(IUCr) 5-Chloro-2-methoxyanilinium nitrate

Volume 64
Part 5
Page o801
May 2008

Received 16 February 2008
Accepted 1 April 2008
Online 4 April 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.109
Data-to-parameter ratio = 16.5
Details

5-Chloro-2-methoxyanilinium nitrate

Hanene Hemissi,^a Sonia Abid ^a ^* and Mohamed Rzaigui ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
Correspondence e-mail: sonia.abid@fsb.rnu.tn

The title salt, C₇H₉ClNO⁺·NO₃^-, exhibits extensive hydrogen bonding between the ammonium functional group and the nitrate anion. A two-dimensional network of bifurcated N-HO hydrogen bonds generates corrugated layers in the bc plane. The organic molecules are stacked in a parallel orientation as a result of [pi] - [pi] interactions, with an inter-ring distance of 3.837 Å.

Related literature

For related literature, see: Abid et al. (2007); Aloui et al. (2002); Desiraju & Steiner (1999); Hemissi et al. (2005); Jayaraman et al. (2002); Ouslati & Ben Nasr (2006); Steiner (2002); Kefi et al. (2007).

Experimental

Crystal data

C₇H₉ClNO⁺·NO₃^-
M_r = 220.61
Monoclinic, P 2₁ /c
a = 10.681 (2) Å
b = 9.474 (3) Å
c = 9.802 (3) Å
= 102.38 (3)°
V = 968.8 (5) Å³
Z = 4
Mo K radiation
= 0.39 mm^-1
T = 293 (2) K
0.2 × 0.18 × 0.16 mm

Data collection

Enraf-Nonius TurboCAD-4 diffractometer
Absorption correction: none
4244 measured reflections
2125 independent reflections
1409 reflections with I > 2(I)
R_int = 0.029
2 standard reflections frequency: 120 min intensity decay: 5%

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.109
S = 1.02
2125 reflections
129 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1O1ⁱ	0.89	2.08	2.967 (3)	173
N2-H1O2ⁱ	0.89	2.57	3.103 (3)	120
N2-H2O1	0.89	2.04	2.927 (3)	171
N2-H2O3	0.89	2.38	3.043 (3)	131
N2-H3O2ⁱⁱ	0.89	2.55	3.240 (3)	135
N2-H3O3ⁱⁱ	0.89	2.07	2.939 (3)	165
C7-H9O2ⁱⁱⁱ	0.96	2.42	3.361 (4)	167
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y+1, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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, 1997), DIAMOND (Brandenburg, 1998); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2102 ).

References

Abid, S., Hemissi, H. & Rzaigui, M. (2007). Acta Cryst. E63, o3117.
Aloui, Z., Abid, S. & Rzaigui, M. (2002). Mater. Res. Bull. 37, 697-703.
Brandenburg, K. (1998). DIAMOND. University of Bonn, Germany.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond. Oxford University Press.
Enraf-Nonius (1994). CAD-4 EXPRESS Software. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Hemissi, H., Abid, S. & Rzaigui, M. (2005). Anal. Sci. 21, 137-138.
Jayaraman, K., Choudhury, A. & Rao, C. N. R. (2002). Solid State Sci. 4, 413-422.
Kefi, R., Abid, S., Ben Nasr, C. & Rzaigui, M. (2007). Mater. Res. Bull. 42, 404-412.
Ouslati, A. & Ben Nasr, C. (2006). Anal. Sci. 22, 1-2.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.

organic compounds