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Volume 69 
Part 5 
Page o807  
May 2013  

Received 15 April 2013
Accepted 24 April 2013
Online 30 April 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.056
wR = 0.148
Data-to-parameter ratio = 12.7
Details
Open access

6-Chloro-2-(thiophen-2-yl)-1-[(thiophen-2-yl)methyl]-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

The title compound, C16H11ClN2S2, co-crystallizes with a small amount of the 5-chloro- isomer. The ratio of 6-chloro- to 5-chloro- isomers is 0.969 (2):0.031 (2). One thiophen-2-yl substitutent displays rotational disorder with 80.6 (4)% of the molecules exhibiting the major orientation. In the crystal, weak C-H...N and C-H...S hydrogen-bonding interactions result in chains of molecules parallel to [001].

Related literature

For the structure 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 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 /c

  • a = 15.465 (3) Å

  • b = 6.3578 (10) Å

  • c = 15.634 (3) Å

  • [beta] = 103.687 (5)°

  • V = 1493.5 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.53 mm-1

  • T = 200 K

  • 0.80 × 0.60 × 0.20 mm

Data collection
  • Bruker SMART X2S CCD 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

  • 23773 measured reflections

  • 2665 independent reflections

  • 2184 reflections with I > 2[sigma](I)

  • Rint = 0.088

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.148

  • S = 1.11

  • 2665 reflections

  • 210 parameters

  • 38 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...N2i 0.95 2.62 3.369 (4) 136
C12-H12B...N2ii 0.99 2.69 3.654 (4) 165
C12-H12B...S1ii 0.99 2.99 3.599 (4) 120
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) x, y+1, 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). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: PV2630 ).


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.  [CrossRef] [details]
Geiger, D. K., Geiger, H. C., Williams, L. & Noll, B. C. (2012). Acta Cryst. E68, o420.  [CSD] [CrossRef] [details]
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. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o807  [ doi:10.1107/S1600536813011124 ]

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