Hexa-μ-chlorido-μ4-oxido-tetra­kis­({1-[(pyridin-2-yl)meth­yl]-1H-benzimidazole-κN3}copper(II))

Li, H.; Jiang, H.; Sun, H.

doi:10.1107/S1600536811035252

metal-organic compounds

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Volume 67| Part 10| October 2011| Page m1372

https://doi.org/10.1107/S1600536811035252

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Hexa-μ-chlorido-μ₄-oxido-tetrakis({1-[(pyridin-2-yl)methyl]-1H-benzimidazole-κN³}copper(II))

Hui Li,^a ^* Hongshi Jiang ^a and Hong Sun ^a

^aDepartment of Applied Chemistry, Yuncheng University, Yuncheng, Shanxi 044000, People's Republic of China
^*Correspondence e-mail: lihuiwff@163.com

(Received 22 August 2011; accepted 29 August 2011; online 14 September 2011)

The title tetranuclear complex, [Cu₄Cl₆O(C₁₃H₁₁N₃)₄], features a tetrahedral arrangement of copper(II) ions bonded to the central O atom (site symmetry $[\overline{4}]$ ). Each of the six edges of the Cu₄ tetrahedron is bridged by a chloride ion (one of which has site symmetry 2), so that each copper ion is linked to the other three metal ions through the central O atom and through three separate chloride-ion bridges. The fifth coordination position, located on the central Cu—O axis on the outside of the cluster, is occupied by an N atom of the monodentate 1-(pyridin-2-ylmethyl)-1H-benzimidazole ligand. The resulting coordination geometry of the metal ion is a distorted trigonal bipyramid with the O and N atoms in the axial positions. The dihedral angle between the benzimidazole ring system and the pendant pyridine ring is 61.0 (2)°.

Related literature

For background to polynuclear copper halides, see: Willett (1991 ); Chivers et al. (2005 ); Li et al. (2009 ).

Experimental

Crystal data

[Cu₄Cl₆O(C₁₃H₁₁N₃)₄]
M_r = 1319.85
Tetragonal, $[I \overline 4]$
a = 13.8532 (12) Å
c = 14.507 (3) Å
V = 2784.1 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.85 mm⁻¹
T = 294 K
0.25 × 0.23 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.637, T_max = 0.691
7149 measured reflections
2467 independent reflections
2178 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.062
S = 1.06
2467 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983), 1172 Friedel pairs
Flack parameter: 0.005 (15)

Table 1
Selected bond lengths (Å)

Cu1—O1	1.9199 (4)
Cu1—N3	1.974 (3)
Cu1—Cl1ⁱ	2.3961 (10)
Cu1—Cl1	2.4192 (10)
Cu1—Cl2	2.4263 (10)
Symmetry code: (i) -y+1, x, -z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: https://doi.org/10.1107/S1600536811035252/hb6384sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035252/hb6384Isup2.hkl

checkCIF report

Comment top

Copper(II) halide framework materials have attracted much attention for their interesting magnetic properties and structural richness (Willett et al., 1991). The most commonly employed technique to modulate the inorganic network involves the direct addition of an organic ligand as a templating reagent (Chivers et al., 2005). benzimidazole has been well used in crystal engineering, and a large number of benzimidazole ligands have been extensively studied (Li et al., 2009). The reaction of CuCl₂ with the benzimidazole-pyridine ligand (L) affords a tetranuclear molecule [(Cu₄O)Cl₆(L)₄], (I). The crystal structure was elucidated by X-ray diffraction analysis.

Related literature top

For background to polynuclear copper halides, see: Willett (1991); Chivers et al.(2005); Li et al. (2009).

Experimental top

To a solution of L (0.12 mmol, 25 mg) dissolved in CH₃CN (9 ml), a solution of CuCl₂^.6H₂O (0.12 mmol, 28.9 mg) in H₂O (9 ml) was added under stirring in a few minutes. The solution was left to stand at room temperature. Brown blocks of (I) were obtained after several days with solvent evaporation. Yield: ~20% (based on L).

Structure description top

For background to polynuclear copper halides, see: Willett (1991); Chivers et al.(2005); Li et al. (2009).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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). Displacement ellipsoids are drawn at the 30% probability level and H atoms are removed for clarity. [symmetry code: (A) -y + 1, x, -z; (B) y, -x + 1, -z; (C) -x + 1, -y + 1, z].
	Fig. 2. The crystal packing for (I) viewed along the c axis.

Hexa-µ-chlorido-µ₄-oxido-tetrakis({1-[(pyridin-2-yl)methyl]- 1H-benzimidazole-κN³}copper(II)) top

Crystal data top

[Cu₄Cl₆O(C₁₃H₁₁N₃)₄]	D_x = 1.574 Mg m⁻³
M_r = 1319.85	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 3492 reflections
a = 13.8532 (12) Å	θ = 2.8–25.3°
c = 14.507 (3) Å	µ = 1.85 mm⁻¹
V = 2784.1 (6) Å³	T = 294 K
Z = 2	Block, brown
F(000) = 1332	0.25 × 0.23 × 0.20 mm

Data collection top

Rigaku Mercury CCD diffractometer	2467 independent reflections
Radiation source: fine-focus sealed tube	2178 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −14→16
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −16→14
T_min = 0.637, T_max = 0.691	l = −17→17
7149 measured reflections

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.062	w = 1/[σ²(F_o²) + (0.0286P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2467 reflections	Δρ_max = 0.34 e Å⁻³
170 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1172 Friedel pairs
0 constraints	Absolute structure parameter: 0.005 (15)
Primary atom site location: structure-invariant direct methods

Crystal data top

[Cu₄Cl₆O(C₁₃H₁₁N₃)₄]	Z = 2
M_r = 1319.85	Mo Kα radiation
Tetragonal, I4	µ = 1.85 mm⁻¹
a = 13.8532 (12) Å	T = 294 K
c = 14.507 (3) Å	0.25 × 0.23 × 0.20 mm
V = 2784.1 (6) Å³

Data collection top

Rigaku Mercury CCD diffractometer	2467 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2178 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.691	R_int = 0.033
7149 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.062	Δρ_max = 0.34 e Å⁻³
S = 1.06	Δρ_min = −0.17 e Å⁻³
2467 reflections	Absolute structure: Flack (1983), 1172 Friedel pairs
170 parameters	Absolute structure parameter: 0.005 (15)
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
Cu1	0.42929 (3)	0.41004 (3)	0.07467 (3)	0.03400 (12)
Cl1	0.28847 (6)	0.47255 (6)	−0.00384 (7)	0.0473 (2)
Cl2	0.5000	0.5000	0.20129 (8)	0.0637 (4)
N3	0.3550 (2)	0.3189 (2)	0.1515 (2)	0.0412 (7)
C1	0.3592 (3)	0.2243 (3)	0.1520 (3)	0.0498 (10)
H1	0.3992	0.1887	0.1133	0.060*
C2	0.2867 (3)	0.3436 (3)	0.2180 (2)	0.0485 (10)
C7	0.2518 (3)	0.2588 (3)	0.2595 (3)	0.0533 (10)
N2	0.2998 (3)	0.1839 (2)	0.2144 (2)	0.0548 (9)
C6	0.1844 (3)	0.2627 (4)	0.3322 (3)	0.0736 (15)
H6	0.1636	0.2068	0.3616	0.088*
C3	0.2513 (3)	0.4325 (3)	0.2461 (3)	0.0663 (13)
H3	0.2726	0.4892	0.2184	0.080*
C4	0.1837 (4)	0.4350 (4)	0.3161 (4)	0.0844 (16)
H4	0.1593	0.4940	0.3359	0.101*
C5	0.1515 (4)	0.3495 (5)	0.3574 (4)	0.0899 (18)
H5	0.1056	0.3532	0.4040	0.108*
C8	0.2900 (4)	0.0806 (3)	0.2368 (3)	0.0755 (15)
H8A	0.2343	0.0721	0.2764	0.091*
H8B	0.3465	0.0601	0.2711	0.091*
O1	0.5000	0.5000	0.0000	0.0292 (9)
C9	0.2789 (3)	0.0170 (3)	0.1543 (3)	0.0563 (10)
C10	0.1944 (4)	−0.0195 (4)	0.1286 (4)	0.0846 (16)
H10	0.1380	−0.0038	0.1600	0.102*
N1	0.3632 (4)	−0.0017 (4)	0.1100 (4)	0.1075 (18)
C12	0.2815 (9)	−0.1018 (5)	0.0115 (5)	0.128 (3)
H12	0.2863	−0.1449	−0.0374	0.154*
C11	0.1926 (7)	−0.0858 (5)	0.0487 (5)	0.116 (2)
H11	0.1364	−0.1138	0.0261	0.139*
C13	0.3600 (8)	−0.0601 (5)	0.0405 (6)	0.140 (4)
H13	0.4172	−0.0730	0.0093	0.168*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0374 (2)	0.0322 (2)	0.03237 (19)	−0.00702 (17)	0.0024 (2)	0.00311 (19)
Cl1	0.0319 (5)	0.0549 (5)	0.0552 (5)	−0.0045 (4)	−0.0026 (4)	0.0094 (5)
Cl2	0.0911 (11)	0.0707 (10)	0.0294 (6)	−0.0472 (9)	0.000	0.000
N3	0.0419 (18)	0.0393 (18)	0.0425 (16)	−0.0130 (14)	0.0009 (14)	0.0065 (14)
C1	0.061 (3)	0.045 (2)	0.043 (2)	−0.0162 (19)	−0.006 (2)	0.0044 (19)
C2	0.045 (2)	0.058 (3)	0.042 (2)	−0.0166 (19)	−0.0002 (18)	0.007 (2)
C7	0.054 (2)	0.060 (3)	0.045 (2)	−0.021 (2)	0.001 (2)	0.010 (2)
N2	0.068 (2)	0.048 (2)	0.048 (2)	−0.0231 (17)	−0.0028 (18)	0.0152 (17)
C6	0.064 (3)	0.096 (4)	0.061 (3)	−0.035 (3)	0.005 (2)	0.030 (3)
C3	0.073 (3)	0.060 (3)	0.066 (3)	−0.015 (2)	0.021 (3)	0.003 (2)
C4	0.083 (4)	0.080 (4)	0.091 (4)	−0.003 (3)	0.037 (3)	0.002 (3)
C5	0.084 (4)	0.102 (5)	0.084 (4)	−0.016 (3)	0.040 (3)	0.002 (3)
C8	0.108 (4)	0.054 (3)	0.065 (3)	−0.030 (3)	−0.008 (3)	0.021 (2)
O1	0.0293 (14)	0.0293 (14)	0.029 (2)	0.000	0.000	0.000
C9	0.064 (3)	0.042 (2)	0.064 (3)	−0.002 (2)	0.010 (2)	0.020 (2)
C10	0.093 (4)	0.081 (4)	0.081 (4)	−0.020 (3)	0.010 (3)	0.001 (3)
N1	0.107 (4)	0.085 (3)	0.130 (5)	0.035 (3)	0.033 (3)	0.025 (3)
C12	0.229 (11)	0.066 (4)	0.090 (5)	−0.007 (6)	0.033 (7)	0.000 (4)
C11	0.158 (7)	0.092 (5)	0.097 (5)	−0.030 (5)	−0.005 (5)	0.008 (4)
C13	0.202 (10)	0.064 (5)	0.154 (8)	0.052 (5)	0.079 (7)	0.012 (5)

Geometric parameters (Å, º) top

Cu1—O1	1.9199 (4)	C4—C5	1.400 (7)
Cu1—N3	1.974 (3)	C4—H4	0.9300
Cu1—Cl1ⁱ	2.3961 (10)	C5—H5	0.9300
Cu1—Cl1	2.4192 (10)	C8—C9	1.494 (7)
Cu1—Cl2	2.4263 (10)	C8—H8A	0.9700
Cl1—Cu1ⁱⁱ	2.3961 (9)	C8—H8B	0.9700
Cl2—Cu1ⁱⁱⁱ	2.4263 (10)	O1—Cu1ⁱⁱⁱ	1.9199 (4)
N3—C1	1.313 (4)	O1—Cu1ⁱ	1.9199 (4)
N3—C2	1.394 (5)	O1—Cu1ⁱⁱ	1.9199 (4)
C1—N2	1.345 (5)	C9—C10	1.328 (6)
C1—H1	0.9300	C9—N1	1.358 (6)
C2—C3	1.386 (6)	C10—C11	1.480 (8)
C2—C7	1.407 (5)	C10—H10	0.9300
C7—N2	1.395 (6)	N1—C13	1.293 (9)
C7—C6	1.409 (6)	C12—C13	1.301 (12)
N2—C8	1.474 (5)	C12—C11	1.362 (10)
C6—C5	1.337 (8)	C12—H12	0.9300
C6—H6	0.9300	C11—H11	0.9300
C3—C4	1.382 (6)	C13—H13	0.9300
C3—H3	0.9300

O1—Cu1—N3	179.14 (9)	C3—C4—H4	119.7
O1—Cu1—Cl1ⁱ	85.68 (3)	C5—C4—H4	119.7
N3—Cu1—Cl1ⁱ	95.10 (9)	C6—C5—C4	122.3 (5)
O1—Cu1—Cl1	85.03 (3)	C6—C5—H5	118.8
N3—Cu1—Cl1	94.25 (9)	C4—C5—H5	118.8
Cl1ⁱ—Cu1—Cl1	120.483 (17)	N2—C8—C9	113.9 (4)
O1—Cu1—Cl2	83.56 (2)	N2—C8—H8A	108.8
N3—Cu1—Cl2	96.40 (9)	C9—C8—H8A	108.8
Cl1ⁱ—Cu1—Cl2	117.17 (3)	N2—C8—H8B	108.8
Cl1—Cu1—Cl2	119.88 (3)	C9—C8—H8B	108.8
Cu1ⁱⁱ—Cl1—Cu1	80.69 (3)	H8A—C8—H8B	107.7
Cu1—Cl2—Cu1ⁱⁱⁱ	81.58 (4)	Cu1ⁱⁱⁱ—O1—Cu1ⁱ	108.564 (12)
C1—N3—C2	105.8 (3)	Cu1ⁱⁱⁱ—O1—Cu1	111.30 (2)
C1—N3—Cu1	128.2 (3)	Cu1ⁱ—O1—Cu1	108.564 (12)
C2—N3—Cu1	126.0 (2)	Cu1ⁱⁱⁱ—O1—Cu1ⁱⁱ	108.564 (12)
N3—C1—N2	113.1 (4)	Cu1ⁱ—O1—Cu1ⁱⁱ	111.30 (2)
N3—C1—H1	123.5	Cu1—O1—Cu1ⁱⁱ	108.564 (12)
N2—C1—H1	123.5	C10—C9—N1	123.5 (5)
C3—C2—N3	131.4 (3)	C10—C9—C8	122.7 (5)
C3—C2—C7	119.6 (4)	N1—C9—C8	113.8 (5)
N3—C2—C7	108.9 (4)	C9—C10—C11	118.1 (6)
N2—C7—C2	104.9 (4)	C9—C10—H10	121.0
N2—C7—C6	134.1 (4)	C11—C10—H10	121.0
C2—C7—C6	121.0 (5)	C13—N1—C9	117.3 (7)
C1—N2—C7	107.4 (3)	C13—C12—C11	123.7 (8)
C1—N2—C8	127.5 (4)	C13—C12—H12	118.1
C7—N2—C8	125.1 (4)	C11—C12—H12	118.1
C5—C6—C7	117.8 (4)	C12—C11—C10	113.3 (7)
C5—C6—H6	121.1	C12—C11—H11	123.3
C7—C6—H6	121.1	C10—C11—H11	123.3
C4—C3—C2	118.6 (4)	N1—C13—C12	123.9 (8)
C4—C3—H3	120.7	N1—C13—H13	118.0
C2—C3—H3	120.7	C12—C13—H13	118.0
C3—C4—C5	120.6 (5)

O1—Cu1—Cl1—Cu1ⁱⁱ	−1.10 (2)	N2—C7—C6—C5	−178.9 (5)
N3—Cu1—Cl1—Cu1ⁱⁱ	178.42 (9)	C2—C7—C6—C5	3.0 (7)
Cl1ⁱ—Cu1—Cl1—Cu1ⁱⁱ	−83.12 (4)	N3—C2—C3—C4	−178.9 (4)
Cl2—Cu1—Cl1—Cu1ⁱⁱ	78.54 (4)	C7—C2—C3—C4	1.4 (7)
O1—Cu1—Cl2—Cu1ⁱⁱⁱ	0.0	C2—C3—C4—C5	−0.2 (8)
N3—Cu1—Cl2—Cu1ⁱⁱⁱ	−179.13 (9)	C7—C6—C5—C4	−1.8 (9)
Cl1ⁱ—Cu1—Cl2—Cu1ⁱⁱⁱ	81.77 (3)	C3—C4—C5—C6	0.5 (9)
Cl1—Cu1—Cl2—Cu1ⁱⁱⁱ	−80.48 (3)	C1—N2—C8—C9	−48.8 (6)
O1—Cu1—N3—C1	150 (6)	C7—N2—C8—C9	135.3 (4)
Cl1ⁱ—Cu1—N3—C1	−4.5 (3)	N3—Cu1—O1—Cu1ⁱⁱⁱ	88 (6)
Cl1—Cu1—N3—C1	116.6 (3)	Cl1ⁱ—Cu1—O1—Cu1ⁱⁱⁱ	−117.99 (3)
Cl2—Cu1—N3—C1	−122.7 (3)	Cl1—Cu1—O1—Cu1ⁱⁱⁱ	120.87 (3)
O1—Cu1—N3—C2	−31 (6)	Cl2—Cu1—O1—Cu1ⁱⁱⁱ	0.0
Cl1ⁱ—Cu1—N3—C2	174.8 (3)	N3—Cu1—O1—Cu1ⁱ	−153 (6)
Cl1—Cu1—N3—C2	−64.1 (3)	Cl1ⁱ—Cu1—O1—Cu1ⁱ	1.44 (3)
Cl2—Cu1—N3—C2	56.7 (3)	Cl1—Cu1—O1—Cu1ⁱ	−119.70 (3)
C2—N3—C1—N2	−0.7 (4)	Cl2—Cu1—O1—Cu1ⁱ	119.434 (8)
Cu1—N3—C1—N2	178.8 (2)	N3—Cu1—O1—Cu1ⁱⁱ	−32 (6)
C1—N3—C2—C3	−178.6 (4)	Cl1ⁱ—Cu1—O1—Cu1ⁱⁱ	122.58 (3)
Cu1—N3—C2—C3	2.0 (6)	Cl1—Cu1—O1—Cu1ⁱⁱ	1.43 (3)
C1—N3—C2—C7	1.2 (4)	Cl2—Cu1—O1—Cu1ⁱⁱ	−119.434 (8)
Cu1—N3—C2—C7	−178.3 (2)	N2—C8—C9—C10	−102.8 (6)
C3—C2—C7—N2	178.6 (4)	N2—C8—C9—N1	78.9 (5)
N3—C2—C7—N2	−1.2 (4)	N1—C9—C10—C11	1.4 (7)
C3—C2—C7—C6	−2.8 (6)	C8—C9—C10—C11	−176.8 (4)
N3—C2—C7—C6	177.4 (4)	C10—C9—N1—C13	−1.6 (7)
N3—C1—N2—C7	−0.1 (4)	C8—C9—N1—C13	176.8 (5)
N3—C1—N2—C8	−176.6 (4)	C13—C12—C11—C10	−2.7 (10)
C2—C7—N2—C1	0.8 (4)	C9—C10—C11—C12	0.6 (8)
C6—C7—N2—C1	−177.6 (5)	C9—N1—C13—C12	−0.5 (10)
C2—C7—N2—C8	177.4 (4)	C11—C12—C13—N1	2.8 (13)
C6—C7—N2—C8	−1.0 (8)

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

Experimental details

Crystal data
Chemical formula	[Cu₄Cl₆O(C₁₃H₁₁N₃)₄]
M_r	1319.85
Crystal system, space group	Tetragonal, I4
Temperature (K)	294
a, c (Å)	13.8532 (12), 14.507 (3)
V (Å³)	2784.1 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.25 × 0.23 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.637, 0.691
No. of measured, independent and observed [I > 2σ(I)] reflections	7149, 2467, 2178
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.062, 1.06
No. of reflections	2467
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.17
Absolute structure	Flack (1983), 1172 Friedel pairs
Absolute structure parameter	0.005 (15)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O1	1.9199 (4)	Cu1—Cl1	2.4192 (10)
Cu1—N3	1.974 (3)	Cu1—Cl2	2.4263 (10)
Cu1—Cl1ⁱ	2.3961 (10)

Symmetry code: (i) −y+1, x, −z.

Acknowledgements

We thank the College Research Program of Yuncheng University (2008112) for funding.

References

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