1-Methyl-4-phenyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidine

Abstract

In the title molecule, C 19 H 13 F 3 N 4 , the pyrazolopyrimidine unit is slightly nonplanar [dihedral angle between the five-and six-membered rings = 3.03 (15) ]. In the crystal, offset head-to-tail -stacking interactions between pyrazolopyrimidine units [centroid-centroid separation = 3.665 (2) Å ] together with weak C-HÁ Á ÁN hydrogen bonds form stepped chains propagating along the caxis direction. The structure was refined as a two-component twin. Structure descriptionPyrazolo [3,4-d] pyrimidine derivatives display a broad spectrum of biological properties, such as antiviral (Bektemirov et al., 1981), antibacterial (Rostamizadeh et al., 2013 and antitumor (Tintori et al., 2015). The present work is a continuation of our studies of pyrazolo [3,4-d]pyrimidine derivatives (El Hafi et al., 2017).In the title molecule (Fig. 1), the pyrazolopyrimidine unit is slightly non-planar as indicated by the dihedral angle of 3. 03 (15) between the mean planes of the five-and sixmembered rings. The plane of the C7-C12 benzene ring bearing the CF 3 substituent is inclined to the pyrazole moiety by 31.98 (16) while the plane of the C14-C19 benzene ring is inclined by 50.69 (14) to that of the pyrimidine ring. In the crystal, offset, head-to-tail -stacking interactions between adjacent pyrazolopyrimidine units reinforced by weak, complementary C6-H6BÁ Á ÁN1 hydrogen bonds form centrosymmetric dimers, which are connected into stepped chains along the c axis direction by weak, complementary C4-H4Á Á ÁN2 hydrogen bonds (Table 1 and Figs. 2 and 3). The centroid-centroid distance for the -stacking interaction is 3.665 (2) Å .