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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 [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.076
Data-to-parameter ratio = 15.8
Details
Open access

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

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-H...Cl hydrogen bonds, forming chains that run diagonally across the bc face, which compliment strong C-H...O hydrogen bonds between neighbouring molecules. These chains are connected to adjacent chains through two weak C-H...Cl 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[Gnanamgari, D., Sauer, E. L. O., Schley, N. D., Butler, C., Incarvito, C. D. & Crabtree, R. H. (2009). Organometallics, 28, 321-325.]); Coberan & Peris (2008[Coberan, R. & Peris, E. (2008). Organometallics, 27, 1954-1958.]); Singh et al., (2011[Singh, A. K., Kumar, P., Yadav, M. & Pandey, D. S. (2011). Bull. Chem. Soc. Jpn, 84, 205-210.]). For the structure of imidazole with a bond to phenyl via carbon, see: Gayathri et al. (2010[Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2519.]). For structure of imidazole with a bond to phenyl via nitrogen, see: Zheng et al. (2011[Zheng, Z., Geng, W.-Q., Wu, Z.-C. & Zhou, H.-P. (2011). Acta Cryst. E67, o524.]). For the structure of nitrophenyl imidazole as a ligand in a complex, see: Singh et al. (2010[Singh, A. K., Kumar, P., Yadav, M. & Pandey, D. S. (2010). J. Organomet. Chem. 695, 567-573.], 2011[Singh, A. K., Kumar, P., Yadav, M. & Pandey, D. S. (2011). Bull. Chem. Soc. Jpn, 84, 205-210.]). For related structures, see: Ishihara et al. (1992[Ishihara, M., Tonogaki, M., Ohba, S., Saito, Y., Okazaki, M., Katoh, T. & Kamiyama, K. (1992). Acta Cryst. C48, 184-188.]); Scheele et al., (2007[Scheele, U. J., Meyer, F. & Dechert, S. (2007). Tetrahedron Lett. 48, 8366-8370.]). For our related work in this area, see: Ibrahim et al. (2012[Ibrahim, H., Bala, M. D. & Omondi, B. (2012). Acta Cryst. E68, o2305.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8N3O2+·Cl-

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA..]) Tmin = 0.524, Tmax = 0.746

  • 20153 measured reflections

  • 2217 independent reflections

  • 2120 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), Hooft et al. (2010[Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2010). J. Appl. Cryst. 43, 665-668.]), Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); Hooft parameter = 0.03 (2), 856 Bijvoet pairs

  • Flack parameter: 0.00 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...Cl1i 0.92 (2) 2.08 (2) 2.9976 (17) 178 (2)
C9-H9...Cl1 0.93 2.80 3.5898 (19) 144
C2-H2...Cl1ii 0.93 2.52 3.4286 (17) 166
C4-H4...O2i 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[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA..]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA..]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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


Acta Cryst (2013). E69, o114  [ doi:10.1107/S1600536812050878 ]

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