

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,*)



(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 | Revised: 04 Jul 2019 | Accepted: 05 Jul 2019 | Published: 30 Sep 2019 | Issue Date: September 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 P͞1 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.
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DOI: 10.5155/eurjchem.10.3.189-194.1903
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University of Liège, Liège, Belgium
Citations
[1]. Koffi Sénam Etsè, Guillermo Zaragoza, Kodjo Djidjolé Etsè
Easy preparation of novel 3,3-dimethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide: Molecular structure, Hirshfeld surface, NCI analyses and molecular docking on AMPA receptors
Journal of Molecular Structure 1238, 130435, 2021
DOI: 10.1016/j.molstruc.2021.130435

[2]. Koffi Sénam Etsè, Guillermo Zaragoza, Albert Demonceau
Novel trans iodo(2-(N-alkylsulfamoyl)phenyl)bis(-triphenylphosphine palladium) complexes: Synthesis, mass spectrometry, X-ray structural description, steric map, near infrared analyses and catalytic activities evaluation
Polyhedron 224, 116013, 2022
DOI: 10.1016/j.poly.2022.116013

[3]. Koffi Sénam Etsè, Guillermo Zaragoza, Frédéric Boschini, Abdelfattah Mahmoud
New N-methylimidazolium hexachloroantimonate: Synthesis, crystal structure, Hirshfeld surface and catalytic activity of in cyclopropanation of stryrene
Inorganic Chemistry Communications 122, 108291, 2020
DOI: 10.1016/j.inoche.2020.108291

[4]. Koffi Senam Etse, Laura Comeron Lamela, Guillermo Zaragoza, Bernard Pirotte
Synthesis, crystal structure, Hirshfeld surface and interaction energies analysis of 5-methyl-1,3-bis(3-nitrobenzyl)pyrimidine-2,4(1H,3H)-dione
European Journal of Chemistry 11(2), 91, 2020
DOI: 10.5155/eurjchem.11.2.91-99.1973

[5]. Koffi Sénam Etsè, Kodjo Djidjolé Etsè, Pauline Nyssen, Ange Mouithys-Mickalad
Assessment of anti-inflammatory-like, antioxidant activities and molecular docking of three alkynyl-substituted 3-ylidene-dihydrobenzo[d]isothiazole 1,1-dioxide derivatives
Chemico-Biological Interactions 344, 109513, 2021
DOI: 10.1016/j.cbi.2021.109513

[6]. Koffi Sénam Etsè, Albert Demonceau, Guillermo Zaragoza, Didier Serteyn, Ange Mouithys-Mickalad
Design, synthesis and biochemical evaluation of novel 2-amino-3-(7-methoxybenzo[d][1,3]dioxol-5-yl)propanoic acid using Horseradish peroxidase (HRP) activity, cellular ROS inhibition and molecular docking study
Journal of Molecular Structure 1250, 131668, 2022
DOI: 10.1016/j.molstruc.2021.131668

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