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Volume 69 
Part 8 
Pages m458-m459  
August 2013  

Received 4 July 2013
Accepted 9 July 2013
Online 17 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.086
Data-to-parameter ratio = 27.8
Details
Open access

Aquabis(3-chlorobenzoato-[kappa]O)bis(N,N-diethylnicotinamide-[kappa]N)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

The title compound, [Cu(C7H4ClO2)2(C10H14N2O)2(H2O)], has twofold symmetry with the CuII cation and the O atom of the coordinating water molecule located on the axis. The CuII cation is coordinated by two carboxylate O atoms of chlorobenzoate (CB) anions, two N atoms of N,N-diethylnicotinamide (DENA) ligands and one water molecule in a distorted N2O3 square-pyramidal geometry. The benzene and pyridine rings are oriented at a dihedral angle of 82.51 (6)°. In the anionic ligand, the carboxylate group is twisted away from the attached benzene ring by 12.85 (11)°. In the crystal, O-H...O hydrogen bonds between the coordinating water molecule and the carboxyl group link the complex molecules into supramolecular chains running along the c-axis direction.

Related literature

For literature on niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For information on 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: Hökelek et al. (1996[Hökelek, T., Gündüz, H. & Necefoglu, H. (1996). Acta Cryst. C52, 2470-2473.], 2009a[Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009a). Acta Cryst. E65, m466-m467.],b[Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009b). Acta Cryst. E65, m607-m608.]); Hökelek & Necefoglu (1998[Hökelek, T. & Necefoglu, H. (1998). Acta Cryst. C54, 1242-1244.], 2007[Hökelek, T. & Necefoglu, H. (2007). Acta Cryst. E63, m821-m823.]); Necefoglu et al. (2011a[Necefoglu, H., Maraci, A., Aktas, V., Tercan, B. & Hökelek, T. (2011a). Acta Cryst. E67, m780-m781.],b[Necefoglu, H., Özbek, F. E., Öztürk, V., Adigüzel, V. & Hökelek, T. (2011b). Acta Cryst. E67, m1164-m1165.],c[Necefoglu, H., Maraci, A., Özbek, F. E., Tercan, B. & Hökelek, T. (2011c). Acta Cryst. E67, m619-m620.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans.2 pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C7H4ClO2)2(C10H14N2O)2(H2O)]

  • Mr = 749.13

  • Orthorhombic, I b a 2

  • a = 15.9185 (9) Å

  • b = 19.2366 (11) Å

  • c = 11.5535 (7) Å

  • V = 3537.9 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.82 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 = 0.821, Tmax = 0.884

  • 75834 measured reflections

  • 6232 independent reflections

  • 5189 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.086

  • S = 1.06

  • 6232 reflections

  • 224 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with no Friedel pairs measured

  • Flack parameter: 0.027 (10)

Table 1
Selected bond lengths (Å)

Cu1-N1 2.0294 (12)
Cu1-O1 1.9337 (10)
Cu1-O4 2.238 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H41...O2i 0.79 (4) 1.95 (3) 2.7367 (17) 171 (4)
Symmetry code: (i) [x, -y+1, z-{\script{1\over 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: XU5719 ).


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 of Planning Organization).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans.2 pp. S1-19.
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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009a). Acta Cryst. E65, m466-m467.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009b). Acta Cryst. E65, m607-m608.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Gündüz, H. & Necefoglu, H. (1996). Acta Cryst. C52, 2470-2473.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T. & Necefoglu, H. (1998). Acta Cryst. C54, 1242-1244.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T. & Necefoglu, H. (2007). Acta Cryst. E63, m821-m823.  [CSD] [CrossRef] [IUCr Journals]
Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.  [ChemPort] [PubMed]
Necefoglu, H., Maraci, A., Aktas, V., Tercan, B. & Hökelek, T. (2011a). Acta Cryst. E67, m780-m781.  [CSD] [CrossRef] [IUCr Journals]
Necefoglu, H., Maraci, A., Özbek, F. E., Tercan, B. & Hökelek, T. (2011c). Acta Cryst. E67, m619-m620.  [CSD] [CrossRef] [IUCr Journals]
Necefoglu, H., Özbek, F. E., Öztürk, V., Adigüzel, V. & Hökelek, T. (2011b). Acta Cryst. E67, m1164-m1165.  [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, m458-m459   [ doi:10.1107/S1600536813018989 ]

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