Tetra-μ-benzoato-bis-[(6-methyl-quino-line)-copper(II)].

In the title compound, [Cu(2)(C(7)H(5)O(2))(4)(C(10)H(9)N)(2)], the paddle-wheel-type dinuclear complex is constructed by four bridging benzoate groups and two terminal 6-methyl-quinoline ligands. The asymmetric unit contains one-half of the whole mol-ecule, and there is an inversion center at the mid-point of the Cu⋯Cu bond. The octa-hedral coordination of each Cu atom, with four O atoms in the equatorial plane, is completed by the N atom of the 6-methyl-quinoline mol-ecule [Cu-N = 2.212 (2) Å] and by another Cu atom [Cu⋯Cu = 2.6939 (13) Å]. The Cu atom lies 0.234 Å out of the plane of the four O atoms. The molecular packing is stabilized by one intramolecular C-H⋯O as well as C-H⋯π and π-π interactions.

Related literature

For related literature, see: Batten & Robson (1998 ▶); Chun et al. (2005 ▶); Cotton & Walton (1993 ▶); Janiak (2003 ▶); Lee et al. (2008 ▶); Mines et al. (2002 ▶); Pichon et al. (2007 ▶); Yoo et al. (2003 ▶).

Experimental

Crystal data

[Cu2(C7H5O2)4(C10H9N)2]

M = 897.88

Triclinic,

a = 10.420 (7) Å

b = 10.590 (7) Å

c = 10.751 (6) Å

α = 70.399 (11)°

β = 64.234 (10)°

γ = 81.107 (10)°

V = 1006.5 (11) Å3

Z = 1

Mo Kα radiation

μ = 1.12 mm−1

T = 288 (2) K

0.10 × 0.08 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS: Bruker, 1997 ▶) T min = 0.898, T max = 0.915

5579 measured reflections

3848 independent reflections

3001 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.100

S = 1.04

3848 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808016516/bx2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016516/bx2146Isup2.hkl

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

[Cu2(C7H5O2)4(C10H9N)2]	Z = 1
Mr = 897.88	F000 = 462
Triclinic, P1	Dx = 1.481 Mg m−3
a = 10.420 (7) Å	Mo Kα radiation λ = 0.71073 Å
b = 10.590 (7) Å	Cell parameters from 1441 reflections
c = 10.751 (6) Å	θ = 2.4–19.8º
α = 70.399 (11)º	µ = 1.12 mm−1
β = 64.234 (10)º	T = 288 (2) K
γ = 81.107 (10)º	Block, blue
V = 1006.5 (11) Å3	0.10 × 0.08 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	3848 independent reflections
Radiation source: fine-focus sealed tube	3001 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 288(2) K	θmax = 26.0º
phi and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS: Bruker, 1997)	h = −12→12
Tmin = 0.898, Tmax = 0.915	k = −13→10
5579 measured reflections	l = −13→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0506P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3848 reflections	Δρmax = 0.31 e Å−3
272 parameters	Δρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cu1	0.52984 (3)	0.89016 (3)	0.59215 (4)	0.03698 (14)
N1	0.6052 (2)	0.7261 (2)	0.7373 (2)	0.0381 (6)
C1	0.6560 (3)	0.7658 (3)	0.8104 (3)	0.0443 (7)
H1	0.6566	0.8574	0.7958	0.053*
C2	0.7091 (3)	0.6802 (3)	0.9084 (3)	0.0468 (8)
H2	0.7434	0.7144	0.9572	0.056*
C3	0.7097 (3)	0.5470 (3)	0.9310 (3)	0.0442 (7)
H3	0.7447	0.4885	0.9959	0.053*
C4	0.6576 (3)	0.4967 (3)	0.8567 (3)	0.0378 (7)
C5	0.6493 (3)	0.3595 (3)	0.8781 (3)	0.0449 (7)
H5	0.6834	0.2980	0.9421	0.054*
C6	0.5935 (3)	0.3131 (3)	0.8091 (3)	0.0442 (7)
C7	0.5463 (3)	0.4077 (3)	0.7091 (3)	0.0476 (8)
H7	0.5104	0.3775	0.6587	0.057*
C8	0.5519 (3)	0.5417 (3)	0.6840 (3)	0.0433 (7)
H8	0.5203	0.6016	0.6169	0.052*
C9	0.6053 (3)	0.5905 (3)	0.7591 (3)	0.0366 (6)
C10	0.5756 (4)	0.1656 (3)	0.8414 (4)	0.0595 (9)
H10A	0.6670	0.1251	0.8005	0.089*
H10B	0.5150	0.1533	0.8001	0.089*
H10C	0.5332	0.1243	0.9444	0.089*
O11	0.6763 (2)	1.01228 (19)	0.5543 (2)	0.0489 (5)
O12	0.3714 (2)	0.8060 (2)	0.5994 (2)	0.0487 (5)
C11	0.6982 (3)	1.1320 (3)	0.4734 (3)	0.0391 (7)
C12	0.8146 (3)	1.2041 (3)	0.4667 (3)	0.0383 (7)
C13	0.8366 (3)	1.3391 (3)	0.3937 (3)	0.0469 (8)
H13	0.7792	1.3862	0.3465	0.056*
C14	0.9423 (3)	1.4042 (3)	0.3903 (3)	0.0530 (8)
H14	0.9554	1.4954	0.3417	0.064*
C15	1.0290 (3)	1.3360 (3)	0.4580 (3)	0.0549 (9)
H15	1.1012	1.3805	0.4549	0.066*
C16	1.0084 (3)	1.2030 (3)	0.5295 (4)	0.0576 (9)
H16	1.0677	1.1561	0.5744	0.069*
C17	0.9012 (3)	1.1371 (3)	0.5361 (3)	0.0516 (8)
H17	0.8867	1.0465	0.5877	0.062*
O21	0.6535 (2)	0.8478 (2)	0.4116 (2)	0.0510 (6)
O22	0.3913 (2)	0.9690 (2)	0.7424 (2)	0.0487 (5)
C21	0.6732 (3)	0.9229 (3)	0.2858 (3)	0.0391 (7)
C22	0.7844 (3)	0.8779 (3)	0.1630 (3)	0.0409 (7)
C23	0.8502 (4)	0.7562 (4)	0.1888 (4)	0.0623 (10)
H23	0.8224	0.6991	0.2831	0.075*
C24	0.9574 (4)	0.7171 (4)	0.0763 (4)	0.0760 (12)
H24	1.0019	0.6341	0.0950	0.091*
C25	0.9985 (4)	0.8004 (4)	−0.0633 (4)	0.0680 (10)
H25	1.0712	0.7743	−0.1391	0.082*
C26	0.9323 (4)	0.9216 (4)	−0.0900 (4)	0.0617 (10)
H26	0.9594	0.9780	−0.1846	0.074*
C27	0.8256 (3)	0.9609 (3)	0.0223 (3)	0.0502 (8)
H27	0.7809	1.0438	0.0032	0.060*

	U11	U22	U33	U12	U13	U23
Cu1	0.0383 (2)	0.0324 (2)	0.0399 (2)	0.00153 (14)	−0.01945 (16)	−0.00685 (15)
N1	0.0415 (14)	0.0358 (14)	0.0372 (13)	0.0001 (10)	−0.0181 (11)	−0.0090 (10)
C1	0.0492 (18)	0.0365 (17)	0.0453 (18)	−0.0022 (13)	−0.0206 (15)	−0.0078 (13)
C2	0.0510 (19)	0.048 (2)	0.0507 (19)	−0.0009 (14)	−0.0295 (16)	−0.0147 (15)
C3	0.0407 (17)	0.0497 (19)	0.0418 (17)	0.0048 (14)	−0.0221 (14)	−0.0085 (14)
C4	0.0337 (16)	0.0377 (16)	0.0379 (16)	0.0021 (12)	−0.0144 (13)	−0.0079 (13)
C5	0.0423 (17)	0.0361 (17)	0.0494 (19)	0.0059 (13)	−0.0197 (15)	−0.0062 (14)
C6	0.0448 (18)	0.0392 (17)	0.0448 (18)	0.0036 (13)	−0.0168 (15)	−0.0120 (14)
C7	0.0540 (19)	0.0469 (19)	0.0497 (19)	0.0033 (15)	−0.0251 (16)	−0.0206 (15)
C8	0.0528 (19)	0.0393 (17)	0.0401 (17)	−0.0006 (14)	−0.0237 (15)	−0.0085 (13)
C9	0.0367 (16)	0.0363 (16)	0.0331 (15)	−0.0026 (12)	−0.0133 (13)	−0.0068 (12)
C10	0.073 (2)	0.0393 (19)	0.070 (2)	0.0016 (16)	−0.034 (2)	−0.0151 (16)
O11	0.0497 (13)	0.0358 (12)	0.0616 (14)	−0.0046 (9)	−0.0312 (11)	−0.0022 (10)
O12	0.0491 (13)	0.0398 (12)	0.0585 (13)	−0.0039 (10)	−0.0317 (11)	−0.0017 (10)
C11	0.0379 (16)	0.0363 (17)	0.0411 (17)	0.0006 (13)	−0.0132 (14)	−0.0137 (13)
C12	0.0350 (16)	0.0367 (16)	0.0413 (17)	0.0002 (12)	−0.0135 (13)	−0.0128 (13)
C13	0.0485 (19)	0.0387 (18)	0.0525 (19)	−0.0006 (14)	−0.0221 (16)	−0.0104 (14)
C14	0.058 (2)	0.0367 (18)	0.058 (2)	−0.0102 (15)	−0.0184 (17)	−0.0102 (15)
C15	0.0415 (19)	0.066 (2)	0.058 (2)	−0.0121 (16)	−0.0134 (16)	−0.0248 (18)
C16	0.048 (2)	0.060 (2)	0.069 (2)	−0.0029 (16)	−0.0319 (18)	−0.0124 (18)
C17	0.0471 (19)	0.0436 (19)	0.061 (2)	−0.0037 (15)	−0.0251 (17)	−0.0070 (15)
O21	0.0572 (14)	0.0438 (13)	0.0428 (13)	0.0113 (10)	−0.0182 (11)	−0.0104 (10)
O22	0.0509 (13)	0.0469 (13)	0.0484 (12)	0.0108 (10)	−0.0229 (10)	−0.0161 (10)
C21	0.0363 (16)	0.0394 (17)	0.0476 (19)	−0.0013 (13)	−0.0212 (14)	−0.0145 (14)
C22	0.0366 (16)	0.0488 (19)	0.0424 (18)	0.0003 (13)	−0.0196 (14)	−0.0158 (14)
C23	0.064 (2)	0.067 (2)	0.0436 (19)	0.0204 (18)	−0.0191 (18)	−0.0152 (17)
C24	0.070 (3)	0.082 (3)	0.068 (3)	0.037 (2)	−0.027 (2)	−0.032 (2)
C25	0.055 (2)	0.094 (3)	0.055 (2)	0.006 (2)	−0.0153 (19)	−0.036 (2)
C26	0.061 (2)	0.084 (3)	0.0413 (19)	−0.017 (2)	−0.0191 (18)	−0.0156 (18)
C27	0.053 (2)	0.053 (2)	0.050 (2)	−0.0023 (15)	−0.0265 (17)	−0.0140 (16)

Cu1—O12	1.955 (2)	C11—O12i	1.254 (3)
Cu1—O21	1.964 (2)	C11—C12	1.495 (4)
Cu1—O11	1.971 (2)	C12—C13	1.380 (4)
Cu1—O22	1.974 (2)	C12—C17	1.381 (4)
Cu1—N1	2.212 (2)	C13—C14	1.367 (4)
Cu1—Cu1i	2.6939 (13)	C13—H13	0.9300
N1—C1	1.314 (4)	C14—C15	1.373 (4)
N1—C9	1.375 (4)	C14—H14	0.9300
C1—C2	1.396 (4)	C15—C16	1.359 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.347 (4)	C16—C17	1.370 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.404 (4)	C17—H17	0.9300
C3—H3	0.9300	O21—C21	1.261 (3)
C4—C5	1.403 (4)	O22—C21i	1.250 (3)
C4—C9	1.419 (4)	C21—O22i	1.250 (3)
C5—C6	1.355 (4)	C21—C22	1.495 (4)
C5—H5	0.9300	C22—C23	1.364 (4)
C6—C7	1.410 (4)	C22—C27	1.380 (4)
C6—C10	1.505 (4)	C23—C24	1.379 (5)
C7—C8	1.358 (4)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.372 (5)
C8—C9	1.410 (4)	C24—H24	0.9300
C8—H8	0.9300	C25—C26	1.363 (5)
C10—H10A	0.9600	C25—H25	0.9300
C10—H10B	0.9600	C26—C27	1.377 (5)
C10—H10C	0.9600	C26—H26	0.9300
O11—C11	1.262 (3)	C27—H27	0.9300
O12—C11i	1.254 (3)
O12—Cu1—O21	89.07 (10)	H10A—C10—H10C	109.5
O12—Cu1—O11	166.38 (8)	H10B—C10—H10C	109.5
O21—Cu1—O11	89.52 (10)	C11—O11—Cu1	127.61 (19)
O12—Cu1—O22	88.79 (10)	C11i—O12—Cu1	121.26 (19)
O21—Cu1—O22	166.32 (8)	O12i—C11—O11	124.7 (3)
O11—Cu1—O22	89.39 (10)	O12i—C11—C12	118.4 (3)
O12—Cu1—N1	101.96 (9)	O11—C11—C12	116.9 (3)
O21—Cu1—N1	97.02 (9)	C13—C12—C17	118.5 (3)
O11—Cu1—N1	91.66 (9)	C13—C12—C11	121.1 (3)
O22—Cu1—N1	96.64 (10)	C17—C12—C11	120.4 (3)
O12—Cu1—Cu1i	86.24 (7)	C14—C13—C12	120.4 (3)
O21—Cu1—Cu1i	82.33 (7)	C14—C13—H13	119.8
O11—Cu1—Cu1i	80.14 (7)	C12—C13—H13	119.8
O22—Cu1—Cu1i	84.05 (7)	C13—C14—C15	120.6 (3)
N1—Cu1—Cu1i	171.77 (6)	C13—C14—H14	119.7
C1—N1—C9	117.2 (2)	C15—C14—H14	119.7
C1—N1—Cu1	114.60 (19)	C16—C15—C14	119.3 (3)
C9—N1—Cu1	128.17 (19)	C16—C15—H15	120.4
N1—C1—C2	124.6 (3)	C14—C15—H15	120.4
N1—C1—H1	117.7	C15—C16—C17	120.7 (3)
C2—C1—H1	117.7	C15—C16—H16	119.6
C3—C2—C1	118.8 (3)	C17—C16—H16	119.6
C3—C2—H2	120.6	C16—C17—C12	120.5 (3)
C1—C2—H2	120.6	C16—C17—H17	119.8
C2—C3—C4	120.0 (3)	C12—C17—H17	119.8
C2—C3—H3	120.0	C21—O21—Cu1	125.3 (2)
C4—C3—H3	120.0	C21i—O22—Cu1	123.10 (19)
C5—C4—C3	123.6 (3)	O22i—C21—O21	125.0 (3)
C5—C4—C9	118.7 (3)	O22i—C21—C22	118.6 (3)
C3—C4—C9	117.7 (3)	O21—C21—C22	116.4 (3)
C6—C5—C4	122.6 (3)	C23—C22—C27	119.1 (3)
C6—C5—H5	118.7	C23—C22—C21	120.4 (3)
C4—C5—H5	118.7	C27—C22—C21	120.5 (3)
C5—C6—C7	118.0 (3)	C22—C23—C24	120.6 (3)
C5—C6—C10	121.9 (3)	C22—C23—H23	119.7
C7—C6—C10	120.1 (3)	C24—C23—H23	119.7
C8—C7—C6	121.9 (3)	C25—C24—C23	120.1 (4)
C8—C7—H7	119.0	C25—C24—H24	119.9
C6—C7—H7	119.0	C23—C24—H24	119.9
C7—C8—C9	120.3 (3)	C26—C25—C24	119.6 (3)
C7—C8—H8	119.8	C26—C25—H25	120.2
C9—C8—H8	119.8	C24—C25—H25	120.2
N1—C9—C8	119.9 (2)	C25—C26—C27	120.3 (3)
N1—C9—C4	121.7 (3)	C25—C26—H26	119.9
C8—C9—C4	118.4 (3)	C27—C26—H26	119.9
C6—C10—H10A	109.5	C26—C27—C22	120.3 (3)
C6—C10—H10B	109.5	C26—C27—H27	119.8
H10A—C10—H10B	109.5	C22—C27—H27	119.8
C6—C10—H10C	109.5
O12—Cu1—N1—C1	−147.0 (2)	Cu1i—Cu1—O12—C11i	1.0 (2)
O21—Cu1—N1—C1	122.5 (2)	Cu1—O11—C11—O12i	−0.8 (4)
O11—Cu1—N1—C1	32.8 (2)	Cu1—O11—C11—C12	178.41 (18)
O22—Cu1—N1—C1	−56.8 (2)	O12i—C11—C12—C13	6.2 (4)
O12—Cu1—N1—C9	33.2 (2)	O11—C11—C12—C13	−173.0 (3)
O21—Cu1—N1—C9	−57.3 (2)	O12i—C11—C12—C17	−175.0 (3)
O11—Cu1—N1—C9	−147.0 (2)	O11—C11—C12—C17	5.7 (4)
O22—Cu1—N1—C9	123.4 (2)	C17—C12—C13—C14	0.2 (5)
C9—N1—C1—C2	−0.3 (4)	C11—C12—C13—C14	179.0 (3)
Cu1—N1—C1—C2	179.9 (2)	C12—C13—C14—C15	0.7 (5)
N1—C1—C2—C3	0.2 (5)	C13—C14—C15—C16	−0.4 (5)
C1—C2—C3—C4	0.0 (5)	C14—C15—C16—C17	−0.9 (5)
C2—C3—C4—C5	−177.4 (3)	C15—C16—C17—C12	1.8 (5)
C2—C3—C4—C9	−0.1 (4)	C13—C12—C17—C16	−1.5 (5)
C3—C4—C5—C6	177.4 (3)	C11—C12—C17—C16	179.7 (3)
C9—C4—C5—C6	0.1 (4)	O12—Cu1—O21—C21	90.1 (2)
C4—C5—C6—C7	2.0 (5)	O11—Cu1—O21—C21	−76.4 (2)
C4—C5—C6—C10	−175.4 (3)	O22—Cu1—O21—C21	9.1 (5)
C5—C6—C7—C8	−1.9 (5)	N1—Cu1—O21—C21	−168.0 (2)
C10—C6—C7—C8	175.6 (3)	Cu1i—Cu1—O21—C21	3.8 (2)
C6—C7—C8—C9	−0.3 (5)	O12—Cu1—O22—C21i	−85.7 (2)
C1—N1—C9—C8	179.9 (3)	O21—Cu1—O22—C21i	−4.6 (5)
Cu1—N1—C9—C8	−0.3 (4)	O11—Cu1—O22—C21i	80.8 (2)
C1—N1—C9—C4	0.2 (4)	N1—Cu1—O22—C21i	172.4 (2)
Cu1—N1—C9—C4	−179.98 (18)	Cu1i—Cu1—O22—C21i	0.6 (2)
C7—C8—C9—N1	−177.4 (3)	Cu1—O21—C21—O22i	−5.7 (4)
C7—C8—C9—C4	2.3 (4)	Cu1—O21—C21—C22	173.24 (18)
C5—C4—C9—N1	177.5 (2)	O22i—C21—C22—C23	−175.4 (3)
C3—C4—C9—N1	0.0 (4)	O21—C21—C22—C23	5.6 (4)
C5—C4—C9—C8	−2.2 (4)	O22i—C21—C22—C27	6.9 (4)
C3—C4—C9—C8	−179.7 (3)	O21—C21—C22—C27	−172.1 (3)
O12—Cu1—O11—C11	−1.8 (5)	C27—C22—C23—C24	0.8 (5)
O21—Cu1—O11—C11	82.3 (3)	C21—C22—C23—C24	−177.0 (3)
O22—Cu1—O11—C11	−84.1 (3)	C22—C23—C24—C25	−0.3 (6)
N1—Cu1—O11—C11	179.3 (2)	C23—C24—C25—C26	−0.3 (6)
Cu1i—Cu1—O11—C11	0.0 (2)	C24—C25—C26—C27	0.5 (6)
O21—Cu1—O12—C11i	−81.4 (2)	C25—C26—C27—C22	−0.1 (5)
O11—Cu1—O12—C11i	2.7 (5)	C23—C22—C27—C26	−0.6 (5)
O22—Cu1—O12—C11i	85.1 (2)	C21—C22—C27—C26	177.2 (3)
N1—Cu1—O12—C11i	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O11	0.93	2.50	3.047 (4)	118
C2—H2···Cg1ii	0.93	2.82	3.734 (3)	168

CgI	CgJ	CgI···CgJ	Dihedral angle	Interplanar distance	Offset
Cg2	Cg2i	3.967 (4)	0	3.39	2.06

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C22–C27 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O11	0.93	2.50	3.047 (4)	118
C2—H2⋯Cg1i	0.93	2.82	3.734 (3)	168

Symmetry code: (i) .

Table 2

π–π interactions (Å, °)

Cg2 is the centroid of ring C22–C27. The offset is defined as the distance between CgI and the perpendicular projection of CgJ on ring I.

CgI	CgJ	CgI⋯CgJ	Dihedral angle	Interplanar distance	Offset
Cg2	Cg2i	3.967 (4)		3.39	2.06

Symmetry code: (i) .