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Volume 69 
Part 9 
Page o1434  
September 2013  

Received 18 July 2013
Accepted 30 July 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.162
Data-to-parameter ratio = 11.9
Details
Open access

[4-(4-Methoxyphenyl)-2-(pyridin-3-yl)-1,3-thiazol-5-yl][4-(trifluoromethyl)phenyl]methanone

aDepartment of Studies in Microbiology, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Physics, Faculty of Science, An Najah National University, Nabtus, West Bank, Palestinian Territories,cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and dDepartment 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, C23H15F3N2O2S, the thiazole ring makes dihedral angles of 12.98 (13), 49.30 (11) and 49.83 (12)° with the pyridine ring, the methoxyphenyl ring and the (trifluoromethyl)phenyl ring, respectively. In the crystal, molecules are connected via C-H...O hydrogen bonds, forming chains along [010]. There are also C-H...[pi] and C-F...[pi] interactions present, forming a three-dimensional structure.

Related literature

For biological and other properties of thiazoles, see: Mustafa et al. (2004[Mustafa, S. M., Nair, V. A., Chittoor, J. P. & Krishnapillai, S. (2004). Mini-Rev. Org. Chem. 1, 375-385.]); Sperry & Wright (2005[Sperry, J. B. & Wright, D. L. (2005). Curr. Opin. Drug Discov. Dev. 8, 723-731.]); Zagade & Senthilkumar (2011[Zagade, A. A. & Senthilkumar, G. P. (2011). Der. Pharma Chem. 3, 523-529.]); Narender et al. (2005[Narender, M., Somi Reddy, M., Sridhar, R., Nageswar, Y. V. D. & Rama Rao, K. (2005). Tetrahedron Lett. 46, 5953-5955.]). For the crystal structure of a related compound, see: Lu et al. (2006[Lu, Y.-C., Dai, H., Zheng, T., Zhang, B.-N. & Fang, J.-X. (2006). Acta Cryst. E62, o5330-o5331.]).

[Scheme 1]

Experimental

Crystal data
  • C23H15F3N2O2S

  • Mr = 440.44

  • Orthorhombic, P b c a

  • a = 19.4157 (5) Å

  • b = 7.6564 (2) Å

  • c = 27.4040 (7) Å

  • V = 4073.73 (18) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 1.87 mm-1

  • T = 273 K

  • 0.18 × 0.18 × 0.10 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.753, Tmax = 0.753

  • 35383 measured reflections

  • 3352 independent reflections

  • 3140 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.162

  • S = 1.05

  • 3352 reflections

  • 281 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.79 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N4/C1-C3/C5/C6 and C12-C17 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C13-H13...O19i 0.93 2.52 3.275 (3) 138
C5-H5...Cg1ii 0.93 2.93 3.597 (3) 129
C17-H17...Cg2iii 0.93 2.89 3.568 (2) 131
C26-F29...Cg1iv 1.30 (1) 3.47 (1) 4.626 (4) 149 (1)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). 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: SU2625 ).


Acknowledgements

We are grateful to IOE, University of Mysore, for providing the single crystal X-ray diffraction facility.

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Lu, Y.-C., Dai, H., Zheng, T., Zhang, B.-N. & Fang, J.-X. (2006). Acta Cryst. E62, o5330-o5331.  [CSD] [CrossRef] [ChemPort] [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]
Mustafa, S. M., Nair, V. A., Chittoor, J. P. & Krishnapillai, S. (2004). Mini-Rev. Org. Chem. 1, 375-385.  [CrossRef] [ChemPort]
Narender, M., Somi Reddy, M., Sridhar, R., Nageswar, Y. V. D. & Rama Rao, K. (2005). Tetrahedron Lett. 46, 5953-5955.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sperry, J. B. & Wright, D. L. (2005). Curr. Opin. Drug Discov. Dev. 8, 723-731.  [ChemPort]
Zagade, A. A. & Senthilkumar, G. P. (2011). Der. Pharma Chem. 3, 523-529.  [ChemPort]


Acta Cryst (2013). E69, o1434  [ doi:10.1107/S1600536813021259 ]

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