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Volume 69 
Part 5 
Pages m290-m291  
May 2013  

Received 29 March 2013
Accepted 22 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.008 Å
Disorder in main residue
R = 0.078
wR = 0.204
Data-to-parameter ratio = 15.9
Details
Open access

Bis([mu]-4-formylbenzoato-[kappa]2O:O')bis[(4-formylbenzoato-[kappa]2O,O')bis(isonicotinamide-[kappa]N1)copper(II)]

aDepartment of Chemistry, Kafkas University, 63100 Kars, Turkey,bDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The asymmetric unit of the centrosymmetric dinuclear title compound, [Cu2(C8H5O3)4(C6H6N2O)4], contains one half of the complex molecule. The CuII atoms are bridged by the carboxylate groups of two 4-formylbenzoate (FOB) anions. Besides the two bridging FOB anions, one additional chelating FOB anion and two isonicotinamide (INA) ligands complete the distorted CuN2O4 octahedral coordination of each Cu2+ cation. Within the asymmetric unit, the benzene and pyridine rings are oriented at dihedral angles of 25.1 (3) and 12.6 (3)°, respectively. In the crystal, N-H...O and C-H...O hydrogen bonds link the molecules into a three-dimensional network. [pi]-[pi] contacts between the pyridine rings [shortest centroid-centroid distance = 3.821 (3) Å] may further stabilize the crystal structure. One of the formyl groups of the two FOB anions is disordered over two sets of sites with an occupancy ratio of 0.65:0.35.

Related literature

For general background, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]); Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For related structures, see: Hökelek (1996[Hökelek, T., Gündüz, H. & Necefouglu, H. (1996). Acta Cryst. C52, 2470-2473.], 2009a[Hökelek, T., Yilmaz, F., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009a). Acta Cryst. E65, m955-m956.],b[Hökelek, T., Yilmaz, F., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009b). Acta Cryst. E65, m1328-m1329.],c[Hökelek, T., Yilmaz, F., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009c). Acta Cryst. E65, m1608-m1609.])); Greenaway et al. (1984[Greenaway, F. T., Pazeshk, A., Cordes, A. W., Noble, M. C. & Sorenson, J. R. J. (1984). Inorg. Chim. Acta, 93, 67-71.]); Necefoglu et al. (2011[Necefoglu, H., Özbek, F. E., Öztürk, V., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m887-m888.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu2(C8H5O3)4(C6H6N2O)4]

  • Mr = 1212.09

  • Triclinic, [P \overline 1]

  • a = 8.6462 (2) Å

  • b = 11.6709 (3) Å

  • c = 13.4339 (4) Å

  • [alpha] = 87.876 (3)°

  • [beta] = 83.483 (3)°

  • [gamma] = 74.566 (2)°

  • V = 1298.24 (6) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.90 mm-1

  • T = 100 K

  • 0.17 × 0.07 × 0.06 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.927, Tmax = 0.947

  • 19200 measured reflections

  • 6198 independent reflections

  • 4412 reflections with I > 2[sigma](I)

  • Rint = 0.189

Refinement
  • R[F2 > 2[sigma](F2)] = 0.078

  • wR(F2) = 0.204

  • S = 1.11

  • 6198 reflections

  • 389 parameters

  • 119 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 1.05 e Å-3

  • [Delta][rho]min = -1.51 e Å-3

Table 1
Selected bond lengths (Å)

Cu1-O1 1.994 (3)
Cu1-O2 2.736 (4)
Cu1-O3 1.949 (4)
Cu1-O4i 2.242 (3)
Cu1-N1 2.033 (4)
Cu1-N2 2.013 (4)
Symmetry code: (i) -x+1, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O2ii 0.86 2.17 2.997 (6) 160
N3-H3B...O5Aiii 0.86 2.27 3.044 (9) 149
N4-H4A...O7iv 0.86 2.06 2.878 (6) 158
N4-H4B...O2v 0.86 2.10 2.890 (6) 152
C3-H3...O7vi 0.93 2.52 3.391 (7) 155
C6-H6...O8vii 0.93 2.44 3.336 (9) 162
C18-H18...O5Aiii 0.93 2.35 3.274 (9) 169
C23-H23...O2v 0.93 2.54 3.432 (7) 162
C24-H24...O6viii 0.93 2.50 3.217 (7) 134
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z; (iv) x+1, y, z+1; (v) -x+2, -y+1, -z+2; (vi) x+1, y, z; (vii) -x+1, -y+2, -z+2; (viii) -x+2, -y, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2735 ).


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 the X-ray diffractometer. This work was supported financially by Kafkas University Research Fund (grant No. 2012-FEF-12).

References

Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.  [CrossRef] [ChemPort] [details] [ISI]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Greenaway, F. T., Pazeshk, A., Cordes, A. W., Noble, M. C. & Sorenson, J. R. J. (1984). Inorg. Chim. Acta, 93, 67-71.  [CrossRef] [ChemPort] [ISI]
Hökelek, T., Gündüz, H. & Necefouglu, H. (1996). Acta Cryst. C52, 2470-2473.  [CrossRef] [details]
Hökelek, T., Yilmaz, F., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009a). Acta Cryst. E65, m955-m956.  [CSD] [CrossRef] [details]
Hökelek, T., Yilmaz, F., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009b). Acta Cryst. E65, m1328-m1329.  [CSD] [CrossRef] [details]
Hökelek, T., Yilmaz, F., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009c). Acta Cryst. E65, m1608-m1609.  [CSD] [CrossRef] [details]
Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.  [ChemPort] [PubMed]
Necefoglu, H., Özbek, F. E., Öztürk, V., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m887-m888.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m290-m291   [ doi:10.1107/S1600536813010908 ]

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