European Journal of Chemistry 2017, 8(4), 410-416. doi:10.5155/eurjchem.8.4.410-416.1650

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


Ilkay Gumus (1,*) orcid , Serpil Gonca (2) orcid , Birdal Arslan (3) orcid , Ebru Keskin (4) orcid , Ummuhan Solmaz (5) orcid , Hakan Arslan (6) orcid

(1) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(2) Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Mersin University, Mersin, TR 33343, Turkey
(3) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(4) Advanced Technology Research and Application Center, Mersin University, Mersin, TR 33343, Turkey
(5) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(6) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(*) Corresponding Author

Received: 20 Oct 2017, Accepted: 09 Nov 2017, Published: 31 Dec 2017

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)°, = 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.


Keywords


Thiourea derivative; Antimicrobial activity; Single crystal structure; Molecular self-assembly; Hirshfeld surface analysis; Deformation electron density

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DOI: 10.5155/eurjchem.8.4.410-416.1650

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Citations

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[1]. Gun Binzet, Ersan Turunc, Ulrich Flörke, Nevzat Külcü, Hakan Arslan
Crystal Structure and Cyclic Voltammetric Studies on the Metal Complexes of N-(Dimethylcarbamothioyl)-4-fluorobenzamide
Journal of Chemistry  2018, 1, 2018
DOI: 10.1155/2018/6108242
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[2]. Ilkay Gumus, Ummuhan Solmaz, Gun Binzet, Ebru Keskin, Birdal Arslan, Hakan Arslan
Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis
Research on Chemical Intermediates  , , 2018
DOI: 10.1007/s11164-018-3596-5
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[3]. Ebru Keskin, Ummuhan Solmaz, Gun Binzet, Ilkay Gumus, Hakan Arslan
Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands
European Journal of Chemistry  9(4), 360, 2018
DOI: 10.5155/eurjchem.9.4.360-368.1774
/


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


How to cite


Gumus, I.; Gonca, S.; Arslan, B.; Keskin, E.; Solmaz, U.; Arslan, H. Eur. J. Chem. 2017, 8(4), 410-416. doi:10.5155/eurjchem.8.4.410-416.1650
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(4), 410-416. doi:10.5155/eurjchem.8.4.410-416.1650
Gumus, I., Gonca, S., Arslan, B., Keskin, E., Solmaz, U., & Arslan, H. (2017). N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity. European Journal of Chemistry, 8(4), 410-416. doi:10.5155/eurjchem.8.4.410-416.1650
Gumus, Ilkay, Serpil Gonca, Birdal Arslan, Ebru Keskin, Ummuhan Solmaz, & Hakan Arslan. "N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity." European Journal of Chemistry [Online], 8.4 (2017): 410-416. Web. 18 Jan. 2019
Gumus, Ilkay, Gonca, Serpil, Arslan, Birdal, Keskin, Ebru, Solmaz, Ummuhan, AND Arslan, Hakan. "N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

DOI Link: https://doi.org/10.5155/eurjchem.8.4.410-416.1650

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