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Volume 65 
Part 4 
Pages o748-o749  
April 2009  

Received 25 February 2009
Accepted 27 February 2009
Online 14 March 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.034
wR = 0.096
Data-to-parameter ratio = 15.5
Details
Open access

Bis(4-aminopyridinium) bis(hydrogen oxalate) monohydrate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Physics, National Institute of Technology, Tiruchirappalli 620015, India
Correspondence e-mail: hkfun@usm.my

In the title compound, 2C5H7N2+·2C2HO4-·H2O, the asymmetric unit consists of an aminopyridinium cation, an oxalic actetate anion and a half-molecule of water, which lies on a two-fold rotation axis. The crystal packing is consolidated by intermolecular O-H...O, N-H...O and C-H...O hydrogen bonds. The molecules are linked into an infinite one dimensional chain along [010].

Related literature

For the biological activity of 4-aminopyridine, see: Judge & Bever (2006[Judge, S. & Bever, C. (2006). Pharmacol. Ther. 111, 224-259.]); Schwid et al. (1997[Schwid, S. B., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817-821.]); Strupp et al. (2004[Strupp, M., Kalla, R., Dichgans, M., Fraitinger, T., Glasauer, S. & Brandt, T. (2004). Neurology, 62, 1623-1625.]). For the structure of oxalic acid, see: Derissen & Smith (1974[Derissen, J. L. & Smith, P. H. (1974). Acta Cryst. B30, 2240-2242.]). For related structures, see: Anderson et al. (2005[Anderson, F. P., Gallagher, J. F., Kenny, P. T. M. & Lough, A. J. (2005). Acta Cryst. E61, o1350-o1353.]); Bhattacharya et al. (1994[Bhattacharya, S., Dastidar, P. & Guru Row, T. N. (1994). Chem. Mater. 6, 531-537.]); Chao & Schempp (1977[Chao, M. & Schempp, E. (1977). Acta Cryst. B33, 1557-1564.]); Karle et al. (2003[Karle, I., Gilardi, R. D., Chandrashekhar Rao, Ch., Muraleedharan, K. M. & Ranganathan, S. (2003). J. Chem. Crystallogr. 33, 727-749.]). For stability of the temperature controller, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • 2C5H7N2+·2C2HO4-·H2O

  • Mr = 386.32

  • Monoclinic, C 2/c

  • a = 15.6429 (6) Å

  • b = 5.6929 (2) Å

  • c = 19.9091 (7) Å

  • [beta] = 105.617 (2)°

  • V = 1707.52 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 100 K

  • 0.49 × 0.34 × 0.11 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.906, Tmax = 0.986

  • 12438 measured reflections

  • 2467 independent reflections

  • 2159 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.096

  • S = 1.03

  • 2467 reflections

  • 159 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H2W1...O4i 0.874 (18) 1.895 (18) 2.7676 (9) 175.0 (18)
N2-H1N2...O4ii 0.877 (15) 1.983 (16) 2.8556 (11) 173.4 (14)
N2-H2N2...O1Wiii 0.890 (16) 1.993 (15) 2.8620 (12) 164.8 (13)
N1-H1N1...O3iv 0.863 (17) 2.100 (17) 2.8645 (11) 147.3 (15)
N1-H1N1...O2iv 0.863 (17) 2.218 (17) 2.8818 (11) 133.6 (15)
O1-H1O1...O3v 1.00 (2) 1.60 (2) 2.5916 (10) 177.6 (18)
C5-H5...O2vi 0.951 (13) 2.361 (14) 3.1585 (12) 141.2 (11)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x, -y+1, z+{\script{1\over 2}}]; (iii) x, y+1, z; (iv) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (v) x, y-1, z; (vi) [x-{\script{1\over 2}}, y+{\script{3\over 2}}, z].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. 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: AT2732 ).


Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No.1001/PFIZIK/811012.

References

Anderson, F. P., Gallagher, J. F., Kenny, P. T. M. & Lough, A. J. (2005). Acta Cryst. E61, o1350-o1353.  [CrossRef] [details]
Bhattacharya, S., Dastidar, P. & Guru Row, T. N. (1994). Chem. Mater. 6, 531-537.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chao, M. & Schempp, E. (1977). Acta Cryst. B33, 1557-1564.  [CrossRef] [details] [ISI]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Derissen, J. L. & Smith, P. H. (1974). Acta Cryst. B30, 2240-2242.  [CrossRef] [details] [ISI]
Judge, S. & Bever, C. (2006). Pharmacol. Ther. 111, 224-259.  [CrossRef] [PubMed] [ChemPort]
Karle, I., Gilardi, R. D., Chandrashekhar Rao, Ch., Muraleedharan, K. M. & Ranganathan, S. (2003). J. Chem. Crystallogr. 33, 727-749.  [ISI] [CSD] [CrossRef] [ChemPort]
Schwid, S. B., Petrie, M. D., McDermott, M. P., Tierney, D. S., Mason, D. H. & Goodman, A. D. (1997). Neurology, 48, 817-821.  [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Strupp, M., Kalla, R., Dichgans, M., Fraitinger, T., Glasauer, S. & Brandt, T. (2004). Neurology, 62, 1623-1625.  [ISI] [PubMed] [ChemPort]


Acta Cryst (2009). E65, o748-o749   [ doi:10.1107/S1600536809007247 ]

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