Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 2 (February 2009)

organic compounds

Acta Cryst. (2009). C65, o54-o57 [ doi:10.1107/S0108270109000225 ]

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

S. Krishnaswamy, R. G. Gonnade, M. M. Bhadbhade and M. S. Shashidhar

Abstract: The title compound, C₁₇H₁₆O₈, 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-HO 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-HO 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-HO 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.

Formula: Two forms of C₁₇H₁₆O₈


	Structure factor file (CIF format) (135.2 kbytes) [ doi:10.1107/S0108270109000225/gd3264Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (140.9 kbytes) [ doi:10.1107/S0108270109000225/gd3264IIsup3.hkl ] Contains datablock II

Notes:

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

Search: From to Advanced search