Synthesis and Crystal Structure Studies of Three N-Phenylphthalimide Derivatives
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- Rauf, M.K., Mushtaq, R., Badshah, A. et al. J Chem Crystallogr (2013) 43: 144. doi:10.1007/s10870-013-0399-9
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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.