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Intermolecular Hydrogen Bonds and the Supramolecular Structure of N,N′-Bis(p-tolylsulfonyl)diethylenetriamine

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Abstract

The title compound N,N′-bis(p-tolylsulfonyl)diethylenetriamine (1) was synthesized and its crystal structure determined by X-ray diffraction. Adjacent molecules of 1, symmetrically related through a c-glide, are linked by alternating hydrogen bonds that form molecular chains along [0 0 1]. Two molecular chains occur in each unit cell and pack to form alternating layers in a three-dimensional supramolecular structure. The compound crystallizes in the Pca21 space group stabilized by the inclusion of solvent dichloromethane molecules in structural voids between molecules of 1. The dichloromethane molecules are related through a twofold screw rotation axis and are not disordered.

Index Abstract

Intermolecular hydrogen bonds involving sulfonamide moieties of title compound afford a supramoleular structure that accommodates the inclusion of dichloromethane in alternating layers.

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References

  1. Smith MB, March J (2001) Advanced organic chemistry: reactions, mechanisms, and structure, 5th edn. John Wiley and Sons, New York

    Google Scholar 

  2. Richman JE, Atkins TJ (1974) J Am Chem Soc 96:2268

    Article  CAS  Google Scholar 

  3. de Silva AP, Fox DB, Huxley AJM, McClenaghan ND, Roiron J (1999) Coord Chem Rev 185:297

    Article  Google Scholar 

  4. Parker D (2004) Chem Soc Rev 33:156

    Article  CAS  Google Scholar 

  5. de Silva AP, Fox DB, Huxley AJM, Moody TS (2000) Coord Chem Rev 205:41

    Article  Google Scholar 

  6. Bottrill M, Kwok L, Long NL (2006) Chem Soc Rev 35:557

    Article  CAS  Google Scholar 

  7. Scheuermann JEW, Sibbons KF, Benoit DM, Motevalli M, Watkinson M (2004) Org Biomol Chem 2:2664

    Article  CAS  Google Scholar 

  8. Shaw BL (1975) J Am Chem Soc 97:3856

    Article  CAS  Google Scholar 

  9. APEX2 (2005) Ver 2.0–1. Bruker AXS Inc., Madison, Wisconsin, USA

    Google Scholar 

  10. SAINT-NT (includes XPREP, SADABS) (2005) Ver. 6.0. Bruker AXS Inc., Madison, Wisconsin, USA

    Google Scholar 

  11. SHELXTL (includes XS, XL, XP, XSHELL) (1999) Ver. 5.1. Bruker AXS Inc., Madison, Wisconsin, USA

    Google Scholar 

  12. Spek AL (2003) J Appl Cryst 36:7

    Article  CAS  Google Scholar 

  13. Farrugia LJ (1997) J Appl Cryst 30:565

    Article  CAS  Google Scholar 

  14. Dijksman A, Elzinga JM, Li Y-X, Arends IWCE, Sheldon RA (2002) Tetrahedron Asymmetry 13:879

    Article  CAS  Google Scholar 

  15. Hope DB, Horncastle KC (1966) J Chem Soc C 12:1098

    Article  CAS  Google Scholar 

  16. Martin AE, Ford TM, Bulkowski JE (1982) J Org Chem 47:412

    Article  CAS  Google Scholar 

  17. Skinner MEG, Li Y, Mountford P (2002) Inorg Chem 41:1110

    Article  CAS  Google Scholar 

  18. Görbitz CH, Hersleth H-P (2000) Acta Cryst B56:526

    Google Scholar 

  19. Dielemann C, Matt D, Jones PG, Thönnessen H (2003) Acta Cryst C59:o247

    CAS  Google Scholar 

  20. Biradha K, Sharma CVK, Panneerselvam K, Shimoni L, Carrell HL, Zacharias DE, Desiraju GR (1993) J Chem Soc Chem Commun 1473

  21. Bernstein J, Davis RE, Shinoni L, Chang NL (1995) Angew Chem Int Ed Engl 34:1555

    Article  CAS  Google Scholar 

  22. Golubev SN, Kondrashev YD (1981) J Struct Chem 22:59

    Article  Google Scholar 

Download references

Acknowledgments

We thank the H. E. Griffin Trust (A.S.S.), the University of the Witwatersrand (A.S.S., H.M.M.), the National Research Foundation (K.P., H.M.M.), the South African Research Chairs Initiative of the Department of Science and Technology, and the National Research Foundation (H.M.M.) for financial support.

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Correspondence to A. S. de Sousa.

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Padayachy, K., Fernandes, M.A., Marques, H.M. et al. Intermolecular Hydrogen Bonds and the Supramolecular Structure of N,N′-Bis(p-tolylsulfonyl)diethylenetriamine. J Chem Crystallogr 38, 577–582 (2008). https://doi.org/10.1007/s10870-008-9337-7

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  • DOI: https://doi.org/10.1007/s10870-008-9337-7

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