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
Open Access
- 31 March 2021
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 12 (1), 81-85
- https://doi.org/10.5155/eurjchem.12.1.81-85.2107
Abstract
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.Keywords
This publication has 25 references indexed in Scilit:
- A study of antituberculosis activities and crystal structures of (E)-2-[2-(arylidene)hydrazinyl]pyrimidine and (E)-N 1-(arylidene)pyrimidine-2-carbohydrazide derivativesZeitschrift für Naturforschung B, 2020
- 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 compoundsSteroids, 2020
- Crystal structures and Hirshfeld surface analyses of a des-A-B-aromatic steroidal compound, and two of its derivatives, having a trans-2,3,4,5-tetrahydro-3a-methyl-7-methoxybenz[e]indane skeleton – structural comparisons with reported tetrahydrobenz[e]indene derivativesZeitschrift für Naturforschung B, 2019
- Synthesis, potent anti-TB activity against M. tuberculosis ATTC 27294, crystal structures and complex formation of selected 2-arylidenehydrazinylbenzothiazole derivativesJournal of Molecular Structure, 2018
- Crystal structures and Hirshfeld surface analyses of the di- and tri-hydrates of (5α,17E)-17-hydrazonoandrostan-3-ol: Significant differences in the hydrogen bonding patterns and supramolecular arrangementsSteroids, 2018
- Crystal structures and Hirshfeld surface analyses of the hemi-hydrate and hemi-methanolate of 3α-hydroxy-16α-bromoandrostan-17-one, 3: Differences in supramolecular arrangementsSteroids, 2018
- Crystal structures of (E)-2-((2-((pyridin-2-yl)hydrazonyl)methyl)phenolic compounds: different sets of classical hydrogen bonds, X–H···Y (X, Y = O, N)Zeitschrift für Kristallographie - Crystalline Materials, 2016
- Crystal structures of (E)-2-(2-benzylidenehydrazinyl)quinoxalines: persistent N–H···N intermolecular hydrogen bonds but variable π···π interactionsZeitschrift für Kristallographie - Crystalline Materials, 2014
- Design, synthesis and biological evaluation of (E)-2-(2-arylhydrazinyl)quinoxalines, a promising and potent new class of anticancer agentsBioorganic & Medicinal Chemistry Letters, 2014
- Clarification of the crystalline forms of androsteroneCrystEngComm, 2006