[2-(1H-Benzimidazol-2-yl-κN3)aniline-κN]dichloridozinc

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536811026572

Volume 67
Part 8
Pages m1062-m1063
August 2011

Received 1 July 2011
Accepted 4 July 2011
Online 9 July 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.081
Data-to-parameter ratio = 42.7
Details

[2-(1H-Benzimidazol-2-yl-N³)aniline-N]dichloridozinc

Naser Eltaher Eltayeb,^a,^b Siang Guan Teoh,^a Suchada Chantrapromma ^c ⁺ and Hoong-Kun Fun ^d ^*⁺⁺

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Chemistry, Faculty of Pure and Applied Sciences, International University of Africa, Sudan,^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title benzimidazole mononuclear complex, [ZnCl₂(C₁₃H₁₁N₃)], the Zn^II ion is four-coordinated in a distorted tetrahedral geometry by an imidazole N, an amino N and two Cl atoms. The dihedral angle between the benzimidazole and benzene rings is 9.57 (1)°. In the crystal, molecules are linked by weak N-HCl hydrogen bonds into layers parallel to the bc plane. [pi] - [pi] interactions with centroid-centroid distances in the range 3.4452 (8)-3.8074 (8) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987). For background to benzimidazoles and their applications, see: Chassaing et al. (2008); Podunavac-Kuzmonovic et al. (1999); Xue et al. (2011). For related structures, see: Eltayeb et al. (2007; 2009; 2011); Maldonado-Rogado et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

[ZnCl₂(C₁₃H₁₁N₃)]
M_r = 345.54
Monoclinic, C 2/c
a = 22.0252 (7) Å
b = 10.0651 (3) Å
c = 15.3676 (6) Å
= 125.244 (2)°
V = 2782.32 (18) Å³
Z = 8
Mo K radiation
= 2.14 mm^-1
T = 100 K
0.48 × 0.31 × 0.31 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.428, T_max = 0.560
50659 measured reflections
7344 independent reflections
5887 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.081
S = 1.02
7344 reflections
172 parameters
H-atom parameters constrained
_max = 0.54 e Å^-3
_min = -0.55 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1N2Cl1ⁱ	0.82	2.56	3.3503 (9)	164
N3-H1N3Cl1ⁱⁱ	0.89	2.49	3.3753 (9)	174
N3-H2N3Cl2ⁱⁱⁱ	0.94	2.44	3.3015 (12)	153
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y+2, -z; (iii) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2622 ).

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing study leave. The authors also thank Universiti Sains Malaysia 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.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chassaing, C., Berger, M., Heckeroth, A., Ilg, T., Jaeger, M., Kern, C., Schmid, K. & Uphoff, M. (2008). J. Med. Chem. 51, 1111-1114.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S. & Fun, H.-K. (2007). Acta Cryst. E63, o4141-o4142.
Eltayeb, N. E., Teoh, S. G., Quah, C. K., Fun, H.-K. & Adnan, R. (2009). Acta Cryst. E65, o1613-o1614.
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Xue, F., Luo, X., Ye, C., Ye, W. & Wang, Y. (2011). Bioorg. Med. Chem. 19, 2641-2649.