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Volume 70 
Part 1 
Page o19  
January 2014  

Received 25 November 2013
Accepted 1 December 2013
Online 7 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.181
Data-to-parameter ratio = 10.1
Details
Open access

5-(3,5-Di­fluoro­phen­yl)-1-(4-fluoro­phen­yl)-3-tri­fluoro­methyl-1H-pyrazole

aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C16H8F6N2, the dihedral angle between the pyrazole and di­fluoro­benzene rings is 50.30 (13)°, while those between the pyrazole and fluoro­benzene rings and between the di­fluoro­benzene and fluoro­benzene rings are 38.56 (13) and 53.50 (11)°, respectively. Aromatic [pi]-[pi] stacking inter­actions between adjacent di­fluoro­benzene rings [centroid-centroid separation = 3.6082 (11) Å] link the mol­ecules into dimers parallel to [21-2].

Related literature

For background to pyrazole derivatives and their uses, see: Ramaiah et al. (1999[Ramaiah, K., Grossert, J. S., Hooper, D. L., Dubey, P. K. & Ramanatham, J. (1999). J. Indian Chem. Soc. 76, 140-144.]). For a similar structure, see: Sreenivasa et al. (2013[Sreenivasa, S., Manojkumar, K. E., Suchetan, P. A., Mohan, N. R., Kumar, V. & Palakshamurthy, B. S. (2013). Acta Cryst. E69, o176.]).

[Scheme 1]

Experimental

Crystal data
  • C16H8F6N2

  • Mr = 342.24

  • Triclinic, [P \overline 1]

  • a = 7.2535 (3) Å

  • b = 8.6686 (4) Å

  • c = 11.7690 (5) Å

  • [alpha] = 70.909 (1)°

  • [beta] = 80.139 (1)°

  • [gamma] = 88.077 (1)°

  • V = 688.78 (5) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.39 mm-1

  • T = 293 K

  • 0.39 × 0.35 × 0.29 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.611, Tmax = 0.669

  • 7069 measured reflections

  • 2181 independent reflections

  • 2040 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.181

  • S = 1.11

  • 2181 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, 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: 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2788 ).


Acknowledgements

The authors acknowledge the IOE X-ray diffractometer Facility, University of Mysore, Mysore, for the data collection.

References

Bruker (2009). APEX2, SAINT-Plus 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]
Ramaiah, K., Grossert, J. S., Hooper, D. L., Dubey, P. K. & Ramanatham, J. (1999). J. Indian Chem. Soc. 76, 140-144.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreenivasa, S., Manojkumar, K. E., Suchetan, P. A., Mohan, N. R., Kumar, V. & Palakshamurthy, B. S. (2013). Acta Cryst. E69, o176.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2014). E70, o19  [ doi:10.1107/S1600536813032650 ]

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