X-Ray Diffraction Study of the Crystal Structure of 2-[Phenyl-(2-hydroxyethylthio)methyl]-cyclohexanone, a Candidate Prodrug of the Cytotoxin E-2-Benzylidenecyclohexanone

• Published in: Crystallography reports Vol. 66; no. 6; pp. 985 - 990
• Main Authors: Doroudi, A., Zhu, J., Dimmock, J. R., Das, U.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.11.2021; Springer Nature B.V
• Subjects: Crystal structure; Crystallography and Scattering Methods; Cyclohexanone; Hydrogen bonding; NMR spectroscopy; Oxygen atoms; Physics; Physics and Astronomy; Single crystals; Stereochemistry; Structure of Organic Compounds; Unit cell; X-ray diffraction
• ISSN: 1063-7745; 1562-689X
• DOI: 10.1134/S1063774521060092

This investigation describes the synthesis and X-ray diffraction study of the crystal structure of a novel prodrug 2-[phenyl-(2-hydroxyethylthio)methyl]cyclohexanone ( 2 ). Compound 2 was prepared by the reaction between E -2-benzylidenecyclohexanone ( 1 ) and 2-mercaptoethanol. The structure of 2 was determined by single crystal X-ray diffraction and 1 H NMR spectroscopy. The crystal of 2 is monoclinic, space group is P 2 1 / c with unit cell parameters a = 9.2098(7) Å, b = 22.1518(17) Å, c = 7.3455(5) Å, β = 112.816(3)°, Z  = 4, R 1 = 0.066, and wR 2 = 0.209 ( F    2 ). The cyclohexyl ring assumes the chair conformation, while the two stereogenic centres at carbon atoms C6 and C7 display the S and R stereochemistry, respectively. In addition, hydrogen bonding is observed between the O2–H hydrogen and O1 oxygen atoms.