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, Janet M. S. Skakle, Alan B. Turner, James L. Wardell, Graeme J. R. Watson

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Crystal structures are reported of (E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1Hinden-1-one, 1, (E)-2-(4-dimethylaminobenzylidene)-2,3dihydro-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-(4hydroxy-3,5-dimethylbenzylidene)-2,3-dihydro-1H-indan1-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-dihydro1H-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 sp(3) atom. The molecules exhibit slight deviations from overall planarity as shown by the dihedral angles, > 8.15(6)degrees 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 center dot center dot center dot O1(carbonyl) hydrogen bonds. The carbonyl oxygen atom in compounds 1-4 are involved in non-classical C-H center dot center dot center dot O intermolecular hydrogen bonds. Intermolecular C-H center dot center dot center dot pi interactions are present in 2, 3 and 6, while pi center dot center dot center dot pi are present in 2-4 and 6. As noted in the structure determinations of these compounds, different pi center dot center dot center dot pi 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.

Original languageEnglish
Pages (from-to)317-333
Number of pages17
JournalZeitschrift fur kristallographie-Crystalline materials
Volume232
Issue number4
Early online date7 Mar 2017
DOIs
Publication statusPublished - 1 Apr 2017

Keywords

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

Cite this

Structural studies of (E)-2-(benzylidene)-2,3-dihydro-1H-inden-1-one derivatives : crystal structures and Hirshfeld surface analysis. / Baddeley, Thomas C.; Gomes, Ligia R.; Low, John N.; Skakle, Janet M. S.; Turner, Alan B.; Wardell, James L.; Watson, Graeme J. R.

In: Zeitschrift fur kristallographie-Crystalline materials, Vol. 232, No. 4, 01.04.2017, p. 317-333.

Research output: Contribution to journalArticle

@article{ce5f5fca8cc04f028f41af9006e42f05,
title = "Structural studies of (E)-2-(benzylidene)-2,3-dihydro-1H-inden-1-one derivatives: crystal structures and Hirshfeld surface analysis",
abstract = "Crystal structures are reported of (E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1Hinden-1-one, 1, (E)-2-(4-dimethylaminobenzylidene)-2,3dihydro-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-(4hydroxy-3,5-dimethylbenzylidene)-2,3-dihydro-1H-indan1-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-dihydro1H-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 sp(3) atom. The molecules exhibit slight deviations from overall planarity as shown by the dihedral angles, > 8.15(6)degrees 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 center dot center dot center dot O1(carbonyl) hydrogen bonds. The carbonyl oxygen atom in compounds 1-4 are involved in non-classical C-H center dot center dot center dot O intermolecular hydrogen bonds. Intermolecular C-H center dot center dot center dot pi interactions are present in 2, 3 and 6, while pi center dot center dot center dot pi are present in 2-4 and 6. As noted in the structure determinations of these compounds, different pi center dot center dot center dot pi 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",
author = "Baddeley, {Thomas C.} and Gomes, {Ligia R.} and Low, {John N.} and Skakle, {Janet M. S.} and Turner, {Alan B.} and Wardell, {James L.} and Watson, {Graeme J. R.}",
year = "2017",
month = "4",
day = "1",
doi = "10.1515/zkri-2016-2020",
language = "English",
volume = "232",
pages = "317--333",
journal = "Zeitschrift fur kristallographie-Crystalline materials",
issn = "2194-4946",
publisher = "Walter de Gruyter GmbH",
number = "4",

}

TY - JOUR

T1 - Structural studies of (E)-2-(benzylidene)-2,3-dihydro-1H-inden-1-one derivatives

T2 - crystal structures and Hirshfeld surface analysis

AU - Baddeley, Thomas C.

AU - Gomes, Ligia R.

AU - Low, John N.

AU - Skakle, Janet M. S.

AU - Turner, Alan B.

AU - Wardell, James L.

AU - Watson, Graeme J. R.

PY - 2017/4/1

Y1 - 2017/4/1

N2 - Crystal structures are reported of (E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1Hinden-1-one, 1, (E)-2-(4-dimethylaminobenzylidene)-2,3dihydro-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-(4hydroxy-3,5-dimethylbenzylidene)-2,3-dihydro-1H-indan1-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-dihydro1H-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 sp(3) atom. The molecules exhibit slight deviations from overall planarity as shown by the dihedral angles, > 8.15(6)degrees 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 center dot center dot center dot O1(carbonyl) hydrogen bonds. The carbonyl oxygen atom in compounds 1-4 are involved in non-classical C-H center dot center dot center dot O intermolecular hydrogen bonds. Intermolecular C-H center dot center dot center dot pi interactions are present in 2, 3 and 6, while pi center dot center dot center dot pi are present in 2-4 and 6. As noted in the structure determinations of these compounds, different pi center dot center dot center dot pi 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.

AB - Crystal structures are reported of (E)-2-(4-hydroxybenzylidene)-2,3-dihydro-1Hinden-1-one, 1, (E)-2-(4-dimethylaminobenzylidene)-2,3dihydro-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-(4hydroxy-3,5-dimethylbenzylidene)-2,3-dihydro-1H-indan1-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-dihydro1H-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 sp(3) atom. The molecules exhibit slight deviations from overall planarity as shown by the dihedral angles, > 8.15(6)degrees 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 center dot center dot center dot O1(carbonyl) hydrogen bonds. The carbonyl oxygen atom in compounds 1-4 are involved in non-classical C-H center dot center dot center dot O intermolecular hydrogen bonds. Intermolecular C-H center dot center dot center dot pi interactions are present in 2, 3 and 6, while pi center dot center dot center dot pi are present in 2-4 and 6. As noted in the structure determinations of these compounds, different pi center dot center dot center dot pi 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.

KW - 2-(arylidene)-2,3-dihydro-1H-inden-1-one compounds

KW - Hirshfeld surface calculations

KW - intermolecular interactions

KW - X-ray crystallography

U2 - 10.1515/zkri-2016-2020

DO - 10.1515/zkri-2016-2020

M3 - Article

VL - 232

SP - 317

EP - 333

JO - Zeitschrift fur kristallographie-Crystalline materials

JF - Zeitschrift fur kristallographie-Crystalline materials

SN - 2194-4946

IS - 4

ER -