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Crystal structure of 16-ferrocenylmethyl-3?-hydroxy-estra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug.

ABSTRACT: A new ferrocene complex, 16-ferrocenylmethyl-3?-hy-droxy-estra-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 mol-ecule crystallizes in the space group P21 with one mol-ecule 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 ? 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 eth-oxy-methyl-estrone.

SUBMITTER: Carmona-Negron JA 

PROVIDER: S-EPMC4908549 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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

Carmona-Negrón José A JA   Flores-Rivera Mariola M MM   Díaz-Reyes Zaibeth Z   Moore Curtis E CE   Rheigold Arnold L AL   Meléndez Enrique E  

Acta crystallographica. Section E, Crystallographic communications 20160527 Pt 6

A new ferrocene complex, 16-ferrocenylmethyl-3β-hy-droxy-estra-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 mol-ecule crystallizes in the space group P21 with one mol-ecule 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  ...[more]

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