Abstract
C18H16Cl2N4O2S, monoclinic, P21/c (no. 14), a = 9.1950(5) Å, b = 23.9750(13) Å, c = 9.5514(5) Å, β = 111.136(2)°, V = 1963.96(18) Å3, Z = 4, Rgt(F) = 0.0516, wRref(F2) = 0.139, T = 296 K.
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Zeitschrift für Kristallographie - New Crystal Structures
Editor-in-Chief: Huppertz, Hubert
Ed. by Reiß, Guido
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Crystal structure of 5-(2-chloro-5-nitrophenyl)-3-(4-chlorophenyl)-N-ethyl-4,5-dihydro-1H-pyrazole-1-carbothioamide, C18H16Cl2N4O2S
Published Online: 2016-08-15 | DOI: https://doi.org/10.1515/ncrs-2016-0109
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1459025
The crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.
Table 1:
Data collection and handling.
Table 2
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Source of material
The title compound was synthesized from reaction of 5-(2-chloro-5-nitrophenyl)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazole with ethyl isothiocyanate in dry ethanol for 2 h under reflux condition. The solid produced was filtered, dried and recrystallized from dimethylformamide to give colourless crystals of the title compound (Mp. 207 °C).
Discussion
Compounds possessing pyrazoline ring systems are an important class of heterocycles. Recently, various pyrazoline containing materials with interesting properties were synthesized [1, 2, 3, 4]. They have significant biological activities including antimicrobial, anticonvulsant and antiviral [5, 6, 8, 9].
The asymmetric unit of the title structure contains one molecule, in which the phenyl ring (C10—C15) is highly deviated from the whole molecule plane and makes a dihedral angle of 78.74(3)° with the pyrazol ring (N1—N2—C7—C8—C9). The packing shows four potential hydrogen bonds: N4—H1N4⋯S1i, C8—H8A⋯O1ii, C8—H8B⋯Cl1iii and C18—H18C⋯N1iv with symmetry code: (i) x, −y + 3/2, z − 1/2; (ii) −x + 1, −y + 1, −z + 1; (iii) x, y, z + 1; (iv) x, −y + 3/2, z + 1/2.
Acknowledgements:
The authors extend their appreciation to the College of Applied Medical Sciences Research Centre and the Deanship of Scientific Research at King Saud University for their funding of this research.
References
- 1.
Badavath, V. N.; Baysal, I.; Ucar, G.; Sinha, B. N.; Jayaprakash, V.: Monoamine oxidase inhibitory activity of novel pyrazoline analogues: curcumin based design and synthesis. ACS Med. Chem. Lett. 7 (2016) 56–61. Google Scholar
- 2.
Szukalski, A.; Haupa, K.; Miniewicz, A.; Mysliwiec, J.: Photoinduced birefringence in PMMA polymer doped with photoisomerizable pyrazoline derivative. J. Phys. Chem. C 119 (2015) 10007–10014. Google Scholar
- 3.
Lederhose, P.; Haworth, N. L.; Thomas, K.; Bottle, S. E.; Coote, M. L.; Barner-Kowollik, C.; Blinco, J. P.: Design of redox/radical sensing molecules via nitrile imine-mediated tetrazole-ene cycloaddition (NITEC). J. Org. Chem. 80 (2015) 8009–8017.Google Scholar
- 4.
Duan, X.-Y.; Yang, X.-L.; Jia, P.-P.; Zhang, M.; Han, B.: Hydrazonyl radical-participated tandem reaction: a strategy for the synthesis of pyrazoline-functionalized oxindoles. Org. Lett. 17 (2015) 6022–6025. Google Scholar
- 5.
Karad, S. C.; Purohit, V. B.; Thakor, P.; Thakkar, V. R.; Raval, D. K.: Novel morpholinoquinoline nucleus clubbed with pyrazoline scaffolds: Synthesis, antibacterial, antitubercular and antimalarial activities. Eur. J. Med. Chem. 112 (2016) 270–279. Google Scholar
- 6.
Viveka, S.; Shama, P.; Nagaraja, G. K.; Ballav, S.; Kerkar, S.: Design and synthesis of some new pyrazolyl-pyrazolines as potential anti-inflammatory, analgesic and antibacterial agents. Eur. J. Med. Chem. 101 (2015) 442–451.Google Scholar
- 7.
Abdel-Wahab, B. F.; Mohamed, H. A.; Ali, M. M.: Synthesis and in vitro cytotoxicity of new 3-(5-methyl-1-aryl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazoles. J. Modern Med. Chem. 3 (2015) 9–15.Google Scholar
- 8.
Bano, S.; Alam, M. S.; Javed, K.; Dudeja, M.; Das, A. K.; Dhulap, A.: Synthesis, biological evaluation and molecular docking of some substituted pyrazolines and isoxazolines as potential antimicrobial agents. Eur. J. Med. Chem. 95 (2015) 96–103.Google Scholar
- 9.
Kumar, S.; Bawa, S.; Drabu, S.; Kumar, R.; Gupta, H.: Biological activities of pyrazoline derivatives − a recent development. Recent Pat. Antiinfect. Drug Discov. 4 (2009) 154–163. Google Scholar
- 10.
Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122. Google Scholar
- 11.
Sheldrick, G. M.: SHELXTL-PC (Version 5.1), Siemens Analytical Instruments, Inc., Madison, WI, 1997. Google Scholar
- 12.
Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA, 2009. Google Scholar
About the article
Received: 2016-05-25
Accepted: 2016-08-01
Published Online: 2016-08-15
Published in Print: 2016-12-01
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 231, Issue 4, Pages 1169–1170, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0109.
©2016 Gamal A. El-Hiti et al., published by De Gruyter.. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0
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