

Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains
John Nicolson Low (1)





(1) Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland
(2) Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland
(3) Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, Rio de Janeiro, Brazil
(4) Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, Rio de Janeiro, Brazil
(5) FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal
(*) Corresponding Author
Received: 14 May 2018 | Revised: 04 Jun 2018 | Accepted: 05 Jun 2018 | Published: 30 Sep 2018 | Issue Date: September 2018
Abstract
In order to further investigate the structural chemistry of oximes and to further establish the main structural arrangements adopted, we have determined the crystal structure of and carried out Hirshfeld surface calculations on three heteroaryl oximes, namely (Z)-thiophene-2-carbaldehyde oxime (1), (Z)-1H-pyrrole-2 carbaldehyde oxime (2) and (Z)-5-nitrofuran-2-carbaldehyde oxime (3). As confirmed by both techniques, the major intermolecular interactions in each compound are classical N—H···O hydrogen bonds, which link the molecules into C3 chains. Such an arrangement has been previous reported as an important aggregation mode for oximes. Secondary interactions, C—H···π and C—H···O interactions, in compounds 1 and 2, and interactions involving the nitro group oxygen atoms in compound 3 link the chains into three dimensional arrays.
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DOI: 10.5155/eurjchem.9.3.151-160.1734
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Portuguese Foundation for Science and Technology (FCT) UID/Multi/04546/2013
Citations
[1]. Ligia R. Gomes, John N. Low, Tanja van Mourik, Herbert Früchtl, Marcus V.N. de Souza, Cristiane F. da Costa, James L. Wardell
Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: confirmation of attractive π(C=N)···π(phenyl) interactions
Zeitschrift für Naturforschung B 74(4), 319, 2019
DOI: 10.1515/znb-2018-0222

[2]. Ligia R. Gomes, Marcus V. N. de Souza, Cristiane F. Da Costa, James L. Wardell, John Nicolson Low
Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC6H3C=NOH (X = H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns
Acta Crystallographica Section E Crystallographic Communications 74(11), 1553, 2018
DOI: 10.1107/S2056989018014020

References
[1]. Abele, E.; Abele, R.; Lukevics, E. Chem. Heterocycl. Cmpds. 2018, 44, 769-792.
https://doi.org/10.1007/s10593-008-0110-9
[2]. Nikitjuka, A.; Jirgensons, A. Chem. Heterocycl. Cmpds. 2014, 49, 1544-1559.
https://doi.org/10.1007/s10593-014-1407-5
[3]. Martinez-Pascual, R.; Meza-Reyes, S.; Vega-Baez, J. L.; Merino-Montiel, P.; Padron, J. M.; Mendoza, A.; Montiel-Smith, S. Steroids 2017, 122, 24-33.
https://doi.org/10.1016/j.steroids.2017.03.008
[4]. Qin, H. L.; Leng, J.; Youssif, B. G. M.; Amjad, M. W.; Raja, M. A. G.; Hussain, M. A.; Hussain, Z.; Kazmi, S. N.; Bukhari, S. N. A. Chem. Bio. Drug Des. 2017, 90, 443-449.
https://doi.org/10.1111/cbdd.12964
[5]. Canario, C.; Silvestre, S.; Falcao, A.; Alves, G. Curr. Med. Chem. 2018, 25, 660-686.
[6]. Huang, G.; Zhao, H. R.; Meng, Q. Q.; Zhang, Q. J.; Dong, J. Y.; Zhu, B. Q.; Li, S. S. Eur. J. Med. Chem. 2018, 143, 166-181.
https://doi.org/10.1016/j.ejmech.2017.11.031
[7]. Dai, H.; Chen, J.; Li, G.; Ge, S. S.; Shi, Y. J.; Fang, Y.; Ling, Y. Bioorg. Med. Chem. Letters 2017, 27, 950-953.
https://doi.org/10.1016/j.bmcl.2016.12.083
[8]. Zhao, S. Y.; Li, K.; Jin, Y.; Lin, J. Eur. J. Med. Chem. 2018, 144, 41-51.
https://doi.org/10.1016/j.ejmech.2017.12.016
[9]. Yadav, P.; Lal, K.; Rani, P.; Mor, S.; Kumar, A.; Kumar, A. Med. Chem. Res. 2017, 26, 1469-1480.
https://doi.org/10.1007/s00044-017-1845-6
[10]. Kozlowska, J.; Potaniec, B.; Zarowska, B.; Aniol, M. Molecules 2017, 22. Article Number: UNSP 1485
[11]. Mohassab, A. M.; Hassan, H. A.; Abdelhamid, D.; Abdel-Aziz, M.; Dalby, K. N.; Kaoud, T. S. Bioorg. Chem. 2017, 75, 242-259.
https://doi.org/10.1016/j.bioorg.2017.09.018
[12]. Lorke, D. E.; Kalasz, H.; Petroianu, G. A.; Tekes, K. Curr. Med. Chem. 2008, 15, 743-753.
https://doi.org/10.2174/092986708783955563
[13]. Voicu, V. A.; Bajgar, J.; Medvedovici, A.; Radulescu, F. S.; Miron, D. S.; S. J. Appl. Tox. 2010, 719-729.
https://doi.org/10.1002/jat.1561
[14]. Katalinic, M.; Zandona, A.; Ramic, A.; Zorbaz, T.; Primozic, I.; Kovarik, Z. Molecules 2017, 22, Article number 1234.
https://doi.org/10.3390/molecules22071234
[15]. Radic, Z.; Dale, T.; Kovarik, Z.; Berend, S.; Garcia, E.; Zhang, L.; Amitais, G.; Green, C.; Radi, B.; Duggan, B. M.; Ajami, D.; Rebek, J.; Taylor. P. Biochem. J. 2013, 450, 231-242.
[16]. Sorensen, M.; Neilson, E. H. J.; Moller, B. L. Mol. Plant 2018, 11, 95-117.
https://doi.org/10.1016/j.molp.2017.12.014
[17]. Bertalosi, V.; Gilli, V.; Acta Cryst. B 1982, 38, 502-511
https://doi.org/10.1107/S0567740882003288
[18]. Bruton, E. A.; Brammer, L.; Pigge, F. C.; Aakeroy, C. B.; Leinen, D. S. New J. Chem. 2003, 27, 1084-1491.
https://doi.org/10.1039/B301045G
[19]. Low, J. N.; Santos, L. M. N. B. F.; Lima, C. F. R. A. C.; Brandao, P.; Gomes, L. R. Eur. J. Chem. 2010, 1, 61-66.
https://doi.org/10.5155/eurjchem.1.2.61-66.76
[20]. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
https://doi.org/10.1021/ar00172a005
[21]. Desiraju, G. R. Angew. Chem. Int. Ed. 2007, 46, 8342–8356.
https://doi.org/10.1002/anie.200700534
[22]. Liu, Y.; Cai, B.; Li, Y.; Song, H.; Huang, R.; Wang, Q. J. Agr. Food Chem. 2007, 55, 3011-3017.
https://doi.org/10.1021/jf0636519
[23]. http://www.chemspider.com/Chemical-Structure.5268628.html, (Retrieved 01/01/2018)
[24]. http://www.chemspider.com/Chemical-Structure.15526334.html, (Retrieved 01/01/2018)
[25]. Gilman, H.; Wright, G. F. J. Am. Chem. Soc. 1930, 52, 2550-2554.
https://doi.org/10.1021/ja01369a061
[26]. CrysAlis PRO 1.171.39.9g: Rigaku Oxford Diffraction, 2015
[27]. CrysAlis PRO 1.171.39.30d, Rigaku Oxford Diffraction, 2017.
[28]. McArdle, P.; Gilligan, K.; Cunningham, D.; Dark, R.; Mahon, M. Cryst. Eng. Comm. 2004, 6, 203-209.
https://doi.org/10.1039/B407861F
[29]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122.
https://doi.org/10.1107/S0108767307043930
[30]. Hubschle, C. B.; Sheldrick, G. M.; Dittrich, B. J. Appl. Cryst. 2011, 44, 1281-1284.
https://doi.org/10.1107/S0021889811043202
[31]. Sheldrick, G. M. Acta Cryst. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218
[32]. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; Van de Streek, J.; Wood, P. A. (MERCURY, CCDC, 2018) J. Appl. Cryst. 2008, 41, 466-470.
https://doi.org/10.1107/S0021889807067908
[33]. Spek, A. L. Acta Cryst. D 2009, 55, 148-155.
https://doi.org/10.1107/S090744490804362X
[34]. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Cryst. B 2004, 60, 627-668.
https://doi.org/10.1107/S0108768104020300
[35]. Wolff, S.; Grimwood, D.; McKinnon, J.; Turner, M.; Jayatilaka, D.; Spackman, M., Crystal Explorer, University of Western Australia Perth, Australia, 2012.
[36]. Wagner, P.; Officer, D. L.; Kubicki, M. Acta Cryst. E 2006, 62, o5931-o5932.
https://doi.org/10.1107/S1600536806050100
[37]. Zhang, X.; Chen Z.; Li, J.; Lu, T. J. Chem. Inf. Model, 2015, 55, 2138-2153.
https://doi.org/10.1021/acs.jcim.5b00177
[38]. Howie, R. A.; Wardell, J. L. Acta Cryst. C 1995, 51, 2651-2652.
https://doi.org/10.1107/S0108270195009474
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