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

Bakr F Abdel-Wahab; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536813008179

. 2013 Mar 28;69(Pt 4):o618. doi: 10.1107/S1600536813008179

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

Bakr F Abdel-Wahab ^a,^‡, Seik Weng Ng ^b,^c, Edward R T Tiekink ^b,^*

PMCID: PMC3629653 PMID: 23634140

Abstract

In the title compound, C₂₈H₂₃FN₆S, the pyrazole ring adopts an envelope conformation, with the methine C atom being the flap atom. With respect to this ring, the 2-thienyl, triazole and fluorobenzene rings are approximately coplanar, coplanar and perpendicular, respectively [dihedral angles = 8.56 (17), 6.03 (19) and 73.1 (2)°, respectively] so that to a first approximation the molecule has a T-shape. In the crystal, molecules are consolidated into a three-dimensional architecture by C—H⋯F (involving a bifurcated F atom), C—H⋯S and C—H⋯π interactions.

Related literature

For the synthesis, structure and biological activity of 1-thiazol-2-ylpyrazoline, see: Abdel-Wahab et al. (2012 ▶); Dong et al. (2011 ▶). graphic file with name e-69-0o618-scheme1.jpg

Experimental

Crystal data

C₂₈H₂₃FN₆S
M _r = 494.58
Monoclinic,
a = 17.7373 (18) Å
b = 7.8367 (7) Å
c = 19.4159 (18) Å
β = 109.323 (11)°
V = 2546.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.16 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 = 0.901, T _max = 1.000
16284 measured reflections
5871 independent reflections
2694 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.065
wR(F ²) = 0.232
S = 1.06
5871 reflections
328 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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 Material

Click here for additional data file.^{(24.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008179/su2580sup1.cif

e-69-0o618-sup1.cif^{(24.7KB, cif)}

Click here for additional data file.^{(287.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008179/su2580Isup2.hkl

e-69-0o618-Isup2.hkl^{(287.4KB, hkl)}

Click here for additional data file.^{(9.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813008179/su2580Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1–C6 and C22–C27 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯S1ⁱ	0.93	2.87	3.743 (4)	156
C24—H24⋯F1ⁱⁱ	0.93	2.55	3.476 (5)	177
C28—H28B⋯F1ⁱⁱⁱ	0.96	2.53	3.308 (5)	138
C27—H27⋯Cg1ⁱ	0.93	2.75	3.518 (4)	141
C14—H14⋯Cg2ⁱⁱ	0.93	2.85	3.756 (5)	164

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

supplementary crystallographic information

Comment

The title compound, (I), was characterized in relation to on-going studies into the synthesis, structure and biological activities of 1-thiazol-2-ylpyrazoline derivatives (Abdel-Wahab et al., 2012; Dong et al., 2011).

In (I), the pyrazolyl ring adopts an envelope conformation with the methine-C10 atom being the flap atom. The 2-thienyl and triazole rings are approximately co-planar with the central five-membered ring forming dihedral angles of 8.56 (17) and 6.03 (19)°, respectively; the dihedral angle between these rings is 14.33 (17)°, indicating an overall twist in the molecule. By contrast, the fluorobenzene ring is almost perpendicular to the pyrazolyl ring, forming a dihedral angle of 73.1 (2)°. With respect to the respective attached five-membered ring, the phenyl and p-tolyl residues form dihedral angles of 2.88 (17) and 45.58 (18)°, respectively, indicating co-planar and inclined dispositions. Overall, the shape of the molecule resembles the distorted T-shape reported for the chlorobenzene derivative (Dong et al., 2011).

The three-dimensional architecture is consolidated by C—H···F, involving a bifurcated F1 atom, C—H···S and C—H···π interactions, Fig. 2 and Table 1.

Experimental

The title compound was prepared according to the reported method (Abdel-Wahab et al., 2012). Beige crystals were obtained from its DMF solution by slow evaporation at room temperature.