Journal of Chemical Crystallography

, Volume 43, Issue 3, pp 144–150 | Cite as

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
Original Paper

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 I41/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 R22(10) for I and III, and an inversion dimer of graph-set motif R22(14) for II. In addition, some short contacts of C···C, C···O and Cl···Cl are observed for I, II and III, respectively.

Graphical Abstract

This paper presents the synthesis, characterization and structural studies of three derivatives of Phthalimides which are well known cytotoxic DNA intercalating agents and potential anti-cancer agents, inhibit the acute inflammatory response and HIV-1 reverse transcriptases and found usefulness in OLEDs. Compounds I and II crystallize in a monoclinic crystal system (space group P21/c) while compound III crystallizes in a tetragonal crystal system (space group I41/a). 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. A few weak C–H···O interactions form double-tape structures for I and III, and a dimer for II.

Keywords

N-Phenylphthalimide Crystal structure Intermolecular contact Graph-set 

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Muhammad Khawar Rauf
    • 1
  • Rabia Mushtaq
    • 1
  • Amin Badshah
    • 1
  • Robert Kingsford-Adaboh
    • 2
  • Jerry Joe Ebow Kingsley Harrison
    • 2
  • Hiroyuki Ishida
    • 3
  1. 1.Department of ChemistryQuaid-i-Azam UniversityIslamabadPakistan
  2. 2.Department of Chemistry, Faculty of ScienceUniversity of GhanaLegon, AccraGhana
  3. 3.Department of Chemistry, Faculty of ScienceOkayama UniversityOkayamaJapan

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