Nanostructured Materials and Bio-Nano-Interfaces Center, Interdisciplinary Research Institute on Bio-Nano-Sciences, Treboniu Laurian No. 42, 400084 Cluj-Napoca, Romania.
Physics of Nanostructured Systems, National Institute for R&D of Isotopic and Molecular Technologies, Str. Donat 67-103, PO 5 Box 700, 400293 Cluj-Napoca, Romania.
Acta Crystallogr C Struct Chem. 2021 Nov 1;77(Pt 11):698-706. doi: 10.1107/S2053229621010482. Epub 2021 Oct 19.
Four new solvates of the anti-HIV compound etravirine [systematic name: 4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile, CHBrNO] with dimethyl sulfoxide (CHOS, two distinct monosolvates), 1,4-dioxane (CHO, the 0.75-solvate) and N,N-dimethylacetamide (CHNO, the monosolvate), which exhibit conversion to the same anhydrous etravirine phase upon desolvation, and a stable etravirinium oxalate salt {6-amino-5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-2-[(4-cyanophenyl)amino]pyrimidin-1-ium hemioxalate, CHBrNO·0.5CO} were obtained. The crystal structures were solved by single-crystal X-ray diffraction and analyzed by powder X-ray diffraction, and the intermolecular interactions were explored by Hirshfeld surface analysis. Lattice energies were evaluated using the atom-atom force field Coulomb-London-Pauli (AA CLP) approximation, which distributes the total energy as four separate contributions: Coulombic, polarization, dispersion and repulsion. The formation of the solvates and the oxalate salt was further characterized by thermal analysis and IR spectroscopy.
四种新的抗 HIV 化合物依曲韦林[系统命名：4-({6-氨基-5-溴-2-[(4-氰基苯基)氨基]嘧啶-4-基}氧基)-3,5-二甲基苯腈，CHBrNO]与二甲亚砜（CHOS，两种不同的单溶剂化物）、1,4-二氧六环（CHO，0.75-溶剂化物）和 N,N-二甲基乙酰胺（CHNO，单溶剂化物）的溶剂化物，这些溶剂化物在去溶剂化后都转化为相同的无水依曲韦林相，并且获得了稳定的依曲韦林草酸盐{6-氨基-5-溴-4-(4-氰基-2,6-二甲基苯氧基)-2-[(4-氰基苯基)氨基]嘧啶-1-翁草酸，CHBrNO·0.5CO}。通过单晶 X 射线衍射法解决了晶体结构，并通过粉末 X 射线衍射法进行了分析，通过 Hirshfeld 表面分析探讨了分子间相互作用。使用原子-原子力场库仑-伦敦-保尔（AA CLP）近似法评估了晶格能，该方法将总能量分布为四个单独的贡献：库仑、极化、色散和排斥。通过热分析和红外光谱进一步表征了溶剂化物和草酸盐的形成。
