	178.8 (2)
C1—C2—C3—O3	0.5 (4)	C7—C8—C9—C4	−1.7 (3)
C10—C2—C3—C4	1.5 (3)	C5—C4—C9—N1	−179.1 (2)
C1—C2—C3—C4	−178.4 (2)	C3—C4—C9—N1	0.3 (3)
O3—C3—C4—C5	−1.5 (3)	C5—C4—C9—C8	1.3 (3)
C2—C3—C4—C5	177.4 (2)	C3—C4—C9—C8	−179.3 (2)
O3—C3—C4—C9	179.1 (2)	C9—N1—C10—C2	−2.5 (4)
C2—C3—C4—C9	−2.0 (3)	C16—N1—C10—C2	−179.6 (2)
C9—C4—C5—C6	0.3 (4)	C3—C2—C10—N1	0.6 (4)
C3—C4—C5—C6	−179.1 (2)	C1—C2—C10—N1	−179.4 (2)
C4—C5—C6—F1	175.0 (2)	C7—N2—C11—C12	−154.7 (2)
C4—C5—C6—C7	−1.7 (4)	C14—N2—C11—C12	62.7 (3)
C14—N2—C7—C8	11.0 (4)	C13—N3—C12—C11	53.2 (3)
C11—N2—C7—C8	−128.5 (3)	C15—N3—C12—C11	177.7 (2)
C14—N2—C7—C6	−164.6 (2)	N2—C11—C12—N3	−58.1 (3)
C11—N2—C7—C6	56.0 (3)	C12—N3—C13—C14	−52.3 (3)
C5—C6—C7—C8	1.3 (4)	C15—N3—C13—C14	−176.6 (2)
F1—C6—C7—C8	−175.4 (2)	C7—N2—C14—C13	156.2 (2)
C5—C6—C7—N2	177.2 (2)	C11—N2—C14—C13	−61.2 (3)
F1—C6—C7—N2	0.4 (3)	N3—C13—C14—N2	56.0 (3)
N2—C7—C8—C9	−175.3 (2)	C10—N1—C16—C17	93.5 (3)
C6—C7—C8—C9	0.4 (3)	C9—N1—C16—C17	−83.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1	0.86 (1)	1.87 (1)	2.700 (3)	164 (3)
O1W—H1W2···O3W	0.85 (3)	2.20 (2)	3.017 (3)	162 (3)
O2W—H2W1···O2	0.85 (1)	1.88 (1)	2.722 (3)	170 (4)
O2W—H2W2···O6W	0.86 (3)	1.91 (3)	2.765 (3)	171 (3)
O3W—H3W2···O1ⁱ	0.85 (1)	1.90 (1)	2.730 (3)	166 (3)
O3W—H3W1···O2W	0.86 (3)	1.82 (3)	2.679 (3)	175 (3)
O6W—H6W1···O1Wⁱ	0.86 (3)	1.92 (3)	2.765 (4)	170 (4)
O6W—H6W2···O4Wⁱⁱ	0.85 (1)	2.17 (3)	3.007 (4)	170 (4)
N3—H3N···O3Wⁱⁱⁱ	0.91 (1)	1.85 (1)	2.730 (3)	163 (3)
O4W—H4W1···O3	0.86 (3)	1.89 (3)	2.739 (3)	169 (3)
O4W—H4W2···O5Wⁱⁱ	0.85 (3)	1.96 (2)	2.783 (3)	163 (3)
O5W—H5W1···O2	0.85 (3)	1.97 (3)	2.792 (3)	164 (4)
O5W—H5W1···O3	0.85 (3)	2.63 (4)	3.142 (3)	120 (3)
O5W—H5W2···O5Wⁱⁱ	0.84 (3)	2.06 (2)	2.769 (5)	142 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀FN₃O₃·6H₂O
M_r	441.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.0925 (15), 24.075 (5), 10.8006 (19)
β (°)	92.064 (3)
V (Å³)	2102.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.34 × 0.26 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.960, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	10920, 3743, 2239
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.134, 1.02
No. of reflections	3743
No. of parameters	312
No. of restraints	19
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O1	0.857 (10)	1.866 (12)	2.700 (3)	164 (3)
O1W—H1W2···O3W	0.85 (3)	2.201 (16)	3.017 (3)	162 (3)
O2W—H2W1···O2	0.851 (10)	1.881 (13)	2.722 (3)	170 (4)
O2W—H2W2···O6W	0.86 (3)	1.91 (3)	2.765 (3)	171 (3)
O3W—H3W2···O1ⁱ	0.852 (10)	1.896 (13)	2.730 (3)	166 (3)
O3W—H3W1···O2W	0.86 (3)	1.82 (3)	2.679 (3)	175 (3)
O6W—H6W1···O1Wⁱ	0.86 (3)	1.92 (3)	2.765 (4)	170 (4)
O6W—H6W2···O4Wⁱⁱ	0.847 (10)	2.17 (3)	3.007 (4)	170 (4)
N3—H3N···O3Wⁱⁱⁱ	0.910 (10)	1.847 (13)	2.730 (3)	163 (3)
O4W—H4W1···O3	0.86 (3)	1.89 (3)	2.739 (3)	169 (3)
O4W—H4W2···O5Wⁱⁱ	0.85 (3)	1.959 (15)	2.783 (3)	163 (3)
O5W—H5W1···O2	0.85 (3)	1.97 (3)	2.792 (3)	164 (4)
O5W—H5W1···O3	0.85 (3)	2.63 (4)	3.142 (3)	120 (3)
O5W—H5W2···O5Wⁱⁱ	0.84 (3)	2.06 (2)	2.769 (5)	142 (3)

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

Acknowledgements

The authors acknowledge financial support by the Science Foundation of Heilongjiang Provincial Department of Science & Technology (grant No. GC07C35204).

References

An, Z., Huang, J. & Qi, W. (2007). Acta Cryst. E63, m2009. Web of Science CSD CrossRef IUCr Journals Google Scholar
An, Z., Qi, W. & Huang, J. (2007). Acta Cryst. E63, m2084–m2085. Web of Science CSD CrossRef IUCr Journals Google Scholar
Baenziger, N. C., Fox, C. L. & Modak, S. L. (1986). Acta Cryst. C42, 1505–1509. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruker (1998). SMART, SAINT-Plus, SADABS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41–45. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 2| February 2008| Page o441

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

1-Ethyl-6-fluoro-7-(4-methyl­piperazin-4-ium-1-yl)-4-oxo-1,4-di­hydro­quinoline-3-carboxylate hexa­hydrate

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Experimental

Crystal data

Data collection

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organic compounds

1-Ethyl-6-fluoro-7-(4-methylpiperazin-4-ium-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate hexahydrate