Conglomerate formation and crystal structure of 4-phenyl-1,3-thiazolidin-2-one
- 作者：Kitoh ; Soh-ichi ; Kubota ; Akihito ; Kunimoto ; Ko-Ki ; Kuwae ; Akio ; Hanai ; Kazuhiko
- 关键词：Crystal structure ; 4-Phenyl-1 ; 3-thiazolidin-2-one ; Spontaneous optical resolution ; Conglomerate ; Racemic compound
- 刊名：Journal of Molecular Structure
- 出版年：2005
- 期刊代码：62_00222860
- 类别：ch
- 出版时间：March 4, 2005
- 卷：737
- 期：2-3
- 页码：277-282
- 文件大小：220 K
摘要
Racemic 4-phenyl-1,3-thiazolidin-2-one (4-PTO) crystallizes in the form of conglomerate. The conglomerate formation has been confirmed by analyzing Weissenberg X-ray photographs and IR, Raman spectra of the racemate and the enantiopure 4-PTO crystals. The crystal structure of 4-PTO has been determined by X-ray diffraction, and the structural features are compared with those of other 4-phenyl-1,3-oxazolidin-2-one derivatives in order to understand the structural factors leading to the conglomerate formation. In 4-PTO crystals, the N-H
O intermolecular hydrogen bonds are formed between the amide groups of neighboring molecules in a homochiral zigzag chain. In addition, the intermolecular SO close contacts are observed between the thioether and the carbonyl groups in the same chain unit. Moreover, the phenyl groups of homochiral 4-PTO molecules of different chain units take the T-shaped stacking orientation to each other due to the aromatic CH/π interaction. These structural factors altogether reinforce the homochiral supramolecular assembly of chain structural units in the 4-PTO crystal.
O intermolecular hydrogen bonds are formed between the amide groups of neighboring molecules in a homochiral zigzag chain. In addition, the intermolecular SO close contacts are observed between the thioether and the carbonyl groups in the same chain unit. Moreover, the phenyl groups of homochiral 4-PTO molecules of different chain units take the T-shaped stacking orientation to each other due to the aromatic CH/π interaction. These structural factors altogether reinforce the homochiral supramolecular assembly of chain structural units in the 4-PTO crystal.