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Volume 67 
Part 3 
Pages m382-m383  
March 2011  

Received 14 February 2011
Accepted 22 February 2011
Online 26 February 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.078
Data-to-parameter ratio = 17.6
Details
Open access

Bis(4-ethylbenzoato-[kappa]O)bis(nicotinamide-[kappa]N1)zinc(II)

aDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey,bDepartment of Physics, Karabük University, 78050, Karabük, Turkey, and cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The title ZnII complex, [Zn(C9H9O2)2(C6H6N2O)2], contains two 4-ethylbenzoate and two nicotinamide monodentate ligands, leading to a distorted tetrahedral coordination of the ZnII ion. The dihedral angles between the carboxylate groups and the adjacent benzene rings are 10.33 (13) and 2.38 (11)°, while opposite pyridine and benzene rings are oriented at dihedral angles of 68.46 (5) and 81.09 (6)°. In the crystal, intermolecular N-H...O hydrogen bonds link the molecules, forming a three-dimensional network. C-H...O interactions also occur as well as two weak C-H...[pi] interactions involving the benzene rings.

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: 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.]). For standard bond lengths, 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
  • [Zn(C9H9O2)2(C6H6N2O)2]

  • Mr = 607.97

  • Monoclinic, P 21 /c

  • a = 8.0601 (2) Å

  • b = 15.9736 (3) Å

  • c = 21.2568 (3) Å

  • [beta] = 94.384 (3)°

  • V = 2728.78 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.95 mm-1

  • T = 100 K

  • 0.31 × 0.30 × 0.27 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.752, Tmax = 0.763

  • 26561 measured reflections

  • 6812 independent reflections

  • 5761 reflections with I > 2[sigma](I)

  • Rint = 0.045

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

  • wR(F2) = 0.078

  • S = 1.03

  • 6812 reflections

  • 388 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H32...O4i 0.86 (2) 1.99 (2) 2.833 (2) 165 (2)
N4-H41...O5ii 0.89 (2) 2.07 (2) 2.947 (2) 169 (2)
N4-H42...O6iii 0.84 (2) 2.06 (2) 2.901 (2) 177 (2)
C6-H6...O2ii 0.95 2.59 3.412 (2) 145
C19-H19...O5ii 0.95 2.29 3.2277 (19) 168
C21-H21...O2i 0.95 2.58 3.497 (2) 161
C23-H23...O3 0.95 2.49 3.085 (2) 121
C29-H29...O5ii 0.95 2.45 3.299 (2) 149
C17-H17A...Cg1iv 0.99 2.63 3.436 (2) 139
C20-H20...Cg1v 0.95 2.77 3.603 (2) 147
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x+1, y, z; (iii) -x+3, -y+2, -z+2; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 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, 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: SU2256 ).


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 X-ray diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 108 T657).

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 (2001). 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]
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 (2011). E67, m382-m383   [ doi:10.1107/S1600536811006830 ]

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