Hierarchical Prediction Process of Cholic Acid Crystal Structures Based on Characteristic Helical Assemblies

REFERENCES

• Gavezzotti , A. & Desiraju , G. R. ( 1988 ). A ssystematic analysis of packing energies and other packing parameters for fused-ring aromatic hydrocarbons . Acta Crystallogr. , B44 , 427 – 433 .
   Web of Science ®Google Scholar
• Desiraju , G. R. & Gavezzotti , A. ( 1989 ). From molecular to crystal structure; polynuclear aromatic hydrocarbons . J. Chem. Soc. Chem. Commun. , 621 – 623 . [CROSSREF]
   Google Scholar
• Aoyama , Y. , Endo , K. , Anzai , T. , Yamaguchi , Y. , Sawaki , T. , Kobayashi , K. , Kanehisa , N. , Hashimoto , H. , Kai , Y. , & Masuda , H. (1996). Crystal Engineering of Stacked Aromatic Columns. Three-Dimensional Control of the Alignment of Orthogonal Aromatic Triads and Guest Quinones via Self-Assembly of Hydrogen-Bonded Networks. J. Am. Chem. Soc. , 118, 5562–5571. [CROSSREF]
   Web of Science ®Google Scholar
• Evans , C. C. , Sukarto , L. , & Ward , M. D. ( 1999 ). Sterically controlled architectural reversion in hydrogen-bonded crystalline clathrates . J. Am. Chem. Soc. , 121 , 320 – 325 . [CROSSREF]
   Google Scholar
• Bishop , R. ( 1996 ). Helical host lattices formed by alicyclic diols . In: Comprehensive Supramolecular Chemistry , MacNicol , D. D. , Toda , F. , & Bishop , R. (Eds.), New York : Pergamon , vol. 6 , 85 – 115 .
   Google Scholar
• Miyata , M. , Shibakami , M. , Goonewardena , W. , & Takemoto , K. ( 1987 ). Inclusion compounds of cholic acid with a variety of organic substances . Chem. Lett. , 605 – 608 .
   Google Scholar
• Miyata , M. , Sada , K. , & Yoswathananont , N. ( 2004 ). Deoxycholic, Cholic, and Apocholic acids , in: Encyclopedia of Supramolecular Chemistry , Atwood , J. L. & Steed , J. W. (Eds.), New York : Marcel Dekker .
   Google Scholar
• Johnson , P. L. & Schaefer , J. P. ( 1972 ). Crystal and molecular structure of an addition compound of cholic acid and ethanol . Acta Crystallogr. , 28 , 3083 – 3089 .
   Web of Science ®Google Scholar
• Miki , K. , Masui , A. , Kasai , N. , Miyata , M. , Shibakami , M. , & Takemoto , K. ( 1988 ). New channel type inclusion compound of steroidal bile acid. Structure of 1:1 complex between cholic acid and acetophenone . J. Am. Chem. Soc. , 110 , 6594 – 6596 . [CROSSREF]
   Web of Science ®Google Scholar
• Miyata , M. , Shibakami , M. , Chirachanchai , S. , Takemoto , K. , Kasai , N. , & Miki , K. ( 1990 ). Guest-responsive structural changes in cholic acid intercalation crystals . Nature , 343 , 446 – 447 . [CROSSREF]
   Web of Science ®Google Scholar
• Shibakami , M. , Tamura , M. , & Sekiya , A. ( 1994 ). Crystal structures of cholic acid-aniline and -3-fluoroaniline inclusion compound; fluorine atom effect on channel and hydrogen bonding pattern . J. Chem. Soc. Chem. Commun. , 429 – 430 . [CROSSREF]
   Google Scholar
• Nakano , K. , Sada , K. , & Miyata , M. ( 1995 ). Guest-participating reversion of molecular arrangements in asymmetric multibilayers of cholic acid inclusion crystals . J. Chem. Soc. Chem. Commun. , 429 – 430 .
   Google Scholar
• Yoswathananont , N. , Chirachanchai , S. , Tashiro , K. , Nakano , K. , Sada , K. , & Miyata , M. ( 2001 ). A novel host framework of cholic acid inclusion crystals by slide and flip of the layers . Cryst. Eng. Comm. , 19 , 1 – 4 .
   Google Scholar
• Nakano , K. , Sada , K. , Kurozumi , Y. , & Miyata , M. ( 2001 ). Importance of packing coefficients of host cavities in the isomerization of open host frameworks: guest-size-dependent isomerization in cholic acid inclusion crystals with monosubstituted benzenes . Chem. Eur. J. , 7 , 209 – 220 . [CROSSREF]
   Google Scholar
• Nakano , K. , Mochizuki , E. , Yasui , N. , Morioka , K. , Yamauchi Yukinori , Kanehisa , N. , Kai , Y. , Yoswathananont , N. , Tohnai , N. , Sada , K. , & Miyata , M. ( 2003 ). Mechanism of selective and unselective enclathration by a host compound possessing open, flexible host frameworks . Eur. J. Org. Chem. , 13 , 2428 – 2436 . [CROSSREF]
   Google Scholar
• Miyata , M. & Sada , K. ( 1996 ). Deoxycholic acid and related hosts . In: Comprehensive Supramolecular Chemistry , MacNicol , D. D. , Toda , F. , Bishop , R. , (Eds.), New York : Pergamon , vol. 6 , 147 – 176 .
   Google Scholar
• Hishikawa , Y. , Watanabe , R. , Sada , K. , & Miyata , M. ( 1998 ). Molecular arrangements in chiral sheets of n-alkylcholamides bilayered crystals . Chirality , 10 , 600 – 618 . [CROSSREF]
   Google Scholar
• Kitaigorodskii , A. ( 1973 ). Molecular crystals and molecules , New York : Academic Press .
   Google Scholar