Abstract
The molecule of the title compound, C26H17ClFN3OS, comprises benzofuranyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) ring systems. Rings A–D are almost coplanar, as indicated by the twist angles between the ring pairs A/B, B/C and C/D of 7.6 (1), 4.7 (1) and 6.9 (2)°, respectively. Ring E is twisted by 73.2 (1)° from the plane through ring C. In the crystal, pairwise C—H...F interactions link the molecules into inversion dimers. Aromatic π–π interactions are also observed between rings A and E and between rings B and C for neighbouring pairs of molecules related by inversion symmetry. Taken together, the weak interactions generate [010] chains.
Highlights
The molecule of the title compound, C26H17ClFN3OS, comprises benzofuranyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) ring systems
Pairwise C—HÁ Á ÁF interactions link the molecules into inversion dimers
Aromatic – interactions are observed between rings A and E and between rings B and C for neighbouring pairs of molecules related by inversion symmetry
Summary
Compounds containing a benzofuran moiety are present in many important natural products and drugs (Naik et al, 2015). The molecule of the title compound comprises benzofuranyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) ring systems (Fig. 1). Pairwise C—HÁ Á ÁF interactions link molecules into inversion dimers (Table 1). Aromatic – interactions are observed between rings A and E [centroid– centroid separation = 3.755 (2) A ] and between rings B and C [3.796 (2) A ] for neighbouring pairs of molecules related by inversion symmetry; this results in each pair of molecules being linked by four – interactions (Fig. 2). Synthesis and crystallization The title compound was synthesized from the condensation of molar equivalents of 3-(4-chlorophenyl)-5-(4-fluorophenyl)4,5-dihydro-1H-pyrazole-1-carbothioamide with 1-(benzofuran-2-yl)-2-bromoethanone in anhydrous ethanol under reflux for 2 h. The crude product was recrystallized from dimethylformamide solution to give colourless needles (yield 74%, m.p. 234–236 C)
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