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Polymorphism in N-(5-methylisoxazol-3-yl)malonamide: understanding the supramolecular structure and the crystallization mechanism
CrystEngComm ( IF 2.6 ) Pub Date : 2023-08-16 , DOI: 10.1039/d3ce00643c Anderson B. Pagliari 1 , Jéssica M. L. Rosa 1 , Priscila S. V. de Lima 1 , Geórgia C. Zimmer 1 , Maria E. C. da Silva 1 , Érica G. de Oliveira 1 , Helio G. Bonacorso 1 , Nilo Zanatta 1 , Marcos A. P. Martins 1
CrystEngComm ( IF 2.6 ) Pub Date : 2023-08-16 , DOI: 10.1039/d3ce00643c Anderson B. Pagliari 1 , Jéssica M. L. Rosa 1 , Priscila S. V. de Lima 1 , Geórgia C. Zimmer 1 , Maria E. C. da Silva 1 , Érica G. de Oliveira 1 , Helio G. Bonacorso 1 , Nilo Zanatta 1 , Marcos A. P. Martins 1
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The supramolecular architectures of amide-containing compounds are highly dependent on the side-chain substituents, although the potential impact of isoxazole substituents on polymorph formation has not been thoroughly explored. Hence, three distinct forms of N1,N3-bis(5-methylisoxazol-3-yl)malonamide (1) were obtained and characterized: two polymorphic forms and one solvate. An in-depth analysis of the interactions and energy content of the crystals based on supramolecular clusters allowed us to propose crystallization mechanisms (crystal retrosynthesis). Specifically, the energy similarities between the interaction of the first sites NHamide⋯O![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
Camide (form 1I) and the symmetric sites NHamide⋯Nisox (form 1II) were found to contribute to their formation. Nonetheless, the presence of DMSO resulted in the formation of form 1III, where the solvent molecule disrupted amide-amide interactions. The first nuclei are more stable than forms 1I and 1II. The compound of N1,N2-bis(5-methylisoxazol-3-yl)oxalamide (2) was used as a comparison, and through the absence of polymorphs, revealed that the central carbon in molecule 1 allows a flexible adaptation that leads to the three forms. These findings suggest that variations in solvents, flexibility, and the presence/absence of amide–amide interactions can modulate the competition between amide-containing isoxazole compounds.
中文翻译：
N-(5-甲基异恶唑-3-基)丙二酰胺的多态性：了解超分子结构和结晶机制
尽管异恶唑取代基对多晶型物形成的潜在影响尚未得到彻底探索，但含酰胺化合物的超分子结构高度依赖于侧链取代基。因此，获得并表征了N 1 , N 3 -双(5-甲基异恶唑-3-基)丙二酰胺( 1 )的三种不同形式：两种多晶型形式和一种溶剂化物。对基于超分子簇的晶体的相互作用和能量含量的深入分析使我们能够提出结晶机制（晶体逆合成）。具体来说，第一个位点 NH酰胺⋯OC酰胺（形式1I ) 和对称位点 NH amide ⋯N isox ( 1II型)被发现有助于它们的形成。尽管如此，DMSO 的存在导致形成1III型，其中溶剂分子破坏了酰胺-酰胺相互作用。第一个核比1I和1II型更稳定。以化合物N 1 , N 2 -双(5-甲基异恶唑-3-基)草酰胺( 2 )作为对比，通过不存在多晶型物，揭示分子1中的中心碳允许灵活的适应，从而产生三种形式。这些发现表明，溶剂、灵活性以及酰胺-酰胺相互作用的存在/不存在的变化可以调节含酰胺异恶唑化合物之间的竞争。
更新日期：2023-08-16
Camide (form 1I) and the symmetric sites NHamide⋯Nisox (form 1II) were found to contribute to their formation. Nonetheless, the presence of DMSO resulted in the formation of form 1III, where the solvent molecule disrupted amide-amide interactions. The first nuclei are more stable than forms 1I and 1II. The compound of N1,N2-bis(5-methylisoxazol-3-yl)oxalamide (2) was used as a comparison, and through the absence of polymorphs, revealed that the central carbon in molecule 1 allows a flexible adaptation that leads to the three forms. These findings suggest that variations in solvents, flexibility, and the presence/absence of amide–amide interactions can modulate the competition between amide-containing isoxazole compounds.
中文翻译：
N-(5-甲基异恶唑-3-基)丙二酰胺的多态性：了解超分子结构和结晶机制
尽管异恶唑取代基对多晶型物形成的潜在影响尚未得到彻底探索，但含酰胺化合物的超分子结构高度依赖于侧链取代基。因此，获得并表征了N 1 , N 3 -双(5-甲基异恶唑-3-基)丙二酰胺( 1 )的三种不同形式：两种多晶型形式和一种溶剂化物。对基于超分子簇的晶体的相互作用和能量含量的深入分析使我们能够提出结晶机制（晶体逆合成）。具体来说，第一个位点 NH酰胺⋯O
C酰胺（形式1I ) 和对称位点 NH amide ⋯N isox ( 1II型)被发现有助于它们的形成。尽管如此，DMSO 的存在导致形成1III型，其中溶剂分子破坏了酰胺-酰胺相互作用。第一个核比1I和1II型更稳定。以化合物N 1 , N 2 -双(5-甲基异恶唑-3-基)草酰胺( 2 )作为对比，通过不存在多晶型物，揭示分子1中的中心碳允许灵活的适应，从而产生三种形式。这些发现表明，溶剂、灵活性以及酰胺-酰胺相互作用的存在/不存在的变化可以调节含酰胺异恶唑化合物之间的竞争。
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