Acta Crystallographica Section B

Volume 65, Part 1 (February 2009)


research papers



Acta Cryst. (2009). B65, 86-95    [ doi:10.1107/S0108768108041827 ]

Probing the shapes of chiral bis-(o-naphthalimidobenzoyl) systems using X-ray and circular dichroism methods

U. Rychlewska, A. Plutecka, M. Hoffmann, P. Skowronek, K. Gawronska and J. Gawronski

Abstract: CD (circular dichroism) and X-ray investigations have been carried out in order to identify the prevalent conformations and define the forces that determine the molecular and supramolecular organization of the alkyl-bridged bichromophoric [NAB, ortho-(1,8-naphthalimido)benzoyl] units, each consisting of the benzoyl substituted in the ortho position with the 1,8-naphthalimide group. The results reveal that NAB bichromophores incorporated into the same molecule exist in a variety of conformation/helicity combinations. The molecular structures are largely stabilized by local 1,3-CH/CO dipole-dipole interactions, while the crystal packing besides dispersive H...H interactions is mostly governed by multiple C-H...O(=C) and C-H...[pi] interactions. The relatively small contribution of [pi]...[pi] interactions comes from a pairwise off-face stacking between naphthalimide rings or from pairwise carbonyl...[pi] interactions. All these types of intermolecular interactions have been summarized quantitatively by means of a Hirshfeld surface analysis.

Keywords: 1,8-naphthalimides; chiral diols and amines; weak hydrogen bonds; dipole-dipole interactions; circular dichroism.


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Structure factor file (CIF format) (138.0 kbytes)
[ doi:10.1107/S0108768108041827/so50181sup2.hkl ]
Contains datablock 1


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Structure factor file (CIF format) (146.9 kbytes)
[ doi:10.1107/S0108768108041827/so50182sup3.hkl ]
Contains datablock 2


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Structure factor file (CIF format) (174.4 kbytes)
[ doi:10.1107/S0108768108041827/so50183sup4.hkl ]
Contains datablock 3


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Structure factor file (CIF format) (184.8 kbytes)
[ doi:10.1107/S0108768108041827/so50184sup5.hkl ]
Contains datablock 4


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