TY - JOUR
T1 - 2-Ethylsulfanyl-7-(furan-2-yl)-4-(thiophen-2-yl)pyrazolo[1,5-a][1,3,5]triazine: π-stacked chains of hydrogen-bonded R22(10) dimers
AU - Insuasty, H.
AU - Insuasty, B.
AU - Castro, E.
AU - Cobo, J.
AU - Glidewell, Christopher
N1 - JC thanks the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain), the Universidad de Jaén (project reference UJA_07_16_33) and Ministerio de Ciencia e Innovación (project reference SAF2008-04685-C02-02) for financial support.
PY - 2014/9/15
Y1 - 2014/9/15
N2 - In the title compound, C15H12N4OS2, 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 R22(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.
AB - In the title compound, C15H12N4OS2, 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 R22(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.
KW - Crystal structure
KW - Centrosymmetric dimers
KW - C-H...O hydrogen bonds
KW - [pi]-[pi] stacking interactions
KW - Biologically active compounds
KW - Pyrazolo[1,5-a][1,3,5]triazine
UR - http://scripts.iucr.org/cgi-bin/sendsup?cnor=sk3556&type=supplementarymaterials
U2 - 10.1107/S2053229614018877
DO - 10.1107/S2053229614018877
M3 - Article
AN - SCOPUS:84921696293
SN - 2053-2296
VL - 70
SP - 908
EP - 911
JO - Acta Crystallographica Section C Structural Chemistry
JF - Acta Crystallographica Section C Structural Chemistry
ER -