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Interplay of Halogen and Hydrogen Bonding through Co–Crystallization in Pharmacologically Active Dihydropyrimidines: Insights from Crystal Structure and Energy Framework
ChemPlusChem ( IF 3.0 ) Pub Date : 2021-08-18 , DOI: 10.1002/cplu.202100259 Keshab M Bairagi 1 , Kapil S Ingle 1 , Rohit Bhowal 2 , Smital A Mohurle 1 , Avantika Hasija 2 , Osama I Alwassil 3 , Katharigatta N Venugopala 4, 5, 5, 6 , Deepak Chopra 2 , Susanta K Nayak 1
ChemPlusChem ( IF 3.0 ) Pub Date : 2021-08-18 , DOI: 10.1002/cplu.202100259 Keshab M Bairagi 1 , Kapil S Ingle 1 , Rohit Bhowal 2 , Smital A Mohurle 1 , Avantika Hasija 2 , Osama I Alwassil 3 , Katharigatta N Venugopala 4, 5, 5, 6 , Deepak Chopra 2 , Susanta K Nayak 1
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A solvent-assisted grinding method has been used to prepare co-crystals in substituted dihydropyrimidines (DHPM) that constitutes pharmacologically active compounds. These were characterized using FT-IR, PXRD, and single-crystal X-ray diffraction. In order to explore the possibility of formation of halogen (XB) and hydrogen bonding (HB) synthons in the solid state, co-crystallization attempts of differently substituted DHPM molecules, containing nitro, hydoxy, and chloro substituents, with different co-formers, such as 1,4-diiodo tetrafluorobenzene (1,4 DITFB) and 3-nitrobenzoic acid (3 NBA) were performed. The XB co-crystals (C2aXB, C2bXB, and C2cXB) prefer the formation of C−I⋅⋅⋅O/C−I⋅⋅⋅S XB synthon, whereas the HB co-crystal (C2dHB) is stabilized by N−H⋅⋅⋅O H-bond formation. Hirshfeld surface analysis revealed that the percentage contribution of intermolecular interactions for XB co-crystals prefer equal contribution of XB synthon along with HB synthon. Furthermore, the interaction energy was analyzed using energy frameworks, which suggests that their stability, a combination of electrostatics and dispersion, is enhanced through XB/HB in comparison to the parent DHPMs.
中文翻译：
药理活性二氢嘧啶中卤素和氢键的相互作用通过共结晶：晶体结构和能量框架的见解
溶剂辅助研磨法已被用于制备取代二氢嘧啶 (DHPM) 中的共晶体，该共晶体构成药理活性化合物。使用 FT-IR、PXRD 和单晶 X 射线衍射对这些进行了表征。为了探索在固态下形成卤素（XB）和氢键（HB）合成子的可能性，不同取代的DHPM分子（含有硝基、羟基和氯取代基）与不同的共形成体的共结晶尝试，例如1,4-二碘四氟苯（1,4 DITFB）和3-硝基苯甲酸（3 NBA）。XB 共晶（C2aXB、C2bXB 和 C2cXB）更喜欢形成 C−I⋅⋅⋅O/C−I⋅⋅⋅S XB 合成子，而 HB 共晶（C2dHB）由 N−H 稳定⋅⋅⋅O 氢键形成。Hirshfeld 表面分析表明，XB 共晶体的分子间相互作用的百分比贡献更倾向于 XB 合成子与 HB 合成子的相同贡献。此外，使用能量框架分析了相互作用能，这表明与母体 DHPM 相比，通过 XB/HB 增强了它们的稳定性、静电和色散的组合。
更新日期：2021-08-19
中文翻译：
药理活性二氢嘧啶中卤素和氢键的相互作用通过共结晶：晶体结构和能量框架的见解
溶剂辅助研磨法已被用于制备取代二氢嘧啶 (DHPM) 中的共晶体，该共晶体构成药理活性化合物。使用 FT-IR、PXRD 和单晶 X 射线衍射对这些进行了表征。为了探索在固态下形成卤素（XB）和氢键（HB）合成子的可能性，不同取代的DHPM分子（含有硝基、羟基和氯取代基）与不同的共形成体的共结晶尝试，例如1,4-二碘四氟苯（1,4 DITFB）和3-硝基苯甲酸（3 NBA）。XB 共晶（C2aXB、C2bXB 和 C2cXB）更喜欢形成 C−I⋅⋅⋅O/C−I⋅⋅⋅S XB 合成子，而 HB 共晶（C2dHB）由 N−H 稳定⋅⋅⋅O 氢键形成。Hirshfeld 表面分析表明，XB 共晶体的分子间相互作用的百分比贡献更倾向于 XB 合成子与 HB 合成子的相同贡献。此外，使用能量框架分析了相互作用能，这表明与母体 DHPM 相比，通过 XB/HB 增强了它们的稳定性、静电和色散的组合。
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