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

Abstract : 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
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Submitted on : Wednesday, November 18, 2015 - 9:50:11 AM
Last modification on : Wednesday, January 29, 2020 - 9:31:09 AM
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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, Elsevier, 2015, 1098, pp.124-129. ⟨10.1016/j.molstruc.2015.06.013⟩. ⟨hal-01168327⟩

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