4-Phenyl-5-(2-Thienylmethyl)-2,4-Dihydro-3h-1,2,4-Triazole-3-Selone And 3,3'-Di[4-Phenyl-5-(2-Thienylmethyl)-4h-1,2,4-Triazolyl] Diselenide: Synthesis, Structures, And Biocidal Properties

Three new organoselenium compounds are synthesized: N-phenyl-2-(2-thienylacetyl)hydrazinecarboselenoamide (I), 4-phenyl-5-(2-thienylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-selone (II), and 3,3'-di[4-phenyl-5-(2-thienylmethyl)-4H-1,2,4-triazolyl] diselenide (III). Two of them (compounds II and III) are characterized by X-ray diffraction analysis (CIF files CCDC nos. 1956602 (II) and 1956603 (III)). Compound II crystallizes in the monoclinic crystal system (space group P2(1)/n) with two crystallographically independent molecules A and B being different conformers relative to rotation about the N-Trz-C-Trz-C(H-2)-C-Tph bond, where Trz is triazole and Tph is thiophene (gauche-A (51.4(3)degrees) and cis-B (4.2(4)degrees)). In the crystal of compound II, molecules A and B form chains along the crystallographic axis a due to strong hydrogen bonds N-H center dot center dot center dot Se. Then the chains are bound into a three-dimensional framework via intermolecular nonvalent interactions Se center dot center dot center dot S (3.3857(11) angstrom). Owing to the anomeric effect, diselenide III is characterized by the typical gauche conformation of the substituents at the Se-Se bond (torsion angle CSeSeC 83.5(4)degrees) stabilized by a weak intramolecular hydrogen bond C-H center dot center dot center dot pi. In the crystal of compound III, the molecules form chains along the crystallographic acid b due to intermolecular noncovalent interactions Se center dot center dot center dot pi(C-C) (3.404(6) and 3.458(12) angstrom), Se center dot center dot center dot Se (3.8975(11) angstrom), and S center dot center dot center dot N (3.250(5) angstrom). Bactericidal and fungicidal activity of the synthesized compounds is studied.