title: 2-Ethylsulfanyl-7-(furan-2-yl)-4-(thiophen-2-yl)pyrazolo[1,5-a][1,3,5]triazine: π-stacked chains of hydrogen-bonded R2(2)(10) dimers.
abstract: In the title compound, C(15)H(12)N(4)OS(2), the bond distances in the fused heterocyclic system show evidence for aromatic-type delocalization in the pyrazole ring with some bond fixation in the triazine ring. The thiophenyl substituent is slightly disordered over two sets of atomic sites having occupancies of 0.934 (4) and 0.066 (4). The non-H atoms in the entire molecule are nearly coplanar, with the planes of the furanyl substituent and the major orientation of the thiophenyl substituent making dihedral angles of 5.72 (17) and 1.8 (3)°, respectively, with that of the fused ring system. Molecules are linked into centrosymmetric R2(2)(10) dimers by C-H...O hydrogen bonds and these dimers are further linked into chains by a single π-π stacking interaction. Comparisons are made with some related 4,7-diaryl-2-(ethylsulfanyl)pyrazolo[1,5-a][1,3,5]triazines which contain variously substituted aryl groups in place of the furanyl and thiophenyl substituents in the title compound.
authors.affiliation: Departamento de Química, Universidad de Nariño, AA 1175 Pasto, Colombia.
authors.forename: Henry
authors.initials: H
authors.lastname: Insuasty
authors.affiliation: Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
authors.forename: Braulio
authors.initials: B
authors.lastname: Insuasty
authors.affiliation: Departamento de Química, Universidad de Nariño, AA 1175 Pasto, Colombia.
authors.forename: Edison
authors.initials: E
authors.lastname: Castro
authors.affiliation: Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain.
authors.forename: Justo
authors.initials: J
authors.lastname: Cobo
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D014227:Triazines / Q000737:chemistry*
chemical_list: C000593299:2-ethylsulfanyl-7-(furan-2-yl)-4-(thiophen-2-yl)pyrazolo(1,5-a)(1,3,5)triazine; D006571:Heterocyclic Compounds; D011720:Pyrazoles; D014227:Triazines
keywords: C—H...O hydrogen bonds; biologically active compounds; centrosymmetric dimers; crystal structure; pyrazolo[1,5-a][1,3,5]triazine; π–π stacking interactions