The (-)-gossypol-2,4-pentanedione (1:2) inclusion complex
The (-)-gossypol-2,4-pentanedione (1:2) inclusion complex
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DOI：
10.1023/b:jocc.0000042026.45650.c5
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发表时间：
2004-08-01
影响因子：
0.8
通讯作者：
Stevens, ED
中科院分区：
文献类型：
--
作者：
Dowd, MK;Stevens, ED
（-）-棉酚和2，4-戊二酮以1：2的摩尔比形成包合络合物。该化合物的晶体结构属于四元P4（1）2（1）2空间群，晶胞尺寸为a = B = 10.9966（7）埃，c = 60.213（4）埃。两种溶剂分子都是烯醇形式，并占据结构内的两个不同的空腔。第一个空腔形成在成对的棉酚萘环之间，并包含一对与溶剂相关的溶剂分子，每个溶剂分子接受来自周围棉酚分子之一的氢键。这四个分子一起形成一个楔形组件，在整个细胞中重复。组件堆叠以形成列，并且相邻列平行对齐以形成层。相邻的层以90度角取向，这解释了空间群的四重对称性。第二溶剂腔位于在层之间形成的隔离袋中。这些溶剂分子也接受来自周围棉酚分子的氢键。虽然已经报道了许多棉酚溶剂化物，但这种结构在许多特征上是不寻常的。这是首次报道的手性非团聚棉酚溶剂化物。它也是唯一已知的手性棉酚包合物，当从其母液中除去时不会损失可观量的溶剂。
(-)-Gossypol and 2,4-pentanedione form an inclusion complex in a one-to-two molar ratio. The compound crystallizes in the tetragonal P4(1)2(1)2 space group and has unit cell dimensions of a = b = 10.9966(7) Angstrom and c = 60.213(4) Angstrom. Both solvent molecules are in the enol form and occupy two distinct cavities within the structure. The first cavity is formed between pairs of gossypol naphthalene rings and contains a pair of symmetry-related solvent molecules that each accept a hydrogen bond from one of the surrounding gossypol molecules. The four molecules together form a wedge-shaped assembly that is repeated throughout the cell. The assemblies stack to form columns, and adjacent columns are aligned parallel to form layers. Neighboring layers are oriented at 90degrees angles, which accounts for the fourfold symmetry of the space group. The second solvent cavity is located in isolated pockets that form between the layers. These solvent molecules also accept hydrogen bonds from the surrounding gossypol molecules. Although many gossypol solvates have been reported, this structure is unusual in a number of features. It is the first report of a chiral non-conglomerate gossypol solvate. It is also the only known chiral gossypol inclusion complex to not lose appreciable amounts of solvent when removed from its mother liquor.