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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


James Lewis Wardell (1,*) orcid , John Nicholson Low (2) orcid

(1) Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK
(2) Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK
(*) Corresponding Author

Received: 31 Jan 2021 | Revised: 19 Feb 2021 | Accepted: 20 Feb 2021 | Published: 31 Mar 2021 | Issue Date: March 2021

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


Steroids; Hydrates; Hydrazones; Conformation; Hydrogen bonds; X-ray crystallography

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DOI: 10.5155/eurjchem.12.1.81-85.2107

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Funding information


National Crystallographic Service, University of Southampton, UK.

References


[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.
https://doi.org/10.1016/j.molstruc.2018.10.030

[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.
https://doi.org/10.1515/zkri-2015-1910

[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.
https://doi.org/10.1515/zkri-2014-1769

[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.
https://doi.org/10.1016/j.bmcl.2013.12.074

[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.
https://doi.org/10.1515/znb-2020-0108

[7]. Gomes, L. R.; Low, J. N.; Turner, A. B.; Baddeley, T. C.; Wardell, J. L. Steroids 2018, 140, 92-103.
https://doi.org/10.1016/j.steroids.2018.09.010

[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.
https://doi.org/10.1515/znb-2019-0094

[9]. Gomes, L. R.; Low, J. N.; Turner, A. B.; Wardell, J. L. Steroids 2018, 137, 30-39.
https://doi.org/10.1016/j.steroids.2018.07.005

[10]. Wardell, S. M. S. V.; Wardell, J. L. Steroids 2020, 159, 108624.
https://doi.org/10.1016/j.steroids.2020.108624

[11]. Hulme, A. T.; Lancaster, R. W.; Cannon, H. F. CrystEngComm 2006, 8 (4), 309-312.
https://doi.org/10.1039/b602909d

[12]. Weeks, C. M.; Cooper, A.; Norton, D. A.; Hauptman, H.; Fisher, J. Acta Crystallogr. B 1971, 27 (8), 1562-1572.
https://doi.org/10.1107/S0567740871004382

[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.
https://doi.org/10.1107/S1600536811011706

[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.
https://doi.org/10.1107/S1600536801001490

[15]. Cui, J.; Liu, L.; Zhao, D.; Gan, C.; Huang, X.; Xiao, Q.; Qi, B.; Yang, L.; Huang, Y. Steroids 2015, 95, 32-38.
https://doi.org/10.1016/j.steroids.2015.01.002

[16]. Ke, S.; Wei, Y.; Shi, L.; Yang, Q.; Yang, Z. Anticancer Agents Med. Chem. 2013, 13 (8), 1291-1298.
https://doi.org/10.2174/18715206113139990323

[17]. CrysAlis PRO 1.171.39.34b, 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.
https://doi.org/10.1039/B407861F

[19]. Sheldrick, G. M. Acta Crystallogr. C 2015, 71 (1), 3-8.
https://doi.org/10.1107/S2053273314026370

[20]. Hübschle, C. B.; Sheldrick, G. M.; Dittrich, B. J. Appl. Cryst. 2011, 44 (6), 1281-1284.
https://doi.org/10.1107/S0021889811043202

[21]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42 (2), 339-341.
https://doi.org/10.1107/S0021889808042726

[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.
https://doi.org/10.1107/S1600576719014092

[23]. CrysAlis PRO 1.171.39.9g: Oxford Diffraction /Agilent Technologies UK Ltd, Yarnton, England, 2015.

[24]. Spek, A. L. Acta Crystallogr. D Biol. Cryst. 2009, 65 (2), 148-155.
https://doi.org/10.1107/S090744490804362X

[25]. Parsons, S.; Flack, H. D.; Wagner, T. Acta Crystallogr. B 2013, 69 (3), 249-259.
https://doi.org/10.1107/S2052519213010014

[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.
https://doi.org/10.1107/S2052520616003954

[28]. Visbal, G.; San-Blas, G.; Maldonado, A.; Alvarez-Aular, A.; Capparelli, M. V.; Murgich, J. Steroids 2011, 76 (10-11), 1069-1081.
https://doi.org/10.1016/j.steroids.2011.04.012

[29]. Bertolasi, V.; Bortolini, O.; Fantin, G.; Fogagnolo, M.; Perrone, D. Steroids 2007, 72 (11-12), 756-764.
https://doi.org/10.1016/j.steroids.2007.06.005


Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Wardell, J.; Low, J. Eur. J. Chem. 2021, 12(1), 81-85. doi:10.5155/eurjchem.12.1.81-85.2107
Wardell, J.; Low, J. 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(1), 81-85. doi:10.5155/eurjchem.12.1.81-85.2107
Wardell, J., & Low, J. (2021). 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. European Journal of Chemistry, 12(1), 81-85. doi:10.5155/eurjchem.12.1.81-85.2107
Wardell, James, & John Nicholson Low. "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." European Journal of Chemistry [Online], 12.1 (2021): 81-85. Web. 12 Apr. 2021
Wardell, James, AND Low, John. "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" European Journal of Chemistry [Online], Volume 12 Number 1 (31 March 2021)

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