4-Amino­pyridinium 2-chloro-4-nitro­benzoate monohydrate

Savig, K.L.; Lemmerer, A.

doi:10.1107/S1600536812046077

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 (C-C) = 0.002 Å
R = 0.043
wR = 0.122
Data-to-parameter ratio = 16.5
Details

4-Aminopyridinium 2-chloro-4-nitrobenzoate monohydrate

Kelsey L. Savig ^a and Andreas Lemmerer ^a ^*

^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)-HO^-, N⁺-HO(water) and N-HO^- hydrogen bonds. N-HO^- 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). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₅H₇N₂⁺·C₇H₃ClNO₄^-·H₂O
M_r = 313.7
Monoclinic, P 2₁ /c
a = 14.4500 (5) Å
b = 14.3300 (5) Å
c = 6.9918 (2) Å
= 97.804 (2)°
V = 1434.37 (8) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.896, T_max = 0.977
14928 measured reflections
3456 independent reflections
2685 reflections with I > 2(I)
R_int = 0.061

Refinement

R[F² > 2(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
_max = 0.5 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1Wⁱ	0.93 (3)	1.72 (3)	2.641 (2)	170 (2)
N3-H3AO1	0.94 (2)	1.99 (2)	2.926 (2)	171.1 (19)
N3-H3BO2ⁱⁱ	0.84 (2)	2.16 (3)	2.982 (2)	165 (2)
O1W-H1WO1ⁱⁱⁱ	0.75 (3)	1.96 (3)	2.698 (2)	166 (3)
O1W-H2WO2	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); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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.
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.
Lemmerer, A., Esterhuysen, C. & Bernstein, J. (2010). J. Pharm. Sci. 99, 4054-4071.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds