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Volume 69 
Part 11 
Page o1689  
November 2013  

Received 1 October 2013
Accepted 17 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.059
wR = 0.156
Data-to-parameter ratio = 14.3
Details
Open access

2-(3,4-Di­fluoro­phen­yl)-1H-benzimidazole

aDepartment of Chemistry, Bangalore University, Bangalore 560 001, India
Correspondence e-mail: noorsb@rediffmail.com

In the title mol­ecule, C13H8F2N2, the dihedral angle between the benzimidazole ring system and the di­fluoro-substituted benzene ring is 30.0 (1)°. In the crystal, mol­ecules are linked by N-H...N hydrogen bonds, forming chains along [010]. In addition, weak C-H...F hydrogen bonds connect chains into a two-dimensional network parallel to (001). A weak C-H...[pi] inter­action is observed between an H atom of the benzimidazole ring sytem and the [pi] system of the di­fluoro-substituted benzene ring.

Related literature

For the therapeutic and medicinal properties of benzimidazole derivatives, see: Chimirri et al. (1991[Chimirri, A., Grasso, S., Monforte, A. M., Monforte, P. & Zappala, M. (1991). Il Farmaco, 46, 925-933.]); Ishihara et al. (1994[Ishihara, K., Ichikawa, T., Komuro, Y., Ohara, S. & Hotta, K. (1994). Arzneim. Forsch. Drug. Res. 44, 827-830.]); Kubo et al. (1993[Kubo, K., Kohara, Y., Imamia, E., Sugiura, Y., Inada, Y., Furukawa, Y., Nishikawa, K. & Naka, T. (1993). J. Med. Chem. 36, 2182-2195.]). For related structures, see: Rashid et al. (2007[Rashid, N., Tahir, M. K., Kanwal, S., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1402-o1403.]); Jayamoorthy et al. (2012[Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.]); Yoon et al. (2012[Yoon, Y. K., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2715-o2716.]); Fathima et al. (2013[Fathima, N., Krishnamurthy, M. S. & Begum, N. S. (2013). Acta Cryst. E69, o264.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8F2N2

  • Mr = 230.21

  • Orthorhombic, P b c a

  • a = 8.7195 (17) Å

  • b = 9.9454 (19) Å

  • c = 23.389 (4) Å

  • V = 2028.2 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.18 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]) Tmin = 0.982, Tmax = 0.984

  • 13072 measured reflections

  • 2209 independent reflections

  • 1558 reflections with I > 2[sigma](I)

  • Rint = 0.067

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.156

  • S = 1.01

  • 2209 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the ring C9-C13 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.88 2.04 2.874 (3) 158
C13-H13...F2ii 0.95 2.51 3.379 (3) 153
C3-H3A...Cgiii 0.95 2.89 3.529 (3) 125
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5659 ).


Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.
Chimirri, A., Grasso, S., Monforte, A. M., Monforte, P. & Zappala, M. (1991). Il Farmaco, 46, 925-933.  [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fathima, N., Krishnamurthy, M. S. & Begum, N. S. (2013). Acta Cryst. E69, o264.  [CSD] [CrossRef] [IUCr Journals]
Ishihara, K., Ichikawa, T., Komuro, Y., Ohara, S. & Hotta, K. (1994). Arzneim. Forsch. Drug. Res. 44, 827-830.  [ChemPort]
Jayamoorthy, K., Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J. & Butcher, R. J. (2012). Acta Cryst. E68, o2708.  [CSD] [CrossRef] [IUCr Journals]
Kubo, K., Kohara, Y., Imamia, E., Sugiura, Y., Inada, Y., Furukawa, Y., Nishikawa, K. & Naka, T. (1993). J. Med. Chem. 36, 2182-2195.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Rashid, N., Tahir, M. K., Kanwal, S., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1402-o1403.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.
Yoon, Y. K., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2715-o2716.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1689  [ doi:10.1107/S1600536813028559 ]

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