Bis[4,5-dimethyl-2-(2-pyrid­yl)-1H-imidazole-κ2N2,N3](1H-imidazole-κN3)copper(II) bis­(perchlorate)

Liu, C.; Zhou, A.; Wang, S.; Chen, Z.

doi:10.1107/S1600536808017273

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages m914-m915

doi:10.1107/S1600536808017273

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Bis[4,5-dimethyl-2-(2-pyridyl)-1H-imidazole-κ²N²,N³](1H-imidazole-κN³)copper(II) bis(perchlorate)

Chunyi Liu,^a Anyu Zhou,^b Songpei Wang ^a and Zhengping Chen ^a ^*

^aThe Key Laboratory of Nuclear Medicine, Ministry of Health P. R. China, Jiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China, and ^bDepartment of Chemistry & Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: lcy_hotmail@yahoo.com.cn

(Received 1 December 2007; accepted 9 June 2008; online 13 June 2008)

In the title complex, [Cu(C₃H₄N₂)(C₁₀H₁₁N₃)₂](ClO₄)₂, the Cu^II cation has a distorted trigonal-bipyramidal geometry defined by a CuN₂N′₂N′′ donor set. The imidazole ligand is disordered over two orientations of equal occupancy. Two of the perchlorate ion sites are located on a twofold rotation axis, and one of is disordered over two sites of equal occupancy. In the crystal structure there is a two-dimensional infinite network of hydrogen-bonded molecules parallel to the ab plane.

Related literature

For related literature, see: Holm et al. (1996 ); Huang et al. (2004 ); Huang et al. (2005 ); Kapinos et al. (1998 ); Matthews et al. (1998 ); Tan et al. (1997 ).

Experimental

Crystal data

[Cu(C₃H₄N₂)(C₁₀H₁₁N₃)₂](ClO₄)₂
M_r = 676.96
Tetragonal, P 4₁ 2₁ 2
a = 14.6374 (5) Å
c = 27.3945 (14) Å
V = 5869.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 293 (2) K
0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.74, T_max = 0.79
32170 measured reflections
5775 independent reflections
5315 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.117
S = 1.08
5775 reflections
410 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.64 e Å⁻³
Absolute structure: Flack (1983 ), 2433 Friedel pairs
Flack parameter: 0.013 (17)

Table 1
Selected geometric parameters (Å, °)

Cu1—N5	1.977 (3)
Cu1—N2	1.990 (3)
Cu1—N7	2.007 (3)
Cu1—N1	2.129 (3)
Cu1—N4	2.137 (3)

N5—Cu1—N2	170.20 (15)
N5—Cu1—N7	94.06 (14)
N2—Cu1—N7	95.74 (15)
N5—Cu1—N1	94.06 (13)
N2—Cu1—N1	80.10 (13)
N7—Cu1—N1	127.46 (14)
N5—Cu1—N4	79.52 (13)
N2—Cu1—N4	94.82 (13)
N7—Cu1—N4	123.73 (14)
N1—Cu1—N4	108.79 (13)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O12	0.86	2.16	3.001 (8)	166
N3—H3A⋯O14ⁱ	0.86	2.15	2.980 (10)	162
N6—H6⋯O21ⁱ	0.86	2.15	3.009 (5)	175
Symmetry code: (i) y, x, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017273/kj2084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017273/kj2084Isup2.hkl

checkCIF report

Comment top

Imidazole is ubiquitous in biology and chemistry. It is therefore of interest to synthesize ligands containing imidazole and related heterocyclic system (Tan et al., 1997; Kapinos et al., 1998; Matthews et al., 1998). Imidazole and its derivatives are an important class of heterocycle with N-donor atoms, therefore the investigation of mixed-ligand complexes of a variety of transitional metal ions with imidazole and its derivatives has attracted considerable interest in recent years. The copper-imidazole systems have demonstrated capacities for construction of inorganic-organic hybrid supramolecular isomers (Huang et al., 2004; Huang et al., 2005), and also have profound effects on functions in biological systems (Holm et al., 1996). We report here the crystal structure of the title compound, a mixed-ligand Cu^II complex.

The crystal structure of the title compound contains distorted Cu^II complexes in which individual Cu centres exist in a CuN₂N'₂N'' donor set that defines a distorted trigonal bipyramid geometry. The two N atoms of pyridyl rings and the N atom of imidazole coordinate in a plane around the Cu atom. The N atoms of the two imidazole rings distribute in the axial positions; the Cu1—N2 distance is 1.990 (3) Å. The imidazole ligand is not a ordered system, and the imidazole ring is disordered over two orientations. Two of the perchlorate ion sites (containing Cl1 and Cl2) are located on a twofold rotation axis, and one of these (containing Cl1) displays disorder.

The N3 atom of 4,5-dimethyl-2-(2-pyridyl)imidazole form two hydrogen bonds with the O atom of perchlorate. The N6 atom and N8 atom also each form a hydrogen bond with the O atom of perchlorate; details are presented in Table 2. A two-dimensional infinite network of hydrogen-bonded molecules is present in the structure, running parallel to the ab-plane.

Related literature top

For related literature, see: Holm et al. (1996); Huang et al. (2004); Huang et al. (2005); Kapinos et al. (1998); Matthews et al. (1998); Tan et al. (1997).

Experimental top

The title complex was synthesized by the reaction of 4,5-dimethyl-2- (2-pyridyl)imidazole (0.52 g, 3.0 mmol) and imidazole (0.10 g, 1.5 mmol) with copper(II) perchlorate (0.50 g, 1.5 mmol) dissolved in the methanol (20 ml). Single crystals of (I) suitable for X-ray diffraction were obtained by evaporation of the methanol solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: CrystalClear (Rigaku, 2005); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 the complex in (I), showing the atomic labelling. Displacement ellipsoids are shown at the 50% probability level. H atoms, counter ions and one disorder component have been omitted for clarity.

Bis[4,5-dimethyl-2-(2-pyridyl)-1H-imidazole-κ²N²,N³](1H- imidazole-κN³)copper(II) bis(perchlorate) top

Crystal data top

[Cu(C₃H₄N₂)(C₁₀H₁₁N₃)₂](ClO₄)₂	D_x = 1.532 Mg m⁻³
M_r = 676.96	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 8320 reflections
Hall symbol: P 4abw 2nw	θ = 2.5–23.8°
a = 14.6374 (5) Å	µ = 0.99 mm⁻¹
c = 27.3945 (14) Å	T = 293 K
V = 5869.4 (4) Å³	Bipyramid, green
Z = 8	0.32 × 0.26 × 0.24 mm
F(000) = 2776

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5775 independent reflections
Radiation source: sealed tube	5315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→14
T_min = 0.74, T_max = 0.79	k = −18→18
32170 measured reflections	l = −33→27

Refinement top

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.049P)² + 5.1204P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5775 reflections	Δρ_max = 0.54 e Å⁻³
410 parameters	Δρ_min = −0.64 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2433 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (17)

Crystal data top

[Cu(C₃H₄N₂)(C₁₀H₁₁N₃)₂](ClO₄)₂	Z = 8
M_r = 676.96	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 0.99 mm⁻¹
a = 14.6374 (5) Å	T = 293 K
c = 27.3945 (14) Å	0.32 × 0.26 × 0.24 mm
V = 5869.4 (4) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5775 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5315 reflections with I > 2σ(I)
T_min = 0.74, T_max = 0.79	R_int = 0.048
32170 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.117	Δρ_max = 0.54 e Å⁻³
S = 1.08	Δρ_min = −0.64 e Å⁻³
5775 reflections	Absolute structure: Flack (1983), 2433 Friedel pairs
410 parameters	Absolute structure parameter: 0.013 (17)
0 restraints

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	Occ. (<1)
Cu1	0.49074 (3)	0.81891 (3)	0.002420 (17)	0.04289 (13)
C1	0.5381 (3)	0.7035 (3)	−0.09104 (15)	0.0491 (10)
H1A	0.5698	0.7544	−0.1023	0.059*
C2	0.5351 (3)	0.6266 (3)	−0.12011 (16)	0.0560 (11)
H2A	0.5649	0.6258	−0.1501	0.067*
C3	0.4875 (3)	0.5508 (3)	−0.10421 (17)	0.0590 (12)
H3B	0.4848	0.4985	−0.1234	0.071*
C4	0.4438 (3)	0.5534 (3)	−0.05947 (17)	0.0547 (10)
H4A	0.4104	0.5037	−0.0482	0.066*
C5	0.4516 (3)	0.6338 (3)	−0.03163 (14)	0.0406 (8)
C6	0.4098 (3)	0.6474 (3)	0.01525 (14)	0.0434 (9)
C7	0.3344 (3)	0.6321 (3)	0.08455 (16)	0.0555 (11)
C8	0.3702 (3)	0.7184 (3)	0.08219 (16)	0.0531 (11)
C9	0.2772 (4)	0.5869 (4)	0.1227 (2)	0.0822 (17)
H9A	0.2638	0.5254	0.1128	0.123*
H9B	0.2213	0.6202	0.1267	0.123*
H9C	0.3099	0.5859	0.1531	0.123*
C10	0.3611 (5)	0.7958 (5)	0.1173 (2)	0.0863 (19)
H10A	0.3258	0.7764	0.1450	0.129*
H10B	0.3309	0.8460	0.1016	0.129*
H10C	0.4206	0.8147	0.1280	0.129*
C11	0.6139 (3)	0.7685 (3)	0.09316 (16)	0.0532 (11)
H11A	0.5641	0.7359	0.1051	0.064*
C12	0.6937 (3)	0.7703 (3)	0.12029 (17)	0.0557 (11)
H12A	0.6976	0.7394	0.1499	0.067*
C13	0.7668 (3)	0.8185 (3)	0.10272 (17)	0.0579 (12)
H13A	0.8209	0.8210	0.1205	0.070*
C14	0.7602 (3)	0.8632 (3)	0.05894 (17)	0.0551 (11)
H14A	0.8098	0.8950	0.0462	0.066*
C15	0.6777 (3)	0.8597 (2)	0.03390 (15)	0.0412 (8)
C16	0.6608 (2)	0.9028 (2)	−0.01296 (14)	0.0383 (8)
C17	0.6694 (3)	0.9807 (3)	−0.08144 (15)	0.0502 (9)
C18	0.5849 (3)	0.9440 (3)	−0.07755 (15)	0.0479 (10)
C19	0.7111 (4)	1.0404 (4)	−0.1201 (2)	0.0766 (16)
H19A	0.6671	1.0515	−0.1454	0.115*
H19B	0.7636	1.0104	−0.1338	0.115*
H19C	0.7294	1.0975	−0.1059	0.115*
C20	0.5027 (4)	0.9551 (4)	−0.1099 (2)	0.0757 (16)
H20A	0.5189	0.9907	−0.1380	0.114*
H20B	0.4550	0.9856	−0.0921	0.114*
H20C	0.4815	0.8961	−0.1201	0.114*
C21	0.4109 (4)	1.0078 (3)	0.0069 (2)	0.0658 (13)	0.50
H21A	0.4679	1.0357	0.0090	0.079*	0.50
C22	0.2631 (3)	0.9850 (4)	0.0016 (2)	0.075 (5)	0.50
H22A	0.2004	0.9950	−0.0001	0.090*	0.50
N8	0.3313 (4)	1.0509 (4)	0.00487 (19)	0.069 (3)	0.50
H8A	0.3233	1.1091	0.0055	0.083*	0.50
C23	0.3044 (3)	0.9069 (5)	0.0015 (2)	0.0707 (14)	0.50
H23A	0.2751	0.8507	−0.0010	0.085*	0.50
N7	0.3958 (2)	0.9177 (2)	0.00537 (13)	0.0492 (8)	0.50
C23'	0.4109 (4)	1.0078 (3)	0.0069 (2)	0.0658 (13)	0.50
H21B	0.4679	1.0357	0.0090	0.079*	0.50
N8'	0.2631 (3)	0.9850 (4)	0.0016 (2)	0.075 (3)	0.50
H8'A	0.2051	0.9942	0.0000	0.090*	0.50
N7'	0.3958 (2)	0.9177 (2)	0.00537 (13)	0.0492 (8)	0.50
C21'	0.3044 (3)	0.9069 (5)	0.0015 (2)	0.0707 (14)	0.50
H23B	0.2751	0.8507	−0.0010	0.085*	0.50
C22'	0.3313 (4)	1.0509 (4)	0.00487 (19)	0.069 (3)	0.50
H22B	0.3226	1.1138	0.0055	0.083*	0.50
N1	0.4977 (2)	0.7080 (2)	−0.04776 (12)	0.0412 (7)
N2	0.4179 (2)	0.7263 (2)	0.03865 (12)	0.0463 (8)
N3	0.3601 (2)	0.5891 (2)	0.04254 (14)	0.0514 (9)
H3A	0.3468	0.5338	0.0347	0.062*
N4	0.6058 (2)	0.8120 (2)	0.05027 (12)	0.0420 (7)
N5	0.5794 (2)	0.8946 (2)	−0.03395 (12)	0.0419 (7)
N6	0.7161 (2)	0.9535 (2)	−0.04085 (13)	0.0481 (8)
H6	0.7720	0.9668	−0.0343	0.058*
Cl1	0.32257 (8)	0.32257 (8)	0.0000	0.0702 (5)
O11	0.2532 (6)	0.2691 (6)	−0.0184 (2)	0.081 (3)	0.50
O12	0.2849 (7)	0.4105 (5)	0.0068 (4)	0.084 (2)	0.50
O13	0.3603 (6)	0.2882 (6)	0.0403 (3)	0.089 (3)	0.50
O14	0.3877 (6)	0.3325 (6)	−0.0371 (3)	0.080 (2)	0.50
Cl2	0.99578 (7)	0.99578 (7)	0.0000	0.0583 (4)
O21	0.9987 (3)	0.9145 (2)	0.02515 (14)	0.0775 (11)
O22	1.0050 (3)	1.0666 (3)	0.03420 (14)	0.0815 (12)
Cl3	0.66607 (8)	0.15608 (7)	0.02360 (4)	0.0550 (3)
O31	0.7316 (3)	0.1668 (3)	−0.01093 (13)	0.0798 (12)
O32	0.6524 (3)	0.2387 (3)	0.04837 (15)	0.0804 (12)
O33	0.6871 (3)	0.0867 (3)	0.05352 (15)	0.0864 (13)
O34	0.5931 (3)	0.1353 (3)	−0.00339 (17)	0.0867 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0378 (2)	0.0426 (3)	0.0483 (2)	−0.00376 (19)	0.0047 (2)	0.0029 (2)
C1	0.043 (2)	0.059 (3)	0.046 (2)	−0.0063 (19)	0.0089 (18)	0.0013 (19)
C2	0.050 (3)	0.074 (3)	0.044 (2)	0.003 (2)	0.0059 (19)	−0.011 (2)
C3	0.069 (3)	0.054 (3)	0.054 (3)	0.003 (2)	−0.006 (2)	−0.015 (2)
C4	0.056 (3)	0.045 (2)	0.063 (3)	−0.0016 (19)	0.001 (2)	−0.010 (2)
C5	0.0354 (19)	0.046 (2)	0.041 (2)	−0.0006 (16)	−0.0021 (16)	−0.0004 (17)
C6	0.041 (2)	0.046 (2)	0.043 (2)	−0.0021 (17)	0.0036 (17)	0.0039 (17)
C7	0.049 (2)	0.063 (3)	0.055 (2)	−0.003 (2)	0.005 (2)	0.011 (2)
C8	0.048 (2)	0.066 (3)	0.046 (2)	−0.006 (2)	0.0104 (19)	0.002 (2)
C9	0.084 (4)	0.086 (4)	0.077 (4)	−0.002 (3)	0.033 (3)	0.025 (3)
C10	0.099 (5)	0.092 (4)	0.068 (3)	−0.016 (4)	0.025 (3)	−0.022 (3)
C11	0.059 (3)	0.047 (2)	0.054 (3)	−0.007 (2)	−0.007 (2)	0.014 (2)
C12	0.061 (3)	0.049 (2)	0.057 (3)	−0.001 (2)	−0.015 (2)	0.006 (2)
C13	0.061 (3)	0.054 (3)	0.059 (3)	0.007 (2)	−0.023 (2)	−0.004 (2)
C14	0.043 (2)	0.057 (3)	0.066 (3)	−0.0044 (19)	−0.005 (2)	−0.006 (2)
C15	0.040 (2)	0.0344 (18)	0.049 (2)	−0.0007 (16)	−0.0077 (17)	−0.0044 (16)
C16	0.0306 (18)	0.0389 (19)	0.045 (2)	−0.0029 (15)	0.0010 (15)	0.0024 (16)
C17	0.055 (2)	0.046 (2)	0.050 (2)	0.0019 (19)	0.0063 (19)	0.0026 (18)
C18	0.047 (2)	0.049 (2)	0.048 (2)	0.0022 (18)	0.0001 (18)	0.0077 (18)
C19	0.065 (3)	0.079 (4)	0.086 (4)	−0.009 (3)	0.021 (3)	0.025 (3)
C20	0.072 (3)	0.095 (4)	0.060 (3)	0.003 (3)	−0.010 (3)	0.025 (3)
C21	0.083 (4)	0.044 (2)	0.071 (3)	−0.003 (2)	0.005 (3)	0.005 (2)
C22	0.055 (9)	0.089 (11)	0.081 (8)	0.02 (11)	0.01 (11)	0.02 (13)
N8	0.070 (7)	0.068 (7)	0.070 (6)	0.02 (10)	0.01 (9)	0.02 (9)
C23	0.046 (3)	0.095 (4)	0.071 (3)	−0.006 (3)	0.008 (3)	−0.011 (3)
N7	0.0397 (18)	0.0479 (19)	0.060 (2)	0.0012 (14)	−0.0002 (17)	−0.0015 (17)
C23'	0.083 (4)	0.044 (2)	0.071 (3)	−0.003 (2)	0.005 (3)	0.005 (2)
N8'	0.055 (6)	0.089 (6)	0.081 (3)	0.02 (10)	0.01 (9)	0.02 (11)
N7'	0.0397 (18)	0.0479 (19)	0.060 (2)	0.0012 (14)	−0.0002 (17)	−0.0015 (17)
C21'	0.046 (3)	0.095 (4)	0.071 (3)	−0.006 (3)	0.008 (3)	−0.011 (3)
C22'	0.070 (6)	0.068 (6)	0.070 (3)	0.02 (11)	0.01 (11)	0.02 (10)
N1	0.0327 (16)	0.0462 (18)	0.0449 (17)	−0.0019 (14)	0.0006 (14)	−0.0035 (14)
N2	0.0441 (19)	0.051 (2)	0.0436 (17)	−0.0092 (15)	0.0047 (15)	−0.0012 (16)
N3	0.050 (2)	0.0419 (18)	0.062 (2)	−0.0091 (15)	0.0039 (17)	0.0088 (17)
N4	0.0422 (17)	0.0372 (17)	0.0465 (18)	−0.0048 (14)	−0.0034 (14)	0.0044 (14)
N5	0.0346 (16)	0.0450 (18)	0.0460 (17)	−0.0004 (13)	0.0029 (14)	0.0051 (14)
N6	0.0363 (17)	0.049 (2)	0.059 (2)	−0.0059 (14)	−0.0003 (16)	0.0036 (16)
Cl1	0.0593 (6)	0.0593 (6)	0.0920 (13)	−0.0108 (8)	−0.0109 (8)	0.0109 (8)
O11	0.078 (6)	0.075 (5)	0.090 (6)	−0.035 (4)	0.034 (5)	−0.009 (5)
O12	0.102 (6)	0.052 (4)	0.098 (6)	−0.019 (4)	0.015 (6)	−0.027 (5)
O13	0.099 (6)	0.096 (6)	0.072 (5)	−0.050 (5)	−0.016 (5)	0.027 (4)
O14	0.095 (6)	0.074 (5)	0.072 (5)	−0.019 (5)	0.031 (5)	−0.014 (4)
Cl2	0.0531 (5)	0.0531 (5)	0.0686 (9)	−0.0092 (6)	0.0084 (6)	−0.0084 (6)
O21	0.094 (3)	0.0521 (19)	0.087 (2)	−0.0083 (19)	−0.043 (2)	0.0116 (18)
O22	0.093 (3)	0.074 (2)	0.078 (2)	−0.033 (2)	0.039 (2)	−0.0269 (19)
Cl3	0.0676 (7)	0.0422 (5)	0.0552 (6)	−0.0112 (5)	−0.0081 (5)	−0.0014 (4)
O31	0.072 (2)	0.097 (3)	0.070 (2)	−0.031 (2)	0.0292 (18)	−0.037 (2)
O32	0.078 (2)	0.064 (2)	0.099 (3)	0.0249 (19)	−0.039 (2)	−0.028 (2)
O33	0.085 (3)	0.083 (3)	0.092 (3)	0.039 (2)	−0.035 (2)	0.013 (2)
O34	0.095 (3)	0.065 (2)	0.101 (3)	−0.016 (2)	−0.024 (2)	−0.024 (2)

Geometric parameters (Å, º) top

Cu1—N5	1.977 (3)	C18—N5	1.398 (5)
Cu1—N2	1.990 (3)	C18—C20	1.503 (7)
Cu1—N7	2.007 (3)	C19—H19A	0.9600
Cu1—N1	2.129 (3)	C19—H19B	0.9600
Cu1—N4	2.137 (3)	C19—H19C	0.9600
C1—N1	1.327 (5)	C20—H20A	0.9600
C1—C2	1.380 (6)	C20—H20B	0.9600
C1—H1A	0.9300	C20—H20C	0.9600
C2—C3	1.380 (7)	C21—N8	1.326 (7)
C2—H2A	0.9300	C21—N7	1.338 (6)
C3—C4	1.383 (7)	C21—H21A	0.9300
C3—H3B	0.9300	C22—C23	1.293 (8)
C4—C5	1.407 (6)	C22—N8	1.392 (8)
C4—H4A	0.9300	C22—H22A	0.9300
C5—N1	1.352 (5)	N8—H8A	0.8600
C5—C6	1.437 (5)	C23—N7	1.352 (6)
C6—N2	1.326 (5)	C23—H23A	0.9300
C6—N3	1.347 (5)	N3—H3A	0.8600
C7—N3	1.364 (6)	N6—H6	0.8600
C7—C8	1.369 (6)	Cl1—O13	1.334 (8)
C7—C9	1.493 (6)	Cl1—O13ⁱ	1.334 (8)
C8—N2	1.386 (5)	Cl1—O11ⁱ	1.378 (7)
C8—C10	1.492 (7)	Cl1—O11	1.378 (7)
C9—H9A	0.9600	Cl1—O14ⁱ	1.401 (8)
C9—H9B	0.9600	Cl1—O14	1.401 (8)
C9—H9C	0.9600	Cl1—O12	1.413 (8)
C10—H10A	0.9600	Cl1—O12ⁱ	1.413 (8)
C10—H10B	0.9600	O11—O11ⁱ	1.060 (15)
C10—H10C	0.9600	O11—O13ⁱ	1.551 (10)
C11—N4	1.342 (5)	O12—O14ⁱ	1.135 (11)
C11—C12	1.385 (6)	O12—O13ⁱ	1.486 (11)
C11—H11A	0.9300	O13—O12ⁱ	1.486 (11)
C12—C13	1.369 (7)	O13—O14ⁱ	1.515 (13)
C12—H12A	0.9300	O13—O11ⁱ	1.551 (10)
C13—C14	1.369 (6)	O14—O12ⁱ	1.135 (11)
C13—H13A	0.9300	O14—O13ⁱ	1.515 (13)
C14—C15	1.391 (6)	Cl2—O21ⁱ	1.375 (3)
C14—H14A	0.9300	Cl2—O21	1.375 (3)
C15—N4	1.340 (5)	Cl2—O22	1.403 (3)
C15—C16	1.452 (5)	Cl2—O22ⁱ	1.403 (3)
C16—N5	1.327 (5)	Cl3—O34	1.334 (4)
C16—N6	1.338 (5)	Cl3—O33	1.341 (4)
C17—C18	1.353 (6)	Cl3—O31	1.356 (3)
C17—N6	1.365 (5)	Cl3—O32	1.402 (4)
C17—C19	1.504 (6)

N5—Cu1—N2	170.20 (15)	C23—C22—N8	106.1 (4)
N5—Cu1—N7	94.06 (14)	C23—C22—H22A	127.0
N2—Cu1—N7	95.74 (15)	N8—C22—H22A	127.0
N5—Cu1—N1	94.06 (13)	C21—N8—C22	107.7 (5)
N2—Cu1—N1	80.10 (13)	C21—N8—H8A	126.2
N7—Cu1—N1	127.46 (14)	C22—N8—H8A	126.2
N5—Cu1—N4	79.52 (13)	C22—C23—N7	111.1 (5)
N2—Cu1—N4	94.82 (13)	C22—C23—H23A	124.4
N7—Cu1—N4	123.73 (14)	N7—C23—H23A	124.4
N1—Cu1—N4	108.79 (13)	C21—N7—C23	106.3 (4)
N1—C1—C2	122.9 (4)	C21—N7—Cu1	126.7 (3)
N1—C1—H1A	118.6	C23—N7—Cu1	126.7 (4)
C2—C1—H1A	118.6	C1—N1—C5	118.3 (3)
C1—C2—C3	119.3 (4)	C1—N1—Cu1	129.5 (3)
C1—C2—H2A	120.4	C5—N1—Cu1	112.2 (2)
C3—C2—H2A	120.4	C6—N2—C8	107.4 (3)
C2—C3—C4	119.4 (4)	C6—N2—Cu1	113.6 (3)
C2—C3—H3B	120.3	C8—N2—Cu1	139.0 (3)
C4—C3—H3B	120.3	C6—N3—C7	109.0 (4)
C3—C4—C5	117.8 (4)	C6—N3—H3A	125.5
C3—C4—H4A	121.1	C7—N3—H3A	125.5
C5—C4—H4A	121.1	C15—N4—C11	118.1 (4)
N1—C5—C4	122.4 (4)	C15—N4—Cu1	112.9 (3)
N1—C5—C6	113.2 (3)	C11—N4—Cu1	129.0 (3)
C4—C5—C6	124.4 (4)	C16—N5—C18	105.8 (3)
N2—C6—N3	109.3 (4)	C16—N5—Cu1	114.9 (3)
N2—C6—C5	120.9 (4)	C18—N5—Cu1	139.2 (3)
N3—C6—C5	129.7 (4)	C16—N6—C17	108.8 (3)
N3—C7—C8	106.2 (4)	C16—N6—H6	125.6
N3—C7—C9	122.7 (4)	C17—N6—H6	125.6
C8—C7—C9	131.0 (5)	O13—Cl1—O13ⁱ	177.0 (6)
C7—C8—N2	108.1 (4)	O13—Cl1—O11ⁱ	69.8 (5)
C7—C8—C10	129.4 (4)	O13ⁱ—Cl1—O11ⁱ	113.2 (5)
N2—C8—C10	122.5 (4)	O13—Cl1—O11	113.2 (5)
C7—C9—H9A	109.5	O13ⁱ—Cl1—O11	69.8 (5)
C7—C9—H9B	109.5	O11ⁱ—Cl1—O11	45.3 (6)
H9A—C9—H9B	109.5	O13—Cl1—O14ⁱ	67.2 (6)
C7—C9—H9C	109.5	O13ⁱ—Cl1—O14ⁱ	111.0 (6)
H9A—C9—H9C	109.5	O11ⁱ—Cl1—O14ⁱ	107.1 (5)
H9B—C9—H9C	109.5	O11—Cl1—O14ⁱ	136.7 (5)
C8—C10—H10A	109.5	O13—Cl1—O14	111.0 (6)
C8—C10—H10B	109.5	O13ⁱ—Cl1—O14	67.2 (6)
H10A—C10—H10B	109.5	O11ⁱ—Cl1—O14	136.7 (5)
C8—C10—H10C	109.5	O11—Cl1—O14	107.1 (5)
H10A—C10—H10C	109.5	O14ⁱ—Cl1—O14	112.7 (7)
H10B—C10—H10C	109.5	O13—Cl1—O12	113.4 (6)
N4—C11—C12	122.3 (4)	O13ⁱ—Cl1—O12	65.4 (6)
N4—C11—H11A	118.8	O11ⁱ—Cl1—O12	113.7 (6)
C12—C11—H11A	118.8	O11—Cl1—O12	106.2 (6)
C13—C12—C11	118.7 (4)	O14ⁱ—Cl1—O12	47.6 (5)
C13—C12—H12A	120.6	O14—Cl1—O12	105.5 (5)
C11—C12—H12A	120.6	O13—Cl1—O12ⁱ	65.4 (6)
C12—C13—C14	119.9 (4)	O13ⁱ—Cl1—O12ⁱ	113.4 (6)
C12—C13—H13A	120.0	O11ⁱ—Cl1—O12ⁱ	106.2 (6)
C14—C13—H13A	120.0	O11—Cl1—O12ⁱ	113.7 (6)
C13—C14—C15	118.4 (4)	O14ⁱ—Cl1—O12ⁱ	105.5 (5)
C13—C14—H14A	120.8	O14—Cl1—O12ⁱ	47.6 (5)
C15—C14—H14A	120.8	O12—Cl1—O12ⁱ	136.7 (7)
N4—C15—C14	122.4 (4)	O11ⁱ—O11—Cl1	67.4 (3)
N4—C15—C16	112.9 (3)	O11ⁱ—O11—O13ⁱ	119.0 (5)
C14—C15—C16	124.6 (4)	Cl1—O11—O13ⁱ	53.8 (4)
N5—C16—N6	110.2 (3)	O14ⁱ—O12—Cl1	65.7 (6)
N5—C16—C15	119.8 (3)	O14ⁱ—O12—O13ⁱ	118.1 (9)
N6—C16—C15	130.0 (4)	Cl1—O12—O13ⁱ	54.7 (4)
C18—C17—N6	106.2 (4)	Cl1—O13—O12ⁱ	59.8 (5)
C18—C17—C19	131.2 (4)	Cl1—O13—O14ⁱ	58.5 (5)
N6—C17—C19	122.6 (4)	O12ⁱ—O13—O14ⁱ	96.5 (6)
C17—C18—N5	108.9 (4)	Cl1—O13—O11ⁱ	56.4 (4)
C17—C18—C20	130.0 (4)	O12ⁱ—O13—O11ⁱ	94.5 (6)
N5—C18—C20	120.9 (4)	O14ⁱ—O13—O11ⁱ	93.6 (7)
C17—C19—H19A	109.5	O12ⁱ—O14—Cl1	66.7 (6)
C17—C19—H19B	109.5	O12ⁱ—O14—O13ⁱ	119.4 (8)
H19A—C19—H19B	109.5	Cl1—O14—O13ⁱ	54.3 (4)
C17—C19—H19C	109.5	O21ⁱ—Cl2—O21	107.7 (3)
H19A—C19—H19C	109.5	O21ⁱ—Cl2—O22	113.3 (3)
H19B—C19—H19C	109.5	O21—Cl2—O22	107.5 (2)
C18—C20—H20A	109.5	O21ⁱ—Cl2—O22ⁱ	107.5 (2)
C18—C20—H20B	109.5	O21—Cl2—O22ⁱ	113.3 (3)
H20A—C20—H20B	109.5	O22—Cl2—O22ⁱ	107.7 (3)
C18—C20—H20C	109.5	O34—Cl3—O33	110.5 (3)
H20A—C20—H20C	109.5	O34—Cl3—O31	101.9 (3)
H20B—C20—H20C	109.5	O33—Cl3—O31	110.6 (3)
N8—C21—N7	108.8 (5)	O34—Cl3—O32	110.5 (2)
N8—C21—H21A	125.6	O33—Cl3—O32	113.0 (3)
N7—C21—H21A	125.6	O31—Cl3—O32	109.8 (3)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O12	0.86	2.16	3.001 (8)	166
N3—H3A···O14ⁱ	0.86	2.15	2.980 (10)	162
N6—H6···O21ⁱ	0.86	2.15	3.009 (5)	175

Symmetry code: (i) y, x, −z.

Experimental details

Crystal data
Chemical formula	[Cu(C₃H₄N₂)(C₁₀H₁₁N₃)₂](ClO₄)₂
M_r	676.96
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	293
a, c (Å)	14.6374 (5), 27.3945 (14)
V (Å³)	5869.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.32 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.74, 0.79
No. of measured, independent and observed [I > 2σ(I)] reflections	32170, 5775, 5315
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.117, 1.08
No. of reflections	5775
No. of parameters	410
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.64
Absolute structure	Flack (1983), 2433 Friedel pairs
Absolute structure parameter	0.013 (17)

Computer programs: SMART (Bruker, 2000), CrystalClear (Rigaku, 2005), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—N5	1.977 (3)	Cu1—N1	2.129 (3)
Cu1—N2	1.990 (3)	Cu1—N4	2.137 (3)
Cu1—N7	2.007 (3)

N5—Cu1—N2	170.20 (15)	N7—Cu1—N1	127.46 (14)
N5—Cu1—N7	94.06 (14)	N5—Cu1—N4	79.52 (13)
N2—Cu1—N7	95.74 (15)	N2—Cu1—N4	94.82 (13)
N5—Cu1—N1	94.06 (13)	N7—Cu1—N4	123.73 (14)
N2—Cu1—N1	80.10 (13)	N1—Cu1—N4	108.79 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O12	0.86	2.16	3.001 (8)	166.0
N3—H3A···O14ⁱ	0.86	2.15	2.980 (10)	162.1
N6—H6···O21ⁱ	0.86	2.15	3.009 (5)	174.5

Symmetry code: (i) y, x, −z.

Acknowledgements

We are grateful for the support provided by the National Natural Science Foundation of China (30570518), the Science Foundation of the Health Department of Jiangsu Province (H200401) and the High Technology Research and Development Program of Jiangsu Province (BG2007603).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Volume 64| Part 7| July 2008| Pages m914-m915

doi:10.1107/S1600536808017273

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