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Volume 69 
Part 10 
Pages o1543-o1544  
October 2013  

Received 4 September 2013
Accepted 7 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.109
Data-to-parameter ratio = 12.1
Details
Open access

Amino[(1H-benzimidazol-2-yl)amino]methaniminium 4-methylbenzenesulfonate

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada E-18071, Spain,eDepartment of Chemistry, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The asymmetric unit of the title salt, C8H10N5+·C7H7O3S-, consists of two amino[(1H-benzimidazol-2-yl)amino]methaniminium cations and two 4-methylbenzenesulfonate anions. The cations are each stabilized by intramolecular N-H...N hydrogen bonds between the free amino groups and the imine N atoms of the benzimidazole units, forming S(6) ring motifs. In the crystal, cations and anions are linked by N-H...O and C-H...O hydrogen bonds, forming a three-dimensional supramolecular framework. Two strong [pi]-[pi] stacking interactions [centroid-centroid distances = 3.4112 (14) and 3.4104 (14) Å] also occur between the centroids of the imidazole rings of like cations.

Related literature

For the synthesis of guanidine-containing compounds, see: Wu et al. (2002[Wu, Y.-Q., Hamilton, S. K., Wilkinson, D. E. & Hamilton, G. S. (2002). J. Org. Chem. 67, 7553-7556.]); Hopkins et al. (2002[Hopkins, T. P., Dener, J. M. & Boldi, A. M. (2002). J. Comb. Chem. 4, 167-174.]); Kilburn et al. (2002[Kilburn, J. P., Lau, J. & Jones, R. C. F. (2002). Tetrahedron, 58, 1739-1743.]); Manimala & Anslyn (2002[Manimala, J. C. & Anslyn, E. V. (2002). Tetrahedron Lett. 43, 565-567.]). For pharmaceutical and chemical applications of guanidines, see: Han et al. (2008[Han, J.-J., Xu, Y.-F., Su, Y.-P., She, X.-P. & Pan, X.-F. (2008). Catal. Commun. 9, 2077-2079.]); Hannon & Anslyn (1993[Hannon, C. L. & Anslyn, E. V. (1993). Bioorg. Chem. Front. 3, 193-255.]); Ekelund et al. (2001[Ekelund, S., Nygren, P. & Larsson, R. (2001). Biochem. Pharmacol. 61, 1183-1193.]); Kovacevic & Maksic (2001[Kovacevic, B. & Maksic, Z. B. (2001). Org. Lett. 3, 1523-1526.]); Costa et al. (1998[Costa, M., Chiusoli, G. P., Taffurelli, D. & Dalmonego, G. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 1541-1546.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) and for standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10N5+·C7H7O3S-

  • Mr = 347.41

  • Monoclinic, P 21 /c

  • a = 12.3821 (4) Å

  • b = 17.8077 (7) Å

  • c = 14.5112 (5) Å

  • [beta] = 90.013 (2)°

  • V = 3199.7 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 100 K

  • 0.35 × 0.10 × 0.04 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 20618 measured reflections

  • 5679 independent reflections

  • 4108 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.109

  • S = 1.05

  • 5679 reflections

  • 469 parameters

  • 15 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-HN1...O1i 0.86 (2) 2.11 (2) 2.948 (3) 166 (2)
N3-HN3...O6ii 0.86 (2) 1.95 (2) 2.805 (3) 173 (2)
N6-HN6...O6iii 0.88 (2) 2.09 (2) 2.944 (3) 164 (2)
N8-HN8...O1iv 0.87 (2) 1.93 (2) 2.799 (2) 177 (2)
N4-H4A...N2 0.87 (2) 1.97 (2) 2.686 (3) 139 (2)
N4-H4B...O3 0.87 (2) 2.06 (2) 2.909 (3) 166 (2)
N5-H5A...O5ii 0.89 (2) 1.98 (2) 2.871 (3) 176 (3)
N5-H5B...O2 0.88 (2) 1.99 (2) 2.863 (3) 169 (3)
N9-H9A...N7 0.86 (2) 1.98 (2) 2.683 (3) 138 (2)
N9-H9B...O5v 0.85 (2) 2.06 (2) 2.906 (3) 174 (2)
N10-H10A...O4v 0.88 (2) 2.00 (2) 2.863 (3) 167 (3)
N10-H10B...O3iv 0.89 (2) 1.99 (2) 2.872 (3) 179 (3)
C7-H7C...O4vi 0.98 2.53 3.283 (3) 133
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) -x+1, -y+1, -z+2; (vi) x, y, z-1.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 for Windows (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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5349 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and Sohag University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Costa, M., Chiusoli, G. P., Taffurelli, D. & Dalmonego, G. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 1541-1546.  [CrossRef]
Ekelund, S., Nygren, P. & Larsson, R. (2001). Biochem. Pharmacol. 61, 1183-1193.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Han, J.-J., Xu, Y.-F., Su, Y.-P., She, X.-P. & Pan, X.-F. (2008). Catal. Commun. 9, 2077-2079.  [Web of Science] [CrossRef] [ChemPort]
Hannon, C. L. & Anslyn, E. V. (1993). Bioorg. Chem. Front. 3, 193-255.  [CrossRef] [ChemPort]
Hopkins, T. P., Dener, J. M. & Boldi, A. M. (2002). J. Comb. Chem. 4, 167-174.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Kilburn, J. P., Lau, J. & Jones, R. C. F. (2002). Tetrahedron, 58, 1739-1743.  [Web of Science] [CrossRef] [ChemPort]
Kovacevic, B. & Maksic, Z. B. (2001). Org. Lett. 3, 1523-1526.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Manimala, J. C. & Anslyn, E. V. (2002). Tetrahedron Lett. 43, 565-567.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wu, Y.-Q., Hamilton, S. K., Wilkinson, D. E. & Hamilton, G. S. (2002). J. Org. Chem. 67, 7553-7556.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1543-o1544   [ doi:10.1107/S1600536813024975 ]

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