Synthesis and crystal structure of N'-(2-hydroxy-3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide

Abstract

N'-(2-hydroxy-3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide (1) was prepared by the reaction of p-Toluenesulfonyl hydrazide and 2-hydroxy-3-methoxy benzaldehyde (1:1 molar ratio) in ethanol under reflux condition. The crystal structure of the compound was determined by X-ray crystallography. Crystal data for 1 at -100 K: space group C/2c with: a = 15.807(1) Å, b = 10.457(1) Å, c = 20.779(1) Å, β = 109.68º (1). The final R value is 0.0574 for 3155 independent reflection. The N -H …O hydrogen bond converts the molecules into an infinite chain along [010].

Keywords


[1] Berredjem M., Bouasla R., Aouf N.-E., Barbey C., "Crystal Structure of 4-phenyl-piperazine-1-sulfonamide. X-ray Structure Analysis Online", 26 (2010) 13-14.

[2] Supuran C. T., Scozzafava A., Menabuoni L., Mincione F., Briganti F., Mincione G., "Synthesis and antiglaucoma propertis of metal complexes of p-flurobenolamid", Metal-Based Drugs 6 (1999) 67-73.

[3] Kremer E., Facchin G., Estévez E., Alborés P., Baran E. J., Ellena J., Torre M. H., "Copper complexes with heterocyclic sulfonamides: Synthesis, spectroscopic characterization, microbiological and SOD-like activities: Crystal structure of [Cu(sulfisoxazole)2(H2O)4] • 2H2O", J. Inorg. Biochem. 100 (2006) 1167-1175.

[4] Macíasa B., García I., Villa M. V., Borrás J., González-Álvarez M., Castiňeiras A., "Oxidative DNA damage of mixed copper(II) complexes with sulfonamides and 1,10-phenanthroline: Crystal structure of [Cu(Nquinolin-8-yl-p-toluenesulfonamidate)2(1,10-phenanthroline)].", J. Inorg. Biochem. 96 (2003) 367-374.

[5] Otter C. A., Couchman S. M., Jeffery J.C., Mann K. L. V., Psillakis E., Ward M. D., "Complexes of a new bidentate chelating pyridylkulfonamide ligand with copper(II), cobalt(II) and palladium(II): crystal structures and spectroscopic properties', Inorg. Chim. Acta 278 (1998) 178-184.

[6] Hirayama N., Taga J., Oshima S., Honjo T., "Sulfonamide-type di-Schiff base ligands as chelate extraction reagents for divalent metal cations", Analytica Chimica Acta 466 (2002) 295–301.

[7] Bernal M., García-Vázquez J.A., Romero J., Gómez C., Durán M.L., Sousa A., Sousa-Pedrares A., Rose D.J., Maresca K.P., Zubieta J., "Inorg. Chim." Acta 295 (1999) 39.

[8] García-Deibe A.M., Matalobos J.S., Fondo M., Vázquez M., Bermejo M.R., "Inorg. Chim.", Acta 357 (2004) 2561.

[9] Li S-N., Zhai Q.-G., Hu. M.-C., Jiang Y.-C. "Synthesis, crystal structures and characterization of three novel complexes with N-[2-(2-hydroxybenzylideneamino)ethyl]-4-methyl-benzene-sulfonamide as ligand", Inor. Chim. Acta 362 (2009) 2217–2221

[10] Tabatabaee M., Anari-Abbasnejad M., Nozari N., Sadegheian S., Ghasemzadeh M., "4-Methyl-N'-[(E)-4-methylbenzylidene]-benzenesulfonohydrazide.", Acta Crystallogr. E63 (2007) o2099-o2100.

[11] Tabatabaee M., Ghassemzadeh M., Hesami L., Neumuller B., "4-Methyl-N-[(E)-4-methyl-1-(4-methylphenylsulfonyl)-1,2-dihydropyridin-2-ylidene], Benzenesulfonamide". Acta Crystallogr. E66 (2010) o1891.

[12] Tabatabaee M., Hesami L., Ghassemzadeh M., Rothenberger A., "Crystal structure of (2Z)-N,3-ditosylthiazol-2(3H)-imine, C17H16N2O4S3", Z. Kristallogr. NCS 226 (2011) 273-274

[13] Tabatabaee M., Ghassemzadeh M., Zarabi B., Neumüller B., "Z. Naturforsch.", 61b (2006) 1421-1425

[14] Tabatabaee M., Ghassemzadeh M., Zarabi B., Heravi M. M., Anary-Abbasinejad M., Neumüller B., "Phosphorus, Sulfur Silicon Relat Elem.", 182 (2007) 677-686.

[15] Tabatabaee M., Ghassemzadeh M., Dehghan A. R., Khavasi H. R., Heravi M. M., "Acta Cryst.", E63 (2007) o42-o43.

[16] Tabatabaee M., Heravi M., Sharif M.A., Esfandiyari F., "Fast and Efficient Method for Imination of N-Aminorhodanine Using Inorganic Solid Support under Microwave Irradiation and Classical Heating", E-J Chem. 8 (2011) 535-540.

[17] Org. Syn. Coll. 5 (1973) 1055- 1960.

[18] Sheldrick G.M., "SHELXS-97, Program for Crystal Structure Determination"; University of. Göttingen: Germany, 1997.

[19] Sheldrick G.M., SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany (1997).

[20] Beloso I., Castro J., García-Vázquez J. A., Pérez-Lourido P., Romero J., Sousa A., "Different Coordinative (N,N) and (N,O) Bidentate Behaviour of N-2-Pyridyl-Sulfonamides. Electrochemical Synthesis and Characterization of Cadmium(II) Complexes.", Z. Anorg. Allg. Chem. 629 (2003) 275-284.

[21] Beloso I., Borrás J., Castro J., García-Vázquez J. A., Pérez-Lourido P., Romero J., Sousa A., "Flexidentate Behaviour of 2-Pyridylsulfonamides — Direct Electrochemical Synthesis and Spectroscopic and X-ray Characterisation of Neutral Copper(II) Complexes of N-(2-Pyridyl)sulfonamides". Eur. J. Inorg. Chem. (2004) 635-645.