Tetrakis(μ-2-chloro­benzoato-κ2O:O′)bis­[(4-vinyl­pyridine-κN)copper(II)]

Zhao, J.

doi:10.1107/S1600536808030766

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1336

doi:10.1107/S1600536808030766

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Tetrakis(μ-2-chlorobenzoato-κ²O:O′)bis[(4-vinylpyridine-κN)copper(II)]

Juan Zhao ^a ^*

^aCollege of Mechanical Engineering, Qingdao Technological University, Qingdao 266033, People's Republic of China
^*Correspondence e-mail: zhaojuanqd@163.com

(Received 19 September 2008; accepted 24 September 2008; online 27 September 2008)

The title compound, [Cu₂(C₇H₄ClO₂)₄(C₇H₇N)₂], consists of centrosymmetric dinuclear molecules with a Cu⋯Cu separation of 2.6676 (12) Å. In the molecule, four 2-chlorobenzoate anions bridge two Cu^II ions, while two neutral 4-vinylpyridine ligands coordinate them in axial positions. The Cu^II ion has a distorted square-planar pyramidal coordination, with four O atoms from the chlorobenzoate anions at the base. The N pyridine atom completes the coordination environment in the apical position.

Related literature

In the corresponding dinuclear compound [tetrakis(μ₂-acetato)bis(2-anilinopyridine)dicopper(II)] (Seco et al., 2002 ), the Cu^II has a distorted square-planar pyramidal coordination environment.

Experimental

Crystal data

[Cu₂(C₇H₄ClO₂)₄(C₇H₇N)₂]
M_r = 959.58
Monoclinic, P 2₁ /c
a = 10.251 (2) Å
b = 20.412 (4) Å
c = 10.665 (2) Å
β = 111.99 (3)°
V = 2069.2 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 297 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.677, T_max = 0.767
3708 measured reflections
3689 independent reflections
2587 reflections with I > 2σ(I)
R_int = 0.029
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.166
S = 1.00
3689 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030766/cv2452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030766/cv2452Isup2.hkl

checkCIF report

Comment top

The title compound, (I) (Fig. 1), consists of centrosymmetric dinuclear units, in which four 2-chlorobenzoato groups bridge the two copper ions and a 4-vinylpyridine neutral ligand occupies the axis position of each copper atom, coordinating them through the nitrogen atom. Each copper ion has a distorted square-planar pyramidal coordination, with four oxygen atoms in a plane. The distances for Cu—O1,O2,O3 and O4 are 1.975 (4), 1.957 (4), 1.969 (3) and 1.985 (3) Å, respectively. The fifth coordination position is occupied by the pyridine nitrogen, N, of a ligand molecule at 2.134 (4) Å. All these values agree well with those observed in [Cu₂(υ-OOCCH₃)₄(PhNHpy)₂] (PhNHpy is 2-anilinopyridine) (Seco et al., 2002). The Cu···Cu separation in (I) is 2.6473 (12) Å.

Related literature top

In the corresponding dinuclear compound [tetrakis(µ₂-acetato)bis(2-anilinopyridine)dicopper(I)] (Seco et al., 2002), the Cu^II [Cu^I according to preceding name?] has a distorted square-planar pyramidal coordination environment.

Experimental top

A solution of 4-vinylpyridine (1.05 g, 10 mmol) in alcohol (10 ml) was added to a solution of CuCl₂.2H₂O (1.70 g, 10 mmol) and 2-chlorobebziuc acid (1.56 g, 10 mmol) and KOH (0.56 g, 10 mmol) in alcohol (40 ml). The solution was stirred during 2 h and a precipitate was formed. The blue precipitate was filtered off, washed with alcohol and dried in vacuo over CaCO₃. Blue crystals were obtained from recrystallization in alcohol after a few days.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Unlabelled atoms are related with the labelled ones by symmetry operation (-x, -y, 3-z).

Tetrakis(µ-2-chlorobenzoato-κ²O:O')bis[(4-vinylpyridine- κN)copper(II)] top

Crystal data top

[Cu₂(C₇H₄ClO₂)₄(C₇H₇N)₂]	F(000) = 972
M_r = 959.58	D_x = 1.540 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.251 (2) Å	θ = 10–14°
b = 20.412 (4) Å	µ = 1.34 mm⁻¹
c = 10.665 (2) Å	T = 297 K
β = 111.99 (3)°	Block, blue
V = 2069.2 (8) Å³	0.30 × 0.30 × 0.20 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	2587 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 25.2°, θ_min = 2.0°
ω scans	h = −12→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→24
T_min = 0.677, T_max = 0.767	l = 0→12
3708 measured reflections	3 standard reflections every 100 reflections
3689 independent reflections	intensity decay: none

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1P)² + 0.5P] where P = (F_o² + 2F_c²)/3
3689 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Cu₂(C₇H₄ClO₂)₄(C₇H₇N)₂]	V = 2069.2 (8) Å³
M_r = 959.58	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.251 (2) Å	µ = 1.34 mm⁻¹
b = 20.412 (4) Å	T = 297 K
c = 10.665 (2) Å	0.30 × 0.30 × 0.20 mm
β = 111.99 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2587 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.029
T_min = 0.677, T_max = 0.767	3 standard reflections every 100 reflections
3708 measured reflections	intensity decay: none
3689 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
3689 reflections	Δρ_min = −0.57 e Å⁻³
262 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
Cu	−0.05229 (6)	0.05461 (3)	1.53164 (6)	0.0465 (2)
N1	−0.1437 (4)	0.1341 (2)	1.5999 (4)	0.0483 (9)
Cl1	0.52811 (19)	−0.03630 (12)	1.6765 (3)	0.1233 (9)
Cl2	0.2716 (2)	0.17779 (10)	1.41176 (18)	0.0975 (6)
O1	−0.2292 (4)	0.0228 (2)	1.3923 (4)	0.0691 (10)
O2	0.1417 (4)	0.0684 (2)	1.6572 (4)	0.0707 (11)
O3	−0.0022 (4)	0.09641 (17)	1.3891 (4)	0.0610 (9)
O4	−0.0849 (4)	−0.00570 (19)	1.6630 (3)	0.0634 (10)
C1	−0.4145 (9)	0.2796 (5)	1.8136 (7)	0.119 (3)
H1A	−0.4628	0.2401	1.8018	0.142*
H1B	−0.4424	0.3151	1.8522	0.142*
C2	−0.3097 (7)	0.2851 (3)	1.7770 (5)	0.0787 (18)
H2A	−0.2638	0.3253	1.7903	0.094*
C3	−0.2568 (6)	0.2323 (3)	1.7152 (5)	0.0568 (13)
C4	−0.3184 (6)	0.1719 (3)	1.6807 (5)	0.0604 (13)
H4A	−0.4007	0.1627	1.6947	0.072*
C5	−0.2598 (5)	0.1244 (3)	1.6253 (5)	0.0561 (12)
H5A	−0.3036	0.0837	1.6050	0.067*
C6	−0.0865 (5)	0.1938 (3)	1.6306 (5)	0.0604 (13)
H6A	−0.0062	0.2027	1.6126	0.072*
C7	−0.1379 (6)	0.2424 (3)	1.6864 (5)	0.0693 (15)
H7A	−0.0924	0.2827	1.7054	0.083*
C8	0.5064 (9)	0.1132 (5)	1.9717 (8)	0.125 (3)
H8A	0.5043	0.1444	2.0344	0.151*
C9	0.3825 (7)	0.0961 (4)	1.8658 (6)	0.094 (2)
H9A	0.2991	0.1173	1.8564	0.113*
C10	0.3818 (5)	0.0475 (3)	1.7737 (5)	0.0560 (13)
C11	0.5093 (6)	0.0209 (3)	1.7889 (6)	0.0678 (15)
C12	0.6323 (7)	0.0384 (4)	1.8922 (8)	0.095 (2)
H12A	0.7168	0.0189	1.8996	0.114*
C13	0.6297 (8)	0.0848 (5)	1.9844 (8)	0.114 (3)
H13A	0.7122	0.0967	2.0550	0.137*
C14	0.2409 (5)	0.0288 (3)	1.6714 (5)	0.0540 (12)
C15	0.1325 (8)	0.1677 (4)	1.0103 (8)	0.091 (2)
H15A	0.1470	0.1902	0.9408	0.109*
C16	0.2011 (7)	0.1873 (3)	1.1424 (7)	0.0791 (18)
H16A	0.2622	0.2229	1.1625	0.095*
C17	0.1783 (6)	0.1538 (3)	1.2444 (6)	0.0643 (14)
C18	0.0894 (5)	0.1012 (2)	1.2185 (5)	0.0495 (11)
C19	0.0226 (6)	0.0818 (3)	1.0849 (5)	0.0713 (15)
H19A	−0.0374	0.0458	1.0640	0.086*
C20	0.0454 (7)	0.1163 (4)	0.9819 (6)	0.091 (2)
H20A	−0.0006	0.1034	0.8924	0.109*
C21	0.0558 (5)	0.0649 (3)	1.3239 (5)	0.0488 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0445 (3)	0.0547 (4)	0.0436 (3)	0.0030 (3)	0.0201 (2)	−0.0043 (3)
N1	0.045 (2)	0.059 (2)	0.045 (2)	0.0024 (18)	0.0206 (18)	0.0000 (19)
Cl1	0.0601 (10)	0.1388 (18)	0.160 (2)	0.0017 (10)	0.0292 (12)	−0.0630 (16)
Cl2	0.0979 (12)	0.1124 (14)	0.0906 (12)	−0.0378 (11)	0.0451 (10)	−0.0404 (11)
O1	0.049 (2)	0.093 (3)	0.057 (2)	0.000 (2)	0.0117 (17)	−0.010 (2)
O2	0.053 (2)	0.076 (3)	0.075 (3)	0.0039 (19)	0.0150 (19)	−0.024 (2)
O3	0.073 (2)	0.056 (2)	0.069 (2)	0.0110 (18)	0.044 (2)	0.0070 (18)
O4	0.084 (3)	0.064 (2)	0.056 (2)	0.0137 (19)	0.041 (2)	0.0100 (18)
C1	0.120 (7)	0.134 (7)	0.104 (6)	0.044 (6)	0.044 (5)	−0.036 (5)
C2	0.094 (5)	0.082 (4)	0.049 (3)	0.026 (4)	0.014 (3)	−0.011 (3)
C3	0.063 (3)	0.063 (3)	0.040 (3)	0.013 (3)	0.014 (2)	−0.001 (2)
C4	0.056 (3)	0.069 (4)	0.062 (3)	0.008 (3)	0.030 (3)	−0.002 (3)
C5	0.060 (3)	0.052 (3)	0.060 (3)	−0.002 (2)	0.028 (3)	−0.008 (2)
C6	0.056 (3)	0.054 (3)	0.073 (4)	−0.006 (2)	0.026 (3)	−0.004 (3)
C7	0.077 (4)	0.058 (3)	0.063 (4)	−0.002 (3)	0.015 (3)	−0.011 (3)
C8	0.089 (5)	0.182 (10)	0.089 (5)	−0.022 (6)	0.015 (4)	−0.063 (6)
C9	0.061 (4)	0.140 (7)	0.073 (4)	−0.009 (4)	0.015 (3)	−0.037 (4)
C10	0.051 (3)	0.069 (4)	0.045 (3)	−0.005 (2)	0.014 (2)	0.004 (2)
C11	0.058 (3)	0.071 (4)	0.068 (4)	−0.005 (3)	0.017 (3)	0.000 (3)
C12	0.051 (3)	0.128 (6)	0.090 (5)	−0.007 (4)	0.007 (3)	−0.013 (5)
C13	0.075 (5)	0.161 (8)	0.083 (5)	−0.017 (5)	0.002 (4)	−0.030 (5)
C14	0.053 (3)	0.074 (3)	0.040 (3)	−0.007 (3)	0.023 (2)	0.000 (3)
C15	0.081 (5)	0.114 (6)	0.092 (5)	0.017 (4)	0.048 (4)	0.039 (5)
C16	0.081 (4)	0.075 (4)	0.097 (5)	−0.001 (3)	0.051 (4)	0.017 (4)
C17	0.061 (3)	0.074 (4)	0.068 (4)	0.004 (3)	0.037 (3)	0.001 (3)
C18	0.048 (3)	0.056 (3)	0.049 (3)	0.007 (2)	0.023 (2)	0.006 (2)
C19	0.066 (3)	0.096 (4)	0.047 (3)	−0.002 (3)	0.015 (3)	0.002 (3)
C20	0.085 (5)	0.131 (6)	0.051 (4)	0.010 (5)	0.017 (3)	0.021 (4)
C21	0.038 (2)	0.066 (4)	0.043 (3)	0.003 (2)	0.015 (2)	0.004 (2)

Geometric parameters (Å, º) top

Cu—O2	1.958 (4)	C7—H7A	0.9300
Cu—O3	1.971 (3)	C8—C13	1.350 (12)
Cu—O1	1.975 (4)	C8—C9	1.392 (10)
Cu—O4	1.985 (3)	C8—H8A	0.9300
Cu—N1	2.134 (4)	C9—C10	1.393 (8)
Cu—Cuⁱ	2.6676 (12)	C9—H9A	0.9300
N1—C5	1.331 (6)	C10—C11	1.368 (8)
N1—C6	1.339 (6)	C10—C14	1.497 (7)
Cl1—C11	1.735 (6)	C11—C12	1.375 (8)
Cl2—C17	1.750 (6)	C12—C13	1.372 (11)
O1—C14ⁱ	1.236 (6)	C12—H12A	0.9300
O2—C14	1.262 (6)	C13—H13A	0.9300
O3—C21	1.250 (6)	C14—O1ⁱ	1.236 (6)
O4—C21ⁱ	1.240 (6)	C15—C20	1.336 (10)
C1—C2	1.279 (10)	C15—C16	1.378 (10)
C1—H1A	0.9300	C15—H15A	0.9300
C1—H1B	0.9300	C16—C17	1.377 (8)
C2—C3	1.469 (7)	C16—H16A	0.9300
C2—H2A	0.9300	C17—C18	1.369 (7)
C3—C4	1.372 (8)	C18—C19	1.388 (7)
C3—C7	1.379 (8)	C18—C21	1.489 (6)
C4—C5	1.383 (7)	C19—C20	1.397 (8)
C4—H4A	0.9300	C19—H19A	0.9300
C5—H5A	0.9300	C20—H20A	0.9300
C6—C7	1.359 (7)	C21—O4ⁱ	1.240 (6)
C6—H6A	0.9300

O2—Cu—O3	88.52 (17)	C13—C8—C9	120.6 (8)
O2—Cu—O1	166.73 (16)	C13—C8—H8A	119.7
O3—Cu—O1	89.60 (16)	C9—C8—H8A	119.7
O2—Cu—O4	90.15 (17)	C8—C9—C10	120.9 (7)
O3—Cu—O4	166.87 (14)	C8—C9—H9A	119.6
O1—Cu—O4	88.70 (17)	C10—C9—H9A	119.6
O2—Cu—N1	96.94 (15)	C11—C10—C9	116.5 (5)
O3—Cu—N1	102.02 (14)	C11—C10—C14	127.1 (5)
O1—Cu—N1	96.30 (16)	C9—C10—C14	116.4 (5)
O4—Cu—N1	91.12 (15)	C10—C11—C12	122.7 (6)
O2—Cu—Cuⁱ	83.76 (11)	C10—C11—Cl1	122.3 (4)
O3—Cu—Cuⁱ	85.49 (10)	C12—C11—Cl1	115.0 (5)
O1—Cu—Cuⁱ	83.00 (12)	C13—C12—C11	119.7 (7)
O4—Cu—Cuⁱ	81.38 (11)	C13—C12—H12A	120.1
N1—Cu—Cuⁱ	172.47 (11)	C11—C12—H12A	120.1
C5—N1—C6	115.5 (4)	C8—C13—C12	119.5 (7)
C5—N1—Cu	119.7 (3)	C8—C13—H13A	120.2
C6—N1—Cu	124.6 (3)	C12—C13—H13A	120.2
C14ⁱ—O1—Cu	124.5 (4)	O1ⁱ—C14—O2	124.9 (5)
C14—O2—Cu	123.8 (4)	O1ⁱ—C14—C10	119.1 (5)
C21—O3—Cu	121.5 (3)	O2—C14—C10	116.0 (5)
C21ⁱ—O4—Cu	126.0 (3)	C20—C15—C16	120.2 (6)
C2—C1—H1A	120.0	C20—C15—H15A	119.9
C2—C1—H1B	120.0	C16—C15—H15A	119.9
H1A—C1—H1B	120.0	C17—C16—C15	119.4 (6)
C1—C2—C3	124.5 (8)	C17—C16—H16A	120.3
C1—C2—H2A	117.8	C15—C16—H16A	120.3
C3—C2—H2A	117.8	C18—C17—C16	121.9 (6)
C4—C3—C7	115.5 (5)	C18—C17—Cl2	119.6 (4)
C4—C3—C2	124.8 (5)	C16—C17—Cl2	118.5 (5)
C7—C3—C2	119.7 (6)	C17—C18—C19	117.8 (5)
C3—C4—C5	121.0 (5)	C17—C18—C21	124.3 (5)
C3—C4—H4A	119.5	C19—C18—C21	117.9 (5)
C5—C4—H4A	119.5	C18—C19—C20	120.0 (6)
N1—C5—C4	123.0 (5)	C18—C19—H19A	120.0
N1—C5—H5A	118.5	C20—C19—H19A	120.0
C4—C5—H5A	118.5	C15—C20—C19	120.8 (7)
N1—C6—C7	124.4 (5)	C15—C20—H20A	119.6
N1—C6—H6A	117.8	C19—C20—H20A	119.6
C7—C6—H6A	117.8	O4ⁱ—C21—O3	125.6 (4)
C6—C7—C3	120.5 (5)	O4ⁱ—C21—C18	117.1 (4)
C6—C7—H7A	119.7	O3—C21—C18	117.2 (4)
C3—C7—H7A	119.7

O2—Cu—N1—C5	−132.2 (4)	C4—C3—C7—C6	−1.5 (8)
O3—Cu—N1—C5	137.8 (4)	C2—C3—C7—C6	179.3 (5)
O1—Cu—N1—C5	46.9 (4)	C13—C8—C9—C10	2.6 (15)
O4—Cu—N1—C5	−41.9 (4)	C8—C9—C10—C11	−3.5 (11)
O3—Cu—N1—C6	−47.9 (4)	C8—C9—C10—C14	174.7 (7)
O1—Cu—N1—C6	−138.8 (4)	C9—C10—C11—C12	2.6 (9)
O4—Cu—N1—C6	132.4 (4)	C14—C10—C11—C12	−175.4 (6)
O2—Cu—O1—C14ⁱ	4.6 (10)	C9—C10—C11—Cl1	−175.9 (5)
O3—Cu—O1—C14ⁱ	86.4 (4)	C14—C10—C11—Cl1	6.1 (8)
O4—Cu—O1—C14ⁱ	−80.5 (4)	C10—C11—C12—C13	−0.5 (12)
N1—Cu—O1—C14ⁱ	−171.5 (4)	Cl1—C11—C12—C13	178.0 (7)
Cuⁱ—Cu—O1—C14ⁱ	0.9 (4)	C9—C8—C13—C12	−0.4 (16)
O3—Cu—O2—C14	−86.8 (4)	C11—C12—C13—C8	−0.6 (14)
O1—Cu—O2—C14	−4.8 (10)	Cu—O2—C14—O1ⁱ	0.8 (8)
O4—Cu—O2—C14	80.2 (4)	Cu—O2—C14—C10	−179.3 (3)
N1—Cu—O2—C14	171.3 (4)	C11—C10—C14—O1ⁱ	14.1 (8)
Cuⁱ—Cu—O2—C14	−1.1 (4)	C9—C10—C14—O1ⁱ	−163.9 (6)
O2—Cu—O3—C21	82.9 (4)	C11—C10—C14—O2	−165.8 (6)
O1—Cu—O3—C21	−84.0 (4)	C9—C10—C14—O2	16.2 (7)
O4—Cu—O3—C21	−1.4 (9)	C20—C15—C16—C17	−0.3 (11)
N1—Cu—O3—C21	179.7 (4)	C15—C16—C17—C18	0.1 (9)
Cuⁱ—Cu—O3—C21	−1.0 (4)	C15—C16—C17—Cl2	177.6 (5)
O2—Cu—O4—C21ⁱ	−84.4 (4)	C16—C17—C18—C19	0.6 (8)
O3—Cu—O4—C21ⁱ	−0.3 (10)	Cl2—C17—C18—C19	−176.9 (4)
O1—Cu—O4—C21ⁱ	82.4 (4)	C16—C17—C18—C21	−177.2 (5)
N1—Cu—O4—C21ⁱ	178.6 (4)	Cl2—C17—C18—C21	5.3 (7)
Cuⁱ—Cu—O4—C21ⁱ	−0.8 (4)	C17—C18—C19—C20	−1.0 (8)
C1—C2—C3—C4	4.6 (10)	C21—C18—C19—C20	176.9 (5)
C1—C2—C3—C7	−176.3 (7)	C16—C15—C20—C19	−0.1 (11)
C7—C3—C4—C5	2.2 (8)	C18—C19—C20—C15	0.8 (10)
C2—C3—C4—C5	−178.6 (5)	Cu—O3—C21—O4ⁱ	1.9 (7)
C6—N1—C5—C4	−0.5 (7)	Cu—O3—C21—C18	−179.9 (3)
Cu—N1—C5—C4	174.3 (4)	C17—C18—C21—O4ⁱ	−120.3 (6)
C3—C4—C5—N1	−1.3 (8)	C19—C18—C21—O4ⁱ	61.9 (6)
C5—N1—C6—C7	1.2 (8)	C17—C18—C21—O3	61.3 (7)
Cu—N1—C6—C7	−173.3 (4)	C19—C18—C21—O3	−116.5 (6)
N1—C6—C7—C3	−0.2 (9)

Symmetry code: (i) −x, −y, −z+3.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₇H₄ClO₂)₄(C₇H₇N)₂]
M_r	959.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	10.251 (2), 20.412 (4), 10.665 (2)
β (°)	111.99 (3)
V (Å³)	2069.2 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.677, 0.767
No. of measured, independent and observed [I > 2σ(I)] reflections	3708, 3689, 2587
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.166, 1.00
No. of reflections	3689
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.57

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008), WinGX (Farrugia, 1999).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20601015) and the Natural Science Foundation of Shandong Province (grant No. Y2006B12).

References

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