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Volume 68 
Part 1 
Pages m52-m53  
January 2012  

Received 11 November 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.006 Å
R = 0.063
wR = 0.160
Data-to-parameter ratio = 16.9
Details
Open access

Aquabis(4-fluorobenzoato-[kappa]O)bis(nicotinamide-[kappa]N1)copper(II) nicotinamide hemisolvate trihydrate

aKafkas University, Department of Chemistry, 36100 Kars, Turkey, and bHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The asymmetric unit of the title compound, [Cu(C7H4FO2)2(C6H6N2O)2(H2O)]·0.5C6H6N2O·3H2O, contains two aquabis(4-fluorobenzoato)bis(nicotinamide)copper(II) molecules, one nicotinamide solvent molecule and six water molecules. The CuII ion is coordinated by two O atoms from two 4-fluorobenzoate ligands, two N atoms from two nicotinamide ligands and one water O atom in a distorted square-pyramidal geometry. In the crystal, O-H...O, O-H...N and N-H...O hydrogen bonds consolidate the crystal packing, which also exhibits [pi]-[pi] interactions between the aromatic rings [centroid-centroid distances 3.692 (2)-3.794 (2) Å].

Related literature

For general background to niacin, see: Krishnamachari (1974[Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.]). For general background to 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. (2011[Necefoglu, H., Maraci, A., Özbek, F. E., Tercan, B. & Hökelek, T. (2011). 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(C7H4FO2)2(C6H6N2O)2(H2O)]·0.5C6H6N2O·3H2O

  • Mr = 719.13

  • Monoclinic, P 21 /c

  • a = 18.4108 (4) Å

  • b = 14.8908 (3) Å

  • c = 22.8569 (5) Å

  • [beta] = 105.247 (3)°

  • V = 6045.7 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.80 mm-1

  • T = 100 K

  • 0.24 × 0.20 × 0.19 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 = 0.825, Tmax = 0.858

  • 103729 measured reflections

  • 15210 independent reflections

  • 11162 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.160

  • S = 1.12

  • 15210 reflections

  • 900 parameters

  • 34 restraints

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

  • [Delta][rho]max = 1.27 e Å-3

  • [Delta][rho]min = -1.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O18 0.86 2.10 2.929 (6) 163
N2-H2B...O4i 0.86 2.13 2.914 (5) 150
N4-H4A...O18ii 0.86 2.27 3.090 (6) 160
N4-H4B...O4iii 0.86 2.12 2.909 (5) 152
N6-H6A...O21iv 0.86 2.00 2.849 (5) 169
N6-H6B...O9v 0.86 2.18 2.925 (4) 145
N8-H8A...O16 0.86 2.44 3.285 (5) 167
N8-H8B...O9vi 0.86 2.07 2.890 (4) 160
N10-H10A...O7 0.86 2.20 3.031 (5) 163
N10-H10B...O12vii 0.86 2.10 2.897 (5) 155
O7-H71...O13vii 0.92 (3) 1.85 (3) 2.762 (4) 174 (3)
O7-H72...O14vii 0.81 (5) 2.02 (5) 2.824 (4) 174 (3)
O14-H141...N9 0.93 (4) 1.93 (4) 2.812 (4) 158 (4)
O14-H142...O5viii 0.93 (3) 1.85 (3) 2.782 (4) 177 (5)
O16-H161...O19 0.60 (4) 2.26 (3) 2.845 (6) 164 (8)
O17-H172...O6ix 0.73 (5) 2.21 (5) 2.887 (5) 156 (5)
O18-H182...O17x 0.63 (6) 2.30 (6) 2.839 (6) 145 (7)
O19-H191...O13 0.74 (5) 2.06 (5) 2.800 (6) 172 (5)
O20-H201...O18viii 0.77 2.07 2.611 (6) 128
O20-H202...O15 0.64 2.14 2.710 (5) 149
O21-H211...O2 0.91 (3) 1.91 (3) 2.807 (4) 169 (4)
O21-H212...O16xi 0.89 (4) 1.88 (5) 2.759 (5) 168 (5)
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y+1, z; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x, -y+1, -z+1; (v) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (vi) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (vii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (viii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ix) -x+1, -y+1, -z+1; (x) -x+1, -y, -z+1; (xi) -x, -y, -z+1.

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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) 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: CV5200 ).


Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for use of the diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 106 T472).

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] [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. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009a). Acta Cryst. E65, m466-m467.  [CSD] [CrossRef] [details]
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoglu, H. (2009b). Acta Cryst. E65, m607-m608.  [CrossRef] [details]
Hökelek, T., Gündüz, H. & Necefoglu, H. (1996). Acta Cryst. C52, 2470-2473.  [CrossRef] [details]
Hökelek, T. & Necefoglu, H. (1998). Acta Cryst. C54, 1242-1244.  [CrossRef] [details]
Hökelek, T. & Necefoglu, H. (2007). Acta Cryst. E63, m821-m823.  [CSD] [CrossRef] [details]
Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108-111.  [ChemPort] [PubMed]
Necefoglu, H., Maraci, A., Özbek, F. E., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, m619-m620.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, m52-m53   [ doi:10.1107/S1600536811053116 ]

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