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Volume 69 
Part 8 
Pages o1340-o1341  
August 2013  

Received 21 July 2013
Accepted 22 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.005 Å
R = 0.015
wR = 0.034
Data-to-parameter ratio = 19.8
Details
Open access

2-Hydroxymethyl-1,3-dimethyl-1H-imidazol-3-ium triiodide

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine1, 25000 , Algeria, and bLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse, Organique, PHYSYNOR, Université Constantine1, 25000 Constantine, Algeria
Correspondence e-mail: bouacida_sofiane@yahoo.fr

The crystal packing of the title salt, C6H11N2O+·I3-, can be described as consisting of alternating layers of cations and anions parallel to the (100) plane along the a-axis direction. The components are linked by O-H...I, C-H...I and C-H...O interactions, generating a three-dimensional network. The O atom deviates from the imidazol ring by 0.896 (2) Å.

Related literature

For the importance of heterocyclic compounds and their applications, see: Pandey et al. (2009[Pandey, S. K., Singh, A. & Nizamuddin, A. S. (2009). Eur. J. Med. Chem. 44, 1188-1197.]); Nasser (2000[Nasser, A. H. (2000). Molecules, 5, 826-834.]). For the biological activity of imidazole and imidazolium derivatives, see: Ucucu et al. (2001[Ucucu, U., Karaburun, N. G. & Isikdag, I. (2001). Il Farmaco, 56, 285-290.]); Dominianni et al. (1989[Dominianni, S. J., Yen, I. & Terence, T. (1989). J. Med. Chem. 32, 2301-2306.]); Ozkay et al. (2010[Ozkay, Y., Isikdag, I., Incesu, Z. & Akalin, G. (2010). Eur. J. Med. Chem. 45, 3320-3328.]). 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
  • C6H11N2O+·I3-

  • Mr = 507.87

  • Monoclinic, P 21 /c

  • a = 7.1647 (8) Å

  • b = 15.5586 (19) Å

  • c = 11.3201 (13) Å

  • [beta] = 96.026 (7)°

  • V = 1254.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 7.44 mm-1

  • T = 150 K

  • 0.24 × 0.03 × 0.02 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.781, Tmax = 1.000

  • 7061 measured reflections

  • 2222 independent reflections

  • 2104 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.015

  • wR(F2) = 0.034

  • S = 1.15

  • 2222 reflections

  • 112 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...I1i 0.82 3.03 3.741 (2) 146
C1-H1B...I3ii 0.97 3.05 3.924 (3) 151
C4-H4...O1iii 0.93 2.60 3.421 (4) 148
Symmetry codes: (i) x+1, y, z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker, (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART (Bruker, 2006[Bruker, (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SMART; 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, 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: HG5333 ).


Acknowledgements

We are grateful to all personal of the research squad "Synthèse de molécules à objectif thérapeutique" of PHYSYNOR Laboratory, Université Constantine1, Algeria, for their assistance. Thanks are due to MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.

References

Bahnous, M., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2012). Acta Cryst. E68, o1391.  [CSD] [CrossRef] [IUCr Journals]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, 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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Chelghoum, M., Bahnous, M., Bouacida, S., Roisnel, T. & Belfaitah, A. (2011). Acta Cryst. E67, o1890.  [CSD] [CrossRef] [IUCr Journals]
Dominianni, S. J., Yen, I. & Terence, T. (1989). J. Med. Chem. 32, 2301-2306.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nasser, A. H. (2000). Molecules, 5, 826-834.
Ozkay, Y., Isikdag, I., Incesu, Z. & Akalin, G. (2010). Eur. J. Med. Chem. 45, 3320-3328.  [PubMed]
Pandey, S. K., Singh, A. & Nizamuddin, A. S. (2009). Eur. J. Med. Chem. 44, 1188-1197.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Ucucu, U., Karaburun, N. G. & Isikdag, I. (2001). Il Farmaco, 56, 285-290.  [PubMed] [ChemPort]
Zama, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2013). Acta Cryst. E69, o837-o838.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1340-o1341   [ doi:10.1107/S1600536813020266 ]

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