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Volume 69 
Part 8 
Pages m431-m432  
August 2013  

Received 27 June 2013
Accepted 28 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.083
Data-to-parameter ratio = 16.7
Details
Open access

Tetrakis([mu]-3-chlorobenzoato-[kappa]2O:O')bis[(N,N-diethylnicotinamide-[kappa]N1)copper(II)]

aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey,bAksaray University, Science Education Department, 68100, Aksaray, Turkey,cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title centrosymmetric binuclear CuII complex, [Cu2(C7H4ClO2)4(C10H14N2O)2], the two CuII cations [Cu...Cu = 2.6314 (4) Å] are bridged by four 3-chlorobenzoate (CB) anions. The four carboxylate O atoms around each CuII cation form a distorted square-planar arrangement, the distorted square-pyramidal coordination geometry being completed by the pyridine N atom of the N,N-diethylnicotinamide (DENA) molecule. The dihedral angle between the benzene ring and the carboxylate group is 4.49 (11)° in one of the independent CB ligands and 12.00 (10)° in the other. The benzene rings of the independent CB ligands are oriented at a dihedral angle of 84.13 (6)°. In the crystal, weak C-H...O hydrogen bonds link the binuclear complex molecules into supramolecular chains running along [101].

Related literature

For niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For N,N-diethylnicotinamide, see: Bigoli et al. (1972[Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.]). For related structures, see: Speier & Fulop (1989[Speier, G. & Fulop, V. (1989). J. Chem. Soc. Dalton Trans. pp. 2331-2333.]); Usubaliev et al. (1980[Usubaliev, B. T., Movsumov, E. M., Musaev, F. N., Nadzhafov, G. N., Amiraslanov, I. R. & Mamedov, Kh. S. (1980). Koord. Khim. 6, 1091-1096.]); Hökelek et al. (1995[Hökelek, T., Necefoglu, H. & Balci, M. (1995). Acta Cryst. C51, 2020-2023.]); Hökelek et al. (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., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009c). Acta Cryst. E65, m1582-m1583.], 2011[Hökelek, T., Saglam, E. G., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2011). Acta Cryst. E67, m28-m29.]); Necefoglu et al. (2010a[Necefoglu, H., Çimen, E., Tercan, B., Dal, H. & Hökelek, T. (2010a). Acta Cryst. E66, m334-m335.],b[Necefoglu, H., Çimen, E., Tercan, B., Dal, H. & Hökelek, T. (2010b). Acta Cryst. E66, m485-m486.]); Aydin et al. (2012[Aydin, Ö., Çaylak Delibas, N., Necefoglu, H. & Hökelek, T. (2012). Acta Cryst. E68, m409-m410.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu2(C7H4ClO2)4(C10H14N2O)2]

  • Mr = 1105.75

  • Monoclinic, P 21 /c

  • a = 12.6077 (4) Å

  • b = 16.7569 (5) Å

  • c = 12.1402 (4) Å

  • [beta] = 99.647 (2)°

  • V = 2528.54 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.11 mm-1

  • T = 296 K

  • 0.35 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART BREEZE CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.711, Tmax = 0.724

  • 78293 measured reflections

  • 5166 independent reflections

  • 4702 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.083

  • S = 1.04

  • 5166 reflections

  • 309 parameters

  • 85 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Selected bond lengths (Å)

Cu1-O1 1.9791 (13)
Cu1-O2i 1.9688 (13)
Cu1-O3 1.9755 (13)
Cu1-O4i 1.9703 (13)
Cu1-N1 2.1454 (14)
Symmetry code: (i) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17...O5ii 0.93 2.45 3.221 (3) 140
Symmetry code: (ii) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. 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: XU5716 ).


Acknowledgements

The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State Planning Organization).

References

Aydin, Ö., Çaylak Delibas, N., Necefoglu, H. & Hökelek, T. (2012). Acta Cryst. E68, m409-m410.  [CSD] [CrossRef] [IUCr Journals]
Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962-966.  [CrossRef] [ChemPort] [IUCr Journals] [Web of Science]
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009c). Acta Cryst. E65, m1582-m1583.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Necefoglu, H. & Balci, M. (1995). Acta Cryst. C51, 2020-2023.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Saglam, E. G., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2011). Acta Cryst. E67, m28-m29.  [CrossRef] [IUCr Journals]
Hökelek, T., Yilmaz, F., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009a). Acta Cryst. E65, m955-m956.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Yilmaz, F., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009b). Acta Cryst. E65, m1328-m1329.  [CSD] [CrossRef] [IUCr Journals]
Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.  [ChemPort] [PubMed]
Necefoglu, H., Çimen, E., Tercan, B., Dal, H. & Hökelek, T. (2010a). Acta Cryst. E66, m334-m335.  [CSD] [CrossRef] [IUCr Journals]
Necefoglu, H., Çimen, E., Tercan, B., Dal, H. & Hökelek, T. (2010b). Acta Cryst. E66, m485-m486.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Speier, G. & Fulop, V. (1989). J. Chem. Soc. Dalton Trans. pp. 2331-2333.  [CrossRef]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Usubaliev, B. T., Movsumov, E. M., Musaev, F. N., Nadzhafov, G. N., Amiraslanov, I. R. & Mamedov, Kh. S. (1980). Koord. Khim. 6, 1091-1096.  [ChemPort]


Acta Cryst (2013). E69, m431-m432   [ doi:10.1107/S1600536813017881 ]

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