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Volume 68 
Part 12 
Page o3361  
December 2012  

Received 11 October 2012
Accepted 7 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.122
Data-to-parameter ratio = 16.5
Details
Open access

4-Aminopyridinium 2-chloro-4-nitrobenzoate monohydrate

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, PO Wits 2050, South Africa
Correspondence e-mail: andreas.lemmerer@wits.ac.za

In the title hydrated molecular salt, C5H7N2+·C7H3ClNO4-·H2O, the ions and water molecules assemble into ribbons of R65(22) rings along the c axis via O(water)-H...O-, N+-H...O(water) and N-H...O- hydrogen bonds. N-H...O- hydrogen bonds connect adjacent ribbons along the c-axis direction via R44(12) rings, forming hydrogen-bonded layers. The CO2 and NO2 groups make dihedral angles of 81.8 (2) and 1.4 (2)°, respectively, with the ring in the anion.

Related literature

For related structures, see: Lemmerer et al. (2010[Lemmerer, A., Esterhuysen, C. & Bernstein, J. (2010). J. Pharm. Sci. 99, 4054-4071.]). 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. 35, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C5H7N2+·C7H3ClNO4-·H2O

  • Mr = 313.7

  • Monoclinic, P 21 /c

  • a = 14.4500 (5) Å

  • b = 14.3300 (5) Å

  • c = 6.9918 (2) Å

  • [beta] = 97.804 (2)°

  • V = 1434.37 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 173 K

  • 0.78 × 0.31 × 0.09 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: integration (XPREP; Bruker, 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.896, Tmax = 0.977

  • 14928 measured reflections

  • 3456 independent reflections

  • 2685 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.122

  • S = 1.04

  • 3456 reflections

  • 210 parameters

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

  • [Delta][rho]max = 0.5 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1Wi 0.93 (3) 1.72 (3) 2.641 (2) 170 (2)
N3-H3A...O1 0.94 (2) 1.99 (2) 2.926 (2) 171.1 (19)
N3-H3B...O2ii 0.84 (2) 2.16 (3) 2.982 (2) 165 (2)
O1W-H1W...O1iii 0.75 (3) 1.96 (3) 2.698 (2) 166 (3)
O1W-H2W...O2 0.78 (4) 1.99 (4) 2.729 (2) 158 (3)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+2, -y+1, -z+1; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker 2004[Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: FY2073 ).


Acknowledgements

This work was supported by the University of the Witwatersrand and the Molecular Sciences Institute, which are thanked for providing the infrastructure required to do this work, and the Friedel Sellshop grant for financial support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 35, 1555-1573.  [CrossRef] [ISI]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lemmerer, A., Esterhuysen, C. & Bernstein, J. (2010). J. Pharm. Sci. 99, 4054-4071.  [ISI] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3361  [ doi:10.1107/S1600536812046077 ]

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