Bis(μ-biphenyl-2,2'-dicarboxyl-ato)bis-[(2,2'-bipyridine)copper(II)].

The title compound, [Cu(2)(C(14)H(8)O(4))(2)(C(10)H(8)N(2))(2)], is a centrosymmetric binuclear copper(II) complex, with a Cu⋯Cu separation of 6.136 (16) Å. The Cu atom displays a cis-CuN(2)O(2) square-planar geometry, although two long (> 2.43 Å) Cu⋯O contacts complete a distorted cis-CuN(2)O(4) octa-hedron. Extensive C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For related literature, see: Bu et al. (2004 ▶); He et al. (2007 ▶); Huang et al. (2004 ▶); Long et al. (2001 ▶); Ma et al. (2003 ▶); Rao et al. (2004 ▶); Yaghi et al. (2003 ▶); Yang et al. (2002 ▶); Zhang et al. (2004 ▶); Zhu et al. (2001 ▶); He & Zhu (2003 ▶).

Experimental

Crystal data

[Cu2(C14H8O4)2(C10H8N2)2]

M = 1839.75

Monoclinic,

a = 11.234 (2) Å

b = 13.336 (3) Å

c = 15.431 (6) Å

β = 122.16 (2)°

V = 1957.1 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.15 mm−1

T = 293 (2) K

0.40 × 0.26 × 0.23 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.708, T max = 0.771

18687 measured reflections

4472 independent reflections

3708 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.118

S = 1.03

4472 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.60 e Å−3

Data collection: SMART (Siemens, 1994 ▶); cell refinement: SAINT (Siemens, 1994 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802583X/om2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802583X/om2255Isup2.hkl

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

[Cu2(C14H8O4)2(C10H8N2)2]	F000 = 940
Mr = 1839.75	Dx = 1.561 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19150 reflections
a = 11.234 (2) Å	θ = 3.1–27.4º
b = 13.336 (3) Å	µ = 1.15 mm−1
c = 15.431 (6) Å	T = 293 (2) K
β = 122.16 (2)º	Block, blue
V = 1957.1 (9) Å3	0.40 × 0.26 × 0.23 mm
Z = 2

Siemens SMART CCD area-detector diffractometer	4472 independent reflections
Radiation source: fine-focus sealed tube	3708 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.046
T = 293(2) K	θmax = 27.4º
ω scans	θmin = 3.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.708, Tmax = 0.771	k = −17→17
18687 measured reflections	l = −18→19

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
4472 reflections	Δρmax = 0.29 e Å−3
280 parameters	Δρmin = −0.60 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	0.63909 (3)	−0.160660 (19)	−0.059678 (18)	0.02914 (12)
O1	0.70349 (16)	−0.04363 (11)	0.03157 (11)	0.0354 (4)
O2	0.8638 (2)	−0.16096 (12)	0.10287 (15)	0.0530 (5)
O3	0.62962 (19)	0.15631 (14)	0.16045 (14)	0.0480 (5)
O4	0.47467 (16)	0.21452 (12)	0.00754 (11)	0.0374 (4)
N1	0.68794 (18)	−0.10223 (14)	−0.15551 (13)	0.0320 (4)
N2	0.63566 (18)	−0.28542 (14)	−0.13069 (14)	0.0331 (4)
C1	0.7186 (2)	−0.00573 (19)	−0.15928 (18)	0.0406 (5)
H1A	0.7227	0.0390	−0.1115	0.049*
C2	0.7441 (3)	0.0289 (2)	−0.2320 (2)	0.0504 (7)
H2A	0.7664	0.0959	−0.2327	0.060*
C3	0.7361 (3)	−0.0368 (2)	−0.3032 (2)	0.0531 (7)
H3A	0.7514	−0.0145	−0.3536	0.064*
C4	0.7051 (3)	−0.1367 (2)	−0.29961 (19)	0.0462 (6)
H4A	0.7002	−0.1823	−0.3470	0.055*
C5	0.6486 (3)	−0.3529 (2)	−0.2682 (2)	0.0487 (7)
H5A	0.6566	−0.3429	−0.3246	0.058*
C6	0.6319 (3)	−0.4472 (2)	−0.2420 (3)	0.0585 (8)
H6A	0.6296	−0.5022	−0.2800	0.070*
C7	0.6184 (3)	−0.4608 (2)	−0.1591 (2)	0.0540 (7)
H7A	0.6097	−0.5248	−0.1392	0.065*
C8	0.6181 (3)	−0.37789 (19)	−0.1068 (2)	0.0444 (6)
H8A	0.6053	−0.3865	−0.0525	0.053*
C9	0.6815 (2)	−0.16746 (17)	−0.22479 (17)	0.0332 (5)
C10	0.6534 (2)	−0.27237 (17)	−0.20994 (17)	0.0337 (5)
C11	0.8922 (2)	0.08967 (16)	0.20040 (15)	0.0278 (4)
C12	0.8946 (2)	−0.01519 (16)	0.20175 (15)	0.0281 (4)
C13	0.9639 (2)	−0.06631 (17)	0.29523 (16)	0.0346 (5)
H13A	0.9681	−0.1360	0.2959	0.042*
C14	1.0260 (2)	−0.0142 (2)	0.38647 (16)	0.0405 (5)
H14A	1.0703	−0.0486	0.4484	0.049*
C15	1.0221 (2)	0.0895 (2)	0.38529 (17)	0.0419 (6)
H15A	1.0636	0.1249	0.4466	0.050*
C16	0.9568 (2)	0.14064 (17)	0.29350 (18)	0.0365 (5)
H16A	0.9559	0.2104	0.2937	0.044*
C17	0.8383 (2)	0.14901 (14)	0.10351 (17)	0.0282 (4)
C18	0.7102 (2)	0.19898 (15)	0.04996 (16)	0.0292 (4)
C19	0.6773 (2)	0.25507 (18)	−0.03716 (18)	0.0369 (5)
H19A	0.5920	0.2890	−0.0727	0.044*
C20	0.7682 (3)	0.26123 (18)	−0.07140 (19)	0.0412 (5)
H20A	0.7446	0.2991	−0.1290	0.049*
C21	0.8951 (2)	0.21017 (18)	−0.01881 (19)	0.0400 (5)
H21A	0.9573	0.2131	−0.0412	0.048*
C22	0.9287 (3)	0.15476 (17)	0.06719 (19)	0.0366 (5)
H22A	1.0137	0.1204	0.1018	0.044*
C23	0.8187 (2)	−0.07766 (15)	0.10614 (16)	0.0300 (4)
C24	0.5999 (2)	0.18908 (16)	0.07706 (17)	0.0309 (4)

	U11	U22	U33	U12	U13	U23
Cu1	0.03431 (18)	0.02951 (18)	0.02666 (17)	−0.00125 (10)	0.01828 (13)	−0.00287 (9)
O1	0.0386 (8)	0.0330 (8)	0.0287 (8)	0.0015 (7)	0.0138 (7)	−0.0053 (6)
O2	0.0586 (12)	0.0359 (10)	0.0433 (10)	0.0155 (8)	0.0128 (9)	−0.0077 (7)
O3	0.0446 (10)	0.0630 (12)	0.0467 (11)	0.0160 (8)	0.0313 (9)	0.0260 (8)
O4	0.0328 (8)	0.0494 (10)	0.0328 (8)	0.0021 (7)	0.0193 (7)	0.0047 (7)
N1	0.0321 (9)	0.0371 (10)	0.0286 (9)	−0.0026 (8)	0.0174 (8)	−0.0026 (8)
N2	0.0323 (9)	0.0339 (10)	0.0325 (9)	0.0008 (8)	0.0168 (8)	−0.0031 (8)
C1	0.0441 (13)	0.0396 (13)	0.0410 (13)	−0.0049 (11)	0.0247 (11)	0.0004 (10)
C2	0.0523 (15)	0.0506 (16)	0.0521 (16)	−0.0115 (13)	0.0304 (13)	0.0044 (12)
C3	0.0485 (15)	0.075 (2)	0.0423 (14)	−0.0104 (14)	0.0288 (12)	0.0046 (13)
C4	0.0412 (13)	0.0684 (17)	0.0339 (12)	−0.0086 (12)	0.0233 (11)	−0.0095 (12)
C5	0.0477 (15)	0.0549 (17)	0.0515 (16)	−0.0021 (12)	0.0317 (13)	−0.0170 (12)
C6	0.0578 (17)	0.0476 (16)	0.074 (2)	−0.0064 (13)	0.0380 (16)	−0.0293 (15)
C7	0.0522 (16)	0.0322 (13)	0.076 (2)	−0.0053 (12)	0.0327 (15)	−0.0113 (12)
C8	0.0475 (14)	0.0354 (13)	0.0500 (15)	−0.0028 (11)	0.0259 (12)	−0.0028 (11)
C9	0.0253 (10)	0.0467 (13)	0.0273 (11)	−0.0003 (9)	0.0138 (9)	−0.0040 (9)
C10	0.0268 (10)	0.0414 (13)	0.0313 (11)	−0.0001 (9)	0.0144 (9)	−0.0076 (9)
C11	0.0261 (9)	0.0282 (10)	0.0298 (10)	0.0002 (8)	0.0154 (8)	−0.0003 (8)
C12	0.0282 (10)	0.0304 (11)	0.0269 (10)	0.0008 (8)	0.0154 (8)	0.0001 (8)
C13	0.0383 (12)	0.0330 (11)	0.0337 (11)	0.0039 (9)	0.0199 (10)	0.0056 (9)
C14	0.0416 (13)	0.0515 (14)	0.0261 (11)	0.0053 (11)	0.0166 (10)	0.0062 (10)
C15	0.0418 (12)	0.0521 (15)	0.0258 (11)	0.0020 (11)	0.0139 (10)	−0.0096 (10)
C16	0.0386 (12)	0.0322 (11)	0.0365 (12)	0.0003 (9)	0.0184 (10)	−0.0055 (9)
C17	0.0328 (11)	0.0243 (10)	0.0302 (11)	−0.0037 (8)	0.0186 (9)	−0.0015 (8)
C18	0.0345 (11)	0.0242 (10)	0.0320 (11)	−0.0024 (9)	0.0198 (9)	0.0004 (8)
C19	0.0403 (12)	0.0332 (12)	0.0382 (12)	0.0040 (10)	0.0215 (10)	0.0099 (10)
C20	0.0530 (14)	0.0362 (12)	0.0422 (13)	−0.0049 (11)	0.0305 (11)	0.0083 (10)
C21	0.0462 (13)	0.0398 (13)	0.0487 (14)	−0.0066 (11)	0.0352 (12)	0.0014 (11)
C22	0.0339 (12)	0.0389 (13)	0.0394 (13)	−0.0010 (9)	0.0211 (10)	0.0007 (9)
C23	0.0357 (11)	0.0280 (11)	0.0294 (10)	−0.0010 (9)	0.0194 (9)	−0.0010 (8)
C24	0.0346 (11)	0.0257 (10)	0.0360 (11)	0.0013 (9)	0.0211 (9)	0.0030 (9)

Cu1—O1	1.9640 (15)	C6—H6A	0.9300
Cu1—O4i	1.9725 (16)	C7—C8	1.370 (4)
Cu1—N2	1.9814 (19)	C7—H7A	0.9300
Cu1—N1	1.9897 (19)	C8—H8A	0.9300
Cu1—O2	2.434 (2)	C9—C10	1.479 (3)
Cu1—C23	2.519 (2)	C11—C16	1.394 (3)
Cu1—O3i	2.557 (2)	C11—C12	1.399 (3)
Cu1—C24i	2.580 (2)	C11—C17	1.505 (3)
O1—C23	1.273 (2)	C12—C13	1.399 (3)
O2—C23	1.233 (3)	C12—C23	1.503 (3)
O3—C24	1.225 (3)	C13—C14	1.381 (3)
O3—Cu1i	2.5567 (19)	C13—H13A	0.9300
O4—C24	1.280 (3)	C14—C15	1.383 (4)
O4—Cu1i	1.9725 (16)	C14—H14A	0.9300
N1—C1	1.342 (3)	C15—C16	1.380 (3)
N1—C9	1.350 (3)	C15—H15A	0.9300
N2—C8	1.331 (3)	C16—H16A	0.9300
N2—C10	1.351 (3)	C17—C18	1.390 (3)
C1—C2	1.377 (3)	C17—C22	1.399 (3)
C1—H1A	0.9300	C18—C19	1.405 (3)
C2—C3	1.372 (4)	C18—C24	1.509 (3)
C2—H2A	0.9300	C19—C20	1.379 (3)
C3—C4	1.385 (4)	C19—H19A	0.9300
C3—H3A	0.9300	C20—C21	1.387 (3)
C4—C9	1.377 (3)	C20—H20A	0.9300
C4—H4A	0.9300	C21—C22	1.384 (3)
C5—C6	1.365 (4)	C21—H21A	0.9300
C5—C10	1.383 (3)	C22—H22A	0.9300
C5—H5A	0.9300	C24—Cu1i	2.580 (2)
C6—C7	1.378 (5)
O1—Cu1—O4i	93.92 (7)	C6—C7—H7A	120.8
O1—Cu1—N2	162.77 (7)	N2—C8—C7	122.5 (3)
O4i—Cu1—N2	95.38 (8)	N2—C8—H8A	118.8
O1—Cu1—N1	94.56 (7)	C7—C8—H8A	118.8
O4i—Cu1—N1	160.15 (7)	N1—C9—C4	121.3 (2)
N2—Cu1—N1	81.35 (8)	N1—C9—C10	114.4 (2)
O1—Cu1—O2	58.55 (6)	C4—C9—C10	124.3 (2)
O4i—Cu1—O2	96.94 (8)	N2—C10—C5	121.0 (2)
N2—Cu1—O2	105.83 (7)	N2—C10—C9	114.12 (19)
N1—Cu1—O2	102.80 (8)	C5—C10—C9	124.9 (2)
O1—Cu1—C23	29.83 (6)	C16—C11—C12	118.49 (19)
O4i—Cu1—C23	95.07 (7)	C16—C11—C17	118.75 (19)
N2—Cu1—C23	134.42 (7)	C12—C11—C17	122.34 (18)
N1—Cu1—C23	101.19 (7)	C11—C12—C13	119.90 (19)
O2—Cu1—C23	28.76 (6)	C11—C12—C23	122.91 (18)
O1—Cu1—O3i	106.45 (7)	C13—C12—C23	117.11 (19)
O4i—Cu1—O3i	56.28 (6)	C14—C13—C12	120.5 (2)
N2—Cu1—O3i	90.78 (7)	C14—C13—H13A	119.7
N1—Cu1—O3i	104.04 (7)	C12—C13—H13A	119.7
O2—Cu1—O3i	150.22 (7)	C13—C14—C15	119.7 (2)
C23—Cu1—O3i	130.98 (7)	C13—C14—H14A	120.2
O1—Cu1—C24i	99.04 (7)	C15—C14—H14A	120.2
O4i—Cu1—C24i	28.92 (6)	C16—C15—C14	120.2 (2)
N2—Cu1—C24i	96.11 (7)	C16—C15—H15A	119.9
N1—Cu1—C24i	131.58 (7)	C14—C15—H15A	119.9
O2—Cu1—C24i	123.91 (8)	C15—C16—C11	121.2 (2)
C23—Cu1—C24i	113.37 (7)	C15—C16—H16A	119.4
O3i—Cu1—C24i	27.59 (6)	C11—C16—H16A	119.4
C23—O1—Cu1	100.02 (13)	C18—C17—C22	118.57 (19)
C23—O2—Cu1	79.48 (13)	C18—C17—C11	125.76 (19)
C24—O3—Cu1i	77.28 (13)	C22—C17—C11	115.66 (19)
C24—O4—Cu1i	102.92 (13)	C17—C18—C19	119.05 (19)
C1—N1—C9	119.4 (2)	C17—C18—C24	122.42 (19)
C1—N1—Cu1	125.93 (16)	C19—C18—C24	118.37 (19)
C9—N1—Cu1	114.61 (15)	C20—C19—C18	121.8 (2)
C8—N2—C10	119.0 (2)	C20—C19—H19A	119.1
C8—N2—Cu1	125.93 (17)	C18—C19—H19A	119.1
C10—N2—Cu1	115.06 (15)	C19—C20—C21	119.1 (2)
N1—C1—C2	121.8 (2)	C19—C20—H20A	120.4
N1—C1—H1A	119.1	C21—C20—H20A	120.4
C2—C1—H1A	119.1	C22—C21—C20	119.6 (2)
C3—C2—C1	119.0 (3)	C22—C21—H21A	120.2
C3—C2—H2A	120.5	C20—C21—H21A	120.2
C1—C2—H2A	120.5	C21—C22—C17	121.9 (2)
C2—C3—C4	119.5 (2)	C21—C22—H22A	119.1
C2—C3—H3A	120.2	C17—C22—H22A	119.1
C4—C3—H3A	120.2	O2—C23—O1	121.8 (2)
C9—C4—C3	119.0 (2)	O2—C23—C12	120.6 (2)
C9—C4—H4A	120.5	O1—C23—C12	117.53 (18)
C3—C4—H4A	120.5	O2—C23—Cu1	71.76 (13)
C6—C5—C10	119.1 (3)	O1—C23—Cu1	50.14 (10)
C6—C5—H5A	120.4	C12—C23—Cu1	165.85 (15)
C10—C5—H5A	120.4	O3—C24—O4	122.5 (2)
C5—C6—C7	119.8 (2)	O3—C24—C18	121.2 (2)
C5—C6—H6A	120.1	O4—C24—C18	116.28 (18)
C7—C6—H6A	120.1	O3—C24—Cu1i	75.13 (13)
C8—C7—C6	118.5 (3)	O4—C24—Cu1i	48.16 (10)
C8—C7—H7A	120.8	C18—C24—Cu1i	161.10 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1	0.93	2.58	3.081 (3)	114
C4—H4A···O4ii	0.93	2.59	3.378 (3)	143
C5—H5A···O4ii	0.93	2.51	3.304 (4)	144
C6—H6A···O3iii	0.93	2.25	3.162 (3)	166
C16—H16A···O2iv	0.93	2.48	3.192 (3)	133
C19—H19A···O4	0.93	2.45	2.761 (3)	100

Cu1—O1	1.9640 (15)
Cu1—O4i	1.9725 (16)
Cu1—N2	1.9814 (19)
Cu1—N1	1.9897 (19)
Cu1—O2	2.434 (2)
Cu1—O3i	2.557 (2)

O1—Cu1—O4i	93.92 (7)
O1—Cu1—N2	162.77 (7)
O4i—Cu1—N2	95.38 (8)
O1—Cu1—N1	94.56 (7)
O4i—Cu1—N1	160.15 (7)
N2—Cu1—N1	81.35 (8)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1	0.93	2.58	3.081 (3)	114
C4—H4A⋯O4ii	0.93	2.59	3.378 (3)	143
C5—H5A⋯O4ii	0.93	2.51	3.304 (4)	144
C6—H6A⋯O3iii	0.93	2.25	3.162 (3)	166
C16—H16A⋯O2iv	0.93	2.48	3.192 (3)	133
C19—H19A⋯O4	0.93	2.45	2.761 (3)	100

Symmetry codes: (ii) ; (iii) ; (iv) .