guest solvent. After storage for 12 h at room temperature, the
supported by the DFG. S. A. is grateful for a scholarship from
crystals which formed were collected. The host–guest stoichio-
metric ratios were determined by H NMR integration. Data
this organization.
1
for each compound are given in Table 1.
References
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Crystallography
Sample preparation, structure solution and refinement. Single
crystals of diffraction quality of pure 1 were obtained by
dissolving the host in benzene and those of 4 and 5 in acetonitrile
and ethanol, respectively. The inclusion compounds of the
host 2 were obtained by offering an excess of the correspond-
ing picoline isomer. The additional guest acetone being
accommodated is due to the crystallization of 2 from acetone
although the host compound was dried. Therefore the inclusion
compound 7 has 2-picoline and acetone as guests, 8 has
3-picoline and acetone, and 9 4-picoline and acetone, while 6
includes dimethyl sulfoxide only. Since all of the inclusion
compounds, except 5 and 6, proved labile, the crystals were
measured under low temperature conditions on a CAD 4
diffractometer using Cu-Kα radiation (1.5418 Å) for 1, 4–6
and Mo-Kα radiation (0.71073 Å) for 7–9. During the data
collection three reference reflections were monitored period-
ically to check crystal stability. Crystal data and structural
refinements for inclusion compounds of 1 are given in Table 2
and of 2 in Table 3. All structures were solved by direct methods
using SHELX-8620 and refined by full matrix least-squares with
SHELX-93.21 For all structures host non-hydrogen atoms were
treated anisotropically. The hydrogen atoms were subjected to
constrained refinement, with isotropic temperature factors
given to hydrogen atoms of the same kind. The disorder of the
DMSO molecules in 6 and the picoline molecules in 7–9 is
responsible for the high R-values given in Table 3.
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Supplementary data. Lists of fractional atomic coordinates
with isotropic (for H atoms) or equivalent isotropic displace-
ment parameters (for C and O atoms), and of covalent bond
distances and bond angles (Tables 5–25) have been deposited as
supplementary data at the Cambridge Crystallographic Data
Centre.† Further experimental details as well as lists of the
anisotropic displacement parameters (Tables 26–32) and of
the Fobs Ϫ Fcalc values are available directly from one of the
authors (E. W.)
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Thermal analysis
Simultaneous and isothermal differential scanning calorimetry
(DSC) and thermogravimetry (TG) were performed on a
TG-DSC 111 (SETARAM) using open aluminium crucibles,
sample weights of about 4 mg, a linear heating rate of 5 K
minϪ1 and argon at 1 l hϪ1 as purge gas for all measurements.
Crystals were taken from the mother liquor, blotted dry on filter
paper, and transferred into the crucibles for weighing and
measuring.
Acknowledgements
E. W. is grateful to the Fond der Chemischen Industrie for
financial support. This work is part of the Graduate School
Program (GRK 208) of the TU Bergakademie Freiberg,
17 The Crystal as a Supramolecular Entity, ed. G. R. Desiraju, in
Perspectives in Supramolecular Chemistry, Wiley, Chichester, 1996.
18 E. Weber, R. Haase, R. Pollex and M. Czugler, J. Prakt. Chem.,
1999, 341, 274.
19 W. J. Moran, E. C. Schreiber and E. Engel, J. Am. Chem. Soc., 1952,
74, 127.
20 G. M. Sheldrick, SHELX 86, Acta Crystallogr., Sect. A, 1990, 46,
467.
21 G. M. Sheldrick, SHELX 93. A Program for Crystal Structure
Determination, unpublished results.
suppdata/p2/b0/b008451o/ for crystallographic files in .cif or other
electronic format.
1218
J. Chem. Soc., Perkin Trans. 2, 2001, 1212–1218