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<p>The design of organic molecular crystals with tailored properties requires a detailed understanding of the non-covalent interactions governing their assembly. In this context, a novel triazole–quinoxaline derivative, 1-((1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl)methyl)-3-phenylquinoxalin-2(1H)-one, was synthesized and characterized both structurally and computationally in the solid state. The asymmetric unit contains two independent molecules (A and B, Z’ = 2) and two water molecules, which form a three-dimensional supramolecular network through O–H⋯O, C–H⋯N, π–π, and C–H⋯π interactions. Crystallographic analysis reveals subtle conformational differences between A and B that are correlated with variations in π–π stacking geometries and hydrogen-bonding patterns, reflecting the interplay between conformational flexibility and supramolecular assembly. Hirshfeld surface analysis quantifies contact contributions, while MEP mapping rationalizes noncovalent interaction preferences, and energy framework calculations provide the energetic basis of the crystal structure, including the role of solvent water molecules. Cooperative effects within the water-mediated O–H⋯O network were investigated using two trimers (A⋯water⋯B) employing density functional theory (B3LYP-D3(BJ)/def2-TZVPP), and both trimers exhibit positive cooperativity. Furthermore, QTAIM and NBO analyses reveal systematic increases in electron density at bond critical points and enhancements in donor–acceptor stabilization energies when both hydrogen bonds are present.</p> Graphical abstract <p></p>

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Interplay and cooperativity of non-covalent interactions in water-mediated supramolecular assembly of a 1,2,3-triazole–quinoxalin-2-one derivative

  • 期刊论文

  • 发表日期：

    2026年6月16日

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  • Shafeek Buhlak,
  • Melek Hajji,
  • Intissar Nchioua,
  • Joel T. Mague,
  • Hanan Al‑Ghulikah,
  • El Mokhtar Essassi,
  • Youssef Ramli,
  • Nadeem Abad

摘要

The design of organic molecular crystals with tailored properties requires a detailed understanding of the non-covalent interactions governing their assembly. In this context, a novel triazole–quinoxaline derivative, 1-((1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl)methyl)-3-phenylquinoxalin-2(1H)-one, was synthesized and characterized both structurally and computationally in the solid state. The asymmetric unit contains two independent molecules (A and B, Z’ = 2) and two water molecules, which form a three-dimensional supramolecular network through O–H⋯O, C–H⋯N, π–π, and C–H⋯π interactions. Crystallographic analysis reveals subtle conformational differences between A and B that are correlated with variations in π–π stacking geometries and hydrogen-bonding patterns, reflecting the interplay between conformational flexibility and supramolecular assembly. Hirshfeld surface analysis quantifies contact contributions, while MEP mapping rationalizes noncovalent interaction preferences, and energy framework calculations provide the energetic basis of the crystal structure, including the role of solvent water molecules. Cooperative effects within the water-mediated O–H⋯O network were investigated using two trimers (A⋯water⋯B) employing density functional theory (B3LYP-D3(BJ)/def2-TZVPP), and both trimers exhibit positive cooperativity. Furthermore, QTAIM and NBO analyses reveal systematic increases in electron density at bond critical points and enhancements in donor–acceptor stabilization energies when both hydrogen bonds are present.

Graphical abstract