5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide

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

doi:10.1107/S1600536813004194

Volume 69
Part 3
Pages o385-o386
March 2013

Received 11 February 2013
Accepted 12 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.122
Data-to-parameter ratio = 17.5
Details

5-(4-Fluorophenyl)-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

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

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt,^bChemical Industries Division, National Research Centre, Dokki, 12622, Giza, 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

The central pyrazole ring in the title compound, C₁₇H₁₆FN₃S, adopts an envelope conformation with the methine C atom bearing the 4-fluorophenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluorobenzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thioamide group is almost coplanar with the N-N bond of the ring [N-N-C-N torsion angle = 1.2 (3)°] and the amine group forms an intramolecular hydrogen bond with a ring N atom. In the crystal, supramolecular double layers in the bc plane are formed via N-HS, N-HF and C-HF interactions.

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: Nonthason et al. (2011); Chantrapromma et al. (2012).

Experimental

Crystal data

C₁₇H₁₆FN₃S
M_r = 313.39
Monoclinic, P 2₁ /c
a = 14.4154 (10) Å
b = 11.3197 (9) Å
c = 9.5575 (8) Å
= 103.991 (8)°
V = 1513.3 (2) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 295 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.772, T_max = 1.000
9303 measured reflections
3500 independent reflections
2370 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.122
S = 1.04
3500 reflections
200 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H31N2	0.88	2.23	2.611 (3)	106
N3-H31F1ⁱ	0.88	2.41	3.255 (2)	162
N3-H32S1ⁱⁱ	0.88	2.83	3.538 (2)	138
C16-H16BF1ⁱⁱⁱ	0.96	2.55	3.478 (3)	163
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y+1, -z+1.

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: HG5291 ).

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.
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.
Nonthason, P., Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3501-o3502.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds