2,3-Diamino­pyridinium hydrogen malonate

Thanigaimani, K.; Khalib, N.C.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812050386

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.094
Data-to-parameter ratio = 11.1
Details

2,3-Diaminopyridinium hydrogen malonate

Kaliyaperumal Thanigaimani,^a Nuridayanti Che Khalib,^a Suhana Arshad ^a and Ibrahim Abdul Razak ^a ^*⁺

^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-HO hydrogen bond generates an S(6) ring. In the crystal, the cations and anions are connected via N-HO hydrogen bonds and a weak C-HO interaction, forming layers parallel to the ab plane.

Related literature

For backgroup to the chemistry of substituted pyridines, see: Amr et al. (2006); Bart et al. (2001); Shinkai et al. (2000). For related structures, see: Betz et al. (2011); Hemamalini et al. (2011); Balasubramani & Fun (2009); Fun & Balasubramani (2009). For the conformation of the malonate ion, see: Djinovic et al. (1990). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₅H₈N₃⁺·C₃H₃O₄^-
M_r = 213.20
Monoclinic, P 2₁
a = 5.0843 (1) Å
b = 8.0771 (1) Å
c = 11.1928 (2) Å
= 91.214 (1)°
V = 459.55 (1) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.966, T_max = 0.983
6631 measured reflections
1778 independent reflections
1695 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(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
_max = 0.35 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H1O3O1	0.93 (4)	1.63 (3)	2.5208 (16)	159 (3)
N3-H2N3O4ⁱ	0.88 (3)	2.16 (3)	2.9133 (19)	143 (2)
N2-H2N2O2ⁱⁱ	0.87 (3)	2.15 (3)	3.0066 (18)	168 (2)
N1-H1N1O1ⁱⁱⁱ	0.92 (3)	1.87 (3)	2.7782 (16)	168 (3)
N2-H1N2O2ⁱⁱⁱ	0.88 (3)	2.12 (3)	2.9470 (18)	157 (3)
N3-H1N3O2ⁱⁱ	0.87 (2)	2.18 (2)	3.0574 (19)	178 (3)
C7-H7BO2^iv	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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

organic compounds