European Journal of Chemistry

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

Article Sidebar

PDF CIF FILE
Published: Dec 31, 2017
DOI: https://doi.org/10.5155/eurjchem.8.4.410-416.1650
Keywords:
Thiourea derivative, Antimicrobial activity, Single crystal structure, Molecular self-assembly, Hirshfeld surface analysis, Deformation electron density
Section
Research Article
Issue
Vol. 8 No. 4 (2017): December 2017
Dates
Received 2017-10-20
Accepted 2017-11-09
Published 2017-12-31
Crossmark


Main Article Content

Ilkay Gumus
Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
https://orcid.org/0000-0002-9398-0057
Serpil Gonca
Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Mersin University, Mersin, TR 33343, Turkey
https://orcid.org/0000-0002-8544-1184
Birdal Arslan
Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
https://orcid.org/0000-0002-6345-0514
Ebru Keskin
Advanced Technology Research and Application Center, Mersin University, Mersin, TR 33343, Turkey
https://orcid.org/0000-0002-3130-941X
Ummuhan Solmaz
Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
https://orcid.org/0000-0002-3697-577X
Hakan Arslan
Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
http://orcid.org/0000-0003-0046-9442

Abstract

The compound N-(dibenzylcarbamothioyl)-3-methylbutanamide as a thiourea derivative was synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound was also characterized by single crystal X-ray diffraction method. Crystal data for title compound C20H24N2OS: monoclinic, space group C2/c (no. 15), a = 19.6882(9) Å, b = 9.4045(4) Å, c = 19.5012(8) Å, β = 98.433(2)°, V = 3571.8(3) Å3, Z = 8, μ(CuKα) = 1.665 mm-1, 25057 reflections measured (9.168° ≤ 2Θ ≤ 144.196°), 3500 unique (Rint = 0.0322, Rsigma = 0.0200) which were used in all calculations. The final R1 was 0.0363 (I>2σ(I)) and wR2 was 0.0910 (all data). Intermolecular contacts obtained from X-ray single crystal diffraction study were also explored using both Hirshfeld surfaces and fingerprint plots. Hirshfeld surface analysis showed the occurrence of S···H, O···H and H···H contacts that display an important role to crystal packing stabilization of the thiourea derivative compound. In addition, the compound was evaluated for both their in-vitro antibacterial and antifungal activity.


icon graph This Abstract was viewed 2556 times | icon graph Article PDF downloaded 763 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Gumus, I.; Gonca, S.; Arslan, B.; Keskin, E.; Solmaz, U.; Arslan, H. N-(Dibenzylcarbamothioyl)-3-Methylbutanamide: Crystal Structure, Hirshfeld Surfaces and Antimicrobial Activity. Eur. J. Chem. 2017, 8, 410-416.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Mushtaque, M.; Jahan, M.; Ali, M.; M. S. Khan; Khan, M. S.; Sahay, P.; Kesarwani, A. J. Mol. Struc. 2016, 1122, 164-174.
https://doi.org/10.1016/j.molstruc.2016.05.087

[2]. Kodomari, M.; Suzuki, M.; Tanigawa, K.; Aoyama, T. Tetrahedron Lett. 2005, 46, 5841-5843.
https://doi.org/10.1016/j.tetlet.2005.06.135

[3]. Lesyk, R.; Zimenkovsky, B.; Curr. Org. Chem. 2004, 8, 1547-1577.
https://doi.org/10.2174/1385272043369773

[4]. Lesyk, R.; Vladzimirska, O.; Holota, S.; Zaprutko, L.; Gzella, A. Eur. J. Med. Chem. 2007, 42, 641-648.
https://doi.org/10.1016/j.ejmech.2006.12.006

[5]. Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Zaprutko, L.; Gzella, A.; Lesyk, R. Eur. J. Med. Chem. 2009, 44, 1396-1404.
https://doi.org/10.1016/j.ejmech.2008.09.032

[6]. Mushtaque, M.; Avecilla, F.; Khan, M. S.; Hafeez, Z. B.; Rezvi, M. M. A.; Srivastava, A. J. Mol. Struc. 2017, 1141, 119-132.
https://doi.org/10.1016/j.molstruc.2017.03.066

[7]. Gomes, L. R.; Santos, L. M. N. B. F.; Coutinho, J. A. P.; Schroder, B.; Low, J. N. Acta Crystallogr. E 2010, 66, o870-o870.
https://doi.org/10.1107/S1600536810009578

[8]. Saeed, A.; Florke, U. Acta Crystallogr. E 2006, 62, o2403-o2405.
https://doi.org/10.1107/S1600536806018319

[9]. Janiak, C. J. Chem. Soc. Dalton Trans. 2000, 3885-3896.
https://doi.org/10.1039/b003010o

[10]. Seth, S. K.; Manna, P.; Singh, N. J.; Mitra, M.; Jana, A. D.; Das, A.; Choudhury, S. R.; Kar, T.; Mukhopadhyay S.; Kim, K. S. Cryst. Eng. Comm. 2013, 15, 1285-1288.
https://doi.org/10.1039/c2ce26577j

[11]. Habtu, M. M.; Bourne, S. A.; Koch, K. R.; Luckay, R. C. New J. Chem. 2006, 30, 155-162.
https://doi.org/10.1039/b603802f

[12]. Saeed, A.; Bolte, M.; Erben, M. F.; Perez, H. Cryst. Eng. Comm. 2015, 17, 7551-7563.
https://doi.org/10.1039/C5CE01373A

[13]. Weiqun, Z.; Wen, Y.; Liqun, X.; Xianchen, C. J. Inorg. Biochem. 2005, 99, 1314-1319.
https://doi.org/10.1016/j.jinorgbio.2005.03.004

[14]. Yang, W.; Liu, H.; Li, M.; Wang, F.; Zhou, W.; Fan, J. J. Inorg. Biochem. 2012, 116, 97-105.
https://doi.org/10.1016/j.jinorgbio.2012.08.001

[15]. Selvakumaran, N.; Pratheepkumar, A.; Ng, S. W.; Tiekink, E. R. T.; Karvembu, R. Inorg. Chim. Acta 2013, 404, 82-87.
https://doi.org/10.1016/j.ica.2013.04.024

[16]. Yesilkaynak, T.; Binzet, G.; Emen, F. M.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2010, 1(1), 1-5.
https://doi.org/10.5155/eurjchem.1.1.1-5.3

[17]. Saeed, A.; Mumtaz, A.; Florke, U. Eur. J. Chem. 2010, 1(2), 73-75.
https://doi.org/10.5155/eurjchem.1.2.73-75.34

[18]. Gumus, I.; Solmaz, U.; Celik, O.; Binzet, G.; Balci, K. G.; Arslan, H. Eur. J. Chem. 2015, 6(3), 237-241.
https://doi.org/10.5155/eurjchem.6.3.237-241.1265

[19]. Saeed, S.; Rashid, N.; Jones, P.; Hussain, R. Eur. J. Chem. 2011, 2(1), 77-82.
https://doi.org/10.5155/eurjchem.2.1.77-82.183

[20]. Saeed, S.; Rashid, N.; Ali, M.; Hussain, R.; Jones, G. P. Eur. J. Chem. 2010, 1(3), 221-227.
https://doi.org/10.5155/eurjchem.1.3.221-227.124

[21]. Binzet, G.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2012, 3(1), 37-39.
https://doi.org/10.5155/eurjchem.3.1.37-39.591

[22]. Binzet, G.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2012, 3(2), 211-213.
https://doi.org/10.5155/eurjchem.3.2.211-213.594

[23]. Egan, T. J.; Koch, K. R.; Swan, P. L.; Clarkson, C.; Van Schalkwyk, D. A.; Smith, P. J. J. Med. Chem. 2004, 47, 2926-2934.
https://doi.org/10.1021/jm031132g

[24]. Gunasekaran, N.; Bhuvanesh, N. S. P.; Karvembu, R. Polyhedron 2017, 122, 39-45.
https://doi.org/10.1016/j.poly.2016.10.038

[25]. Ferreira, F. F.; Trindade, A. C.; Antonio, S. G.; De Oliveira Paiva-Santos, C. Cryst. Eng. Comm. 2011, 13, 5474-5479.
https://doi.org/10.1039/c1ce05362k

[26]. Yamin, B. M.; Osman, U. M. Acta Crystallogr. E 2011, 67, o1286-o1286.
https://doi.org/10.1107/S1600536811014954

[27]. Zhu, W.; Yang, W.; Zhou, W.; Liu, H.; Wei, S.; Fan, J. J. Mol. Struct. 2011, 1004, 74-81.
https://doi.org/10.1016/j.molstruc.2011.07.028

[28]. Sun, J.; Cai, S.; Mei, H.; Li, J.; Yan, N.; Wang, Q.; Lin, Z.; Huo, D. Chem. Biol. Drug Des. 2010, 76(3), 245-254.

[29]. Saeed, A.; Khurshid, A.; Bolte, M.; Fantoni, A. C.; Erben, M. F. Spectrochim. Acta A 2015, 143, 59-66.
https://doi.org/10.1016/j.saa.2015.02.042

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

[31]. Palatinus, L.; Chapuis, G. J. Appl. Cryst. 2007, 40, 786-790.
https://doi.org/10.1107/S0021889807029238

[32]. Palatinus, L.; van der Lee, A. J. Appl. Cryst. 2008, 41, 975-984.
https://doi.org/10.1107/S0021889808028185

[33]. Palatinus, L.; Prathapa, S. J.; van Smaalen, S. J. Appl. Cryst. 2012, 45, 575-580.
https://doi.org/10.1107/S0021889812016068

[34]. Sheldrick, G. M. Acta Crystallogr. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[35]. Douglass, I. B.; Dains, F. B. J. Am. Chem. Soc. 1934, 56, 719-721.
https://doi.org/10.1021/ja01318a057

[36]. Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer 17, University of Western Australia, 2017.

[37]. Burlesson, F. G.; Chambers, T. M.; Wedbrauk, D. L. Virology. A Laboratory Manual, Academic Press, New York, 1992.

[38]. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved standard NCCLS document M27-A. National Committee for Clinical Laboratory Standards, Wayne, Pa., 2002.

[39]. Yusof, M. S. M.; Jusoh, R. H.; Khairul, W. M.; Yamin, B. M. J. Mol. Struct. 2010, 975, 280-284
https://doi.org/10.1016/j.molstruc.2010.04.037

[40]. Rauf, M. K.; Ebihara, M.; Badshah, A. Acta Crystallogr. E 2012, 68, o119-o119.
https://doi.org/10.1107/S1600536811052780

[41]. Yang, W.; Zhou, W. Q.; Zhang, Z. J. J. Mol. Struct. 2007, 828, 46-53.
https://doi.org/10.1016/j.molstruc.2006.05.033

[42]. Arslan, H.; Florke, U.; Kulcu, N.; Binzet, G. Spectrochim. Acta A 2007, 68, 1347-1355.
https://doi.org/10.1016/j.saa.2007.02.015

[43]. Yusof, M. S.; Jusoh, R. H.; Khairul, W. M.; Bohari, M. Y. J. Mol. Struct. 2010, 975, 280-284.
https://doi.org/10.1016/j.molstruc.2010.04.037

[44]. Al-Abbasi, A. A.; Yamin, B. M.; Kassim, M. B. Acta Crystallogr. E 2011, 67, 1891-1894.
https://doi.org/10.1107/S1600536811025013

[45]. Mohamadou, A.; Dechamps-Olivier, I.; Barbier, J. P. Polyhedron 1994, 13, 1363-1370.
https://doi.org/10.1016/S0277-5387(00)81702-7

[46]. Arslan, H.; Florke, U.; Kulcu. N. Acta Chim. Slov. 2004, 51, 787-792.

[47]. Spackman, M. A.; Jayatilaka, D. Cryst. Eng. Comm. 2009, 11, 19-32.
https://doi.org/10.1039/B818330A

[48]. Spackman, M. A.; McKinnon, J. J. Cryst. Eng. Comm. 2002, 4, 378-392.
https://doi.org/10.1039/B203191B

[49]. McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. 2007, 37, 3814-3816
https://doi.org/10.1039/b704980c

[50]. Angeloski, A.; Hook, J. M.; Bhadbhade, M.; Baker, A. T.; McDonagh, A. M. Cryst. Eng. Comm. 2016, 18, 7070-7077.
https://doi.org/10.1039/C6CE01475E

[51]. Sarkar, S.; Pavan, M. S.; Row, T. N. G. Phys. Chem. Chem. Phys. 2015, 17, 2330-2334.
https://doi.org/10.1039/C4CP04690K

Supporting Agencies

This work was supported by Mersin University Research Fund [Project No, 2016-AP4-1426].
Most read articles by the same author(s)

Most read articles by the same author(s)

1 2 3 4 5 6 7 8 9 10 > >> 
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

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 https://www.eurjchem.com/index.php/eurjchem/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 (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).