3,6-Dimethyl-1-phenyl-4-(2-thienyl)-8-(2-thienylmethylene)-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-b][1,6]naphthyridine

Abstract

In the mol­ecule of the title compound, C26H22N4S2, the pyrazole ring is oriented at a dihedral angle of 0.85 (3)° with respect to the adjacent naphthyridine ring, while the other ring of naphthyridine adopts an envelope conformation. The dihedral angle between phenyl and pyrazole rings is 87.65 (3)°. In the crystal structure, weak inter­molecular C—H⋯N inter­actions link the mol­ecules into chains. The π–π contacts between the naphthyridine rings and the naphthyridine and thio­phene rings [centroid–centroid distances = 3.766 (3) and 3.878 (3) Å] may further stabilize the structure. A weak C—H⋯π inter­action is also present.

7-(4-Methoxyphenyl)-4,9-dimethyl-N-(4-methylphenyl)-5,12-diazatetraphen-6-amine

“…The bond lengths and angles are in the normal ranges (Allen et al, 1987). The fused tetracyclic ring system is essentially planar in geometry as was previously reported for a related compounds (Vennila et al, 2010(Vennila et al, , 2011Seebacher et al 2010;Peng et al 2009 In the crystal, weak intermolecular C-H•••N hydrogen bonds link the molecules into centrosymmetric dimers forming R 2 2 (14) motifs (Bernstein et al, 1995) (see Fig. 2).…”

“…For the biological activity of naphthyridine derivatives, see: Gopalsamy et al (2007); Kim et al (2009); Nittoli et al (2010); Bedard et al (2000). For the structures of related naphthrydine derivatives, see: Peng et al (2009); Seebacher et al . (2010); Vennila et al (2010Vennila et al ( , 2011.…”

Two isostructural 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-ones: disorder and supramolecular assembly

“…In contrast to the simplicity of the molecular constitution of (III) above, in most other structures containing both pyrazole and thiophene units, at least one of the rings is fused. In 3,6dimethyl-1-phenyl-4-(thiophen-2-yl)-8-(thiophen-2-ylmethylene)-5,6,7,8-tetrahydro-1H-pyrazolo[3,4-b][1,6]naphthyridine (IV) (Peng et al, 2009), the molecules are linked into C(11) chains by means of C-HÁ Á ÁN hydrogen bonds. The molecules of 2- (Ahmad et al, 2010) are linked by a combination of N-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds: although the resulting aggregation was described as consisting of dimers, the molecules are, in fact, linked into chains of rings, as clearly illustrated in the original report.…”