The influence of the type of halogen substituent and its position on the molecular conformation, intermolecular interactions and crystal packing for a series of 1-benzoyl-3-(halogenophenyl)thioureas

Abstract

By the reaction of benzoyl chloride, potassium isothiocyanate and the appropriate halogenoaniline, i.e. 2/3/4-(bromo/iodo)aniline, we have obtained five new 1-benzoyl-3-(halogenophenyl)thioureas, namely, 1-benzoyl-3-(2-bromophenyl)thiourea and 1-benzoyl-3-(3-bromophenyl)thiourea, C14H11BrN2OS, and 1-benzoyl-3-(2-iodophenyl)thiourea, 1-benzoyl-3-(3-iodophenyl)thiourea and 1-benzoyl-3-(4-iodophenyl)thiourea, C14H11IN2OS. Structural and conformational features of the compounds have been analyzed using X-ray diffraction and theoretical calculations. The novel compounds were characterized by solid-state IR and 1H/13C NMR spectroscopy. The conformations and intermolecular interactions, such as hydrogen bonds, π–π and S(6)...π stacking, and X...O (X = I or Br), I...S and I...π, have been examined and rationalized, together with four analogous compounds described previously in the literature. The set of nine compounds was chosen to examine how a change of the halogen atom and its position on the phenyl ring affects the molecular and crystal structures.

Structural systematics in isomorphous binary co-crystal solvates comprising 2,2′-dithiodibenzoic acid, 4-halobenzoic acid and dimethylformamide (1 : 1 : 1), for halide = chloride, bromide and iodide

“…29,30 In the organic solid-state, such considerations have attracted many systematic studies. [31][32][33][34][35][36][37][38][39][40][41][42][43][44] While these studies have largely focussed upon singlecomponent crystals, increasingly, attention has been directed to evaluating similar phenomena in multi-component crystals. [45][46][47][48][49][50][51] Not surprisingly, the majority of the aforementioned studies of both single-and multi-component crystals involve the interchange of halides.…”