5-Bromo-2-(thio­phen-2-yl)-1-(thio­phen-2-ylmeth­yl)-1H-benzimidazole

Geiger, D.K.; Destefano, M.R.

doi:10.1107/S1600536812042146

Volume 68
Part 11
Page o3123
November 2012

Received 27 September 2012
Accepted 8 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.038
wR = 0.091
Data-to-parameter ratio = 14.2
Details

5-Bromo-2-(thiophen-2-yl)-1-(thiophen-2-ylmethyl)-1H-benzimidazole

David K. Geiger ^a ^* and Matthew R. Destefano ^a

^aDepartment of Chemistry, State University of New York-College at Geneseo, 1 College Circle, Geneseo, NY 14454, USA
Correspondence e-mail: geiger@geneseo.edu

There are two independent molecules in the asymmetric unit of the title compound, C₁₆H₁₁BrN₂S₂. In the crystal, weak C-HN hydrogen bonds and C-Hthiophene ring interactions link the molecules into chains along [100]. The structure exhibits disorder of the 2-thiophen-2-yl substituent of one of the symmetry-unique molecules with a major:minor component ratio of 0.914 (3):0.086 (3).

Related literature

For the characterization of 2-(thiophen-2-yl)-1-(thiophen-2-ylmethyl)-1H-benzimidazole, see: Geiger et al. (2012). For examples of pharmacological uses of benzimidazoles, see: López-Rodríguez et al. (1999); Varala et al. (2007); Horton et al. (2003). For the synthesis of substituted benzimidazoles, see: Grimmett (1997).

Experimental

Crystal data

C₁₆H₁₁BrN₂S₂
M_r = 375.30
Monoclinic, P 2₁ /n
a = 12.6753 (17) Å
b = 10.5413 (11) Å
c = 23.581 (3) Å
= 100.878 (4)°
V = 3094.1 (6) Å³
Z = 8
Mo K radiation
= 2.92 mm^-1
T = 200 K
0.60 × 0.20 × 0.10 mm

Data collection

Bruker SMART X2S benchtop diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) T_min = 0.46, T_max = 0.76
19813 measured reflections
5581 independent reflections
4191 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.091
S = 1.02
5581 reflections
392 parameters
91 restraints
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.80 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the S2,C13-C16 and S4,C29-C32 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C12ⁱ-H12BⁱN4	0.99	2.57	3.454 (4)	149
C22-H22N2	0.95	2.61	3.504 (4)	158
C28-H28AN2	0.99	2.61	3.522 (4)	152
C6ⁱ-H6ⁱN4	0.95	2.65	3.547 (4)	157
C3-H3Cg4	0.95	2.68	3.578 (4)	158
C19-H19Cg2ⁱ	0.95	2.62	3.512 (4)	157
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: XSHELL (Bruker, 2004) and Mercury (Macrae et al., 2008); 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: LR2085 ).

Acknowledgements

This work was supported by a Congressionally directed grant from the US Department of Education (grant No. P116Z100020) for the X-ray diffractometer and a grant from the Geneseo Foundation.

References

Bruker (2004). XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Geiger, D. K., Geiger, H. C., Williams, L. & Noll, B. C. (2012). Acta Cryst. E68, o420.
Grimmett, M. R. (1997). Imidazole and Benzidmidazole Synthesis. San Diego: Academic Press.
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.
López-Rodríguez, M. L., Benhamú, B., Morcillo, M. J., Tejeda, I. D., Orensanz, L., Alfaro, M. J. & Martín, M. I. (1999). J. Med. Chem. 42, 5020-5028.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.
Varala, R., Nasreen, A., Enugala, R. & Adapa, S. R. (2007). Tetrahedron Lett. 48, 69-72.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds