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

In the crystal structure of the title compound, [Cu(2)(CH(3)COO)(4)(C(9)H(7)N)(2)], the Cu(II) cation is coordinated by four acetate anions and one isoquinoline mol-ecule in a distorted square-pyramidal geometry; the Cu(II) cation is 0.1681 (6) Å from the basal coordination plane formed by the four O atoms. Each acetate anion bridges two Cu(II) cations to form the centrosymmetric dinuclear complex. Within the dinuclear mol-ecule, the Cu⋯Cu separation is 2.6459 (4) Å. A parallel arrangement of isoquinoline ligands of adjacent complexes is observed in the crystal structure; the face-to-face distance of 3.610 (10) Å suggests there is no π-π stacking between isoquinoline ring systems.

Related literature

For general background on the nature of π–π stacking, see: Su & Xu (2004 ▶); Xu et al. (2007 ▶). For related isoquinoline complexes, see: Clegg & Straughan (1989 ▶); Ivanikova et al. (2006 ▶). For a related quinoline complex, see: Pan & Xu (2004 ▶). For the metal atomic deviation from the basal coordination plane in square-pyramidal coordination geometry, see: Xie & Xu (2005 ▶). For the Cu⋯Cu distance in a polymeric CuII complex, see: Li et al. (2007 ▶).

Experimental

Crystal data

[Cu2(C2H3O2)4(C9H7N)2]

M = 621.57

Monoclinic,

a = 12.2278 (3) Å

b = 8.1610 (2) Å

c = 13.5309 (4) Å

β = 103.827 (8)°

V = 1311.13 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.67 mm−1

T = 294 K

0.28 × 0.26 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.635, T max = 0.720

12480 measured reflections

2997 independent reflections

2638 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.074

S = 1.06

2997 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.40 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/S1600536809025732/bq2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025732/bq2151Isup2.hkl

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

[Cu2(C2H3O2)4(C9H7N)2]	F(000) = 636
Mr = 621.57	Dx = 1.574 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10519 reflections
a = 12.2278 (3) Å	θ = 3.0–25.5°
b = 8.1610 (2) Å	µ = 1.67 mm−1
c = 13.5309 (4) Å	T = 294 K
β = 103.827 (8)°	Chunk, blue
V = 1311.13 (7) Å3	0.28 × 0.26 × 0.20 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	2997 independent reflections
Radiation source: fine-focus sealed tube	2638 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 27.4°, θmin = 3.0°
ω scans	h = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.635, Tmax = 0.720	l = −17→17
12480 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.4143P] where P = (Fo2 + 2Fc2)/3
2997 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.40 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	Occ. (<1)
Cu	0.411018 (16)	0.55776 (2)	0.528203 (14)	0.03074 (9)
N1	0.26051 (12)	0.65641 (18)	0.56603 (11)	0.0360 (3)
O1	0.32898 (12)	0.45444 (18)	0.39965 (11)	0.0457 (3)
O2	0.47861 (11)	0.35876 (18)	0.35131 (10)	0.0453 (3)
O3	0.43805 (12)	0.75437 (16)	0.45194 (11)	0.0451 (3)
O4	0.58673 (12)	0.65621 (17)	0.40330 (11)	0.0457 (3)
C1	0.16249 (15)	0.6461 (2)	0.49949 (14)	0.0378 (4)
H1	0.1593	0.5883	0.4396	0.045*
C2	−0.04146 (17)	0.7044 (3)	0.43993 (16)	0.0496 (5)
H2	−0.0450	0.6483	0.3794	0.060*
C3	−0.13598 (18)	0.7741 (3)	0.4580 (2)	0.0576 (6)
H3	−0.2040	0.7653	0.4096	0.069*
C4	−0.13180 (19)	0.8585 (3)	0.5482 (2)	0.0595 (6)
H4	−0.1972	0.9052	0.5593	0.071*
C5	−0.03322 (19)	0.8738 (3)	0.62062 (18)	0.0547 (5)
H5	−0.0318	0.9312	0.6803	0.066*
C6	0.17226 (17)	0.8114 (3)	0.67579 (15)	0.0476 (5)
H6	0.1791	0.8668	0.7370	0.057*
C7	0.26360 (16)	0.7388 (3)	0.65421 (14)	0.0428 (4)
H7	0.3320	0.7457	0.7022	0.051*
C8	0.06221 (15)	0.7172 (2)	0.51336 (14)	0.0364 (4)
C9	0.06649 (16)	0.8026 (2)	0.60497 (14)	0.0395 (4)
C10	0.37462 (16)	0.3780 (2)	0.34010 (13)	0.0365 (4)
C11	0.2983 (2)	0.3021 (3)	0.24755 (17)	0.0588 (6)
H11A	0.3428	0.2473	0.2081	0.088*	0.50
H11B	0.2540	0.3861	0.2071	0.088*	0.50
H11C	0.2493	0.2244	0.2685	0.088*	0.50
H11D	0.2213	0.3245	0.2477	0.088*	0.50
H11E	0.3101	0.1857	0.2487	0.088*	0.50
H11F	0.3148	0.3474	0.1873	0.088*	0.50
C12	0.51710 (15)	0.7661 (2)	0.40790 (13)	0.0361 (4)
C13	0.5292 (2)	0.9275 (3)	0.3568 (2)	0.0589 (6)
H13A	0.4710	1.0012	0.3656	0.088*	0.50
H13B	0.5226	0.9096	0.2855	0.088*	0.50
H13C	0.6015	0.9742	0.3869	0.088*	0.50
H13D	0.5924	0.9221	0.3264	0.088*	0.50
H13E	0.5408	1.0137	0.4065	0.088*	0.50
H13F	0.4619	0.9491	0.3051	0.088*	0.50

	U11	U22	U33	U12	U13	U23
Cu	0.02788 (12)	0.03427 (13)	0.03091 (13)	0.00155 (8)	0.00869 (8)	−0.00023 (8)
N1	0.0332 (7)	0.0399 (8)	0.0368 (7)	0.0025 (6)	0.0117 (6)	0.0014 (6)
O1	0.0362 (7)	0.0574 (9)	0.0413 (7)	−0.0006 (6)	0.0050 (6)	−0.0134 (6)
O2	0.0393 (7)	0.0568 (9)	0.0388 (7)	0.0013 (6)	0.0074 (5)	−0.0118 (6)
O3	0.0476 (8)	0.0401 (7)	0.0518 (8)	0.0056 (6)	0.0203 (6)	0.0090 (6)
O4	0.0450 (7)	0.0423 (7)	0.0554 (8)	0.0042 (6)	0.0231 (6)	0.0123 (6)
C1	0.0375 (9)	0.0428 (10)	0.0346 (9)	0.0026 (8)	0.0114 (7)	−0.0010 (7)
C2	0.0396 (10)	0.0552 (12)	0.0504 (11)	0.0017 (9)	0.0034 (9)	−0.0025 (9)
C3	0.0337 (10)	0.0629 (14)	0.0717 (15)	0.0037 (10)	0.0040 (10)	0.0051 (12)
C4	0.0389 (11)	0.0697 (15)	0.0745 (15)	0.0144 (11)	0.0224 (11)	0.0079 (12)
C5	0.0492 (12)	0.0660 (14)	0.0549 (12)	0.0133 (11)	0.0242 (10)	−0.0007 (11)
C6	0.0470 (11)	0.0602 (12)	0.0369 (9)	0.0062 (10)	0.0124 (8)	−0.0086 (9)
C7	0.0355 (9)	0.0547 (11)	0.0377 (9)	0.0015 (9)	0.0076 (7)	−0.0045 (8)
C8	0.0336 (9)	0.0371 (9)	0.0396 (9)	0.0004 (7)	0.0112 (7)	0.0056 (7)
C9	0.0376 (9)	0.0432 (10)	0.0408 (9)	0.0048 (8)	0.0152 (8)	0.0041 (8)
C10	0.0397 (9)	0.0368 (9)	0.0304 (8)	−0.0032 (8)	0.0032 (7)	0.0001 (7)
C11	0.0534 (13)	0.0723 (15)	0.0437 (11)	−0.0073 (11)	−0.0021 (9)	−0.0175 (11)
C12	0.0378 (9)	0.0343 (9)	0.0349 (8)	−0.0040 (8)	0.0059 (7)	0.0025 (7)
C13	0.0721 (16)	0.0412 (11)	0.0687 (15)	−0.0020 (10)	0.0271 (13)	0.0150 (10)

Cu—N1	2.1789 (15)	C4—H4	0.9300
Cu—O1	1.9771 (13)	C5—C9	1.412 (3)
Cu—O2i	1.9728 (13)	C5—H5	0.9300
Cu—O3	1.9777 (13)	C6—C7	1.356 (3)
Cu—O4i	1.9740 (13)	C6—C9	1.416 (3)
Cu—Cui	2.6459 (4)	C6—H6	0.9300
N1—C1	1.318 (2)	C7—H7	0.9300
N1—C7	1.362 (2)	C8—C9	1.412 (3)
O1—C10	1.251 (2)	C10—C11	1.505 (3)
O2—C10	1.254 (2)	C11—H11A	0.9600
O2—Cui	1.9728 (13)	C11—H11B	0.9600
O3—C12	1.255 (2)	C11—H11C	0.9600
O4—C12	1.249 (2)	C11—H11D	0.9600
O4—Cui	1.9740 (13)	C11—H11E	0.9600
C1—C8	1.409 (3)	C11—H11F	0.9600
C1—H1	0.9300	C12—C13	1.510 (3)
C2—C3	1.362 (3)	C13—H13A	0.9600
C2—C8	1.415 (3)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.391 (3)	C13—H13D	0.9600
C3—H3	0.9300	C13—H13E	0.9600
C4—C5	1.366 (3)	C13—H13F	0.9600
O2i—Cu—O4i	89.28 (6)	O1—C10—O2	125.47 (17)
O2i—Cu—O1	167.80 (6)	O1—C10—C11	117.25 (18)
O4i—Cu—O1	89.03 (6)	O2—C10—C11	117.28 (18)
O2i—Cu—O3	89.10 (6)	C10—C11—H11A	109.5
O4i—Cu—O3	167.77 (6)	C10—C11—H11B	109.5
O1—Cu—O3	90.00 (6)	H11A—C11—H11B	109.5
O2i—Cu—N1	97.34 (6)	C10—C11—H11C	109.5
O4i—Cu—N1	97.72 (6)	H11A—C11—H11C	109.5
O1—Cu—N1	94.86 (6)	H11B—C11—H11C	109.5
O3—Cu—N1	94.51 (6)	C10—C11—H11D	109.5
O2i—Cu—Cui	85.07 (4)	H11A—C11—H11D	141.1
O4i—Cu—Cui	84.27 (4)	H11B—C11—H11D	56.3
O1—Cu—Cui	82.74 (4)	H11C—C11—H11D	56.3
O3—Cu—Cui	83.51 (4)	C10—C11—H11E	109.5
N1—Cu—Cui	176.88 (4)	H11A—C11—H11E	56.3
C1—N1—C7	117.39 (16)	H11B—C11—H11E	141.1
C1—N1—Cu	119.81 (12)	H11C—C11—H11E	56.3
C7—N1—Cu	122.68 (12)	H11D—C11—H11E	109.5
C10—O1—Cu	124.66 (12)	C10—C11—H11F	109.5
C10—O2—Cui	122.03 (12)	H11A—C11—H11F	56.3
C12—O3—Cu	123.63 (12)	H11B—C11—H11F	56.3
C12—O4—Cui	123.05 (12)	H11C—C11—H11F	141.1
N1—C1—C8	124.11 (17)	H11D—C11—H11F	109.5
N1—C1—H1	117.9	H11E—C11—H11F	109.5
C8—C1—H1	117.9	O4—C12—O3	125.49 (17)
C3—C2—C8	119.9 (2)	O4—C12—C13	117.46 (18)
C3—C2—H2	120.0	O3—C12—C13	117.04 (18)
C8—C2—H2	120.0	C12—C13—H13A	109.5
C2—C3—C4	120.6 (2)	C12—C13—H13B	109.5
C2—C3—H3	119.7	H13A—C13—H13B	109.5
C4—C3—H3	119.7	C12—C13—H13C	109.5
C5—C4—C3	121.1 (2)	H13A—C13—H13C	109.5
C5—C4—H4	119.5	H13B—C13—H13C	109.5
C3—C4—H4	119.5	C12—C13—H13D	109.5
C4—C5—C9	120.0 (2)	H13A—C13—H13D	141.1
C4—C5—H5	120.0	H13B—C13—H13D	56.3
C9—C5—H5	120.0	H13C—C13—H13D	56.3
C7—C6—C9	119.90 (18)	C12—C13—H13E	109.5
C7—C6—H6	120.1	H13A—C13—H13E	56.3
C9—C6—H6	120.1	H13B—C13—H13E	141.1
C6—C7—N1	123.52 (17)	H13C—C13—H13E	56.3
C6—C7—H7	118.2	H13D—C13—H13E	109.5
N1—C7—H7	118.2	C12—C13—H13F	109.5
C1—C8—C9	117.99 (16)	H13A—C13—H13F	56.3
C1—C8—C2	122.54 (17)	H13B—C13—H13F	56.3
C9—C8—C2	119.46 (17)	H13C—C13—H13F	141.1
C8—C9—C5	118.87 (18)	H13D—C13—H13F	109.5
C8—C9—C6	117.09 (17)	H13E—C13—H13F	109.5
C5—C9—C6	124.04 (19)

Table 1

Selected bond lengths (Å)

Cu—N1	2.1789 (15)
Cu—O1	1.9771 (13)
Cu—O2i	1.9728 (13)
Cu—O3	1.9777 (13)
Cu—O4i	1.9740 (13)

Symmetry code: (i) .