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Volume 69 
Part 6 
Page m302  
June 2013  

Received 24 April 2013
Accepted 1 May 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.033
wR = 0.086
Data-to-parameter ratio = 15.2
Details
Open access

2-Amino-5-bromopyridin-1-ium (2-amino-5-bromopyridine-[kappa]N1)trichloridozincate

aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
Correspondence e-mail: kanidtha.h@psu.ac.th

The structure of the title salt, (C5H6BrN2)[ZnCl3(C5H5BrN2)], consists of discrete 2-amino-5-bromopyridin-1-ium cations and distorted tetrahedral (2-amino-5-bromopyridine)trichloridozincate anions. In the crystal, the complex anions and cations are linked via N-H...Cl hydrogen bonds into layers parallel to (101). Short Br...Cl contacts of 3.4239 (11) and 3.4503 (12) Å are observed, as well as [pi]-[pi] stacking interactions between the pyridine and pyridinium rings, with alternating centroid-to-centroid distances of 3.653 (2) and 3.845 (2) Å.

Related literature

For background to the chemistry of substituted pyridines, see: Janiak et al. (1999[Janiak, C., Deblon, S., Wu, H., Kolm, M. J., Klüfers, P., Piotrowski, H. & Mayer, P. (1999). Eur. J. Inorg. Chem. pp. 1507-1521.]); Hubrich et al. (2010[Hubrich, M., Peukert, M., Seichter, W. & Weber, E. (2010). Polyhedron, 29, 1854-1862.]); Wei et al. (2012[Wei, Z., Xie, X., Zhao, J., Huang, L. & Liu, X. (2012). Inorg. Chim. Acta, 387, 277-282.]). For the biological activities and electrochemical properties of pyridine derivatives, see: Jo et al. (2004[Jo, Y. W., Im, W. B., Rhee, J. K., Shim, M. J., Kim, W. B. & Choi, E. C. (2004). Bioorg. Med. Chem. pp. 5909-5915.]); Xiao et al. (2012[Xiao, X. W., He, Y. J., Sun, L. W., Wang, G. N., Shen, L. J., Fang, J. H. & Yang, J. P. (2012). Transition Met. Chem. pp. 1-5.]).

[Scheme 1]

Experimental

Crystal data
  • (C5H6BrN2)[ZnCl3(C5H5BrN2)]

  • Mr = 518.77

  • Monoclinic, P 21 /n

  • a = 9.4238 (4) Å

  • b = 13.6544 (6) Å

  • c = 13.5679 (6) Å

  • [beta] = 104.349 (1)°

  • V = 1691.40 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.64 mm-1

  • T = 293 K

  • 0.26 × 0.16 × 0.08 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.286, Tmax = 0.576

  • 18043 measured reflections

  • 2979 independent reflections

  • 2491 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.086

  • S = 1.02

  • 2979 reflections

  • 196 parameters

  • 5 restraints

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

  • [Delta][rho]max = 1.23 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...Cl1 0.87 (2) 2.50 (3) 3.315 (4) 156 (4)
N2-H2B...Cl2i 0.87 (2) 2.43 (2) 3.288 (4) 169 (5)
N3-H3A...Cl1ii 0.87 (2) 2.75 (4) 3.309 (4) 124 (3)
N3-H3A...Cl1iii 0.87 (2) 2.74 (4) 3.297 (4) 123 (4)
N4-H4A...Cl3iii 0.88 (2) 2.49 (3) 3.328 (4) 159 (4)
N4-H4B...Cl2iv 0.87 (2) 2.46 (3) 3.295 (4) 160 (4)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x-1, y, z; (iii) -x+1, -y, -z+1; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2739 ).


Acknowledgements

The authors express their gratitute to the Center for Innovation in Chemistry (PERCH-CIC) and the Graduate School, Prince of Songkla University, Thailand, for financial support. One of the authors (Fitriani) is grateful to the Directorate General of Higher Education (DGHE) of Indonesia and Brawijaya University, Indonesia, for financial assistance and a DGHE postgraduate scholarship.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hubrich, M., Peukert, M., Seichter, W. & Weber, E. (2010). Polyhedron, 29, 1854-1862.  [ISI] [CSD] [CrossRef] [ChemPort]
Janiak, C., Deblon, S., Wu, H., Kolm, M. J., Klüfers, P., Piotrowski, H. & Mayer, P. (1999). Eur. J. Inorg. Chem. pp. 1507-1521.  [CrossRef]
Jo, Y. W., Im, W. B., Rhee, J. K., Shim, M. J., Kim, W. B. & Choi, E. C. (2004). Bioorg. Med. Chem. pp. 5909-5915.  [CrossRef]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wei, Z., Xie, X., Zhao, J., Huang, L. & Liu, X. (2012). Inorg. Chim. Acta, 387, 277-282.  [ISI] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Xiao, X. W., He, Y. J., Sun, L. W., Wang, G. N., Shen, L. J., Fang, J. H. & Yang, J. P. (2012). Transition Met. Chem. pp. 1-5.


Acta Cryst (2013). E69, m302  [ doi:10.1107/S1600536813011884 ]

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