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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

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Abstract

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.

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Acknowledgments

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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  1. Department of Chemistry and Biochemistry, University of Oklahoma, 101 Stevenson Parkway, Norman, OK, 73071-5251, USA

    Tam Nguyen, Christopher M. Buckley, Trevor K. Ellis, Gary L. N. Smith, Douglas R. Powell & Richard W. Taylor

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  1. Tam Nguyen
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  2. Christopher M. Buckley
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Correspondence to Richard W. Taylor.

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Nguyen, T., Buckley, C.M., Ellis, T.K. et al. 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. J Chem Crystallogr 42, 573–577 (2012). https://doi.org/10.1007/s10870-012-0281-1

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