Synthesis and X-Ray Structure of ( 1 Z , 2 Z )-1 , 2-Bis ( 2-( phenylsulfonyl )-1-( 4-tolyl ) ethylidene ) hydrazine

The title compound (1Z,2Z)-1,2-bis(2-(phenylsulfonyl)-1-(4-tolyl)ethylidene)hydrazine (5) was prepared, in 78% yield, by the reaction of 2-(phenylsulfonyl)-1-(4-tolyl)ethan-1-one (3) with hydrazine hydrate in acetic acid at 90C under microwave irradiation in a closed vesselwith power 100Wfor 3min.The structure of the newly synthesized compoundwas establishedunder the basis of its IR,mass, HNMR, andX-ray single crystal analysis.The crystal of 5 belongs tomonoclinic space group,P2


Introduction
Hydrazones are a very important class of compounds with effective biological activities. They are found to possess anti-HIV [1], anticonvulsant [2], and antitubercular [3] activities. Furthermore, hydrazones have been reported as active antimicrobial agents where hydrazone function is the main scaffold in several marketed antimicrobial drugs such as the potent intestinal antiseptic drug nifuroxazide [4]. In addition, (Z)-N -(2-oxoindolin-3-ylidene)formohydrazide exhibited a good activity against S. aureus microbe which is almost similar to that of ciprofloxacin [5]. Moreover, hydrazone derivatives have been reported as potent anticancer agents; for example, the modulation of activity of the well-known anticancer drug doxorubicin occurred through a conjugation with fatty acyl and terphenyl hydrazones [6]. In addition, isatin-based hydrazones have been reported as active agents against multidrug-resistant cancer cells [7] whereas chromene-based hydrazones showed cytotoxicity against K562, MDA-MB-468, and HT-29 cell lines [8]. Furthermore, aroylhydrazone derivatives have been reported as inhibitors of carbonic anhydrases from the extremophilic bacteria SspCA and SazCA [9].
On the other hand, sulfones received a special interest due to their significant biological activity; for example, sulfone function is essential in the antimicrobial drug dapsone [10].
-Keto sulfones have been reported as key intermediates in the synthesis of several biologically active compounds [11]; for example, novel celecoxib analogs were synthesized as potent anti-inflammatory agents starting from some -keto sulfone derivatives [12].
In the light of previous research publications and in continuation of our interests in the synthesis of biologically active compounds containing hydrazone function and/or sulfone moiety [5,[7][8][9]12], we have reported in this study the microwave-assisted synthesis and X-ray single crystal 2 Journal of Chemistry analysis of the title compound which is a sulfone-based hydrazone derivative.

Chemistry
2.1.1. General. Melting point was determined on a Gallenkamp melting point apparatus and it is uncorrected. Infrared (IR) spectrum was recorded as KBr disks using the Perkin Elmer FT-IR Spectrum BX apparatus. NMR spectrum was scanned in DMSO-6 on a Bruker NMR spectrometer operating at 500 MHz for 1 H and 125 MHz for 13 C. Chemical shifts are expressed in -values (ppm) relative to TMS as an internal standard. Coupling constants ( ) are expressed in Hz. The mass spectrum was measured on an Agilent Triple Quadrupole 6410 QQQ LC/MS equipped with an ESI (electrospray ionization) source. The microwave irradiations were carried out in an Explorer-48 microwave reactor from CEM, USA. (3). To a solution of 2-bromo-1-(4-tolyl)ethan-1-one (1) (2.13 g, 10 mmol) in absolute ethanol (50 mL), sodium benzenesulfinate (2) (13 mmol) was added. The mixture was refluxed for 2 h and then left to cool. The reaction mixture was poured into cold water and the solid product was filtered off, washed with water, dried, and finally recrystallized from EtOH to afford compound 3 [13].
selected for X-ray diffraction analysis. Data were collected on a Bruker APEX-II CCD diffractometer equipped with graphite monochromatic CuK\ radiation ( = 1.54178) at 293 (2) K. Cell refinement and data reduction were done by Bruker SAINT; program used to solve structure and refine structure is SHELXS-97 [14]. The final refinement was performed by full-matrix least-squares techniques with anisotropic thermal data for nonhydrogen atoms on 2 . All the hydrogen atoms were placed in calculated positions and constrained to ride on their parent atoms. Multiscan absorption correction was applied by the use of SADABS software.
Selected bond distances (Å), bond angles ( ∘ ), and torsion angles ( ∘ ) of compound 5 are illustrated in Table 1. Hydrogen bonds geometry of the crystal 5 is showed in Table 2.

Conclusion
In conclusion, the title compound 5 was prepared efficiently by the reaction of sulfone 3 with hydrazine hydrate in acetic acid at 90 ∘ C/MWI/100 W/3 min. The 3D structure of the  newly synthesized compound 5 determined by X-ray single crystal analysis.