Synthesis and crystal structure studies of three n-phenylphthalimide derivatives

Muhammad Khawar Rauf, Rabia Mushtaq, Amin Badshah, Robert Kingsford-Adaboh, Jerry Joe Ebow Kingsley Harrison, Hiroyuki Ishida

Research output: Contribution to journalArticle

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Abstract

The three N-phenylphthalimide derivatives, 2-(3,4-dichlorophenyl) isoindoline-1,3-dione (I), 2-(2,4-dichlorophenyl)isoindoline-1,3-dione (II) and 2-(2,4,5-trichlorophenyl)isoindoline-1,3-dione (III), were synthesized by the condensation of equimolar amounts of phthalic anhydride and 3,4-dichloroaniline, 2,4-dichloroaniline, 2,4,5-trichloroaniline, respectively, under acetic acid reflux and their structures determined by a combination of elemental analysis, FT-IR, 1H & 13C-NMR spectroscopy and single crystal X-ray diffraction studies. Compounds I and II crystallize in a monoclinic crystal system (space group P21/c) with cell parameters of a = 5.7414(2), b = 8.0917(6), c = 26.077(1) Å and β = 99.4709(12) o for compound I, and a = 12.7133(9), b = 13.4328(9), c = 7.2603(5) Å and β = 93.210 (2)o for compound II. On the other hand, compound III crystallizes in a tetragonal crystal system (space group I4 1/a) with a = 13.4607(9) and c = 30.100(2) Å. The phthalimide moieties of these compounds are essentially planar, while the chloro-substituted phenyl ring of each compound shows consistent twist from the phthalimide plane with dihedral angles of 61.02(3), 69.09(3) and 85.78(5)o, respectively, for I, II and III. In the crystal structures of these compounds, a few weak C-H···O interactions form double-tape structures of centrosymmetric dimers of graph-set notation R 2 2 (10) for I and III, and an inversion dimer of graph-set motif R 2 2 (14) for II. In addition, some short contacts of C···C, C···O and Cl·· ·Cl are observed for I, II and III, respectively.

Original languageEnglish
Pages (from-to)144-150
Number of pages7
JournalJournal of Chemical Crystallography
Volume43
Issue number3
DOIs
Publication statusPublished - Mar 2013

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Dione
Dimers
phthalimides
Crystal structure
Derivatives
Crystals
crystal structure
Dihedral angle
Carbon Monoxide
synthesis
dimers
Acetic Acid
Tapes
Nuclear magnetic resonance spectroscopy
crystals
Condensation
Single crystals
anhydrides
acetic acid
X ray diffraction

Keywords

  • Crystal structure
  • Graph-set
  • Intermolecular contact
  • N-Phenylphthalimide

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

Cite this

Synthesis and crystal structure studies of three n-phenylphthalimide derivatives. / Rauf, Muhammad Khawar; Mushtaq, Rabia; Badshah, Amin; Kingsford-Adaboh, Robert; Harrison, Jerry Joe Ebow Kingsley; Ishida, Hiroyuki.

In: Journal of Chemical Crystallography, Vol. 43, No. 3, 03.2013, p. 144-150.

Research output: Contribution to journalArticle

Rauf, Muhammad Khawar ; Mushtaq, Rabia ; Badshah, Amin ; Kingsford-Adaboh, Robert ; Harrison, Jerry Joe Ebow Kingsley ; Ishida, Hiroyuki. / Synthesis and crystal structure studies of three n-phenylphthalimide derivatives. In: Journal of Chemical Crystallography. 2013 ; Vol. 43, No. 3. pp. 144-150.
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abstract = "The three N-phenylphthalimide derivatives, 2-(3,4-dichlorophenyl) isoindoline-1,3-dione (I), 2-(2,4-dichlorophenyl)isoindoline-1,3-dione (II) and 2-(2,4,5-trichlorophenyl)isoindoline-1,3-dione (III), were synthesized by the condensation of equimolar amounts of phthalic anhydride and 3,4-dichloroaniline, 2,4-dichloroaniline, 2,4,5-trichloroaniline, respectively, under acetic acid reflux and their structures determined by a combination of elemental analysis, FT-IR, 1H & 13C-NMR spectroscopy and single crystal X-ray diffraction studies. Compounds I and II crystallize in a monoclinic crystal system (space group P21/c) with cell parameters of a = 5.7414(2), b = 8.0917(6), c = 26.077(1) {\AA} and β = 99.4709(12) o for compound I, and a = 12.7133(9), b = 13.4328(9), c = 7.2603(5) {\AA} and β = 93.210 (2)o for compound II. On the other hand, compound III crystallizes in a tetragonal crystal system (space group I4 1/a) with a = 13.4607(9) and c = 30.100(2) {\AA}. The phthalimide moieties of these compounds are essentially planar, while the chloro-substituted phenyl ring of each compound shows consistent twist from the phthalimide plane with dihedral angles of 61.02(3), 69.09(3) and 85.78(5)o, respectively, for I, II and III. In the crystal structures of these compounds, a few weak C-H···O interactions form double-tape structures of centrosymmetric dimers of graph-set notation R 2 2 (10) for I and III, and an inversion dimer of graph-set motif R 2 2 (14) for II. In addition, some short contacts of C···C, C···O and Cl·· ·Cl are observed for I, II and III, respectively.",
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T1 - Synthesis and crystal structure studies of three n-phenylphthalimide derivatives

AU - Rauf, Muhammad Khawar

AU - Mushtaq, Rabia

AU - Badshah, Amin

AU - Kingsford-Adaboh, Robert

AU - Harrison, Jerry Joe Ebow Kingsley

AU - Ishida, Hiroyuki

PY - 2013/3

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N2 - The three N-phenylphthalimide derivatives, 2-(3,4-dichlorophenyl) isoindoline-1,3-dione (I), 2-(2,4-dichlorophenyl)isoindoline-1,3-dione (II) and 2-(2,4,5-trichlorophenyl)isoindoline-1,3-dione (III), were synthesized by the condensation of equimolar amounts of phthalic anhydride and 3,4-dichloroaniline, 2,4-dichloroaniline, 2,4,5-trichloroaniline, respectively, under acetic acid reflux and their structures determined by a combination of elemental analysis, FT-IR, 1H & 13C-NMR spectroscopy and single crystal X-ray diffraction studies. Compounds I and II crystallize in a monoclinic crystal system (space group P21/c) with cell parameters of a = 5.7414(2), b = 8.0917(6), c = 26.077(1) Å and β = 99.4709(12) o for compound I, and a = 12.7133(9), b = 13.4328(9), c = 7.2603(5) Å and β = 93.210 (2)o for compound II. On the other hand, compound III crystallizes in a tetragonal crystal system (space group I4 1/a) with a = 13.4607(9) and c = 30.100(2) Å. The phthalimide moieties of these compounds are essentially planar, while the chloro-substituted phenyl ring of each compound shows consistent twist from the phthalimide plane with dihedral angles of 61.02(3), 69.09(3) and 85.78(5)o, respectively, for I, II and III. In the crystal structures of these compounds, a few weak C-H···O interactions form double-tape structures of centrosymmetric dimers of graph-set notation R 2 2 (10) for I and III, and an inversion dimer of graph-set motif R 2 2 (14) for II. In addition, some short contacts of C···C, C···O and Cl·· ·Cl are observed for I, II and III, respectively.

AB - The three N-phenylphthalimide derivatives, 2-(3,4-dichlorophenyl) isoindoline-1,3-dione (I), 2-(2,4-dichlorophenyl)isoindoline-1,3-dione (II) and 2-(2,4,5-trichlorophenyl)isoindoline-1,3-dione (III), were synthesized by the condensation of equimolar amounts of phthalic anhydride and 3,4-dichloroaniline, 2,4-dichloroaniline, 2,4,5-trichloroaniline, respectively, under acetic acid reflux and their structures determined by a combination of elemental analysis, FT-IR, 1H & 13C-NMR spectroscopy and single crystal X-ray diffraction studies. Compounds I and II crystallize in a monoclinic crystal system (space group P21/c) with cell parameters of a = 5.7414(2), b = 8.0917(6), c = 26.077(1) Å and β = 99.4709(12) o for compound I, and a = 12.7133(9), b = 13.4328(9), c = 7.2603(5) Å and β = 93.210 (2)o for compound II. On the other hand, compound III crystallizes in a tetragonal crystal system (space group I4 1/a) with a = 13.4607(9) and c = 30.100(2) Å. The phthalimide moieties of these compounds are essentially planar, while the chloro-substituted phenyl ring of each compound shows consistent twist from the phthalimide plane with dihedral angles of 61.02(3), 69.09(3) and 85.78(5)o, respectively, for I, II and III. In the crystal structures of these compounds, a few weak C-H···O interactions form double-tape structures of centrosymmetric dimers of graph-set notation R 2 2 (10) for I and III, and an inversion dimer of graph-set motif R 2 2 (14) for II. In addition, some short contacts of C···C, C···O and Cl·· ·Cl are observed for I, II and III, respectively.

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