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)], was obtained by solvothermal synthesis. The Cu(II) atom is coordinated by one chelating 2,2'-bipyridine ligand and two carboxyl groups from different biphenyl-2,2'-dicarboxyl-ate ligands, leading to a distorted octahedral environment. Each carboxyl-ate group makes one short Cu-O bond [1.9608 (14) and 1.9701 (14) Å] and one longer Cu-O contact [2.4338 (17) and 2.5541 (17) Å] to each Cu(II) atom. The biphenyl-2,2'-dicarboxyl-ate ligands bridge between Cu(II) atoms, forming a dinuclear complex around a crystallographic inversion centre.

Related literature

For complexes of biphenyl-2,2′-dicarboxylic acid, a good candidate for the construction of metal–organic frameworks, see: Rueff et al. (2003 ▶); Xu et al. (2006 ▶); An & Niu (2008 ▶).

Experimental

Crystal data

[Cu2(C14H8O4)2(C10H8N2)2]

M = 919.86

Monoclinic,

a = 11.220 (2) Å

b = 13.350 (3) Å

c = 13.400 (3) Å

β = 103.02 (3)°

V = 1955.5 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.15 mm−1

T = 296 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.874, T max = 0.913

10453 measured reflections

3644 independent reflections

3099 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.088

S = 1.00

3644 reflections

280 parameters

H-atom parameters not refined

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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, global. DOI: 10.1107/S1600536809008976/bi2358sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008976/bi2358Isup2.hkl

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

[Cu2(C14H8O4)2(C10H8N2)2]	F(000) = 940
Mr = 919.86	Dx = 1.562 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3644 reflections
a = 11.220 (2) Å	θ = 2.1–25.5°
b = 13.350 (3) Å	µ = 1.15 mm−1
c = 13.400 (3) Å	T = 296 K
β = 103.02 (3)°	Block, blue
V = 1955.5 (7) Å3	0.12 × 0.10 × 0.08 mm
Z = 2

Bruker APEXII CCD diffractometer	3644 independent reflections
Radiation source: fine-focus sealed tube	3099 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→13
Tmin = 0.874, Tmax = 0.913	k = −16→10
10453 measured reflections	l = −16→14

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters not refined
S = 1.00	w = 1/[σ2(Fo2) + (0.063P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3
3644 reflections	(Δ/σ)max = 0.031
280 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.29 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
C1	0.52301 (18)	0.68894 (15)	0.42300 (15)	0.0295 (4)
C2	0.28746 (17)	0.57752 (15)	0.60591 (15)	0.0293 (4)
C3	0.30695 (16)	0.51522 (15)	0.70154 (14)	0.0270 (4)
C4	0.33117 (18)	0.56634 (16)	0.79532 (15)	0.0341 (5)
H4	0.3274	0.6359	0.7960	0.041*
C5	0.36046 (19)	0.51453 (18)	0.88649 (15)	0.0393 (5)
H5	0.3786	0.5489	0.9484	0.047*
C6	0.3627 (2)	0.41049 (18)	0.88508 (16)	0.0404 (5)
H6	0.3821	0.3752	0.9464	0.048*
C7	0.33624 (19)	0.35926 (16)	0.79356 (16)	0.0344 (5)
H7	0.3370	0.2896	0.7939	0.041*
C8	0.30828 (16)	0.41025 (15)	0.70031 (14)	0.0268 (4)
C9	0.66065 (16)	0.69929 (14)	0.45025 (14)	0.0270 (4)
C10	0.71452 (18)	0.75479 (16)	0.53682 (16)	0.0358 (5)
H10	0.6646	0.7884	0.5725	0.043*
C11	0.83990 (19)	0.76120 (16)	0.57103 (17)	0.0388 (5)
H11	0.8741	0.7992	0.6285	0.047*
C12	0.91368 (18)	0.71022 (17)	0.51856 (17)	0.0393 (5)
H12	0.9983	0.7130	0.5410	0.047*
C13	0.86141 (19)	0.65506 (15)	0.43273 (17)	0.0339 (5)
H13	0.9120	0.6208	0.3982	0.041*
C14	0.73499 (18)	0.64916 (13)	0.39621 (15)	0.0270 (4)
C15	0.2751 (2)	0.87802 (18)	0.39294 (19)	0.0426 (5)
H15	0.3426	0.8868	0.4470	0.051*
C16	0.2221 (2)	0.96089 (18)	0.3405 (2)	0.0522 (7)
H16	0.2509	1.0248	0.3605	0.063*
C17	0.1257 (2)	0.9477 (2)	0.2579 (2)	0.0557 (7)
H17	0.0896	1.0026	0.2202	0.067*
C18	0.0830 (2)	0.85266 (19)	0.2316 (2)	0.0463 (6)
H18	0.0188	0.8425	0.1751	0.056*
C19	0.13647 (18)	0.77206 (16)	0.29011 (15)	0.0320 (5)
C20	0.09346 (18)	0.66758 (16)	0.27505 (16)	0.0322 (5)
C21	−0.0050 (2)	0.6365 (2)	0.19990 (18)	0.0442 (6)
H21	−0.0477	0.6818	0.1522	0.053*
C22	−0.0390 (2)	0.5368 (2)	0.19696 (18)	0.0511 (7)
H22	−0.1050	0.5145	0.1468	0.061*
C23	0.0242 (2)	0.4706 (2)	0.26769 (19)	0.0481 (6)
H23	0.0014	0.4036	0.2664	0.058*
C24	0.1223 (2)	0.50567 (17)	0.34091 (17)	0.0390 (5)
H24	0.1658	0.4612	0.3890	0.047*
Cu1	0.30127 (2)	0.660694 (17)	0.440302 (17)	0.033 (2)
N1	0.15643 (14)	0.60194 (13)	0.34444 (12)	0.0304 (4)
N2	0.23357 (15)	0.78535 (13)	0.36946 (12)	0.0309 (4)
O1	0.46909 (13)	0.65650 (12)	0.33944 (13)	0.0462 (4)
O2	0.46709 (12)	0.71453 (11)	0.49257 (10)	0.0356 (3)
O3	0.23951 (18)	0.66102 (11)	0.60315 (13)	0.0510 (5)
O4	0.32843 (13)	0.54377 (10)	0.53117 (10)	0.0336 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0289 (10)	0.0228 (10)	0.0359 (11)	−0.0009 (8)	0.0052 (9)	−0.0015 (8)
C2	0.0303 (10)	0.0261 (11)	0.0293 (10)	−0.0008 (9)	0.0020 (8)	−0.0012 (8)
C3	0.0237 (9)	0.0287 (11)	0.0276 (10)	0.0006 (8)	0.0037 (8)	−0.0014 (8)
C4	0.0347 (11)	0.0317 (11)	0.0353 (11)	−0.0009 (9)	0.0066 (9)	−0.0056 (9)
C5	0.0389 (12)	0.0508 (14)	0.0255 (11)	0.0029 (10)	0.0017 (9)	−0.0075 (9)
C6	0.0429 (12)	0.0495 (14)	0.0281 (11)	0.0081 (11)	0.0064 (9)	0.0077 (10)
C7	0.0384 (12)	0.0307 (11)	0.0345 (12)	0.0044 (9)	0.0092 (9)	0.0057 (9)
C8	0.0242 (9)	0.0282 (11)	0.0285 (10)	0.0001 (8)	0.0070 (8)	0.0000 (8)
C9	0.0272 (10)	0.0219 (10)	0.0306 (10)	−0.0026 (8)	0.0037 (8)	−0.0006 (8)
C10	0.0384 (12)	0.0289 (11)	0.0410 (12)	−0.0041 (9)	0.0112 (10)	−0.0089 (9)
C11	0.0411 (12)	0.0324 (12)	0.0389 (12)	−0.0111 (10)	0.0006 (10)	−0.0098 (9)
C12	0.0273 (10)	0.0399 (13)	0.0474 (13)	−0.0093 (9)	0.0017 (9)	−0.0005 (10)
C13	0.0294 (11)	0.0344 (12)	0.0386 (12)	−0.0011 (9)	0.0094 (9)	−0.0025 (9)
C14	0.0285 (10)	0.0207 (10)	0.0302 (11)	−0.0030 (8)	0.0035 (8)	0.0037 (8)
C15	0.0469 (13)	0.0349 (13)	0.0462 (13)	0.0000 (11)	0.0107 (11)	0.0032 (10)
C16	0.0572 (16)	0.0295 (13)	0.0745 (18)	0.0032 (11)	0.0246 (14)	0.0086 (12)
C17	0.0516 (15)	0.0475 (16)	0.0698 (18)	0.0163 (12)	0.0177 (13)	0.0268 (13)
C18	0.0385 (13)	0.0495 (16)	0.0488 (15)	0.0134 (11)	0.0053 (11)	0.0158 (11)
C19	0.0284 (10)	0.0400 (12)	0.0292 (10)	0.0078 (9)	0.0095 (8)	0.0072 (9)
C20	0.0260 (10)	0.0433 (13)	0.0281 (11)	0.0036 (9)	0.0077 (8)	0.0052 (9)
C21	0.0310 (11)	0.0635 (17)	0.0344 (12)	−0.0044 (11)	−0.0006 (9)	0.0078 (11)
C22	0.0376 (13)	0.0725 (19)	0.0395 (14)	−0.0156 (12)	0.0010 (11)	−0.0042 (12)
C23	0.0442 (13)	0.0493 (15)	0.0501 (15)	−0.0174 (11)	0.0089 (11)	−0.0039 (12)
C24	0.0381 (11)	0.0380 (13)	0.0391 (12)	−0.0041 (10)	0.0051 (10)	0.0015 (10)
Cu1	0.045 (5)	0.025 (4)	0.028 (4)	−0.004 (4)	0.002 (4)	0.002 (3)
N1	0.0279 (8)	0.0338 (10)	0.0284 (9)	−0.0003 (7)	0.0042 (7)	0.0018 (7)
N2	0.0308 (9)	0.0305 (10)	0.0315 (9)	0.0017 (7)	0.0069 (7)	0.0038 (7)
O1	0.0303 (8)	0.0595 (11)	0.0457 (10)	−0.0038 (7)	0.0022 (7)	−0.0248 (8)
O2	0.0284 (7)	0.0461 (10)	0.0318 (8)	−0.0007 (6)	0.0058 (6)	−0.0052 (6)
O3	0.0790 (13)	0.0343 (10)	0.0429 (10)	0.0232 (8)	0.0207 (9)	0.0070 (7)
O4	0.0423 (8)	0.0315 (8)	0.0269 (7)	0.0067 (6)	0.0078 (6)	0.0043 (6)

Cu1—O1	2.5541 (17)	C11—H11	0.930
Cu1—O2	1.9701 (14)	C12—C13	1.380 (3)
Cu1—O3	2.4338 (17)	C12—H12	0.930
Cu1—O4	1.9608 (14)	C13—C14	1.395 (3)
Cu1—N1	1.9914 (17)	C13—H13	0.930
Cu1—N2	1.9806 (17)	C14—C8i	1.502 (3)
C1—O1	1.226 (2)	C15—N2	1.334 (3)
C1—O2	1.282 (2)	C15—C16	1.372 (3)
C1—C9	1.511 (3)	C15—H15	0.930
C2—O3	1.235 (2)	C16—C17	1.373 (4)
C2—O4	1.275 (2)	C16—H16	0.930
C2—C3	1.502 (3)	C17—C18	1.374 (4)
C3—C8	1.402 (3)	C17—H17	0.930
C3—C4	1.402 (3)	C18—C19	1.386 (3)
C4—C5	1.378 (3)	C18—H18	0.930
C4—H4	0.930	C19—N2	1.352 (3)
C5—C6	1.389 (3)	C19—C20	1.475 (3)
C5—H5	0.930	C20—N1	1.355 (3)
C6—C7	1.377 (3)	C20—C21	1.381 (3)
C6—H6	0.930	C21—C22	1.383 (4)
C7—C8	1.395 (3)	C21—H21	0.930
C7—H7	0.930	C22—C23	1.370 (4)
C8—C14i	1.502 (3)	C22—H22	0.930
C9—C14	1.393 (3)	C23—C24	1.381 (3)
C9—C10	1.394 (3)	C23—H23	0.9300
C10—C11	1.381 (3)	C24—N1	1.339 (3)
C10—H10	0.930	C24—H24	0.930
C11—C12	1.380 (3)
O1—C1—O2	122.48 (18)	C17—C16—H16	120.6
O1—C1—C9	121.35 (18)	C15—C16—H16	120.6
O2—C1—C9	116.17 (17)	C16—C17—C18	119.4 (2)
O3—C2—O4	121.83 (18)	C16—C17—H17	120.3
O3—C2—C3	120.29 (18)	C18—C17—H17	120.3
O4—C2—C3	117.75 (17)	C19—C18—C17	119.4 (2)
C8—C3—C4	119.79 (18)	C19—C18—H18	120.3
C8—C3—C2	122.93 (17)	C17—C18—H18	120.3
C4—C3—C2	117.19 (18)	N2—C19—C18	120.8 (2)
C5—C4—C3	120.7 (2)	N2—C19—C20	114.37 (17)
C5—C4—H4	119.7	C18—C19—C20	124.8 (2)
C3—C4—H4	119.7	N1—C20—C21	121.0 (2)
C4—C5—C6	119.4 (2)	N1—C20—C19	114.45 (18)
C4—C5—H5	120.3	C21—C20—C19	124.6 (2)
C6—C5—H5	120.3	C20—C21—C22	118.7 (2)
C7—C6—C5	120.52 (19)	C20—C21—H21	120.7
C7—C6—H6	119.7	C22—C21—H21	120.7
C5—C6—H6	119.7	C23—C22—C21	120.3 (2)
C6—C7—C8	121.0 (2)	C23—C22—H22	119.9
C6—C7—H7	119.5	C21—C22—H22	119.9
C8—C7—H7	119.5	C22—C23—C24	118.6 (2)
C7—C8—C3	118.56 (18)	C22—C23—H23	120.7
C7—C8—C14i	118.53 (18)	C24—C23—H23	120.7
C3—C8—C14i	122.41 (17)	N1—C24—C23	121.8 (2)
C14—C9—C10	119.32 (18)	N1—C24—H24	119.1
C14—C9—C1	121.98 (17)	C23—C24—H24	119.1
C10—C9—C1	118.52 (17)	O4—Cu1—O2	93.87 (6)
C11—C10—C9	121.83 (19)	O4—Cu1—N2	162.88 (6)
C11—C10—H10	119.1	O2—Cu1—N2	95.36 (7)
C9—C10—H10	119.1	O4—Cu1—N1	94.42 (7)
C12—C11—C10	118.92 (19)	O2—Cu1—N1	160.23 (6)
C12—C11—H11	120.5	N2—Cu1—N1	81.52 (7)
C10—C11—H11	120.5	O4—Cu1—O3	58.70 (5)
C11—C12—C13	119.77 (19)	O2—Cu1—O3	96.74 (7)
C11—C12—H12	120.1	N2—Cu1—O3	105.80 (6)
C13—C12—H12	120.1	N1—Cu1—O3	102.90 (7)
C14—C13—C12	122.0 (2)	C24—N1—C20	119.72 (18)
C14—C13—H13	119.0	C24—N1—Cu1	125.89 (14)
C12—C13—H13	119.0	C20—N1—Cu1	114.30 (14)
C13—C14—C9	118.12 (18)	C15—N2—C19	118.94 (18)
C13—C14—C8i	115.98 (17)	C15—N2—Cu1	126.17 (15)
C9—C14—C8i	125.89 (17)	C19—N2—Cu1	114.89 (14)
N2—C15—C16	122.6 (2)	C1—O2—Cu1	102.82 (12)
N2—C15—H15	118.7	C2—O3—Cu1	79.35 (12)
C16—C15—H15	118.7	C2—O4—Cu1	99.98 (12)
C17—C16—C15	118.8 (2)