

Structural characterization and crystal packing of the isoquinoline derivative
Viktor Vrabel (1)





(1) Institute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
(2) Institute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
(3) Institute of Mathematics and Physics, Faculty of Mechanical Engineering, Slovak University of Technology in Bratislava, Námestie slobody 17, SK-812 31 Bratislava, Slovak Republic
(4) Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
(5) Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
(*) Corresponding Author
Received: 07 Jun 2018 | Revised: 30 Jun 2018 | Accepted: 08 Jul 2018 | Published: 30 Sep 2018 | Issue Date: September 2018
Abstract
We report the crystal and molecular structure of a new isoquinoline-derivative, namely methyl O-[(11R, 11aS)-4-oxo-1, 3, 4, 6, 11, 11a-hexahydro-2H-pyrido[1, 2-b]isoquinolin-11-yl]carbonodithioate (I), C15H17NO2S2, which crystallizes in the non-centrosymmetric space group P212121 and its absolute structure was confirmed by anomalous dispersion effects in diffraction measurements on the crystals. Two central six-membered heterocyclic rings adopt a distorted half-chair conformation. The molecules are linked by a combination of weak C—H∙∙∙O, C—H∙∙∙S, C—H∙∙∙p inter- and intra-molecular interactions resulting in a three-dimensional network in the crystal structure. Crystal Data for C15H17NO2S2 (M =307.41 g/mol): orthorhombic, space group P212121 (no. 19), a = 5.2804(5) Å, b = 8.1347(17) Å, c = 35.015(4) Å, V = 1504.1(4) Å3, Z = 4, T = 298(2) K, μ(MoKα) = 0.354 mm-1, Dcalc =1.358 g/cm3, 20270 reflections measured (5.522° ≤ 2Θ ≤ 50.69°), 2757 unique (Rint = 0.0346, Rsigma = 0.0203) which were used in all calculations. The final R1 was 0.0389 (I > 2σ(I)) and wR2 was 0.0965 (all data).
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.9.3.189-193.1758
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Funding information
The Slovak Research and Development Agency (APVV 0204-10) and the Grant Agency of the Slovak Republic (VEGA 1/0873/15, VEGA 1/0371/16 and KEGA 035STU-4/2017).
References
[1]. Mansour, A. M.; Hassaneen, H. M.; Mohammed, Y. Sh.; Abdel-Ghani, N. T. J. Mol. Struct. 2013, 1045, 180-190.
https://doi.org/10.1016/j.molstruc.2013.04.032
[2]. Kidwai, M.; Bhushan, K. R.; Sapra, P.; Saxena, R. K.; Gupta, R. Bioorg. Med. Chem. Lett. 2000, 8, 69‐72.
https://doi.org/10.1016/S0968-0896(99)00256-4
[3]. Strekowski, L.; Mokrosz, J. L.; Honkan, V. A.; Czarxy, A.; Ceyla, M. T.; Wydra, R. L.; Patterson, S. E.; Schinazi, R. F. J. Med. Chem. 1991, 34, 1739‐1746.
https://doi.org/10.1021/jm00109a031
[4]. Bray, P. G.; Hawley, S. R.; Ward, S. A. Mol. Pharmacol. 1996, 50, 1551‐1558.
[5]. Sparatore, A.; Basilico, N.; Casagrande, M.; Parapini, S.; Taramelli, D.; Brun, R.; Wittlin, S.; Sparatore, F. Bioorg. Med. Chem. Lett. 2008, 18, 3737‐3740.
https://doi.org/10.1016/j.bmcl.2008.05.042
[6]. Sweeney, A. W.; Blackburn, C. R. B.; Rieckmann, K. H. Am. J. Trop. Med. Hyg. 2004, 71, 187‐189.
[7]. Deady, L. W.; Desneres, J.; Kaye, A. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. Bioorg. Med. Chem. 2001, 9, 445‐452.
https://doi.org/10.1016/S0968-0896(00)00264-9
[8]. Khan, K. M.; Zaify, Z. S.; Khan, Z. A. Drug Res. 2000, 50, 915‐922.
[9]. Abuelizz, H. A.; Al-Salahi, R.; Al-Asri, J.; Mortier, J.; Marzouk, M.; Ezzeldin, E.; Ali, A. A.; Khalil, M. G.; Hazem, G. W.; Ghabbour, A.; Almehizia, A. A.; Abdel-Jaleel, G. A. Chem. Cent. J. 2017, 11, 103, 1-14.
[10]. Griffith, K. S.; Lewis, L. S.; Mali, S.; Parise, M. E. JAMA 2007, 297(20), 2264‐2277.
https://doi.org/10.1001/jama.297.20.2264
[11]. Yasukawa, K.; Takido, M.; Ikekawa, T.; Shimada, F.; Takeuchi, M.; Nakagawa, S. Chem. Pharm. Bull. 1991, 39, 1462‐1465.
https://doi.org/10.1248/cpb.39.1462
[12]. Werbel, L. M.; Angelo, M.; Fry, D. W.; Worth, D. F. J. Med. Chem. 1986, 29, 1321‐1322.
https://doi.org/10.1021/jm00157a040
[13]. Pagac, T.; Safar, P.; Marchalin, S.; Jezikova, Z.; Balonova, B.; Supolikova, M.; Novakova, E.; Kubickova, J.; Soral, M.; Sivy, J.; Olejnikova. P. Monatsh. Chem. 2018, in press accepted.
[14]. Oxford Diffraction 2009, CrysAlisPro. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
[15]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112‐122.
https://doi.org/10.1107/S0108767307043930
[16]. Brandenburg, K. 2001, DIAMOND. Crystal Impact GbR, Bonn, Germany.
[17]. Allen, F. H.; Johnson, O.; Shields, G. P.; Smith, B. R.; Towler, M. J. Appl. Cryst. 2004, 37, 335‐338.
https://doi.org/10.1107/S0021889804003528
[18]. Spek, A. L. Acta Cryst. 2009, D65, 148‐155.
[19]. Farrugia, L. J. J. Appl. Cryst. 1997, 30, 565-565.
https://doi.org/10.1107/S0021889897003117
[20]. Clark, R. C.; Reid, J. S. Acta Cryst. 1995, A51, 887-897.
https://doi.org/10.1107/S0108767395007367
[21]. Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354‐1362.
https://doi.org/10.1021/ja00839a011
[22]. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555‐1573.
https://doi.org/10.1002/anie.199515551
Supporting information
The Supplementary Material for this article can be found online at: Supplementary files
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.9.3.189-193.1758

















European Journal of Chemistry 2018, 9(3), 189-193 | doi: https://doi.org/10.5155/eurjchem.9.3.189-193.1758 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c) 2018 Authors

This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). 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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.