Identical Molecular Strings Woven Differently by Intermolecular Interactions in Dimorphs of <i>m</i><i>yo</i>-Inositol 1,3,5-Orthobenzoate
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myo-Inositol 1,3,5-orthobenzoate exhibits polymorphic behavior depending upon the solvent and time allowed for crystallization. Long plates (form I, monoclinic P21/n) are produced on crystallization from methanol, while crystallization from ethyl acetate mostly yielded squarish plates (form II, monoclinic P21/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···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···phenyl contacts; thermodynamic crystals of form I utilize a well-recognized “edge-to-face” herringbone pattern, making C−H···π interactions, whereas the kinetic crystals of form II show rather uncommon “edge-to-edge” organization, which makes short Ph−H···H−Ph contacts.



