Bis[1-ethyl-6-fluoro-7-(4-methyl­piperazin-1-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ato-κ2O3,O4]­copper(II)

Qi, W.; Gao, J.; Liang, D.; An, Z.

doi:10.1107/S1600536809003584

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m248

doi:10.1107/S1600536809003584

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Bis[1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-κ²O³,O⁴]copper(II)

Wei Qi,^a Jing Gao,^b Di Liang ^a and Zhe An ^a ^*

^aSchool of Pharmaceutical Science, Harbin Medical University, Harbin 150086, People's Republic of China, and ^bDepartment of Pharmacy, Mudanjiang Medical University, Mudanjiang 157011, People's Republic of China
^*Correspondence e-mail: anzhe6409@sina.com

(Received 24 January 2009; accepted 29 January 2009; online 4 February 2009)

In the title compound, [Cu(C₁₇H₁₉FN₃O₃)₂], the Cu^II atom (site symmetry $[\overline{1}]$ ) 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 ); An, Huang & Qi (2007 ); An, Qi & Huang (2007 ); Qi et al.(2008 ), respectively. For background on the medicinal uses of Hpef, see: Mizuki et al. (1996 ).

Experimental

Crystal data

[Cu(C₁₇H₁₉FN₃O₃)₂]
M_r = 728.24
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.103
S = 1.14
3633 reflections
225 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O1	1.8858 (15)
Cu1—O3	1.9247 (13)

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

Supporting information

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

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003584/hb2904Isup2.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), 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 Cu^II cation form a square planar configuration. (Table 1).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

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.]

Bis[1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline- 3-carboxylato-κ²O³,O⁴]copper(II) top

Crystal data top

[Cu(C₁₇H₁₉FN₃O₃)₂]	Z = 1
M_r = 728.24	F(000) = 379
Triclinic, P1	D_x = 1.506 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5548 (17) Å	Cell parameters from 7808 reflections
b = 10.253 (2) Å	θ = 3.1–27.5°
c = 10.467 (2) Å	µ = 0.75 mm⁻¹
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 top

Bruker SMART CCD area-detector diffractometer	3633 independent reflections
Radiation source: fine-focus sealed tube	3274 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −10→13
T_min = 0.774, T_max = 0.871	l = −13→13
7880 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.06P)² + 0.1742P] where P = (F_o² + 2F_c²)/3
3633 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Cu(C₁₇H₁₉FN₃O₃)₂]	γ = 108.01 (3)°
M_r = 728.24	V = 802.7 (4) Å³
Triclinic, P1	Z = 1
a = 8.5548 (17) Å	Mo Kα radiation
b = 10.253 (2) Å	µ = 0.75 mm⁻¹
c = 10.467 (2) Å	T = 296 K
α = 95.22 (3)°	0.36 × 0.28 × 0.19 mm
β = 109.63 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3633 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3274 reflections with I > 2σ(I)
T_min = 0.774, T_max = 0.871	R_int = 0.022
7880 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.14	Δρ_max = 0.35 e Å⁻³
3633 reflections	Δρ_min = −0.37 e Å⁻³
225 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
Cu1	0.5000	0.5000	0.5000	0.02371 (11)
F1	0.82563 (18)	0.16415 (13)	0.12581 (17)	0.0524 (4)
O1	0.59169 (18)	0.69304 (14)	0.50180 (16)	0.0337 (3)
O2	0.7906 (2)	0.89436 (16)	0.5126 (2)	0.0579 (5)
O3	0.63511 (17)	0.45479 (13)	0.39993 (15)	0.0302 (3)
N1	1.09849 (19)	0.72064 (15)	0.39047 (16)	0.0239 (3)
N2	1.1346 (2)	0.33064 (16)	0.10980 (17)	0.0291 (3)
N3	1.3578 (2)	0.24538 (19)	−0.00270 (19)	0.0353 (4)
C1	0.7358 (3)	0.76677 (19)	0.4892 (2)	0.0294 (4)
C2	0.8370 (2)	0.69045 (18)	0.44045 (19)	0.0244 (4)
C3	0.7735 (2)	0.54329 (18)	0.39289 (18)	0.0231 (3)
C4	0.8738 (2)	0.49016 (18)	0.32802 (19)	0.0233 (3)
C5	0.8070 (2)	0.34754 (19)	0.2611 (2)	0.0297 (4)
H5A	0.7014	0.2864	0.2617	0.036*
C6	0.8976 (3)	0.30001 (19)	0.1959 (2)	0.0315 (4)
C7	1.0598 (2)	0.38636 (19)	0.1906 (2)	0.0267 (4)
C8	1.1264 (2)	0.52630 (19)	0.2581 (2)	0.0258 (4)
H8A	1.2336	0.5861	0.2587	0.031*
C9	1.0346 (2)	0.57967 (18)	0.32596 (18)	0.0227 (3)
C10	0.9982 (2)	0.77176 (18)	0.43938 (19)	0.0254 (4)
H10A	1.0400	0.8680	0.4748	0.031*
C11	1.2746 (2)	0.81963 (19)	0.4025 (2)	0.0307 (4)
H11A	1.3593	0.7721	0.4229	0.037*
H11B	1.3171	0.8985	0.4797	0.037*
C12	1.2671 (3)	0.8743 (2)	0.2716 (3)	0.0470 (6)
H12A	1.2253	0.7967	0.1948	0.071*
H12B	1.3839	0.9358	0.2840	0.071*
H12C	1.1873	0.9249	0.2530	0.071*
C13	1.2615 (3)	0.4313 (2)	0.0678 (2)	0.0326 (4)
H13A	1.3746	0.4760	0.1459	0.039*
H13B	1.2165	0.5036	0.0366	0.039*
C14	1.2866 (3)	0.3524 (2)	−0.0493 (2)	0.0333 (4)
H14A	1.1732	0.3084	−0.1272	0.040*
H14B	1.3677	0.4179	−0.0803	0.040*
C15	1.2292 (3)	0.1448 (2)	0.0361 (2)	0.0352 (4)
H15A	1.2732	0.0716	0.0657	0.042*
H15B	1.1178	0.1013	−0.0439	0.042*
C16	1.1970 (3)	0.2168 (2)	0.1528 (2)	0.0332 (4)
H16A	1.1085	0.1490	0.1757	0.040*
H16B	1.3065	0.2551	0.2349	0.040*
C17	1.3936 (4)	0.1748 (3)	−0.1120 (3)	0.0563 (7)
H17A	1.4481	0.1096	−0.0768	0.084*
H17B	1.4724	0.2435	−0.1407	0.084*
H17C	1.2838	0.1252	−0.1900	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02365 (17)	0.02145 (17)	0.03097 (19)	0.00834 (12)	0.01668 (13)	0.00415 (12)
F1	0.0481 (7)	0.0230 (6)	0.0834 (10)	−0.0009 (5)	0.0416 (7)	−0.0160 (6)
O1	0.0325 (7)	0.0262 (7)	0.0559 (9)	0.0138 (5)	0.0299 (7)	0.0110 (6)
O2	0.0654 (11)	0.0217 (7)	0.1127 (16)	0.0147 (7)	0.0680 (12)	0.0092 (9)
O3	0.0283 (6)	0.0214 (6)	0.0445 (8)	0.0039 (5)	0.0246 (6)	0.0008 (6)
N1	0.0220 (7)	0.0178 (7)	0.0334 (8)	0.0060 (5)	0.0139 (6)	0.0034 (6)
N2	0.0363 (8)	0.0222 (8)	0.0393 (9)	0.0123 (6)	0.0254 (7)	0.0066 (7)
N3	0.0379 (9)	0.0391 (10)	0.0392 (10)	0.0191 (7)	0.0234 (8)	0.0049 (8)
C1	0.0347 (9)	0.0217 (9)	0.0419 (11)	0.0126 (7)	0.0242 (8)	0.0078 (8)
C2	0.0278 (8)	0.0210 (8)	0.0297 (9)	0.0104 (7)	0.0162 (7)	0.0049 (7)
C3	0.0244 (8)	0.0214 (8)	0.0263 (9)	0.0083 (6)	0.0131 (7)	0.0053 (7)
C4	0.0248 (8)	0.0192 (8)	0.0292 (9)	0.0077 (6)	0.0147 (7)	0.0048 (7)
C5	0.0291 (9)	0.0207 (9)	0.0405 (11)	0.0047 (7)	0.0200 (8)	0.0020 (8)
C6	0.0329 (9)	0.0179 (8)	0.0440 (11)	0.0041 (7)	0.0218 (8)	−0.0016 (8)
C7	0.0295 (9)	0.0224 (9)	0.0329 (9)	0.0102 (7)	0.0177 (8)	0.0037 (7)
C8	0.0247 (8)	0.0219 (8)	0.0345 (9)	0.0083 (6)	0.0162 (7)	0.0056 (7)
C9	0.0246 (8)	0.0185 (8)	0.0271 (9)	0.0088 (6)	0.0119 (7)	0.0041 (7)
C10	0.0287 (8)	0.0179 (8)	0.0319 (9)	0.0086 (7)	0.0148 (7)	0.0027 (7)
C11	0.0219 (8)	0.0205 (8)	0.0489 (12)	0.0038 (6)	0.0178 (8)	0.0007 (8)
C12	0.0486 (12)	0.0361 (12)	0.0679 (16)	0.0106 (10)	0.0388 (12)	0.0182 (11)
C13	0.0386 (10)	0.0251 (9)	0.0428 (11)	0.0110 (8)	0.0265 (9)	0.0077 (8)
C14	0.0374 (10)	0.0336 (10)	0.0347 (10)	0.0115 (8)	0.0220 (8)	0.0069 (8)
C15	0.0459 (11)	0.0307 (10)	0.0407 (11)	0.0203 (9)	0.0249 (9)	0.0079 (8)
C16	0.0454 (11)	0.0308 (10)	0.0370 (11)	0.0198 (8)	0.0258 (9)	0.0100 (8)
C17	0.0764 (18)	0.0512 (15)	0.0686 (17)	0.0307 (13)	0.0547 (15)	0.0096 (13)

Geometric parameters (Å, º) top

Cu1—O1ⁱ	1.8858 (15)	C6—C7	1.419 (3)
Cu1—O1	1.8858 (15)	C7—C8	1.387 (3)
Cu1—O3	1.9247 (13)	C8—C9	1.411 (2)
Cu1—O3ⁱ	1.9247 (13)	C8—H8A	0.9300
F1—C6	1.356 (2)	C10—H10A	0.9300
O1—C1	1.288 (2)	C11—C12	1.517 (3)
O2—C1	1.215 (2)	C11—H11A	0.9700
O3—C3	1.279 (2)	C11—H11B	0.9700
N1—C10	1.341 (2)	C12—H12A	0.9600
N1—C9	1.389 (2)	C12—H12B	0.9600
N1—C11	1.490 (2)	C12—H12C	0.9600
N2—C7	1.397 (2)	C13—C14	1.517 (3)
N2—C13	1.465 (2)	C13—H13A	0.9700
N2—C16	1.473 (2)	C13—H13B	0.9700
N3—C15	1.454 (3)	C14—H14A	0.9700
N3—C14	1.458 (3)	C14—H14B	0.9700
N3—C17	1.465 (3)	C15—C16	1.516 (3)
C1—C2	1.505 (2)	C15—H15A	0.9700
C2—C10	1.378 (2)	C15—H15B	0.9700
C2—C3	1.412 (2)	C16—H16A	0.9700
C3—C4	1.451 (2)	C16—H16B	0.9700
C4—C9	1.406 (2)	C17—H17A	0.9600
C4—C5	1.408 (3)	C17—H17B	0.9600
C5—C6	1.354 (3)	C17—H17C	0.9600
C5—H5A	0.9300

O1ⁱ—Cu1—O1	180.0	N1—C10—H10A	118.0
O1ⁱ—Cu1—O3	87.35 (6)	C2—C10—H10A	118.0
O1—Cu1—O3	92.65 (6)	N1—C11—C12	112.76 (17)
O1ⁱ—Cu1—O3ⁱ	92.65 (6)	N1—C11—H11A	109.0
O1—Cu1—O3ⁱ	87.35 (6)	C12—C11—H11A	109.0
O3—Cu1—O3ⁱ	180.0	N1—C11—H11B	109.0
C1—O1—Cu1	130.33 (12)	C12—C11—H11B	109.0
C3—O3—Cu1	124.62 (12)	H11A—C11—H11B	107.8
C10—N1—C9	119.95 (15)	C11—C12—H12A	109.5
C10—N1—C11	118.31 (15)	C11—C12—H12B	109.5
C9—N1—C11	121.70 (14)	H12A—C12—H12B	109.5
C7—N2—C13	116.83 (15)	C11—C12—H12C	109.5
C7—N2—C16	117.25 (15)	H12A—C12—H12C	109.5
C13—N2—C16	111.04 (15)	H12B—C12—H12C	109.5
C15—N3—C14	108.25 (16)	N2—C13—C14	108.39 (16)
C15—N3—C17	110.58 (18)	N2—C13—H13A	110.0
C14—N3—C17	110.99 (18)	C14—C13—H13A	110.0
O2—C1—O1	122.66 (17)	N2—C13—H13B	110.0
O2—C1—C2	119.20 (17)	C14—C13—H13B	110.0
O1—C1—C2	118.13 (16)	H13A—C13—H13B	108.4
C10—C2—C3	119.32 (16)	N3—C14—C13	110.51 (17)
C10—C2—C1	116.81 (15)	N3—C14—H14A	109.5
C3—C2—C1	123.84 (16)	C13—C14—H14A	109.5
O3—C3—C2	125.72 (16)	N3—C14—H14B	109.5
O3—C3—C4	118.07 (15)	C13—C14—H14B	109.5
C2—C3—C4	116.19 (15)	H14A—C14—H14B	108.1
C9—C4—C5	118.77 (16)	N3—C15—C16	110.62 (17)
C9—C4—C3	121.23 (16)	N3—C15—H15A	109.5
C5—C4—C3	119.96 (16)	C16—C15—H15A	109.5
C6—C5—C4	119.63 (17)	N3—C15—H15B	109.5
C6—C5—H5A	120.2	C16—C15—H15B	109.5
C4—C5—H5A	120.2	H15A—C15—H15B	108.1
C5—C6—F1	118.45 (17)	N2—C16—C15	109.86 (16)
C5—C6—C7	123.62 (17)	N2—C16—H16A	109.7
F1—C6—C7	117.85 (16)	C15—C16—H16A	109.7
C8—C7—N2	123.85 (16)	N2—C16—H16B	109.7
C8—C7—C6	116.62 (16)	C15—C16—H16B	109.7
N2—C7—C6	119.30 (16)	H16A—C16—H16B	108.2
C7—C8—C9	121.24 (16)	N3—C17—H17A	109.5
C7—C8—H8A	119.4	N3—C17—H17B	109.5
C9—C8—H8A	119.4	H17A—C17—H17B	109.5
N1—C9—C4	118.52 (15)	N3—C17—H17C	109.5
N1—C9—C8	121.36 (15)	H17A—C17—H17C	109.5
C4—C9—C8	120.11 (16)	H17B—C17—H17C	109.5
N1—C10—C2	124.01 (16)

O3—Cu1—O1—C1	−22.51 (19)	C5—C6—C7—N2	−174.06 (19)
O3ⁱ—Cu1—O1—C1	157.49 (19)	F1—C6—C7—N2	2.6 (3)
O1ⁱ—Cu1—O3—C3	−160.14 (16)	N2—C7—C8—C9	173.18 (17)
O1—Cu1—O3—C3	19.86 (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—C2	12.5 (3)	C11—N1—C9—C4	175.07 (17)
O2—C1—C2—C10	6.8 (3)	C10—N1—C9—C8	171.97 (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—N1	179.12 (17)
O1—C1—C2—C3	7.3 (3)	C3—C4—C9—N1	1.4 (3)
Cu1—O3—C3—C2	−8.9 (3)	C5—C4—C9—C8	−0.2 (3)
Cu1—O3—C3—C4	172.47 (12)	C3—C4—C9—C8	−177.85 (16)
C10—C2—C3—O3	173.24 (17)	C7—C8—C9—N1	−178.24 (17)
C1—C2—C3—O3	−8.7 (3)	C7—C8—C9—C4	1.0 (3)
C10—C2—C3—C4	−8.1 (3)	C9—N1—C10—C2	5.5 (3)
C1—C2—C3—C4	169.88 (17)	C11—N1—C10—C2	−176.84 (18)
O3—C3—C4—C9	−175.10 (16)	C3—C2—C10—N1	2.7 (3)
C2—C3—C4—C9	6.2 (3)	C1—C2—C10—N1	−175.49 (17)
O3—C3—C4—C5	7.3 (3)	C10—N1—C11—C12	−95.8 (2)
C2—C3—C4—C5	−171.48 (17)	C9—N1—C11—C12	81.9 (2)
C9—C4—C5—C6	−0.4 (3)	C7—N2—C13—C14	−164.32 (17)
C3—C4—C5—C6	177.27 (18)	C16—N2—C13—C14	57.6 (2)
C4—C5—C6—F1	−176.44 (19)	C15—N3—C14—C13	62.2 (2)
C4—C5—C6—C7	0.2 (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—C8	120.3 (2)	C14—N3—C15—C16	−60.3 (2)
C13—N2—C7—C6	159.03 (19)	C17—N3—C15—C16	178.0 (2)
C16—N2—C7—C6	−65.5 (2)	C7—N2—C16—C15	165.57 (17)
C5—C6—C7—C8	0.6 (3)	C13—N2—C16—C15	−56.5 (2)
F1—C6—C7—C8	177.28 (18)	N3—C15—C16—N2	57.7 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₉FN₃O₃)₂]
M_r	728.24
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.5548 (17), 10.253 (2), 10.467 (2)
α, β, γ (°)	95.22 (3), 109.63 (3), 108.01 (3)
V (Å³)	802.7 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.36 × 0.28 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.774, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	7880, 3633, 3274
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.103, 1.14
No. of reflections	3633
No. of parameters	225
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.37

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

Selected bond lengths (Å) top

Cu1—O1

1.8858 (15)

Cu1—O3

1.9247 (13)

Acknowledgements

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.

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 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 (Suppl. A), 41–45. Google Scholar
Qi, W., Huang, J. & An, Z. (2008). Acta Cryst. E64, m302. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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