2
S. C. Zimmerman, Z. Zeng, W. Wu and D. E. Reichert, J. Am.
Chem. Soc., 1991, 113, 183 and references therein; S. C. Zimmer-
man, W. Wu and Z. Zeng, ibid., 1991, 113, 196; S. C. Zimmerman
and W. Wu, ibid., 1989, 111, 8054; S. C. Zimmerman, M. Mrksich
and M. Baloga, ibid., 1989, 111, 8528; R. Shimazawa, Y. Hash-
imoto and S. Iwasaki, T etrahedron L ett., 1992, 33, 7197.
J. P. Fillers, K. G. Ravichandran, A. Abdalmuhdi, A. Tulinsky
and C. K. Chang, J. Am. Chem. Soc., 1986, 108, 417.
(CH ), 70.31 (CH ), 112.46 (2 ArCH), 118.93 (4 ArCH), 140.46
2
2
(2 ArC), 148.01 (4 ArC), 169.80 (CH CO); IR (KBr) l \ 3434,
2
3311 (NÈH), 1696 (C2O), 1540, 1345 (NO ) cm~1; MS (FAB):
2
m/z 553.0 [M ] H]` (552.1 calcd for C
H
N O ); elem.
20 20
6
13
anal. for C
H
N O É H O (570.43): calcd C 42.11, H 3.89,
20 20
6
13
2
N 14.73; found C 42.04, H 3.81, N 14.58%.
3
4
5
6
M. J. Gunter, M. R. Johnston, B. W. Skelton and A. H. White, J.
Chem. Soc., Perkin T rans. 1, 1994, 1009.
N,Nº-Bis(dimethylisophthalate)-3,6,9-trioxaundecanedicar-
boxamide (3). Dropwise addition of 3,6,9-trioxaundecanedioic
acid dichloride (7.38 g, 28 mmol) in THF (100 mL) to 5-
aminoisophthalic acid dimethyl ester (12.05 g, 57.6 mmol) and
K CO (8.31 g, 60 mmol) in THF (200 mL) gives 3 (5.1 g,
Y. Agnus, M. Gross, M. Labarelle, R. Louis and B. Metz, J.
Chem. Soc., Chem. Commun., 1994, 939.
S. C. Zimmerman, in Bioorganic Chemistry Frontiers, Springer,
Berlin, 1991, vol. 2, 33È71; S. C. Zimmerman, T op. Curr. Chem.,
1993, 165, 71; S. C. Zimmerman, K. W. Saionz and Z. Zeng,
Proc. Natl. Acad. Sci. USA, 1993, 90, 1190.
2
3
30%) as a beige solid having no accurate melting point. 1H
NMR (200 MHz, DMSO-d ):
OCH CH O), 3.87 (s, 12H, OCH ), 4.11 (s, 4H, OCH CO),
8.10 (t, 2H, ArH, J \ 1.5 Hz), 8.45 (d, 4H, ArH, J \ 1.5 Hz),
10.04 (s br, 2H, NH); IR (KBr) l 3313 (NÈH), 1727 (C2O)
cm~1; MS (FAB): m/z 605.1 [M ] H]` (604.2 calcd for
d
3.70 (A B , 8H,
7
J. Rebek, Jr., Angew. Chem. , 1990, 102, 261; Angew. Chem., Int.
Ed. Engl., 1990, 29, 245; R. Guther, M. Nieger and F. Vogtle,
Angew. Chem., 1993, 105, 647; Angew. Chem., Int. Ed. Engl., 1993,
32, 601; M. Harmata, C. L. Barnes, S. R. Karra and S. Elahmad,
J. Am. Chem. Soc., 1994, 116, 8392; A. Lorente, M.
FernandezÈSaiz, J. F. Espinosa, C. Jaime, J. M. Lehn and J. P.
Vigneron, T etrahedron L ett., 1995, 36, 5261; L. J. DÏSouza and
U. Maitra, J. Org. Chem., 1996, 61, 9494.
6
2 2
2
2
3
2
C
H
N O ); elem. anal. for 2C
H
N O É H O
28 32
2
13
28 32
2
13
2
(1227.16): calcd C 54.81, H 5.42, N 4.57; found C 55.44, H
5.54, N 4.42.
8
9
T. Schrader, Chem. Eur. J., 1997, 3, 1537.
F. Cozzi and J. S. Siegel, Pure Appl. Chem., 1995, 67, 683; K.
Miyamura, A. Mihara, T. Fujii, Y. Gohshi and Y. Ishii, J. Am.
Chem. Soc., 1995, 117, 2377; A. S. Shetty, J. Zhang and J. S.
Moore, J. Am. Chem. Soc., 1996, 1181019.
X-Ray structure analyses
1 É 2H O. Colourless prisms, monoclinic, P2 /c, (C5 ) (no. 14),
10 S. Meyer, Ph.D. Dissertation, Universite Louis Pasteur, Stras-
bourg, 1996.
2
1
2h
a \ 11.726(3), b \ 8.518(3), c \ 20.943(6) A, b \ 91.31(2)¡,
U \ 2091(2) A 3, Z \ 4, k(Cu-Ka) \ 7.81 cm~1. All hydrogen
11 M. C. Etter, Acc. Chem. Res., 1990, 23, 120; J. Bernstein, R. E.
Davis, L. Shimoni and N.-L. Chang, Angew. Chem., 1995, 107,
1687; Angew. Chem., Int. Ed. Engl., 1995, 34, 1555; S. Sub-
ramanian and M. J. Zaworotko, Coord. Chem. Rev., 1994, 137,
357; J. P. Glusker, T op. Curr. Chem., 1998, 198, 1; A. Nangia and
G. R. Desiraju, T op. Curr. Chem., 1998, 198, 57; R. E. Melendez
and A. D. Hamilton, T op. Curr. Chem., 1998, 198, 97.
12 G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1991, 426; T. M.
Krygowski, S. J. Grabowski and J. Konarski, T etrahedron, 1998,
11311.
13 R. Parthasarathy, S. Chaturvedi and K. Go, Proc. Natl. Acad.
Sci. USA, 1990, 87, 871; K. R. Rajashankar, S. Ramakumar,
R. M. Jain and V. S. Chauhan, J. Am. Chem. Soc., 1995, 117,
11773.
14 G. R. Desiraju, Chem. Commun., 1997, 1475; G. R. Desiraju,
Angew. Chem., 1995, 107, 2541; Angew. Chem., Int. Ed. Engl.,
1995, 34, 2311; G. R. Desiraju and A. Gavezzotti, J. Chem. Soc.,
Chem. Commun., 1989, 621.
15 F. Vogtle, in Supramolecular Chemistry, Wiley, Chichester, 1991;
J.-M. Lehn, in Supramolecular Chemistry, VCH, Weinheim, 1995;
G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N.
Chin, M. Mammen and D. M. Gordon, Acc. Chem. Res., 1995,
28, 37; C. B. Aakeroy, M. Nieuwenhuyzen and S. L. Price, J. Am.
Chem. Soc., 1998, 120, 8986; V. R. Pedireddi, A. Ranganathan
and S. Chatterjee, T etrahedron L ett., 1998, 39, 9831.
16 D. S. Lawrence, T. Jiang and M. Levett, Chem. Rev., 1995, 95,
2229.
17 Y.-L. Chang, M.-A. West, F. W. Fowler and J. W. Lauher, J. Am.
atoms were localized and introduced as Ðxed contributions
with isotropic thermal parameters set to 1.3 times those of the
atoms to which they were bonded. R \ 0.034, Rw \ 0.047, for
2111 observed reÑections (F2 [ 3p(F2)). The weighting scheme
0
0
was deÐned by the Killean and Lawrence method with terms
of 0.02 and 3.0.38
2 É H O. Pale yellow prisms, monoclinic, P2 /c, (C5 )
2
1
2h
(no. 14), a \ 7.994(1), b \ 21.670(3), c \ 14.741(3) A,
b \ 101.91(1)¡, U \ 2499(1)
A 3, Z \ 4, k(Cu-Ka) \ 10.88
cm~1. All hydrogen atoms were located on di†erence Fourier
syntheses maps and included as Ðxed contributions with iso-
tropic thermal parameters 1.3 times those of the atoms to
which they were bonded. Anisotropic temperature factors for
all non-hydrogen atoms; R \ 0.049, Rw \ 0.045, for 3267
reÑections (F2 [ 3p(F2)).
0
0
3 É 0.5H O. Pale yellow prisms, triclinic, P1, (C1) (no. 2),
2
i
a \ 11.318(2), b \ 24.444(5), c \ 11.069(1) A, a \ 96.17(1),
b \ 101.24(1), c \ 77.23(2)¡; U \ 2923(1) A
3, Z \ 2, asym-
metric unit formula 2 (C
H
N O ) É H O, k(Cu-Ka) \ 9.12
28 32
2
13
2
cm~1. The Killean and Lawrence method with terms of 0.02
and 0.4 was used to deÐne the weights.38 Final R \ 0.052,
Rw \ 0.059, for 6597 reÑections (F2 [ 3p(F2)). Anisotropic
temperature factors were used for all non-hydrogen atoms.
Hydrogen atom treatment: included in di†erence map or cal-
0
0
Chem. Soc., 1993, 115, 5991.
culated positions (d
showed a large thermal motion. This was treated as a disorder
over two alternative positions.
\ 0.95 A). An ether O of one ligand
18 M. C. T. Fyfe and J. F. Stoddart, Acc. Chem. Res., 1997, 30, 393;
D. Philp and J. F. Stoddart, ibid., 1996, 108, 1242; ibid., 1996, 35,
1154; D. B. Amabilino and J. F. Stoddart, Chem. Rev., 1995, 95,
2725.
19 H. Ringsdorf, B. Schlarb and J. Venzmer, Angew. Chem., 1988,
100, 117; Angew. Chem., Int. Ed. Engl., 1988, 27, 113; R. B.
Gennis, in Biomembranes: Molecular Structure and Function,
SpringerÈVerlag, New York, 1989; T. Dewa, S. J. Vigmond and
S. L. Regen, J. Am. Chem. Soc., 1996, 118, 3435.
20 Y. Umezawa, S. Tsuboyama, K. Honda, J. Uzawa and M. Nishio,
Bull. Chem. Soc. Jpn., 1998, 71, 1207.
ChH
suppdata/nj/b0/b001127o/ for crystallographic Ðles in .cif
format.
Acknowledgements
21 G. R. Desiraju, Acc. Chem. Res., 1996, 29, 441; C. V.
KrishnamohanÈSharma and M. J. Zaworotko, Chem. Commun.,
1996, 2655; T. Steiner, Chem. Commun., 1997, 727; I. Berger and
M. Egli, Chem. Eur. J., 1997, 3, 1400; S. G. Bodige, R. D. Rogers
and S. C. Blackstock, Chem. Commun., 1997, 1669; K. N. Houk,
S. Mentzer, S. P. Newton, F. M. Raymo, J. F. Stoddart and D. J.
Williams, J. Am. Chem. Soc., 1999, 121, 1479; G. R. Desiraju and
T. Steiner, in T he W eak Hydrogen Bond in Structural Chemistry
and Biology, Oxford University Press, Oxford, 1999.
S.M. is grateful to the Centre National de la Recherche Scien-
tiÐque (CNRS) and the Region Alsace for a PhD fellowship.
We thank Dr. D. Moras and Professor J. Fischer for the use
of their X-ray facilities.
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