Tetra­kis(μ2-phenyl­acetato-κ2O:O′)bis­[(isoquinoline-κN)copper(II)]

Li, M.-J.; Nie, J.-J.; Xu, D.-J.

doi:10.1107/S1600536809048697

metal-organic compounds

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Volume 65| Part 12| December 2009| Page m1613

doi:10.1107/S1600536809048697

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Tetrakis(μ₂-phenylacetato-κ²O:O′)bis[(isoquinoline-κN)copper(II)]

Meng-Jiao Li,^a Jing-Jing Nie ^a and Duan-Jun Xu ^a ^*

^aDepartment of Chemistry, Zhejiang University, People's Republic of China
^*Correspondence e-mail: xudj@mail.hz.zj.cn

(Received 13 November 2009; accepted 16 November 2009; online 21 November 2009)

In the title centrosymmetric binuclear Cu^II complex, [Cu₂(C₈H₇O₂)₄(C₉H₇N)₂], the two Cu cations are bridged by four carboxylate groups of the phenylacetate anions; each Cu cation is further coordinated by an isoquinoline ligand to complete the distorted CuO₄N square-pyramidal geometry. The Cu cation is displaced by 0.2092 (8) Å from the basal plane formed by the four O atoms. Within the dinuclear molecule, the Cu⋯Cu separation is 2.6453 (6) Å. Although a parallel, overlapped arrangement of isoquinoline ligands exists in the crystal structure; the longer face-to-face distance of 3.667 (5) Å suggests there is no π–π stacking between isoquinoline ring systems.

Related literature

For general background to π–π stacking, see: Su & Xu (2004 ); Xu et al. (2007 ). For a related isoquinoline complex, see: Li et al. (2009 ). For Cu⋯Cu separations in multi-nuclear Cu^II complexes, see: Li et al. (2007 , 2009).

Experimental

Crystal data

[Cu₂(C₈H₇O₂)₄(C₉H₇N)₂]
M_r = 925.94
Triclinic, $[P \overline 1]$
a = 8.2425 (15) Å
b = 11.251 (2) Å
c = 12.121 (2) Å
α = 94.594 (2)°
β = 90.178 (2)°
γ = 104.803 (4)°
V = 1082.9 (3) Å³
Z = 1
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 294 K
0.26 × 0.22 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.835, T_max = 0.920
11731 measured reflections
3837 independent reflections
3409 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.088
S = 1.09
3837 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu—O1	1.9786 (16)
Cu—O2ⁱ	1.9754 (16)
Cu—O3	1.9785 (17)
Cu—O4ⁱ	1.9761 (17)
Cu—N1	2.1522 (18)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809048697/ng2685sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048697/ng2685Isup2.hkl

checkCIF report

Comment top

As part of our ongoing investigation on the nature of π-π stacking (Su & Xu, 2004; Xu et al., 2007), the title complex incorporating isoquinoline ligand has recently been prepared in the laboratory and its crystal structure is reported here.

The molecular structure is shown in Fig. 1. Four phenylacetate anions bridge two Cu^II cations to form the centro-symmetric complex. Within the dinuclear molecule the Cu···Cu separation of 2.6453 (6) Å is consistent with 2.646 Å found in a related binucealr Cu^II complex bridged by acetate anions (Li et al., 2009) and 2.642 Å found in a polymeric Cu^II complex bridged by thiourea (Li et al. 2007). The Cu^II cation is coordinated by four carboxyl-O atoms from phenylacetate anions in the basal plane, an isoquinoline molecule further coordinates to the Cu^II cation in the apical position to complete the distorted square-pyramidal coordination geometry; the Cu^II cation is 0.2092 (8) Å deviated from the basal coordination plane.

The parallel, overlaped arrangement of isoquinoline ligands of adjacent complexes is observed in the crystal structure (Fig. 2). The face-to-face distance of 3.667 (5) Å suggests no π-π stacking between isoquinoline ring systems in the crystal structure.

Related literature top

For general background to π–π stacking, see: Su & Xu (2004); Xu et al. (2007). For a related isoquinoline complex, see: Li et al. (2009). For Cu···Cu separations in multi-nuclear Cu^II complexes, see: Li et al. (2007, 2009).

Experimental top

Isoquinoline (0.23 ml, 2 mmol), copper dicholoride dihydrate (0.17 g, 1 mmol) and 2-phenylacetic acid (0.27 g, 2 mmol) were dissolved in ethanol (10 ml) at room temperature. The single crystals of the title compound were obtained from the solution after 2 d.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids (arbitrary spheres for H atoms) [symmetry code: (i) 1 - x, 1 - y, 1 - z].
	Fig. 2. The unit cell packing diagram showing the parallel arrangement of isoquinoline ligands. H atoms have been omitted for clarity.

Tetrakis(µ₂-phenylacetato-κ²O:O')bis[(isoquinoline- κN)copper(II)] top

Crystal data top

[Cu₂(C₈H₇O₂)₄(C₉H₇N)₂]	Z = 1
M_r = 925.94	F(000) = 478
Triclinic, P1	D_x = 1.420 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2425 (15) Å	Cell parameters from 5268 reflections
b = 11.251 (2) Å	θ = 2.0–25.0°
c = 12.121 (2) Å	µ = 1.04 mm⁻¹
α = 94.594 (2)°	T = 294 K
β = 90.178 (2)°	Prism, blue
γ = 104.803 (4)°	0.26 × 0.22 × 0.16 mm
V = 1082.9 (3) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3837 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.2°, θ_min = 1.7°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→12
T_min = 0.835, T_max = 0.920	l = −14→14
11731 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0476P)² + 0.2372P] where P = (F_o² + 2F_c²)/3
3837 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

[Cu₂(C₈H₇O₂)₄(C₉H₇N)₂]	γ = 104.803 (4)°
M_r = 925.94	V = 1082.9 (3) Å³
Triclinic, P1	Z = 1
a = 8.2425 (15) Å	Mo Kα radiation
b = 11.251 (2) Å	µ = 1.04 mm⁻¹
c = 12.121 (2) Å	T = 294 K
α = 94.594 (2)°	0.26 × 0.22 × 0.16 mm
β = 90.178 (2)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3837 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3409 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.920	R_int = 0.025
11731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.09	Δρ_max = 0.29 e Å⁻³
3837 reflections	Δρ_min = −0.20 e Å⁻³
280 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	0.44020 (3)	0.49777 (2)	0.39826 (2)	0.03660 (11)
N1	0.3604 (2)	0.47759 (17)	0.22703 (15)	0.0433 (4)
O1	0.3102 (2)	0.32991 (15)	0.42744 (15)	0.0580 (5)
O2	0.4167 (2)	0.33169 (14)	0.59722 (14)	0.0526 (4)
O3	0.6366 (2)	0.43173 (17)	0.36405 (14)	0.0546 (4)
O4	0.7375 (2)	0.43275 (17)	0.53476 (14)	0.0522 (4)
C1	0.3214 (3)	0.2823 (2)	0.5162 (2)	0.0447 (5)
C2	0.2087 (4)	0.1536 (2)	0.5287 (2)	0.0581 (7)
H2A	0.2451	0.1228	0.5945	0.070*
H2B	0.0948	0.1603	0.5403	0.070*
C3	0.2070 (3)	0.0608 (2)	0.4318 (2)	0.0446 (5)
C4	0.1314 (3)	0.0679 (2)	0.3319 (2)	0.0582 (7)
H4	0.0816	0.1321	0.3229	0.070*
C5	0.1289 (4)	−0.0202 (3)	0.2444 (3)	0.0727 (9)
H5	0.0783	−0.0143	0.1771	0.087*
C6	0.2001 (5)	−0.1151 (3)	0.2565 (3)	0.0766 (9)
H6	0.1963	−0.1746	0.1980	0.092*
C7	0.2763 (4)	−0.1229 (3)	0.3536 (3)	0.0795 (9)
H7	0.3270	−0.1868	0.3615	0.095*
C8	0.2788 (4)	−0.0355 (2)	0.4415 (2)	0.0611 (7)
H8	0.3302	−0.0422	0.5083	0.073*
C9	0.7351 (3)	0.4067 (2)	0.4323 (2)	0.0436 (5)
C10	0.8640 (3)	0.3418 (3)	0.3878 (2)	0.0595 (7)
H10A	0.9673	0.4036	0.3764	0.071*
H10B	0.8874	0.2907	0.4434	0.071*
C11	0.8137 (3)	0.2622 (2)	0.2810 (2)	0.0457 (5)
C12	0.9175 (3)	0.2738 (3)	0.1913 (2)	0.0567 (6)
H12	1.0190	0.3339	0.1960	0.068*
C13	0.8745 (4)	0.1989 (3)	0.0954 (2)	0.0694 (8)
H13	0.9471	0.2084	0.0363	0.083*
C14	0.7261 (4)	0.1106 (3)	0.0860 (3)	0.0748 (9)
H14	0.6968	0.0602	0.0206	0.090*
C15	0.6204 (4)	0.0969 (3)	0.1739 (3)	0.0755 (9)
H15	0.5194	0.0363	0.1681	0.091*
C16	0.6622 (3)	0.1718 (3)	0.2706 (2)	0.0611 (7)
H16	0.5888	0.1620	0.3293	0.073*
C21	0.3704 (3)	0.3795 (2)	0.1640 (2)	0.0500 (6)
H21	0.4125	0.3205	0.1956	0.060*
C22	0.3277 (5)	0.2486 (3)	−0.0130 (3)	0.0854 (10)
H22	0.3657	0.1877	0.0185	0.103*
C23	0.2778 (5)	0.2338 (4)	−0.1212 (3)	0.0947 (12)
H23	0.2835	0.1626	−0.1640	0.114*
C24	0.2186 (4)	0.3226 (4)	−0.1690 (2)	0.0805 (10)
H24	0.1846	0.3101	−0.2432	0.097*
C25	0.2095 (4)	0.4268 (3)	−0.1096 (2)	0.0751 (9)
H25	0.1700	0.4859	−0.1429	0.090*
C26	0.2524 (5)	0.5517 (3)	0.0722 (3)	0.0869 (11)
H26	0.2134	0.6139	0.0437	0.104*
C27	0.3021 (4)	0.5620 (3)	0.1800 (2)	0.0718 (9)
H27	0.2950	0.6322	0.2238	0.086*
C28	0.3213 (3)	0.3581 (2)	0.0513 (2)	0.0489 (6)
C29	0.2602 (3)	0.4467 (2)	0.0038 (2)	0.0536 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.03901 (17)	0.03174 (16)	0.03687 (17)	0.00689 (11)	−0.00402 (11)	−0.00272 (11)
N1	0.0469 (11)	0.0393 (10)	0.0415 (10)	0.0094 (8)	−0.0075 (8)	−0.0036 (8)
O1	0.0681 (12)	0.0368 (9)	0.0580 (11)	−0.0062 (8)	−0.0115 (9)	0.0023 (8)
O2	0.0614 (10)	0.0383 (9)	0.0497 (10)	−0.0013 (8)	−0.0008 (8)	0.0000 (7)
O3	0.0567 (10)	0.0683 (12)	0.0473 (9)	0.0337 (9)	−0.0039 (8)	−0.0028 (8)
O4	0.0468 (9)	0.0653 (11)	0.0480 (10)	0.0235 (8)	−0.0053 (7)	−0.0045 (8)
C1	0.0449 (13)	0.0322 (12)	0.0524 (14)	0.0036 (9)	0.0086 (11)	−0.0029 (10)
C2	0.0658 (17)	0.0384 (13)	0.0590 (16)	−0.0058 (12)	0.0118 (13)	−0.0005 (11)
C3	0.0421 (12)	0.0291 (11)	0.0561 (14)	−0.0025 (9)	0.0011 (10)	0.0031 (10)
C4	0.0609 (16)	0.0425 (14)	0.0711 (18)	0.0131 (12)	−0.0118 (13)	0.0048 (12)
C5	0.089 (2)	0.0604 (18)	0.0603 (18)	0.0047 (16)	−0.0197 (15)	−0.0001 (14)
C6	0.106 (3)	0.0479 (17)	0.071 (2)	0.0156 (16)	−0.0005 (18)	−0.0126 (14)
C7	0.099 (2)	0.0492 (17)	0.097 (3)	0.0351 (16)	−0.003 (2)	−0.0036 (16)
C8	0.0664 (17)	0.0503 (15)	0.0655 (17)	0.0126 (13)	−0.0117 (14)	0.0063 (13)
C9	0.0373 (12)	0.0417 (12)	0.0502 (14)	0.0092 (9)	−0.0029 (10)	−0.0028 (10)
C10	0.0443 (14)	0.0792 (19)	0.0599 (16)	0.0298 (13)	−0.0072 (12)	−0.0107 (14)
C11	0.0401 (12)	0.0482 (13)	0.0538 (14)	0.0212 (10)	0.0012 (10)	0.0025 (11)
C12	0.0448 (14)	0.0590 (16)	0.0663 (17)	0.0135 (12)	0.0083 (12)	0.0051 (13)
C13	0.076 (2)	0.079 (2)	0.0561 (17)	0.0257 (16)	0.0143 (14)	0.0014 (15)
C14	0.086 (2)	0.069 (2)	0.0677 (19)	0.0227 (17)	−0.0061 (17)	−0.0147 (16)
C15	0.0661 (19)	0.0560 (17)	0.094 (2)	0.0008 (14)	−0.0056 (17)	−0.0070 (16)
C16	0.0541 (16)	0.0623 (17)	0.0662 (17)	0.0135 (13)	0.0112 (13)	0.0056 (14)
C21	0.0524 (14)	0.0541 (15)	0.0463 (13)	0.0216 (11)	−0.0097 (11)	−0.0038 (11)
C22	0.105 (3)	0.097 (3)	0.0634 (19)	0.054 (2)	−0.0140 (17)	−0.0290 (18)
C23	0.104 (3)	0.122 (3)	0.059 (2)	0.044 (2)	−0.0057 (18)	−0.039 (2)
C24	0.079 (2)	0.115 (3)	0.0360 (15)	0.008 (2)	0.0016 (14)	−0.0062 (17)
C25	0.091 (2)	0.084 (2)	0.0436 (15)	0.0073 (17)	−0.0106 (14)	0.0131 (15)
C26	0.147 (3)	0.0507 (17)	0.070 (2)	0.0390 (19)	−0.039 (2)	0.0039 (15)
C27	0.116 (3)	0.0440 (15)	0.0592 (17)	0.0326 (16)	−0.0282 (16)	−0.0103 (13)
C28	0.0417 (13)	0.0595 (15)	0.0432 (13)	0.0121 (11)	−0.0005 (10)	−0.0062 (11)
C29	0.0570 (15)	0.0552 (15)	0.0424 (13)	0.0026 (12)	−0.0036 (11)	0.0066 (11)

Geometric parameters (Å, º) top

Cu—O1	1.9786 (16)	C10—C11	1.507 (3)
Cu—O2ⁱ	1.9754 (16)	C10—H10A	0.9700
Cu—O3	1.9785 (17)	C10—H10B	0.9700
Cu—O4ⁱ	1.9761 (17)	C11—C12	1.379 (3)
Cu—N1	2.1522 (18)	C11—C16	1.393 (3)
Cu—Cuⁱ	2.6453 (6)	C12—C13	1.369 (4)
N1—C21	1.312 (3)	C12—H12	0.9300
N1—C27	1.333 (3)	C13—C14	1.362 (4)
O1—C1	1.253 (3)	C13—H13	0.9300
O2—C1	1.255 (3)	C14—C15	1.372 (4)
O2—Cuⁱ	1.9754 (16)	C14—H14	0.9300
O3—C9	1.254 (3)	C15—C16	1.376 (4)
O4—C9	1.252 (3)	C15—H15	0.9300
O4—Cuⁱ	1.9761 (17)	C16—H16	0.9300
C1—C2	1.527 (3)	C21—C28	1.407 (3)
C2—C3	1.506 (3)	C21—H21	0.9300
C2—H2A	0.9700	C22—C23	1.358 (5)
C2—H2B	0.9700	C22—C28	1.417 (4)
C3—C8	1.373 (4)	C22—H22	0.9300
C3—C4	1.378 (4)	C23—C24	1.383 (5)
C4—C5	1.388 (4)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.345 (5)
C5—C6	1.360 (5)	C24—H24	0.9300
C5—H5	0.9300	C25—C29	1.419 (4)
C6—C7	1.352 (5)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.356 (4)
C7—C8	1.387 (4)	C26—C29	1.403 (4)
C7—H7	0.9300	C26—H26	0.9300
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.513 (3)	C28—C29	1.388 (4)

O2ⁱ—Cu—O4ⁱ	87.53 (8)	C11—C10—C9	115.1 (2)
O2ⁱ—Cu—O1	167.83 (7)	C11—C10—H10A	108.5
O4ⁱ—Cu—O1	90.12 (8)	C9—C10—H10A	108.5
O2ⁱ—Cu—O3	90.58 (8)	C11—C10—H10B	108.5
O4ⁱ—Cu—O3	167.78 (7)	C9—C10—H10B	108.5
O1—Cu—O3	89.19 (8)	H10A—C10—H10B	107.5
O2ⁱ—Cu—N1	98.20 (7)	C12—C11—C16	117.7 (2)
O4ⁱ—Cu—N1	99.69 (7)	C12—C11—C10	121.4 (2)
O1—Cu—N1	93.96 (7)	C16—C11—C10	120.9 (2)
O3—Cu—N1	92.53 (7)	C13—C12—C11	121.5 (2)
O2ⁱ—Cu—Cuⁱ	84.42 (5)	C13—C12—H12	119.2
O4ⁱ—Cu—Cuⁱ	87.03 (5)	C11—C12—H12	119.2
O1—Cu—Cuⁱ	83.53 (5)	C14—C13—C12	120.5 (3)
O3—Cu—Cuⁱ	80.77 (5)	C14—C13—H13	119.8
N1—Cu—Cuⁱ	172.85 (5)	C12—C13—H13	119.8
C21—N1—C27	117.3 (2)	C13—C14—C15	119.3 (3)
C21—N1—Cu	119.82 (16)	C13—C14—H14	120.3
C27—N1—Cu	122.90 (16)	C15—C14—H14	120.3
C1—O1—Cu	123.63 (14)	C14—C15—C16	120.7 (3)
C1—O2—Cuⁱ	122.64 (16)	C14—C15—H15	119.6
C9—O3—Cu	126.83 (16)	C16—C15—H15	119.6
C9—O4—Cuⁱ	119.64 (15)	C15—C16—C11	120.3 (3)
O1—C1—O2	125.7 (2)	C15—C16—H16	119.8
O1—C1—C2	117.9 (2)	C11—C16—H16	119.8
O2—C1—C2	116.4 (2)	N1—C21—C28	124.0 (2)
C3—C2—C1	114.8 (2)	N1—C21—H21	118.0
C3—C2—H2A	108.6	C28—C21—H21	118.0
C1—C2—H2A	108.6	C23—C22—C28	119.2 (3)
C3—C2—H2B	108.6	C23—C22—H22	120.4
C1—C2—H2B	108.6	C28—C22—H22	120.4
H2A—C2—H2B	107.5	C22—C23—C24	121.2 (3)
C8—C3—C4	117.9 (2)	C22—C23—H23	119.4
C8—C3—C2	120.5 (2)	C24—C23—H23	119.4
C4—C3—C2	121.6 (2)	C25—C24—C23	120.8 (3)
C3—C4—C5	120.4 (3)	C25—C24—H24	119.6
C3—C4—H4	119.8	C23—C24—H24	119.6
C5—C4—H4	119.8	C24—C25—C29	120.2 (3)
C6—C5—C4	120.5 (3)	C24—C25—H25	119.9
C6—C5—H5	119.8	C29—C25—H25	119.9
C4—C5—H5	119.8	C27—C26—C29	119.7 (3)
C7—C6—C5	119.9 (3)	C27—C26—H26	120.2
C7—C6—H6	120.0	C29—C26—H26	120.2
C5—C6—H6	120.0	N1—C27—C26	123.9 (3)
C6—C7—C8	119.9 (3)	N1—C27—H27	118.1
C6—C7—H7	120.0	C26—C27—H27	118.1
C8—C7—H7	120.0	C29—C28—C21	118.0 (2)
C3—C8—C7	121.3 (3)	C29—C28—C22	119.6 (2)
C3—C8—H8	119.3	C21—C28—C22	122.3 (3)
C7—C8—H8	119.3	C28—C29—C26	117.2 (2)
O4—C9—O3	125.3 (2)	C28—C29—C25	118.9 (3)
O4—C9—C10	116.9 (2)	C26—C29—C25	123.9 (3)
O3—C9—C10	117.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₈H₇O₂)₄(C₉H₇N)₂]
M_r	925.94
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.2425 (15), 11.251 (2), 12.121 (2)
α, β, γ (°)	94.594 (2), 90.178 (2), 104.803 (4)
V (Å³)	1082.9 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.26 × 0.22 × 0.16

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.835, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	11731, 3837, 3409
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.09
No. of reflections	3837
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Cu—O1	1.9786 (16)	Cu—O4ⁱ	1.9761 (17)
Cu—O2ⁱ	1.9754 (16)	Cu—N1	2.1522 (18)
Cu—O3	1.9785 (17)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by the ZIJIN project of Zhejiang University, China.

References

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