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Volume 69 
Part 7 
Pages m356-m357  
July 2013  

Received 9 May 2013
Accepted 28 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.083
Data-to-parameter ratio = 14.8
Details
Open access

Bis(3-chlorobenzoato-[kappa]2O,O')bis(nicotinamide-[kappa]N)copper(II)

aKafkas University, Department of Chemistry, 63100 Kars, Turkey,bAksaray University, Department of Physics, 68100, Aksaray, Turkey,cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and dHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The molecule of the title CuII complex, [Cu(C7H4ClO2)2(C6H6N2O)2], contains two 3-chlorobenzoate (CB) and two nicotinamide (NA) ligands; the CB act as bidentate ligands, while the NA are monodentate ligands. The resulting CuN2O4 coordination polyhedron is a considerably distorted octahedron. The dihedral angles between the carboxylate groups and the adjacent benzene rings are 17.92 (12) and 24.69 (16)°, while the two benzene rings and the two pyridine rings are oriented at dihedral angles of 52.20 (8) and 1.56 (6)°. In the crystal, N-H...N and C-H...O hydrogen bonds link the molecules into a three-dimensional network. The [pi]-[pi] contact between the benzene rings [centroid-centroid distance = 3.982 (2) Å] may further stabilize the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For the nicotinic acid derivative 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: 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.]); Hökelek & Necefoglu (1996[Hökelek, T. & Necefouglu, H. (1996). Acta Cryst. C52, 1128-1131.]); Hökelek et al. (1996[Hökelek, T., Gündüz, H. & Necefouglu, H. (1996). Acta Cryst. C52, 2470-2473.]); Hökelek, Dal et al. (2009[Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009). Acta Cryst. E65, m651-m652.]); Hökelek, Yilmaz et al. (2009[Hökelek, T., Yilmaz, F., Tercan, B., Gürgen, F. & Necefoglu, H. (2009). Acta Cryst. E65, m1416-m1417.]); Necefoglu et al. (2011[Necefoglu, H., Özbek, F. E., Öztürk, V., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m887-m888.]); Sertçelik et al. (2013[Sertçelik, M., Çaylak Delibas, N., Necefoglu, H. & Hökelek, T. (2013). Acta Cryst. E69, m290-m291.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C7H4ClO2)2(C6H6N2O)2]

  • Mr = 618.91

  • Triclinic, [P \overline 1]

  • a = 9.6614 (2) Å

  • b = 12.5429 (3) Å

  • c = 12.8728 (3) Å

  • [alpha] = 61.598 (2)°

  • [beta] = 87.386 (3)°

  • [gamma] = 77.115 (3)°

  • V = 1334.30 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.07 mm-1

  • T = 296 K

  • 0.35 × 0.20 × 0.15 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 = 0.774, Tmax = 0.852

  • 19053 measured reflections

  • 5434 independent reflections

  • 4970 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.06

  • 5434 reflections

  • 368 parameters

  • 117 restraints

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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O2i 0.80 (2) 2.12 (2) 2.896 (2) 164 (2)
N2-H2B...O6ii 0.84 (3) 2.02 (3) 2.790 (2) 153 (2)
N4-H4A...O5i 0.83 (3) 2.01 (3) 2.817 (2) 164 (2)
N4-H4B...O4ii 0.81 (2) 2.05 (2) 2.836 (2) 162 (3)
C19-H19...O1iii 0.93 2.45 3.100 (2) 127
C21-H21...O5i 0.93 2.56 3.416 (2) 154
C24-H24...O3iv 0.93 2.59 3.475 (3) 158
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+2, -z+1; (iii) -x+1, -y+2, -z; (iv) -x, -y+2, -z.

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: RK2404 ).


Acknowledgements

The authors are indebted to Aksaray University and the Science and Technology Application and Research Center of Aksaray University, Aksaray, Turkey, for the use of X-ray diffractometer.

References

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]
Greenaway, F. T., Pazeshk, A., Cordes, A. W., Noble, M. C. & Sorenson, J. R. J. (1984). Inorg. Chim. Acta, 93, 67-71.  [CrossRef] [ChemPort] [Web of Science]
Hökelek, T., Dal, H., Tercan, B., Aybirdi, Ö. & Necefoglu, H. (2009). Acta Cryst. E65, m651-m652.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Gündüz, H. & Necefouglu, H. (1996). Acta Cryst. C52, 2470-2473.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T. & Necefouglu, H. (1996). Acta Cryst. C52, 1128-1131.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Yilmaz, F., Tercan, B., Gürgen, F. & Necefoglu, H. (2009). Acta Cryst. E65, m1416-m1417.  [CrossRef] [IUCr Journals]
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] [IUCr Journals]
Sertçelik, M., Çaylak Delibas, N., Necefoglu, H. & Hökelek, T. (2013). Acta Cryst. E69, m290-m291.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m356-m357   [ doi:10.1107/S1600536813014694 ]

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