Poly[[bis­(μ2-4,4′-bipyridine)[μ2-(2,4-dichloro­phen­oxy)acetato]copper(I)] nitrate]

Liu, S.-Z.

doi:10.1107/S1600536810002229

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m199

https://doi.org/10.1107/S1600536810002229

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Poly[[bis(μ₂-4,4′-bipyridine)[μ₂-(2,4-dichlorophenoxy)acetato]copper(I)] nitrate]

Shi-Zhu Liu ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510631, People's Republic of China
^*Correspondence e-mail: liushizhu521@126.com

(Received 17 December 2009; accepted 18 January 2010; online 23 January 2010)

The title compound, {[Cu₂(C₈H₅Cl₂O₃)(C₁₀H₈N₂)₂]NO₃}_n was prepared by reacting copper(II) nitrate with 4,4′-bipyridine (4,4′-bipy) and (2,4-dichlorophenoxy)acetic acid under solvothermal conditions. Each of two copper(I) atoms in the asymmetric unit is three-coordinated by two N atoms from two 4,4′-bipy ligands and one O atom from the (2,4-dichlorophenoxy)acetate ligand. As both ligands act as bridging ligands, a double-stranded chain structure is observed.

Related literature

For coordination polymers incorporating either 4,4′bipy or phenoxyacetato ligands and Cu(I) or Cu(II), see: Biswas et al. (2007 ); Bourne & Moitsheki (2007 ); Huang et al. (2008 ); Mo et al. (2009 ); Smith et al. (1981 ).

Experimental

Crystal data

[Cu₂(C₈H₅Cl₂O₃)(C₁₀H₈N₂)₂]NO₃
M_r = 721.5
Monoclinic, P 2₁ /c
a = 10.598 (2) Å
b = 18.552 (3) Å
c = 15.212 (3) Å
β = 108.835 (2)°
V = 2830.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.74 mm⁻¹
T = 296 K
0.15 × 0.13 × 0.08 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.883, T_max = 0.935
14129 measured reflections
5085 independent reflections
3787 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.143
S = 1.04
5085 reflections
388 parameters
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810002229/im2172sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002229/im2172Isup2.hkl

checkCIF report

Comment top

The design and synthesis of inorganic-organic composite coordination polymers exhibiting novel structures and properties is an intensively studied field of chemical research. 4,4'-bipyridine is a ligand that is particularly suited for constructing frameworks that possess hydrophobic pores and channels with potentially useful inclusion properties, including size and shape specificity (Bourne & Moitsheki, 2007; Huang et al., 2008; Mo et al., 2009; Biswas et al., 2007). 2,4-Dichlorophenoxyacetato ligands have been described to act as bridging in ligands in a typical Cu(II) paddlewheel complex (Smith et al., 1981).

The title compound (Fig. 1) was prepared from copper(II) nitrate, 4,4'-bipyridine (4,4'-bipy) and 2,4-dichlorophenoxyacetic acid under solvothermal conditions with ethanol most probably acting as the reducing agent for copper(II). A rufous colored block shaped crystal of the resulting copper(I) complex with a 2,4-dichlorophenoxyacetato ligand was characterized by single-crystal X-ray analysis. It reveals that each of two copper(I) centers is three-coordinated by two N atoms from two 4,4'-bipy ligands and one O atom from a bridging 2,4-dichlorophenoxyacetato ligand. The copper(I) coordination units are additionally connected by bridging 4,4'-bipy ligands, generating a one-dimensional polymeric chain strurcture (Fig. 2). A doubly stranded chain is observed due to the coordination of the copper(I) centers to one 2,4-dichlorophenoxyacetato ligand.

Related literature top

Forcoordination polymers incorporating either 4,4'bipy or phenoxyacetato ligands and Cu(I) or Cu(II), see: Biswas et al. (2007); Bourne & Moitsheki (2007); Huang et al. (2008); Mo et al. (2009); Smith et al. (1981).

Experimental top

A mixture of Cu(NO₃)₂ × 5 H₂O (0.121 g, 0.44 mmol), 4,4'-bipyridine × 2 H₂O (0.096 g, 0.5 mmol) and 2,4-dichlorophenoxyacetic acid (0.22 g, 1 mmol) in 8 ml of an ethanol/H₂O mixture (v/v 1/7) was stirred vigorously for 10 min and then sealed in a 25 ml teflon-lined stainless-steel autoclave. The autoclave was heated to 403 K for 2 days and was then slowly cooled to room temperature with a rate of 6 K/h. The product was collected by filtration, washed with water and air-dried. Rufous block shaped crystals suitable for X-ray analysis were obtained in ca 26.8% yield based on Cu.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing displacement ellipsoids at 50% probability for non-H atoms. Symmetry code: i 1 + x, 0.5 - y, 1/2 + z.
	Fig. 2. A view of the one-dimensional polymeric chain structure of the title compound. Hydrogen atoms are omitted for clarity.

Poly[[bis(µ₂-4,4'-bipyridine)[µ₂-(2,4-dichlorophenoxy)acetato]copper(I)] nitrate] top

Crystal data top

[Cu₂(C₈H₅Cl₂O₃)(C₁₀H₈N₂)₂]NO₃	F(000) = 1456
M_r = 721.5	D_x = 1.693 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5085 reflections
a = 10.598 (2) Å	θ = 1.8–25.2°
b = 18.552 (3) Å	µ = 1.74 mm⁻¹
c = 15.212 (3) Å	T = 296 K
β = 108.835 (2)°	Block, rufous
V = 2830.9 (8) Å³	0.15 × 0.13 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5085 independent reflections
Radiation source: fine-focus sealed tube	3787 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scan	θ_max = 25.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.883, T_max = 0.935	k = −19→22
14129 measured reflections	l = −16→18

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.068P)² + 4.0523P] where P = (F_o² + 2F_c²)/3
5085 reflections	(Δ/σ)_max = 0.001
388 parameters	Δρ_max = 0.89 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[Cu₂(C₈H₅Cl₂O₃)(C₁₀H₈N₂)₂]NO₃	V = 2830.9 (8) Å³
M_r = 721.5	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.598 (2) Å	µ = 1.74 mm⁻¹
b = 18.552 (3) Å	T = 296 K
c = 15.212 (3) Å	0.15 × 0.13 × 0.08 mm
β = 108.835 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	5085 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3787 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.935	R_int = 0.032
14129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.04	Δρ_max = 0.89 e Å⁻³
5085 reflections	Δρ_min = −0.68 e Å⁻³
388 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	0.29363 (5)	0.27588 (3)	1.15749 (4)	0.04390 (19)
Cu2	0.48636 (5)	0.28270 (3)	1.03403 (4)	0.04604 (19)
N3	0.3225 (3)	0.2599 (2)	0.9378 (3)	0.0444 (9)
C22	0.0663 (4)	0.2425 (2)	0.8069 (3)	0.0394 (9)
C13	−0.0770 (4)	0.1880 (2)	1.0032 (3)	0.0499 (12)
H13	−0.1148	0.1422	0.9928	0.060*
C5	0.1398 (5)	0.5119 (2)	1.2023 (4)	0.0498 (11)
C12	−0.1511 (4)	0.2477 (2)	0.9594 (3)	0.0380 (9)
C24	0.2591 (4)	0.3141 (3)	0.8824 (3)	0.0466 (11)
H24	0.3019	0.3584	0.8882	0.056*
C10	0.0413 (4)	0.3181 (2)	1.0374 (3)	0.0451 (11)
H10	0.0815	0.3632	1.0486	0.054*
C11	−0.0874 (4)	0.3135 (2)	0.9796 (3)	0.0441 (10)
H11	−0.1327	0.3553	0.9535	0.053*
C14	0.0513 (4)	0.1966 (2)	1.0613 (3)	0.0495 (12)
H14	0.0979	0.1559	1.0900	0.059*
C20	0.2591 (5)	0.1964 (3)	0.9247 (4)	0.0559 (13)
H20	0.3024	0.1571	0.9596	0.067*
C21	0.1331 (4)	0.1861 (3)	0.8623 (3)	0.0513 (12)
H21	0.0928	0.1411	0.8575	0.062*
C4	0.2570 (5)	0.5161 (2)	1.1810 (4)	0.0558 (13)
C3	0.3775 (6)	0.5171 (3)	1.2524 (5)	0.0752 (17)
H3	0.4569	0.5201	1.2390	0.090*
C7	0.3548 (5)	0.5004 (3)	1.0594 (4)	0.0619 (14)
H7A	0.4340	0.5263	1.0956	0.074*
H7B	0.3364	0.5135	0.9947	0.074*
C9	0.2614 (9)	0.5098 (3)	1.3627 (4)	0.086 (2)
C6	0.1390 (6)	0.5089 (3)	1.2928 (4)	0.0682 (15)
H6	0.0596	0.5063	1.3063	0.082*
C2	0.3796 (8)	0.5138 (3)	1.3432 (5)	0.091 (2)
H2	0.4604	0.5143	1.3913	0.110*
N1	0.1127 (3)	0.26020 (19)	1.0789 (2)	0.0387 (8)
C8	0.3819 (4)	0.4199 (2)	1.0702 (3)	0.0429 (10)
O2	0.3150 (3)	0.38364 (16)	1.1069 (2)	0.0532 (8)
O1	0.2440 (3)	0.52203 (18)	1.0888 (3)	0.0606 (9)
Cl2	−0.01198 (13)	0.51063 (8)	1.11418 (11)	0.0687 (4)
Cl1	0.2599 (3)	0.50305 (12)	1.47790 (13)	0.1398 (10)
O3	0.4707 (3)	0.39830 (17)	1.0396 (2)	0.0554 (9)
N6	0.2506 (5)	0.4773 (4)	0.7132 (5)	0.0851 (16)
C23	0.1347 (4)	0.3077 (2)	0.8176 (3)	0.0455 (10)
H23	0.0960	0.3470	0.7808	0.055*
C25	−0.0720 (4)	0.2359 (2)	0.7422 (3)	0.0376 (9)
C15	−0.2888 (4)	0.2414 (2)	0.8933 (3)	0.0357 (9)
C26	−0.1299 (4)	0.1708 (2)	0.7098 (3)	0.0484 (11)
H26	−0.0817	0.1284	0.7282	0.058*
C19	−0.3701 (4)	0.3011 (2)	0.8646 (3)	0.0473 (11)
H19	−0.3415	0.3458	0.8915	0.057*
C16	−0.3419 (4)	0.1766 (2)	0.8556 (3)	0.0469 (11)
H16	−0.2936	0.1343	0.8746	0.056*
C29	−0.1522 (4)	0.2960 (2)	0.7132 (4)	0.0563 (13)
H29	−0.1193	0.3414	0.7348	0.068*
C18	−0.4926 (4)	0.2953 (2)	0.7970 (3)	0.0475 (11)
H18	−0.5433	0.3368	0.7779	0.057*
C17	−0.4666 (4)	0.1739 (2)	0.7894 (3)	0.0505 (12)
H17	−0.5002	0.1292	0.7657	0.061*
C27	−0.2593 (4)	0.1678 (2)	0.6498 (3)	0.0512 (12)
H27	−0.2959	0.1229	0.6292	0.061*
C28	−0.2795 (5)	0.2893 (2)	0.6530 (4)	0.0547 (13)
H28	−0.3299	0.3309	0.6343	0.066*
N2	−0.5420 (3)	0.23224 (18)	0.7575 (2)	0.0386 (8)
N4	−0.3348 (3)	0.22657 (18)	0.6199 (3)	0.0413 (8)
O6	0.2775 (8)	0.4203 (3)	0.6898 (5)	0.161 (3)
O5	0.1538 (8)	0.5055 (6)	0.6659 (6)	0.229 (5)
O4	0.3168 (8)	0.5019 (6)	0.7763 (9)	0.282 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0233 (3)	0.0560 (4)	0.0418 (3)	−0.0006 (2)	−0.0041 (2)	0.0028 (2)
Cu2	0.0269 (3)	0.0546 (4)	0.0474 (4)	0.0019 (2)	−0.0008 (2)	−0.0023 (3)
N3	0.0290 (18)	0.051 (2)	0.048 (2)	0.0013 (16)	0.0043 (16)	−0.0036 (18)
C22	0.028 (2)	0.047 (2)	0.039 (2)	−0.0007 (18)	0.0044 (18)	−0.0066 (19)
C13	0.037 (2)	0.040 (2)	0.059 (3)	−0.0082 (19)	−0.003 (2)	0.013 (2)
C5	0.056 (3)	0.036 (2)	0.057 (3)	0.007 (2)	0.017 (2)	0.003 (2)
C12	0.026 (2)	0.046 (2)	0.037 (2)	−0.0006 (17)	0.0030 (17)	0.0049 (19)
C24	0.032 (2)	0.052 (3)	0.050 (3)	−0.0088 (19)	0.005 (2)	−0.002 (2)
C10	0.028 (2)	0.045 (2)	0.052 (3)	−0.0045 (18)	−0.0022 (19)	0.000 (2)
C11	0.032 (2)	0.042 (2)	0.049 (3)	0.0026 (18)	0.0001 (19)	0.005 (2)
C14	0.032 (2)	0.046 (3)	0.058 (3)	0.0006 (19)	−0.003 (2)	0.017 (2)
C20	0.040 (2)	0.045 (3)	0.067 (3)	0.004 (2)	−0.004 (2)	−0.004 (2)
C21	0.035 (2)	0.046 (3)	0.058 (3)	0.0014 (19)	−0.005 (2)	−0.004 (2)
C4	0.056 (3)	0.036 (2)	0.069 (4)	0.011 (2)	0.012 (3)	0.007 (2)
C3	0.068 (4)	0.049 (3)	0.093 (5)	0.008 (3)	0.004 (3)	−0.003 (3)
C7	0.051 (3)	0.049 (3)	0.095 (4)	0.011 (2)	0.035 (3)	0.021 (3)
C9	0.142 (7)	0.045 (3)	0.061 (4)	0.021 (4)	0.022 (4)	−0.003 (3)
C6	0.091 (4)	0.041 (3)	0.072 (4)	0.014 (3)	0.026 (3)	0.004 (3)
C2	0.095 (5)	0.063 (4)	0.084 (5)	0.016 (4)	−0.015 (4)	−0.015 (3)
N1	0.0260 (17)	0.048 (2)	0.0352 (19)	−0.0029 (15)	0.0003 (14)	0.0045 (16)
C8	0.026 (2)	0.042 (2)	0.051 (3)	−0.0041 (18)	−0.0012 (19)	0.007 (2)
O2	0.0466 (18)	0.0451 (18)	0.060 (2)	−0.0064 (14)	0.0066 (16)	0.0104 (15)
O1	0.0492 (19)	0.058 (2)	0.079 (3)	0.0196 (16)	0.0269 (18)	0.0207 (18)
Cl2	0.0513 (7)	0.0733 (9)	0.0809 (10)	0.0034 (6)	0.0205 (7)	0.0069 (7)
Cl1	0.233 (3)	0.1117 (16)	0.0609 (11)	0.0612 (17)	0.0279 (14)	−0.0073 (10)
O3	0.0343 (16)	0.0523 (19)	0.074 (2)	0.0030 (14)	0.0096 (16)	0.0018 (16)
N6	0.046 (3)	0.090 (4)	0.106 (5)	−0.011 (3)	0.006 (3)	−0.018 (4)
C23	0.034 (2)	0.049 (3)	0.046 (3)	−0.0027 (19)	0.0027 (19)	0.003 (2)
C25	0.030 (2)	0.044 (2)	0.037 (2)	−0.0019 (17)	0.0077 (18)	−0.0073 (18)
C15	0.0248 (19)	0.046 (2)	0.030 (2)	−0.0039 (17)	0.0005 (16)	0.0009 (18)
C26	0.033 (2)	0.039 (2)	0.063 (3)	0.0032 (18)	0.000 (2)	−0.003 (2)
C19	0.030 (2)	0.043 (2)	0.056 (3)	−0.0005 (18)	−0.003 (2)	−0.006 (2)
C16	0.035 (2)	0.040 (2)	0.049 (3)	0.0053 (18)	−0.010 (2)	0.001 (2)
C29	0.039 (2)	0.037 (2)	0.076 (4)	−0.0040 (19)	−0.006 (2)	−0.005 (2)
C18	0.031 (2)	0.044 (3)	0.057 (3)	0.0054 (18)	0.000 (2)	0.000 (2)
C17	0.042 (2)	0.043 (3)	0.050 (3)	−0.0029 (19)	−0.007 (2)	−0.005 (2)
C27	0.036 (2)	0.045 (3)	0.062 (3)	−0.005 (2)	0.001 (2)	−0.008 (2)
C28	0.041 (3)	0.042 (3)	0.068 (3)	0.003 (2)	−0.001 (2)	0.001 (2)
N2	0.0247 (16)	0.046 (2)	0.0380 (19)	0.0022 (14)	0.0003 (15)	−0.0057 (16)
N4	0.0308 (18)	0.045 (2)	0.042 (2)	−0.0016 (15)	0.0043 (16)	−0.0007 (16)
O6	0.190 (7)	0.083 (4)	0.160 (6)	−0.010 (4)	−0.012 (5)	−0.011 (4)
O5	0.125 (6)	0.424 (16)	0.139 (7)	0.105 (8)	0.045 (5)	−0.002 (8)
O4	0.106 (6)	0.324 (14)	0.378 (15)	−0.042 (7)	0.023 (7)	−0.232 (12)

Geometric parameters (Å, º) top

Cu1—N2ⁱ	1.913 (3)	C7—H7A	0.9700
Cu1—N1	1.926 (3)	C7—H7B	0.9700
Cu1—O2	2.180 (3)	C9—C2	1.379 (10)
Cu2—N3	1.922 (4)	C9—C6	1.387 (9)
Cu2—N4ⁱ	1.931 (3)	C9—Cl1	1.762 (7)
Cu2—O3	2.155 (3)	C6—H6	0.9300
N3—C20	1.339 (6)	C2—H2	0.9300
N3—C24	1.344 (6)	C8—O2	1.235 (5)
C22—C21	1.387 (6)	C8—O3	1.243 (5)
C22—C23	1.393 (6)	N6—O4	1.088 (9)
C22—C25	1.483 (5)	N6—O5	1.169 (8)
C13—C14	1.372 (6)	N6—O6	1.181 (8)
C13—C12	1.397 (6)	C23—H23	0.9300
C13—H13	0.9300	C25—C26	1.374 (6)
C5—C6	1.380 (7)	C25—C29	1.385 (6)
C5—C4	1.383 (7)	C15—C16	1.373 (6)
C5—Cl2	1.730 (5)	C15—C19	1.384 (6)
C12—C11	1.381 (6)	C26—C27	1.381 (6)
C12—C15	1.486 (5)	C26—H26	0.9300
C24—C23	1.373 (6)	C19—C18	1.376 (6)
C24—H24	0.9300	C19—H19	0.9300
C10—N1	1.348 (5)	C16—C17	1.379 (6)
C10—C11	1.366 (5)	C16—H16	0.9300
C10—H10	0.9300	C29—C28	1.370 (6)
C11—H11	0.9300	C29—H29	0.9300
C14—N1	1.332 (6)	C18—N2	1.341 (5)
C14—H14	0.9300	C18—H18	0.9300
C20—C21	1.380 (6)	C17—N2	1.339 (5)
C20—H20	0.9300	C17—H17	0.9300
C21—H21	0.9300	C27—N4	1.342 (6)
C4—O1	1.368 (6)	C27—H27	0.9300
C4—C3	1.384 (8)	C28—N4	1.326 (6)
C3—C2	1.376 (10)	C28—H28	0.9300
C3—H3	0.9300	N2—Cu1ⁱⁱ	1.913 (3)
C7—O1	1.443 (6)	N4—Cu2ⁱⁱ	1.931 (3)
C7—C8	1.519 (6)

N2ⁱ—Cu1—N1	161.82 (15)	C9—C6—H6	121.3
N2ⁱ—Cu1—O2	100.44 (13)	C3—C2—C9	119.8 (6)
N1—Cu1—O2	96.62 (13)	C3—C2—H2	120.1
N3—Cu2—N4ⁱ	160.65 (15)	C9—C2—H2	120.1
N3—Cu2—O3	100.74 (14)	C14—N1—C10	116.6 (3)
N4ⁱ—Cu2—O3	97.66 (13)	C14—N1—Cu1	125.6 (3)
C20—N3—C24	116.1 (4)	C10—N1—Cu1	117.8 (3)
C20—N3—Cu2	126.3 (3)	O2—C8—O3	127.5 (4)
C24—N3—Cu2	117.4 (3)	O2—C8—C7	118.0 (4)
C21—C22—C23	116.1 (4)	O3—C8—C7	114.6 (4)
C21—C22—C25	122.9 (4)	C8—O2—Cu1	143.1 (3)
C23—C22—C25	120.9 (4)	C4—O1—C7	118.3 (4)
C14—C13—C12	120.2 (4)	C8—O3—Cu2	114.4 (3)
C14—C13—H13	119.9	O4—N6—O5	123.0 (10)
C12—C13—H13	119.9	O4—N6—O6	119.4 (8)
C6—C5—C4	122.1 (5)	O5—N6—O6	117.6 (8)
C6—C5—Cl2	117.9 (4)	C24—C23—C22	120.1 (4)
C4—C5—Cl2	120.0 (4)	C24—C23—H23	119.9
C11—C12—C13	115.9 (4)	C22—C23—H23	119.9
C11—C12—C15	121.5 (4)	C26—C25—C29	115.9 (4)
C13—C12—C15	122.6 (4)	C26—C25—C22	122.8 (4)
N3—C24—C23	123.8 (4)	C29—C25—C22	121.2 (4)
N3—C24—H24	118.1	C16—C15—C19	116.1 (4)
C23—C24—H24	118.1	C16—C15—C12	122.2 (4)
N1—C10—C11	123.0 (4)	C19—C15—C12	121.7 (4)
N1—C10—H10	118.5	C25—C26—C27	120.4 (4)
C11—C10—H10	118.5	C25—C26—H26	119.8
C10—C11—C12	120.8 (4)	C27—C26—H26	119.8
C10—C11—H11	119.6	C18—C19—C15	120.9 (4)
C12—C11—H11	119.6	C18—C19—H19	119.6
N1—C14—C13	123.4 (4)	C15—C19—H19	119.6
N1—C14—H14	118.3	C15—C16—C17	120.2 (4)
C13—C14—H14	118.3	C15—C16—H16	119.9
N3—C20—C21	123.5 (4)	C17—C16—H16	119.9
N3—C20—H20	118.2	C28—C29—C25	120.6 (4)
C21—C20—H20	118.2	C28—C29—H29	119.7
C20—C21—C22	120.3 (4)	C25—C29—H29	119.7
C20—C21—H21	119.8	N2—C18—C19	122.8 (4)
C22—C21—H21	119.8	N2—C18—H18	118.6
O1—C4—C5	116.4 (4)	C19—C18—H18	118.6
O1—C4—C3	124.4 (5)	N2—C17—C16	123.7 (4)
C5—C4—C3	119.2 (6)	N2—C17—H17	118.1
C2—C3—C4	119.9 (7)	C16—C17—H17	118.1
C2—C3—H3	120.0	N4—C27—C26	123.2 (4)
C4—C3—H3	120.0	N4—C27—H27	118.4
O1—C7—C8	112.6 (4)	C26—C27—H27	118.4
O1—C7—H7A	109.1	N4—C28—C29	123.6 (4)
C8—C7—H7A	109.1	N4—C28—H28	118.2
O1—C7—H7B	109.1	C29—C28—H28	118.2
C8—C7—H7B	109.1	C17—N2—C18	116.1 (4)
H7A—C7—H7B	107.8	C17—N2—Cu1ⁱⁱ	120.6 (3)
C2—C9—C6	121.7 (6)	C18—N2—Cu1ⁱⁱ	123.3 (3)
C2—C9—Cl1	121.2 (6)	C28—N4—C27	116.2 (4)
C6—C9—Cl1	117.1 (6)	C28—N4—Cu2ⁱⁱ	123.5 (3)
C5—C6—C9	117.3 (6)	C27—N4—Cu2ⁱⁱ	120.3 (3)
C5—C6—H6	121.3

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₈H₅Cl₂O₃)(C₁₀H₈N₂)₂]NO₃
M_r	721.5
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.598 (2), 18.552 (3), 15.212 (3)
β (°)	108.835 (2)
V (Å³)	2830.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.74
Crystal size (mm)	0.15 × 0.13 × 0.08

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.883, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	14129, 5085, 3787
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.143, 1.04
No. of reflections	5085
No. of parameters	388
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.68

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors acknowledge South China Normal University for supporting this work.

References

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