Crystal and molecular structure of N-phenyl substituted 1,2-, 2,3- and 1,8-naphthalimides

Y. Dromzée, J. Kossanyi, V. Wintgens, P. Valat, L. Biczók, A. Demeter, T. Bérces

Research output: Contribution to journalArticle

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Abstract

The three structures were solved by direct methods and refined by full-matrix least-squares procedure. 2-phenyl-1 H-benz[f]isoindole-l,3(2 H)-dione, (compound 1): orthorhombic, space group Pcab, a = 7.618(1) Å, b = 11.717(2) Å, c = 28.540(4) Å, V = 2547.4(7) Å3, Z = 8 and d = 1.425 Mg m-3, R = 0.038 (Rw = 0.038) for 190 parameters and 820 observations with I > 2.5σ(I). 2-phenyl-1 H-benz[e]isoindole-1,3 (2 H)-dione (compound 2): orthorhombic, space group Pc21b, a = 6.7042(9) Å, b = 7.4589(9) Å, c = 26.441(7) Å, V = 1322.4(4) Å3, Z = 4 and d = 1.373 Mg m-3, R = 0.037 (Rw = 0.032) for 190 parameters and 1186 observations with I > 3σ(I). 2-phenyl-1 H-benz[de]isoquinoline-1,3 (2 H)-dione (compound 3): monoclinic, space group C2/c, a = 13.501(3) Å, b = 13.212(4) Å, c = 8.305(2) Å, β = 116.24(2)°, V = 1329(9) Å3, Z = 4, and d = 1.366 Mg m-3= 0.038 (Rw = 0.033) for 71 parameters and 754 observations with I > 3σ(I). The plane of the N-phenyl substituent has an axis which lies in the plane of the naphthalimide part and passes by the carbon atom bound to the nitrogen atom and by the carbon in para position. It makes a dihedral angle with the plane of the naphthalimide moiety of 59.2°, 46.5° and 69.4° for the compounds 1,2 and 3 respectively. This difference in geometry between the three molecules brings new insights into their spectroscopic properties.

Original languageEnglish
Pages (from-to)760-765
Number of pages6
JournalZeitschrift fur Kristallographie - New Crystal Structures
Volume210
Issue number10
DOIs
Publication statusPublished - 1995

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Naphthalimides
Isoindoles
Dione
Molecular structure
molecular structure
Carbon
Crystal structure
Atoms
crystal structure
Dihedral angle
Nitrogen
carbon
nitrogen atoms
Molecules
Geometry
dihedral angle
matrices
geometry
atoms
molecules

Keywords

  • Conformation
  • Crystal structure
  • N-phenyl naphthalimides
  • Spectroscopic properties in the solid state

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Crystal and molecular structure of N-phenyl substituted 1,2-, 2,3- and 1,8-naphthalimides. / Dromzée, Y.; Kossanyi, J.; Wintgens, V.; Valat, P.; Biczók, L.; Demeter, A.; Bérces, T.

In: Zeitschrift fur Kristallographie - New Crystal Structures, Vol. 210, No. 10, 1995, p. 760-765.

Research output: Contribution to journalArticle

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abstract = "The three structures were solved by direct methods and refined by full-matrix least-squares procedure. 2-phenyl-1 H-benz[f]isoindole-l,3(2 H)-dione, (compound 1): orthorhombic, space group Pcab, a = 7.618(1) {\AA}, b = 11.717(2) {\AA}, c = 28.540(4) {\AA}, V = 2547.4(7) {\AA}3, Z = 8 and d = 1.425 Mg m-3, R = 0.038 (Rw = 0.038) for 190 parameters and 820 observations with I > 2.5σ(I). 2-phenyl-1 H-benz[e]isoindole-1,3 (2 H)-dione (compound 2): orthorhombic, space group Pc21b, a = 6.7042(9) {\AA}, b = 7.4589(9) {\AA}, c = 26.441(7) {\AA}, V = 1322.4(4) {\AA}3, Z = 4 and d = 1.373 Mg m-3, R = 0.037 (Rw = 0.032) for 190 parameters and 1186 observations with I > 3σ(I). 2-phenyl-1 H-benz[de]isoquinoline-1,3 (2 H)-dione (compound 3): monoclinic, space group C2/c, a = 13.501(3) {\AA}, b = 13.212(4) {\AA}, c = 8.305(2) {\AA}, β = 116.24(2)°, V = 1329(9) {\AA}3, Z = 4, and d = 1.366 Mg m-3= 0.038 (Rw = 0.033) for 71 parameters and 754 observations with I > 3σ(I). The plane of the N-phenyl substituent has an axis which lies in the plane of the naphthalimide part and passes by the carbon atom bound to the nitrogen atom and by the carbon in para position. It makes a dihedral angle with the plane of the naphthalimide moiety of 59.2°, 46.5° and 69.4° for the compounds 1,2 and 3 respectively. This difference in geometry between the three molecules brings new insights into their spectroscopic properties.",
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author = "Y. Dromz{\'e}e and J. Kossanyi and V. Wintgens and P. Valat and L. Bicz{\'o}k and A. Demeter and T. B{\'e}rces",
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T1 - Crystal and molecular structure of N-phenyl substituted 1,2-, 2,3- and 1,8-naphthalimides

AU - Dromzée, Y.

AU - Kossanyi, J.

AU - Wintgens, V.

AU - Valat, P.

AU - Biczók, L.

AU - Demeter, A.

AU - Bérces, T.

PY - 1995

Y1 - 1995

N2 - The three structures were solved by direct methods and refined by full-matrix least-squares procedure. 2-phenyl-1 H-benz[f]isoindole-l,3(2 H)-dione, (compound 1): orthorhombic, space group Pcab, a = 7.618(1) Å, b = 11.717(2) Å, c = 28.540(4) Å, V = 2547.4(7) Å3, Z = 8 and d = 1.425 Mg m-3, R = 0.038 (Rw = 0.038) for 190 parameters and 820 observations with I > 2.5σ(I). 2-phenyl-1 H-benz[e]isoindole-1,3 (2 H)-dione (compound 2): orthorhombic, space group Pc21b, a = 6.7042(9) Å, b = 7.4589(9) Å, c = 26.441(7) Å, V = 1322.4(4) Å3, Z = 4 and d = 1.373 Mg m-3, R = 0.037 (Rw = 0.032) for 190 parameters and 1186 observations with I > 3σ(I). 2-phenyl-1 H-benz[de]isoquinoline-1,3 (2 H)-dione (compound 3): monoclinic, space group C2/c, a = 13.501(3) Å, b = 13.212(4) Å, c = 8.305(2) Å, β = 116.24(2)°, V = 1329(9) Å3, Z = 4, and d = 1.366 Mg m-3= 0.038 (Rw = 0.033) for 71 parameters and 754 observations with I > 3σ(I). The plane of the N-phenyl substituent has an axis which lies in the plane of the naphthalimide part and passes by the carbon atom bound to the nitrogen atom and by the carbon in para position. It makes a dihedral angle with the plane of the naphthalimide moiety of 59.2°, 46.5° and 69.4° for the compounds 1,2 and 3 respectively. This difference in geometry between the three molecules brings new insights into their spectroscopic properties.

AB - The three structures were solved by direct methods and refined by full-matrix least-squares procedure. 2-phenyl-1 H-benz[f]isoindole-l,3(2 H)-dione, (compound 1): orthorhombic, space group Pcab, a = 7.618(1) Å, b = 11.717(2) Å, c = 28.540(4) Å, V = 2547.4(7) Å3, Z = 8 and d = 1.425 Mg m-3, R = 0.038 (Rw = 0.038) for 190 parameters and 820 observations with I > 2.5σ(I). 2-phenyl-1 H-benz[e]isoindole-1,3 (2 H)-dione (compound 2): orthorhombic, space group Pc21b, a = 6.7042(9) Å, b = 7.4589(9) Å, c = 26.441(7) Å, V = 1322.4(4) Å3, Z = 4 and d = 1.373 Mg m-3, R = 0.037 (Rw = 0.032) for 190 parameters and 1186 observations with I > 3σ(I). 2-phenyl-1 H-benz[de]isoquinoline-1,3 (2 H)-dione (compound 3): monoclinic, space group C2/c, a = 13.501(3) Å, b = 13.212(4) Å, c = 8.305(2) Å, β = 116.24(2)°, V = 1329(9) Å3, Z = 4, and d = 1.366 Mg m-3= 0.038 (Rw = 0.033) for 71 parameters and 754 observations with I > 3σ(I). The plane of the N-phenyl substituent has an axis which lies in the plane of the naphthalimide part and passes by the carbon atom bound to the nitrogen atom and by the carbon in para position. It makes a dihedral angle with the plane of the naphthalimide moiety of 59.2°, 46.5° and 69.4° for the compounds 1,2 and 3 respectively. This difference in geometry between the three molecules brings new insights into their spectroscopic properties.

KW - Conformation

KW - Crystal structure

KW - N-phenyl naphthalimides

KW - Spectroscopic properties in the solid state

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