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

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

doi:10.1107/S1600536813004339

Volume 69
Part 3
Pages o392-o393
March 2013

Received 13 February 2013
Accepted 13 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.048
wR = 0.117
Data-to-parameter ratio = 16.7
Details

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

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

^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, C₂₅H₂₀FN₃S, two independent molecules comprise the asymmetric unit, which differ in the relative orientation of the fluorobenzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two molecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the molecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thiazole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each molecule has a T-shape. In the crystal, molecules are connected into a three-dimensional architecture by weak C-H [pi] interactions.

Related literature

For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009, 2012); Chimenti et al. (2010). For a related structure, see: Fun et al. (2011).

Experimental

Crystal data

C₂₅H₂₀FN₃S
M_r = 413.50
Monoclinic, P c
a = 5.7563 (3) Å
b = 24.1214 (12) Å
c = 15.1827 (8) Å
= 90.948 (5)°
V = 2107.83 (19) Å³
Z = 4
Mo K radiation
= 0.18 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 = 0.837, T_max = 1.000
22651 measured reflections
9054 independent reflections
5841 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.117
S = 0.99
9054 reflections
543 parameters
2 restraints
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 4165 Friedel pairs
Flack parameter: -0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C26-C31, C45-C50, S2,N4,C32-C34 and C1-C6 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C15-H15Cg1	0.93	2.75	3.537 (3)	143
C19-H19ACg2ⁱ	0.96	2.94	3.596 (4)	127
C35-H35Cg3ⁱⁱ	0.98	2.94	3.843 (3)	153
C42-H42Cg4ⁱⁱⁱ	0.93	2.86	3.567 (3)	134
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

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), QMol (Gans & Shalloway, 2001) 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: HG5292 ).

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.
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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Fun, H.-K., Arshad, S., Himaja, M., Munirajasekhar, D. & Sarojini, B. K. (2011). Acta Cryst. E67, o2412.
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds