• Henao, José Antonio
• Toro, Robert A.
• Streek, Jacco Van De

Abstract

<jats:p>The previously unreported crystal structure of (<jats:italic>S</jats:italic>)-Dapoxetine hydrochloride (DAPHCl), the only active pharmaceutical ingredient specially developed for the treatment of premature ejaculation in men, has been determined from laboratory X-ray powder diffraction data with DASH and refined by the Rietveld method with TOPAS-Academic. The structure was evaluated and optimized by dispersion-corrected DFT calculations. This compound crystallizes in an orthorhombic cell, space group <jats:italic>P</jats:italic>2<jats:sub>1</jats:sub>2<jats:sub>1</jats:sub>2<jats:sub>1</jats:sub>, with unit-cell parameters <jats:italic>a</jats:italic>= 6.3208(3) Å, <jats:italic>b</jats:italic> = 10.6681(5) Å, <jats:italic>c</jats:italic> = 28.1754(10) Å, <jats:italic>V</jats:italic> = 1899.89(14) Å<jats:sup>3</jats:sup>, <jats:italic>Z</jats:italic> = 4. The refinement converged to <jats:italic>R</jats:italic><jats:sub>p</jats:sub><jats:italic>=</jats:italic> 0.0442, <jats:italic>R</jats:italic><jats:sub>wp</jats:sub><jats:italic>=</jats:italic> 0.0577, and GoF <jats:italic>=</jats:italic> 2.440. The crystal structure is a complex 3D arrangement of DAPHCl moieties held together by hydrogen bonds, π⋯π, and C–H⋯π interactions. The chloride ions form layers parallel to the <jats:italic>ab</jats:italic> plane and are connected by dapoxetinium moieties through N–H⋯Cl and C–H⋯Cl hydrogen bonds. These layers stack along the <jats:italic>c</jats:italic>-axis, which are connected by C–H⋯π interactions. Hirshfeld surface analysis and fingerprint plot calculations have been performed.</jats:p>

Topics

• impedance spectroscopy
• dispersion
• surface
• compound
• Hydrogen
• density functional theory
• space group