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Volume 67 
Part 6 
Pages o1523-o1524  
June 2011  

Received 10 May 2011
Accepted 19 May 2011
Online 25 May 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 12.7
Details
Open access

2-Methyl-5-nitro-1H-benzimidazole monohydrate

Raza Murad Ghalib,a Rokiah Hashim,a Othman Sulaiman,a Ching Kheng Quahb+ and Hoong-Kun Funb*++

aSchool of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C8H7N3O2·H2O, the 2-methyl-5-nitro-1H-benzimidazole molecule, excluding the methyl H atoms, is approximately planar, with a maximum deviation of 0.137 (1) Å. The crystal structure is stabilized by water molecules via N-H...O(water), O(water)-H...O and O(water)-H...N hydrogen bonds, forming sheets parallel to the (100) plane. A short intermolecular contact between the benzene and imidazole rings, with a centroid-centroid distance of 3.6419 (10) Å, indicates a [pi]-[pi] interaction.

Related literature

For general background to and the potential biological activity of benzimidazole derivatives, see: Puratchikody et al. (2008[Puratchikody, A., Nagalakshmi, G. & Doble, M. (2008). Chem. Pharm. Bull. 56, 273-281.]); 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. & La Colla, P. (2010). Bioorg. Med. Chem. 18, 2937-2953.]); Shingalapur et al. (2010[Shingalapur, R. V., Hosamani, K. M., Keri, R. S. & Hugar, M. H. (2010). Eur. J. Med. Chem. 45, 1753-1759.]); Refaat (2010[Refaat, H. M. (2010). Eur. J. Med. Chem. 45, 2949-2956.]); Lazer et al. (1987[Lazer, E. S., Matteo, M. R. & Possanza, G. J. (1987). J. Med. Chem. 30, 726-729.]). For the preparation of the title compound, see: Umare et al. (2008[Umare, V. D., Ingle, V. N. & Wanare, R. K. (2008). Indian J. Heterocycl. Chem. 17, 253-256.]); Singh & Pathak (2008[Singh, J. & Pathak, D. P. (2008). Orient. J. Chem. 24, 175-180.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For standard bond-length data, 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.]). For related structures, see: Eltayeb et al. (2009[Eltayeb, N. E., Teoh, S. G., Quah, C. K., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o1613-o1614.]); Arumugam et al. (2010[Arumugam, N., Abdul Rahim, A. S., Osman, H., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o2412-o2413.]).

[Scheme 1]

Experimental

Crystal data

  • C8H7N3O2·H2O

  • Mr = 195.18

  • Triclinic, [P \overline 1]

  • a = 6.9051 (10) Å

  • b = 7.1309 (11) Å

  • c = 10.0653 (15) Å

  • [alpha] = 79.421 (3)°

  • [beta] = 73.062 (3)°

  • [gamma] = 67.517 (3)°

  • V = 436.61 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.52 × 0.19 × 0.14 mm
Data collection

  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.942, Tmax = 0.984

  • 6312 measured reflections

  • 1784 independent reflections

  • 1506 reflections with I > 2[sigma](I)

  • Rint = 0.032
Refinement

  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.06

  • 1784 reflections

  • 140 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1Wi 0.91 (3) 1.84 (2) 2.7347 (18) 170 (2)
O1W-H1W1...O2ii 0.831 (19) 2.06 (2) 2.8737 (17) 168.5 (19)
O1W-H2W1...N2iii 0.92 (3) 1.86 (3) 2.7808 (18) 177.2 (17)
Symmetry codes: (i) x, y, z-1; (ii) x, y+1, z; (iii) x, y+1, z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: IS2711 ).

Acknowledgements

We would like to acknowledge Universiti Sains Malaysia (USM) for the University Grant 1001/PTEKIND/8140152. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

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.
Arumugam, N., Abdul Rahim, A. S., Osman, H., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o2412-o2413.  [CSD] [CrossRef] [details]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Eltayeb, N. E., Teoh, S. G., Quah, C. K., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o1613-o1614.  [CSD] [CrossRef] [details]
Lazer, E. S., Matteo, M. R. & Possanza, G. J. (1987). J. Med. Chem. 30, 726-729.  [ChemPort] [PubMed] [ISI]
Puratchikody, A., Nagalakshmi, G. & Doble, M. (2008). Chem. Pharm. Bull. 56, 273-281.  [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]
Shingalapur, R. V., Hosamani, K. M., Keri, R. S. & Hugar, M. H. (2010). Eur. J. Med. Chem. 45, 1753-1759.  [ISI] [ChemPort] [PubMed]
Singh, J. & Pathak, D. P. (2008). Orient. J. Chem. 24, 175-180.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [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. & La Colla, P. (2010). Bioorg. Med. Chem. 18, 2937-2953.  [CrossRef] [ChemPort] [PubMed]
Umare, V. D., Ingle, V. N. & Wanare, R. K. (2008). Indian J. Heterocycl. Chem. 17, 253-256.  [ChemPort]

Acta Cryst (2011). E67, o1523-o1524   [ doi:10.1107/S1600536811019027 ]

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