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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): m248.
Published online 2009 February 4. doi:  10.1107/S1600536809003584
PMCID: PMC2968697

Bis[1-ethyl-6-fluoro-7-(4-methyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ato-κ2 O 3,O 4]­copper(II)

Abstract

In the title compound, [Cu(C17H19FN3O3)2], the CuII atom (site symmetry An external file that holds a picture, illustration, etc.
Object name is e-65-0m248-efi1.jpg) exhibits a slightly distorted CuO4 square-planar geometry defined by two bidentate O,O′-bonded 1-ethyl-6-fluoro-7-(4-methyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ate (perfloxacinate) anions.

Related literature

For the silver, manganese, cobalt and zinc complexes of the perfloxacinate (pef) anion, see: Baenziger et al. (1986 [triangle]); An, Huang & Qi (2007 [triangle]); An, Qi & Huang (2007 [triangle]); Qi et al.(2008 [triangle]), respectively. For background on the medicinal uses of Hpef, see: Mizuki et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m248-scheme1.jpg

Experimental

Crystal data

  • [Cu(C17H19FN3O3)2]
  • M r = 728.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m248-efi2.jpg
  • a = 8.5548 (17) Å
  • b = 10.253 (2) Å
  • c = 10.467 (2) Å
  • α = 95.22 (3)°
  • β = 109.63 (3)°
  • γ = 108.01 (3)°
  • V = 802.7 (4) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.75 mm−1
  • T = 296 (2) K
  • 0.36 × 0.28 × 0.19 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.774, T max = 0.871
  • 7880 measured reflections
  • 3633 independent reflections
  • 3274 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.103
  • S = 1.14
  • 3633 reflections
  • 225 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.37 e Å−3

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

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003584/hb2904sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003584/hb2904Isup2.hkl

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

Acknowledgments

The authors thank the Scientific Research Fund of Heilongjiang Provincial Education Department (grant No. 11531115) and the Graduate Creativity Funds of Harbin Medical University (HCXS) (grant No. 2008008) for financial support.

supplementary crystallographic information

Comment

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), cobalt(II) and zinc(II) derivative of the pefloxacinate (pef) anion has been reported (Baenziger et al.,1986; An, Huang & Qi (2007); An, Qi & Huang (2007); Qi et al.(2008); Qi et al., 2008). The title copper(II)-containing complex of pef, (I), is reported here.

The structure of (I) is built up from Cu2+ cations (site symmetry 1) anions (pef) ligands, (Fig. 1). It is confirmed that four coordinating O atoms arround CuII cation form a square planar configuration. (Table 1).

Experimental

A mixture of Cu(CH3COO)2.H2O (0.050 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 433 K for 72 h under autogenous pressure. Upon cooling, blue prisms of (I) were obtained from the reaction mixture.

Refinement

All H atoms on C atoms were generated geometrically and refined as riding atoms with C—H= 0.93–0.97Å and Uiso(H)= 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I), show the Cu coordination, showing 50% displacement ellipsoids (arbitrary spheres for the H atoms). [Symmetry code: (i) 1–x, 1–y, 1–z.]

Crystal data

[Cu(C17H19FN3O3)2]Z = 1
Mr = 728.24F(000) = 379
Triclinic, P1Dx = 1.506 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5548 (17) ÅCell parameters from 7808 reflections
b = 10.253 (2) Åθ = 3.1–27.5°
c = 10.467 (2) ŵ = 0.75 mm1
α = 95.22 (3)°T = 296 K
β = 109.63 (3)°Prism, blue
γ = 108.01 (3)°0.36 × 0.28 × 0.19 mm
V = 802.7 (4) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3633 independent reflections
Radiation source: fine-focus sealed tube3274 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 0 pixels mm-1θmax = 27.5°, θmin = 3.1°
[var phi] and ω scansh = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2001)k = −10→13
Tmin = 0.774, Tmax = 0.871l = −13→13
7880 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.06P)2 + 0.1742P] where P = (Fo2 + 2Fc2)/3
3633 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.37 e Å3

Special details

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)

xyzUiso*/Ueq
Cu10.50000.50000.50000.02371 (11)
F10.82563 (18)0.16415 (13)0.12581 (17)0.0524 (4)
O10.59169 (18)0.69304 (14)0.50180 (16)0.0337 (3)
O20.7906 (2)0.89436 (16)0.5126 (2)0.0579 (5)
O30.63511 (17)0.45479 (13)0.39993 (15)0.0302 (3)
N11.09849 (19)0.72064 (15)0.39047 (16)0.0239 (3)
N21.1346 (2)0.33064 (16)0.10980 (17)0.0291 (3)
N31.3578 (2)0.24538 (19)−0.00270 (19)0.0353 (4)
C10.7358 (3)0.76677 (19)0.4892 (2)0.0294 (4)
C20.8370 (2)0.69045 (18)0.44045 (19)0.0244 (4)
C30.7735 (2)0.54329 (18)0.39289 (18)0.0231 (3)
C40.8738 (2)0.49016 (18)0.32802 (19)0.0233 (3)
C50.8070 (2)0.34754 (19)0.2611 (2)0.0297 (4)
H5A0.70140.28640.26170.036*
C60.8976 (3)0.30001 (19)0.1959 (2)0.0315 (4)
C71.0598 (2)0.38636 (19)0.1906 (2)0.0267 (4)
C81.1264 (2)0.52630 (19)0.2581 (2)0.0258 (4)
H8A1.23360.58610.25870.031*
C91.0346 (2)0.57967 (18)0.32596 (18)0.0227 (3)
C100.9982 (2)0.77176 (18)0.43938 (19)0.0254 (4)
H10A1.04000.86800.47480.031*
C111.2746 (2)0.81963 (19)0.4025 (2)0.0307 (4)
H11A1.35930.77210.42290.037*
H11B1.31710.89850.47970.037*
C121.2671 (3)0.8743 (2)0.2716 (3)0.0470 (6)
H12A1.22530.79670.19480.071*
H12B1.38390.93580.28400.071*
H12C1.18730.92490.25300.071*
C131.2615 (3)0.4313 (2)0.0678 (2)0.0326 (4)
H13A1.37460.47600.14590.039*
H13B1.21650.50360.03660.039*
C141.2866 (3)0.3524 (2)−0.0493 (2)0.0333 (4)
H14A1.17320.3084−0.12720.040*
H14B1.36770.4179−0.08030.040*
C151.2292 (3)0.1448 (2)0.0361 (2)0.0352 (4)
H15A1.27320.07160.06570.042*
H15B1.11780.1013−0.04390.042*
C161.1970 (3)0.2168 (2)0.1528 (2)0.0332 (4)
H16A1.10850.14900.17570.040*
H16B1.30650.25510.23490.040*
C171.3936 (4)0.1748 (3)−0.1120 (3)0.0563 (7)
H17A1.44810.1096−0.07680.084*
H17B1.47240.2435−0.14070.084*
H17C1.28380.1252−0.19000.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu10.02365 (17)0.02145 (17)0.03097 (19)0.00834 (12)0.01668 (13)0.00415 (12)
F10.0481 (7)0.0230 (6)0.0834 (10)−0.0009 (5)0.0416 (7)−0.0160 (6)
O10.0325 (7)0.0262 (7)0.0559 (9)0.0138 (5)0.0299 (7)0.0110 (6)
O20.0654 (11)0.0217 (7)0.1127 (16)0.0147 (7)0.0680 (12)0.0092 (9)
O30.0283 (6)0.0214 (6)0.0445 (8)0.0039 (5)0.0246 (6)0.0008 (6)
N10.0220 (7)0.0178 (7)0.0334 (8)0.0060 (5)0.0139 (6)0.0034 (6)
N20.0363 (8)0.0222 (8)0.0393 (9)0.0123 (6)0.0254 (7)0.0066 (7)
N30.0379 (9)0.0391 (10)0.0392 (10)0.0191 (7)0.0234 (8)0.0049 (8)
C10.0347 (9)0.0217 (9)0.0419 (11)0.0126 (7)0.0242 (8)0.0078 (8)
C20.0278 (8)0.0210 (8)0.0297 (9)0.0104 (7)0.0162 (7)0.0049 (7)
C30.0244 (8)0.0214 (8)0.0263 (9)0.0083 (6)0.0131 (7)0.0053 (7)
C40.0248 (8)0.0192 (8)0.0292 (9)0.0077 (6)0.0147 (7)0.0048 (7)
C50.0291 (9)0.0207 (9)0.0405 (11)0.0047 (7)0.0200 (8)0.0020 (8)
C60.0329 (9)0.0179 (8)0.0440 (11)0.0041 (7)0.0218 (8)−0.0016 (8)
C70.0295 (9)0.0224 (9)0.0329 (9)0.0102 (7)0.0177 (8)0.0037 (7)
C80.0247 (8)0.0219 (8)0.0345 (9)0.0083 (6)0.0162 (7)0.0056 (7)
C90.0246 (8)0.0185 (8)0.0271 (9)0.0088 (6)0.0119 (7)0.0041 (7)
C100.0287 (8)0.0179 (8)0.0319 (9)0.0086 (7)0.0148 (7)0.0027 (7)
C110.0219 (8)0.0205 (8)0.0489 (12)0.0038 (6)0.0178 (8)0.0007 (8)
C120.0486 (12)0.0361 (12)0.0679 (16)0.0106 (10)0.0388 (12)0.0182 (11)
C130.0386 (10)0.0251 (9)0.0428 (11)0.0110 (8)0.0265 (9)0.0077 (8)
C140.0374 (10)0.0336 (10)0.0347 (10)0.0115 (8)0.0220 (8)0.0069 (8)
C150.0459 (11)0.0307 (10)0.0407 (11)0.0203 (9)0.0249 (9)0.0079 (8)
C160.0454 (11)0.0308 (10)0.0370 (11)0.0198 (8)0.0258 (9)0.0100 (8)
C170.0764 (18)0.0512 (15)0.0686 (17)0.0307 (13)0.0547 (15)0.0096 (13)

Geometric parameters (Å, °)

Cu1—O1i1.8858 (15)C6—C71.419 (3)
Cu1—O11.8858 (15)C7—C81.387 (3)
Cu1—O31.9247 (13)C8—C91.411 (2)
Cu1—O3i1.9247 (13)C8—H8A0.9300
F1—C61.356 (2)C10—H10A0.9300
O1—C11.288 (2)C11—C121.517 (3)
O2—C11.215 (2)C11—H11A0.9700
O3—C31.279 (2)C11—H11B0.9700
N1—C101.341 (2)C12—H12A0.9600
N1—C91.389 (2)C12—H12B0.9600
N1—C111.490 (2)C12—H12C0.9600
N2—C71.397 (2)C13—C141.517 (3)
N2—C131.465 (2)C13—H13A0.9700
N2—C161.473 (2)C13—H13B0.9700
N3—C151.454 (3)C14—H14A0.9700
N3—C141.458 (3)C14—H14B0.9700
N3—C171.465 (3)C15—C161.516 (3)
C1—C21.505 (2)C15—H15A0.9700
C2—C101.378 (2)C15—H15B0.9700
C2—C31.412 (2)C16—H16A0.9700
C3—C41.451 (2)C16—H16B0.9700
C4—C91.406 (2)C17—H17A0.9600
C4—C51.408 (3)C17—H17B0.9600
C5—C61.354 (3)C17—H17C0.9600
C5—H5A0.9300
O1i—Cu1—O1180.0N1—C10—H10A118.0
O1i—Cu1—O387.35 (6)C2—C10—H10A118.0
O1—Cu1—O392.65 (6)N1—C11—C12112.76 (17)
O1i—Cu1—O3i92.65 (6)N1—C11—H11A109.0
O1—Cu1—O3i87.35 (6)C12—C11—H11A109.0
O3—Cu1—O3i180.0N1—C11—H11B109.0
C1—O1—Cu1130.33 (12)C12—C11—H11B109.0
C3—O3—Cu1124.62 (12)H11A—C11—H11B107.8
C10—N1—C9119.95 (15)C11—C12—H12A109.5
C10—N1—C11118.31 (15)C11—C12—H12B109.5
C9—N1—C11121.70 (14)H12A—C12—H12B109.5
C7—N2—C13116.83 (15)C11—C12—H12C109.5
C7—N2—C16117.25 (15)H12A—C12—H12C109.5
C13—N2—C16111.04 (15)H12B—C12—H12C109.5
C15—N3—C14108.25 (16)N2—C13—C14108.39 (16)
C15—N3—C17110.58 (18)N2—C13—H13A110.0
C14—N3—C17110.99 (18)C14—C13—H13A110.0
O2—C1—O1122.66 (17)N2—C13—H13B110.0
O2—C1—C2119.20 (17)C14—C13—H13B110.0
O1—C1—C2118.13 (16)H13A—C13—H13B108.4
C10—C2—C3119.32 (16)N3—C14—C13110.51 (17)
C10—C2—C1116.81 (15)N3—C14—H14A109.5
C3—C2—C1123.84 (16)C13—C14—H14A109.5
O3—C3—C2125.72 (16)N3—C14—H14B109.5
O3—C3—C4118.07 (15)C13—C14—H14B109.5
C2—C3—C4116.19 (15)H14A—C14—H14B108.1
C9—C4—C5118.77 (16)N3—C15—C16110.62 (17)
C9—C4—C3121.23 (16)N3—C15—H15A109.5
C5—C4—C3119.96 (16)C16—C15—H15A109.5
C6—C5—C4119.63 (17)N3—C15—H15B109.5
C6—C5—H5A120.2C16—C15—H15B109.5
C4—C5—H5A120.2H15A—C15—H15B108.1
C5—C6—F1118.45 (17)N2—C16—C15109.86 (16)
C5—C6—C7123.62 (17)N2—C16—H16A109.7
F1—C6—C7117.85 (16)C15—C16—H16A109.7
C8—C7—N2123.85 (16)N2—C16—H16B109.7
C8—C7—C6116.62 (16)C15—C16—H16B109.7
N2—C7—C6119.30 (16)H16A—C16—H16B108.2
C7—C8—C9121.24 (16)N3—C17—H17A109.5
C7—C8—H8A119.4N3—C17—H17B109.5
C9—C8—H8A119.4H17A—C17—H17B109.5
N1—C9—C4118.52 (15)N3—C17—H17C109.5
N1—C9—C8121.36 (15)H17A—C17—H17C109.5
C4—C9—C8120.11 (16)H17B—C17—H17C109.5
N1—C10—C2124.01 (16)
O3—Cu1—O1—C1−22.51 (19)C5—C6—C7—N2−174.06 (19)
O3i—Cu1—O1—C1157.49 (19)F1—C6—C7—N22.6 (3)
O1i—Cu1—O3—C3−160.14 (16)N2—C7—C8—C9173.18 (17)
O1—Cu1—O3—C319.86 (16)C6—C7—C8—C9−1.2 (3)
Cu1—O1—C1—O2−168.97 (18)C10—N1—C9—C4−7.3 (3)
Cu1—O1—C1—C212.5 (3)C11—N1—C9—C4175.07 (17)
O2—C1—C2—C106.8 (3)C10—N1—C9—C8171.97 (17)
O1—C1—C2—C10−174.60 (18)C11—N1—C9—C8−5.6 (3)
O2—C1—C2—C3−171.3 (2)C5—C4—C9—N1179.12 (17)
O1—C1—C2—C37.3 (3)C3—C4—C9—N11.4 (3)
Cu1—O3—C3—C2−8.9 (3)C5—C4—C9—C8−0.2 (3)
Cu1—O3—C3—C4172.47 (12)C3—C4—C9—C8−177.85 (16)
C10—C2—C3—O3173.24 (17)C7—C8—C9—N1−178.24 (17)
C1—C2—C3—O3−8.7 (3)C7—C8—C9—C41.0 (3)
C10—C2—C3—C4−8.1 (3)C9—N1—C10—C25.5 (3)
C1—C2—C3—C4169.88 (17)C11—N1—C10—C2−176.84 (18)
O3—C3—C4—C9−175.10 (16)C3—C2—C10—N12.7 (3)
C2—C3—C4—C96.2 (3)C1—C2—C10—N1−175.49 (17)
O3—C3—C4—C57.3 (3)C10—N1—C11—C12−95.8 (2)
C2—C3—C4—C5−171.48 (17)C9—N1—C11—C1281.9 (2)
C9—C4—C5—C6−0.4 (3)C7—N2—C13—C14−164.32 (17)
C3—C4—C5—C6177.27 (18)C16—N2—C13—C1457.6 (2)
C4—C5—C6—F1−176.44 (19)C15—N3—C14—C1362.2 (2)
C4—C5—C6—C70.2 (3)C17—N3—C14—C13−176.26 (18)
C13—N2—C7—C8−15.2 (3)N2—C13—C14—N3−60.8 (2)
C16—N2—C7—C8120.3 (2)C14—N3—C15—C16−60.3 (2)
C13—N2—C7—C6159.03 (19)C17—N3—C15—C16178.0 (2)
C16—N2—C7—C6−65.5 (2)C7—N2—C16—C15165.57 (17)
C5—C6—C7—C80.6 (3)C13—N2—C16—C15−56.5 (2)
F1—C6—C7—C8177.28 (18)N3—C15—C16—N257.7 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2904).

References

  • An, Z., Huang, J. & Qi, W. (2007). Acta Cryst. E63, m2009.
  • An, Z., Qi, W. & Huang, J. (2007). Acta Cryst. E63, m2084–m2085.
  • Baenziger, N. C., Fox, C. L. & Modak, S. L. (1986). Acta Cryst. C42, 1505–1509.
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother.37 (Suppl. A), 41–45. [PubMed]
  • Qi, W., Huang, J. & An, Z. (2008). Acta Cryst. E64, m302. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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