Tetra­kis(μ-4-methyl­benzoato-κ2O:O′)bis­[(isonicotinamide-κN)copper(II)]

Necefoğlu, H.; Çimen, E.; Tercan, B.; Dal, H.; Hökelek, T.

doi:10.1107/S1600536810006513

Volume 66
Part 3
Pages m334-m335
March 2010

Received 18 February 2010
Accepted 19 February 2010
Online 27 February 2010

Key indicators
Single-crystal X-ray study
T = 101 K
Mean (C-C) = 0.004 Å
R = 0.043
wR = 0.087
Data-to-parameter ratio = 18.2
Details

Tetrakis(-4-methylbenzoato-²O:O')bis[(isonicotinamide-N)copper(II)]

Hacali Necefoglu,^a Efdal Çimen,^a Baris Tercan,^b Hakan Dal ^c and Tuncer Hökelek ^d ^*

^aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey,^bDepartment of Physics, Karabük University, 78050 Karabük, Turkey,^cDepartment of Chemistry, Faculty of Science, Anadolu University, 26470 Yenibaglar, Eskisehir, Turkey, and ^dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title centrosymmetric binuclear complex, [Cu₂(C₈H₇O₂)₄(C₆H₆N₂O)₂], the Cu atoms [CuCu = 2.6375 (6) Å] are bridged by four 4-methylbenzoate (PMB) ligands. The four nearest O atoms around each Cu^II ion form a distorted square-planar arrangement, and the distorted square-pyramidal coordination is completed by the pyridine N atom of the isonicotinamide (INA) ligand. Each Cu^II ion is displaced by 0.2633 (1) Å from the plane of the four O atoms, with an average Cu-O distance of 1.974 (2) Å. The dihedral angles between carboxylate groups and the adjacent benzene rings are 7.88 (19) and 9.68 (10)°, while the benzene rings are oriented at a dihedral angle of 85.90 (9)°. The pyridine ring is oriented at dihedral angles of 8.59 (7) and 83.89 (9)° with respect to the benzene rings. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules into a three-dimensional network. [pi] - [pi] contacts between the benzene rings and between the pyridine and benzene rings, [centroid-centroid distances = 3.563 (2) and 3.484 (2) Å, respectively] may further stabilize the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974), and for the nicotinic acid derivative N,N-diethylnicotinamide, see: Bigoli et al. (1972). For related structures, see: Hökelek et al. (1995, 2009a,b,c); Speier & Fulop (1989); Usubaliev et al. (1980).

Experimental

Crystal data

[Cu₂(C₈H₇O₂)₄(C₆H₆N₂O)₂]
M_r = 911.88
Monoclinic, P 2₁ /c
a = 11.2305 (2) Å
b = 23.4691 (4) Å
c = 8.0087 (1) Å
= 102.128 (1)°
V = 2063.74 (6) Å³
Z = 2
Mo K radiation
= 1.10 mm^-1
T = 101 K
0.30 × 0.24 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.735, T_max = 0.862
20056 measured reflections
5101 independent reflections
3629 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.087
S = 1.01
5101 reflections
281 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.47 e Å^-3
_min = -0.70 e Å^-3

Table 1
Selected bond lengths (Å)

Cu1-O1	1.9733 (18)
Cu1-O2ⁱ	1.9703 (18)
Cu1-O3	1.9687 (18)
Cu1-O4	1.9836 (18)
Cu1-N1	2.161 (2)
Symmetry code: (i) -x+2, -y+2, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO5ⁱⁱ	0.89 (3)	2.11 (3)	2.984 (3)	169 (3)
Symmetry code: (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2729 ).

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of X-ray diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 108 T657).

References

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