European Journal of Chemistry

Crystal structure and Hirshfeld surface analysis of methyl 1-(2,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxylate

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Abdullah Aydin
Mehmet Akkurt
Zehra Tugce Gur
Erden Banoglu

Abstract

The title compound, C13H12Cl2N2O2, crystallizes with six molecules in the asymmetric unit, such that, the 1H-pyrazole rings are essentially planar. The six molecules are stabilized by intramolecular C-H···N and C-H···Cl interactions and the crystal structure is stabilized by intermolecular C-H···O hydrogen bonds, forming molecular sheets into paralel to the (-1 1 0) plane. These sheets are connected to each other by C-H···O hydrogen bonds and C-H···π interactions. In the Hirshfeld surface analysis, the H···H, Cl···H/H···Cl, C···H/H···C, O···H/H···O, N···H/H···N, Cl···Cl, Cl···O/O···Cl interactions add to 95.8% of the intermolecular contacts of the Hirshfeld surface area. The remaining contributions (2.9%) correspond to Cl···C/C···Cl, C···O/O···C, O···O and N···N interactions. Crystal Data for C13H12Cl2N2O2 (= 299.15 g/mol): Triclinic, space group P-1 (no. 2), a = 12.0505(10) Å, b = 12.3189(11) Å, c = 29.184(3) Å, α = 88.565(4)°, β = 89.296(4)°, γ = 76.833(4)°, = 4217.0(7) Å3, Z = 12, T = 296(2) K, μ(MoKα) = 0.460 mm-1, Dcalc = 1.414 g/cm3, 83073 reflections measured (2.8° ≤ 2Θ ≤ 47°), 12426 unique (Rint = 0.0411, Rsigma = 0.0235) which were used in all calculations. The final R1 was 0.0662 (I > 2σ(I)) and wR2 was 0.2481 (all data).


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Aydin, A.; Akkurt, M.; Gur, Z. T.; Banoglu, E. Crystal Structure and Hirshfeld Surface Analysis of Methyl 1-(2,4-Dichlorobenzyl)-5-Methyl-1H-Pyrazole-3-Carboxylate. Eur. J. Chem. 2018, 9, 347-352.

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References

[1]. Kucukguzel, S. G.; Senkardes, S. Eur. J. Med. Chem. 2015, 97, 786-815.
https://doi.org/10.1016/j.ejmech.2014.11.059

[2]. Caliskan, B.; Yilmaz, A.; Evren, I.; Menevse, S.; Uludag, O.; Banoglu, E. Med. Chem. Res. 2013, 22, 782-793.
https://doi.org/10.1007/s00044-012-0072-4

[3]. Ding, X. L.; Zhang H. Y.; Qi, L.; Zhao, B. X.; Lv, H. S.; Miao, J. Y. Bioorg. Med. Chem. Lett. 2009, 19, 5325-5328.
https://doi.org/10.1016/j.bmcl.2009.07.131

[4]. Baraldi, P. G.; Beria, I.; Cozzi, P.; Geroni, C.; Espinosa, A.; Gallo, M. A.; Entrena, A.; Bingham, J. P.; John A. Hartley, J. A.; Romagnoli, R. Bioorg. & Med. Chem. 2004, 12(14), 3911-3921.
https://doi.org/10.1016/j.bmc.2004.04.045

[5]. Palaska, E.; Aydin, F.; Ucar, G.; Erol, D. Arch. Pharm. Chem. Life Sci. 2008, 341, 209-215.
https://doi.org/10.1002/ardp.200700159

[6]. Banoglu, E.; Akoglu, C.; Unlu, S.; Ergun, B. C.; Kupeli, E.; Yesilada, E.; Sahin, M. F. Arzneimittelforschung. 2005, 55(9), 520-527.

[7]. Sukuroglu, M.; Caliskan-Ergun, B.; Unlu, S.; Sahin, M. F.; Kupeli, E.; Yesilada, E.; Banoglu, E. Arch. Pharm. Res. 2005, 28(5), 509-517.
https://doi.org/10.1007/BF02977751

[8]. Ergun, B. C.; Nunez, M. T.; Labeaga, L.; Ledo, F.; Darlington, J.; Bain, G.; Cakir, B.; Banoglu, E. Arzneimittelforschung. 2010, 60(8), 497-505.

[9]. Caliskan, B.; Luderer, S.; Ozkan, Y.; Werz, O.; Banoglu E. Eur. J. Med. Chem. 2011, 46(10), 5021-5033.
https://doi.org/10.1016/j.ejmech.2011.08.009

[10]. Levent, S.; Calıskan, B.; Ciftci, M.; Ozkan, Y.; Yenicesu, I.; Unver, H.; Banoglu, E. Eur. J. Med. Chem. 2013, 64, 42-53.
https://doi.org/10.1016/j.ejmech.2013.03.048

[11]. Cankara-Pirol S.; Caliskan, B.; Durmaz, I.; Atalay, R.; Banoglu, E. Eur. J. Med. Chem. 2014, 87, 140-149.
https://doi.org/10.1016/j.ejmech.2014.09.056

[12]. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, 2007.

[13]. Sheldrick, G. M. Acta Cryst. A 2015, 71, 3-8.
https://doi.org/10.1107/S2053273314026370

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

[15]. Farrugia, L. J. J. Appl. Cryst. 2012, 45, 849-854.
https://doi.org/10.1107/S0021889812029111

[16]. Spek, A. L. Acta Cryst. D 2009, 65, 148-155.
https://doi.org/10.1107/S090744490804362X

[17]. Machado, P.; Campos, P. T.; Rosa, F. A.; Martins, M. A. P. Acta Cryst. E 2007, 63, o4741-o4741.
https://doi.org/10.1107/S1600536807057042

[18]. Sundar, T. V.; Parthasarathi, V.; Bolte, M.; Hunnur, R. K.; Badami, B. Acta Cryst. E 2005, 61, o3482-o3484.
https://doi.org/10.1107/S1600536805030448

[19]. Hirshfeld, H. L. Theor. Chim. Acta. 1977, 44, 129-138.
https://doi.org/10.1007/BF00549096

[20]. Spackman, M. A.; Jayatilaka, D. CrystEngComm. 2009, 11, 19-32.
https://doi.org/10.1039/B818330A

[21]. Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer17. The University of Western Australia, 2017.

[22]. Venkatesan, P.; Thamotharan, S.; Ilangovan, A.; Liang, H.; Sundius, T. Spectrochim. Acta A 2016, 153, 625-636.
https://doi.org/10.1016/j.saa.2015.09.002

[23]. Rohl, A. L.; Moret, M.; Kaminsky, W.; Claborn, K.; McKinnon, J. J.; Kahr, B. Cryst. Growth Des. 2008, 8, 4517-4525.
https://doi.org/10.1021/cg8005212

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