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Molecular conformation of the racemic indan derivative (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxamide

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Abstract

This paper presents the structural characterization of the indan derivative (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxamide, which was unambiguously determined by X-ray diffraction (XRD) to be a racemate (R/S: 50/50) crystallizing in an achiral crystal structure (P21/c, a = 9.3180(1) Å, b = 7.9070(2) Å, c = 19.7550(4) Å, β = 103.250(1)°, V = 1416.75(5) Å3 and Z = 4). The diastereomers are related by the inversion symmetry and linked by H bond forming a dimer. The crystal packing is stabilized by hydrogen bonds, including the classical one responsible for the formation of centrosymmetric dimers, and non-classical ones involving C–H···O and C–H···π-aryl interactions. The intra and intermolecular geometry of the title compound is compared to the (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxylic acid one, which also present an achiral crystal structure from racemates (R/S: 50/50). The two indan derivatives crystallize in a very similar unit cell.

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Acknowledgements

The authors wish to thank the financial support by Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG—EDT-3310/06, APQ-2011-5.02/07, APQ-6010-5.02/07), TWAS, CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES). RSC and ACD thank CNPq for a fellowship.

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Authors and Affiliations

  1. Departamento de Ciências Exatas – Laboratório de Cristalografia, Universidade Federal de Alfenas – UNIFAL-MG, Rua Gabriel Monteiro da Silva, 714, CEP 37130-000, Alfenas, MG, Brazil

    Antônio C. Doriguetto & Rodrigo S. Corrêa

  2. Instituto de Química, Universidade de São Paulo (IQ-USP), São Paulo, SP, Brazil

    Fernanda A. Siqueira & Luiz F. Silva Jr.

  3. Instituto de Física de São Carlos, Universidade de São Paulo (IFSC-USP), São Carlos, SP, Brazil

    Rodrigo S. Corrêa & Javier Ellena

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  1. Antônio C. Doriguetto
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  2. Rodrigo S. Corrêa
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  3. Fernanda A. Siqueira
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  4. Luiz F. Silva Jr.
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  5. Javier Ellena
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Correspondence to Antônio C. Doriguetto.

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Doriguetto, A.C., Corrêa, R.S., Siqueira, F.A. et al. Molecular conformation of the racemic indan derivative (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxamide. Struct Chem 20, 795–800 (2009). https://doi.org/10.1007/s11224-009-9469-1

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