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

Abdel-Wahab, B.F.; Mohamed, H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813004492

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 (C-C) = 0.003 Å
R = 0.041
wR = 0.111
Data-to-parameter ratio = 17.5
Details

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

Bakr F. Abdel-Wahab,^a ⁺ Hanan A. Mohamed,^b Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^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-HN hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N-HS 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, 2012); Chimenti et al. (2010). For related structures, see: Chantrapromma et al. (2012); Abdel-Wahab et al. (2013).

Experimental

Crystal data

C₁₆H₁₃ClFN₃S
M_r = 333.80
Monoclinic, P 2₁ /c
a = 14.5402 (9) Å
b = 11.2700 (8) Å
c = 9.5169 (6) Å
= 103.850 (6)°
V = 1514.17 (17) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.898, T_max = 1.000
10191 measured reflections
3478 independent reflections
2570 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.111
S = 1.01
3478 reflections
199 parameters
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
N3-H31N1	0.88	2.24	2.617 (2)	106
N3-H31F1ⁱ	0.88	2.41	3.257 (2)	163
N3-H32S1ⁱⁱ	0.88	2.81	3.5203 (19)	139
C4-Cl1Cg1ⁱⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.
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.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds