Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Humayun Pervez (1) , Maqbool Ahmad (1) , Taibi B. Hadda (2) , Loic Toupet (3) , Muhammad Moazzam Naseer (4)

1 BZU - Bahauddin Zakariya University
2 Faculté des sciences [Oujda]
3 IPR - Institut de Physique de Rennes
4 Département de chimie

An exciting isatin-thiazoline hybrid molecule 2 having -C=N-N=C- linkage has been synthesized in 88% yield by the reaction of 5-fluoroisatin with N-(4-fluorophenyl)hydrazinecarbothioamide followed by condensation of the resultant isatin-thiosemicarbazone intermediate with p-chlorophenacyl bromide. The solid state self-assembly of this hybrid molecule was studied by X-ray crystallographic technique. A layered assembly composed of 1D-chains with methanol molecules encapsulated between every two chains is obtained, making a bi-chain sandwich like structure. The supramolecular forces involved in the stabilization of this structure are importantly fluorine-mediated interactions (C-H···F, F···S and F···π) along with others i.e. N-H···O, O-H···O, C-H···O, Cl···π, C-H···π and π···π interactions. To the best of our knowledge, this is the first example of solid state fluorine-mediated C-H···F, F···S and F···π interactions found in a family of isatin-based compounds

Keywords: isatin-thiazoline hybrid; layered structure; self-assembly; synthesis; fluorine-mediated interactions

Domains: Physics [physics]; Physics [physics]; Condensed Matter [cond-mat]; Materials Science [cond-mat.mtrl-sci]

Humayun Pervez, Maqbool Ahmad, Taibi B. Hadda, Loic Toupet, Muhammad Moazzam Naseer. Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid. Journal of Molecular Structure, 2015, 1098, pp.124-129. ⟨10.1016/j.molstruc.2015.06.013⟩. ⟨hal-01168327⟩