Jump to main content
Jump to site search

Issue 6, 2009
Previous Article Next Article

Isostructural molecular strings linked via conserved dipolar (ether) O⋯C[double bond, length as m-dash]O short contacts in conformational polymorphs of racemic 2,4-di-O-acetyl-6-O-tosyl-myo-inositol 1,3,5-orthoesters

Author affiliations

Abstract

Conformational dimorphs of racemic 2,4-di-O-acetyl-6-O-tosyl-myo-inositol 1,3,5-orthoformate and its orthoacetate analogue were characterized using single crystal X-ray diffraction, thermal analysis and hot-stage microscopy techniques. In these polymorphs, the tosyl group adopted different conformations due to the rotation about the O–S bond. A significant variation in the torsion angle for the tosyl group (∼56°) was observed for Form II crystal of the orthoformate derivative, which exhibited an intramolecular dipolar S[double bond, length as m-dash]O⋯C[double bond, length as m-dash]O (sulfonylcarbonyl) short contact. An interesting feature in all conformational polymorphs is the formation of an isostructural string (despite the differences in the orientation of the tosyl group) linked via dipolar (ether) O⋯C[double bond, length as m-dash]O contacts, which is further stitched by other weak interactions to form different layers in their crystal lattice.

Graphical abstract: Isostructural molecular strings linked via conserved dipolar (ether) O⋯C [[double bond, length as m-dash]] O short contacts in conformational polymorphs of racemic 2,4-di-O-acetyl-6-O-tosyl-myo-inositol 1,3,5-orthoesters

Back to tab navigation

Supplementary files

Article information


Submitted
27 Oct 2008
Accepted
16 Dec 2008
First published
28 Jan 2009

CrystEngComm, 2009,11, 1022-1029
Article type
Paper

Isostructural molecular strings linked via conserved dipolar (ether) O⋯C[double bond, length as m-dash]O short contacts in conformational polymorphs of racemic 2,4-di-O-acetyl-6-O-tosyl-myo-inositol 1,3,5-orthoesters

K. Manoj, R. G. Gonnade, M. M. Bhadbhade and M. S. Shashidhar, CrystEngComm, 2009, 11, 1022
DOI: 10.1039/B818888B

Social activity

Search articles by author

Spotlight

Advertisements