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Acta Cryst. (2009). E65, m4-m5    [ doi:10.1107/S1600536808039913 ]

Bis([mu]-3-carboxy-2-oxidobenzoato)-[kappa]3O1,O2:O3;[kappa]3O3:O1,O2-bis[aqua(2,2'-bipyridine-[kappa]2N,N')copper(II)]

J. Gao, B.-Y. Zhu and D.-L. Cui

Abstract top

In the centrosymmetric dinuclear complex, [Cu2(C8H4O5)2(C10H8N2)2(H2O)2], the CuII ion is coordinated by two N atoms from a bipyridine ligand, three O atoms from two 3-carboxy-2-oxidobenzoate dianions and the O atom of the water molecule in a distorted octahedral 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.

Comment top

2,2-Bipyridine and benzenedicarboxylate (BDC) anion are good organic ligands for copper which can construct supramolecular structure via hydrogen bonds and π-π aromatic interactions. We present here the crystal structure of [Cu2(bpy)2(ipO)2(H2O)2], where bpy is 2,2,-bipyridine and ipOH is 2-hydroxyisophthalate.

The title compound is a centrosymmetric dinuclear complex (Fig. 1). Each CuII ion is coordinated by two N atoms (N1 and N2) from a bipyridine ligand in a bidentate chelating fashion and three O atoms (O2, O3 and O5i) of two ipO dianions and the O atom (O1) of the solvent water molecule, in a distorted octahedral geometry. The Cu1—-O5i coordination [2.931 (3) Å] is very weak. The CuII atom is located 0.209 (1) Å above the basal plane formed by atoms N1, N2, O2 and O3. The mean Cu—N(bpy) distance of 2.006 (2) Å and the bite angle N1—Cu1—N2 of 80.43 (8)° are close to the corresponding values observed in related copper-bipyridine compounds (Augustin et al., 2005).

In the crystal structure, the centrosymmetric dinuclear units are linked into a two-dimensional network parallel to the (010) (Fig. 2) by O—H···O hydrogen bonds.

In [Cu2(bpy)2(ipO)2(H2O)2], the isophthalic acid (ipa) was in situ oxidative hydroxylated before coordinating with CuII ion (Tao et al., 2002). Similar in situ oxidation has also been reported for 1,2,3-benzenetricarboxylic acid (Zheng et al., 2004).

Related literature top

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

Experimental top

Copper(II) chloride dihydrate (0.043 g, 0.251 mol), 2,2,-bipyridine (0.039 g, 0.249 mol), isophthalic acid (0.083 g, 0.500 mol), potassium hydroxide (0.055 g, 0.982 mol) and deionized water (18 ml) were mixed together. The mixture was sealed in a Teflon-lined stainless steel vessel (25 ml) and then heated at 453 K for 36 h under autogenous pressure and then cooled to room temperature. Light-green crystals were obtained by slow evaporation of the mother-liquor in the air for a few days.

Refinement top

O-bound H atoms were located in a difference map and then restrained to ride on their parent atoms, with a O-H distance of 0.84 (1) Å. C-bound H atoms were positioned geometrically and treated as riding, with C-H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top
[Figure 1] Fig. 1. The structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Symmetry code: (i) -x + 2, -y + 1, -z + 2.
[Figure 2] Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.
Bis(µ-3-carboxy-2-oxidobenzoato)- κ3O1,O2:O3;κ3O3:O1,O2- bis[aqua(2,2'-bipyridine-κ2N,N')copper(II)] top
Crystal data top
[Cu2(C8H4O5)2(C10H8N2)2(H2O)2]Z = 1
Mr = 835.70F(000) = 426
Triclinic, P1Dx = 1.680 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.354 (5) ÅCell parameters from 3943 reflections
b = 10.635 (5) Åθ = 2.1–28.2°
c = 11.038 (5) ŵ = 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
Data collection top
Bruker APEXII area-detector
diffractometer		3686 independent reflections
Radiation source: fine-focus sealed tube2989 reflections with I > 2σ(I)
graphiteRint = 0.016
φ and ω scansθmax = 28.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −11→10
Tmin = 0.772, Tmax = 0.801k = −11→14
4985 measured reflectionsl = −14→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-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 parametersΔρmax = 0.32 e Å−3
3 restraintsΔρmin = −0.25 e Å−3
Crystal data top
[Cu2(C8H4O5)2(C10H8N2)2(H2O)2]γ = 89.269 (5)°
Mr = 835.70V = 825.8 (7) Å3
Triclinic, P1Z = 1
a = 8.354 (5) ÅMo Kα radiation
b = 10.635 (5) ŵ = 1.36 mm−1
c = 11.038 (5) ÅT = 293 K
α = 66.812 (5)°0.20 × 0.20 × 0.17 mm
β = 68.070 (5)°
Data collection top
Bruker APEXII area-detector
diffractometer		3686 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2989 reflections with I > 2σ(I)
Tmin = 0.772, Tmax = 0.801Rint = 0.016
4985 measured reflectionsθmax = 28.2°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.084Δρmax = 0.32 e Å−3
S = 1.17Δρmin = −0.25 e Å−3
3686 reflectionsAbsolute structure: ?
247 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Cu11.02424 (4)0.40419 (3)0.79285 (3)0.03492 (11)
O10.8041 (2)0.2876 (2)0.78123 (19)0.0477 (5)
H1A0.84600.28700.70030.050 (9)*
H1B0.72200.33290.78080.073 (11)*
O20.8826 (2)0.50132 (17)0.89930 (16)0.0386 (4)
O50.7156 (2)0.47764 (18)1.14597 (18)0.0428 (4)
H50.79250.47611.07200.079 (11)*
O31.0772 (2)0.56037 (18)0.61539 (18)0.0475 (5)
O60.4835 (2)0.5775 (2)1.19418 (19)0.0472 (5)
O41.0474 (3)0.7547 (2)0.46051 (18)0.0546 (5)
C10.8480 (3)0.6833 (2)0.6998 (2)0.0328 (5)
C20.7521 (3)0.7865 (3)0.6566 (3)0.0429 (6)
H20.78390.83960.55880.052*
N21.2225 (3)0.3176 (2)0.7039 (2)0.0342 (5)
C50.6589 (3)0.6344 (2)0.9478 (2)0.0319 (5)
C80.6095 (3)0.5615 (3)1.1045 (3)0.0351 (5)
C60.8000 (3)0.6034 (2)0.8478 (2)0.0297 (5)
C141.1417 (3)0.1660 (2)0.9492 (3)0.0344 (5)
N11.0135 (3)0.2428 (2)0.9707 (2)0.0343 (5)
C131.2642 (3)0.2115 (2)0.7976 (3)0.0345 (5)
C91.3259 (3)0.3668 (3)0.5628 (3)0.0420 (6)
H91.29610.43920.49760.050*
C101.4742 (4)0.3132 (3)0.5122 (3)0.0507 (7)
H101.54340.34840.41420.061*
C40.5662 (3)0.7384 (3)0.8979 (3)0.0416 (6)
H40.47230.75710.96350.050*
C70.9998 (3)0.6649 (3)0.5847 (3)0.0371 (6)
C30.6113 (4)0.8133 (3)0.7535 (3)0.0482 (7)
H30.54770.88150.72120.058*
C121.4127 (4)0.1550 (3)0.7521 (3)0.0485 (7)
H121.44080.08230.81820.058*
C111.5186 (4)0.2078 (3)0.6077 (3)0.0536 (8)
H111.61990.17170.57550.064*
C151.1534 (4)0.0535 (3)1.0627 (3)0.0464 (7)
H151.24110.00011.04610.056*
C170.9043 (4)0.1000 (3)1.2207 (3)0.0521 (7)
H170.82210.07991.31300.063*
C180.8958 (4)0.2081 (3)1.1050 (3)0.0442 (6)
H180.80510.25931.12020.053*
C161.0337 (4)0.0218 (3)1.2004 (3)0.0537 (8)
H161.0410−0.05191.27830.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.04080 (18)0.03336 (18)0.02357 (16)0.01615 (13)−0.01105 (12)−0.00717 (12)
O10.0447 (10)0.0642 (13)0.0384 (11)0.0230 (10)−0.0178 (9)−0.0249 (10)
O20.0488 (10)0.0383 (10)0.0242 (8)0.0205 (8)−0.0135 (7)−0.0103 (7)
O50.0467 (10)0.0488 (11)0.0264 (9)0.0202 (9)−0.0107 (8)−0.0137 (8)
O30.0555 (11)0.0443 (11)0.0262 (9)0.0261 (9)−0.0092 (8)−0.0059 (8)
O60.0440 (10)0.0587 (12)0.0378 (10)0.0187 (9)−0.0114 (8)−0.0241 (9)
O40.0678 (13)0.0475 (11)0.0248 (9)0.0273 (10)−0.0096 (9)−0.0011 (8)
C10.0371 (13)0.0301 (13)0.0296 (12)0.0095 (10)−0.0145 (10)−0.0100 (10)
C20.0507 (16)0.0395 (15)0.0331 (14)0.0143 (12)−0.0185 (12)−0.0085 (12)
N20.0383 (11)0.0321 (11)0.0316 (11)0.0103 (9)−0.0150 (9)−0.0120 (9)
C50.0338 (12)0.0318 (13)0.0309 (12)0.0079 (10)−0.0134 (10)−0.0136 (10)
C80.0346 (13)0.0369 (14)0.0344 (13)0.0052 (11)−0.0119 (11)−0.0175 (11)
C60.0330 (12)0.0277 (12)0.0288 (12)0.0082 (10)−0.0136 (10)−0.0110 (10)
C140.0427 (14)0.0268 (12)0.0368 (13)0.0081 (10)−0.0214 (11)−0.0112 (11)
N10.0406 (11)0.0293 (11)0.0287 (10)0.0083 (9)−0.0135 (9)−0.0083 (9)
C130.0378 (13)0.0291 (13)0.0386 (14)0.0085 (10)−0.0180 (11)−0.0136 (11)
C90.0462 (15)0.0398 (15)0.0351 (14)0.0097 (12)−0.0124 (12)−0.0148 (12)
C100.0457 (16)0.0519 (18)0.0434 (16)0.0078 (13)−0.0042 (13)−0.0222 (14)
C40.0396 (14)0.0444 (15)0.0417 (15)0.0171 (12)−0.0144 (12)−0.0210 (12)
C70.0430 (14)0.0350 (14)0.0262 (12)0.0098 (11)−0.0135 (11)−0.0064 (11)
C30.0534 (16)0.0428 (16)0.0479 (16)0.0251 (13)−0.0246 (14)−0.0149 (13)
C120.0488 (16)0.0416 (16)0.0586 (18)0.0202 (13)−0.0248 (14)−0.0216 (14)
C110.0397 (15)0.0534 (18)0.062 (2)0.0163 (13)−0.0105 (14)−0.0286 (16)
C150.0559 (17)0.0329 (14)0.0512 (17)0.0139 (12)−0.0295 (14)−0.0108 (13)
C170.0705 (19)0.0396 (16)0.0288 (14)0.0033 (14)−0.0141 (13)−0.0027 (12)
C180.0507 (16)0.0360 (14)0.0351 (14)0.0103 (12)−0.0132 (12)−0.0082 (12)
C160.076 (2)0.0358 (15)0.0418 (16)0.0098 (14)−0.0311 (15)−0.0020 (13)
Geometric parameters (Å, °) top
Cu1—O31.8976 (18)C5—C81.477 (3)
Cu1—O21.9325 (17)C14—N11.346 (3)
Cu1—N22.004 (2)C14—C151.385 (3)
Cu1—N12.007 (2)C14—C131.475 (3)
Cu1—O12.301 (2)N1—C181.338 (3)
Cu1—O5i2.931 (2)C13—C121.380 (3)
O1—H1A0.83C9—C101.374 (4)
O1—H1B0.83C9—H90.93
O2—C61.328 (3)C10—C111.362 (4)
O5—C81.324 (3)C10—H100.93
O5—H50.84C4—C31.369 (4)
O3—C71.272 (3)C4—H40.93
O6—C81.211 (3)C3—H30.93
O4—C71.233 (3)C12—C111.376 (4)
C1—C21.387 (3)C12—H120.93
C1—C61.407 (3)C11—H110.93
C1—C71.499 (3)C15—C161.376 (4)
C2—C31.378 (4)C15—H150.93
C2—H20.93C17—C161.361 (4)
N2—C131.344 (3)C17—C181.367 (4)
N2—C91.346 (3)C17—H170.93
C5—C41.394 (3)C18—H180.93
C5—C61.422 (3)C16—H160.93
O3—Cu1—O291.52 (8)C15—C14—C13124.1 (2)
O3—Cu1—N292.25 (8)C18—N1—C14118.6 (2)
O2—Cu1—N2162.60 (8)C18—N1—Cu1126.46 (17)
O3—Cu1—N1169.99 (8)C14—N1—Cu1114.96 (15)
O2—Cu1—N193.53 (8)N2—C13—C12121.3 (2)
N2—Cu1—N180.43 (8)N2—C13—C14114.3 (2)
O3—Cu1—O196.20 (8)C12—C13—C14124.5 (2)
O2—Cu1—O198.23 (8)N2—C9—C10121.9 (3)
N2—Cu1—O198.25 (8)N2—C9—H9119.0
N1—Cu1—O191.63 (8)C10—C9—H9119.0
O3—Cu1—O5i92.34 (8)C11—C10—C9119.1 (3)
O2—Cu1—O5i79.41 (8)C11—C10—H10120.5
N2—Cu1—O5i83.47 (8)C9—C10—H10120.5
N1—Cu1—O5i80.11 (8)C3—C4—C5120.9 (2)
O1—Cu1—O5i171.22 (6)C3—C4—H4119.5
Cu1—O1—H1A105.3C5—C4—H4119.5
Cu1—O1—H1B110.7O4—C7—O3121.6 (2)
H1A—O1—H1B104.9O4—C7—C1117.8 (2)
C6—O2—Cu1124.77 (15)O3—C7—C1120.6 (2)
C8—O5—H5107.2C4—C3—C2119.3 (2)
C7—O3—Cu1130.12 (16)C4—C3—H3120.3
C2—C1—C6118.8 (2)C2—C3—H3120.3
C2—C1—C7117.6 (2)C11—C12—C13119.1 (3)
C6—C1—C7123.6 (2)C11—C12—H12120.4
C3—C2—C1122.4 (2)C13—C12—H12120.4
C3—C2—H2118.8C10—C11—C12119.7 (3)
C1—C2—H2118.8C10—C11—H11120.2
C13—N2—C9118.9 (2)C12—C11—H11120.2
C13—N2—Cu1115.19 (16)C16—C15—C14119.2 (3)
C9—N2—Cu1125.39 (17)C16—C15—H15120.4
C4—C5—C6119.7 (2)C14—C15—H15120.4
C4—C5—C8118.5 (2)C16—C17—C18119.8 (3)
C6—C5—C8121.8 (2)C16—C17—H17120.1
O6—C8—O5119.4 (2)C18—C17—H17120.1
O6—C8—C5124.2 (2)N1—C18—C17122.2 (3)
O5—C8—C5116.3 (2)N1—C18—H18118.9
O2—C6—C1123.1 (2)C17—C18—H18118.9
O2—C6—C5118.1 (2)C17—C16—C15118.9 (3)
C1—C6—C5118.8 (2)C17—C16—H16120.5
N1—C14—C15121.3 (2)C15—C16—H16120.5
N1—C14—C13114.6 (2)
O3—Cu1—O2—C627.15 (19)O2—Cu1—N1—C14−158.90 (17)
N2—Cu1—O2—C6129.6 (3)N2—Cu1—N1—C144.66 (17)
N1—Cu1—O2—C6−161.50 (19)O1—Cu1—N1—C14102.75 (18)
O1—Cu1—O2—C6−69.34 (19)C9—N2—C13—C121.7 (4)
O2—Cu1—O3—C7−19.2 (2)Cu1—N2—C13—C12−170.8 (2)
N2—Cu1—O3—C7177.8 (2)C9—N2—C13—C14−179.9 (2)
N1—Cu1—O3—C7−139.5 (4)Cu1—N2—C13—C147.6 (3)
O1—Cu1—O3—C779.3 (2)N1—C14—C13—N2−3.7 (3)
C6—C1—C2—C3−0.2 (4)C15—C14—C13—N2176.0 (2)
C7—C1—C2—C3−179.3 (2)N1—C14—C13—C12174.7 (2)
O3—Cu1—N2—C13166.35 (18)C15—C14—C13—C12−5.6 (4)
O2—Cu1—N2—C1364.0 (3)C13—N2—C9—C10−1.1 (4)
N1—Cu1—N2—C13−6.78 (17)Cu1—N2—C9—C10170.6 (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—C3177.2 (2)
N1—Cu1—N2—C9−178.7 (2)Cu1—O3—C7—O4−176.2 (2)
O1—Cu1—N2—C991.0 (2)Cu1—O3—C7—C14.4 (4)
C4—C5—C8—O66.7 (4)C2—C1—C7—O410.8 (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—O57.6 (3)C6—C1—C7—O311.1 (4)
Cu1—O2—C6—C1−21.3 (3)C5—C4—C3—C2−0.9 (4)
Cu1—O2—C6—C5160.03 (16)C1—C2—C3—C41.8 (4)
C2—C1—C6—O2179.2 (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—C121.4 (5)
C7—C1—C6—C5176.8 (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—O23.1 (3)C13—C14—C15—C16178.8 (2)
C4—C5—C6—C13.0 (4)C14—N1—C18—C171.7 (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—C18179.5 (2)C18—C17—C16—C15−0.2 (5)
C15—C14—N1—Cu1178.29 (19)C14—C15—C16—C171.6 (4)
C13—C14—N1—Cu1−2.0 (3)O5i—Cu1—O2—C6119.26 (19)
O3—Cu1—N1—C18139.6 (4)O5i—Cu1—O3—C7−98.6 (3)
O2—Cu1—N1—C1819.4 (2)O5i—Cu1—N2—C1374.20 (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—C1898.1 (2)
O3—Cu1—N1—C14−38.7 (5)O5i—Cu1—N1—C14−80.29 (18)
Symmetry codes: (i) −x+2, −y+1, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O20.841.672.461 (2)156
O1—H1B···O6ii0.831.932.763 (3)173
O1—H1A···O4iii0.831.892.706 (3)167
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Cu1—O31.8976 (18)Cu1—N12.007 (2)
Cu1—O21.9325 (17)Cu1—O12.301 (2)
Cu1—N22.004 (2)Cu1—O5i2.931 (2)
Symmetry codes: (i) −x+2, −y+1, −z+2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O20.841.672.461 (2)156
O1—H1B···O6ii0.831.932.763 (3)173
O1—H1A···O4iii0.831.892.706 (3)167
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+1, −z+1.
Acknowledgements top

We thank Professor Dao-feng Sun and Dr Xi-feng Lu for the data collection and helpful discussions. This work was supported by the National Natural Science Foundation of China (grant Nos. 50672048 and 50721002).

references
References top

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