Journal of Structural Chemistry

, Volume 47, Issue 5, pp 923–929

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

  • Yu. M. Chumakov
  • V. I. Tsapkov
  • G. Bocelli
  • B. Ya. Antonsyak
  • S. A. Palomares-Sánches
  • R. S. Ortiz
  • A. P. Gulya
Article

DOI: 10.1007/s10947-006-0409-2

Cite this article as:
Chumakov, Y.M., Tsapkov, V.I., Bocelli, G. et al. J Struct Chem (2006) 47: 923. doi:10.1007/s10947-006-0409-2

Abstract

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) Å, b = 12.622(3) Å, c = 14.414(3) Å; β = 104.31(3)°, space group P21/n, Z = 4, R = 0.0642. The crystals of II are also monoclinic, a = 10.313(2) Å, b = 11.288(2) Å, c = 15.766(3) Å; α = 99.37(3)°, space group P21/c, Z = 4, R = 0.0635. The crystals of III are triclinic, a = 10.567(2) Å, b = 10.849(2) Å, c = 18.432(4) Å; 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.

Keywords

condensation products azomethines sulfonamides streptocide norsulfazole ethazole biological activity 

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Yu. M. Chumakov
    • 1
  • V. I. Tsapkov
    • 2
  • G. Bocelli
    • 3
  • B. Ya. Antonsyak
    • 1
  • S. A. Palomares-Sánches
    • 4
  • R. S. Ortiz
    • 4
  • A. P. Gulya
    • 2
  1. 1.Institute of Applied PhysicsAcademy of Sciences of MoldovaChisinau
  2. 2.Moldova State UniversityChisinau
  3. 3.Istituto Materiali per Elettronica e MagnetismoParmaItalia
  4. 4.Facultad de CienciaUniversidad Autónoma de San Luis PotosíMexico

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