European Journal of Chemistry 2018, 9(4), 347-352. doi:10.5155/eurjchem.9.4.347-352.1782

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


Abdullah Aydin (1,*) orcid , Mehmet Akkurt (2) orcid , Zehra Tugce Gur (3) orcid , Erden Banoglu (4) orcid

(1) Department of Mathematics and Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey
(2) Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
(3) Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey
(4) Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey
(*) Corresponding Author

Received: 18 Aug 2018, Accepted: 18 Sep 2018, Published: 31 Dec 2018

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).


Keywords


Pyrazole ring; Crystal structure; Anticancer activity; C—H···π interactions; Hirshfeld surface analysis; Antimycobacterial activity

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DOI: 10.5155/eurjchem.9.4.347-352.1782

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How to cite


Aydin, A.; Akkurt, M.; Gur, Z.; Banoglu, E. Eur. J. Chem. 2018, 9(4), 347-352. doi:10.5155/eurjchem.9.4.347-352.1782
Aydin, A.; Akkurt, M.; Gur, Z.; 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(4), 347-352. doi:10.5155/eurjchem.9.4.347-352.1782
Aydin, A., Akkurt, M., Gur, Z., & Banoglu, E. (2018). Crystal structure and Hirshfeld surface analysis of methyl 1-(2,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxylate. European Journal of Chemistry, 9(4), 347-352. doi:10.5155/eurjchem.9.4.347-352.1782
Aydin, Abdullah, Mehmet Akkurt, Zehra Tugce Gur, & Erden Banoglu. "Crystal structure and Hirshfeld surface analysis of methyl 1-(2,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxylate." European Journal of Chemistry [Online], 9.4 (2018): 347-352. Web. 15 Nov. 2019
Aydin, Abdullah, Akkurt, Mehmet, Gur, Zehra, AND Banoglu, Erden. "Crystal structure and Hirshfeld surface analysis of methyl 1-(2,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxylate" European Journal of Chemistry [Online], Volume 9 Number 4 (31 December 2018)

DOI Link: https://doi.org/10.5155/eurjchem.9.4.347-352.1782

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