Acta Crystallographica Section E: Crystallographic Communications (Jun 2016)

Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug

  • José A. Carmona-Negrón,
  • Mariola M. Flores-Rivera,
  • Zaibeth Díaz-Reyes,
  • Curtis E. Moore,
  • Arnold L. Rheigold,
  • Enrique Meléndez

DOI
https://doi.org/10.1107/S2056989016008446
Journal volume & issue
Vol. 72, no. 6
pp. 868 – 871

Abstract

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A new ferrocene complex, 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one dimethyl sulfoxide monosolvate, [Fe(C5H5)(C24H27O2)]·C2H6OS, has been synthesized and structurally characterized by single-crystal X-ray diffraction techniques. The molecule crystallizes in the space group P21 with one molecule of dimethyl sulfoxide. A hydrogen bond links the phenol group and the dimethyl sulfoxide O atom, with an O...O distance of 2.655 (5) Å. The ferrocene group is positioned in the β face of the estrone moiety, with an O—C—C—C torsion angle of 44.1 (5)°, and the carbonyl bond length of the hormone moiety is 1.216 (5) Å, typical of a C=O double bond. The average Fe—C bond length of the substituted Cp ring [Fe—C(Cp*)] is similar to that of the unsubstituted one [Fe—C(Cp)], i.e. 2.048 (3) versus 2.040 (12) Å. The structure of the complex is compared with those of estrone and ethoxymethylestrone.

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