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

Mohamed, S.K.; El-Remaily, M.A.A.; Gurbanov, A.V.; Khalilov, A.N.; Ng, S.W.

doi:10.1107/S1600536811006507

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 (C-C) = 0.003 Å
R = 0.044
wR = 0.136
Data-to-parameter ratio = 16.1
Details

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

Shaaban Kamel Mohamed,^a Mahmoud A. A. El-Remaily,^b Atash V. Gurbanov,^c Ali N. Khalilov ^c and Seik Weng Ng ^d ^*

^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-HO 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); Shestakov et al. (2006).

Experimental

Crystal data

C₁₃H₁₃N₅
M_r = 239.28
Triclinic, $[P \overline 1]$
a = 8.2836 (4) Å
b = 9.6135 (5) Å
c = 16.5694 (8) Å
= 92.121 (1)°
= 96.100 (1)°
= 112.597 (1)°
V = 1206.94 (10) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.019

Refinement

R[F² > 2(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
_max = 0.25 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N5	0.86 (1)	2.05 (2)	2.664 (2)	128 (2)
N3-H3N2ⁱ	0.87 (1)	2.05 (1)	2.912 (2)	170 (2)
N7-H7N10	0.87 (1)	2.10 (2)	2.695 (2)	125 (2)
N8-H8N6ⁱⁱ	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

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

organic compounds