Journal of Chemical Crystallography

, Volume 42, Issue 6, pp 573–577 | Cite as

Synthesis, NMR Studies and Crystal Structure of Cryptand 4,7,10,16,21-Pentaoxa-1,13-diazabicyclo[11.5.5]tricosane, [H(3.1.1)·(H2O)3]Cl

  • Tam Nguyen
  • Christopher M. Buckley
  • Trevor K. Ellis
  • Gary L. N. Smith
  • Douglas R. Powell
  • Richard W. Taylor
Original Paper


The cryptand 4,7,10,16,21-pentaoxa-1,13-diazabicyclo[11.5.5]tricosane (3.1.1, I) has been synthesized, the crystal structure of the triaquo-hydrochloride salt has been determined by single crystal X-ray crystallography and the 1H- and 13C-NMR chemical shifts have been assigned for the protonated ligand. [(C16H33N2O5)·(H2O)3]Cl, (I), is triclinic with space group \(P\bar{1}\) and cell constants: a = 9.957(3) Å, b = 10.557(5) Å, c = 11.324(3) Å, α = 95.917(8)°, β = 105.574(8)°, γ = 107.506(9)°, V = 1071.4(3) Å3 and Z = 2. In the solid state the cryptand is monoprotonated and holds a water molecule near the central cavity using the hydrogen bonds N13–H13 to O1S, O1S–H1S2 to N1 and O1S–H1S1 to ether oxygen atom O7. Pairs of cryptand molecules are linked by a hydrogen bond network, (O21···H2S2–O2S–H2S1···Cl1)2(μ-H3S1–O3S–H3S2)2, that interacts with an ether oxygen (O21, O21A) in each ligand molecule.

Graphical Abstract

The synthesis, NMR characterization, and X-ray structure of cryptand 3.1.1 are described.


Cryptand Crystal structure NMR spectra Hydrogen bonds Hydrate 



This study was supported by the Oklahoma Center for the Advancement of Science and Technology (grant HR06-113). The authors also thank the National Science Foundation (CHE-0130835) and the University of Oklahoma for funds to acquire the diffractometer and computers used in this study.


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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Tam Nguyen
    • 1
  • Christopher M. Buckley
    • 1
  • Trevor K. Ellis
    • 1
  • Gary L. N. Smith
    • 1
  • Douglas R. Powell
    • 1
  • Richard W. Taylor
    • 1
  1. 1.Department of Chemistry and BiochemistryUniversity of OklahomaNormanUSA

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