Crystal structures of condensation products of 3,5-dibromosalicylic aldehyde with streptocide, norsulfazole, and ethazole

• DOI: 10.1007/s10947-006-0409-2
• Publication Date: 2007-02-17T07:52:19Z
• Authors: Yu. M. Chumakov; V. I. Tsapkov; G. Bocelli; B. Ya. Antonsyak; S. A. Palomares-S...; R. S. Ortiz; A. P. Gulya
• Keywords: Triclinic crystal system; Monoclinic crystal system; Crystal (programming language)

Crystal structures of 4-[(3,5-dibromo-2-hydroxy-benzylidene)-amino]-benzenesulfonamide (I), 4-[(3,5-dibromo-2-hydroxy-benzylidene)-amino]-N-thiazol-2-yl-benzenesulfonamide (II), and 4-[((3,5-dibromo-2-hydroxy-benzylidene)-amino]-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-benzenesulfonamide (III) have been determined. The crystals of I are monoclinic, a = 8.645(2) A, b = 12.622(3) A, c = 14.414(3) A; β = 104.31(3)°, space group P21/n, Z = 4, R = 0.0642. The crystals of II are also monoclinic, a = 10.313(2) A, b = 11.288(2) A, c = 15.766(3) A; α = 99.37(3)°, space group P21/c, Z = 4, R = 0.0635. The crystals of III are triclinic, a = 10.567(2) A, b = 10.849(2) A, c = 18.432(4) A; α = 75.97(3)°, β = 89.71(3)°, γ = 87.33(3)°, space group P-1, Z = 4, R = 0.0644. The asymmetric part of the unit cell of compounds I and II contains a single molecule of the Schiff’s base, while in III two independent azomethine molecules A and B. The studied compounds I–III adopt the E-configuration relatively to the double azomethine bond C=N. Owing to phenolic oxygen together with nitrogen and oxygen atoms of the sulfonamide group, compound I makes in a crystalline state a two-dimensional hydrogen bonded network parallel to the plane (1 0 1). Compound II forms centrosymmetric dimers in the crystals via N-H…N hydrogen bonds. These dimers, in their turn, are connected by hydrogen bonds O-H…O into infinite chains running along the double screw axis b. As in II, molecules and of compound III form centrosymmetric dimers through hydrogen bonding N-H…N. These dimers are linked into infinite chains running along the c axis by hydrogen bonds C-H…O. The π-π-stacking interaction of aromatic rings is observed in all the compounds studied.