NDLI: Two modes of O-HO hydrogen bonding utilized in dimorphs of racemic 6-O-acryloyl-2-O-benzoyl-myo-inositol 1,3,5-orthoformate

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Two modes of O-HO hydrogen bonding utilized in dimorphs of racemic 6-O-acryloyl-2-O-benzoyl-myo-inositol 1,3,5-orthoformate

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Year: 2009 Volume: 65 Issue: Part 1

Year: 2008 Volume: 64

Two modes of O-HO hydrogen bonding utilized in dimorphs of racemic 6-O-acryloyl-2-O-benzoyl-myo-inositol 1,3,5-orthoformate

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Krishnaswamy, Shobhana Gonnade, Rajesh G. Bhadbhade, Mohan M. Shashidhar, Mysore S.
Description	Country affiliation: India Author Affiliation: Krishnaswamy S ( Centre for Materials Characterization, National Chemical Laboratory, Pune 411 008, India. s.krishnaswamy@ncl.res.in)
Abstract	The title compound, C $_{17}H$ $_{16}O$ $_{8},$ yields conformational dimorphs [forms (I) and (II)] at room temperature, separately or concomitantly, depending on the solvent of crystallization. The yield of crystals of form (I) is always much more than that of crystals of form (II). The molecule has one donor -OH group that can make intermolecular O-H O hydrogen bonds with one of the two acceptor C=O groups, as well as with the hydroxyl O atom; interestingly, each of the options is utilized separately in the dimorphs. The crystal structure of form (I) contains one molecule in the asymmetric unit and is organized as a planar sheet of centrosymmetric dimers via O-H O hydrogen bonds involving the OH group and the carbonyl O atom of the acryloyl group. In the crystal structure of form (II), which contains two independent molecules in the asymmetric unit, two different O-H O hydrogen bonds, viz. hydroxyl-hydroxyl and hydroxyl-carbonyl (benzoyl), connect the molecules in a layered arrangement. Another notable feature is the transformation of form (II) to form (I) via melt crystallization upon heating to 411 K. The higher yield of form (I) during crystallization and the thermal transition of form (II) to form (I) suggest that the association in form (I) is more highly favoured than that in form (II), which is valuable in understanding the priorities of molecular aggregation during nucleation of various polymorphs.
File Format	HTM / HTML
e-ISSN	20532296
Journal	Acta Crystallographica Section C Crystal Structure Communications
Issue Number	Pt 2
Volume Number	65
Language	English
Publisher	IUCr/Wiley
Publisher Date	2009-02-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Analytical Chemistry Discipline Crystallography Acrylates Chemistry Inositol Analogs & Derivatives Crystallization Dimerization Hydrogen Hydrogen Bonding Hydroxyl Radical Stereoisomerism X-ray Diffraction Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article

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