(e) N. Srivastava, V. Srivastava and S. M. Verma, Indian
J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 1991, 30, 1080
(a) M. J. Potrzebowski, M. Michalska, A. E. Kozioł, S.
Kaz´mierski, T. Lis, J. Pluskowski and W. Ciesielski, J. Org.
Chem., 1998, 63, 4209; (b) M. J. Potrzebowski, G. Grossmann,
K. Ganicz, S. Olejniczak, W. Ciesielski, A. E. Kozioł, I.
Wawrzycka, G. Bujacz, U. Haeberlen and H. Schmitt, Chem.–
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provides complementary information about molecular dyna-
mics in the crystal lattice although not always in a direct
way. The example of compound 2 with two independent mole-
cules in the unit cell is convincing. The more rigid molecule 2,
with restricted motion due to several CH/p interactions and
the proximity of a large number of protons in the local envir-
onments, reveals a higher cross-polarisation efficiency. Finally,
application of high-field liquid state NMR spectroscopy
7
8
9
The used numeration is convenient for crystal structure and
NMR, but does not conform with the numeration in the names
of the compounds.
1
allowed us to assign all H and 13C signals and to revise the
incorrect assignment of some 13C signals in the older litera-
ture.6e The solute-solvent interactions influence the syn/anti
ratio of conformers in the liquid phase. In the case of chloro-
form the solvent, which participates in CH/p contacts on the
upside face of ring b, restricts the possibility of intramolecular
interactions between the aliphatic residue and aromatic ring b
in the syn conformation and as a consequence, the amount of
anti conformer increases.
E. Weber, S. Finge and I. Cso¨regh, J. Org. Chem., 1991, 56, 7281.
10 B. A. Frenz, SDP–Structure Determination Package, Enraf–
Nonius, Delft, 1984.
11 A. C. T. North, D. C. Philips and F. S. Mathews, Acta Crystal-
logr., Sect. A, 1968, 24, 351.
12 G. M. Sheldrick, G. M. Kruger and R. Goddard, SHELXS-86,
Crystallographic Computing 5, Oxford University Press, Oxford,
1990.
13 G. M. Sheldrick, SHELXL-93, Program for Crystal Structure
Refinement, University of Go¨ttingen, Germany,1993.
14 G. Metz, X. Wu and S. O. Smith, J. Magn. Reson., 1994, 110, 219.
15 A. E. Bennet, C. Rienstra, M. Auger, C. Lakami and R. Griffin,
J. Chem. Phys., 1995, 103, 6951.
Acknowledgements
16 M. Alla and E. Lippmaa, Chem. Phys. Lett., 1976, 37, 260.
17 S. J. Opella and M. H. Frey, J. Am. Chem. Soc., 1979, 101, 5854.
18 J. Witt, D. Fenzke and W. D. Hoffmann, Appl. Magn. Reson.,
1992, 3, 151.
19 WIN-NMR 6.0 Program, Version 960901, Bruker–Franzen
Analytik GmbH, Bremen, 1996.
20 M. Nishio, M. Hirota and Y. Umezawa, in Methods in Stereo-
chemical Analysis, ed. A. P. Marchand, Wiley–VCH, New York,
1998, p. 19 and p. 33.
This work was supported by the Polish Committee for
Scientific Research, KBN, grant no. 3 T09A 02619. GG ack-
nowledges the European Community for financial sup-
port of his one month stay in Lodz under the Centers of
Excellence program.
21 The 12 protons of the dihydroethanoanthracene skeleton appear
in the spectra as three particular spin systems for each conforma-
tion. The aliphatic protons H7/14 and H15/16 on the one hand
and the ring c protons H2/5 and H3/4 on the other hand give
approximately AA0XX0 spin systems, while the signals from the
ring b protons H9/12 and H10/11 must be interpreted as AA0BB0
spin systems. The coupling constants (Hz) of the aliphatic system
in all investigated compounds differ only slightly: 3J(14–15) ¼
8.4(2), 4J(7–15) ¼ ꢂ0.2(1), 3J(15–16) ¼ 8.0(2), and 5J(7–14) ¼
0.0(1). The coupling constants in both aromatic spin systems
were: 3J(2–3 and 9–10) ¼ 7.3(1), 4J(2–4 and 9–11) ¼ 1.3(1),
3J(3–4 and 10–11) ¼ 7.6(1), and 4J(3–5 and 10–12) ¼ 0.6(1).
22 The authors of ref. 6e have made an attempt to assign some 13C
lines to the atoms of compounds 1, 2, 4 and others. Our 2D
spectra show that some of the assumed assignments are not
correct.
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