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Crystal and Molecular Structures of Benzyl-(2-chloro-6-methylpyrimidin-4-yl)amine and Benzyl-(4-chloro-6-methylpyrimidin-2-yl)amine: Confirmation of Computationally Predicted Restricted Rotation

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Abstract

Crystal structures for the isomeric compounds benzyl-(2-chloro-6-methylpyrimidin-4-yl)amine (1), as its hemi-hydrate, and benzyl-(4-chloro-6-methylpyrimidin-2-yl)amine (2) have been determined. Conformational differences lead to multiple molecules, i.e. two and three, in their respective structures. Layers feature in each of the crystal structures and are stabilized by substantial hydrogen-bonding interactions. Compound (1) crystallizes as a hemi-hydrate in the triclinic space group P-1 with a = 8.667(5) Å, b = 11.421(7) Å, c = 12.954(8) Å, α = 78.330(10)°, β = 84.553(10)°, γ = 75.510(9)°, and Z = 4. Compound (2) crystallizes in the monoclinic space group P21/c with a = 10.740(3) Å, b = 21.487(6) Å, c = 14.914(4) Å, β = 95.014(5)°, and Z = 12.

Index Abstract

Substantial hydrogen-bonding interactions leading to layer structures feature in each of the crystal structures of the isomeric title compounds.

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References

  1. McCluskey A, Keller PA, Morgan J, Garner J (2003) Org Biomol Chem 1:3353–3361

    Article  CAS  Google Scholar 

  2. Garner J, Hill T, Odell L, Keller PA, Morgan J, McCluskey A (2004) Aust J Chem 57:1079–1083

    Article  CAS  Google Scholar 

  3. Amm M, Platzer N, Guilhem J, Bouchet JP, Volland JP (1998) Magn Reson Chem 36:587–596

    Article  CAS  Google Scholar 

  4. Sheldrick GM (2003) SADABS. Version 2.10. University of Göttingen, Germany

    Google Scholar 

  5. Otwinowski Z, Minor W (1997) Methods in enzymology, vol 276. In: Part A, Carter CW Jr, Sweet RM (eds) Macromolecular crystallography. Academic Press, New York, pp 307–326

    Chapter  Google Scholar 

  6. Sheldrick GM (1997) SHELXS97. University of Göttingen

  7. Sheldrick GM (1997) SHELXL97. University of Göttingen, Germany

    Google Scholar 

  8. Johnson CK (1976) ORTEP II, Report ORNL-5136. Oak Ridge National Laboratory, Oak Ridge

    Google Scholar 

  9. Crystal Impact (2006) DIAMOND. Version 3.1c. Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany

  10. Gans J, Shalloway D (2001) J Mol Graph Model 19:557–559

    Article  CAS  Google Scholar 

  11. teXsan (1992) Structure Analysis Package. Molecular Structure Corporation, Houston, TX

  12. Spek AL (2005) PLATON, A multipurpose crystallographic tool. Utrecht University, Utrecht

    Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge financial support for this work from the National Health and Medical Research Council, Australia.

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Authors and Affiliations

  1. Department of Chemistry, School of Environmental and Life Sciences, University of Newcastle, University Drive, Callaghan, NSW, 2308, Australia

    Luke R. Odell & Adam McCluskey

  2. School of Chemistry, University of Sydney, Sydney, NSW, 2006, Australia

    Timothy W. Failes

  3. Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249-0698, USA

    Edward R. T. Tiekink

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  1. Luke R. Odell
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  2. Adam McCluskey
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  3. Timothy W. Failes
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  4. Edward R. T. Tiekink
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Correspondence to Edward R. T. Tiekink.

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Odell, L.R., McCluskey, A., Failes, T.W. et al. Crystal and Molecular Structures of Benzyl-(2-chloro-6-methylpyrimidin-4-yl)amine and Benzyl-(4-chloro-6-methylpyrimidin-2-yl)amine: Confirmation of Computationally Predicted Restricted Rotation. J Chem Crystallogr 37, 817–824 (2007). https://doi.org/10.1007/s10870-007-9253-2

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