Tetra-kis(μ-4-ethyl-benzoato-κO:O')-bis-[(4-ethyl-benzoic acid-κO)copper(II)].

The molecule of the title compound, [Cu(2)(C(9)H(9)O(2))(4)(C(9)H(10)O(2))(2)], lies on a center of inversion. It consists of four bridging ethyl-benzoate ligands, forming a cage around two Cu atoms in a syn-syn configuration, and two monodentate ethyl-benzoic acid ligands bonded apically to the square-planar Cu atoms. The Cu⋯Cu distance is 2.6047 (5) Å.

Related literature

For the synthesis of aromatic carboxylic acids, see: Kaeding (1967 ▶). For tetra­kis(μ2-2-methyl­benzoato)bis­(2-methyl­benzoic acid)dicopper(II), see: Sunil et al. (2008 ▶). For tetra­kis(μ2-2-fluoro­benzoato)bis­(2-fluoro­benzoic acid)dicopper(II), see: Valach et al. (2000 ▶). For tetra­kis(μ2benzoato) bis­(2-fluoro­benzoic acid)dicopper(II), see: Kawata et al. (1992 ▶). For tetra­kis-[μ-(2-phenoxy­benzoato-O,O′)]bis­[(2-phenoxy­benzoic acid)copper(II)], see: Mak & Yip (1990 ▶).

Experimental

Crystal data

[Cu2(C9H9O2)4(C9H10O2)2]

M = 1024.07

Triclinic,

a = 10.6167 (5) Å

b = 10.7394 (7) Å

c = 10.8096 (7) Å

α = 81.848 (3)°

β = 88.594 (3)°

γ = 79.468 (2)°

V = 1199.47 (12) Å3

Z = 1

Mo Kα radiation

μ = 0.95 mm−1

T = 100 (2) K

0.54 × 0.4 × 0.39 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.628, T max = 0.708

15971 measured reflections

5683 independent reflections

4721 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.03

5683 reflections

311 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015924/fi2063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015924/fi2063Isup2.hkl

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

[Cu2(C9H9O2)4(C9H10O2)2]	Z = 1
Mr = 1024.07	F000 = 534
Triclinic, P1	Dx = 1.418 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71069 Å
a = 10.6167 (5) Å	Cell parameters from 4441 reflections
b = 10.7394 (7) Å	θ = 2.5–28.2º
c = 10.8096 (7) Å	µ = 0.95 mm−1
α = 81.848 (3)º	T = 100 (2) K
β = 88.594 (3)º	Cuboid, blue
γ = 79.468 (2)º	0.54 × 0.4 × 0.39 mm
V = 1199.47 (12) Å3

Bruker Kappa APEXII diffractometer	4721 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 100(2) K	θmax = 28º
ω and φ scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −7→14
Tmin = 0.628, Tmax = 0.708	k = −14→14
15971 measured reflections	l = −14→14
5683 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.9309P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.040	(Δ/σ)max = 0.001
wR(F2) = 0.103	Δρmax = 0.50 e Å−3
S = 1.04	Δρmin = −0.37 e Å−3
5683 reflections	Extinction correction: none
311 parameters

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 2 s/frame. A total of 1507 frames were collected with a frame width of 0.5° covering up to θ = 28.0° with 98.3% completeness accomplished.

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.

	x	y	z	Uiso*/Ueq
Cu1	0.45033 (3)	0.46672 (2)	0.90347 (2)	0.01213 (9)
O6	0.58444 (17)	0.40202 (18)	0.62540 (16)	0.0239 (4)
H6	0.599	0.4445	0.679	0.036*
O1	0.60816 (15)	0.51776 (15)	0.82165 (14)	0.0152 (3)
O3	0.36215 (15)	0.64398 (14)	0.86973 (14)	0.0166 (3)
O4	0.54987 (16)	0.29874 (15)	0.96412 (14)	0.0181 (3)
O2	0.30749 (15)	0.42705 (15)	1.01089 (14)	0.0167 (3)
O5	0.40263 (15)	0.39621 (15)	0.73471 (14)	0.0168 (3)
C51	0.4404 (2)	0.2808 (2)	0.5616 (2)	0.0144 (4)
C11	0.8123 (2)	0.58002 (19)	0.80261 (19)	0.0124 (4)
C30	0.3784 (2)	0.7244 (2)	0.94028 (19)	0.0140 (4)
C53	0.3163 (2)	0.1251 (2)	0.5207 (2)	0.0192 (5)
H53	0.2542	0.0759	0.546	0.023*
C55	0.4715 (2)	0.1870 (2)	0.3717 (2)	0.0172 (5)
H55	0.5134	0.1806	0.2957	0.021*
C52	0.3464 (2)	0.2079 (2)	0.5971 (2)	0.0172 (5)
H52	0.3038	0.215	0.6727	0.021*
C54	0.3778 (2)	0.1138 (2)	0.4054 (2)	0.0169 (5)
C36	0.2111 (2)	0.8866 (2)	0.8178 (2)	0.0171 (5)
H36	0.1956	0.823	0.773	0.02*
C16	0.9223 (2)	0.5936 (2)	0.8637 (2)	0.0145 (4)
H16	0.9212	0.5918	0.95	0.017*
C10	0.6968 (2)	0.55566 (19)	0.87604 (19)	0.0133 (4)
C31	0.3059 (2)	0.8585 (2)	0.9087 (2)	0.0143 (4)
C34	0.1628 (2)	1.1064 (2)	0.8569 (2)	0.0184 (5)
C32	0.3321 (2)	0.9558 (2)	0.9709 (2)	0.0191 (5)
H32	0.3968	0.9384	1.0306	0.023*
C56	0.5043 (2)	0.2694 (2)	0.4481 (2)	0.0162 (5)
H56	0.5682	0.3166	0.424	0.019*
C12	0.8152 (2)	0.5865 (2)	0.6725 (2)	0.0146 (4)
H12	0.743	0.5777	0.63	0.018*
C541	0.3421 (3)	0.0255 (2)	0.3213 (2)	0.0235 (5)
H54A	0.3627	−0.0618	0.3633	0.028*
H54B	0.3936	0.0313	0.2461	0.028*
C141	1.1539 (2)	0.6401 (2)	0.5944 (2)	0.0208 (5)
H14A	1.1803	0.571	0.5452	0.025*
H14B	1.2228	0.6391	0.6521	0.025*
C50	0.4725 (2)	0.3652 (2)	0.6484 (2)	0.0155 (5)
C13	0.9247 (2)	0.6059 (2)	0.6070 (2)	0.0158 (5)
H13	0.9246	0.6114	0.5203	0.019*
C15	1.0327 (2)	0.6096 (2)	0.7979 (2)	0.0164 (5)
H15	1.1059	0.6153	0.8408	0.02*
C14	1.0360 (2)	0.6173 (2)	0.6679 (2)	0.0152 (4)
C642	−0.0475 (3)	1.2359 (3)	0.9030 (3)	0.0385 (7)
H64A	−0.0923	1.1768	0.8717	0.058*
H64B	−0.0989	1.32	0.8901	0.058*
H64C	−0.0311	1.21	0.9907	0.058*
C641	0.0790 (3)	1.2371 (2)	0.8338 (2)	0.0254 (6)
H64D	0.0628	1.2612	0.7449	0.03*
H64E	0.1226	1.2997	0.8623	0.03*
C33	0.2619 (3)	1.0788 (2)	0.9443 (2)	0.0229 (5)
H33	0.2812	1.1435	0.9852	0.028*
C35	0.1394 (2)	1.0083 (2)	0.7935 (2)	0.0186 (5)
H35	0.0746	1.0253	0.7339	0.022*
C142	1.1323 (3)	0.7677 (3)	0.5072 (3)	0.0323 (6)
H14C	1.0651	0.7688	0.449	0.048*
H14D	1.2099	0.7775	0.4623	0.048*
H14E	1.1085	0.8367	0.5556	0.048*
C542	0.2016 (3)	0.0542 (2)	0.2846 (2)	0.0277 (6)
H54C	0.1498	0.0463	0.3583	0.042*
H54D	0.1855	−0.0053	0.231	0.042*
H54E	0.1807	0.1397	0.2412	0.042*

	U11	U22	U33	U12	U13	U23
Cu1	0.01076 (16)	0.01499 (14)	0.01135 (13)	−0.00383 (10)	0.00010 (10)	−0.00231 (9)
O6	0.0189 (10)	0.0369 (10)	0.0225 (9)	−0.0156 (8)	0.0057 (7)	−0.0139 (7)
O1	0.0110 (8)	0.0221 (8)	0.0148 (7)	−0.0076 (7)	0.0005 (6)	−0.0041 (6)
O3	0.0161 (9)	0.0154 (7)	0.0184 (8)	−0.0022 (6)	−0.0021 (7)	−0.0032 (6)
O4	0.0212 (9)	0.0164 (8)	0.0168 (8)	−0.0025 (7)	−0.0044 (7)	−0.0032 (6)
O2	0.0130 (8)	0.0256 (8)	0.0138 (7)	−0.0087 (7)	0.0014 (6)	−0.0036 (6)
O5	0.0144 (9)	0.0232 (8)	0.0142 (7)	−0.0042 (7)	0.0001 (6)	−0.0059 (6)
C51	0.0119 (12)	0.0176 (10)	0.0129 (10)	−0.0019 (9)	−0.0023 (8)	0.0001 (8)
C11	0.0097 (11)	0.0118 (9)	0.0152 (10)	−0.0021 (8)	−0.0009 (8)	−0.0005 (8)
C30	0.0114 (11)	0.0179 (10)	0.0130 (10)	−0.0047 (9)	0.0049 (8)	−0.0008 (8)
C53	0.0187 (13)	0.0212 (11)	0.0195 (11)	−0.0096 (10)	0.0022 (10)	−0.0010 (9)
C55	0.0149 (12)	0.0217 (11)	0.0139 (10)	0.0000 (9)	0.0025 (9)	−0.0030 (9)
C52	0.0159 (12)	0.0235 (11)	0.0126 (10)	−0.0057 (10)	0.0022 (9)	−0.0015 (9)
C54	0.0152 (12)	0.0178 (11)	0.0169 (11)	0.0007 (9)	−0.0032 (9)	−0.0041 (9)
C36	0.0165 (12)	0.0166 (10)	0.0184 (11)	−0.0035 (9)	0.0004 (9)	−0.0026 (8)
C16	0.0140 (12)	0.0171 (10)	0.0128 (10)	−0.0039 (9)	−0.0025 (9)	−0.0019 (8)
C10	0.0147 (12)	0.0124 (10)	0.0122 (9)	−0.0027 (9)	−0.0021 (8)	0.0009 (8)
C31	0.0111 (11)	0.0164 (10)	0.0155 (10)	−0.0038 (9)	0.0037 (9)	−0.0014 (8)
C34	0.0192 (13)	0.0159 (11)	0.0191 (11)	−0.0037 (9)	0.0064 (9)	0.0001 (9)
C32	0.0186 (13)	0.0215 (11)	0.0174 (11)	−0.0029 (10)	−0.0034 (9)	−0.0040 (9)
C56	0.0107 (12)	0.0200 (11)	0.0180 (11)	−0.0046 (9)	0.0013 (9)	−0.0015 (9)
C12	0.0112 (12)	0.0175 (10)	0.0161 (10)	−0.0041 (9)	−0.0022 (9)	−0.0029 (8)
C541	0.0256 (14)	0.0240 (12)	0.0239 (12)	−0.0073 (11)	0.0018 (11)	−0.0101 (10)
C141	0.0140 (12)	0.0277 (12)	0.0229 (12)	−0.0086 (10)	0.0037 (10)	−0.0059 (10)
C50	0.0142 (12)	0.0175 (10)	0.0145 (10)	−0.0032 (9)	−0.0027 (9)	−0.0008 (8)
C13	0.0145 (12)	0.0196 (11)	0.0133 (10)	−0.0033 (9)	0.0008 (9)	−0.0025 (8)
C15	0.0118 (12)	0.0185 (11)	0.0199 (11)	−0.0054 (9)	−0.0041 (9)	−0.0016 (9)
C14	0.0114 (12)	0.0131 (10)	0.0210 (11)	−0.0030 (9)	0.0021 (9)	−0.0019 (8)
C642	0.0278 (17)	0.0213 (13)	0.065 (2)	−0.0006 (12)	0.0111 (15)	−0.0078 (13)
C641	0.0290 (15)	0.0182 (11)	0.0273 (13)	−0.0024 (11)	0.0028 (11)	−0.0008 (10)
C33	0.0306 (15)	0.0184 (11)	0.0211 (12)	−0.0052 (11)	0.0008 (11)	−0.0067 (9)
C35	0.0147 (13)	0.0198 (11)	0.0202 (11)	−0.0022 (9)	−0.0024 (9)	−0.0003 (9)
C142	0.0232 (15)	0.0422 (16)	0.0296 (14)	−0.0106 (13)	−0.0002 (12)	0.0071 (12)
C542	0.0304 (16)	0.0261 (13)	0.0292 (13)	−0.0071 (11)	−0.0066 (11)	−0.0086 (10)

Cu1—O3	1.9498 (15)	C31—C32	1.392 (3)
Cu1—O4	1.9501 (16)	C34—C33	1.394 (3)
Cu1—O2	1.9593 (16)	C34—C35	1.397 (3)
Cu1—O1	2.0040 (16)	C34—C641	1.509 (3)
Cu1—O5	2.1761 (15)	C32—C33	1.387 (3)
Cu1—Cu1i	2.6047 (5)	C32—H32	0.93
O6—C50	1.326 (3)	C56—H56	0.93
O6—H6	0.82	C12—C13	1.380 (3)
O1—C10	1.277 (3)	C12—H12	0.93
O3—C30	1.267 (3)	C541—C542	1.517 (4)
O4—C30i	1.267 (3)	C541—H54A	0.97
O2—C10i	1.261 (2)	C541—H54B	0.97
O5—C50	1.223 (3)	C141—C14	1.505 (3)
C51—C52	1.392 (3)	C141—C142	1.532 (3)
C51—C56	1.397 (3)	C141—H14A	0.97
C51—C50	1.479 (3)	C141—H14B	0.97
C11—C16	1.396 (3)	C13—C14	1.400 (3)
C11—C12	1.398 (3)	C13—H13	0.93
C11—C10	1.488 (3)	C15—C14	1.396 (3)
C30—O4i	1.267 (3)	C15—H15	0.93
C30—C31	1.501 (3)	C642—C641	1.523 (4)
C53—C52	1.378 (3)	C642—H64A	0.96
C53—C54	1.403 (3)	C642—H64B	0.96
C53—H53	0.93	C642—H64C	0.96
C55—C56	1.386 (3)	C641—H64D	0.97
C55—C54	1.388 (3)	C641—H64E	0.97
C55—H55	0.93	C33—H33	0.93
C52—H52	0.93	C35—H35	0.93
C54—C541	1.505 (3)	C142—H14C	0.96
C36—C35	1.381 (3)	C142—H14D	0.96
C36—C31	1.387 (3)	C142—H14E	0.96
C36—H36	0.93	C542—H54C	0.96
C16—C15	1.382 (3)	C542—H54D	0.96
C16—H16	0.93	C542—H54E	0.96
C10—O2i	1.261 (2)
O3—Cu1—O4	169.67 (6)	C55—C56—C51	119.3 (2)
O3—Cu1—O2	89.21 (7)	C55—C56—H56	120.3
O4—Cu1—O2	89.79 (7)	C51—C56—H56	120.3
O3—Cu1—O1	89.64 (7)	C13—C12—C11	120.3 (2)
O4—Cu1—O1	89.46 (7)	C13—C12—H12	119.8
O2—Cu1—O1	169.42 (6)	C11—C12—H12	119.8
O3—Cu1—O5	100.25 (6)	C54—C541—C542	113.8 (2)
O4—Cu1—O5	90.05 (6)	C54—C541—H54A	108.8
O2—Cu1—O5	99.99 (6)	C542—C541—H54A	108.8
O1—Cu1—O5	90.57 (6)	C54—C541—H54B	108.8
O3—Cu1—Cu1i	86.32 (5)	C542—C541—H54B	108.8
O4—Cu1—Cu1i	83.36 (5)	H54A—C541—H54B	107.7
O2—Cu1—Cu1i	87.95 (5)	C14—C141—C142	112.7 (2)
O1—Cu1—Cu1i	81.48 (4)	C14—C141—H14A	109.1
O5—Cu1—Cu1i	169.69 (5)	C142—C141—H14A	109.1
C50—O6—H6	109.5	C14—C141—H14B	109.1
C10—O1—Cu1	125.79 (14)	C142—C141—H14B	109.1
C30—O3—Cu1	120.62 (14)	H14A—C141—H14B	107.8
C30i—O4—Cu1	124.01 (14)	O5—C50—O6	123.3 (2)
C10i—O2—Cu1	120.97 (15)	O5—C50—C51	122.7 (2)
C50—O5—Cu1	128.90 (15)	O6—C50—C51	113.97 (19)
C52—C51—C56	119.6 (2)	C12—C13—C14	121.5 (2)
C52—C51—C50	118.4 (2)	C12—C13—H13	119.2
C56—C51—C50	122.0 (2)	C14—C13—H13	119.2
C16—C11—C12	118.5 (2)	C16—C15—C14	120.9 (2)
C16—C11—C10	120.04 (19)	C16—C15—H15	119.5
C12—C11—C10	121.5 (2)	C14—C15—H15	119.5
O3—C30—O4i	125.7 (2)	C15—C14—C13	117.8 (2)
O3—C30—C31	117.29 (19)	C15—C14—C141	121.5 (2)
O4i—C30—C31	117.03 (19)	C13—C14—C141	120.7 (2)
C52—C53—C54	121.0 (2)	C641—C642—H64A	109.5
C52—C53—H53	119.5	C641—C642—H64B	109.5
C54—C53—H53	119.5	H64A—C642—H64B	109.5
C56—C55—C54	121.9 (2)	C641—C642—H64C	109.5
C56—C55—H55	119.1	H64A—C642—H64C	109.5
C54—C55—H55	119.1	H64B—C642—H64C	109.5
C53—C52—C51	120.3 (2)	C34—C641—C642	110.1 (2)
C53—C52—H52	119.9	C34—C641—H64D	109.6
C51—C52—H52	119.9	C642—C641—H64D	109.6
C55—C54—C53	117.9 (2)	C34—C641—H64E	109.6
C55—C54—C541	121.5 (2)	C642—C641—H64E	109.6
C53—C54—C541	120.6 (2)	H64D—C641—H64E	108.2
C35—C36—C31	120.3 (2)	C32—C33—C34	120.8 (2)
C35—C36—H36	119.8	C32—C33—H33	119.6
C31—C36—H36	119.8	C34—C33—H33	119.6
C15—C16—C11	120.9 (2)	C36—C35—C34	121.1 (2)
C15—C16—H16	119.5	C36—C35—H35	119.5
C11—C16—H16	119.5	C34—C35—H35	119.5
O2i—C10—O1	123.7 (2)	C141—C142—H14C	109.5
O2i—C10—C11	117.84 (19)	C141—C142—H14D	109.5
O1—C10—C11	118.46 (18)	H14C—C142—H14D	109.5
C36—C31—C32	119.2 (2)	C141—C142—H14E	109.5
C36—C31—C30	120.3 (2)	H14C—C142—H14E	109.5
C32—C31—C30	120.5 (2)	H14D—C142—H14E	109.5
C33—C34—C35	118.2 (2)	C541—C542—H54C	109.5
C33—C34—C641	121.5 (2)	C541—C542—H54D	109.5
C35—C34—C641	120.2 (2)	H54C—C542—H54D	109.5
C33—C32—C31	120.3 (2)	C541—C542—H54E	109.5
C33—C32—H32	119.9	H54C—C542—H54E	109.5
C31—C32—H32	119.9	H54D—C542—H54E	109.5

Table 1

Selected bond lengths (Å)

Cu1—O3	1.9498 (15)
Cu1—O4	1.9501 (16)
Cu1—O2	1.9593 (16)
Cu1—O1	2.0040 (16)
Cu1—O5	2.1761 (15)
Cu1—Cu1i	2.6047 (5)

Symmetry code: (i) .