E. Wagner-Wysiecka et al. / Tetrahedron 67 (2011) 1862e1872
1871
1.5 Hz); 7.91e7.97 (6H, m); 8.12 (2H, d, J¼8.3 Hz). IR (film): 2923;
2877; 1598; 1599; 1520; 1126; 1041; 926; 759 cmꢂ1. HRMS (EI):
[M]þ¼658.11620 calculated for C32H26N4O8S2 658.11921.
a stock solution was placed in a 10 mL flask and diluted with the
solvent. To the ligand solution, 100-fold excess of the metal salt
solution was added and the fluorescence spectrum was registered.
Measurements were repeated three times and the obtained results
were averaged.
4.3.10. Compound 13. To dinitropodand 12 (0.32 g, 0.46 mmol) in
30 mL of mixture ethanol and water (1:1) ferric dust (0.278 g,
4.6 mmol) was added. To a boiling mixture acetic acid (0.14 mL) was
added and refluxing was continued for 17 h. After that, the mixture
was extracted with methylene chloride. The extract was concen-
trated and chromatographed on column using a mixture of meth-
ylene chloride and acetone (10:1), to give 0.23 g (80%) of an oily
product. TLC (methylene chlorideeacetone, 10:1) Rf¼0.20. 1H NMR
Acknowledgements
M.S.F. thanks the Foundation for Polish Science (FNP) and Mia-
nowski Fund for received grant. The authors kindly acknowledged
support from sources for science in years 2008e2010, Grant No. N
N204 223834. Authors thank Jaros1aw Chojnacki Ph.D., D.Sc. for
X-ray measurements.
(CDCl3),
d
[ppm]: 3.77 (4H, s); 3.91 (4H, t, J¼4.4 Hz); 4.31 (4H, t,
J¼4.4 Hz); 4.4 (4H, br s); 6.72 (2H, d, J¼8.3 Hz); 7.32 (2H, t,
J¼7.6 Hz); 7.45 (2H, t, J¼7.6 Hz); 7.48 (2H, dd, J¼7.8 and 1.4 Hz);
7.68 (2H, s); 7.84 (2H, d, J¼7.8 Hz); 8.00 (2H, d, J¼7.8 Hz). IR (film):
3461; 3350; 1617; 1303; 1247; 1140; 933; 876; 752 cmꢂ1. HRMS
(EI): [M]þ¼598.16968 calculated for C32H30N4O4S2 598.17085.
Supplementary data
Supplementary data associated with this article can be found in
4.4. X-ray crystallographic studies
Crystals of 1$H2O and 4$H2O suitable for X-ray crystallography
were grown by slow evaporation from acetone solutions. X-ray
measurements for 1$H2O and 4$H2O were carried out on a KUMA
KM4 four-axis diffractometer equipped with a Sapphire-2 CCD
detector (Oxford Diffraction). The monocrystal was thermostated at
120 K in a nitrogen flow (Oxford Cryosystem). Data collection:
CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis
RED (Oxford Diffraction, 2005);22 data reduction: CrysAlis RED;
program used to solve structure: SHELXS97; program used to refine
structure: SHELXL97.23 No absorption corrections were applied
because of negligible influence of absorption on intensity of
References and notes
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2004, 48, 125e130.
6. Kapor, S.; Sapre, A. V.; Kumar, S.; Mashraqui, S. H.; Mukherjee, T. Chem. Phys.
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7. Hama, H.; Morozumi, T.; Nakamura, H. Tetrahedron Lett. 2007, 48, 1859e1861.
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Spectrochim. Acta, Part A 2009, 72, 322e326.
reflections (low
m values). All non-hydrogen atoms were refined
anisotropically. C-bound hydrogen atoms were refined in geo-
metrically idealized positions with isotropic temperature factors
1.2 times the equivalent isotropic temperature factors U equiv of
their attached atoms. N- and O-bound hydrogen atoms were lo-
calized on difference Fourier map and refined in isotropic
approximation.
ꢀ
ꢀ
9. Xie, J.; Menand, M.; Maisonneuve, S.; Metivier, R. J. Org. Chem. 2007, 72,
5980e5985.
10. Powe, A. M.; Das, S.; Lowry, M.; El-Zahab, B.; Fakayode, S. O.; Geng, M. L.; Baker,
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11. Luboch, E.; Bilewicz, R.; Kowalczyk, M.; Wagner-Wysiecka, E.; Biernat, J. F. Ad-
vances in Supramolecular Chemistry: Azo Macrocyclic Compounds; Cerberus:
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12. Wagner-Wysiecka, E.; Luboch, E.; Kowalczyk, M.; Biernat, J. F. Tetrahedron 2003,
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13. Luboch, E.; Wagner-Wysiecka, E.; Fainerman-Melnikova, M.; Lindoy, L. F.;
Biernat, J. F. Supramol. Chem. 2006, 18, 593e601.
Crystal/refinement data for 1$H2O: C30H27N5O5, M¼537.57,
monoclinic, space group P21/c, a¼10.6091(6), b¼10.5637(8),
3
ꢀ
ꢂ
ꢂ
c¼23.9467(13) A,
b
¼98.653(4) , V¼2653.2(3) A , Z¼4, T¼120(2) K,
Dc¼1.346 g cmꢂ3
,
m
(Mo K
a
)¼0.094 mmꢂ1, F(000) 1128, 5182
max¼52.0ꢀ, 370 refined parameters, GOF
ꢀ
14. Wagner-Wysiecka, E.; Jamrogiewicz, M.; Fonari, M. S.; Biernat, J. F. Tetrahedron
2007, 63, 4414e4421.
15. Wagner-Wysiecka, E.; Rzymowski, T.; Luboch, E. Pol. J. Chem. 2008, 82,
unique reflections to 2
q
1.020, R1¼0.0530, wR2¼0.0945 for 3150 observations with I>2
s (I),
R1¼0.1091, wR2¼0.1077 (for all unique data), largest diff. peak and
1299e1302.
3
ꢂ
16. Szczygelska-Tao, J.; Fonari, M. S.; Biernat, J. F. Supramol. Chem. 2008, 20,
651e658.
hole: 0.232 and ꢂ0.203 e/A .
Crystal/refinement data for 4$H2O: C30H29N5O5, M¼539.58,
monoclinic, space group P21/c, a¼10.269(1), b¼9.551(1), c¼26.977
17. (a) Gromov, S. P.; Dmitrieva, S. N.; Vedernikov, A. I.; Kuz’mina, L. G.; Churakov,
A. V.; Strelenko, Y. A.; Howard, J. A. K. Eur. J. Org. Chem. 2003, 3189e3199; (b)
Fedorova, O. A.; Fedorov, Y. V.; Vedernikov, A. I.; Yescheulova, O. V.; Gromov, S.
P.; Alfimov, M. V.; Kuz’mina, L. G.; Churakov, A. V.; Howard, J. A. K.; Zaitsev, S. Y.;
3
ꢂ
(2) A,
b
¼96.87(1)ꢀ,
V¼2626.9(4) A ,
Z¼4,
T¼120(2) K,
ꢂ
Dc¼1.364 g cmꢂ3
,
m
(Mo K
a
)¼0.095 mmꢂ1, F(000) 1136, 4634
€
Sergeeva, T. I.; Mobius, D. New J. Chem. 2002, 26, 543e553.
unique reflections to 2
q
max¼50.30ꢀ, 370 refined parameters, GOF
18. (a) Panneerselvam, K.; Chacko, K. K.; Weber, E.; Kohler, H.-J. J. Inclusion Phenom.
Mol. Recognit. Chem. 1990, 9, 337e347; (b) Weber, E.; Kohler, H.-J.; Reuter, H.
Chem. Ber. 1989, 122, 959e967; (c) Panneerselvam, K.; Sobhia, M. E.; Chacko, K.
K.; Weber, E.; Kohler, H.-J.; Pollex, R. J. Inclusion Phenom. Mol. Recognit. Chem.
1992, 13, 29e36; (d) Reddy, P. J.; Chacko, K. K.; Weber, E.; Kohler, H.-J.; Pollex, R.
Supramol. Chem. 1993, 3, 47e56.
19. For examples of crown ethers encapsulating water molecule see (a) Huszthy, P.;
Vermes, B.; Bathori, N.; Czugler, M. Tetrahedron 2003, 59, 9371e9377; (b) Suh,
I.-H.; Namgung, H.; Ku Yoon, Y.; Saenger, W.; Vogtle, F. J. Inclusion Phenom. Mol.
Recognit. Chem. 1985, 3, 21e26; (c) Bocskei, Z.; Simon, K.; Nemeth, V.; Agai, B.;
Toke, L. Acta Crystallogr. 1996, B52, 194e200; (d) Declercq, J.-P.; Tinant, B.;
Dutasta, J.-P.; Mulatier, J.-C. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 155,
1e14; (e) Huang, F.; Slebodnick, C.; Switek, K. A.; Gibson, H. W. Chem. Commun.
2006, 1929e1932; (f) Luboch, E.; Wagner-Wysiecka, E.; Poleska-Muchlado, Z.;
Kravtsov, V. C. Tetrahedron 2005, 61, 10738e10747; (g) Kraft, D.; Cacciapaglia, R.;
Bohmer, V.; El-Fadl, A. A.; Harkema, S.; Mandolini, L.; Reinhoudt, D. N.; Ver-
boom, W.; Vogt, W. J. Org. Chem. 1992, 57, 826e834; (h) Hiratani, K.; Goto, M.;
Nagawa, Y.; Kasuga, K.; Fujiwara, K. Chem. Lett. 2000, 1364e1366; (i) Palmer, R.
A.; Potter, B. S.; Lisgarten, J. N.; Fenn, R. H.; Mason, S. A.; Mills, O. S.; Robinson,
0.988, R1¼0.0714 for 2222 observations with I>2 (I), R1¼0.1770,
s
wR2¼0.1158 (for all unique data), largest diff. peak and hole: 0.265
3
ꢂ
and ꢂ0.301 e/A .
CCDC 646845 (1$H2O) and CCDC 646846 (4$H2O) contain the
supplementary crystallographic data for this paper. These data may
be obtained free of charge from The Cambridge Crystallographic
4.5. Fluorescence measurements
Stock solution of all reagents (about 10ꢂ4 mol dmꢂ3 for ligands
and about 10ꢂ3 mol dmꢂ3 for metal perchlorates) were prepared by
weighing the appropriate amount of each compound and dissolv-
ing it in an acetonitrile. To prepare working solutions, an aliquot of