TY - JOUR
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
Y1 - 2013/3
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.
KW - Crystal structure
KW - Graph-set
KW - Intermolecular contact
KW - N-Phenylphthalimide
UR - http://www.scopus.com/inward/record.url?scp=84876414231&partnerID=8YFLogxK
U2 - 10.1007/s10870-013-0399-9
DO - 10.1007/s10870-013-0399-9
M3 - Article
AN - SCOPUS:84876414231
SN - 1074-1542
VL - 43
SP - 144
EP - 150
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
IS - 3
ER -