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Crystal structure from laboratory X-ray powder diffraction data, DFT-D calculations, and Hirshfeld surface analysis of (S)-dapoxetine hydrochloride

Published online by Cambridge University Press:  13 September 2022

Analio J. Dugarte-Dugarte Open the ORCID record for Analio J. Dugarte-Dugarte [Opens in a new window] ,
Robert A. Toro ,
Jacco van de Streek ,
José Antonio Henao ,
Graciela Díaz de Delgado Open the ORCID record for Graciela Díaz de Delgado [Opens in a new window]  and
José Miguel Delgado Open the ORCID record for José Miguel Delgado [Opens in a new window]
Analio J. Dugarte-Dugarte
Affiliation:
Laboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida 5101, Venezuela
Robert A. Toro
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, Bucaramanga, Colombia
Jacco van de Streek
Affiliation:
Avant-garde Materials Simulation, Alte Str. 2, D-79249 Merzhausen, Germany
José Antonio Henao
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, Bucaramanga, Colombia
Graciela Díaz de Delgado
Affiliation:
Laboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida 5101, Venezuela
José Miguel Delgado*
Affiliation:
Laboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida 5101, Venezuela
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The previously unreported crystal structure of (S)-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 P212121, with unit-cell parameters a= 6.3208(3) Å, b = 10.6681(5) Å, c = 28.1754(10) Å, V = 1899.89(14) Å3, Z = 4. The refinement converged to Rp = 0.0442, Rwp = 0.0577, and GoF = 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 ab plane and are connected by dapoxetinium moieties through N–H⋯Cl and C–H⋯Cl hydrogen bonds. These layers stack along the c-axis, which are connected by C–H⋯π interactions. Hirshfeld surface analysis and fingerprint plot calculations have been performed.

Keywords

dapoxetine hydrochloridepowder diffractionstructure determinationDFT-D calculationsHirshfeld surface analysis
Type
New Diffraction Data
Information
Powder Diffraction , Volume 37 , Issue 4 , December 2022 , pp. 216 - 224
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Copyright
Copyright © The Author(s), 2022. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

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