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.

中文翻译：

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卤素取代基的类型及其位置对一系列1-苯甲酰基-3-（卤代苯基）硫脲的分子构象，分子间相互作用和晶体堆积的影响

通过苯甲酰氯，异硫氰酸钾和适当的卤代苯胺，即2/3 / 4-（溴/碘）苯胺的反应，我们获得了五种新的1-苯甲酰基-3-（卤代苯基）硫脲，即1-苯甲酰基- 3-（2-溴苯基）硫脲和1-苯甲酰基-3-（3-溴苯基）硫脲，C ₁₄ H ₁₁ BrN ₂ OS和1-苯甲酰基-3-（2-碘苯基）硫脲，1-苯甲酰基-3- （3-碘苯基）硫脲和1-苯甲酰基-3-（4-碘苯基）硫脲，C ₁₄ H ₁₁ IN ₂ OS。使用X射线衍射和理论计算分析了化合物的结构和构象特征。新型化合物的特征在于固态红外光谱和¹ H / ¹³13 C NMR光谱。构象和分子间的相互作用，例如氢键，π–π和S（6）…π堆积以及X …O（X  = I或Br），I…S和I…π，已一起进行了检查和合理化与先前文献中所述的四种类似化合物的混合物。选择这9种化合物来检验卤素原子的变化及其在苯环上的位置如何影响分子和晶体结构。