Bis[μ-2-(2,4-difluoro­phen­yl)-1,3-bis­(1H-1,2,4-triazol-1-yl)propan-2-olato]dicopper(II) bis­(perchlorate)

Luo, Z.-R.; Hu, F.-L.; Zhuang, Y.; Yin, X.-H.; Wu, Q.-L.

doi:10.1107/S1600536810008512

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m391

doi:10.1107/S1600536810008512

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Bis[μ-2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-olato]dicopper(II) bis(perchlorate)

Zhi-Rong Luo,^a Fei-Long Hu,^a Yue Zhuang,^a Xian-Hong Yin ^a ^* and Qiao-Lan Wu ^a

^aDepartment of Chemistry, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: yxhphd@163.com

(Received 23 October 2009; accepted 5 March 2010; online 10 March 2010)

The title complex, [Cu₂(C₁₃H₁₁F₂N₆O)₂](ClO₄)₂, which was hydrothermally synthesized, contains a binuclear copper cluster (2 symmetry) with a Cu₂O₂ rhombus [Cu—O = 1.927 (2) Å] formed by donation of two O atoms from two chelate rings. The tridentate function of each ligand is completed by two N atoms coordinated to the two Cu^II atoms [Cu—N = 1.933 (2) Å]. The separation distance of two Cu^II atoms in a cluster is 2.988 (1) Å. The dihedral angle between the six-membered chelate rings is 2.13 (9)°. The perchlorate counter-anion is disordered over two sites in a 0.58 (10):0.42 (10) ratio.

Related literature

For the use of 1,2,4-triazole and its derivatives in coordination chemistry, see: Haasnoot et al. (2000 ); Zhao et al. (2007 ). For 1,2,4-triazole as a bridging ligand, see: Liu et al. (2003 ); Park et al. (2006 ); Yi et al. (2004 ); Garcia et al. (2005 ).

Experimental

Crystal data

[Cu₂(C₁₃H₁₁F₂N₆O)₂](ClO₄)₂
M_r = 936.54
Orthorhombic, P n n m
a = 15.4464 (18) Å
b = 7.9532 (10) Å
c = 14.2407 (15) Å
V = 1749.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 298 K
0.49 × 0.45 × 0.43 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.534, T_max = 0.572
7867 measured reflections
1618 independent reflections
1169 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.129
S = 1.09
1618 reflections
162 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536810008512/kp2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810008512/kp2237Isup2.hkl

checkCIF report

Comment top

1,2,4-triazole and its derivatives, being used in pharmaceuticals and agricultural chemicals, have attracted ever-increasing attention in coordination chemistry (Haasnoot et al., 2000, Zhao et al., 2007). The coordination versatility of 1, 2, 4-triazole as a reliable bridging ligand, i.e. adopting diverse binding fashions upon metal complexation, will be responsible for structural diversity of the resulting coordination frameworks (Liu et al., 2003, Park et al., 2006, Yi et al., 2004, Garcia et al., 2005). Now, we present the synthesis and structure analysis of the title Hflu complex derived from bis-fluconazolato-di-copper diperchlorate. The distinct binding modes of the ligands (Scheme 1) and the coordination preferences of the metal ion are discussed. The title binuclear copper(II) compound, C₂₆H₂₂Cl₂Cu₂F₄N₁₂O₁₀, reveals a centro-symmetric arrangement. The coordination of Cu1 is achieved by 1, 2, 4-triazole-N and flu-O ligands (Fig. 1); two oxygen atoms of fluconazole molecule form rhombus with two copper atoms with Cu-O1 bond of 1.927 (2) Å, forming a Z-style structure. The perchlorate ion is not coordinated to Cu^II atom. It take a part in formation of an ornament of 'palace lantern-style'geometry (Fig. 2). The perchlorate anions adopt two crystallographic orientations in the crystal lattice with occupancy factors of 0.576 and 0.424. The dihedral angle between two 1, 2, 4-triazole groups in the same fluconazole ligand is 68.25 (9) ° and the dihedral angle between two ipso-lateral 1, 2, 4-triazole groups in the same molecular binuclear copper cluster is 68.25 (9) ° (Fig. 1). In order to achieve the optimum coordination, fluconazole molecules were adjusted into epsilon-type arrangement.

Related literature top

For the use of 1,2,4-triazole and its derivatives in coordination chemistry, see: Haasnoot et al. (2000); Zhao et al. (2007). For 1,2,4-triazole as a bridging ligand, see: Liu et al. (2003); Park et al. (2006); Yi et al. (2004); Garcia et al. (2005).

Experimental top

A methanolic solution (15 ml) containing the Hflu ligand (0.5 mmol, 0.153 g) was added dropwise to a water solution (10 ml) containing Cu(ClO₄)₂ (0.5 mmol, 0.131 g). After stirring for 4 h, the solution was filtered. The filtered solution were evaporated for several days in the air and obtained deep-blue block-shaped crystals that was suitable for single-crystal X-ray diffraction (yield: 65.6% based on the ligand). Anal calc (%). for C₂₆H₂₂Cl₂Cu₂F₄N₁₂O₁₀: H, 2.37; C, 33.34; N, 17.95. Found: H, 2.45; C,33.41; N, 17.81.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 structure of the title compound and the atom-numbering scheme. The H atoms have been omitted for clarity. [Symmetry code: (i) -x, 1-y, -z.]
	Fig. 2. The packing diagram of the title compound.
	Fig. 3. The structure of Hfcz, the distinct binding mode of the ligand and the title compound.

Bis[µ-2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2- olato]dicopper(II) bis(perchlorate) top

Crystal data top

[Cu₂(C₁₃H₁₁F₂N₆O)₂](ClO₄)₂	D_x = 1.778 Mg m⁻³
M_r = 936.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnnm	Cell parameters from 3901 reflections
a = 15.4464 (18) Å	θ = 2.6–26.9°
b = 7.9532 (10) Å	µ = 1.46 mm⁻¹
c = 14.2407 (15) Å	T = 298 K
V = 1749.4 (4) Å³	Block, blue
Z = 2	0.49 × 0.45 × 0.43 mm
F(000) = 940

Data collection top

Bruker SMART 1000 diffractometer	1618 independent reflections
Radiation source: fine-focus sealed tube	1169 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→18
T_min = 0.534, T_max = 0.572	k = −9→9
7867 measured reflections	l = −16→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0552P)² + 3.7317P] where P = (F_o² + 2F_c²)/3
1618 reflections	(Δ/σ)_max = 0.001
162 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu₂(C₁₃H₁₁F₂N₆O)₂](ClO₄)₂	V = 1749.4 (4) Å³
M_r = 936.54	Z = 2
Orthorhombic, Pnnm	Mo Kα radiation
a = 15.4464 (18) Å	µ = 1.46 mm⁻¹
b = 7.9532 (10) Å	T = 298 K
c = 14.2407 (15) Å	0.49 × 0.45 × 0.43 mm

Data collection top

Bruker SMART 1000 diffractometer	1618 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1169 reflections with I > 2σ(I)
T_min = 0.534, T_max = 0.572	R_int = 0.024
7867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.09	Δρ_max = 0.55 e Å⁻³
1618 reflections	Δρ_min = −0.48 e Å⁻³
162 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cu1	0.0000	0.5000	0.10491 (4)	0.0387 (3)
Cl1	0.0000	1.0000	0.1949 (2)	0.0786 (7)
F1	0.3498 (3)	0.3943 (7)	0.0000	0.112 (2)
F2	0.3994 (4)	0.9719 (7)	0.0000	0.110 (2)
N1	0.1704 (2)	0.4153 (4)	0.1725 (2)	0.0412 (8)
N2	0.0936 (2)	0.4883 (4)	0.1947 (2)	0.0394 (8)
N3	0.1944 (3)	0.5620 (5)	0.2995 (3)	0.0595 (11)
O1	0.0783 (2)	0.4823 (5)	0.0000	0.0339 (8)
O2	0.009 (3)	0.8525 (18)	0.126 (2)	0.097 (7)	0.58 (10)
O3	0.0787 (17)	1.020 (6)	0.232 (3)	0.110 (11)	0.58 (10)
O2'	0.047 (4)	0.884 (6)	0.151 (3)	0.106 (13)	0.42 (10)
O3'	0.055 (3)	1.093 (8)	0.261 (3)	0.109 (11)	0.42 (10)
C1	0.1119 (3)	0.5755 (6)	0.2716 (3)	0.0503 (11)
H1	0.0711	0.6402	0.3033	0.060*
C2	0.2285 (3)	0.4627 (6)	0.2355 (3)	0.0546 (12)
H2	0.2863	0.4298	0.2346	0.066*
C3	0.1787 (3)	0.3154 (5)	0.0873 (3)	0.0433 (10)
H3A	0.1359	0.2260	0.0878	0.052*
H3B	0.2357	0.2641	0.0853	0.052*
C4	0.1658 (3)	0.4248 (7)	0.0000	0.0352 (12)
C5	0.2277 (4)	0.5736 (7)	0.0000	0.0395 (13)
C6	0.3173 (4)	0.5544 (9)	0.0000	0.0640 (19)
C7	0.3745 (5)	0.6848 (12)	0.0000	0.079 (2)
H7	0.4339	0.6656	0.0000	0.095*
C8	0.3431 (5)	0.8399 (11)	0.0000	0.069 (2)
C9	0.2571 (5)	0.8714 (9)	0.0000	0.0640 (19)
H9	0.2369	0.9815	0.0000	0.077*
C10	0.1993 (4)	0.7384 (7)	0.0000	0.0448 (14)
H10	0.1402	0.7604	0.0000	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0307 (4)	0.0620 (5)	0.0232 (3)	−0.0056 (3)	0.000	0.000
Cl1	0.0398 (9)	0.0638 (12)	0.132 (2)	0.0021 (9)	0.000	0.000
F1	0.049 (3)	0.078 (3)	0.208 (7)	0.022 (2)	0.000	0.000
F2	0.115 (4)	0.105 (4)	0.111 (4)	−0.075 (3)	0.000	0.000
N1	0.0453 (19)	0.0394 (18)	0.0390 (18)	−0.0007 (16)	−0.0119 (15)	0.0017 (16)
N2	0.0415 (18)	0.049 (2)	0.0276 (16)	−0.0035 (16)	−0.0047 (14)	0.0001 (15)
N3	0.061 (2)	0.064 (3)	0.054 (2)	−0.004 (2)	−0.022 (2)	−0.012 (2)
O1	0.0277 (18)	0.047 (2)	0.0268 (18)	0.0006 (16)	0.000	0.000
O2	0.073 (13)	0.066 (6)	0.153 (12)	−0.002 (6)	0.008 (10)	−0.014 (6)
O3	0.068 (8)	0.101 (17)	0.162 (17)	0.005 (9)	−0.027 (9)	−0.003 (15)
O2'	0.08 (2)	0.087 (15)	0.152 (17)	0.024 (16)	0.009 (16)	−0.013 (13)
O3'	0.078 (14)	0.10 (2)	0.151 (15)	0.002 (14)	−0.022 (11)	−0.018 (13)
C1	0.054 (3)	0.056 (3)	0.041 (2)	0.000 (2)	−0.010 (2)	−0.006 (2)
C2	0.049 (3)	0.059 (3)	0.056 (3)	0.002 (2)	−0.021 (2)	−0.004 (2)
C3	0.051 (2)	0.036 (2)	0.042 (2)	0.0042 (19)	−0.007 (2)	0.0003 (18)
C4	0.031 (3)	0.033 (3)	0.041 (3)	0.000 (2)	0.000	0.000
C5	0.035 (3)	0.039 (3)	0.045 (3)	0.001 (3)	0.000	0.000
C6	0.047 (4)	0.059 (4)	0.086 (5)	0.000 (3)	0.000	0.000
C7	0.047 (4)	0.089 (7)	0.101 (7)	−0.015 (4)	0.000	0.000
C8	0.068 (5)	0.067 (5)	0.071 (5)	−0.036 (4)	0.000	0.000
C9	0.080 (5)	0.045 (4)	0.067 (5)	−0.010 (4)	0.000	0.000
C10	0.048 (3)	0.042 (3)	0.045 (3)	−0.002 (3)	0.000	0.000

Geometric parameters (Å, º) top

Cu1—O1ⁱ	1.927 (2)	N3—C1	1.340 (6)
Cu1—O1	1.927 (2)	O1—C4	1.427 (6)
Cu1—N2	1.933 (3)	O1—Cu1ⁱ	1.927 (2)
Cu1—N2ⁱⁱ	1.933 (3)	C1—H1	0.9300
Cu1—Cu1ⁱ	2.9880 (13)	C2—H2	0.9300
Cl1—O2'	1.33 (2)	C3—C4	1.531 (5)
Cl1—O2'ⁱⁱⁱ	1.33 (2)	C3—H3A	0.9700
Cl1—O3ⁱⁱⁱ	1.336 (12)	C3—H3B	0.9700
Cl1—O3	1.336 (12)	C4—C5	1.522 (8)
Cl1—O3'	1.47 (3)	C4—C3^iv	1.531 (5)
Cl1—O3'ⁱⁱⁱ	1.47 (3)	C5—C10	1.382 (8)
Cl1—O2	1.53 (2)	C5—C6	1.392 (9)
Cl1—O2ⁱⁱⁱ	1.53 (2)	C6—C7	1.364 (10)
F1—C6	1.368 (9)	C7—C8	1.326 (12)
F2—C8	1.364 (8)	C7—H7	0.9300
N1—C2	1.324 (5)	C8—C9	1.352 (11)
N1—N2	1.358 (5)	C9—C10	1.383 (9)
N1—C3	1.456 (5)	C9—H9	0.9300
N2—C1	1.326 (5)	C10—H10	0.9300
N3—C2	1.316 (6)

O1ⁱ—Cu1—O1	78.33 (16)	C1—N2—Cu1	132.8 (3)
O1ⁱ—Cu1—N2	170.37 (12)	N1—N2—Cu1	121.3 (2)
O1—Cu1—N2	92.30 (13)	C2—N3—C1	102.9 (4)
O1ⁱ—Cu1—N2ⁱⁱ	92.30 (13)	C4—O1—Cu1ⁱ	128.15 (10)
O1—Cu1—N2ⁱⁱ	170.37 (12)	C4—O1—Cu1	128.15 (10)
N2—Cu1—N2ⁱⁱ	97.2 (2)	Cu1ⁱ—O1—Cu1	101.67 (16)
O1ⁱ—Cu1—Cu1ⁱ	39.16 (8)	N2—C1—N3	113.9 (4)
O1—Cu1—Cu1ⁱ	39.16 (8)	N2—C1—H1	123.0
N2—Cu1—Cu1ⁱ	131.42 (10)	N3—C1—H1	123.0
N2ⁱⁱ—Cu1—Cu1ⁱ	131.42 (10)	N3—C2—N1	111.7 (4)
O2'—Cl1—O2'ⁱⁱⁱ	124 (3)	N3—C2—H2	124.2
O2'—Cl1—O3ⁱⁱⁱ	127 (2)	N1—C2—H2	124.2
O2'ⁱⁱⁱ—Cl1—O3ⁱⁱⁱ	76.9 (12)	N1—C3—C4	110.8 (3)
O2'—Cl1—O3	76.9 (12)	N1—C3—H3A	109.5
O2'ⁱⁱⁱ—Cl1—O3	127 (2)	C4—C3—H3A	109.5
O3ⁱⁱⁱ—Cl1—O3	133 (4)	N1—C3—H3B	109.5
O2'—Cl1—O3'	110.0 (11)	C4—C3—H3B	109.5
O2'ⁱⁱⁱ—Cl1—O3'	105.2 (13)	H3A—C3—H3B	108.1
O3ⁱⁱⁱ—Cl1—O3'	109 (3)	O1—C4—C5	110.2 (4)
O3—Cl1—O3'	33.1 (6)	O1—C4—C3^iv	107.8 (3)
O2'—Cl1—O3'ⁱⁱⁱ	105.2 (13)	C5—C4—C3^iv	111.1 (3)
O2'ⁱⁱⁱ—Cl1—O3'ⁱⁱⁱ	110.0 (11)	O1—C4—C3	107.8 (3)
O3ⁱⁱⁱ—Cl1—O3'ⁱⁱⁱ	33.1 (6)	C5—C4—C3	111.1 (3)
O3—Cl1—O3'ⁱⁱⁱ	109 (3)	C3^iv—C4—C3	108.6 (4)
O3'—Cl1—O3'ⁱⁱⁱ	100 (2)	C10—C5—C6	114.8 (6)
O2'—Cl1—O2	28 (2)	C10—C5—C4	122.6 (5)
O2'ⁱⁱⁱ—Cl1—O2	106.2 (16)	C6—C5—C4	122.6 (6)
O3ⁱⁱⁱ—Cl1—O2	104.1 (11)	C7—C6—F1	118.0 (7)
O3—Cl1—O2	105.3 (11)	C7—C6—C5	124.1 (7)
O3'—Cl1—O2	138.4 (14)	F1—C6—C5	117.8 (6)
O3'ⁱⁱⁱ—Cl1—O2	94.2 (13)	C8—C7—C6	118.0 (7)
O2'—Cl1—O2ⁱⁱⁱ	106.2 (16)	C8—C7—H7	121.0
O2'ⁱⁱⁱ—Cl1—O2ⁱⁱⁱ	28 (2)	C6—C7—H7	121.0
O3ⁱⁱⁱ—Cl1—O2ⁱⁱⁱ	105.3 (11)	C7—C8—C9	122.2 (7)
O3—Cl1—O2ⁱⁱⁱ	104.1 (11)	C7—C8—F2	118.8 (8)
O3'—Cl1—O2ⁱⁱⁱ	94.2 (13)	C9—C8—F2	119.0 (8)
O3'ⁱⁱⁱ—Cl1—O2ⁱⁱⁱ	138.4 (14)	C8—C9—C10	119.5 (7)
O2—Cl1—O2ⁱⁱⁱ	101 (2)	C8—C9—H9	120.2
C2—N1—N2	108.2 (3)	C10—C9—H9	120.2
C2—N1—C3	131.3 (4)	C5—C10—C9	121.4 (6)
N2—N1—C3	120.3 (3)	C5—C10—H10	119.3
C1—N2—N1	103.3 (3)	C9—C10—H10	119.3

C2—N1—N2—C1	−0.3 (4)	Cu1—O1—C4—C5	−99.6 (3)
C3—N1—N2—C1	−176.2 (4)	Cu1ⁱ—O1—C4—C3^iv	−21.8 (5)
C2—N1—N2—Cu1	163.9 (3)	Cu1—O1—C4—C3^iv	138.9 (3)
C3—N1—N2—Cu1	−12.0 (5)	Cu1ⁱ—O1—C4—C3	−138.9 (3)
O1ⁱ—Cu1—N2—C1	121.8 (9)	Cu1—O1—C4—C3	21.8 (5)
O1—Cu1—N2—C1	135.0 (4)	N1—C3—C4—O1	−65.7 (4)
N2ⁱⁱ—Cu1—N2—C1	−46.9 (4)	N1—C3—C4—C5	55.2 (5)
Cu1ⁱ—Cu1—N2—C1	133.1 (4)	N1—C3—C4—C3^iv	177.8 (2)
O1ⁱ—Cu1—N2—N1	−37.0 (10)	O1—C4—C5—C10	0.0
O1—Cu1—N2—N1	−23.8 (3)	C3^iv—C4—C5—C10	119.5 (3)
N2ⁱⁱ—Cu1—N2—N1	154.3 (3)	C3—C4—C5—C10	−119.5 (3)
Cu1ⁱ—Cu1—N2—N1	−25.7 (3)	O1—C4—C5—C6	180.0
O1ⁱ—Cu1—O1—C4	−164.6 (5)	C3^iv—C4—C5—C6	−60.5 (3)
N2—Cu1—O1—C4	17.6 (4)	C3—C4—C5—C6	60.5 (3)
N2ⁱⁱ—Cu1—O1—C4	−151.2 (8)	C10—C5—C6—C7	0.0
Cu1ⁱ—Cu1—O1—C4	−164.6 (5)	C4—C5—C6—C7	180.0
O1ⁱ—Cu1—O1—Cu1ⁱ	0.0	C10—C5—C6—F1	180.0
N2—Cu1—O1—Cu1ⁱ	−177.77 (17)	C4—C5—C6—F1	0.0
N2ⁱⁱ—Cu1—O1—Cu1ⁱ	13.5 (10)	F1—C6—C7—C8	180.0
N1—N2—C1—N3	−0.3 (5)	C5—C6—C7—C8	0.0
Cu1—N2—C1—N3	−161.8 (3)	C6—C7—C8—C9	0.0
C2—N3—C1—N2	0.8 (6)	C6—C7—C8—F2	180.0
C1—N3—C2—N1	−0.9 (6)	C7—C8—C9—C10	0.0
N2—N1—C2—N3	0.8 (5)	F2—C8—C9—C10	180.0
C3—N1—C2—N3	176.1 (4)	C6—C5—C10—C9	0.0
C2—N1—C3—C4	−110.2 (5)	C4—C5—C10—C9	180.0
N2—N1—C3—C4	64.5 (5)	C8—C9—C10—C5	0.0
Cu1ⁱ—O1—C4—C5	99.6 (3)

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₃H₁₁F₂N₆O)₂](ClO₄)₂
M_r	936.54
Crystal system, space group	Orthorhombic, Pnnm
Temperature (K)	298
a, b, c (Å)	15.4464 (18), 7.9532 (10), 14.2407 (15)
V (Å³)	1749.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.49 × 0.45 × 0.43

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.534, 0.572
No. of measured, independent and observed [I > 2σ(I)] reflections	7867, 1618, 1169
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.129, 1.09
No. of reflections	1618
No. of parameters	162
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.48

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Innovation Project (gxun-chx2009080) of Guangxi University for Nationalities.

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