Skip to main content
SpringerLink
Log in

Crystal Polymorphism of Methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-d-glucopyranouronate

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

The polymorphism of the glycoside donor methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-d-glucopyranouronate (1) has been investigated. Two polymorphic forms (labelled Forms I and II) have been elucidated and fully characterised by DSC, PXRD and single crystal analysis, both crystallizing in the space group P21. Form I was obtained by crystallization from a wide range of solvents, while Form II was obtained only from ethyl acetate or isopropanol on certain occasions. Unit cell dimensions for Form I are a 14.0292(12), b 8.9641(8), c 16.8580(14) Å, β 94.285(2)°, and for Form II a 11.266(3), b 6.8889(17), c 13.921(4) Å, β 101.161(6)°. Z’ is 2 for Form I and 1 for Form II. Form I displays two moderate intermolecular hydrogen bonds in the unit cell whereas Form II shows no moderate hydrogen-bonding motifs. All three molecules in the two polymorphs differ significantly in their conformations, especially with respect to the methyl carboxylate and trichloroacetimidoyl groups.

Graphical Abstract

Structures of two polymorphs of methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-d-glucopyranouronate were determined.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Bernstein J (2002) Polymorphism in Molecular Crystals. Oxford Science Publications, Oxford

    Google Scholar 

  2. Braga D, Grepioni F, Maini L (2010) Chem Commun 46:6232

    Article  CAS  Google Scholar 

  3. Bernstein J, Hagler AT (1978) J Am Chem Soc 100:673

    Article  CAS  Google Scholar 

  4. Mukuta T, Lee AY, Kawakami T, Myerson AS (2005) Cryst Growth Des 5:1429

    Article  CAS  Google Scholar 

  5. Schmidt RR (1986) Angew Chem Int Ed Engl 25:212

    Article  Google Scholar 

  6. Fischer B, Nudelman A, Ruse M, Herzig J, Gottlieb HE (1984) J Org Chem 49:4988

    Article  CAS  Google Scholar 

  7. Stachulski AV, Jenkins G (1998) Nat Prod Rep 15:173

    Article  CAS  Google Scholar 

  8. Brown RT, Carter NE, Mayalarp SP, Scheinmann F (2000) Tetrahedron 56:7591

    Article  CAS  Google Scholar 

  9. Kuszmann J, Medgyes G, Boros S (2004) Carbohydr Res 339:1569

    Article  CAS  Google Scholar 

  10. Hayes JA, Eccles KS, Lawrence SE, Moynihan HA (2012) Carbohydr Res 349:108

    Article  CAS  Google Scholar 

  11. Bruker AXS (2009) APEX2 v2009.3–0. Madison, WI

    Google Scholar 

  12. Sheldrick GM (2008) Acta Crystallogr A 64:112

    Article  Google Scholar 

  13. Macrae CF, Bruno IJ, Chrisholm JA, Edgington PR, McCabe P, Pidcock E, Rodriguez-Monge L, Taylor R, van de Streek J, Wood PA (2008) J Appl Crystallogr 41:466

    Article  CAS  Google Scholar 

  14. Spek AL (2009) Acta Cryst D65:148

    CAS  Google Scholar 

  15. Cremer D, Pople JA (1975) J Am Chem Soc 97:1354

    Article  CAS  Google Scholar 

  16. Flack HD (1983) Acta Crystallogr A39:876

    CAS  Google Scholar 

  17. Cai C, Wei G, Du Y (2010) Acta Cryst E66:o949

    CAS  Google Scholar 

  18. Baddeley TC, Howie RA, Skakle JMS, Wardell JL (2005) Acta Cryst C61:o711

    CAS  Google Scholar 

Download references

Acknowledgments

This publication has emanated from research conducted with the financial support of Science Foundation Ireland under Grant Numbers 07/SRC/B1158, 08/RFP/MTR1664 and 05/PICA/B802/EC07.

Author information

Authors and Affiliations

  1. Analytical and Biological Chemistry Research Facility, Department of Chemistry, University College Cork, College Road, Cork, Ireland

    John A. Hayes, Kevin S. Eccles, Curtis J. Elcoate, Carla A. Daly, Simon E. Lawrence & Humphrey A. Moynihan

Authors
  1. John A. Hayes
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kevin S. Eccles
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Curtis J. Elcoate
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Carla A. Daly
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Simon E. Lawrence
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Humphrey A. Moynihan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Humphrey A. Moynihan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hayes, J.A., Eccles, K.S., Elcoate, C.J. et al. Crystal Polymorphism of Methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-d-glucopyranouronate. J Chem Crystallogr 43, 138–143 (2013). https://doi.org/10.1007/s10870-013-0397-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-013-0397-y

Keywords

Search

Navigation