Bis(μ-3-carb-oxy-2-oxidobenzoato)-κO,O:O;κO:O,O-bis-[aqua-(2,2'-bipyridine-κN,N')copper(II)].

In the centrosymmetric dinuclear complex, [Cu(2)(C(8)H(4)O(5))(2)(C(10)H(8)N(2))(2)(H(2)O)(2)], the Cu(II) ion is coordinated by two N atoms from a bipyridine ligand, three O atoms from two 3-carb-oxy-2-oxidobenzoate dianions and the O atom of the water mol-ecule in a distorted octa-hedral geometry. The Cu--O(H) coordination [2.931 (3) Å] is very weak. In the crystal structure, the dinuclear units are linked into a two-dimensional network parallel to (010) by O-H⋯O hydrogen bonds.

Related literature

For related structures, see: Augustin et al. (2005 ▶); Tao et al. (2002 ▶); Zheng et al. (2004 ▶).

Experimental

Crystal data

[Cu2(C8H4O5)2(C10H8N2)2(H2O)2]

M = 835.70

Triclinic,

a = 8.354 (5) Å

b = 10.635 (5) Å

c = 11.038 (5) Å

α = 66.812 (5)°

β = 68.070 (5)°

γ = 89.269 (5)°

V = 825.8 (7) Å3

Z = 1

Mo Kα radiation

μ = 1.36 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.17 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.772, T max = 0.801

4985 measured reflections

3686 independent reflections

2989 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.084

S = 1.17

3686 reflections

247 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039913/ci2713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039913/ci2713Isup2.hkl

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

[Cu2(C8H4O5)2(C10H8N2)2(H2O)2]	Z = 1
Mr = 835.70	F(000) = 426
Triclinic, P1	Dx = 1.680 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.354 (5) Å	Cell parameters from 3943 reflections
b = 10.635 (5) Å	θ = 2.1–28.2°
c = 11.038 (5) Å	µ = 1.36 mm−1
α = 66.812 (5)°	T = 293 K
β = 68.070 (5)°	Block, green
γ = 89.269 (5)°	0.20 × 0.20 × 0.17 mm
V = 825.8 (7) Å3

Bruker APEXII area-detector diffractometer	3686 independent reflections
Radiation source: fine-focus sealed tube	2989 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 28.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→10
Tmin = 0.772, Tmax = 0.801	k = −11→14
4985 measured reflections	l = −14→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0284P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3
3686 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 0.32 e Å−3
3 restraints	Δρmin = −0.25 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
Cu1	1.02424 (4)	0.40419 (3)	0.79285 (3)	0.03492 (11)
O1	0.8041 (2)	0.2876 (2)	0.78123 (19)	0.0477 (5)
H1A	0.8460	0.2870	0.7003	0.050 (9)*
H1B	0.7220	0.3329	0.7808	0.073 (11)*
O2	0.8826 (2)	0.50132 (17)	0.89930 (16)	0.0386 (4)
O5	0.7156 (2)	0.47764 (18)	1.14597 (18)	0.0428 (4)
H5	0.7925	0.4761	1.0720	0.079 (11)*
O3	1.0772 (2)	0.56037 (18)	0.61539 (18)	0.0475 (5)
O6	0.4835 (2)	0.5775 (2)	1.19418 (19)	0.0472 (5)
O4	1.0474 (3)	0.7547 (2)	0.46051 (18)	0.0546 (5)
C1	0.8480 (3)	0.6833 (2)	0.6998 (2)	0.0328 (5)
C2	0.7521 (3)	0.7865 (3)	0.6566 (3)	0.0429 (6)
H2	0.7839	0.8396	0.5588	0.052*
N2	1.2225 (3)	0.3176 (2)	0.7039 (2)	0.0342 (5)
C5	0.6589 (3)	0.6344 (2)	0.9478 (2)	0.0319 (5)
C8	0.6095 (3)	0.5615 (3)	1.1045 (3)	0.0351 (5)
C6	0.8000 (3)	0.6034 (2)	0.8478 (2)	0.0297 (5)
C14	1.1417 (3)	0.1660 (2)	0.9492 (3)	0.0344 (5)
N1	1.0135 (3)	0.2428 (2)	0.9707 (2)	0.0343 (5)
C13	1.2642 (3)	0.2115 (2)	0.7976 (3)	0.0345 (5)
C9	1.3259 (3)	0.3668 (3)	0.5628 (3)	0.0420 (6)
H9	1.2961	0.4392	0.4976	0.050*
C10	1.4742 (4)	0.3132 (3)	0.5122 (3)	0.0507 (7)
H10	1.5434	0.3484	0.4142	0.061*
C4	0.5662 (3)	0.7384 (3)	0.8979 (3)	0.0416 (6)
H4	0.4723	0.7571	0.9635	0.050*
C7	0.9998 (3)	0.6649 (3)	0.5847 (3)	0.0371 (6)
C3	0.6113 (4)	0.8133 (3)	0.7535 (3)	0.0482 (7)
H3	0.5477	0.8815	0.7212	0.058*
C12	1.4127 (4)	0.1550 (3)	0.7521 (3)	0.0485 (7)
H12	1.4408	0.0823	0.8182	0.058*
C11	1.5186 (4)	0.2078 (3)	0.6077 (3)	0.0536 (8)
H11	1.6199	0.1717	0.5755	0.064*
C15	1.1534 (4)	0.0535 (3)	1.0627 (3)	0.0464 (7)
H15	1.2411	0.0001	1.0461	0.056*
C17	0.9043 (4)	0.1000 (3)	1.2207 (3)	0.0521 (7)
H17	0.8221	0.0799	1.3130	0.063*
C18	0.8958 (4)	0.2081 (3)	1.1050 (3)	0.0442 (6)
H18	0.8051	0.2593	1.1202	0.053*
C16	1.0337 (4)	0.0218 (3)	1.2004 (3)	0.0537 (8)
H16	1.0410	−0.0519	1.2783	0.064*

	U11	U22	U33	U12	U13	U23
Cu1	0.04080 (18)	0.03336 (18)	0.02357 (16)	0.01615 (13)	−0.01105 (12)	−0.00717 (12)
O1	0.0447 (10)	0.0642 (13)	0.0384 (11)	0.0230 (10)	−0.0178 (9)	−0.0249 (10)
O2	0.0488 (10)	0.0383 (10)	0.0242 (8)	0.0205 (8)	−0.0135 (7)	−0.0103 (7)
O5	0.0467 (10)	0.0488 (11)	0.0264 (9)	0.0202 (9)	−0.0107 (8)	−0.0137 (8)
O3	0.0555 (11)	0.0443 (11)	0.0262 (9)	0.0261 (9)	−0.0092 (8)	−0.0059 (8)
O6	0.0440 (10)	0.0587 (12)	0.0378 (10)	0.0187 (9)	−0.0114 (8)	−0.0241 (9)
O4	0.0678 (13)	0.0475 (11)	0.0248 (9)	0.0273 (10)	−0.0096 (9)	−0.0011 (8)
C1	0.0371 (13)	0.0301 (13)	0.0296 (12)	0.0095 (10)	−0.0145 (10)	−0.0100 (10)
C2	0.0507 (16)	0.0395 (15)	0.0331 (14)	0.0143 (12)	−0.0185 (12)	−0.0085 (12)
N2	0.0383 (11)	0.0321 (11)	0.0316 (11)	0.0103 (9)	−0.0150 (9)	−0.0120 (9)
C5	0.0338 (12)	0.0318 (13)	0.0309 (12)	0.0079 (10)	−0.0134 (10)	−0.0136 (10)
C8	0.0346 (13)	0.0369 (14)	0.0344 (13)	0.0052 (11)	−0.0119 (11)	−0.0175 (11)
C6	0.0330 (12)	0.0277 (12)	0.0288 (12)	0.0082 (10)	−0.0136 (10)	−0.0110 (10)
C14	0.0427 (14)	0.0268 (12)	0.0368 (13)	0.0081 (10)	−0.0214 (11)	−0.0112 (11)
N1	0.0406 (11)	0.0293 (11)	0.0287 (10)	0.0083 (9)	−0.0135 (9)	−0.0083 (9)
C13	0.0378 (13)	0.0291 (13)	0.0386 (14)	0.0085 (10)	−0.0180 (11)	−0.0136 (11)
C9	0.0462 (15)	0.0398 (15)	0.0351 (14)	0.0097 (12)	−0.0124 (12)	−0.0148 (12)
C10	0.0457 (16)	0.0519 (18)	0.0434 (16)	0.0078 (13)	−0.0042 (13)	−0.0222 (14)
C4	0.0396 (14)	0.0444 (15)	0.0417 (15)	0.0171 (12)	−0.0144 (12)	−0.0210 (12)
C7	0.0430 (14)	0.0350 (14)	0.0262 (12)	0.0098 (11)	−0.0135 (11)	−0.0064 (11)
C3	0.0534 (16)	0.0428 (16)	0.0479 (16)	0.0251 (13)	−0.0246 (14)	−0.0149 (13)
C12	0.0488 (16)	0.0416 (16)	0.0586 (18)	0.0202 (13)	−0.0248 (14)	−0.0216 (14)
C11	0.0397 (15)	0.0534 (18)	0.062 (2)	0.0163 (13)	−0.0105 (14)	−0.0286 (16)
C15	0.0559 (17)	0.0329 (14)	0.0512 (17)	0.0139 (12)	−0.0295 (14)	−0.0108 (13)
C17	0.0705 (19)	0.0396 (16)	0.0288 (14)	0.0033 (14)	−0.0141 (13)	−0.0027 (12)
C18	0.0507 (16)	0.0360 (14)	0.0351 (14)	0.0103 (12)	−0.0132 (12)	−0.0082 (12)
C16	0.076 (2)	0.0358 (15)	0.0418 (16)	0.0098 (14)	−0.0311 (15)	−0.0020 (13)

Cu1—O3	1.8976 (18)	C5—C8	1.477 (3)
Cu1—O2	1.9325 (17)	C14—N1	1.346 (3)
Cu1—N2	2.004 (2)	C14—C15	1.385 (3)
Cu1—N1	2.007 (2)	C14—C13	1.475 (3)
Cu1—O1	2.301 (2)	N1—C18	1.338 (3)
Cu1—O5i	2.931 (2)	C13—C12	1.380 (3)
O1—H1A	0.83	C9—C10	1.374 (4)
O1—H1B	0.83	C9—H9	0.93
O2—C6	1.328 (3)	C10—C11	1.362 (4)
O5—C8	1.324 (3)	C10—H10	0.93
O5—H5	0.84	C4—C3	1.369 (4)
O3—C7	1.272 (3)	C4—H4	0.93
O6—C8	1.211 (3)	C3—H3	0.93
O4—C7	1.233 (3)	C12—C11	1.376 (4)
C1—C2	1.387 (3)	C12—H12	0.93
C1—C6	1.407 (3)	C11—H11	0.93
C1—C7	1.499 (3)	C15—C16	1.376 (4)
C2—C3	1.378 (4)	C15—H15	0.93
C2—H2	0.93	C17—C16	1.361 (4)
N2—C13	1.344 (3)	C17—C18	1.367 (4)
N2—C9	1.346 (3)	C17—H17	0.93
C5—C4	1.394 (3)	C18—H18	0.93
C5—C6	1.422 (3)	C16—H16	0.93
O3—Cu1—O2	91.52 (8)	C15—C14—C13	124.1 (2)
O3—Cu1—N2	92.25 (8)	C18—N1—C14	118.6 (2)
O2—Cu1—N2	162.60 (8)	C18—N1—Cu1	126.46 (17)
O3—Cu1—N1	169.99 (8)	C14—N1—Cu1	114.96 (15)
O2—Cu1—N1	93.53 (8)	N2—C13—C12	121.3 (2)
N2—Cu1—N1	80.43 (8)	N2—C13—C14	114.3 (2)
O3—Cu1—O1	96.20 (8)	C12—C13—C14	124.5 (2)
O2—Cu1—O1	98.23 (8)	N2—C9—C10	121.9 (3)
N2—Cu1—O1	98.25 (8)	N2—C9—H9	119.0
N1—Cu1—O1	91.63 (8)	C10—C9—H9	119.0
O3—Cu1—O5i	92.34 (8)	C11—C10—C9	119.1 (3)
O2—Cu1—O5i	79.41 (8)	C11—C10—H10	120.5
N2—Cu1—O5i	83.47 (8)	C9—C10—H10	120.5
N1—Cu1—O5i	80.11 (8)	C3—C4—C5	120.9 (2)
O1—Cu1—O5i	171.22 (6)	C3—C4—H4	119.5
Cu1—O1—H1A	105.3	C5—C4—H4	119.5
Cu1—O1—H1B	110.7	O4—C7—O3	121.6 (2)
H1A—O1—H1B	104.9	O4—C7—C1	117.8 (2)
C6—O2—Cu1	124.77 (15)	O3—C7—C1	120.6 (2)
C8—O5—H5	107.2	C4—C3—C2	119.3 (2)
C7—O3—Cu1	130.12 (16)	C4—C3—H3	120.3
C2—C1—C6	118.8 (2)	C2—C3—H3	120.3
C2—C1—C7	117.6 (2)	C11—C12—C13	119.1 (3)
C6—C1—C7	123.6 (2)	C11—C12—H12	120.4
C3—C2—C1	122.4 (2)	C13—C12—H12	120.4
C3—C2—H2	118.8	C10—C11—C12	119.7 (3)
C1—C2—H2	118.8	C10—C11—H11	120.2
C13—N2—C9	118.9 (2)	C12—C11—H11	120.2
C13—N2—Cu1	115.19 (16)	C16—C15—C14	119.2 (3)
C9—N2—Cu1	125.39 (17)	C16—C15—H15	120.4
C4—C5—C6	119.7 (2)	C14—C15—H15	120.4
C4—C5—C8	118.5 (2)	C16—C17—C18	119.8 (3)
C6—C5—C8	121.8 (2)	C16—C17—H17	120.1
O6—C8—O5	119.4 (2)	C18—C17—H17	120.1
O6—C8—C5	124.2 (2)	N1—C18—C17	122.2 (3)
O5—C8—C5	116.3 (2)	N1—C18—H18	118.9
O2—C6—C1	123.1 (2)	C17—C18—H18	118.9
O2—C6—C5	118.1 (2)	C17—C16—C15	118.9 (3)
C1—C6—C5	118.8 (2)	C17—C16—H16	120.5
N1—C14—C15	121.3 (2)	C15—C16—H16	120.5
N1—C14—C13	114.6 (2)
O3—Cu1—O2—C6	27.15 (19)	O2—Cu1—N1—C14	−158.90 (17)
N2—Cu1—O2—C6	129.6 (3)	N2—Cu1—N1—C14	4.66 (17)
N1—Cu1—O2—C6	−161.50 (19)	O1—Cu1—N1—C14	102.75 (18)
O1—Cu1—O2—C6	−69.34 (19)	C9—N2—C13—C12	1.7 (4)
O2—Cu1—O3—C7	−19.2 (2)	Cu1—N2—C13—C12	−170.8 (2)
N2—Cu1—O3—C7	177.8 (2)	C9—N2—C13—C14	−179.9 (2)
N1—Cu1—O3—C7	−139.5 (4)	Cu1—N2—C13—C14	7.6 (3)
O1—Cu1—O3—C7	79.3 (2)	N1—C14—C13—N2	−3.7 (3)
C6—C1—C2—C3	−0.2 (4)	C15—C14—C13—N2	176.0 (2)
C7—C1—C2—C3	−179.3 (2)	N1—C14—C13—C12	174.7 (2)
O3—Cu1—N2—C13	166.35 (18)	C15—C14—C13—C12	−5.6 (4)
O2—Cu1—N2—C13	64.0 (3)	C13—N2—C9—C10	−1.1 (4)
N1—Cu1—N2—C13	−6.78 (17)	Cu1—N2—C9—C10	170.6 (2)
O1—Cu1—N2—C13	−97.06 (18)	N2—C9—C10—C11	−0.5 (4)
O3—Cu1—N2—C9	−5.6 (2)	C6—C5—C4—C3	−1.4 (4)
O2—Cu1—N2—C9	−107.9 (3)	C8—C5—C4—C3	177.2 (2)
N1—Cu1—N2—C9	−178.7 (2)	Cu1—O3—C7—O4	−176.2 (2)
O1—Cu1—N2—C9	91.0 (2)	Cu1—O3—C7—C1	4.4 (4)
C4—C5—C8—O6	6.7 (4)	C2—C1—C7—O4	10.8 (4)
C6—C5—C8—O6	−174.7 (2)	C6—C1—C7—O4	−168.3 (2)
C4—C5—C8—O5	−170.9 (2)	C2—C1—C7—O3	−169.8 (3)
C6—C5—C8—O5	7.6 (3)	C6—C1—C7—O3	11.1 (4)
Cu1—O2—C6—C1	−21.3 (3)	C5—C4—C3—C2	−0.9 (4)
Cu1—O2—C6—C5	160.03 (16)	C1—C2—C3—C4	1.8 (4)
C2—C1—C6—O2	179.2 (2)	N2—C13—C12—C11	−0.7 (4)
C7—C1—C6—O2	−1.8 (4)	C14—C13—C12—C11	−178.9 (3)
C2—C1—C6—C5	−2.2 (4)	C9—C10—C11—C12	1.4 (5)
C7—C1—C6—C5	176.8 (2)	C13—C12—C11—C10	−0.8 (4)
C4—C5—C6—O2	−178.3 (2)	N1—C14—C15—C16	−1.5 (4)
C8—C5—C6—O2	3.1 (3)	C13—C14—C15—C16	178.8 (2)
C4—C5—C6—C1	3.0 (4)	C14—N1—C18—C17	1.7 (4)
C8—C5—C6—C1	−175.6 (2)	Cu1—N1—C18—C17	−176.6 (2)
C15—C14—N1—C18	−0.2 (4)	C16—C17—C18—N1	−1.5 (5)
C13—C14—N1—C18	179.5 (2)	C18—C17—C16—C15	−0.2 (5)
C15—C14—N1—Cu1	178.29 (19)	C14—C15—C16—C17	1.6 (4)
C13—C14—N1—Cu1	−2.0 (3)	O5i—Cu1—O2—C6	119.26 (19)
O3—Cu1—N1—C18	139.6 (4)	O5i—Cu1—O3—C7	−98.6 (3)
O2—Cu1—N1—C18	19.4 (2)	O5i—Cu1—N2—C13	74.20 (18)
N2—Cu1—N1—C18	−177.0 (2)	O5i—Cu1—N2—C9	−97.7 (2)
O1—Cu1—N1—C18	−78.9 (2)	O5i—Cu1—N1—C18	98.1 (2)
O3—Cu1—N1—C14	−38.7 (5)	O5i—Cu1—N1—C14	−80.29 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2	0.84	1.67	2.461 (2)	156
O1—H1B···O6ii	0.83	1.93	2.763 (3)	173
O1—H1A···O4iii	0.83	1.89	2.706 (3)	167

Table 1

Selected bond lengths (Å)

Cu1—O3	1.8976 (18)
Cu1—O2	1.9325 (17)
Cu1—N2	2.004 (2)
Cu1—N1	2.007 (2)
Cu1—O1	2.301 (2)
Cu1—O5i	2.931 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2	0.84	1.67	2.461 (2)	156
O1—H1B⋯O6ii	0.83	1.93	2.763 (3)	173
O1—H1A⋯O4iii	0.83	1.89	2.706 (3)	167

Symmetry codes: (ii) ; (iii) .