Abstract
A comparative study of the molecular geometry and crystal packing of crown-containing styryl heterocycles and their dimethoxy substituted analogues is performed. It is established that all the compounds exhibit an identical type of distortions of the geometry of the central styryl fragment. These are the localization of the π-electron density at the ethylene bond and the bond alternation in a half of the phenyl ring due to the conjugation of lone electron pairs of the oxygen substituents with the chromophore system of the molecule. A comparative analysis of the crystal packings of the compounds reveals extended separate hydrophilic and hydrophobic regions. The hydrophilic regions are built of crown ether fragments, and the hydrophobic regions consist of π-conjugated and aromatic molecular fragments. The hydrophobic regions are characterized by a wide variety of packing motifs, among which stacking packing is absent. For two compounds, the formation of sandwich dimers that are preorganized to enter into the photochemical [2 + 2]cycloaddition reaction is observed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. G. Kuz’mina, A. V. Churakov, J. A. K. Howard, et al., Kristallografiya 48(4), 664 (2003) [Crystallogr. Rep. 48, 613 (2003)].
Cation Binding by Macrocycles, Ed. by Y. Inoue and G. W. Gokel (Marcel Dekker, New York, 1990), p. 1.
R. M. Izatt, K. Pawlak, J. S. Bradshaw, and R. L. Bruening, Chem. Rev. 91, 1721 (1991).
A. T. Yordanov and D. M. Roundhill, Coord. Chem. Rev. 170, 93 (1998).
K. Gloe, H. Graubaum, M. Wüst, et al., Coord. Chem. Rev. 222, 103 (2001).
P. Bühlmann, E. Pretsch, and E. Bakker, Chem. Rev. 98, 1593 (1998).
Comprehensive Supramolecular Chemistry, Ed. by D. N. Reinhoudt (Pergamon, Oxford, 1996), p. 267.
V. Balzani, A. Credi, and M. Venturi, Coord. Chem. Rev. 171, 3 (1998).
S. P. Gromov and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim. 46, 611 (1997).
M. Takeshita, C. F. Soong, and M. Irei, Tetrahedron Lett. 39, 7717 (1998).
S. H. Kawai, Tetrahedron Lett. 39, 4445 (1998).
I. K. Lednev, R. E. Hester, and J. N. Moore, J. Phys. Chem. A 101, 7371 (1997).
I. K. Lednev, T.-Q. Ye, R. E. Hester, and J. N. Moore, J. Phys. Chem. A 101, 4966 (1997).
I. K. Lednev, R. E. Hester, and J. N. Moore, J. Am. Chem. Soc. 119, 3456 (1997).
R. Bergonzi, L. Fabrizzi, M. Licchelli, and M. Mangano, Coord. Chem. Rev. 170, 31 (1998).
L. F. Lindoy, Coord. Chem. Rev. 174, 327 (1998).
V. Balzani, A. Credi, and M. Venturi, Coord. Chem. Rev. 171, 3 (1998).
S. P. Gromov and M. V. Alfimov, Izv. Akad. Nauk, Ser. Khim. 46, 611 (1997).
O. A. Fedorova, E. N. Andryukhina, A. V. Lindeman, et al., Izv. Akad. Nauk, Ser. Khim., No. 2, 302 (2002).
Yu. V. Fedorov, O. A. Fedorova, N. É. Shepel’, et al., Izv. Akad. Nauk, Ser. Khim., 1718 (2005).
E. N. Andryukhina, M. M. Mashura, O. A. Fedorova, et al., Izv. Akad. Nauk, 1650 (2005).
O. A. Fedorova, Y. V. Fedorov, E. N. Andryukhina, et al., Org. Lett. 5, 4533 (2003).
Yu. V. Fedorov, O. A. Fedorova, E. N. Andryukhina, et al., New J. Chem. 27, 280 (2003).
SAINT: Version 6.02A (Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, USA, 2001).
G. M. Sheldrick, SHELXTL-Plus: Release 5.10 (Bruker Analytical X-ray Systems Inc., Madison, Wisconsin, USA, 1997).
Comprehensive Supramolecular Chemistry, Ed. by J. M. Lehn (Pergamon, New York, 1996).
M. D. Cohen and G. M. Schmidt, J. Chem. Soc., 1996 (1964).
M. D. Cohen, G. M. Schmidt, and F. I. Sonntag, J. Chem. Soc., 2000 (1964).
G. M. Schmidt, J. Chem. Soc., 2014 (1964).
G. M. Schmidt, Pure Appl. Chem. 27, 647 (1971).
V. Ramamurthy and K. Venkatesan, Chem. Rev. 87, 433 (1987).
L. R. MacGillivray, Cryst. Eng. Commun. 7, 1 (2002)
T. Friščič and L. R. MacGillivray, J. Chem. Soc., Chem. Commun., No. 11, 1306 (2003).
O. Shigeru and I. Yoshikatsu, Acta Crystallogr., Sect. B: Struct. Sci. 59, 149 (2003).
H. Kazumasa, Bull. Chem. Soc. Jpn. 75, 2384 (2002).
M. B. Hursthouse and M. Motevalli, J. Phys. Chem. 85, 3636 (1981).
Y. Ohashi, Acta Crystallogr. A: Fundam. Crystallogr. 54, 842 (1998).
K. Honda, F. Nakanishi, and N. Feeder, J. Am. Chem. Soc. 121, 8246 (1999).
H. Hosomi, S. Ohba, K. Tanaka, and F. Toda, J. Am. Chem. Soc. 122, 1818 (2000).
I. Turowska-Tyrk, Chem.—Eur. J. 7, 3401 (2001).
I. Turowska-Tyrk, Chem. Phys. Lett. 361, 115 (2002).
H. Nalanishi, W. Jones, J. M. Thomas, and K. Honda, Bull. Chem. Soc. Jpn. 75, 2383 (2002).
S. Ohba and I. Yoshikatsu, Acta Crystallogr., Sect. B: Struct. Sci. 59, 149 (2003).
G. R. Desiraju, J. Chem. Soc., Chem. Commun., No. 16, 1475 (1997).
M. V. Alfimov, A. V. Churakov, Y. V. Fedorov, et al., J. Chem. Soc., Perkin Trans. 2, 2249 (1997).
K. Müller-Dethlefs and P. Hobza, Chem. Rev. 100, 143 (2000).
C. Juniak, J. Chem. Soc., Dalton Trans., 3885 (2000).
Comprehensive Supramolecular Chemistry, Ed. by J. Atwood (Pergamon, Oxford, 1996), Vol. 6, p. 1.
A. I. Vedernikov, S. P. Gromov, N. A. Lobova, et al., Izv. Akad. Nauk, Ser. Khim., No. 8, 1869 (2005).
Author information
Authors and Affiliations
Additional information
Original Russian Text © L.G. Kuz’mina, O.A. Fedorova, E.N. Andryukhina, M.M. Mashura, S.P. Gromov, M.V. Alfimov, 2006, published in Kristallografiya, 2006, Vol. 51, No. 3, pp. 467–480.
Rights and permissions
About this article
Cite this article
Kuz’mina, L.G., Fedorova, O.A., Andryukhina, E.N. et al. Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues. Crystallogr. Rep. 51, 434–447 (2006). https://doi.org/10.1134/S1063774506030126
Received:
Issue Date:
DOI: https://doi.org/10.1134/S1063774506030126