4-Nitro­anilinium triiodide monohydrate

Billing, D.G.; Black, R.S.; Hexana, W.M.

doi:10.1107/S1600536810014674

Volume 66
Part 5
Page o1186
May 2010

Received 4 March 2010
Accepted 21 April 2010
Online 28 April 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R = 0.034
wR = 0.081
Data-to-parameter ratio = 23.0
Details

4-Nitroanilinium triiodide monohydrate

David G. Billing,^a ^* Robert S. Black ^a and Wonga M. Hexana ^a

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private bag, PO Wits 2050, South Africa
Correspondence e-mail: dave.billing@wits.ac.za

In the title compound, C₆H₇N₂O₂⁺·I₃^-·H₂O, the triiodide anions form two-dimensional sheets along the a and c axes. These sheets are separated by the 4-nitroanilinium cations and water molecules, which form part of an extended hydrogen-bonded chain with the triiodide along the c axis, represented by the graph set C₃³(14). The second important hydrogen-bonding interaction is between the nitro group, the water molecule and the anilinium group, which forms an R₂²(6) ring and may be the reason for the deviation of the torsion angle between the benzene ring and the nitro group from 180 to 163.2 (4)°. These two strong hydrogen-bonding interactions also cause the benzene rings to pack off-centre from one another, with an edge-on-edge [pi] - [pi] stacking distance of 3.634 (6) Å and a centroid-centroid separation of 4.843 (2) Å.

Related literature

For structures of 4-nitroanilinine-monohalide salts, see: Lemmerer & Billing (2006) (bromine) and Ploug-Sørensen & Andersen (1982) (chlorine). For other amine-based triiodide salts, see: Tebbe & Loukili (1998). For a triiodide salt containing a tetraphenylphosphonium cation, see: Parvez et al. (1996). For structure-properties relationships in trihalides, see: Shibaeva & Yagubskii (2004). For graph-set analysis, see: Etter et al. (1990).

Experimental

Crystal data

C₆H₇N₂O₂⁺·I₃^-·H₂O
M_r = 537.85
Monoclinic, P 2₁ /c
a = 4.8429 (9) Å
b = 14.701 (3) Å
c = 18.346 (3) Å
= 91.916 (3)°
V = 1305.4 (4) Å³
Z = 4
Mo K radiation
= 7.17 mm^-1
T = 298 K
0.54 × 0.31 × 0.11 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 1999) T_min = 0.113, T_max = 0.506
8741 measured reflections
3150 independent reflections
2461 reflections with I > 2(I)
R_int = 0.068

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.081
S = 1.05
3150 reflections
137 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.71 e Å^-3
_min = -1.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO3ⁱ	0.89	1.94	2.824 (5)	173
N2-H2BI3ⁱⁱ	0.89	3.01	3.731 (4)	139
N2-H2CO1ⁱⁱⁱ	0.89	2.52	2.922 (5)	108
N2-H2CO3ⁱⁱⁱ	0.89	2.02	2.860 (5)	157
O3-H3AO2	0.88 (2)	1.98 (3)	2.818 (5)	158 (6)
O3-H3BI1^iv	0.89 (5)	2.88 (5)	3.722 (3)	157 (4)
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z.

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2032 ).

Acknowledgements

The University of the Witwatersrand and the National Research Fund (GUN: 2069064) are thanked for the award of a research grant and for providing the infrastructure required to do this work.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (1998). SMART-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT-Plus (includes XPREP). Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Lemmerer, A. & Billing, D. G. (2006). Acta Cryst. E62, o1562-o1564.
Parvez, M., Wang, M. & Boorman, P. M. (1996). Acta Cryst. C52, 377-378.
Ploug-Sørensen, G. & Andersen, E. K. (1982). Acta Cryst. B38, 671-673.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shibaeva, R. P. & Yagubskii, E. B. (2004). Chem. Rev. 104, 5347-5378
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tebbe, K. F. & Loukili, R. (1998). Z. Anorg. Allg. Chem. 624, 1175-1186.

organic compounds