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

5 Citations (Scopus)

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 1 2013

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

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