AbstractTwo impurities of azilsartan (1·EtOH and 2) have been prepared and the structures have been identified by 1H-NMR, IR and single crystal X-ray diffraction. Impurity 1·EtOH (C25H22N4O6, Mr = 474.46) crystallizes in triclinic, space group P-1 with a = 9.0425(15), b = 10.5498(18), c = 12.826(2) Å, α = 76.329(3), β = 79.086(3), γ = 76.763(3)°, V = 1145.4(3) Å3, Z = 2, F(000) = 496, Dc = 1.376 g/cm3, and µ = 0.100 mm− 1. Impurity 2 (C25H20N4O5, Mr = 456.45) is triclinic space group P-1 with a = 9.356(7), b = 9.490(8), c = 13.562(10) Å, α = 72.173(13), β = 73.864(12), γ = 82.628(15)°, V = 1099.9(15) Å3, Z = 2, F(000) = 476, Dc = 1.378 g/cm3, and µ = 0.098 mm−1. 1·EtOH shows a heteronuclear R22(8) dimeric structure through two N–H···O hydrogen bonds constructed by one 1,2,4-oxadiazol and one 2-oxo-benzimidazole groups, and ethanol molecule is attached by O–H···O hydrogen bond. Impurity 2 shows one-dimensional chain structure through two homonuclear R22(8) N–H···O hydrogen bonds constructed by two 1,2,4-oxadiazols and by two 2-oxo-benzimidazoles, respectively. Hirshfeld surface analysis shows that the hydrogen bonds are important to stabilize the conformation.Graphical Abstract Two impurities of azilsartan (1 EtOH and 2) have been prepared and the crystal structures show different molecular configurations and assembly which are predominantly stabilized by the classical hydrogen bonds as well as C–H···N and C–H···O interactions.

中文翻译：

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阿齐沙坦两种杂质的制备、晶体结构和赫什菲尔德表面分析

摘要制备了两种阿齐沙坦杂质（1·EtOH和2），并通过1H-NMR、IR和单晶X射线衍射对其结构进行了鉴定。杂质 1·EtOH (C25H22N4O6, Mr = 474.46) 在三斜晶系中结晶，空间群 P-1，a = 9.0425(15), b = 10.5498(18), c = 12.826(2) Å, α = 39(36) β = 79.086(3), γ = 76.763(3)°, V = 1145.4(3) Å3, Z = 2, F(000) = 496, Dc = 1.376 g/cm3, and µ = 0.100 mm− 1. 杂质2 (C25H20N4O5, Mr = 456.45) 是三斜空间群 P-1，a = 9.356(7), b = 9.490(8), c = 13.562(10) Å, α = 72.173(13), β = 74(73. ), γ = 82.628(15)°, V = 1099.9(15) Å3, Z = 2, F(000) = 476, Dc = 1.378 g/cm3, µ = 0.098 mm−1。1·EtOH通过由一个1,2,4-恶二唑和一个2-氧代-苯并咪唑基团构成的两个N-H…O氢键显示出异核R22(8)二聚体结构，乙醇分子通过O-H···O氢键连接。杂质 2 通过两个同核 R22(8) N–H…O 氢键显示一维链结构，分别由两个 1,2,4-恶二唑和两个 2-氧代-苯并咪唑构成。Hirshfeld 表面分析表明，氢键对于稳定构象很重要。图形摘要 已经制备了两种阿齐沙坦杂质（1 EtOH 和 2），晶体结构显示出不同的分子构型和组装，主要由经典氢键稳定，如以及 C-H···N 和 C-H···O 相互作用。