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Volume 67 
Part 3 
Page o719  
March 2011  

Received 20 February 2011
Accepted 21 February 2011
Online 26 February 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.136
Data-to-parameter ratio = 16.1
Details
Open access

N-(4,6-Dimethylpyrimidin-2-yl)-1H-benzimidazol-2-amine

aChemistry & Environmental Science Division, School of Science, Manchester Metropolitan University, England,bDepartment of Chemistry, Sohag University, Sohag, Egypt,cDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

There are two independent molecules in the asymmetric unit of the title compound, C13H13N5. In each molecule, an amino N atom is connected to a benzimidazole fused-ring system and a pyrimidine ring [these are aligned at 1.3 (1)° in one independent molecule and at 5.4 (1)° in the other]. The amino N atom of the fused ring forms an intramolecular N-H...O hydrogen bond to a pyrimidine N atom in each molecule. The amino N atom connecting the two ring systems interacts with the other N atom of the pyrimidine ring of an adjacent molecule, generating centrosymmetric hydrogen-bonded dimers.

Related literature

For the synthesis, see: Bossio et al. (1985[Bossio, R., Marcaccini, S., Parrini, V. & Pepino, R. (1985). J. Heterocycl. Chem. 22, 1147-1148.]); Shestakov et al. (2006[Shestakov, A. S., Gusakova, N. V., Shikhaliev, Kh. S. & Zagoruiko, A. V. (2006). Russ. J. Gen. Chem. 76, 1719-1724.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13N5

  • Mr = 239.28

  • Triclinic, [P \overline 1]

  • a = 8.2836 (4) Å

  • b = 9.6135 (5) Å

  • c = 16.5694 (8) Å

  • [alpha] = 92.121 (1)°

  • [beta] = 96.100 (1)°

  • [gamma] = 112.597 (1)°

  • V = 1206.94 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII diffractometer

  • 13373 measured reflections

  • 5550 independent reflections

  • 4124 reflections with I > 2[sigma](I)

  • Rint = 0.019

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

  • wR(F2) = 0.136

  • S = 1.01

  • 5550 reflections

  • 345 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N5 0.86 (1) 2.05 (2) 2.664 (2) 128 (2)
N3-H3...N2i 0.87 (1) 2.05 (1) 2.912 (2) 170 (2)
N7-H7...N10 0.87 (1) 2.10 (2) 2.695 (2) 125 (2)
N8-H8...N6ii 0.87 (1) 2.05 (1) 2.908 (2) 170 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5003 ).


Acknowledgements

We thank Manchester Metropolitan University, Baku State University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bossio, R., Marcaccini, S., Parrini, V. & Pepino, R. (1985). J. Heterocycl. Chem. 22, 1147-1148.  [CrossRef] [ChemPort]
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shestakov, A. S., Gusakova, N. V., Shikhaliev, Kh. S. & Zagoruiko, A. V. (2006). Russ. J. Gen. Chem. 76, 1719-1724.  [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2011). E67, o719  [ doi:10.1107/S1600536811006507 ]

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