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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 [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.038
wR = 0.091
Data-to-parameter ratio = 14.2
Details
Open access

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

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-H...N hydrogen bonds and C-H...thiophene 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[Geiger, D. K., Geiger, H. C., Williams, L. & Noll, B. C. (2012). Acta Cryst. E68, o420.]). For examples of pharmacological uses of benzimidazoles, see: López-Rodríguez et al. (1999[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.]); Varala et al. (2007[Varala, R., Nasreen, A., Enugala, R. & Adapa, S. R. (2007). Tetrahedron Lett. 48, 69-72.]); Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]). For the synthesis of substituted benzimidazoles, see: Grimmett (1997[Grimmett, M. R. (1997). Imidazole and Benzidmidazole Synthesis. San Diego: Academic Press.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11BrN2S2

  • Mr = 375.30

  • Monoclinic, P 21 /n

  • a = 12.6753 (17) Å

  • b = 10.5413 (11) Å

  • c = 23.581 (3) Å

  • [beta] = 100.878 (4)°

  • V = 3094.1 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.46, Tmax = 0.76

  • 19813 measured reflections

  • 5581 independent reflections

  • 4191 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.091

  • S = 1.02

  • 5581 reflections

  • 392 parameters

  • 91 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C12i-H12Bi...N4 0.99 2.57 3.454 (4) 149
C22-H22...N2 0.95 2.61 3.504 (4) 158
C28-H28A...N2 0.99 2.61 3.522 (4) 152
C6i-H6i...N4 0.95 2.65 3.547 (4) 157
C3-H3...Cg4 0.95 2.68 3.578 (4) 158
C19-H19...Cg2i 0.95 2.62 3.512 (4) 157
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: XSHELL (Bruker, 2004[Bruker (2004). XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]) and Mercury (Macrae et al., 2008[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.]); 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: 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.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [PubMed]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Varala, R., Nasreen, A., Enugala, R. & Adapa, S. R. (2007). Tetrahedron Lett. 48, 69-72.  [ISI] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3123  [ doi:10.1107/S1600536812042146 ]

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