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Volume 69 
Part 4 
Page o618  
April 2013  

Received 25 March 2013
Accepted 25 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.006 Å
R = 0.065
wR = 0.232
Data-to-parameter ratio = 17.9
Details
Open access

4-[5-(4-Fluorophenyl)-1-(4-phenyl-1,3-thiazol-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]-5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole

aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C28H23FN6S, the pyrazole ring adopts an envelope conformation, with the methine C atom being the flap atom. With respect to this ring, the 2-thienyl, triazole and fluorobenzene rings are approximately coplanar, coplanar and perpendicular, respectively [dihedral angles = 8.56 (17), 6.03 (19) and 73.1 (2)°, respectively] so that to a first approximation the molecule has a T-shape. In the crystal, molecules are consolidated into a three-dimensional architecture by C-H...F (involving a bifurcated F atom), C-H...S and C-H...[pi] interactions.

Related literature

For the synthesis, structure and biological activity of 1-thiazol-2-ylpyrazoline, see: Abdel-Wahab et al. (2012[Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.]); Dong et al. (2011[Dong, W.-J., Cui, F.-H., Gao, Z.-L., Li, R.-S., Shen, G.-L. & Dong, H.-S. (2011). J. Heterocycl. Chem. 48, 1154-1160.]).

[Scheme 1]

Experimental

Crystal data
  • C28H23FN6S

  • Mr = 494.58

  • Monoclinic, P 21 /n

  • a = 17.7373 (18) Å

  • b = 7.8367 (7) Å

  • c = 19.4159 (18) Å

  • [beta] = 109.323 (11)°

  • V = 2546.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 295 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.901, Tmax = 1.000

  • 16284 measured reflections

  • 5871 independent reflections

  • 2694 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.232

  • S = 1.06

  • 5871 reflections

  • 328 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C22-C27 benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
C18-H18...S1i 0.93 2.87 3.743 (4) 156
C24-H24...F1ii 0.93 2.55 3.476 (5) 177
C28-H28B...F1iii 0.96 2.53 3.308 (5) 138
C27-H27...Cg1i 0.93 2.75 3.518 (4) 141
C14-H14...Cg2ii 0.93 2.85 3.756 (5) 164
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: SU2580 ).


Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.  [ISI] [ChemPort] [PubMed]
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Dong, W.-J., Cui, F.-H., Gao, Z.-L., Li, R.-S., Shen, G.-L. & Dong, H.-S. (2011). J. Heterocycl. Chem. 48, 1154-1160.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o618  [ doi:10.1107/S1600536813008179 ]

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