P. Nagy et al. / Journal of Molecular Structure 606 (2002) 61±76
75
somewhat near the sulfur atoms and two weak
S(VI)´´´O(methoxy) nonbonded contacts of 3.16 and
Ê
3.30 A are formed both as a part of a linear
OyS(VI)´´´O(methoxy) sequence (Table 9).
However, it is striking to note that the sulfone
groups in 4 do not disrotate as in the heterocyclic
bis-sulfone 8. This phenomenon may be explained
by the formation of two additional S(VI)´´´O(sul-
fonyl) close contacts which join the two halves of
the molecule and are assisted by linear C(ar)±
S(VI)´´´O(sulfonyl) bridges (Table 9). Here, the
3.4. Intermolecular distances
The intermolecular distances observed for
compounds 1±4 are signi®cantly longer than the
sum of the van der Waals radii showing that there
no longer exists any intermolecular S´´´S and S´´´O
close contacts, which might control the actual mole-
cular conformations. The minimum intermolecular
Ê
S´´´S distances for 1±4: .6, .6, .6 and 5.397 A,
respectively; while the minimum intermolecular
S´´´O distances for 2±4: 4.774(1), 4.853(4) and
Ê
4.342(2) A, respectively. The aromatic rings in two
Ê
nonbonded distances are 2.89 and 3.02 A. It should
neighboring molecules are also too far from each
other to contribute to the geometries observed.
be noted that S(VI)´´´O close contacts of 1,5 type were
registered only in few cases in the literature (2.91±
Ê
3.22 A, cf. Refs. [1,6±8]). The nonbonded distances
observed earlier were not far from the sum of the van
Ê
der Waals radii (3.25 A), and thus they proved to be
Acknowledgements
signi®cantly longer than the S(II)´´´O and S(IV)´´´O
distances.
Â
The X-ray data were collected by Mr Csaba Kertesz
who deserves the thanks from the authors. The work
was supported by the Hungarian Research Foundation
OTKA T029799, OTKA 033086 and OTKA
T034985.
The S(VI)´´´O(methoxy) contacts close in both
parts of the molecule a ®ve-membered ring. Owing
to the turning out of the methoxycarbonyl groups from
the plane of the phenyl groups, these rings are far from
being favorably planar (cf. Ref. [1]). The torsion
angles for the four-atom sections in the S±C(ar)±
C(ar)±C(sp2)±O(methoxy) sequences are 12/12, 61/
52, 254/250, 54/49, 230/2298, starting from the
S1/ S2 atoms. The ®ve-membered rings with O(3)
and O(4) atoms assume a twisted envelope form char-
acterized by the puckering parameters [31] Q3
References
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Â
[2] A. Kucsman, I. Kapovits, in: F. Bernardi, I.G. Csizmadia, A.
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     Â
[3] S. Solyom, P. Sohar, L. Toldy, A. Kalman, L. Parkanyi, Tetra-
ꢀ
ꢀ
0:786ꢀ3 A; F3 332:2ꢀ28 and Q4 0:712ꢀ3 A;
F4 332:7ꢀ28; respectively.
hedron Lett. (1977) 4245.
 Â
On the contrary, the S(VI)´´´O(sulfonyl) close
contacts lead to the formation of a distorted six-
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an S(VI)´´´O contact of 1,6 type. The four-atom
sections of the rings with an S±C(ar)±C(ar)±C(ar)±
S0 ±O0 sequence may be characterized by the torsional
angles 24/27, 27/24, 12/7, 252/247, 77/72 and 255/
2568, starting from the S1/S2 atoms. The puckering
parameters for the stretched rings with O(5) and O(6)
 Â
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Â
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Â
Â
Â
Â
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Â
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Â
Â
Â
Â
È
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Â
   Â
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Â
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Â
   Â
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Â
[9] A. Kucsman, I. Kapovits, M. Czugler, L. Parkanyi, A. Kalman,
Â
Â
Â
Â
ꢀ
atoms are Q5 0:831ꢀ3 A; u5 58:8ꢀ1 F5
J. Mol. Struct. 198 (1989) 339.
 Â
[10] J. Rabai, I. Kapovits, I. Jalsovszky, Gy. Argay, A. Kalman,
ꢀ
339:5ꢀ28 and Q6 0:898:3ꢀ3 A; u6 58:5ꢀ1 F6
Â
Â
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 Â
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Â
Â
T. Koritsanszky, J. Chem. Soc. Perkin Trans. 2 (1997) 1045.
Â
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Â
 Â
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Â
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 Â
Parkanyi, J. Mol. Struct. 300 (1993) 23.