Crystal structures of 3β,19-dihydroxyandrost-5-en-17-one, 5, and its monohydrate, [(5).H2O]: A survey of the structures of related di- and tri-substituted hydroxy derivatives and their solvated compounds

Wardell, Solange M. S. V.; Wardell, Jámes L.

doi:10.1016/j.steroids.2020.108624

Cited by 3 publications

(1 citation statement)

References 32 publications

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“…As is evident from such studies of compound 1 [7] and the solvates of 3α-hydroxy-16α-bromoandrostan-17-one (4), [9] and 3β,19-dihydroxyandrost-5-en-17-one (5), [10] the solvate molecules have major influences on the packing of the steroid molecules, in particular on the linking of the steroid moieties. Compounds, such as 5α-androstane-3α-ol-17-one, and epiandrosterone, with a hydroxyl donor group, at one end of the molecule, e.g., on C-3, and an acceptor group, such as a carbonyl group at the other end of the molecule on C-17 [11][12][13][14], link directly in a head-to-tail linked via C-H---O hydrogen bonds, however on solvation, the prevalence of the direct head-to-tail links is reduced with an corresponding increase in the percentages of solvent linked steroids.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure of the sesquihydrate of dehydroepiandrosterone propan-2-ylidene hydrazone: Participation of the hydrazonyl nitrogen atoms as acceptors in the elaborate hydrogen bond scheme

Wardell

Low

2021

Eur J Chem

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The crystal structure of the sesquihydrate of dehydroepiandrosterone propan-2-ylidene hydrazone, [(7)2·(H2O)3], isolated from a solution of dehydroepiandrosterone propan-2-ylidene hydrazone, (7), in moist ethanol at room temperature, has been determined from data collected at 100 K. The sesquihydrate recrystallizes in the orthorhombic space group, P212121 with Z = 8. The asymmetric unit of [(7)2·(H2O)3] consists of two independent molecules of the steroid, Mol A and Mol B, and three moles of water. The six membered saturated rings, A and C, in both molecules have ideal or near ideal chair shapes, the unsaturated rings, B, have the expected half-chair shapes, while the five-membered rings, D, have envelope shapes with flaps at C114 and C214 for Mol A and Mol B, respectively. Differences in the conformations of the two molecules reside essentially completely within the hydrazonyl fragments with significantly different torsional angles, C117-N120-N121-C122 (in Mol A) and C217-N220-N221-C222 (in Mol B), of 149.19(14) and -93.08(17)°, respectively. The difference in this torsional angle is reflected in the hydrogen bonds involving the nitrogen atoms in the hydrazonyl units: it is of interest that the hydrazonyl nitrogen atoms partake as acceptors in hydrogen bonding with water molecules. The only intermolecular interactions in these molecules are hydrogen bonds -all classical O-H-O and OH···N hydrogen bonds with just one exception, a C-H···O(water) hydrogen bond. Of interest, there are no direct steroid-steroid links: molecules are linked solely by hydrogen bonds involving the hydrate molecules. All three hydrate molecules take part in the indirect linking of the steroid molecules, but each has its own set of contacts.

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Section: Introductionmentioning

confidence: 99%

Crystal structure of the sesquihydrate of dehydroepiandrosterone propan-2-ylidene hydrazone: Participation of the hydrazonyl nitrogen atoms as acceptors in the elaborate hydrogen bond scheme

Wardell

Low

2021

Eur J Chem

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Synthesis, characterization and in silico screening of potential biological activity of 17α-ethynyl-3β, 17β, 19-trihydroxyandrost-5-en acetylated derivatives

Ochoa

Farfán

Soto-Castro

et al. 2021

Journal of Molecular Structure

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Crystal structure, Hirshfeld surface analysis and Pixel calculations of the monohydrate of (E)-3-(2-hydroxy-5-methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one: occurrence of π interactions

Gomes

Low

Turner

et al. 2021

Zeitschrift Für Naturforschung B

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A detailed structural analysis has been carried out on the monohydrate of (E)-3-(2-hydroxy-5-methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one, 1·H2O. The molecule, 1, shows a small deviation from planarity with an interplanar angle between the phenyl groups of 13.32(6)°. Classical O–H⋯O hydrogen bonds involving the water molecule play significant roles in determining the overall structure. The chalcone molecules in the structure are linked directly by C–H⋯O and off-set face-to-face π⋯π intermolecular interactions, as well as indirectly via interactions involving the water molecule in an elaborate spiralling hydrogen bonding scheme. The relative contributions of various intermolecular contacts were investigated using Hirshfeld surface analysis and the associated two dimensional fingerprint plots. Pairs of molecules were identified in the crystal structure using the Pixel method. The Pixel lattice energy calculations revealed that the dispersion and the Coulombic components were the major contributors to the packing stabilization. Comparisons were made between the structures of 1·H2O and hydroxylated (E)-3-(2-hydroxyphenyl)-1-phenyl-prop-2-en-1-one derivatives, in particular in regards to the participation of π interactions.

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Crystal structures of 3β,19-dihydroxyandrost-5-en-17-one, 5, and its monohydrate, [(5).H2O]: A survey of the structures of related di- and tri-substituted hydroxy derivatives and their solvated compounds

Cited by 3 publications

References 32 publications

Crystal structure of the sesquihydrate of dehydroepiandrosterone propan-2-ylidene hydrazone: Participation of the hydrazonyl nitrogen atoms as acceptors in the elaborate hydrogen bond scheme

Crystal structure of the sesquihydrate of dehydroepiandrosterone propan-2-ylidene hydrazone: Participation of the hydrazonyl nitrogen atoms as acceptors in the elaborate hydrogen bond scheme

Synthesis, characterization and in silico screening of potential biological activity of 17α-ethynyl-3β, 17β, 19-trihydroxyandrost-5-en acetylated derivatives

Crystal structure, Hirshfeld surface analysis and Pixel calculations of the monohydrate of (E)-3-(2-hydroxy-5-methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one: occurrence of π interactions

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