The synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety have attracted interest as these compounds are important pharmacophores. The crystal structures of three closely related N‐aryl‐2,5‐dimethoxybenzenesulfonamides, namely N‐(2,3‐dichlorophenyl)‐2,5‐dimethoxybenzenesulfonamide, C₁₄H₁₃Cl₂NO₄S, (I), N‐(2,4‐dichlorophenyl)‐2,5‐dimethoxybenzenesulfonamide, C₁₄H₁₃Cl₂NO₄S, (II), and N‐(2,4‐dimethylphenyl)‐2,5‐dimethoxybenzenesulfonamide, C₁₆H₁₉NO₄S, (III), are described. The asymmetric unit of (I) consists of two symmetry‐independent molecules, while those of (II) and (III) contain one molecule each. The molecular conformations are stabilized by different intramolecular interactions, viz. C—H…O interactions in (I), N—H…Cl and C—H…O interactions in (II), and C—H…O interactions in (III). The crystals of the three compounds display different supramolecular architectures built by various weak intermolecular interactions of the types C—H…O, C—H…Cl, C—H…π(aryl), π(aryl)–π(aryl) and Cl…Cl. A detailed Hirshfeld surface analysis of these compounds has also been conducted in order to understand the relationship between the crystal structures. The d_norm and shape‐index surfaces of (I)–(III) support the presence of various intermolecular interactions in the three structures. Analysis of the fingerprint plots reveals that the greatest contribution to the Hirshfeld surfaces is from H…H contacts, followed by H…O/O…H contacts. In addition, comparisons are made with the structures of some related compounds. Putative N—H…O hydrogen bonds are observed in 29 of the 30 reported structures, wherein the N—H…O hydrogen bonds form either C(4) chain motifs or R₂²(8) rings. Further comparison reveals that the characteristics of the N—H…O hydrogen‐bond motifs, the presence of other interactions and the resultant supramolecular architecture is largely decided by the position of the substituents on the benzenesulfonyl ring, with the nature and position of the substituents on the aniline ring exerting little effect. On the other hand, the crystal structures of (I)–(III) display several weak interactions other than the common N—H…O hydrogen bonds, resulting in supramolecular architectures varying from one‐ to three‐dimensional depending on the nature and position of the substituents on the aniline ring.

中文翻译：

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三种N-芳基-2,5-二甲氧基苯磺酰胺的晶体中不同的弱相互作用介导的不同的超分子结构。

含有磺酰胺部分的分子的合成和药理活性评估引起了人们的兴趣，因为这些化合物是重要的药效团。3的晶体结构密切相关ñ -芳基-2,5- dimethoxybenzenesulfonamides，即ñ - （2,3-二氯苯基）-2,5- dimethoxybenzenesulfonamide，C ₁₄ ħ ₁₃氯₂ NO ₄ S，（I），ñ - （2,4-二氯苯基）-2-，5-二甲氧基苯磺酰胺，C ₁₄ H ₁₃ Cl ₂ NO ₄ S，（II）和N-（2,4-二甲基苯基）-2,5-二甲氧基苯磺酰胺，C ₁₆ H_描述了19 NO ₄ S，（III）。（I）的不对称单元由两个不对称的分子组成，而（II）和（III）的不对称单元各包含一个分子。分子构象通过不同的分子内相互作用而稳定。（I）中的C–H…O相互作用，（II）中的N–H…Cl和C–H…O相互作用，以及（III）中的C–H…O相互作用。这三种化合物的晶体显示出不同的超分子结构，这些结构是由C–H…O，CH–H…Cl，CH–H…π（芳基），π（芳基）–π（芳基）和Cl…Cl 为了理解晶体结构之间的关系，还对这些化合物进行了详细的Hirshfeld表面分析。该d_规范（I）–（III）的形状和指数表面支持三种结构中各种分子间相互作用的存在。对指纹图的分析表明，对Hirshfeld表面的最大贡献是来自H…H接触，其次是H…O / O ... H接触。此外，还对一些相关化合物的结构进行了比较。在30个报告的结构中的29个中观察到推定的N-H ... O氢键，其中N-H ... O氢键形成C（4）链基序或R ₂ ²（8）响。进一步的比较表明，N-H…O氢键基序的特征，其他相互作用的存在以及所得的超分子结构在很大程度上取决于苯磺酰基环上取代基的位置以及取代基的性质和位置对苯胺环的作用很小。另一方面，（I）–（III）的晶体结构除了常见的NH–O氢键外还表现出一些弱相互作用，从而导致超分子结构从一维到三维不等，具体取决于性质和位置苯胺环上的取代基的数目。