Poly[bis-[μ-1-cyclo-propyl-6-fluoro-4-oxido-7-(1-piperazin-yl)-1,4-dihydro-quinoline-3-carboxyl-ato]nickel(II)].

In the title compound, [Ni(C(17)H(17)FN(3)O(3))(2)](n), the Ni(II) atom exists in a distorted trans-NiN(2)O(4) octa-hedral geometry defined by two monodentate N-bonded and two bidentate O,O-bonded 1-cyclo-propyl-6-fluoro-4-oxido-7-(1-piperazin-yl)-1,4-dihydro-quinoline-3-carboxyl-ate (ciprofloxacinium) monoanions. The extended two-dimensional structure is a square grid. The Ni atom lies on a center of inversion.

Related literature

For the manganese, zinc and copper complexes of the ciprofloxacinium (cf) anion, see: Xiao et al. (2005 ▶); An et al. (2007 ▶). For background on the medicinal uses of Hcf, see: Mizuki et al. (1996 ▶).

Experimental

Crystal data

[Ni(C17H17FN3O3)2]

M = 719.38

Monoclinic,

a = 5.9999 (6) Å

b = 21.437 (2) Å

c = 13.2287 (14) Å

β = 101.886 (2)°

V = 1665.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.65 mm−1

T = 295 (2) K

0.34 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.810, T max = 0.892

8098 measured reflections

2890 independent reflections

2466 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.173

S = 1.00

2890 reflections

226 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.92 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065555/cs2060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065555/cs2060Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C17H17FN3O3)2]	F000 = 748
Mr = 719.38	Dx = 1.435 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 5.9999 (6) Å	Cell parameters from 2967 reflections
b = 21.437 (2) Å	θ = 2.5–27.3º
c = 13.2287 (14) Å	µ = 0.65 mm−1
β = 101.886 (2)º	T = 295 (2) K
V = 1665.0 (3) Å3	Block, green
Z = 2	0.34 × 0.26 × 0.18 mm

Bruker SMART CCD diffractometer	2890 independent reflections
Radiation source: fine-focus sealed tube	2466 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 295(2) K	θmax = 25.1º
ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.810, Tmax = 0.892	k = −25→21
8098 measured reflections	l = −15→15

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.1083P)2 + 3.3784P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.008
2890 reflections	Δρmax = 1.92 e Å−3
226 parameters	Δρmin = −0.43 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Ni1	0.0000	0.5000	0.5000	0.0191 (2)
F1	0.7020 (4)	0.74254 (11)	0.67877 (19)	0.0407 (6)
O1	−0.2122 (4)	0.48858 (11)	0.6010 (2)	0.0254 (6)
O2	−0.3432 (6)	0.49499 (14)	0.7453 (3)	0.0489 (9)
O3	0.1687 (4)	0.56702 (11)	0.59535 (18)	0.0246 (5)
N1	0.0052 (5)	0.65173 (14)	0.8485 (2)	0.0275 (7)
N2	0.5762 (5)	0.81201 (14)	0.8367 (2)	0.0266 (7)
N3	0.7552 (5)	0.93356 (13)	0.9140 (2)	0.0244 (6)
C1	−0.2146 (6)	0.51226 (17)	0.6881 (3)	0.0261 (8)
C2	−0.0603 (6)	0.56768 (15)	0.7245 (3)	0.0236 (7)
C3	−0.1042 (6)	0.59953 (17)	0.8074 (3)	0.0274 (8)
H3	−0.2188	0.5841	0.8383	0.033*
C4	0.1761 (6)	0.67679 (16)	0.8044 (3)	0.0242 (7)
C5	0.2833 (6)	0.73317 (17)	0.8400 (3)	0.0264 (8)
H5	0.2370	0.7542	0.8937	0.032*
C6	0.4567 (6)	0.75847 (16)	0.7975 (3)	0.0243 (7)
C7	0.5192 (6)	0.72338 (17)	0.7174 (3)	0.0253 (8)
C8	0.4147 (6)	0.67009 (16)	0.6793 (3)	0.0251 (7)
H8	0.4605	0.6498	0.6249	0.030*
C9	0.2363 (6)	0.64486 (16)	0.7215 (3)	0.0232 (7)
C10	0.1164 (6)	0.58960 (15)	0.6756 (3)	0.0216 (7)
C11	−0.0674 (7)	0.6856 (2)	0.9317 (3)	0.0345 (9)
H11	−0.1386	0.7262	0.9124	0.041*
C12	0.0698 (10)	0.6814 (3)	1.0393 (4)	0.0550 (13)
H12A	0.0834	0.7187	1.0817	0.066*
H12B	0.2035	0.6548	1.0512	0.066*
C13	−0.1585 (10)	0.6507 (3)	1.0120 (4)	0.0632 (16)
H13A	−0.1629	0.6055	1.0075	0.076*
H13B	−0.2829	0.6694	1.0379	0.076*
C14	0.6114 (8)	0.86219 (18)	0.7651 (3)	0.0360 (9)
H14A	0.4703	0.8850	0.7425	0.043*
H14B	0.6543	0.8441	0.7047	0.043*
C15	0.7969 (7)	0.90671 (18)	0.8177 (3)	0.0347 (9)
H15A	0.9409	0.8846	0.8324	0.042*
H15B	0.8105	0.9403	0.7703	0.042*
C16	0.7067 (9)	0.8829 (2)	0.9801 (3)	0.0464 (12)
H16A	0.6634	0.9008	1.0406	0.056*
H16B	0.8452	0.8591	1.0035	0.056*
C17	0.5196 (8)	0.8385 (2)	0.9285 (3)	0.0458 (12)
H17A	0.5018	0.8054	0.9762	0.055*
H17B	0.3764	0.8609	0.9104	0.055*
H3N	0.641 (6)	0.9588 (19)	0.902 (4)	0.055*

	U11	U22	U33	U12	U13	U23
Ni1	0.0266 (4)	0.0117 (4)	0.0186 (4)	0.0001 (2)	0.0035 (3)	−0.0027 (2)
F1	0.0451 (13)	0.0358 (13)	0.0491 (14)	−0.0169 (10)	0.0284 (11)	−0.0146 (11)
O1	0.0311 (13)	0.0194 (12)	0.0252 (13)	−0.0048 (10)	0.0042 (10)	−0.0037 (10)
O2	0.067 (2)	0.0467 (19)	0.0417 (18)	−0.0339 (15)	0.0306 (17)	−0.0182 (13)
O3	0.0307 (13)	0.0206 (12)	0.0240 (12)	−0.0021 (10)	0.0090 (10)	−0.0075 (10)
N1	0.0331 (16)	0.0258 (16)	0.0263 (16)	−0.0096 (12)	0.0123 (13)	−0.0114 (12)
N2	0.0389 (17)	0.0178 (14)	0.0245 (15)	−0.0098 (12)	0.0101 (13)	−0.0055 (12)
N3	0.0304 (16)	0.0155 (14)	0.0268 (15)	−0.0031 (11)	0.0044 (12)	−0.0007 (12)
C1	0.0301 (19)	0.0209 (17)	0.0271 (19)	−0.0049 (14)	0.0055 (15)	−0.0005 (14)
C2	0.0299 (18)	0.0164 (17)	0.0236 (17)	−0.0038 (13)	0.0040 (14)	−0.0030 (13)
C3	0.0317 (18)	0.0248 (18)	0.0267 (18)	−0.0058 (14)	0.0081 (15)	−0.0016 (15)
C4	0.0285 (18)	0.0204 (17)	0.0246 (18)	−0.0042 (14)	0.0077 (14)	−0.0044 (14)
C5	0.0320 (19)	0.0224 (17)	0.0260 (18)	−0.0060 (15)	0.0088 (15)	−0.0087 (14)
C6	0.0286 (18)	0.0185 (17)	0.0251 (18)	−0.0042 (14)	0.0044 (14)	−0.0041 (14)
C7	0.0291 (18)	0.0239 (18)	0.0253 (18)	−0.0054 (14)	0.0108 (14)	−0.0036 (14)
C8	0.0312 (18)	0.0216 (17)	0.0241 (17)	−0.0019 (14)	0.0092 (14)	−0.0039 (14)
C9	0.0257 (17)	0.0217 (17)	0.0227 (17)	−0.0029 (13)	0.0058 (13)	−0.0039 (13)
C10	0.0261 (17)	0.0156 (16)	0.0221 (17)	0.0016 (13)	0.0024 (13)	−0.0002 (13)
C11	0.040 (2)	0.033 (2)	0.034 (2)	−0.0064 (17)	0.0166 (17)	−0.0116 (17)
C12	0.078 (3)	0.056 (3)	0.030 (2)	−0.009 (3)	0.009 (2)	−0.014 (2)
C13	0.094 (4)	0.063 (3)	0.046 (3)	−0.029 (3)	0.045 (3)	−0.017 (2)
C14	0.058 (3)	0.0240 (19)	0.0253 (19)	−0.0120 (17)	0.0057 (18)	−0.0016 (15)
C15	0.050 (2)	0.029 (2)	0.029 (2)	−0.0149 (17)	0.0159 (17)	−0.0059 (16)
C16	0.074 (3)	0.039 (2)	0.029 (2)	−0.035 (2)	0.018 (2)	−0.0119 (18)
C17	0.064 (3)	0.041 (2)	0.040 (2)	−0.032 (2)	0.028 (2)	−0.0232 (19)

Ni1—O3	2.038 (2)	C5—C6	1.391 (5)
Ni1—O3i	2.038 (2)	C5—H5	0.9300
Ni1—O1i	2.041 (3)	C6—C7	1.411 (5)
Ni1—O1	2.041 (3)	C7—C8	1.350 (5)
Ni1—N3ii	2.189 (3)	C8—C9	1.412 (5)
Ni1—N3iii	2.189 (3)	C8—H8	0.9300
F1—C7	1.365 (4)	C9—C10	1.453 (5)
O1—C1	1.261 (5)	C11—C13	1.491 (6)
O2—C1	1.243 (5)	C11—C12	1.492 (7)
O3—C10	1.264 (4)	C11—H11	0.9800
N1—C3	1.353 (5)	C12—C13	1.495 (7)
N1—C4	1.387 (5)	C12—H12A	0.9700
N1—C11	1.459 (5)	C12—H12B	0.9700
N2—C6	1.396 (4)	C13—H13A	0.9700
N2—C17	1.443 (5)	C13—H13B	0.9700
N2—C14	1.476 (5)	C14—C15	1.521 (5)
N3—C16	1.461 (5)	C14—H14A	0.9700
N3—C15	1.466 (5)	C14—H14B	0.9700
N3—Ni1iv	2.189 (3)	C15—H15A	0.9700
N3—H3N	0.861 (10)	C15—H15B	0.9700
C1—C2	1.522 (5)	C16—C17	1.521 (6)
C2—C3	1.363 (5)	C16—H16A	0.9700
C2—C10	1.430 (5)	C16—H16B	0.9700
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.404 (5)	C17—H17B	0.9700
C4—C9	1.402 (5)
O3—Ni1—O3i	180.00 (9)	C7—C8—H8	119.7
O3—Ni1—O1i	91.34 (10)	C9—C8—H8	119.7
O3i—Ni1—O1i	88.66 (10)	C4—C9—C8	117.4 (3)
O3—Ni1—O1	88.66 (10)	C4—C9—C10	122.7 (3)
O3i—Ni1—O1	91.34 (10)	C8—C9—C10	119.8 (3)
O1i—Ni1—O1	180.000 (1)	O3—C10—C2	126.1 (3)
O3—Ni1—N3ii	93.30 (11)	O3—C10—C9	118.4 (3)
O3i—Ni1—N3ii	86.70 (11)	C2—C10—C9	115.4 (3)
O1i—Ni1—N3ii	91.38 (11)	N1—C11—C13	119.9 (4)
O1—Ni1—N3ii	88.62 (11)	N1—C11—C12	119.9 (4)
O3—Ni1—N3iii	86.70 (11)	C13—C11—C12	60.2 (3)
O3i—Ni1—N3iii	93.30 (11)	N1—C11—H11	115.3
O1i—Ni1—N3iii	88.62 (11)	C13—C11—H11	115.3
O1—Ni1—N3iii	91.38 (11)	C12—C11—H11	115.3
N3ii—Ni1—N3iii	180.000 (1)	C11—C12—C13	59.9 (3)
C1—O1—Ni1	132.5 (2)	C11—C12—H12A	117.8
C10—O3—Ni1	127.7 (2)	C13—C12—H12A	117.8
C3—N1—C4	119.4 (3)	C11—C12—H12B	117.8
C3—N1—C11	121.3 (3)	C13—C12—H12B	117.8
C4—N1—C11	119.1 (3)	H12A—C12—H12B	114.9
C6—N2—C17	116.4 (3)	C11—C13—C12	60.0 (3)
C6—N2—C14	119.4 (3)	C11—C13—H13A	117.8
C17—N2—C14	110.0 (3)	C12—C13—H13A	117.8
C16—N3—C15	108.6 (3)	C11—C13—H13B	117.8
C16—N3—Ni1iv	111.6 (2)	C12—C13—H13B	117.8
C15—N3—Ni1iv	119.4 (2)	H13A—C13—H13B	114.9
C16—N3—H3N	109 (4)	N2—C14—C15	110.6 (3)
C15—N3—H3N	111 (4)	N2—C14—H14A	109.5
Ni1iv—N3—H3N	96 (4)	C15—C14—H14A	109.5
O2—C1—O1	124.1 (3)	N2—C14—H14B	109.5
O2—C1—C2	116.9 (3)	C15—C14—H14B	109.5
O1—C1—C2	118.9 (3)	H14A—C14—H14B	108.1
C3—C2—C10	118.9 (3)	N3—C15—C14	113.8 (3)
C3—C2—C1	116.1 (3)	N3—C15—H15A	108.8
C10—C2—C1	124.9 (3)	C14—C15—H15A	108.8
N1—C3—C2	125.4 (3)	N3—C15—H15B	108.8
N1—C3—H3	117.3	C14—C15—H15B	108.8
C2—C3—H3	117.3	H15A—C15—H15B	107.7
N1—C4—C5	121.3 (3)	N3—C16—C17	114.6 (4)
N1—C4—C9	118.1 (3)	N3—C16—H16A	108.6
C5—C4—C9	120.6 (3)	C17—C16—H16A	108.6
C6—C5—C4	121.9 (3)	N3—C16—H16B	108.6
C6—C5—H5	119.0	C17—C16—H16B	108.6
C4—C5—H5	119.0	H16A—C16—H16B	107.6
C5—C6—N2	122.7 (3)	N2—C17—C16	110.1 (3)
C5—C6—C7	115.6 (3)	N2—C17—H17A	109.6
N2—C6—C7	121.4 (3)	C16—C17—H17A	109.6
C8—C7—F1	117.5 (3)	N2—C17—H17B	109.6
C8—C7—C6	123.8 (3)	C16—C17—H17B	109.6
F1—C7—C6	118.6 (3)	H17A—C17—H17B	108.2
C7—C8—C9	120.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2v	0.861 (10)	2.48 (4)	3.184 (4)	139 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2i	0.861 (10)	2.48 (4)	3.184 (4)	139 (5)

Symmetry code: (i) .