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Volume 69 
Part 5 
Page o670  
May 2013  

Received 8 March 2013
Accepted 30 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.040
wR = 0.102
Data-to-parameter ratio = 8.9
Details
Open access

3,4-Diaminopyridinium hydrogen malonate

aKathmandu University Budol, Dhulikhel 45200, Nepal, and bDepartment of Chemistry & Biology, New Mexico Highlands University, 803 University Avenue, Las Vegas, NM 87701, USA
Correspondence e-mail: surenthapa86@gmail.com

In the title salt, C5H8N3+·C3H3O4-, the 3,4-diaminopyridinium cation is almost planar, with an r.m.s. deviation of 0.02 Å. The conformation of the hydrogen malonate anion is stabilized by an intramolecular O-H...O hydrogen bond, which generates an S(6) ring. In the crystal, N-H...O hydrogen bonds link cations and anions into layers parallel to the ab plane.

Related literature

For applications of 3,4-diaminopyridine, see: Maddison et al. (2001[Maddison, P., Lang, B., Mills, K. & Newsom-Davis, J. (2001). J. Neurol. Neurosurg. Psychiatry, 70, 212-217.]); Argov (2009[Argov, Z. (2009). Curr. Opin. Neurol. 22, 493-496.]). For related structures, see: De Cires-Mejias et al. (2004[De Cires-Mejias, C., Tanase, S., Reedijk, J., Gonzalez-Vilchez, F., Vilaplana, R., Mills, A. M., Kooijman, H. & Spek, A. L. (2004). Inorg. Chim. Acta, 357, 1494-1498.]); Koleva et al. (2007[Koleva, B., Tsanev, T., Kolev, T., Mayer-Figge, H. & Sheldrick, W. S. (2007). Acta Cryst. E63, o3356.], 2008[Koleva, B., Kolev, T., Tsanev, T., Kotov, S., Mayer-Figge, H., Seidel, R. W. & Sheldrich, W. S. (2008). J. Mol. Struct. 881, 146-155.]); Fun & Balasubramani (2009[Fun, H.-K. & Balasubramani, K. (2009). Acta Cryst. E65, o1531-o1532.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C5H8N3+·C3H3O4-

  • Mr = 213.20

  • Monoclinic, P 21

  • a = 8.7761 (18) Å

  • b = 5.088 (1) Å

  • c = 10.636 (2) Å

  • [beta] = 101.381 (4)°

  • V = 465.58 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.964, Tmax = 0.976

  • 3498 measured reflections

  • 1248 independent reflections

  • 1066 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.102

  • S = 1.18

  • 1248 reflections

  • 140 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O3 0.86 1.93 2.784 (3) 175
N2-H2A...O1i 0.86 2.28 3.132 (3) 174
N2-H2B...O1ii 0.86 2.15 3.005 (3) 176
N3-H3A...O2iii 0.86 2.28 3.048 (3) 149
N3-H3B...O1ii 0.86 2.10 2.960 (3) 177
O4-H4...O2 0.91 (3) 1.55 (3) 2.442 (3) 164 (3)
Symmetry codes: (i) [-x+1, y+{\script{3\over 2}}, -z]; (ii) x-1, y+2, z; (iii) [-x+1, y+{\script{3\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5392 ).


Acknowledgements

The authors are grateful for NSF support via grants DMR 0934212 (PREM) and CHE 0832622.

References

Argov, Z. (2009). Curr. Opin. Neurol. 22, 493-496.  [ISI] [CrossRef] [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
De Cires-Mejias, C., Tanase, S., Reedijk, J., Gonzalez-Vilchez, F., Vilaplana, R., Mills, A. M., Kooijman, H. & Spek, A. L. (2004). Inorg. Chim. Acta, 357, 1494-1498.  [ISI] [CSD] [CrossRef] [ChemPort]
Fun, H.-K. & Balasubramani, K. (2009). Acta Cryst. E65, o1531-o1532.  [CSD] [CrossRef] [ChemPort] [details]
Koleva, B., Kolev, T., Tsanev, T., Kotov, S., Mayer-Figge, H., Seidel, R. W. & Sheldrich, W. S. (2008). J. Mol. Struct. 881, 146-155.  [ISI] [CSD] [CrossRef] [ChemPort]
Koleva, B., Tsanev, T., Kolev, T., Mayer-Figge, H. & Sheldrick, W. S. (2007). Acta Cryst. E63, o3356.  [CSD] [CrossRef] [details]
Maddison, P., Lang, B., Mills, K. & Newsom-Davis, J. (2001). J. Neurol. Neurosurg. Psychiatry, 70, 212-217.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o670  [ doi:10.1107/S1600536813008763 ]

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