European Journal of Chemistry

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


Main Article Content

Ilkay Gumus
Serpil Gonca
Birdal Arslan
Ebru Keskin
Ummuhan Solmaz
Hakan Arslan


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.

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How to Cite
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.

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[1]. Mushtaque, M.; Jahan, M.; Ali, M.; M. S. Khan; Khan, M. S.; Sahay, P.; Kesarwani, A. J. Mol. Struc. 2016, 1122, 164-174.

[2]. Kodomari, M.; Suzuki, M.; Tanigawa, K.; Aoyama, T. Tetrahedron Lett. 2005, 46, 5841-5843.

[3]. Lesyk, R.; Zimenkovsky, B.; Curr. Org. Chem. 2004, 8, 1547-1577.

[4]. Lesyk, R.; Vladzimirska, O.; Holota, S.; Zaprutko, L.; Gzella, A. Eur. J. Med. Chem. 2007, 42, 641-648.

[5]. Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Zaprutko, L.; Gzella, A.; Lesyk, R. Eur. J. Med. Chem. 2009, 44, 1396-1404.

[6]. Mushtaque, M.; Avecilla, F.; Khan, M. S.; Hafeez, Z. B.; Rezvi, M. M. A.; Srivastava, A. J. Mol. Struc. 2017, 1141, 119-132.

[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.

[8]. Saeed, A.; Florke, U. Acta Crystallogr. E 2006, 62, o2403-o2405.

[9]. Janiak, C. J. Chem. Soc. Dalton Trans. 2000, 3885-3896.

[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.

[11]. Habtu, M. M.; Bourne, S. A.; Koch, K. R.; Luckay, R. C. New J. Chem. 2006, 30, 155-162.

[12]. Saeed, A.; Bolte, M.; Erben, M. F.; Perez, H. Cryst. Eng. Comm. 2015, 17, 7551-7563.

[13]. Weiqun, Z.; Wen, Y.; Liqun, X.; Xianchen, C. J. Inorg. Biochem. 2005, 99, 1314-1319.

[14]. Yang, W.; Liu, H.; Li, M.; Wang, F.; Zhou, W.; Fan, J. J. Inorg. Biochem. 2012, 116, 97-105.

[15]. Selvakumaran, N.; Pratheepkumar, A.; Ng, S. W.; Tiekink, E. R. T.; Karvembu, R. Inorg. Chim. Acta 2013, 404, 82-87.

[16]. Yesilkaynak, T.; Binzet, G.; Emen, F. M.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2010, 1(1), 1-5.

[17]. Saeed, A.; Mumtaz, A.; Florke, U. Eur. J. Chem. 2010, 1(2), 73-75.

[18]. Gumus, I.; Solmaz, U.; Celik, O.; Binzet, G.; Balci, K. G.; Arslan, H. Eur. J. Chem. 2015, 6(3), 237-241.

[19]. Saeed, S.; Rashid, N.; Jones, P.; Hussain, R. Eur. J. Chem. 2011, 2(1), 77-82.

[20]. Saeed, S.; Rashid, N.; Ali, M.; Hussain, R.; Jones, G. P. Eur. J. Chem. 2010, 1(3), 221-227.

[21]. Binzet, G.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2012, 3(1), 37-39.

[22]. Binzet, G.; Florke, U.; Kulcu, N.; Arslan, H. Eur. J. Chem. 2012, 3(2), 211-213.

[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.

[24]. Gunasekaran, N.; Bhuvanesh, N. S. P.; Karvembu, R. Polyhedron 2017, 122, 39-45.

[25]. Ferreira, F. F.; Trindade, A. C.; Antonio, S. G.; De Oliveira Paiva-Santos, C. Cryst. Eng. Comm. 2011, 13, 5474-5479.

[26]. Yamin, B. M.; Osman, U. M. Acta Crystallogr. E 2011, 67, o1286-o1286.

[27]. Zhu, W.; Yang, W.; Zhou, W.; Liu, H.; Wei, S.; Fan, J. J. Mol. Struct. 2011, 1004, 74-81.

[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.

[30]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42, 339-341.

[31]. Palatinus, L.; Chapuis, G. J. Appl. Cryst. 2007, 40, 786-790.

[32]. Palatinus, L.; van der Lee, A. J. Appl. Cryst. 2008, 41, 975-984.

[33]. Palatinus, L.; Prathapa, S. J.; van Smaalen, S. J. Appl. Cryst. 2012, 45, 575-580.

[34]. Sheldrick, G. M. Acta Crystallogr. C 2015, 71, 3-8.

[35]. Douglass, I. B.; Dains, F. B. J. Am. Chem. Soc. 1934, 56, 719-721.

[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

[40]. Rauf, M. K.; Ebihara, M.; Badshah, A. Acta Crystallogr. E 2012, 68, o119-o119.

[41]. Yang, W.; Zhou, W. Q.; Zhang, Z. J. J. Mol. Struct. 2007, 828, 46-53.

[42]. Arslan, H.; Florke, U.; Kulcu, N.; Binzet, G. Spectrochim. Acta A 2007, 68, 1347-1355.

[43]. Yusof, M. S.; Jusoh, R. H.; Khairul, W. M.; Bohari, M. Y. J. Mol. Struct. 2010, 975, 280-284.

[44]. Al-Abbasi, A. A.; Yamin, B. M.; Kassim, M. B. Acta Crystallogr. E 2011, 67, 1891-1894.

[45]. Mohamadou, A.; Dechamps-Olivier, I.; Barbier, J. P. Polyhedron 1994, 13, 1363-1370.

[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.

[48]. Spackman, M. A.; McKinnon, J. J. Cryst. Eng. Comm. 2002, 4, 378-392.

[49]. McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. 2007, 37, 3814-3816

[50]. Angeloski, A.; Hook, J. M.; Bhadbhade, M.; Baker, A. T.; McDonagh, A. M. Cryst. Eng. Comm. 2016, 18, 7070-7077.

[51]. Sarkar, S.; Pavan, M. S.; Row, T. N. G. Phys. Chem. Chem. Phys. 2015, 17, 2330-2334.

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