Bis(μ-biphenyl-2,2′-dicarboxyl­ato)bis­[(2,2′-bipyridine)copper(II)]

An, Z.; Cui, R.-H.; Zhou, R.-J.

doi:10.1107/S1600536809008976

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m412

doi:10.1107/S1600536809008976

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Bis(μ-biphenyl-2,2′-dicarboxylato)bis[(2,2′-bipyridine)copper(II)]

Zhe An,^a ^* Rui-Hai Cui ^b and Ru-Jin Zhou ^a

^aSchool of Chemistry and Life Science, Maoming University, Maoming 525000, People's Republic of China, and ^bSchool of Chemistry and Life Science, Harbin University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: anz_md@163.com

(Received 10 March 2009; accepted 11 March 2009; online 19 March 2009)

The title compound, [Cu₂(C₁₄H₈O₄)₂(C₁₀H₈N₂)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′-dicarboxylate ligands, leading to a distorted octahedral environment. Each carboxylate 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′-dicarboxylate 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_r = 919.86
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.088
S = 1.00
3644 reflections
280 parameters
H-atom parameters not refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008976/bi2358sup1.cif

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

checkCIF report

Comment top

Biphenyl-2,2'-dicarboxylic acid (H₂dpa) has been demonstrated to be a good candidate for the construction of metal-organic frameworks, and some complexes based on 2,2'-dpa have been reported (Rueff et al., 2003; Xu et al., 2006; An & Niu, 2008). In this paper, we report a new metal complex constructed from dpa, 2,2-bipyridine and copper(II) (Figure 1).

Related literature top

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 top

A mixture of Cu(CH₃COO)₂.H₂O (1 mmol), biphenyl-2,2'-dicarboxylic acid (1 mmol), and 2,2'-bipyridine (1 mmol) in 20 ml methanol/water (1:1) were placed in a 25 ml Teflon-lined stainless steel autoclave and kept at 453 K for five days. Blue crystals were obtained after cooling to room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure drawn with 30% probability displacement ellipsoids for the non-H atoms. Unlabelled atoms are related to labelled atoms by the symmetry code 1 - x, 1 - y, 1 - z.

Bis(µ-biphenyl-2,2'-dicarboxylato)bis[(2,2'-bipyridine)copper(II)] top

Crystal data top

[Cu₂(C₁₄H₈O₄)₂(C₁₀H₈N₂)₂]	F(000) = 940
M_r = 919.86	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.063P)² + 0.1P] where P = (F_o² + 2F_c²)/3
3644 reflections	(Δ/σ)_max = 0.031
280 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Cu₂(C₁₄H₈O₄)₂(C₁₀H₈N₂)₂]	V = 1955.5 (7) Å³
M_r = 919.86	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.220 (2) Å	µ = 1.15 mm⁻¹
b = 13.350 (3) Å	T = 296 K
c = 13.400 (3) Å	0.12 × 0.10 × 0.08 mm
β = 103.02 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3644 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3099 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.913	R_int = 0.019
10453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.088	H-atom parameters not refined
S = 1.00	Δρ_max = 0.27 e Å⁻³
3644 reflections	Δρ_min = −0.29 e Å⁻³
280 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₄H₈O₄)₂(C₁₀H₈N₂)₂]
M_r	919.86
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.220 (2), 13.350 (3), 13.400 (3)
β (°)	103.02 (3)
V (Å³)	1955.5 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.874, 0.913
No. of measured, independent and observed [I > 2σ(I)] reflections	10453, 3644, 3099
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.088, 1.00
No. of reflections	3644
No. of parameters	280
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors acknowledge financial support from Maoming University.

References

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