Skip to main content
SpringerLink
Log in

Supramolecular architecture of azachalcagenene crystals with aromatic substituents

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

Intermolecular interactions in crystals of various azachalcagenenes with aromatic substituents, including polyfluorinated derivatives, are first analyzed and systematized. A topological analysis of crystal packing is carried out, and main supramolecular motifs are identified.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. T. Chivers, A Guide to Chalcogen-Nitrogen Chemistry, World Scientific, New Jersey (2005), p. 318.

    Google Scholar 

  2. N. N. Greenwood and A. Earnshow Chemistry of the Elements, Butterworth-Heinemann (1997), p. 1340.

  3. I. Yu. Bagryanskaya, Yu. V. Gatilov, and A. V. Zibarev, J. Struct. Chem., 38, No 5, 829 (1997).

    Article  CAS  Google Scholar 

  4. K. Awaga, T. Tanaka, and T. Shirai, C. R. Chimie, 10, 52 (2007).

    CAS  Google Scholar 

  5. M. Deumal, S. LeRoux, J. M. Rawson, et al., Polyhedron, 26, 1949 (2007).

    Article  CAS  Google Scholar 

  6. J. M. Rawson, A. Alberola, and A. Whalley, J. Mater. Chem., 16, 2560 (2006).

    Article  CAS  Google Scholar 

  7. J. L. Brusso, K. Cvrkalj, A. A. Leitch, et al., J. Am. Chem. Soc., 128, 15080 (2006).

    Article  CAS  Google Scholar 

  8. I. V. Vlasyuk, V. A. Bagryansky, N. P. Gritsan, et al., Phys. Chem. Chem. Phys., 3, 409 (2001).

    Article  CAS  Google Scholar 

  9. A. A. Leitch, R. W. Reed, C. M. Robertson, et al., J. Am. Chem. Soc., 129, 7903 (2007).

    Article  CAS  Google Scholar 

  10. A. A. Leitch, J. L. Brusso, K. Crvkalj, et al., Chem. Commun., 3368 (2007).

  11. T. S. Cameron, A. Decken, R. M. Kowalczyk, et al., ibid., 2277 (2006).

  12. A. Decken, S. M. Mattar, J. Passmore, et al., Inorg. Chem., 45, 3878 (2006).

    Article  CAS  Google Scholar 

  13. E. Z. Kurmaev, A. I. Poletaev, V. I. Anisimov, et al., Physica C., 321, 191 (1999).

    Article  CAS  Google Scholar 

  14. A. J. Banister and I. B. Gorrell, Adv. Mater., 10, 1415 (1998).

    Article  CAS  Google Scholar 

  15. M. M. Labes, P. Love, and L. F. Nichols, Chem. Rev., 79, 1 (1979).

    Article  CAS  Google Scholar 

  16. V. N. Ikorskii, I. G. Irtegova, E. Lork, et al., Eur. J. Inorg. Chem., 3061 (2006).

  17. A. Yu. Makarov, I. G. Irtegova, N. V. Vasilieva, et al., Inorg. Chem., 44, 7194 (2005).

    Article  CAS  Google Scholar 

  18. W. D. S. Motherwell, H. L. Ammon, J. D. Dunitz, et al., Acta Crystallogr., B58, 647 (2002).

    Article  CAS  Google Scholar 

  19. A. Modelli, V. Venuti, F. Scagnolari, et al., J. Phys. Chem. A, 105, 219 (2001).

    Article  CAS  Google Scholar 

  20. J. M. Rawson and J. J. Longridge, Chem. Soc. Rev., 26, 53 (1997).

    Article  CAS  Google Scholar 

  21. A. V. Zibarev, A. O. Miller, Yu. V. Gatilov, and G. G. Furin, Heteroat. Chem., 443 (1990).

  22. O. J. Scherer, G. Wolmershaeuser, and R. Jotter, Z. Naturforsch., TeilB, 37, 432 (1982).

    Google Scholar 

  23. J. Marten, W. Seicher, et. al., Cryst. Eng. Commun., 10, 541 (2008).

    CAS  Google Scholar 

  24. P. M. Zorkii, Soros. Obraz. Zh., 7, No. 1, 53 (2001).

    Google Scholar 

  25. A. L. Spek, J. Appl. Crystallogr., 36, No. 1, 7 (2003); C. F. Macrae, P. R. Edgington, P. McCabe, et al., ibid., 39, No. 3, 453 (2002).

    Article  CAS  Google Scholar 

  26. R. S. Rowland and R. Taylor, J. Phys. Chem., 100, 7384 (1996).

    Article  CAS  Google Scholar 

  27. F. H. Allen, Acta Crystallogr., B58, 380 (2002).

    CAS  Google Scholar 

  28. B. Moulton and J. Zaworotko, Chem. Rev., 101, 1629 (2001).

    Article  CAS  Google Scholar 

  29. Ch. A. Hunter and J. K. M. Sanders, J. Am. Chem. Soc., 112, 5525 (1990).

    Article  CAS  Google Scholar 

  30. N. Sandblom, T. Ziegler, and T. Chivers, Inorg. Chem., 37, 354 (1998).

    Article  CAS  Google Scholar 

  31. T. Chivers, X. Gao, and M. Parvez, ibid., 35, 9 (1996).

    Article  CAS  Google Scholar 

  32. G. Leandri, V. Busetti, G. Valle, and M. Mammi, J. Chem. Soc. D, 413 (1970).

  33. V. Busetti, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 38, 665 (1982).

    Article  Google Scholar 

  34. A. Gieren and F. Pertlik, Eur. Crystallogr. Meeting, 303 (1974).

  35. H. Munsterer, G. Kresze, V. Lamm, and A. Gieren, J. Org. Chem., 48, 833 (1983).

    Google Scholar 

  36. I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, and A. V. Zibarev, Mendeleev Commun., 167 (1994).

  37. I. Yu. Bagryanskaya, Yu. V. Gatilov, and A. V. Zibarev, J. Struct. Chem., 40, No. 4, 640 (1999).

    Article  CAS  Google Scholar 

  38. I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, and A. V. Zibarev, Mendeleev Commun., No. 4, 136 (1994).

    Article  Google Scholar 

  39. I. Yu. Bagryanskaya, Yu. V. Gatilov, and A. V. Zibarev, ibid., 157.

  40. A. Yu. Makarov, I. Yu. Bagryanskaya, Yu. V. Gatilov, et al., Heteroat. Chem., 12, No. 7, 563 (2001).

    Article  CAS  Google Scholar 

  41. E. Lork, R. Mews, M. M. Shakirov, et al., Eur. J. Inorg. Chem., 2123 (2001).

  42. A. Gieren, H. Betz, T. Hubner, et al., Z. Anorg. Allg. Chem., 513, 160 (1984).

    Article  CAS  Google Scholar 

  43. V. Busetti, G. Cevasco, and G. Leandri, Z. Kristallogr., 197, 41 (1991).

    CAS  Google Scholar 

  44. M. Herberhold, S. Gerstmann, and W. Milius, Phosphorus, Sulfur, Silicon, Relat. Elem., 112, 261 (1996).

    Article  CAS  Google Scholar 

  45. E. Lork, R. Mews, M. M. Shakirov, et al., J. Fluor. Chem., 115, 165 (2002).

    Article  CAS  Google Scholar 

  46. I. Yu. Bagryanskaya, Yu. V. Gatilov, E. Lork, et al., ibid., 116, 149.

  47. T. Maaninen, H. M. Tuononen, K. Kosunen, et al., Z. Anorg. Allg. Chem., 630, 1947 (2004).

    Article  CAS  Google Scholar 

  48. T. Maaninen, R. Laitinen, and T. Chivers, Chem. Commun., 1812 (2002).

  49. R. Jones, D. J. Williams, P. T. Wood, and J. D. Woollins, Polyhedron, 8, 91 (1989).

    Article  CAS  Google Scholar 

  50. A. Yu. Makarov, E. Lork, R. Mews, and A. V. Zibarev, J. Fluor. Chem., 127, 437 (2006).

    Article  CAS  Google Scholar 

  51. A. V. Zibarev, Yu. V. Gatilov, I. Yu. Bagryanskaya, et al., Polyhedron, 11, 2787 (1992).

    Article  CAS  Google Scholar 

  52. I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, and A. V. Zibarev, J. Struct. Chem., 37, No. 2, 318 (1996).

    Article  Google Scholar 

  53. A. Yu. Makarov, I. Yu. Bagryanskaya, F. Blockhuys, et al., Europ. J. Inorg. Chem., No. 1, 77 (2003).

    Article  Google Scholar 

  54. I. Yu. Bagryanskaya, Yu. V. Gatilov, M. M. Shakirov, and A. V. Zibarev, Mendeleev Commun., No. 5, 167 (2002).

    Article  CAS  Google Scholar 

  55. J. Leitch, S. C. Nyburg, D. A. Armitage, and M. J. Clark, J. Cryst. Mol. Struct., 3, 337 (1973).

    Article  CAS  Google Scholar 

  56. F. P. Olsen and J. C. Barrick, Inorg. Chem., 12, 1353 (1973).

    Article  CAS  Google Scholar 

  57. K. Tersago, I. Yu. Bagryanskaya, Yu. V. Gatilov, et al., Europ. J. Inorg. Chem., 1958 (2007).

  58. K. Tersago, M. Mandado, Ch. Van Alsenoy, et al., Chem. Eur. J., 11, No. 15, 4544 (2005).

    Article  CAS  Google Scholar 

  59. A. V. Zibarev, A. O. Miller, Yu. V. Gatilov, and G. G. Furin, Heteroat. Chem., 443 (1990).

  60. H. W. Roesky, J. Sundermeyer, M. Noltemeyer, et al., Z. Naturforsch., B: Chem. Sci., 41, 53 (1986).

    Google Scholar 

  61. M. Witt, H. W. Roesky, M. Noltemeyer, et al., Angew. Chem., Int. Ed., 20, 974 (1981).

    Article  Google Scholar 

  62. G. Wolmershauser and P. R. Mann, Z. Naturforsch., B: Chem. Sci., 46, 315 (1991).

    Google Scholar 

  63. F. Blockhuys, N. P. Gritsan, A. Yu. Makarov, et al., Eur. J. Inorg. Chem., 655 (2008).

  64. A. F. Cozzolino, J. F. Britten, and I. Vargas-Baca, Cryst. Growth Des., 6, 181 (2006).

    Article  CAS  Google Scholar 

  65. A. F. Cozzolino, I. Vargas-Baca, S. Mansour, and A. H. Mahmoudkhani, J. Am. Chem. Soc., 127, 3184 (2005).

    Article  CAS  Google Scholar 

  66. I. Yu. Bagryanskaya, E. V. Bartashevich, D. K. Nikulov, et al., J. Struct. Chem., 50, No. 1, 127–136 (2009).

    Article  CAS  Google Scholar 

  67. H. W. Roesky, E. Wehner, E.-J. Zehnder, et al., Chem. Ber., 111, 1670 (1978).

    Article  CAS  Google Scholar 

  68. K. Ono, S. Tanaka, and Y. Yamashita, Angew. Chem., Int. Ed., 33, 1977 (1994).

    Article  Google Scholar 

  69. M. Karikomi, C. Kitamura, S. Tanaka, and Y. Yamashita, J. Am. Chem. Soc., 117, 6791 (1995).

    Article  CAS  Google Scholar 

  70. J. L. Brusso, O. P. Clements, R. C. Haddon, et al., ibid., 126, 8256 (2004).

    Article  CAS  Google Scholar 

  71. A. Gieren, H. Betz, T. Hubner, et al., Z. Naturforsch., B: Chem. Sci., 39, 485 (1984).

    Google Scholar 

  72. A. Gieren, V. Lamm, R. C. Haddon, et al., ibid., 39, 975 (1984).

    Google Scholar 

  73. T. M. Barclay, A. W. Cordes, R. C. Haddon, et al., J. Am. Chem. Soc., 121, 969 (1999).

    Article  CAS  Google Scholar 

  74. T. M. Barclay, A. W. Cordes, N. A. George, et al., ibid., 120, 352 (1998).

    Article  CAS  Google Scholar 

  75. M. S. Khan, B. Ahrens, M. F. Mahon, et al., Acta Crystallogr., Sect. E: Struct. Rep. Online, 58, 1202 (2002).

    Article  CAS  Google Scholar 

  76. S. Tanaka, M. Tomura, and Y. Yamashita, Heterocycles, 37, 693 (1994).

    Article  CAS  Google Scholar 

  77. R. Jones, J. L. Morris, A. W. Potts, et al., Chem. Commun., 398 (1985).

  78. P. W. Codding, H. Koenig, and R. T. Oakley, Can. J. Chem., 61, 1562 (1983).

    Article  CAS  Google Scholar 

  79. V. V. Zhivonitko, A. Yu. Makarov, I. Yu. Bagryanskaya, et al., Eur. J. Inorg. Chem., 4099 (2005).

  80. A. W. Cordes, M. Hojo, H. Koenig, et al., Inorg. Chem., 25, 1137 (1986).

    Article  CAS  Google Scholar 

  81. A. V. Zibarev, Yu. V. Gatilov, ans A. O. Miller, Polyhedron, 11, 1137 (1992).

    Article  CAS  Google Scholar 

  82. I. Yu. Bagryanskaya, Yu. V. Gatilov, A. Yu. Makarov, et al., Heteroat. Chem., 10, No. 2, 113 (1999).

    Article  CAS  Google Scholar 

  83. A. Yu. Makarov, S. N. Kim, N. P. Gritsan, et al., Mendeleev Commun., No. 1, 14 (2005).

    Article  CAS  Google Scholar 

  84. I. Yu. Bagryanskaya, H. Bock, Yu. V. Gatilov, et al., Chem. Ber. Recueil., 130, 247 (1997).

    Article  CAS  Google Scholar 

  85. A. Yu. Makarov, M. M. Shakirov, K. V. Shuvaev, et al., Chem. Commun., No. 18, 1774 (2001).

    Article  Google Scholar 

  86. A. Yu. Makarov, K. Tersago, K. Nivesanond, et al., Inorg. Chem., 45, 2221 (2006).

    Article  CAS  Google Scholar 

  87. I. Yu. Bagryanskaya, Yu. V. Gatilov, A. O. Miller, et al., Heteroat. Chem., 5, 561 (1994).

    Article  CAS  Google Scholar 

  88. A. C. Gomes, G. Biswas, A. Banerjee, and W. L. Duax, Acta Crystallogr., Sect. C: Crystallogr. Struct. Commun., 45, 73 (1989).

    Article  Google Scholar 

  89. M. Mellini and S. Merlino, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 32, 1074 (1976).

    Article  Google Scholar 

  90. N. L. Klimasenko, L. A. Chetkina, and G. A. Gol’der, J. Struct. Chem, 14, 469–474 (1973).

    Article  Google Scholar 

  91. T. Ueda, Y. Shibata, J. Sakakibara, et al., Chem. Pharm. Bull., 30, 3424 (1982).

    CAS  Google Scholar 

  92. T. Suzuki, T. Tsuji, T. Okubo, et al., J. Org. Chem., 66, 8954 (2001).

    Article  CAS  Google Scholar 

  93. M. Velusamy, K. R. J. Thomas, J. T. Lin, et al., Tetrahedron Lett., 46, 7647 (2005).

    Article  CAS  Google Scholar 

  94. A. Gieren, V. Lamm, and R. C. Haddon, Z. Naturforsch., B: Chem.Sci., 39, 975 (1984).

    Google Scholar 

  95. A. Gieren, V. Lamm, R. C. Haddon, and M. L. Kaplan, J. Am. Chem. Soc., 102, 5070 (1980).

    Article  CAS  Google Scholar 

  96. V. Bertini, P. Dapporto, F. Lucchesini, et al., Acta Crystallogr., Sect. C: Crystallogr. Struct. Commun., 40, 653 (1984).

    Article  Google Scholar 

  97. R. Neidlein, D. Knecht, A. Gieren, and C. Ruiz-Perez, Z. Naturforsch., B: Chem. Sci., 42, 84 (1987).

    CAS  Google Scholar 

  98. O. V. Grineva and P. M. Zorkii, Zh. Fiz. Khim., 74, No. 11, 1937 (2000).

    CAS  Google Scholar 

  99. T. V. Rybalova and I. Yu. Bagryanskaya, J. Struct. Chem., 50, No. 4, 741–753 (2009).

    Article  CAS  Google Scholar 

  100. J. H. Williams, Acc. Chem. Res., 26, 593 (1993).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, Russia

    I. Yu. Bagryanskaya

Authors
  1. I. Yu. Bagryanskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to I. Yu. Bagryanskaya.

Additional information

Original Russian Text Copyright © 2009 by I. Yu. Bagryanskaya

Translated from Zhurnal Strukturnoi Khimii, Vol. 50, Supplement, pp. S182–S195, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bagryanskaya, I.Y. Supramolecular architecture of azachalcagenene crystals with aromatic substituents. J Struct Chem 50 (Suppl 1), 176–189 (2009). https://doi.org/10.1007/s10947-009-0206-9

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10947-009-0206-9

Keywords

Search

Navigation