Crystal and Vibrational Analysis of a Novel Alcohol Derivate from Chlorthalidone: Ethyl-Chlorthalidone

Abstract

The crystal structure of the novel alcohol derivate from chlorthalidone, ethyl-chlorthalidone [2-chloro-5-(1-ethyl-3-oxo-1-isoindolinyl)benzenesulfonamide hydrated], C₁₆H₁₅ClN₂O₄S.H₂O, was determined by X-ray diffraction at 295 K. This molecule crystallized in an orthorhombic space group Pca2₁ with a = 7.928(2) Å, b = 10.920(2) Å, c = 19.459(4) Å, α = β = γ = 90°. This compound is stabilized by intra and intermolecular NHO and OHO hydrogen bonds. These interactions which involve water molecules of the network give rise to a two-dimensional (2-D) array parallel to the (110) direction. The three-dimensional design of the compound is observed through weak NH···O hydrogen bonds (N2–H2A···O4). The NMR study was a complementary tool for crystal characterization. The spectra analysis clearly shows that signs of ethyl group atoms appear in strong field whereas the others atoms were identified in weak magnetic field (above of 140 ppm). The vibrational spectra present bands in the region of 2890–2940 cm⁻¹ which can be assigned as symmetric and asymmetric modes of CH₂ and CH₃ groups. These results are in agreement with the crystal data which indicate the presence of ethyl group in this molecule.

Graphical Abstract

The crystal structure of the novel alcohol derivate from chlorthalidone (ethyl-chlorthalidone) is stabilized by intra and intermolecular NHO and OHO hydrogen bonds, that give rise to a two-dimensional (2-D) array parallel to the (110) direction.