Issue 6, 2009
From the journal:

CrystEngComm

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,ab   Rajesh G. Gonnade,a   Mohan M. Bhadbhade*a  and  Mysore S. Shashidhar*b  

* Corresponding authors

a Center for Materials Characterization, National Chemical Laboratory, Pune, India
E-mail: m.bhadbhade@unsw.edu.au
Fax: +91-20-25902642
Tel: +91-20-25902290

b Organic Chemistry Division, National Chemical Laboratory, Pune, India
E-mail: ms.shashidhar@ncl.res.in
Fax: +91-20-25902624
Tel: +91-20-25902055

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 (sulfonyl–carbonyl) 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

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Article information

DOI
https://doi.org/10.1039/B818888B
Article type
Paper
Submitted
27 Oct 2008
Accepted
16 Dec 2008
First published
28 Jan 2009

CrystEngComm, 2009,11, 1022-1029

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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

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