Tetra-kis(μ(2)-phenyl-acetato-κO:O')bis-[(isoquinoline-κN)copper(II)].

In the title centrosymmetric binuclear Cu(II) complex, [Cu(2)(C(8)H(7)O(2))(4)(C(9)H(7)N)(2)], the two Cu cations are bridged by four carboxyl-ate groups of the phenyl-acetate anions; each Cu cation is further coordinated by an isoquinoline ligand to complete the distorted CuO(4)N 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 mol-ecule, 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 CuII complexes, see: Li et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

[Cu2(C8H7O2)4(C9H7N)2]

M = 925.94

Triclinic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.09

3837 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu2(C8H7O2)4(C9H7N)2]	Z = 1
Mr = 925.94	F(000) = 478
Triclinic, P1	Dx = 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

Rigaku R-AXIS RAPID IP diffractometer	3837 independent reflections
Radiation source: fine-focus sealed tube	3409 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 1.7°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→12
Tmin = 0.835, Tmax = 0.920	l = −14→14
11731 measured reflections

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(Fo2) + (0.0476P)2 + 0.2372P] where P = (Fo2 + 2Fc2)/3
3837 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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) .