N-(X-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (with X = 2 and 4).
The structures of N-(2-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide and N-(4-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, both C16H13ClN2O4S, are stabilized by extensive intramolecular hydrogen bonds. The 4-chloro derivative forms dimeric pairs of molecules lying about inversion centres as a result of intermolecular N-H...O hydrogen bonds, forming 14-membered rings representing an R2(2)(14) motif; the 2-chloro derivative is devoid of any such intermolecular hydrogen bonds. The heterocyclic thiazine rings in both structures adopt half-chair conformations.
Siddiqui
Waseeq Ahmad
WA
Department of Chemistry, University of Sargodha, Sargodha, Pakistan.
Ahmad
Saeed
S
Tariq
Muhammad Ilyas
MI
Siddiqui
Hamid Latif
HL
Parvez
Masood
M
D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013843:Thiazines / Q000737:chemistry*
D006575:Heterocyclic Compounds, 3-Ring; D006843:Hydrocarbons, Chlorinated; C527970:N-(2-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide; C527971:N-(4-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide; D013843:Thiazines