Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

The Structure of 1-[2-[[(4-chlorophenyl)-methyl]thio]-2-(2, 4-dichlorphenyl)ethyl]-1H imidazole (Sulconazole) nitrate, C18H16Cl3N3O3S

  • Shin, Hyun-So (Department of Chemical Engineering, Dongguk University) ;
  • Song, Hyun (Department of Chemical Engineering, Dongguk University) ;
  • Cho, Sung-Il (Department of Chemical Engineeing, Seoul city University) ;
  • Pakr, Keun-Il (Department of Chemical Engineeing, Seoul city University)
  • Published : 1997.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

Sulconazole nitrate, C18H16Cl3N3O3S, crystallizes in monoclinic, space group C2/c, with a=14.401(1), b=8.051(1), c=34.861(2) Å, β=95.9(1)°, g=0.58 mm-1, Dc=1.523 g/cm3, Dm=1.522 g/cm3, F(000)=1888.0, and z=8. Intensities for 2460 unique reflections were measured on a CAD4 diffractometer with graphited-monochromated Mo-Kα radiation. The structure was solved by direct method and refined by full matrix least squares to a final R=0.071 for 2182 reflections (Io > 2σIo). The bond lengths and angles are comparable with the values found in the analogues imidazole derivatives. The 2,4-dichlorophenyl ring(A) and the p-chlorophenyl ring(B) are almost planar with different heights [dihedral angle 17.3°] while the imidazole ring(C) is nearly perpendicular to the two phenyl rings[dihedral angles about the two rings A, B are 110.8° and 96.1° respectively]. In order to understand the overall conformation we calculated the selected distances (l1, l2, l3) among the center of the three rings and considered the imaginary plan D[C(7), C(9) and C(16)]. The two polar group S(8) and N(19) do not have gauche conformation and l2 value (4.47 Å) is shorter than the other imidazole derivatives. One -NO3 group are hydrogen bonded the two neighbored sulconazole molecules. The molecular crystal packing is also formed by two hydrogen bondings and van der Waals forces.

Keywords

References

  1. Essential of Medicinal Chemistry(2nd ed.) Korolkovas, A.
  2. Comprehensive Medicinal Chemistry v.2 Hansch, C.;Sammes, P.;Taylor, J. B.
  3. Biochemistry v.26 Poulos, T. L.;Howard, A. J.
  4. U. S. Pat. 4,038,409 Walker, K. A. M.;Mars, M.
  5. Proc. West. Pharma. Soc. v.25 Zaro, B. A.
  6. Bull. Soc. Cheim. Belg. v.88 Peeters, O. M.;Blaton, N. M.;De Ranter, C. J.
  7. Acta Cryst. v.C42 Freer, A. A.;Pearson, A.;Salole, E. G.
  8. Kor. J. Cryst. v.1 Suh, I. W.;Cho, S. I.;Park, K. I.
  9. SHELXS-86. Program for Crystal Structure Determination Sheldrick, G. M.
  10. SHELXL-93. Program for Crystal Structure Determination Sheldrick, G. M.
  11. International Tables for Crystallography v.C
  12. ORTEX 3.1. Molecular Graphic Program Mcardle, P.
  13. Biochemistry v.19 Dahl, C. E.;Dahl, J. S.;Bloch, K.
  14. Spec. Publ. Royal Soc. Chem. v.50 Marchington, A. F.

Cited by

  1. Structural confirmation of sulconazole sulfoxide as the primary degradation product of sulconazole nitrate vol.8, pp.2, 2018, https://doi.org/10.1016/j.jpha.2017.12.007