Helvetica Chimica Acta ± Vol. 87 (2004)
1535
Experimental Part
Synthesis. The 3,4,5,6-tetrahydrophthalic anhydride (1) was prepared by complete isomerization of a pure
sample of cis-1,2,3,6-tetrahydrophthalic anhydride (m.p. 376 K) at 473 K, with P as acid catalyst according to
Bailey and Amstutz [19]. Subsequent purification by recrystallization from anh. cyclohexane yielded pure 1.
2
O
5
1
13
M.p. 357 K, H-NMR (CDCl
CH
); 68.12 (s, CC); 87.86( s, 2 CO).
Colorless crystals were obtained by slow evaporation of a dilute soln. of pure samples of 1 in anh.
3
): 1.5 (m, 2 CH
2
), 2.5 (m, 2 CH
2
). C-NMR (CDCl
3
): À56.41 (s, 2 CH ); À56.27 (s,
2
2
2
cyclohexane at r.t. in a dry-box.
X-Ray Structure Determination. As the crystals were hygroscopic, the single crystal used was mounted in a
thin-walled glass capillary of the Lindemann type during data collection. The intensity data were collected at 150 K
on a Nonius four-circle diffractometer equipped with a CCD bidimensional detector and an Oxford Cryostream
crystal-cooling system. Crystal data, details of data collection, and structure refinement are summarized in Table 4.
Intensities were corrected for Lorentz and polarization effects. No absorption corrections were applied. The
structure was solved by direct methods with the SIR92 program [20] and refined by the full-matrix least-squares
method, based on F, by using the teXsan software [21]. The refinement was performed with anisotropic temperature
factors for all non-H-atoms. H-Atoms were refined isotropically. A correction for secondary extinction [22] was
À6
applied with a value of the extinction parameter equal to 1.0(2)¥10 . The pictures of the crystal structure are shown
in Figs. 1, 3, and 4. The ORTEPII program [23] was used to produce the asymmetric unit of the structure (Figs. 1),
while the Cerius2 software [24] was applied to represent the molecular arrangement (Figs. 3 and 4). Crystallo-
graphic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre, as
the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: 441223336033; e-mail: deposit@ccdc.cam.ac.uk).
REFERENCES
[
[
[
[
[
[
[
[
[
1] A. Ben Fredj, S. Ben Rejeb, F. Ben Amor, A. Driss, Acta Crystallogr.,Sect. C 1998, 54, 1710.
2] B. D. Nageswara Rao, J. D. Baldeschwieler, J. Mol. Spectrosc. 1963, 11, 440.
3] H. Werner, E. Kleinpeter, A. Zschunke, G. Mann, J. Org. Magn. Reson. 1973, 5, 179.
4] A. Ben Fredj, S. Ben Rejeb, J. Soc. Chim. Tunisie 1999, IV, 575.
5] A. Ben Fredj, S. Ben Rejeb, N. JaÔdane, Z. Ben Lakhdar, J. Mol. Struct. (Theochem). 2000, 219.
6] W. H. Watson, P. R. Kashyap, Acta Crystallogr.,Sect. C 1985, 41, 1226.
7] D. L. Evans, W. T. Robinson, Acta Crystallogr.,Sect. B 1977, 33, 2891.
8] A. Ben Fredj, M. Bagieu, S. Ben Rejeb, M. Rzaigui, unpublished results.
9] R. Bucourt, D. Hainaut, Bull. Soc. Chim. 1967, 4562.
[
[
[
[
[
[
[
10] R. Bucourt, Bull. Soc. Chim. 1964, 2080.
11] A. Ben Fredj, Th e¡ se de Doctorat en Chimie-Physique, Facult e¬ des Sciences de Tunis, Tunisie, 2000.
12] J. H. Chiang, S. H. Bauer, J. Am. Chem. Soc. 1969, 1898.
13] R. E. Marsh, E. Ubell, H. L. Wilcox, Acta Crystallogr. 1962, 15, 35.
14] M. Ehrenberg, Acta Crystallogr. 1965, 19, 698.
15] A. Kirfel, Acta Crystallogr., Sect. B 1975, 31, 2494.
16] M. Cossu, C. Bachmann, T. Y. N×Guessan, R. Viani, J. Lapasset, J.-P. Aycard, H. Bodot, J. Org. Chem. 1987,
52, 5313.
[
[
17] A. I. Kitalgorodsky, −Organic Chemical Crystallography×, New York, 1961.
18] G. R. Desiraju, T. Steiner, in −The Weak Hydrogen Bond in Structural Chemistry and Biology×, Oxford
University Press, Oxford, UK, 1999, p. 1.
[
[
19] M. E. Bailey, E. D. Amstutz, J. Am. Chem. Soc. 1956, 78, 3828.
20] A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, −SIR92 ± A Program for Automatic Solution of
Crystal Structures by Direct Methods×, J. Appl. Crystallogr. 1993, 26, 343.
[
21] Molecular Structure Corporation, −TeXsan for Windows. Single Crystal Structure Analysis Software.
Version 1.06×, MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA, 1997 ± 2001.
22] W. H. Zachariasen, Acta Crystallogr. 1967, 23, 558.
[
[
[
23] C. K. Johnson, −ORTEPII. Report ORNL-5138×, Oak Ridge National Laboratory, Tennessee, USA, 1976.
24] −Cerius2 Software. Version 4.2 MatSci.×, Molecular Simulations Inc., 9685 Scranton Road, San Diego,
California, USA 92121-3752, 2000.
Received January 28,2004