metal-organic compounds
Tetrakis(μ-acetato-κ2O:O′)-bis[(3-pyridinecarboxaldehyde-κN′)]dicopper(II)(Cu—Cu)
aFacultad de Ingenieria Mochis, Universidad Autonoma de Sinaloa, Fuente Poseidon y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, Mexico, bCentro de Investigaciones Quimicas, Universidad Autonoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, Mexico, and cCentro de Graduados del Instituto Tecnologico de Tijuana, Blvd. Industrial S/N Col. Otay, CP 22500, Tijuana, B.C., Mexico
*Correspondence e-mail: gaxiolajose@yahoo.com.mx
The binuclear title compound, [Cu2(CH3CO2)4(C6H5NO)], is located about a center of inversion. The CuII atoms are connected [Cu—Cu = 2.6134 (5) Å] and bridged by four acetate ligands. Their distorted octahedral coordination geometry is completed by a terminal pyridine N atom of a 3-pyridincarboxaldehyde ligand. In the crystal, the complex molecules are linked by C—H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane. These networks are linked via C—H⋯O hydrogen bonds involving inversion-related 3-pyridinecarboxaldehyde ligands, forming a three dimensional supramolecular architecture.
Related literature
For related paddle-wheel structures, see: Aakeröy et al. (2003); Sieroń (2004); Fairuz et al. (2011); Trivedi et al. (2011). For Cu⋯Cu separations in related structures, see: Seco et al. (2004); Asem et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al. 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812041074/su2505sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041074/su2505Isup2.hkl
A mixture of 3-pyridincarboxaldehyde (0.05 g, 0.466 mmol) and Cu(CH3COO)2H2O (0.093 g, 0.466 mmol) dissolved in methanol (5 ml) was stirred for 2 h at room temperature to give a blue solution. After one week, blue crystals suitable for X-ray
had been formed, which were collected by filtration [Yield: 65%]. Spectroscopic and TGA data are given in the archived CIF.The C-bound H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.93 and 096 Å for CH and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.5 for CH3 H-atoms and = 1.2 for other H-atoms.
Data collection: SMART (Bruker, 2000); cell
SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al. 2008); software used to prepare material for publication: publCIF (Westrip, 2010).[Cu2(C2H3O2)4(C6H5NO)] | Z = 1 |
Mr = 577.48 | F(000) = 294 |
Triclinic, P1 | Dx = 1.689 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4099 (6) Å | Cell parameters from 3727 reflections |
b = 8.4298 (7) Å | θ = 2.5–28.3° |
c = 10.0254 (8) Å | µ = 1.93 mm−1 |
α = 100.353 (1)° | T = 100 K |
β = 108.975 (1)° | Rectangular prism, blue |
γ = 98.679 (1)° | 0.48 × 0.21 × 0.17 mm |
V = 567.61 (8) Å3 |
Bruker SMART CCD area-detector diffractometer | 1980 independent reflections |
Radiation source: fine-focus sealed tube | 1921 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
phi and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.448, Tmax = 0.720 | k = −8→10 |
4118 measured reflections | l = −11→11 |
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) = 0.068 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0297P)2 + 0.5378P] where P = (Fo2 + 2Fc2)/3 |
1980 reflections | (Δ/σ)max = 0.001 |
156 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
[Cu2(C2H3O2)4(C6H5NO)] | γ = 98.679 (1)° |
Mr = 577.48 | V = 567.61 (8) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.4099 (6) Å | Mo Kα radiation |
b = 8.4298 (7) Å | µ = 1.93 mm−1 |
c = 10.0254 (8) Å | T = 100 K |
α = 100.353 (1)° | 0.48 × 0.21 × 0.17 mm |
β = 108.975 (1)° |
Bruker SMART CCD area-detector diffractometer | 1980 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1921 reflections with I > 2σ(I) |
Tmin = 0.448, Tmax = 0.720 | Rint = 0.018 |
4118 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.068 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.41 e Å−3 |
1980 reflections | Δρmin = −0.36 e Å−3 |
156 parameters |
Experimental. Spectroscopic and TGA data for the title compound: IR (KBr, cm-1): 3273, 3076, 2935, 2871, 1705, 1615, 1440, 1218, 1035, 690; TGA Calcd. for 2(C6H5NO): 37.07. Found: 37.53% (303 - 473 K). |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.56063 (4) | 0.57222 (3) | 0.91251 (3) | 0.0137 (1) | |
O1 | 1.1945 (3) | 0.9402 (3) | 0.6523 (2) | 0.0382 (7) | |
O2 | 0.6188 (3) | 0.3569 (2) | 0.85203 (19) | 0.0232 (5) | |
O3 | 0.5192 (3) | 0.2340 (2) | 1.00330 (18) | 0.0216 (5) | |
O4 | 0.2879 (2) | 0.4870 (2) | 0.77698 (18) | 0.0235 (5) | |
O5 | 0.1855 (2) | 0.3580 (2) | 0.92442 (18) | 0.0243 (5) | |
N1 | 0.6613 (3) | 0.6761 (2) | 0.7573 (2) | 0.0155 (6) | |
C1 | 0.8501 (4) | 0.7380 (3) | 0.7858 (2) | 0.0192 (7) | |
C2 | 0.9167 (4) | 0.8063 (3) | 0.6899 (3) | 0.0203 (7) | |
C3 | 0.7811 (4) | 0.8086 (3) | 0.5568 (3) | 0.0215 (8) | |
C4 | 0.5870 (4) | 0.7427 (3) | 0.5258 (3) | 0.0223 (7) | |
C5 | 0.5325 (4) | 0.6786 (3) | 0.6284 (3) | 0.0198 (7) | |
C6 | 1.1288 (4) | 0.8746 (4) | 0.7290 (3) | 0.0306 (9) | |
C7 | 0.5933 (3) | 0.2365 (3) | 0.9070 (2) | 0.0172 (7) | |
C8 | 0.6587 (4) | 0.0847 (3) | 0.8539 (3) | 0.0230 (8) | |
C9 | 0.1593 (3) | 0.3988 (3) | 0.8058 (2) | 0.0168 (7) | |
C10 | −0.0418 (4) | 0.3371 (3) | 0.6896 (3) | 0.0242 (8) | |
H1 | 0.94130 | 0.73520 | 0.87420 | 0.0230* | |
H3 | 0.82120 | 0.85370 | 0.49020 | 0.0260* | |
H4 | 0.49320 | 0.74120 | 0.43710 | 0.0270* | |
H5 | 0.40040 | 0.63520 | 0.60690 | 0.0240* | |
H6 | 1.21540 | 0.86630 | 0.81720 | 0.0370* | |
H8A | 0.58970 | 0.04310 | 0.75100 | 0.0340* | |
H8B | 0.63120 | 0.00150 | 0.90290 | 0.0340* | |
H8C | 0.79690 | 0.11290 | 0.87380 | 0.0340* | |
H10A | −0.06390 | 0.22020 | 0.65090 | 0.0360* | |
H10B | −0.05110 | 0.39310 | 0.61300 | 0.0360* | |
H10C | −0.13850 | 0.35880 | 0.73070 | 0.0360* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0144 (2) | 0.0153 (2) | 0.0134 (2) | 0.0035 (1) | 0.0066 (1) | 0.0051 (1) |
O1 | 0.0245 (10) | 0.0576 (14) | 0.0370 (11) | 0.0009 (9) | 0.0121 (9) | 0.0276 (10) |
O2 | 0.0356 (10) | 0.0191 (9) | 0.0269 (9) | 0.0118 (8) | 0.0217 (8) | 0.0106 (7) |
O3 | 0.0309 (10) | 0.0186 (9) | 0.0244 (9) | 0.0100 (7) | 0.0174 (8) | 0.0096 (7) |
O4 | 0.0165 (9) | 0.0326 (10) | 0.0188 (8) | −0.0007 (8) | 0.0039 (7) | 0.0096 (7) |
O5 | 0.0168 (9) | 0.0343 (10) | 0.0200 (9) | 0.0000 (7) | 0.0050 (7) | 0.0103 (8) |
N1 | 0.0195 (10) | 0.0129 (10) | 0.0157 (9) | 0.0028 (8) | 0.0083 (8) | 0.0042 (8) |
C1 | 0.0222 (13) | 0.0214 (12) | 0.0162 (11) | 0.0070 (10) | 0.0069 (10) | 0.0085 (9) |
C2 | 0.0211 (13) | 0.0213 (13) | 0.0226 (12) | 0.0068 (10) | 0.0102 (10) | 0.0096 (10) |
C3 | 0.0266 (14) | 0.0243 (13) | 0.0180 (12) | 0.0052 (11) | 0.0125 (11) | 0.0079 (10) |
C4 | 0.0231 (13) | 0.0276 (14) | 0.0146 (11) | 0.0042 (11) | 0.0042 (10) | 0.0072 (10) |
C5 | 0.0194 (12) | 0.0199 (12) | 0.0190 (12) | 0.0018 (10) | 0.0072 (10) | 0.0042 (10) |
C6 | 0.0220 (14) | 0.0439 (17) | 0.0291 (14) | 0.0053 (12) | 0.0082 (12) | 0.0202 (13) |
C7 | 0.0139 (11) | 0.0195 (12) | 0.0154 (11) | 0.0018 (9) | 0.0029 (9) | 0.0033 (9) |
C8 | 0.0263 (14) | 0.0195 (13) | 0.0260 (13) | 0.0067 (10) | 0.0128 (11) | 0.0051 (10) |
C9 | 0.0161 (12) | 0.0176 (12) | 0.0166 (11) | 0.0048 (10) | 0.0068 (10) | 0.0018 (9) |
C10 | 0.0187 (13) | 0.0334 (15) | 0.0181 (12) | 0.0028 (11) | 0.0053 (10) | 0.0053 (10) |
Cu1—O2 | 1.9643 (19) | C3—C4 | 1.371 (4) |
Cu1—O4 | 1.9677 (17) | C4—C5 | 1.385 (4) |
Cu1—N1 | 2.189 (2) | C7—C8 | 1.505 (4) |
Cu1—O3i | 1.9625 (19) | C9—C10 | 1.506 (4) |
Cu1—O5i | 1.9692 (17) | C1—H1 | 0.9300 |
O1—C6 | 1.204 (4) | C3—H3 | 0.9300 |
O2—C7 | 1.257 (3) | C4—H4 | 0.9300 |
O3—C7 | 1.258 (3) | C5—H5 | 0.9300 |
O4—C9 | 1.260 (3) | C6—H6 | 0.9300 |
O5—C9 | 1.260 (3) | C8—H8A | 0.9600 |
N1—C1 | 1.333 (4) | C8—H8B | 0.9600 |
N1—C5 | 1.340 (3) | C8—H8C | 0.9600 |
C1—C2 | 1.386 (4) | C10—H10A | 0.9600 |
C2—C3 | 1.391 (4) | C10—H10B | 0.9600 |
C2—C6 | 1.483 (4) | C10—H10C | 0.9600 |
O2—Cu1—O4 | 89.70 (8) | O3—C7—C8 | 117.9 (2) |
O2—Cu1—N1 | 92.99 (8) | O4—C9—O5 | 125.2 (2) |
O2—Cu1—O3i | 168.80 (8) | O4—C9—C10 | 117.59 (19) |
O2—Cu1—O5i | 90.47 (8) | O5—C9—C10 | 117.3 (2) |
O4—Cu1—N1 | 94.72 (7) | N1—C1—H1 | 118.00 |
O3i—Cu1—O4 | 88.36 (8) | C2—C1—H1 | 119.00 |
O4—Cu1—O5i | 168.89 (7) | C2—C3—H3 | 121.00 |
O3i—Cu1—N1 | 98.16 (7) | C4—C3—H3 | 121.00 |
O5i—Cu1—N1 | 96.36 (7) | C3—C4—H4 | 120.00 |
O3i—Cu1—O5i | 89.32 (8) | C5—C4—H4 | 120.00 |
Cu1—O2—C7 | 124.41 (17) | N1—C5—H5 | 118.00 |
Cu1i—O3—C7 | 121.63 (16) | C4—C5—H5 | 119.00 |
Cu1—O4—C9 | 123.33 (14) | O1—C6—H6 | 118.00 |
Cu1i—O5—C9 | 122.48 (15) | C2—C6—H6 | 118.00 |
Cu1—N1—C1 | 122.12 (14) | C7—C8—H8A | 109.00 |
Cu1—N1—C5 | 120.33 (19) | C7—C8—H8B | 110.00 |
C1—N1—C5 | 117.6 (2) | C7—C8—H8C | 109.00 |
N1—C1—C2 | 123.1 (2) | H8A—C8—H8B | 109.00 |
C1—C2—C3 | 118.7 (3) | H8A—C8—H8C | 109.00 |
C1—C2—C6 | 120.3 (3) | H8B—C8—H8C | 110.00 |
C3—C2—C6 | 121.0 (3) | C9—C10—H10A | 109.00 |
C2—C3—C4 | 118.6 (3) | C9—C10—H10B | 109.00 |
C3—C4—C5 | 119.1 (3) | C9—C10—H10C | 110.00 |
N1—C5—C4 | 123.1 (3) | H10A—C10—H10B | 109.00 |
O1—C6—C2 | 123.3 (3) | H10A—C10—H10C | 110.00 |
O2—C7—O3 | 125.1 (2) | H10B—C10—H10C | 109.00 |
O2—C7—C8 | 117.1 (2) | ||
O2—Cu1—N1—C1 | −82.47 (19) | Cu1—O2—C7—C8 | −176.00 (17) |
O2—Cu1—N1—C5 | 97.24 (19) | Cu1—O2—C7—O3 | 3.4 (3) |
O4—Cu1—N1—C1 | −172.41 (18) | Cu1i—O3—C7—O2 | −2.2 (3) |
O4—Cu1—N1—C5 | 7.30 (19) | Cu1i—O3—C7—C8 | 177.20 (17) |
O3i—Cu1—N1—C1 | 98.57 (19) | Cu1—O4—C9—O5 | 2.2 (3) |
O3i—Cu1—N1—C5 | −81.72 (19) | Cu1—O4—C9—C10 | −177.83 (16) |
O5i—Cu1—N1—C1 | 8.34 (19) | Cu1i—O5—C9—O4 | −0.1 (3) |
O5i—Cu1—N1—C5 | −171.95 (18) | Cu1i—O5—C9—C10 | 179.91 (17) |
O4—Cu1—O2—C7 | −86.4 (2) | Cu1—N1—C1—C2 | −179.13 (19) |
N1—Cu1—O2—C7 | 178.9 (2) | C5—N1—C1—C2 | 1.2 (4) |
O5i—Cu1—O2—C7 | 82.5 (2) | Cu1—N1—C5—C4 | 179.93 (19) |
O5—Cu1i—O3—C7 | 85.16 (19) | C1—N1—C5—C4 | −0.4 (4) |
O4i—Cu1i—O3—C7 | −83.97 (19) | N1—C1—C2—C6 | 179.4 (2) |
N1i—Cu1i—O3—C7 | −178.51 (18) | N1—C1—C2—C3 | −0.9 (4) |
O2—Cu1—O4—C9 | 80.85 (19) | C1—C2—C6—O1 | −177.5 (3) |
N1—Cu1—O4—C9 | 173.83 (18) | C6—C2—C3—C4 | 179.5 (3) |
O3i—Cu1—O4—C9 | −88.12 (19) | C1—C2—C3—C4 | −0.2 (4) |
O3—Cu1i—O5—C9 | −86.94 (19) | C3—C2—C6—O1 | 2.8 (5) |
O2i—Cu1i—O5—C9 | 81.86 (19) | C2—C3—C4—C5 | 0.9 (4) |
N1i—Cu1i—O5—C9 | 174.92 (18) | C3—C4—C5—N1 | −0.7 (4) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1ii | 0.93 | 2.43 | 3.262 (4) | 148 |
C6—H6···O3iii | 0.93 | 2.56 | 3.449 (4) | 159 |
C8—H8B···O3iv | 0.96 | 2.60 | 3.542 (3) | 168 |
C10—H10C···O2v | 0.96 | 2.48 | 3.420 (4) | 167 |
Symmetry codes: (ii) −x+2, −y+2, −z+1; (iii) −x+2, −y+1, −z+2; (iv) −x+1, −y, −z+2; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu2(C2H3O2)4(C6H5NO)] |
Mr | 577.48 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 7.4099 (6), 8.4298 (7), 10.0254 (8) |
α, β, γ (°) | 100.353 (1), 108.975 (1), 98.679 (1) |
V (Å3) | 567.61 (8) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.93 |
Crystal size (mm) | 0.48 × 0.21 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.448, 0.720 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4118, 1980, 1921 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.068, 1.10 |
No. of reflections | 1980 |
No. of parameters | 156 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.36 |
Computer programs: SMART (Bruker, 2000), SAINT-Plus-NT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al. 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O1i | 0.93 | 2.43 | 3.262 (4) | 148 |
C6—H6···O3ii | 0.93 | 2.56 | 3.449 (4) | 159 |
C8—H8B···O3iii | 0.96 | 2.60 | 3.542 (3) | 168 |
C10—H10C···O2iv | 0.96 | 2.48 | 3.420 (4) | 167 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y, −z+2; (iv) x−1, y, z. |
Acknowledgements
This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2011/033). ABC thanks the Consejo Nacional de Ciencia y Tecnologia (CONACYT) for support in the form of a scholarship.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Bridged binuclear copper(II) complexes have been the subject of continuing interest because of their magneto-structural properties. Pyridine ligands have the potential to be used in the synthesis of supramolecular materials, particularly transition metal coordination polymers. Herein, we report on the synthesis and crystal structure of the new binuclear Cu2(OAc)4L2 paddle-wheel complex with L = 3-pyridincarboxaldehyde.
The title complex (Fig. 1) is structurally similar to paddle-wheel structures of other Cu2(OAc)4L2 complexes (Aakeröy et al., 2003; Fairuz et al., 2011; Seco et al., 2004; Sieroń, 2004; Trivedi et al., 2011). The binuclear molecule lies about an inversion center. Attached to the Cu2(OAc)4 core unit there are two apical pyridine groups from 3-pyridincarboxaldehyde ligands. The Cu—O distances [which vary from 1.9625 (19) - 1.9692 (17) Å], the Cu1—N1 distance [2.189 (2) Å], and the corresponding bond angles are consistent with the structurally similar CuIIcomplexes mentioned above. Although the Cu1—Cu1i separation of 2.6134 (6) Å [symmetry code: (i) -x+1, -y+1, -z+2] is towards the lower limit, it is within the range of values reported for other CuII paddle-wheel structures (Sieroń, 2004; Asem et al., 2011).
In the crystal, the complex molecules are linked by C—H···O hydrogen bonds to form two-dimensional networks lying parallel to the ab plane (Table 1 and Fig. 2). These networks are linked via C-H···O hydrogen bonds involving inversion related 3-pyridincarboxaldehyde ligands forming a three dimensional supramolecular architecture (Table 1).