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Volume 67 
Part 9 
Pages o2490-o2491  
September 2011  

Received 8 August 2011
Accepted 23 August 2011
Online 27 August 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.113
Data-to-parameter ratio = 14.6
Details
Open access

2-Methyl-5-nitro-1H-benzimidazol-6-amine dihydrate

Sebla Dinçer,a Hakan Dalb and Tuncer Hökelekc*

aAnkara University, Department of Chemistry, 06100 Tandogan, Ankara, Turkey,bAnadolu University, Faculty of Science, Department of Chemistry, 26470 Yenibaglar, Eskisehir, Turkey, and cHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The title benzimidazole molecule, C8H8N4O2·2H2O, is planar with a maximum deviation of 0.079 (2) Å (for one of the O atoms in the nitro group). It crystallized as a dihydrate and intermolecular O-H...O and N-H...O hydrogen bonds link the uncoordinated water molecules, and the nitro and amine groups, respectively. In the crystal, N-H...O, O-H...N, O-H...O and C-H...O hydrogen bonds link the molecules to form a three-dimensional network. A [pi]-[pi] contact between the benzene rings, [centroid-centroid distance = 3.588 (1) Å] may further stabilize the crystal structure.

Related literature

For the antitumor, antihelmintic, antibacterial, virucidal and fungucidal properties of benzimidazole derivatives, see: Refaat (2010[Refaat, H. M. (2010). Eur. J. Med. Chem. 45, 2949-2956.]); Laryea et al. (2010[Laryea, D., Gullbo, J., Isakssoon, A., Larsson, R. & Nygren, P. (2010). Anti-Cancer Drugs, 21, 33-42.]); Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]); Spasov et al. (1999[Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.]); Soula & Luu-Duc (1986[Soula, C. & Luu-Duc, C. (1986). Lyon Pharm. 37, 297-302.]). For the coordination and corrosion inhibitor abilities of benzimidazoles, see: Kuznetsov & Kazansky (2008[Kuznetsov, Y. I. & Kazansky, L. P. (2008). Russ. Chem. Rev. 77, 219-232.]); Subramanyam & Mayanna (1985[Subramanyam, N. C. & Mayanna, S. M. (1985). Corros. Sci. 25, 163-169.]). For the use of benzimidazole derivatives as photographic materials and dyes, see: Hoffmann et al. (2011[Hoffmann, H. S., Stefani, V., Benvenutti, E. V., Costa, T. M. H. & Gallas, M. R. (2011). Mater. Chem. Phys. 126, 97-101.]); Alamgir et al. (2007[Alamgir, M., Black, D. S. C. & Kumar, N. (2007). Top. Heterocycl. Chem. 9, 87-118.]). For related structures, see: Hökelek et al. (2002[Hökelek, T., Dinçer, S. & Kiliç, E. (2002). Cryst. Res. Technol. 37, 1138-1142.]); Dinçer et al. (2011[Dinçer, S., Gönülalan, G., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, o806-o807.]).

[Scheme 1]

Experimental

Crystal data

  • C8H8N4O2·2H2O

  • Mr = 228.22

  • Triclinic, [P \overline 1]

  • a = 7.0475 (3) Å

  • b = 7.2801 (3) Å

  • c = 10.9906 (4) Å

  • [alpha] = 76.754 (3)°

  • [beta] = 71.686 (2)°

  • [gamma] = 71.809 (2)°

  • V = 503.18 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.43 × 0.19 × 0.10 mm
Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.988

  • 8838 measured reflections

  • 2533 independent reflections

  • 1800 reflections with I > 2[sigma](I)

  • Rint = 0.036
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.113

  • S = 1.03

  • 2533 reflections

  • 174 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...O3i 0.94 (2) 1.87 (2) 2.7735 (18) 160.4 (19)
N2-H21...O1ii 0.88 (2) 2.39 (2) 3.2212 (18) 158.8 (17)
N2-H21...O4iii 0.88 (2) 2.59 (2) 3.163 (2) 124.1 (15)
N2-H22...O2 0.85 (2) 2.03 (2) 2.6387 (19) 127.3 (19)
O3-H31...N3iv 0.85 (2) 1.89 (2) 2.7354 (18) 176 (2)
O3-H32...O4v 0.89 (3) 1.90 (3) 2.776 (2) 168 (3)
O4-H41...O3 0.90 (2) 1.88 (3) 2.7727 (19) 170 (4)
O4-H42...O1vi 0.85 (2) 2.53 (2) 3.0930 (17) 125 (2)
O4-H42...O2vi 0.85 (2) 2.17 (2) 3.0126 (17) 171 (3)
C5-H5...O1ii 0.93 2.54 3.3556 (19) 146
Symmetry codes: (i) -x, -y+2, -z+2; (ii) x, y+1, z; (iii) -x+1, -y+2, -z+1; (iv) -x, -y+1, -z+2; (v) -x, -y+1, -z+1; (vi) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2305 ).

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for use of the X-ray diffractometer.

References

Alamgir, M., Black, D. S. C. & Kumar, N. (2007). Top. Heterocycl. Chem. 9, 87-118.  [CrossRef] [ChemPort]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dinçer, S., Gönülalan, G., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, o806-o807.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hoffmann, H. S., Stefani, V., Benvenutti, E. V., Costa, T. M. H. & Gallas, M. R. (2011). Mater. Chem. Phys. 126, 97-101.  [CrossRef] [ChemPort]
Hökelek, T., Dinçer, S. & Kiliç, E. (2002). Cryst. Res. Technol. 37, 1138-1142.  [CrossRef] [ChemPort]
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kuznetsov, Y. I. & Kazansky, L. P. (2008). Russ. Chem. Rev. 77, 219-232.  [CrossRef] [ChemPort]
Laryea, D., Gullbo, J., Isakssoon, A., Larsson, R. & Nygren, P. (2010). Anti-Cancer Drugs, 21, 33-42.  [CrossRef] [PubMed] [ChemPort]
Refaat, H. M. (2010). Eur. J. Med. Chem. 45, 2949-2956.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soula, C. & Luu-Duc, C. (1986). Lyon Pharm. 37, 297-302.  [ChemPort]
Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.  [CrossRef] [ChemPort]
Subramanyam, N. C. & Mayanna, S. M. (1985). Corros. Sci. 25, 163-169.  [ChemPort]

Acta Cryst (2011). E67, o2490-o2491   [ doi:10.1107/S1600536811034647 ]

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