Skip to main content
SpringerLink
Log in

The crystal and molecular structure of 1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl) Urea: Tolazamide (C14H21N3O3S)

  • Original Articles
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Crystals of tolazamide, C14H21N3O3S, are triclinic, space group PĪ, with cell dimensions ofa=6.355(2),b=9.223(2),c=13.510(3) A, α=101.04(8), β=92.80(5), γ=85.72(6)° and Z=2. Intensities were collected on an automated four-circle diffractometer using graphite-monochromated Cu K α radiations. The structure was solved by direct method and refined by full-matrix least-squares to an R factor of 0.058 for 1184 observed reflections. The molecules are dimerized by the N-H···O hydrogen bonds. There are only van der Waals interactions between these molecular dimers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  1. Main, P., Lessinger, L., Woolfson, M.M., Germain, G. & Declercq, J.P.: MULTAN; A system of computer programs for the automatic solution of non-centrosymmetric crystal structure analysis. Univ. of York, England, and Louvain Belgium. (1977).

    Google Scholar 

  2. Sheldrick, G.M.: SHELX 76. Program for crystal structure determination. Univ. of Cambridge, England. (1976).

    Google Scholar 

  3. Johnson, C.K.: ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee. (1965).

    Google Scholar 

  4. Alleaume, M., Gulko, A., Herbstein, F.H., Kapon, M. & March, R.E.: Comparison of the Dimensions and Conformation of the Sulfaguanidine Moiety in Sulfaguanidine Monohydrate and trans-Dichlorobis (sulfaguanidine) palladium (II).Acta Cryst.B32, 669 (1976).

    CAS  Google Scholar 

  5. Klug, H.P.: The Crystal Structure of Methanesulfonanilide.Acta Cryst. B24, 792 (1968).

    Google Scholar 

  6. Dupont, P.L., Lamotte, J. & Vermeire, H.C.M.: Structure Cristalline et Moleculaire d’nn Diuretique Derive, de 1 ’Alkyl-1-[(Phenylamino-4-pyridyl-3)-sulfonyl]-3-Uree: 1a Torasemide (C15H20N4SO3).Acta Cryst. B34, 1304 (1978).

    CAS  Google Scholar 

  7. Koo, C.H., Cho, S.I. and Yeon, Y.H.: The Crystal and Molecular Structure of Chlorpropamide.Arch. Pharm. Res. 3, 37 (1980).

    Article  CAS  Google Scholar 

  8. Cook, R.E., Glick, M.D., Rigau, J.J. & Johnson, C.R.: Structure of trans-4-tert-Butyl-1-[N-ethyl-N-p-toluenesulfonylamino]-1-thioniacyclohexane Fluroroborate. Evidence for p(N)-d(S) Bonding.J. Amer. Chem. Soc. 93, 924 (1971).

    Article  Google Scholar 

  9. Cruickshank, D.W.J.: The Role of 3d-Orbitals in π-Bonds between (a) Silicon, Phosphorous, Sulfur, or Chlorine and (b) Oxygen or nitrogen.J. Chem. Soc. 5486 (1961).

  10. Koo, C.H., Cho, S.I. and Yeon, Y.H.: The Crystal and Molecular Structure of Carbutamide.Yakhak Hoeji 20, 9 (1982).

    Google Scholar 

  11. Palm, T.B. & Csoregh, I.: The Crystal and Molecular Structure of Bacmecillinam Hydrochloride.Acta Cryst. B34, 138 (1978).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry College of Natural Sciences, Seoul National University, 151-742, Seoul, Korea

    Chung Hoe Koo, Jung Sun Suh & Young Hee Yeon

  2. Department of Chemistry, Osaka University, Osaka, Japan

    Tokunosuke Watanabe

Authors
  1. Chung Hoe Koo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jung Sun Suh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Young Hee Yeon
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tokunosuke Watanabe
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koo, C.H., Suh, J.S., Yeon, Y.H. et al. The crystal and molecular structure of 1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl) Urea: Tolazamide (C14H21N3O3S). Arch. Pharm. Res. 11, 74–79 (1988). https://doi.org/10.1007/BF02884772

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02884772

Keywords

Search

Navigation