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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 , John N. Low EMAIL logo , Janet M.S. Skakle , Alan B. Turner , James L. Wardell EMAIL logo and Graeme J.R. Watson
Published/Copyright: March 7, 2017
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 232 Issue 4

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.

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

Acknowledgments

The authors thank the NCS crystallographic service at Southampton and the valuable assistance of the staff for the data collection for compounds 1–4. JLW thanks FAPERJ and CNPq, Brazil for support.

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2016-2020) offers supplementary material, available to authorized users.

Received: 2016-11-2
Accepted: 2016-12-21
Published Online: 2017-3-7
Published in Print: 2017-4-1

©2017 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. On the autocorrelation method of external parameter depending data-sets
  5. Comparison of experimental and theoretical results for the structure and elastic properties of moganite
  6. Organic and Metalorganic Crystal Structures
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  9. Competition between intermolecular hydrogen bonding and stacking in the crystals of 4-Hydroxy-N-(pyridin-2-yl)-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides
  10. Structural studies of (E)-2-(benzylidene)- 2,3-dihydro-1H-inden-1-one derivatives: crystal structures and Hirshfeld surface analysis
  11. Corrigendum
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https://doi.org/10.1515/zkri-2016-2020
Keywords for this article
2-(arylidene)-2,3-dihydro-1H-inden-1-one compounds; Hirshfeld surface calculations; intermolecular interactions; X-ray crystallography

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. On the autocorrelation method of external parameter depending data-sets
  5. Comparison of experimental and theoretical results for the structure and elastic properties of moganite
  6. Organic and Metalorganic Crystal Structures
  7. Supramolecular association in (μ2-pyrazine)-tetrakis(N,N-bis(2-hydroxyethyl)dithiocarbamato)dizinc(II) and its di-dioxane solvate
  8. Intermolecular hydrogen bonding H···Cl− in the solid palladium(II)-diaminocarbene complexes
  9. Competition between intermolecular hydrogen bonding and stacking in the crystals of 4-Hydroxy-N-(pyridin-2-yl)-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides
  10. Structural studies of (E)-2-(benzylidene)- 2,3-dihydro-1H-inden-1-one derivatives: crystal structures and Hirshfeld surface analysis
  11. Corrigendum
  12. Corrigendum to: On the unit cell volume expansion in homogeneous series of isotypic structures of “ionic” inorganic compounds
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