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Volume 69 
Part 9 
Pages o1429-o1430  
September 2013  

Received 21 July 2013
Accepted 8 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.027
wR = 0.068
Data-to-parameter ratio = 30.5
Details
Open access

2-Hydroxymethyl-1,3-dimethyl-1H-benzimidazol-3-ium iodide

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000, Algeria, and bLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Constantine 1, 25000 Constantine, Algeria
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the cation of the title compound, C10H13N2O+·I-, all non-H atoms, with the exception of the O atom, are essentially coplanar, with a maximum deviation of 0.04 (1) Å. In the crystal, the cations and anions are arranged in layers parallel to (100). The cations are connected to the anions via an O-H...I hydrogen bond and there are significant [pi]-[pi] stacking interactions between cation layers, with centroid-centroid distances in the range 3.606 (5)-3.630 (5) Å. A weak intramolecular C-H...O hydrogen bond is also observed. The crystal studied was an inversion twin with refined components of 0.52 (5) and 0.48 (5).

Related literature

For applications of this class of compounds, see: Tonelli et al. (2010[Tonelli, M., Simone, M., Tasso, B., Novelli, F., Boido, V., Sparatore, F., Paglietti, G., Pricl, S., Giliberti, G., Blois, S., Ibba, C., Sanna, G., Loddo, R. & Colla, P. L. (2010). Bioorg. Med. Chem. 18, 2937-2953.]); Preston (1974[Preston, P. N. (1974). Chem. Rev. 74, 279-314.]); Hazelton et al. (1995[Hazelton, J. C., Iddon, B., Suschitzky, H. & Woolley, L. H. (1995). Tetrahedron, 51, 10771-10794.]); Kucukguzel et al. (2001[Kucukguzel, I., Kucukguzel, S. G., Rollas, S. & Kiraz, M. (2001). Bioorg. Med. Chem. Lett. 11, 1703-1707.]); Islam et al. (1991[Islam, I., Skibo, E. B., Dorr, R. T. & Alberts, D. S. (1991). J. Med. Chem. 34, 2954-2961.]); Li et al. (2003[Li, Q. F., He, R. H., Jensen, J. O. & Bjerrum, N. J. (2003). Chem. Mater. 15, 4896-4915.]); Abboud et al. (2006[Abboud, Y., Abourriche, A., Saffaj, T., Berrada, M., Charrouf, M., Bennamara, A., Cherqaoui, A. & Takky, D. (2006). Appl. Surf. Sci. 252, 8178-8184.]). For our previous work on imidazole derivatives, see: Bahnous et al. (2012[Bahnous, M., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2012). Acta Cryst. E68, o1391.]); Zama et al. (2013[Zama, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2013). Acta Cryst. E69, o837-o838.]); Chelghoum et al. (2011[Chelghoum, M., Bahnous, M., Bouacida, S., Roisnel, T. & Belfaitah, A. (2011). Acta Cryst. E67, o1890.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13N2O+·I-

  • Mr = 304.12

  • Orthorhombic, P 21 n b

  • a = 6.5690 (7) Å

  • b = 10.1342 (10) Å

  • c = 16.9357 (19) Å

  • V = 1127.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.81 mm-1

  • T = 150 K

  • 0.14 × 0.13 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.647, Tmax = 0.747

  • 10018 measured reflections

  • 4002 independent reflections

  • 3243 reflections with I > 2[sigma](I)

  • Rint = 0.02

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.068

  • S = 1.05

  • 4002 reflections

  • 131 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 1.34 e Å-3

  • [Delta][rho]min = -0.72 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1518 Friedel pairs

  • Absolute structure parameter: 0.48 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...I1i 0.82 2.66 3.473 (3) 171
C5-H5A...O1 0.96 2.52 3.170 (5) 125
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker. (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker. (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CRYSCAL (T. Roisnel, local program).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5638 ).


Acknowledgements

We are grateful to all personal of the research squad `Synthèse de molécules à objectif thérapeutique' of PHYSYNOR Laboratory, Université Constantine 1, Algeria, for their assistance. Thanks are due to MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.

References

Abboud, Y., Abourriche, A., Saffaj, T., Berrada, M., Charrouf, M., Bennamara, A., Cherqaoui, A. & Takky, D. (2006). Appl. Surf. Sci. 252, 8178-8184.  [ISI] [CrossRef] [ChemPort]
Bahnous, M., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2012). Acta Cryst. E68, o1391.  [CSD] [CrossRef] [details]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker. (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Chelghoum, M., Bahnous, M., Bouacida, S., Roisnel, T. & Belfaitah, A. (2011). Acta Cryst. E67, o1890.  [CSD] [CrossRef] [details]
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]
Hazelton, J. C., Iddon, B., Suschitzky, H. & Woolley, L. H. (1995). Tetrahedron, 51, 10771-10794.  [CrossRef] [ChemPort] [ISI]
Islam, I., Skibo, E. B., Dorr, R. T. & Alberts, D. S. (1991). J. Med. Chem. 34, 2954-2961.  [CrossRef] [PubMed] [ChemPort] [ISI]
Kucukguzel, I., Kucukguzel, S. G., Rollas, S. & Kiraz, M. (2001). Bioorg. Med. Chem. Lett. 11, 1703-1707.  [PubMed] [ChemPort]
Li, Q. F., He, R. H., Jensen, J. O. & Bjerrum, N. J. (2003). Chem. Mater. 15, 4896-4915.  [ISI] [CrossRef] [ChemPort]
Preston, P. N. (1974). Chem. Rev. 74, 279-314.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Tonelli, M., Simone, M., Tasso, B., Novelli, F., Boido, V., Sparatore, F., Paglietti, G., Pricl, S., Giliberti, G., Blois, S., Ibba, C., Sanna, G., Loddo, R. & Colla, P. L. (2010). Bioorg. Med. Chem. 18, 2937-2953.  [CrossRef] [ChemPort] [PubMed]
Zama, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2013). Acta Cryst. E69, o837-o838.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1429-o1430   [ doi:10.1107/S1600536813022307 ]

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