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Polymorphism of aromatic sulfonamides with fluorine groups

机译：含氟芳香族磺酰胺的多态性

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N-(2-Phenoxyphenyl)benzenesulfonamide (1) and fluorine-substituted N-(2-phenoxyphenyl)benzene sulfonamides (2-5) were designed to examine the effect of a fluorine group in the polymorphism of aromatic sulfonamides. Single-crystal X-ray analysis revealed that those with a fluorine (2-5) afforded polymorphs or pseudopolymorphs while the sulfonamide without fluorine (1) did not. From the differential scanning calorimetry measurements, stable (2a-5a) and metastable (2b-5b) crystalline forms were identified. The sulfonamide 1 formed a dimer through hydrogen bonds (H-bonds), which were aligned into two-dimensional (2D) layers via π/π and CH/π interactions. In 2b, 3b, and 4a, the sulfonamide constructed a dimer through H-bonds, which formed 2D layers via CH/F interactions. The sulfonamides 4 formed a one-dimensional (1D) straight chain via H-bonds, which were arranged into 2D layers via CH/F, CH/O, and CH/π interactions in 4b. The sulfonamide 5 either formed a dimer through H-bonds, which formed 2D layers via CH/O and π/π interactions in 5a, or formed a 1D straight chain via CH/O and π/π interactions, which were arranged into 2D layers via F/F and CH/F interactions in 5b. In the pseudopolymorph 5c, the sulfonamide 5 formed a 1D zigzag chain via CH/F interactions and was assembled into 2D layers via π/π interactions.
机译：设计N-（2-苯氧基苯基）苯磺酰胺（1）和氟取代的N-（2-苯氧基苯基）苯磺酰胺（2-5），以研究氟基团对芳族磺酰胺多态性的影响。 X射线单晶分析表明，具有氟（2-5）的那些提供多晶型物或假多晶型物，而不含氟的磺酰胺（1）则没有。从差示扫描量热法测量中，鉴定出稳定的（2a-5a）和亚稳的（2b-5b）晶体形式。磺酰胺1通过氢键（H键）形成二聚体，氢键通过π/π和CH /π相互作用排列成二维（2D）层。在2b，3b和4a中，磺酰胺通过H键构造了一个二聚体，它通过CH / F相互作用形成了2D层。磺酰胺4通过H键形成一维（1D）直链，并通过CH / F，CH / O和CH /π相互作用在4b中排列成2D层。磺酰胺5通过H键形成二聚体，通过5a中的CH / O和π/π相互作用形成2D层，或通过CH / O和π/π相互作用形成1D直链，排列成2D层通过5b中的F / F和CH / F交互。在假多晶型物5c中，磺酰胺5通过CH / F相互作用形成1D之字形链，并通过π/π相互作用组装成2D层。

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