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Volume 69 
Part 10 
Pages o1539-o1540  
October 2013  

Received 28 August 2013
Accepted 8 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.038
wR = 0.093
Data-to-parameter ratio = 12.8
Details
Open access

5-Chloro-2-(thiophen-2-yl)-1-(thiophen-2-ylmethyl)-1H-benzimidazole-6-chloro-2-(thiophen-2-yl)-1-(thiophen-2-ylmethyl)-1H-benzimidazole (0.94/0.06)

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, C16H11ClN2S2. The structure exhibits rotational disorder of the 2-thiophen-2-yl substituent in each of the unique molecules with a major:minor component ratio of 0.927 (2):0.073 (2). For one of the symmetry-unique molecules, 6.0 (2)% of the sites are occupied by the 6-chloro-isomer. The major component thiophene rings make dihedral angles of 38.90 (12) and 36.32 (11)° with the benzimidazole rings in the two independent molecules. In the crystal, molecules are linked into chains parallel to [100] via weak C-H...N interactions.

Related literature

For the structure of 6-chloro-2-(thiophen-2-yl)-1-(thiophen-2-ylmethyl)-1H-benzimidazole, see: Geiger & Nellist (2013[Geiger, D. K. & Nellist, M. R. (2013). Acta Cryst. E69, o807.]). For the structure of the 5-bromo analogue, see: Geiger & Destefano (2012[Geiger, D. K. & Destefano, M. R. (2012). Acta Cryst. E68, o3123.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11ClN2S2

  • Mr = 330.84

  • Monoclinic, P 21 /n

  • a = 12.7407 (11) Å

  • b = 10.5126 (8) Å

  • c = 22.955 (2) Å

  • [beta] = 100.461 (3)°

  • V = 3023.4 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 200 K

  • 0.80 × 0.40 × 0.20 mm

Data collection
  • Bruker SMART X2S benchtop diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.62, Tmax = 0.90

  • 32145 measured reflections

  • 5356 independent reflections

  • 4419 reflections with I > 2[sigma](I)

  • Rint = 0.072

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

  • wR(F2) = 0.093

  • S = 1.08

  • 5356 reflections

  • 420 parameters

  • 227 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C22-H22...N2 0.95 2.68 3.581 (3) 159
C28-H28B...N2 0.99 2.58 3.460 (3) 148
C3i-H3i...N4 0.95 2.68 3.584 (3) 159
C12i-H12Ai...N4 0.99 2.62 3.514 (3) 150
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). University of Göttingen, Germany.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: FJ2642 ).


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. MRN thanks Dr Bruce Ristow for a summer research fellowship administered by the Geneseo Foundation.

References

Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Geiger, D. K. & Destefano, M. R. (2012). Acta Cryst. E68, o3123.  [CSD] [CrossRef] [IUCr Journals]
Geiger, D. K. & Nellist, M. R. (2013). Acta Cryst. E69, o807.  [CSD] [CrossRef] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1539-o1540   [ doi:10.1107/S1600536813024999 ]

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