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Zeitschrift für Kristallographie - Crystalline Materials

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Volume 232, Issue 4 (Apr 2017)

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Structural studies of (E)-2-(benzylidene)- 2,3-dihydro-1H-inden-1-one derivatives: crystal structures and Hirshfeld surface analysis

Thomas C. Baddeley / Ligia R. Gomes
  • FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal
  • REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007, Porto, Portugal
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ John N. Low / Janet M.S. Skakle / Alan B. Turner / James L. Wardell
  • Corresponding author
  • Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, UK
  • Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, Brazil
  • Email
  • Other articles by this author:
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/ Graeme J.R. Watson
Published Online: 2017-03-07 | DOI: https://doi.org/10.1515/zkri-2016-2020

Abstract

Crystal structures are reported of (E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1H-inden-1-one, 1, (E)-2-(4-dimethylaminobenzylidene)-2,3- dihydro-1H-inden-1-one, 2, (E)-2-(4-cyanobenzylidene)-2,3-dihydro-1H-inden-1-one, 3, and monoclinic-(E)- 2-(3-nitrobenzylidene)-2,3-dihydro-1H-inden-1-one, monoclinic-4, all from data collected at 100 K and (E)-2-(4-hydroxy-3,5-dimethylbenzylidene)-2,3-dihydro-1H-indan-1-one, 6, from data collected at 299 K. An earlier triclinic form of 4 has been reported. Also reported herein are the Hirshfeld suface calculations for these five compounds, as well as that of 2-(4-methoxybenzylidene)-2,3-dihydro-1H-inden-1-one, 5,whose crystal structure has been previously reported. The three rings in each of the compounds, 1–4 and 6, are essentially planar, including the five-membered ring containing a formally hydridized sp3 atom. The molecules exhibit slight deviations from overall planarity as shown by the dihedral angles, >8.15(6)° between the 2,3-dihydro-1H-inden-1-one fragments and the phenyl fragments. The main intermolecular interactions in compounds 1 and are classical O–H···O1(carbonyl) hydrogen bonds. The carbonyl oxygen atom in compounds 1–4 are involved in non-classical C–H···O intermolecular hydrogen bonds. Intermolecular C–H---π interactions are present in 2, 3 and 6, while π···π are present in 2–4 and 6. As noted in the structure determinations of these compounds, different π···π motifs are possible. The Hirshfeld surface calculations, while generally concurring with the intermolecular interactions indicated by PLATON analyses, also reveal significant interactions, which fall below the PLATON radar.

This article offers supplementary material which is provided at the end of the article.

Keywords: 2-(arylidene)-2,3-dihydro-1H-inden-1-one compounds; Hirshfeld surface calculations; intermolecular interactions; X-ray crystallography

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About the article

aDied: 16th February 2014.

bCurrent address: Banff Academy, Bellevue Road, Banff, Aberdeenshire, AB45 1BY, UK.


Received: 2016-11-02

Accepted: 2016-12-21

Published Online: 2017-03-07

Published in Print: 2017-04-01


Citation Information: Zeitschrift für Kristallographie - Crystalline Materials, ISSN (Online) 2196-7105, ISSN (Print) 2194-4946, DOI: https://doi.org/10.1515/zkri-2016-2020.

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