European Journal of Chemistry 2019, 10(3), 189-194. doi:10.5155/eurjchem.10.3.189-194.1903

Crystal structure and Hirshfeld surface analysis of N-(2-(N-methylsulfamoyl)phenyl)formamide: Degradation product of 2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide


Koffi Senam Etse (1,*) orcid , Guillermo Zaragoza (2) orcid , Bernard Pirotte (3) orcid

(1) Laboratory of Medicinal Chemistry, Center for Interdisciplinary Research on Medicines (CIRM), University of Liège, Quartier Hôpital B36 Av. Hippocrate 15 B-4000 Liège, Belgium
(2) Unidade de Difracción de Raios X, RIAIDT, Universidade de Santiago de Compostela, Campus VIDA, 15782 Santiago de Compostela, Spain
(3) Laboratory of Medicinal Chemistry, Center for Interdisciplinary Research on Medicines (CIRM), University of Liège, Quartier Hôpital B36 Av. Hippocrate 15 B-4000 Liège, Belgium
(*) Corresponding Author

Received: 03 Jun 2019, Accepted: 05 Jul 2019, Published: 30 Sep 2019

Abstract


The hydrolysis of 2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide (2) during crystallization under humidity (85 %) conditions, lead to N-(2-(N-methylsulfamoyl)phenyl)formamide as second step hydrolysis product, identified in the proposed degradation mechanism. Crystal of N-(2-(N-methylsulfamoyl)phenyl)formamide C8H10N2O3S (4), was obtained and characterized. The molecular structure determination was carried out with MoKα X-ray and data measured at 100 K. The compound 4 crystallizes in triclinic 1 space group with unit cell parameters a = 4.8465(4) Å, b = 8.1942(9) Å, c = 11.8686(13) Å, α = 77.080(4)°, β = 82.069(4)°, γ = 80.648(4)°, V = 450.76 (8) Å3 and Z = 2. The crystal structure is stabilized by intramolecular N-H···O and intermolecular C-H···O and N-H···O hydrogen bonds that extended as infinite 1D chain along [100]. Stabilization is also ensured by oxygen-π stacking interaction between the aromatic ring and oxygen of the sulfonamide group. The analysis of intermolecular interactions through the mapping of dnorm and shape-index revel that the most significant contributions to the Hirshfeld surface 40.6 and 33.9% are from H···H and O···H contacts, respectively.


Keywords


Hydrolysis; Formamide; Crystal structure; Hirshfeld surface; Benzothiadiazine; Hydrogen bonding

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DOI: 10.5155/eurjchem.10.3.189-194.1903

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How to cite


Etse, K.; Zaragoza, G.; Pirotte, B. Eur. J. Chem. 2019, 10(3), 189-194. doi:10.5155/eurjchem.10.3.189-194.1903
Etse, K.; Zaragoza, G.; Pirotte, B. Crystal structure and Hirshfeld surface analysis of N-(2-(N-methylsulfamoyl)phenyl)formamide: Degradation product of 2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide. Eur. J. Chem. 2019, 10(3), 189-194. doi:10.5155/eurjchem.10.3.189-194.1903
Etse, K., Zaragoza, G., & Pirotte, B. (2019). Crystal structure and Hirshfeld surface analysis of N-(2-(N-methylsulfamoyl)phenyl)formamide: Degradation product of 2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide. European Journal of Chemistry, 10(3), 189-194. doi:10.5155/eurjchem.10.3.189-194.1903
Etse, Koffi, Guillermo Zaragoza, & Bernard Pirotte. "Crystal structure and Hirshfeld surface analysis of N-(2-(N-methylsulfamoyl)phenyl)formamide: Degradation product of 2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide." European Journal of Chemistry [Online], 10.3 (2019): 189-194. Web. 23 Oct. 2019
Etse, Koffi, Zaragoza, Guillermo, AND Pirotte, Bernard. "Crystal structure and Hirshfeld surface analysis of N-(2-(N-methylsulfamoyl)phenyl)formamide: Degradation product of 2-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide" European Journal of Chemistry [Online], Volume 10 Number 3 (30 September 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.3.189-194.1903

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