Identical molecular strings woven differently by intermolecular interactions in dimorphs of myo-inositol 1,3,5-orthobenzoate

TitleIdentical molecular strings woven differently by intermolecular interactions in dimorphs of myo-inositol 1,3,5-orthobenzoate
Publication TypeJournal Article
Year of Publication2005
AuthorsBhosekar, GV, Murali, C, Gonnade, RG, Shashidhar, MS, Bhadbhade, MM
JournalCrystal Growth & Design
Volume5
Issue5
Pagination1977-1982
Date PublishedSEP
Type of ArticleArticle
ISSN1528-7483
Abstract

myo-Inositol 1,3,5-orthobenzoate exhibits polymorphic behavior depending upon the solvent and time allowed for crystallization. Long plates (form I, monoclinic P2(1)/n) are produced on crystallization from methanol, while crystallization from ethyl acetate mostly yielded squarish plates (form II, monoclinic P2(1)/c). The latter could also be obtained by achieving rapid nucleation from a supersaturated solution of methanol. Remarkably, the overall conformation of the individual molecules is very similar in both polymorphs, although free rotations were possible for the phenyl ring and for the three O-H groups. O-H center dot center dot center dot O linked one-dimensional isostructural molecular strings in the two forms weave differently by weak intermolecular interactions to produce the dimorphs. Striking difference is seen in the ``zipping'' of molecular layers via phenyl center dot center dot center dot phenyl contacts; thermodynamic crystals of form I utilize a well-recognized ``edge-to-face'' herringbone pattern, making C-H center dot center dot center dot pi interactions, whereas the kinetic crystals of form II show rather uncommon ``edge-to-edge'' organization, which makes short Ph-H center dot center dot center dot H-Ph contacts.

DOI10.1021/cg050272j
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.425
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry