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

Abstract EN

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 90°C under microwave irradiation in a closed vessel with power 100 W for 3 min.

The structure of the newly synthesized compound was established under the basis of its IR, mass, 1H NMR, and X-ray single crystal analysis.

The crystal of 5 belongs to monoclinic space group, P 2 1 / c , with a = 5.2944 (3) Å, b = 17.5748 (9) Å, c = 15.4701 (8) Å, β = 105.767 (4)°, Z = 2 , V = 1385.30 (13) Å3, D c = 1.306 Mg m−3, μ = 2.05 mm−1, F ( 000 ) = 572 , R = 0.075 , and w R = 0.224 for 1419 observed reflections with I > 2 σ ( I ) .

The asymmetric unit of compound 5 contains one molecule with Z configuration about the C7=N1 and C7A=N1A double bond.

This Z configuration of 5 is stabilized by intramolecular hydrogen bonds C1–H1A⋯N1 and C1A–H1AA⋯N1A.

The molecular packing in the crystal structure of 5 is stabilized by intermolecular interactions forming a three-dimensional network.