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Volume 69 
Part 3 
Pages o414-o415  
March 2013  

Received 14 February 2013
Accepted 14 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.111
Data-to-parameter ratio = 17.5
Details
Open access

3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt,bDepartment of Chemistry, Faculty of Science, Mansoura University, ET-35516 Mansoura, Egypt,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C16H13ClFN3S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluorobenzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intramolecular N-H...N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N-H...S hydrogen bonding leads to a supramolecular chain along the c axis. Connections between chains of the type Cl...[pi] lead to a layer in the bc plane.

Related literature

For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009[Abdel-Wahab, B. F., Abdel-Aziz, H. A. & Ahmed, E. M. (2009). Eur. J. Med. Chem. 44, 2632-2635.], 2012[Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.]); Chimenti et al. (2010[Chimenti, F., Carradori, S., Secci, D., Bolasco, A., Bizzarri, B., Chimenti, P., Granese, A., Yáñez, M. & Orallo, F. (2010). Eur. J. Med. Chem. 45, 800-804.]). For related structures, see: Chantrapromma et al. (2012[Chantrapromma, S., Nonthason, P., Suwunwong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o830-o831.]); Abdel-Wahab et al. (2013[Abdel-Wahab, B. F., Mohamed, H. A., Khidre, R. E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o386.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13ClFN3S

  • Mr = 333.80

  • Monoclinic, P 21 /c

  • a = 14.5402 (9) Å

  • b = 11.2700 (8) Å

  • c = 9.5169 (6) Å

  • [beta] = 103.850 (6)°

  • V = 1514.17 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.40 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 = 0.898, Tmax = 1.000

  • 10191 measured reflections

  • 3478 independent reflections

  • 2570 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.111

  • S = 1.01

  • 3478 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
N3-H31...N1 0.88 2.24 2.617 (2) 106
N3-H31...F1i 0.88 2.41 3.257 (2) 163
N3-H32...S1ii 0.88 2.81 3.5203 (19) 139
C4-Cl1...Cg1iii 1.735 (2) 3.9240 (12) 4.183 (2) 86.17 (17)
Symmetry codes: (i) x, y, z+1; (ii) [x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 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: HG5293 ).


Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Abdel-Wahab, B. F., Abdel-Aziz, H. A. & Ahmed, E. M. (2009). Eur. J. Med. Chem. 44, 2632-2635.  [ISI] [PubMed] [ChemPort]
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., Khidre, R. E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o386.
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chantrapromma, S., Nonthason, P., Suwunwong, T. & Fun, H.-K. (2012). Acta Cryst. E68, o830-o831.  [CSD] [CrossRef] [details]
Chimenti, F., Carradori, S., Secci, D., Bolasco, A., Bizzarri, B., Chimenti, P., Granese, A., Yáñez, M. & Orallo, F. (2010). Eur. J. Med. Chem. 45, 800-804.  [ISI] [CrossRef] [PubMed] [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, o414-o415   [ doi:10.1107/S1600536813004492 ]

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