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Volume 69 
Part 12 
Page o1846  
December 2013  

Received 5 November 2013
Accepted 22 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.144
Data-to-parameter ratio = 12.2
Details
Open access

1-(4-Methyl­phenyl­sulfon­yl)-2-{[3-methyl-4-(2,2,2-tri­fluoro­eth­oxy)pyridin-2-yl]methyl­sulfan­yl}-1H-1,3-benzimidazole

aDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C23H20F3N3O3S2, the benzo­imidazole unit makes dihedral angles of 5.02 (1) and 76.42 (1)°, respectively, with the pyridine and methyl­benzene rings; the dihedral angle between the pyridine and methyl­benzene rings is 72.19 (1)°. In the crystal, mol­ecules are connected by weak C-H...F, C-H...O and C-H...N hydrogen bonds. Weak C-H...[pi] inter­actions and [pi]-[pi] stacking [centroid-centroid distance = 3.6485 (14) Å] are also observed. The overall packing shows a three-dimensional architecture. The crystal structure contains a void of 51 Å3, but no solvent mol­ecule (hexane or ethyl acetate) is located within it.

Related literature

For the biological activity of benzo­imidazole derivatives, see: Bansal & Silakari (2012[Bansal, Y. & Silakari, O. (2012). Bioorg. Med. Chem. 20, 6208-6236.]); Ates-Alagoz et al. (2004[Ates-Alagoz, Z., Can-Eke, B., Coban, T., Iscan, M. & Buyukbingol, E. (2004). Arch. Pharm. 337 188-192.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C23H20F3N3O3S2

  • Mr = 507.56

  • Triclinic, [P \overline 1]

  • a = 9.1129 (6) Å

  • b = 9.5116 (6) Å

  • c = 13.7914 (8) Å

  • [alpha] = 90.978 (3)°

  • [beta] = 101.749 (2)°

  • [gamma] = 93.449 (3)°

  • V = 1167.72 (13) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.56 mm-1

  • T = 296 K

  • 0.21 × 0.20 × 0.20 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.615, Tmax = 0.628

  • 13085 measured reflections

  • 3779 independent reflections

  • 3301 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.144

  • S = 1.08

  • 3779 reflections

  • 310 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the imidazole ring.

D-H...A D-H H...A D...A D-H...A
C2-H2...F2i 0.93 2.49 3.363 (4) 156
C15-H15B...O3ii 0.97 2.52 3.420 (3) 155
C18-H18...N3iii 0.93 2.60 3.336 (3) 136
C18-H18...Cg1 0.93 2.83 3.463 (3) 126
Symmetry codes: (i) x-1, y-1, z-1; (ii) -x+1, -y+2, -z+1; (iii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). 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: 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: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5751 ).


Acknowledgements

The authors are thankful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility.

References

Ates-Alagoz, Z., Can-Eke, B., Coban, T., Iscan, M. & Buyukbingol, E. (2004). Arch. Pharm. 337 188-192.  [ChemPort]
Bansal, Y. & Silakari, O. (2012). Bioorg. Med. Chem. 20, 6208-6236.  [CrossRef] [ChemPort] [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1846  [ doi:10.1107/S1600536813031899 ]

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