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Volume 69 
Part 1 
Pages o92-o93  
January 2013  

Received 4 December 2012
Accepted 11 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.094
Data-to-parameter ratio = 11.1
Details
Open access

2,3-Diaminopyridinium hydrogen malonate

aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

In the title molecular salt, C5H8N3+·C3H3O4-, the cation is essentially planar, with a maximum deviation of 0.005 (1) Å for all non-H atoms. In the anion, an intramolecular O-H...O hydrogen bond generates an S(6) ring. In the crystal, the cations and anions are connected via N-H...O hydrogen bonds and a weak C-H...O interaction, forming layers parallel to the ab plane.

Related literature

For backgroup to the chemistry of substituted pyridines, see: Amr et al. (2006[Amr, A. G., Mohamed, A. M., Mohamed, S. F., Abdel-Hafez, N. A. & Hammam, A. G. (2006). Bioorg. Med. Chem. 14, 5481-5488.]); Bart et al. (2001[Bart, A., Jansen, J., Zwan, J. V., Dulk, H., Brouwer, J. & Reedijk, J. (2001). J. Med. Chem. 44, 245-249.]); Shinkai et al. (2000[Shinkai, H., Ito, T., Iida, T., Kitao, Y., Yamada, H. & Uchida, I. (2000). J. Med. Chem. 43, 4667-4677.]). For related structures, see: Betz et al. (2011[Betz, R., Gerber, T., Hosten, E. & Schalekamp, H. (2011). Acta Cryst. E67, o2154.]); Hemamalini et al. (2011[Hemamalini, M., Goh, J. H. & Fun, H.-K. (2011). Acta Cryst. E67, o3121.]); Balasubramani & Fun (2009[Balasubramani, K. & Fun, H.-K. (2009). Acta Cryst. E65, o1519.]); Fun & Balasubramani (2009[Fun, H.-K. & Balasubramani, K. (2009). Acta Cryst. E65, o1496-o1497.]). For the conformation of the malonate ion, see: Djinovic et al. (1990[Djinovic, K., Golic, L. & Leban, I. (1990). Acta Cryst. C46, 281-286.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). 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.]). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C5H8N3+·C3H3O4-

  • Mr = 213.20

  • Monoclinic, P 21

  • a = 5.0843 (1) Å

  • b = 8.0771 (1) Å

  • c = 11.1928 (2) Å

  • [beta] = 91.214 (1)°

  • V = 459.55 (1) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 100 K

  • 0.28 × 0.25 × 0.14 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.983

  • 6631 measured reflections

  • 1778 independent reflections

  • 1695 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.094

  • S = 1.07

  • 1778 reflections

  • 160 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H1O3...O1 0.93 (4) 1.63 (3) 2.5208 (16) 159 (3)
N3-H2N3...O4i 0.88 (3) 2.16 (3) 2.9133 (19) 143 (2)
N2-H2N2...O2ii 0.87 (3) 2.15 (3) 3.0066 (18) 168 (2)
N1-H1N1...O1iii 0.92 (3) 1.87 (3) 2.7782 (16) 168 (3)
N2-H1N2...O2iii 0.88 (3) 2.12 (3) 2.9470 (18) 157 (3)
N3-H1N3...O2ii 0.87 (2) 2.18 (2) 3.0574 (19) 178 (3)
C7-H7B...O2iv 0.99 2.46 3.3532 (19) 149
Symmetry codes: (i) x-1, y+1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) x+1, y, z; (iv) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: IS5228 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant No. 304/PFIZIK/6312078 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS-USM fellowship.

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.
Amr, A. G., Mohamed, A. M., Mohamed, S. F., Abdel-Hafez, N. A. & Hammam, A. G. (2006). Bioorg. Med. Chem. 14, 5481-5488.  [CrossRef] [PubMed] [ChemPort]
Balasubramani, K. & Fun, H.-K. (2009). Acta Cryst. E65, o1519.  [CSD] [CrossRef] [details]
Bart, A., Jansen, J., Zwan, J. V., Dulk, H., Brouwer, J. & Reedijk, J. (2001). J. Med. Chem. 44, 245-249.  [ISI] [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Betz, R., Gerber, T., Hosten, E. & Schalekamp, H. (2011). Acta Cryst. E67, o2154.  [CSD] [CrossRef] [details]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Djinovic, K., Golic, L. & Leban, I. (1990). Acta Cryst. C46, 281-286.  [CrossRef] [details]
Fun, H.-K. & Balasubramani, K. (2009). Acta Cryst. E65, o1496-o1497.  [CSD] [CrossRef] [ChemPort] [details]
Hemamalini, M., Goh, J. H. & Fun, H.-K. (2011). Acta Cryst. E67, o3121.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shinkai, H., Ito, T., Iida, T., Kitao, Y., Yamada, H. & Uchida, I. (2000). J. Med. Chem. 43, 4667-4677.  [ISI] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o92-o93   [ doi:10.1107/S1600536812050386 ]

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