Acta Crystallographica Section B

Structural Science

Volume 60, Part 5 (October 2004)

research papers

Acta Cryst. (2004). B60, 609-620 [ doi:10.1107/S0108768104014466 ]

X-ray diffraction and packing analysis on vintage crystals: Wilhelm Koerner's nitrobenzene derivatives from the School of Agricultural Sciences in Milano

F. Demartin, G. Filippini, A. Gavezzotti and S. Rizzato

Abstract: The crystal structures of six nitrotoluene derivatives, synthesized by Wilhelm Koerner about a century ago and retrieved from a depository at the University of Milano, were determined. The correct assignment of molecular structures is verified. The geometry of the nitro groups and factors affecting the orientation of nitro groups with respect to the benzene ring are discussed, also using an auxiliary set of crystal structures retrieved from the Cambridge Structural Database. The crystal packings have been analyzed, and lattice energies have been calculated by atom-atom potential methods and by the newly proposed Pixel method. This method allows a more complete description of intermolecular potentials in terms of the interaction between molecular electron densities and separate Coulombic, polarization, dispersion and overlap repulsion energies. Lattice vibrations and external entropies were calculated by lattice-dynamical procedures. The results of the Pixel energy calculations allow a reliable, quantitative assessment of the relative importance of stacking interactions and hydrogen bonding in the rationalization of the recognition modes of nitrobenzene derivatives, which is impossible to attain using only qualitative atom- atom geometry concepts.

Keywords: nitrobenzene derivatives; Cambridge Structural Database; orientation; stacking interactions.


	Structure factor file (CIF format) (37.3 kbytes) Contains datablock k19

	Structure factor file (CIF format) (144.7 kbytes) Original version: contains datablock k15

	Structure factor file (CIF format) (93.8 kbytes) Corrected version supplied by the author on 16 January 2012: contains datablock k15

	Structure factor file (CIF format) (121.9 kbytes) Original version: contains datablock k20

	Structure factor file (CIF format) (56.4 kbytes) Corrected version supplied by the author on 16 January 2012: contains datablock k20

	Structure factor file (CIF format) (143.8 kbytes) Original version: contains datablock gave6

	Structure factor file (CIF format) (92.4 kbytes) Corrected version supplied by the author on 16 January 2012: contains datablock gave6

	Structure factor file (CIF format) (129.9 kbytes) Original version: contains datablock k12

	Structure factor file (CIF format) (83.7 kbytes) Corrected version supplied by the author on 16 January 2012: contains datablock k12

	Structure factor file (CIF format) (64.3 kbytes) Original version: contains datablock k14

	Structure factor file (CIF format) (37.4 kbytes) Corrected version supplied by the author on 16 January 2012: contains datablock k14

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