Journal of Chemical Crystallography

, Volume 42, Issue 8, pp 790–793 | Cite as

High Resolution Structure of Half-Cage Isodrin Propionate, a Molecule Suitable for Studying Nuclear Overhauser Effects in the Organic Laboratory

  • Eric W. Reinheimer
  • Minseok Jang
  • Samuel J. Sobelman
  • Andrew H. Stewart
  • Katherine A. Kantardjieff
  • Adam R. Johnson
Original Paper


The nuclear overhauser effect (NOE) has emerged as a useful tool for studying the structural features of a molecule via NMR spectroscopy. Herein we describe the high quality solid state structure of half-cage isodrin propionate, whose facile synthesis makes it a suitable molecule to measure and study the NOE in both undergraduate and graduate organic laboratories. Half-cage isodrin propionate crystallizes in the monoclinic space group P2 1 /n with unit cell parameters a = 12.0064(11) Å, b = 12.7511(12) Å, c = 22.540(2) Å and β = 105.27(3)°. The asymmetric unit contains two Half-cage isodrin propionate molecules with atoms on general positions. Critical to the observation of NOE in the title molecule is an ultrashort interatomic contact involving two isolated, neighboring hydrogen atoms found in each half-cage molecule of the asymmetric unit. The interatomic distances were measured at 1.737(2) Å within the first half-cage molecule and 1.725(2) Å within the second. Secondary to the observation of these short interatomic separations, the solid state structure of half-cage isodrin propionate, with its Z’ > 1, represents a situation where each molecule’s inherent differences might be analyzed and discussed.

Graphical Abstract


NMR Nuclear Overhauser 



This project was supported by the Department of Chemistry at Harvey Mudd College, the Department of Chemistry and Biochemistry at California State University, Fullerton, and by the National Science Foundation (RUI-CHE-0615724) as part of a chemical crystallography course taught jointly between the two institutions. The authors would like to thank Daniel Hickstein and Professor Daniel O’Leary (Pomona College) for their synthesis and crystallization of the title compound.


  1. 1.
    Anet FAL, Bourn AJR (1965) J Am Chem Soc 87:5250CrossRefGoogle Scholar
  2. 2.
    Ermer O, Mason SA, Anet FAL, Miura SS (1985) J Am Chem Soc 107:2330CrossRefGoogle Scholar
  3. 3.
    Woods MC, Miura I, Nakadaira Y, Terahara A, Maruyama M, Nakanishi K (1967) Tetrahedron Lett 4:321CrossRefGoogle Scholar
  4. 4.
    Woods MC, Chiang HC, Nakadaira Y, Nakanishi K (1968) J Am Chem Soc 90:522CrossRefGoogle Scholar
  5. 5.
    Balaram P, Bohner-By AA, Dadok J (1972) J Am Chem Soc 94:4015CrossRefGoogle Scholar
  6. 6.
    Kumar A, Ernst RR, Wuthrich K (1980) Biochem Biophys Res Commun 95:1CrossRefGoogle Scholar
  7. 7.
    Chen AE, O’Leary DJ, Miura SS, Anet FAL (2000) Concep Magn Reson 12:1CrossRefGoogle Scholar
  8. 8.
    SMART, Software for the CCD Detector System, version 5.050 (NT); Bruker Analytical X-ray Systems: Madison, WI, 1998Google Scholar
  9. 9.
    SAINT (1998), Software for the CCD Detector System, version 5.01 (NT); Bruker Analytical X-ray Systems. Madison, WIGoogle Scholar
  10. 10.
    Blessing RH (1995) SADABS, Program for absorption corrections using Siemens CCD based on the method of Robert Blessing. Acta Cryst. A51: 33Google Scholar
  11. 11.
    Sheldrick GM (1996) XPREP, Program for space group determination. University of Göttingen, GermanyGoogle Scholar
  12. 12.
    Speck AL (2001) PLATON, A multipurpose crystallographic tool. Utrecht University, The NetherlandsGoogle Scholar
  13. 13.
    Sheldrick GM (1997) SHELXS-97, Program for crystal structure determination. University of Göttingen, GermanyGoogle Scholar
  14. 14.
    Sheldrick GM (1997) SHELXL-97, Program for the refinement of crystal structure. University of Göttingen, GermanyGoogle Scholar
  15. 15.
    Barbour LJ (2001) J Supramol Chem 1:189CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Eric W. Reinheimer
    • 1
    • 3
  • Minseok Jang
    • 2
  • Samuel J. Sobelman
    • 2
  • Andrew H. Stewart
    • 2
  • Katherine A. Kantardjieff
    • 1
    • 3
  • Adam R. Johnson
    • 2
  1. 1.Department of Chemistry and the W.M. Keck Foundation Center for Molecular StructureCalifornia State Polytechnic UniversityPomonaUSA
  2. 2.Department of ChemistryHarvey Mudd CollegeClaremontUSA
  3. 3.Department of Chemistry and Biochemistry and the W.M. Keck Foundation Center for Molecular StructureCalifornia State University, San MarcosSan MarcosUSA

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