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Crystal structure from laboratory X-ray powder diffraction data, DFT-D calculations, Hirshfeld surface analysis, and energy frameworks of a new polymorph of 1-benzothiophene-2-carboxylic acid

Published online by Cambridge University Press:  14 January 2021

Analio J. Dugarte-Dugarte Open the ORCID record for Analio J. Dugarte-Dugarte [Opens in a new window] ,
Jacco van de Streek ,
Graciela Díaz de Delgado Open the ORCID record for Graciela Díaz de Delgado [Opens in a new window] ,
Alicja Rafalska-Lasocha Open the ORCID record for Alicja Rafalska-Lasocha [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, Mérida5101, Venezuela
Jacco van de Streek
Affiliation:
Avant-garde Materials Simulation, Alte Str. 2, MerzhausenD-79249, Germany
Graciela Díaz de Delgado
Affiliation:
Laboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida5101, Venezuela
Alicja Rafalska-Lasocha
Affiliation:
Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, Krakow30-387, Poland
José Miguel Delgado*
Affiliation:
Laboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida5101, Venezuela
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

Several benzothiophene-based compounds, including 1-benzothiophene-2-carboxylic acid, exhibit a wide variety of pharmacological activities. They have been extensively used to treat various types of diseases with high therapeutic effectiveness. In this contribution, the crystal structure of a new polymorph of 1-benzothiophene-2-carboxylic acid (BTCA) was determined from laboratory X-ray powder diffraction data with DASH, refined by the Rietveld method with TOPAS-Academic, and optimized using DFT-D calculations. The new form of 1-benzothiophene-2-carboxylic acid crystallizes in space group C2/c (No. 15) with a = 14.635(4), b = 5.8543(9), c = 19.347(3) Å, β = 103.95(1)°, V = 1608.8(6) Å3, and Z = 8. The structure is a complex 3D arrangement which can be described in terms of hydrogen-bonded dimers of BTCA molecules, joined by the acid–acid homosynthon, which interact through C–H⋯O hydrogen bonds to produce tapes further connected through head-to-tail π⋯π and edge-to-face C–H⋯π interactions. A comparison with a previously reported triclinic polymorph and with the related 1-benzofuran-2-carboxylic acid (BFCA) is also presented.

Keywords

1-benzothiophene-2-carboxylic acidthionaphthene-2-carboxylic acidstructure determinationDFT-D calculationsHirshfeld surface analysis
Type
Technical Article
Information
Powder Diffraction , Volume 36 , Issue 1 , March 2021 , pp. 2 - 13
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Copyright
Copyright © The Author(s), 2021. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

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