1-(4-Nitro­phen­yl)-1H-imidazol-3-ium chloride

Ibrahim, H.; Bala, M.D.

doi:10.1107/S1600536812050878

Volume 69
Part 1
Page o114
January 2013

Received 19 October 2012
Accepted 14 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.029
wR = 0.076
Data-to-parameter ratio = 15.8
Details

1-(4-Nitrophenyl)-1H-imidazol-3-ium chloride

Halliru Ibrahim ^a and Muhammad D. Bala ^a ^*

^aSchool of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
Correspondence e-mail: bala@ukzn.ac.za

In the title salt, C₉H₈N₃O₂⁺·Cl^-, the least-squares planes of the imidazolium and benzene rings are almost coplanar, making a dihedral angle of 4.59 (1)°. In the crystal, the chloride anion links the organic molecules through N-HCl hydrogen bonds, forming chains that run diagonally across the bc face, which compliment strong C-HO hydrogen bonds between neighbouring molecules. These chains are connected to adjacent chains through two weak C-HCl interactions, resulting in hydrogen-bonded sheets extending along the b and c axes. The absolute structure of the title compound was determined using a Flack x parameter of 0.00 (6) and a Hooft y parameter of 0.03 (2).

Related literature

For the synthesis of the title compound, see: Gnanamgari et al. (2009); Coberan & Peris (2008); Singh et al., (2011). For the structure of imidazole with a bond to phenyl via carbon, see: Gayathri et al. (2010). For structure of imidazole with a bond to phenyl via nitrogen, see: Zheng et al. (2011). For the structure of nitrophenyl imidazole as a ligand in a complex, see: Singh et al. (2010, 2011). For related structures, see: Ishihara et al. (1992); Scheele et al., (2007). For our related work in this area, see: Ibrahim et al. (2012).

Experimental

Crystal data

C₉H₈N₃O₂⁺·Cl^-
M_r = 225.64
Orthorhombic, P n a 2₁
a = 14.6042 (8) Å
b = 12.1781 (7) Å
c = 5.6070 (3) Å
V = 997.21 (10) Å³
Z = 4
Mo K radiation
= 0.37 mm^-1
T = 173 K
0.54 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.524, T_max = 0.746
20153 measured reflections
2217 independent reflections
2120 reflections with I > 2(I)
R_int = 0.060

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.076
S = 1.09
2217 reflections
140 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), Hooft et al. (2010), Spek (2009); Hooft parameter = 0.03 (2), 856 Bijvoet pairs
Flack parameter: 0.00 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1Cl1ⁱ	0.92 (2)	2.08 (2)	2.9976 (17)	178 (2)
C9-H9Cl1	0.93	2.80	3.5898 (19)	144
C2-H2Cl1ⁱⁱ	0.93	2.52	3.4286 (17)	166
C4-H4O2ⁱ	0.93	2.29	3.181 (2)	161
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NR2034 ).

Acknowledgements

We thank the NRF and the University of KwaZulu-Natal for financial support.

References

Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA..
Coberan, R. & Peris, E. (2008). Organometallics, 27, 1954-1958.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2519.
Gnanamgari, D., Sauer, E. L. O., Schley, N. D., Butler, C., Incarvito, C. D. & Crabtree, R. H. (2009). Organometallics, 28, 321-325.
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2010). J. Appl. Cryst. 43, 665-668.
Ibrahim, H., Bala, M. D. & Omondi, B. (2012). Acta Cryst. E68, o2305.
Ishihara, M., Tonogaki, M., Ohba, S., Saito, Y., Okazaki, M., Katoh, T. & Kamiyama, K. (1992). Acta Cryst. C48, 184-188.
Scheele, U. J., Meyer, F. & Dechert, S. (2007). Tetrahedron Lett. 48, 8366-8370.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, A. K., Kumar, P., Yadav, M. & Pandey, D. S. (2010). J. Organomet. Chem. 695, 567-573.
Singh, A. K., Kumar, P., Yadav, M. & Pandey, D. S. (2011). Bull. Chem. Soc. Jpn, 84, 205-210.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zheng, Z., Geng, W.-Q., Wu, Z.-C. & Zhou, H.-P. (2011). Acta Cryst. E67, o524.

organic compounds