Concomitant Pseudopolymorphs of 10-Deacetyl Baccatin III

Three new solvates [mono-dimethyl sulfoxide (mono-DMSO), mono-dimethyl acetamide (mono-DMA) and mono-dimethyl formamide (mono-DMF)] of 10-Deacetyl baccatin III, were generated by slow evaporation in DMSO, DMF, and DMSO/DMA (1:1) solvent systems respectively. Two concomitant forms mono-DMSO(a new form) and di-DMSO (a known form) were obtained in the DMSO solvent system. Yet two other concomitant forms mono-DMA (a new form) and di-DMSO (a known form) were obtained in DMSO/DMA (1:1) solvent system. A fourth solvate mono-DMF (a new form) was crystallized in unimolar ratio using DMF as a solvent. These solvates were characterized using powder X-ray diffraction, differential scanning calorimeter, thermogravimetric analysis (TGA), and spectroscopic [13C solid-state nuclear magnetic spectroscopy, solution 1H NMR, and Fourier transform infrared] techniques. The interactions between host and guest molecules were elucitated by single-crystal X-ray diffraction data. In all the cases, guest molecules are connected to the host molecules by O–H···O hydrogen bonds. A remarkable difference in the desolvation onset temperatures of di- and mono-DMSO solvates was observed which was also featured by a corresponding weight loss during TGA analysis.

[1]  E. Weber.  Shape and Symmetry in the Design of New Hosts , 2010 .

[2]  L. Barbour,et al.  Concomitant formation of two different solvates of a hexa-host from a binary mixture of solvents. , 2008, Chemical communications.

[3]  E. Weber,et al.  Selectivity and structure of mixed guest clathrates , 2008 .

[4]  G. Enright,et al.  The ability of lower peptides to form co-crystals: inclusion compounds of Leu-Leu-Leu tripeptide with pyridine and picolines , 2007 .

[5]  Voltaire G. Organo,et al.  Emerging host-guest chemistry of synthetic nanotubes. , 2007, Chemical communications.

[6]  M. Spackman,et al.  Solvent inclusion in the structural voids of form II carbamazepine: single-crystal X-ray diffraction, NMR spectroscopy and Hirshfeld surface analysis , 2007 .

[7]  B. Sarma,et al.  Tetrakis(4-sulfophenyl)methane dodecahydrate. Reversible and selective water inclusion and release in an organic host , 2007 .

[8]  J. Baruah,et al.  Supramolecular and Host−Guest Chemistry of Bis-phenol and Analogues , 2007 .

[9]  G. Day,et al.  Solvent inclusion in form II carbamazepine. , 2007, Chemical communications.

[10]  T. le Roex,et al.  Clathrates with mixed guests. , 2007, Chemical communications.

[11]  Ayesha Jacobs,et al.  Inclusion of volatile guests by a tetrapedal host: structure and kinetics. , 2006, Organic & biomolecular chemistry.

[12]  G. Desiraju,et al.  Solvates of Sildenafil Saccharinate. A New Host Material , 2006 .

[13]  G. Shimizu,et al.  Selective guest inclusion in a non-porous H-bonded host. , 2006, Chemical communications.

[14]  Rolf Hilfiker,et al.  POLYMORPHISM , 1945 .

[15]  A. Nangia.  Organic Host—Guest Structures in the Solid State , 2005 .

[16]  David E. Bugay,et al.  Physical Characterization of Pharmaceutical Solids , 1995, Pharmaceutical Research.

[17]  Gao Qing Lu,et al.  Nanoporous Materials Science and Engineering , 2004 .

[18]  Alexander J. Blake,et al.  OLEX: new software for visualization and analysis of extended crystal structures , 2003 .

[19]  D. Craig,et al.  Comparison of the X-ray structures of concomitant pseudodimorphs formed between a diquinoline host and d-chloroform guest , 2003 .

[20]  O. Sumarna,et al.  Crystal structure, thermal decomposition behavior, and order-disorder transition of the guest component of concomitant pseudodimorphic clathrates between 2,2'-bis(9-hydroxy-9-fluorenyl)biphenyl host and chloroform guest , 2003 .

[21]  M. Maurin,et al.  Solid-state carbon NMR characterization of the polymorphs of roxifiban. , 2002, Journal of pharmaceutical and biomedical analysis.

[22]  J. Atwood,et al.  Storage of Methane and Freon by Interstitial van der Waals Confinement , 2002, Science.

[23]  F. West,et al.  10-Deacetyl baccatin III dimethyl sulfoxide disolvate. , 2001, Acta crystallographica. Section C, Crystal structure communications.

[24]  E. Munson,et al.  Comparison of solid-state 13C NMR spectroscopy and powder X-ray diffraction for analyzing mixtures of polymorphs of neotame , 1999 .

[25]  D. MacNicol,et al.  Symmetry in the Evolution of Host Design , 1997 .

[26]  R. Bishop.  Designing new lattice inclusion hosts , 1997 .

[27]  Jean-Marie Lehn,et al.  Comprehensive Supramolecular Chemistry , 1996 .

[28]  W. L. Jorgensen.  Supramolecular chemistry. , 1993, Proceedings of the National Academy of Sciences of the United States of America.

[29]  E. Weber.  Scissor‐Type Hosts: Molecular Design and Inclusion Behavior , 1992 .

[30]  Gautam R. Desiraju,et al.  Crystal engineering : the design of organic solids , 1989 .

[31]  M. Hagan.  Clathrate inclusion compounds , 1962 .