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Volume 69 
Part 5 
Page o735  
May 2013  

Received 25 March 2013
Accepted 11 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.010 Å
R = 0.052
wR = 0.136
Data-to-parameter ratio = 15.2
Details
Open access

2-[3-(4-Bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thiazole

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, C24H17BrFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.043 Å), with all but the perpendicular fluorobenzene ring substituents [dihedral angle = 77.9 (3)°] being very approximately coplanar [dihedral angle with the 2-thienyl ring = 19.4 (3)° and with the bromobenzene ring = 20.3 (3)°; dihedral angle between the 2-thienyl and attached phenyl ring = 11.0 (4)°], so that the molecule has a T-shape. In the crystal, supramolecular chains along the b-axis direction are sustained by C-H...S and C-Br...[pi] interactions.

Related literature

For the biological activities and synthesis of pyrazolin-1-carbothioamides, 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.]); Lv et al. (2011[Lv, P.-C., Li, D.-D., Li, Q.-S., Lu, X., Xiao, Z.-P. & Zhu, H.-L. (2011). Bioorg. Med. Chem. Lett. 21, 5374-5377.]). For a related structure, see: Abdel-Wahab et al. (2013[Abdel-Wahab, B. F., Mohamed, H. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o392-o393.]).

[Scheme 1]

Experimental

Crystal data
  • C24H17BrFN3S

  • Mr = 478.38

  • Monoclinic, P 21

  • a = 13.747 (2) Å

  • b = 5.6695 (13) Å

  • c = 14.280 (3) Å

  • [beta] = 106.94 (2)°

  • V = 1064.7 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.05 mm-1

  • T = 295 K

  • 0.30 × 0.10 × 0.02 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 = 0.937, Tmax = 1.000

  • 7430 measured reflections

  • 4124 independent reflections

  • 1947 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.136

  • S = 0.95

  • 4124 reflections

  • 271 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1440 Friedel pairs

  • Flack parameter: -0.022 (15)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13-C18 benzene ring.

D-H...A D-H H...A D...A D-H...A
C4-H4...S1i 0.98 2.84 3.734 (7) 153
C22-Br1...Cg1ii 1.897 (6) 3.644 (3) 5.265 (7) 141.6 (3)
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+2].

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: QM2094 ).


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]
Abdel-Wahab, B. F., Mohamed, H. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o392-o393.  [CrossRef] [ChemPort] [details]
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Lv, P.-C., Li, D.-D., Li, Q.-S., Lu, X., Xiao, Z.-P. & Zhu, H.-L. (2011). Bioorg. Med. Chem. Lett. 21, 5374-5377.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o735  [ doi:10.1107/S1600536813010039 ]

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