catena-Poly[[dinitratocopper(II)]-μ-4,4′′-bis­(1H-benzimidazol-1-yl)-1,1′:4′,1′′-terphen­yl]

Jiang, H.-S.; Li, H.; Wang, J.; Ma, H.-X.; Zhang, Z.

doi:10.1107/S1600536811013596

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m603

doi:10.1107/S1600536811013596

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catena-Poly[[dinitratocopper(II)]-μ-4,4′′-bis(1H-benzimidazol-1-yl)-1,1′:4′,1′′-terphenyl]

Hong-Shi Jiang,^a ^* Hui Li,^a Jian Wang,^a Hui-Xuan Ma ^a and Zhe Zhang ^a

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

(Received 10 April 2011; accepted 11 April 2011; online 16 April 2011)

In the title one-dimensional coordination polymer, [Cu(NO₃)₂(C₃₂H₂₂N₄)]_n, the Cu²⁺ ion (site symmetry 2) is coordinated by two nitrate O atoms and two N atoms from two 4,4′-bis(benzoimidazol-1-yl)terphenyl (L) ligands in a distorted cis-CuN₂O₂ square-planar coordination geometry. An alternative description of the metal coordination geometry, if long Cu—O contacts to the bonded nitrate anions are considered, is an extremely distorted cis-CuN₂O₄ octahedron. The complete L ligand is generated by crystallographic twofold symmetry and connects the metal ions into infinite chains propagating in [10 $[\overline{1}]$ ]. The dihedral angle between the benzimidazole ring system and the adjacent benzene (B) ring is 51.12 (11)° and the dihedral angle between the B ring and the central ring is 19.45 (13)°.

Related literature

For background to benzimidazole-derived ligands in coordination polymers, see: Jin et al. (2006 ); Li et al. (2010 ); Su et al. (2003 ).

Experimental

Crystal data

[Cu(NO₃)₂(C₃₂H₂₂N₄)]
M_r = 650.10
Monoclinic, C 2/c
a = 14.960 (3) Å
b = 15.237 (3) Å
c = 12.139 (2) Å
β = 103.94 (3)°
V = 2685.7 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.839, T_max = 0.877
13493 measured reflections
2371 independent reflections
2181 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.124
S = 1.09
2371 reflections
204 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	1.985 (2)
Cu1—O1	2.025 (2)
Cu1—O3	2.452 (3)

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: 10.1107/S1600536811013596/hb5843sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013596/hb5843Isup2.hkl

checkCIF report

Comment top

Benzimidazole has been well used in crystal engineering, and a large number of benzimidazole-containing flexible ligands have been extensively studied (Su et al.,2003; Jin et al.,2006). However, to our knowledge, the research on benzoimidazole ligands bearing rigid spacers is still less developed (Li et al.,2010).

Single-crystal X-ray diffraction analysis reveals that the title compound (I) crystallizes in the monoclinic space group C2/c. The geometry of the Cu(II) ion is surrounded by two benzoiimidazole rings of individual L ligands and two nitrate anions, which illustrates a distorted square coordination environment (Fig. 1). Notably, as shown in Fig. 2, the four-coordinated Cu(II) center is bridged by the linear ligand L to form an infinite one-dimensional architecture.

Related literature top

For background to benzimidazole-derived ligands in coordination polymers, see: Jin et al. (2006); Li et al. (2010); Su et al. (2003).

Experimental top

A mixture of CH₃OH and CHCl₃ (1:1, 8 ml), as a buffer layer, was carefully layered over a solution of 4,4'-Bis(benzoimidazol-1-yl)terphenyl (L, 0.06 mmol) in CHCl₃ (6 ml). Then, a solution of Cu(NO₃)₂ (0.02 mmol) in CH₃OH (6 ml) was layered over the buffer layer, and the resultant reaction was left to stand at room temperature. After ca three weeks, green block single crystals appeared at the boundary. Yield: ~30% (based on L).

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 shown as small spheres of arbitrary radius.
	Fig. 2. The crystal packing for (I).

catena-Poly[[dinitratocopper(II)]-µ-4,4''-bis(1H- benzimidazol-1-yl)-1,1':4',1''-terphenyl] top

Crystal data top

[Cu(NO₃)₂(C₃₂H₂₂N₄)]	F(000) = 1332
M_r = 650.10	D_x = 1.608 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4661 reflections
a = 14.960 (3) Å	θ = 1.9–28.7°
b = 15.237 (3) Å	µ = 0.88 mm⁻¹
c = 12.139 (2) Å	T = 293 K
β = 103.94 (3)°	Block, green
V = 2685.7 (9) Å³	0.20 × 0.18 × 0.15 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	2371 independent reflections
Radiation source: fine-focus sealed tube	2181 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ω scans	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→18
T_min = 0.839, T_max = 0.877	l = −14→14
13493 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0735P)² + 6.1716P] where P = (F_o² + 2F_c²)/3
2371 reflections	(Δ/σ)_max = 0.001
204 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

[Cu(NO₃)₂(C₃₂H₂₂N₄)]	V = 2685.7 (9) Å³
M_r = 650.10	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.960 (3) Å	µ = 0.88 mm⁻¹
b = 15.237 (3) Å	T = 293 K
c = 12.139 (2) Å	0.20 × 0.18 × 0.15 mm
β = 103.94 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	2371 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2181 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.877	R_int = 0.044
13493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.09	Δρ_max = 0.37 e Å⁻³
2371 reflections	Δρ_min = −0.77 e Å⁻³
204 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	1.0000	1.08431 (3)	0.7500	0.0158 (2)
N1	0.90976 (16)	1.00076 (15)	0.7873 (2)	0.0147 (5)
N2	0.79830 (16)	0.95918 (15)	0.8684 (2)	0.0127 (5)
N3	1.00584 (19)	1.19959 (17)	0.5927 (2)	0.0228 (6)
C1	0.86254 (19)	1.01906 (19)	0.8646 (2)	0.0149 (6)
H1A	0.8733	1.0684	0.9110	0.018*
C2	0.87224 (19)	0.92203 (18)	0.7368 (2)	0.0124 (6)
C3	0.89502 (19)	0.87094 (19)	0.6515 (2)	0.0144 (6)
H3A	0.9423	0.8872	0.6180	0.017*
C4	0.8443 (2)	0.79544 (19)	0.6192 (2)	0.0176 (6)
H4A	0.8587	0.7594	0.5641	0.021*
C5	0.7707 (2)	0.77168 (19)	0.6684 (3)	0.0177 (6)
H5A	0.7365	0.7217	0.6423	0.021*
C6	0.74853 (18)	0.82031 (18)	0.7533 (2)	0.0135 (6)
H6A	0.7009	0.8041	0.7862	0.016*
C7	0.80152 (19)	0.89544 (18)	0.7875 (2)	0.0119 (6)
C8	0.73918 (18)	0.96045 (18)	0.9471 (2)	0.0114 (6)
C9	0.7327 (2)	0.8866 (2)	1.0116 (3)	0.0189 (7)
H9A	0.7667	0.8365	1.0055	0.023*
C10	0.6748 (2)	0.88846 (19)	1.0852 (3)	0.0180 (6)
H10A	0.6696	0.8386	1.1273	0.022*
C11	0.62384 (18)	0.96369 (18)	1.0978 (2)	0.0113 (6)
C12	0.63268 (18)	1.03720 (18)	1.0321 (2)	0.0112 (6)
H12A	0.6000	1.0880	1.0391	0.013*
C13	0.68927 (19)	1.03586 (18)	0.9565 (2)	0.0116 (6)
H13A	0.6937	1.0850	0.9127	0.014*
C14	0.56072 (18)	0.96408 (18)	1.1761 (2)	0.0108 (6)
C15	0.52982 (19)	1.04264 (18)	1.2139 (2)	0.0129 (6)
H15A	0.5494	1.0958	1.1903	0.015*
C16	0.52938 (19)	0.88512 (19)	1.2128 (2)	0.0126 (6)
H16A	0.5478	0.8320	1.1875	0.015*
O1	1.06322 (14)	1.18409 (14)	0.68862 (19)	0.0224 (5)
O2	1.01639 (19)	1.26531 (16)	0.5384 (2)	0.0373 (6)
O3	0.94347 (17)	1.14482 (17)	0.5587 (2)	0.0352 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0152 (3)	0.0149 (3)	0.0202 (3)	0.000	0.0099 (2)	0.000
N1	0.0161 (12)	0.0147 (12)	0.0160 (12)	−0.0024 (10)	0.0092 (10)	−0.0034 (10)
N2	0.0140 (12)	0.0135 (12)	0.0132 (12)	0.0014 (9)	0.0084 (10)	−0.0008 (9)
N3	0.0290 (15)	0.0182 (14)	0.0267 (15)	0.0031 (11)	0.0172 (13)	0.0032 (12)
C1	0.0163 (14)	0.0151 (14)	0.0151 (14)	−0.0004 (11)	0.0070 (12)	−0.0004 (12)
C2	0.0091 (13)	0.0161 (14)	0.0119 (14)	−0.0013 (10)	0.0024 (11)	0.0011 (11)
C3	0.0115 (13)	0.0217 (15)	0.0117 (14)	0.0037 (11)	0.0061 (11)	0.0003 (12)
C4	0.0203 (15)	0.0170 (15)	0.0152 (15)	0.0047 (12)	0.0037 (12)	−0.0035 (12)
C5	0.0196 (15)	0.0118 (14)	0.0202 (16)	−0.0010 (12)	0.0020 (12)	−0.0021 (12)
C6	0.0097 (13)	0.0134 (13)	0.0182 (15)	0.0005 (11)	0.0050 (12)	0.0044 (11)
C7	0.0130 (13)	0.0130 (13)	0.0108 (14)	0.0031 (11)	0.0053 (11)	0.0014 (11)
C8	0.0100 (13)	0.0145 (14)	0.0127 (14)	−0.0015 (11)	0.0085 (11)	−0.0011 (11)
C9	0.0200 (16)	0.0161 (15)	0.0262 (17)	0.0077 (12)	0.0164 (13)	0.0053 (13)
C10	0.0199 (15)	0.0145 (15)	0.0239 (16)	0.0048 (12)	0.0140 (13)	0.0085 (12)
C11	0.0103 (13)	0.0148 (14)	0.0097 (13)	−0.0005 (11)	0.0040 (11)	0.0004 (11)
C12	0.0112 (13)	0.0119 (14)	0.0113 (13)	0.0003 (10)	0.0044 (11)	−0.0013 (11)
C13	0.0140 (13)	0.0118 (13)	0.0100 (13)	−0.0020 (11)	0.0048 (11)	0.0015 (11)
C14	0.0096 (13)	0.0156 (14)	0.0086 (13)	0.0006 (10)	0.0046 (11)	0.0010 (11)
C15	0.0134 (13)	0.0118 (14)	0.0156 (14)	−0.0011 (11)	0.0078 (12)	0.0019 (11)
C16	0.0142 (13)	0.0130 (14)	0.0129 (14)	0.0015 (11)	0.0080 (12)	−0.0003 (11)
O1	0.0206 (11)	0.0194 (11)	0.0294 (12)	−0.0026 (9)	0.0102 (10)	−0.0009 (9)
O2	0.0480 (16)	0.0246 (13)	0.0474 (16)	0.0038 (11)	0.0273 (13)	0.0133 (12)
O3	0.0337 (14)	0.0330 (14)	0.0357 (14)	−0.0083 (11)	0.0020 (12)	0.0044 (11)

Geometric parameters (Å, º) top

Cu1—N1	1.985 (2)	C5—C6	1.373 (4)
Cu1—N1ⁱ	1.985 (2)	C5—H5A	0.9300
Cu1—O1ⁱ	2.025 (2)	C6—C7	1.398 (4)
Cu1—O1	2.025 (2)	C6—H6A	0.9300
Cu1—O3	2.452 (3)	C8—C9	1.388 (4)
Cu1—O3ⁱ	2.452 (3)	C8—C13	1.390 (4)
N1—C1	1.333 (4)	C9—C10	1.386 (4)
N1—C2	1.401 (4)	C9—H9A	0.9300
N2—C1	1.334 (4)	C10—C11	1.406 (4)
N2—C7	1.390 (4)	C10—H10A	0.9300
N2—C8	1.450 (3)	C11—C12	1.400 (4)
N3—O2	1.230 (3)	C11—C14	1.493 (4)
N3—O3	1.246 (4)	C12—C13	1.390 (4)
N3—O1	1.291 (4)	C12—H12A	0.9300
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.401 (4)	C14—C15	1.400 (4)
C2—C7	1.406 (4)	C14—C16	1.402 (4)
C3—C4	1.382 (4)	C15—C15ⁱⁱ	1.394 (5)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.420 (4)	C16—C16ⁱⁱ	1.404 (5)
C4—H4A	0.9300	C16—H16A	0.9300

N1—Cu1—N1ⁱ	100.24 (14)	C7—C6—H6A	121.9
N1—Cu1—O1ⁱ	89.66 (9)	N2—C7—C6	131.9 (3)
N1ⁱ—Cu1—O1ⁱ	165.63 (9)	N2—C7—C2	105.4 (2)
N1—Cu1—O1	165.63 (9)	C6—C7—C2	122.6 (3)
N1ⁱ—Cu1—O1	89.66 (9)	C9—C8—C13	120.8 (3)
O1ⁱ—Cu1—O1	82.68 (12)	C9—C8—N2	119.8 (2)
C1—N1—C2	105.2 (2)	C13—C8—N2	119.4 (2)
C1—N1—Cu1	122.08 (19)	C10—C9—C8	119.1 (3)
C2—N1—Cu1	132.22 (19)	C10—C9—H9A	120.5
C1—N2—C7	107.8 (2)	C8—C9—H9A	120.5
C1—N2—C8	124.9 (2)	C9—C10—C11	121.8 (3)
C7—N2—C8	127.2 (2)	C9—C10—H10A	119.1
O2—N3—O3	123.4 (3)	C11—C10—H10A	119.1
O2—N3—O1	119.3 (3)	C12—C11—C10	117.5 (3)
O3—N3—O1	117.3 (2)	C12—C11—C14	121.4 (2)
N1—C1—N2	112.9 (3)	C10—C11—C14	121.0 (2)
N1—C1—H1A	123.5	C13—C12—C11	121.4 (3)
N2—C1—H1A	123.5	C13—C12—H12A	119.3
C3—C2—N1	131.0 (3)	C11—C12—H12A	119.3
C3—C2—C7	120.4 (3)	C8—C13—C12	119.4 (3)
N1—C2—C7	108.6 (2)	C8—C13—H13A	120.3
C4—C3—C2	117.2 (3)	C12—C13—H13A	120.3
C4—C3—H3A	121.4	C15—C14—C16	117.9 (3)
C2—C3—H3A	121.4	C15—C14—C11	121.4 (2)
C3—C4—C5	121.4 (3)	C16—C14—C11	120.7 (2)
C3—C4—H4A	119.3	C15ⁱⁱ—C15—C14	121.21 (16)
C5—C4—H4A	119.3	C15ⁱⁱ—C15—H15A	119.4
C6—C5—C4	122.0 (3)	C14—C15—H15A	119.4
C6—C5—H5A	119.0	C14—C16—C16ⁱⁱ	120.89 (16)
C4—C5—H5A	119.0	C14—C16—H16A	119.6
C5—C6—C7	116.3 (3)	C16ⁱⁱ—C16—H16A	119.6
C5—C6—H6A	121.9	N3—O1—Cu1	101.61 (16)

N1ⁱ—Cu1—N1—C1	147.7 (3)	N1—C2—C7—C6	178.1 (2)
O1ⁱ—Cu1—N1—C1	−21.8 (2)	C1—N2—C8—C9	−128.1 (3)
O1—Cu1—N1—C1	−79.4 (4)	C7—N2—C8—C9	49.3 (4)
N1ⁱ—Cu1—N1—C2	−41.6 (2)	C1—N2—C8—C13	52.2 (4)
O1ⁱ—Cu1—N1—C2	148.9 (3)	C7—N2—C8—C13	−130.4 (3)
O1—Cu1—N1—C2	91.3 (4)	C13—C8—C9—C10	0.6 (4)
C2—N1—C1—N2	0.1 (3)	N2—C8—C9—C10	−179.1 (3)
Cu1—N1—C1—N2	173.00 (18)	C8—C9—C10—C11	−1.2 (5)
C7—N2—C1—N1	−0.3 (3)	C9—C10—C11—C12	0.7 (4)
C8—N2—C1—N1	177.6 (2)	C9—C10—C11—C14	179.0 (3)
C1—N1—C2—C3	−179.0 (3)	C10—C11—C12—C13	0.4 (4)
Cu1—N1—C2—C3	9.1 (5)	C14—C11—C12—C13	−178.0 (3)
C1—N1—C2—C7	0.1 (3)	C9—C8—C13—C12	0.4 (4)
Cu1—N1—C2—C7	−171.8 (2)	N2—C8—C13—C12	−179.9 (2)
N1—C2—C3—C4	−179.9 (3)	C11—C12—C13—C8	−0.9 (4)
C7—C2—C3—C4	1.0 (4)	C12—C11—C14—C15	−19.7 (4)
C2—C3—C4—C5	1.5 (4)	C10—C11—C14—C15	161.9 (3)
C3—C4—C5—C6	−2.7 (4)	C12—C11—C14—C16	159.3 (3)
C4—C5—C6—C7	1.0 (4)	C10—C11—C14—C16	−19.0 (4)
C1—N2—C7—C6	−177.8 (3)	C16—C14—C15—C15ⁱⁱ	0.4 (5)
C8—N2—C7—C6	4.5 (5)	C11—C14—C15—C15ⁱⁱ	179.4 (3)
C1—N2—C7—C2	0.3 (3)	C15—C14—C16—C16ⁱⁱ	−1.5 (5)
C8—N2—C7—C2	−177.4 (3)	C11—C14—C16—C16ⁱⁱ	179.5 (3)
C5—C6—C7—N2	179.4 (3)	O2—N3—O1—Cu1	170.1 (2)
C5—C6—C7—C2	1.6 (4)	O3—N3—O1—Cu1	−11.7 (3)
C3—C2—C7—N2	179.0 (3)	N1—Cu1—O1—N3	−28.9 (4)
N1—C2—C7—N2	−0.2 (3)	N1ⁱ—Cu1—O1—N3	105.01 (17)
C3—C2—C7—C6	−2.7 (4)	O1ⁱ—Cu1—O1—N3	−87.19 (17)

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+1, y, −z+5/2.

Experimental details

Crystal data
Chemical formula	[Cu(NO₃)₂(C₃₂H₂₂N₄)]
M_r	650.10
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	14.960 (3), 15.237 (3), 12.139 (2)
β (°)	103.94 (3)
V (Å³)	2685.7 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.839, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	13493, 2371, 2181
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.124, 1.09
No. of reflections	2371
No. of parameters	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.77

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

Selected bond lengths (Å) top

Cu1—N1	1.985 (2)	Cu1—O3	2.452 (3)
Cu1—O1	2.025 (2)

Acknowledgements

We thank the College Research Program of Yuncheng University [2008114] for funding.

References

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