European Journal of Chemistry

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


Main Article Content

James Lewis Wardell
John Nicholson Low


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.

icon graph This Abstract was viewed 833 times | icon graph Article PDF downloaded 432 times icon graph Article CIF FILE downloaded 0 times

How to Cite
Wardell, J. L.; Low, J. N. 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. Eur. J. Chem. 2021, 12, 81-85.

Article Details

Crossref - Scopus - Google - European PMC

[1]. Pinheiro, Alessandra. C.; de Souza, Marcus. V. N.; Lourenço, Maria. C. S.; da Costa, C. F.; Baddeley, T. C.; Low, J. N.; Wardell, Solange. M. S. V.; Wardell, J. L. Synthesis, Potent Anti-TB Activity against M. J. Mol. Struc. 2019, 1178, 655-668.

[2]. Gonzaga, D. T. G.; Silva, F. C. da; Ferreira, V. F.; Wardell, J. L.; Wardell, S. M. S. V. J. Brazilian Chem. Soc. 2016, 27, 2322-2333.

[3]. Correira, N. R. de L.; Noguiera, T. C. M.; Pinheiro, A. C.; de Souza, M. V. N.; Wardell, J. L.; Wardell, S. M. S. V. Z. Kristallog. Cryst. Mater. 2016, 231 (5), 271-284.

[4]. de Souza, M. V. N.; Noguiera, T. C. M.; Wardell, S. M. S. V.; Wardell, J. L. Z. Kristallog. Cryst. Mater. 2014, 229 (8), 587-594.

[5]. Rodrigues, F. A. R.; Bomfim, I. da S.; Cavalcanti, B. C.; Pessoa, C. do O.; Wardell, J. L.; Wardell, S. M. S. V.; Pinheiro, A. C.; Kaiser, C. R.; Nogueira, T. C. M.; Low, J. N.; Gomes, L. R.; de Souza, M. V. N. Bioorg. Med. Chem. Lett. 2014, 24 (3), 934-939.

[6]. Pinheiro, A. C.; Nogueira, T. C. M.; da Costa, C. F.; Lourenço, C.; Low, J. N.; Wardell, J. L.; Wardell, S. M. S. V.; de Souza, M. V. N. Z. Naturforsch. B 2020, 75 (12), 1011-1028.

[7]. Gomes, L. R.; Low, J. N.; Turner, A. B.; Baddeley, T. C.; Wardell, J. L. Steroids 2018, 140, 92-103.

[8]. Gomes, L. R.; Low, J. N.; Turner, A. B.; Nowicki, A. W.; Baddeley, T. C.; Wardell, J. L. Z. Naturforsch. B 2019, 74 (9), 649-663.

[9]. Gomes, L. R.; Low, J. N.; Turner, A. B.; Wardell, J. L. Steroids 2018, 137, 30-39.

[10]. Wardell, S. M. S. V.; Wardell, J. L. Steroids 2020, 159, 108624.

[11]. Hulme, A. T.; Lancaster, R. W.; Cannon, H. F. CrystEngComm 2006, 8 (4), 309-312.

[12]. Weeks, C. M.; Cooper, A.; Norton, D. A.; Hauptman, H.; Fisher, J. Acta Crystallogr. B 1971, 27 (8), 1562-1572.

[13]. Andrade, L. C. R.; Almeida, M. J. B. M. de; Paixao, J. A.; Carvalho, J. F. S.; Sa e Melo, M. L. Acta Crystallogr. E 2011, 67 (5), o1056-o1057.

[14]. Novoa de Armas, H.; Peeters, O. M.; Blaton, N. M.; De Ranter, C. J.; Ruiz Garcia, J. A.; Reyes Moreno, M.; Alvarez Ginarte, Y. M. Acta Crystallogr. E 2001, 57 (2), o166-o167.

[15]. Cui, J.; Liu, L.; Zhao, D.; Gan, C.; Huang, X.; Xiao, Q.; Qi, B.; Yang, L.; Huang, Y. Steroids 2015, 95, 32-38.

[16]. Ke, S.; Wei, Y.; Shi, L.; Yang, Q.; Yang, Z. Anticancer Agents Med. Chem. 2013, 13 (8), 1291-1298.

[17]. CrysAlis PRO, Version 7, Oxford Diffraction /Agilent Technologies UK Ltd, Yarnton, England, 2017.

[18]. McArdle, P.; Gilligan, K.; Cunningham, D.; Dark, R.; Mahon, M. CrystEngComm 2004, 6 (53), 303-309.

[19]. Sheldrick, G. M. Acta Crystallogr. C 2015, 71 (1), 3-8.

[20]. Hübschle, C. B.; Sheldrick, G. M.; Dittrich, B. J. Appl. Cryst. 2011, 44 (6), 1281-1284.

[21]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42 (2), 339-341.

[22]. Macrae, C. F.; Sovago, I.; Cottrell, S. J.; Galek, P. T. A.; McCabe, P.; Pidcock, E.; Platings, M.; Shields, G. P.; Stevens, J. S.; Towler, M.; Wood, P. A. J. Appl. Cryst. 2020, 53 (1), 226-235.

[23]. CrysAlis PRO Oxford Diffraction /Agilent Technologies UK Ltd, Yarnton, England, 2015.

[24]. Spek, A. L. Acta Crystallogr. D Biol. Cryst. 2009, 65 (2), 148-155.

[25]. Parsons, S.; Flack, H. D.; Wagner, T. Acta Crystallogr. B 2013, 69 (3), 249-259.

[26]. Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Turner, M. J.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer (Version 3.1), University of Western Australia, Perth, Australia, 2012.

[27]. Groom, C. R.; Bruno, I. J.; Lightfoot, M. P.; Ward, S. C. Acta Crystallogr. B 2016, 72 (2), 171-179.

[28]. Visbal, G.; San-Blas, G.; Maldonado, A.; Alvarez-Aular, A.; Capparelli, M. V.; Murgich, J. Steroids 2011, 76 (10-11), 1069-1081.

[29]. Bertolasi, V.; Bortolini, O.; Fantin, G.; Fogagnolo, M.; Perrone, D. Steroids 2007, 72 (11-12), 756-764.

Supporting Agencies

National Crystallographic Service, University of Southampton, UK.
Most read articles by the same author(s)

Most read articles by the same author(s)


Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).