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<p>Single-crystal X-ray diffraction and supramolecular analysis were performed for three bioactive triazole-3-thione derivatives 1–3 featuring an adamantan-1-yl, (4-arylpiperazin-1-yl)methyl, and an arylideneamino moieties as the main substituents. Although all compounds share this molecular scaffold, differences in the substitution pattern of the aryl rings attached to the piperazine and arylideneamino fragments lead to distinct crystal packing motifs. The supramolecular arrangement was interpreted in terms of directional interactions such as C–H···O, C–H···N, C–H···F, and C–H···π, whose role in the supramolecular architecture was evaluated using electrostatic potential maps and Hirshfeld surface analysis. Among the three structures, compound 2 is the only one crystallizing in a non-centrosymmetric space group as a consequence of the lack of the inversion centers observed in compounds 1 and 3. In the case of compound 3, the incorporation of fluorine atoms gives rise to multiple C–H···F contacts that define a unique packing behavior and highlight the impact of fluorination on the solid-state organization.</p>

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Crystal structures of three bioactive adamantane-linked 1,2,4-triazoles depicting the influence of sulfur and fluorine atoms in the crystal packing

  • 期刊论文

  • 发表日期：

    2026年2月5日

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  • Lamya H. Al-Wahaibi,
  • Kevin Salamanca-Perdigón,
  • Olivier Blacque,
  • Hanan M. Hassan,
  • Mario A. Macías,
  • Ali A. El-Emam

摘要

Single-crystal X-ray diffraction and supramolecular analysis were performed for three bioactive triazole-3-thione derivatives 1–3 featuring an adamantan-1-yl, (4-arylpiperazin-1-yl)methyl, and an arylideneamino moieties as the main substituents. Although all compounds share this molecular scaffold, differences in the substitution pattern of the aryl rings attached to the piperazine and arylideneamino fragments lead to distinct crystal packing motifs. The supramolecular arrangement was interpreted in terms of directional interactions such as C–H···O, C–H···N, C–H···F, and C–H···π, whose role in the supramolecular architecture was evaluated using electrostatic potential maps and Hirshfeld surface analysis. Among the three structures, compound 2 is the only one crystallizing in a non-centrosymmetric space group as a consequence of the lack of the inversion centers observed in compounds 1 and 3. In the case of compound 3, the incorporation of fluorine atoms gives rise to multiple C–H···F contacts that define a unique packing behavior and highlight the impact of fluorination on the solid-state organization.