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RESEARCH FRONT
Contents Vol 65(7)

Pendent Nucleophiles on Coordination Complexes: Hydrogen-Bond Donor and Acceptor Ability*

Jack K. Clegg A B , Jack M. Harrowfield C F , Yang Kim D , Young Hoon Lee D , Augustin Madalan C , Pierre Thuéry E and Arim Woo D
+ Author Affiliations
- Author Affiliations

A School of Chemistry, F11, The University of Sydney, NSW 2006, Australia.

B Department of Chemistry, University of Cambridge, Lensfield Rd, Cambridge, CB2 1EW, UK.

C Institut de Science et d’Ingénierie Supramoléculaires, Université de Strasbourg, 8, allée Gaspard Monge, 67083 Strasbourg, France.

D Department of Chemistry & Advanced Materials, Kosin University, 149-1, Dongsam-dong, Yeongdo-gu, Busan, 606-701, South Korea.

E CEA, IRAMIS, UMR 3299 CEA/CNRS, SIS2M, LCCEf, Bâtiment 125, 91191 Gif-sur-Yvette, France.

F Corresponding author. Email: harrowfield@unistra.fr

Australian Journal of Chemistry 65(7) 734-749 https://doi.org/10.1071/CH11447
Submitted: 24 November 2011  Accepted: 13 December 2011   Published: 16 February 2012

Abstract

Analysis of the crystal structures of a variety of transition metal complexes in which the ligands are hypodentate, thus providing pendent ammonio, amino, and/or hydroxy groups, has been conducted with the objective of defining the labile interactions of these pendent groups. In the case of pendent ammonio groups, not only do they appear to be good H-bond donors but they are frequently involved in contacts suggestive of hyperdenticity at N. For pendent amino and hydroxy groups, of particular interest in regard to their potential activity as nucleophiles, their H-bond acceptor ability frequently seems to be rather limited and it is unclear whether it can be related to either the nature or the charge on the bound metal cation.


References

[1]  (a) R. E. Mewis, S. J. Archibald, Coord. Chem. Rev. 2010, 254, 1686.For a recent spectrum of perspectives on this subject, see:
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmvFOiur0%3D&md5=3ec348a2e33c9968e64cabd4a36fa5f0CAS |
      (b) K. L. Haas, K. J. Franz, Chem. Rev. 2009, 109, 4921.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) L. Fabbrizzi, J. Chem. Educ. 2008, 85, 1501.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) K. L. Fromm, Coord. Chem. Rev. 2008, 252, 856.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) C. G. Oliveri, P. A. Ulmann, M. J. Wiester, C. A. Mirkin, Acc. Chem. Res. 2008, 41, 1618.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) A. Credi, H. Tian, Adv. Funct. Mater. 2007, 17, 679.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) K. Matsumoto, B. Saito, T. Katsuki, Chem. Commun. 2007, 3619.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) R. K. O. Sigel, A. M. Pyle, Chem. Rev. 2007, 107, 97.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) J.-C. G. Bünzli, Acc. Chem. Res. 2006, 39, 53.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) A. G. Blackman, C. R. Chim. 2005, 8, 107.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlOgtrY%3D&md5=c077b5ef12058727e44581f7a384a8f9CAS |
      (b) E. C. Constable, Prog. Inorg. Chem. 1994, 42, 67.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) N. E. Leadbeater, M. Marco, Chem. Rev. 2002, 102, 3217.See, for example,
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xnt1Sjurw%3D&md5=d5927d74e99781f877903bd97fe01c84CAS |
      (b) D. De Vos, M. Dams, B. F. Sels, P. A. Jacobs, Chem. Rev. 2002, 102, 3615.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  A. Torrisi, R. G. Bell, C. Mellot-Draznieks, Cryst. Growth Des. 2010, 10, 2839 .and references therein
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXntFyqtLg%3D&md5=17931033e1175f6ff6566871e024a07dCAS |

[5]  X. Chen, J. I. Brauman, J. Am. Chem. Soc. 2008, 130, 15038.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1GksrjI&md5=4d6d51f34a3bcf5e8a9bf94b944f3f04CAS |

[6]  J. M. Harrowfield, D. Matt, J. Incl. Phenom. Macrocycl. Chem. 2004, 50, 133.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXns12ntA%3D%3D&md5=d2390376779c4c0c04145e81961be408CAS |

[7]  A. M. Sargeson, Chem. Brit. 1979, 15, 23; Pure Appl. Chem. 1984, 56, 1603; Pure Appl. Chem. 1986, 58, 1511; Chem. Aust. 1991, 58, 176.

[8]  I. J. Clark, A. Crispini, P. S. Donnelly, L. M. Engelhardt, J. M. Harrowfield, S.-H. Jeong, Y. Kim, G. A. Koutsantonis, Y. H. Lee, N. A. Lengkeek, M. Mocerino, G. L. Nealon, M. I. Ogden, Y. C. Park, C. Pettinari, L. Polanzan, E. Rukmini, A. M. Sargeson, B. W. Skelton, A. N. Sobolev, P. Thuéry, A. H. White, Aust. J. Chem. 2009, 62, 1246.and references therein
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1KisrfN&md5=c4ecab99dac9d3702ccb1eb98461c960CAS |

[9]  (a) P. S. Donnelly, J. M. Harrowfield, B. W. Skelton, A. H. White, Dalton Trans. 2001, 3078.
         | 1:CAS:528:DC%2BD3MXnsFaksbw%3D&md5=26a3b5bca0a30497fa7ef614790d6432CAS |
      (b) P. S. Donnelly, J. M. Harrowfield, Dalton Trans. 2002, 906.

[10]  (a) C. A. Behm, I. I. Creaser, B. R. Korybut-Daszkiewicz, R. J. Geue, A. M. Sargeson, G. W. Walker, J. Chem. Soc. Chem. Commun. 1993, 1844.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXhtlOksr8%3D&md5=4dcf85f749027c6a5fd089bbe1ac269aCAS |
      (b) C. A. Behm, P. F. L. Boreham, I. I. Creaser, B. R. Korybut-Daszkiewicz, D. J. Maddalena, A. M. Sargeson, G. M. Snowdon, Aust. J. Chem. 1995, 48, 1009.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G. W. Walker, R. J. Geue, A. M. Sargeson, C. A. Behm, J. Chem. Soc., Dalton Trans. 2003, 2992.
      (d) J. M. Harrowfield, G. A. Koutsantonis, G. L. Nealon, B. W. Skelton, A. H. White, Eur. J. Inorg. Chem. 2005, 2384.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) J. M. Harrowfield, G. A. Koutsantonis, H.-B. Kraatz, G. L. Nealon, G. A. Orlowski, B. W. Skelton, A. H. White, Eur. J. Inorg. Chem. 2007, 2384.
      (f) G. A. Koutsantonis, G. L. Nealon, C. E. Buckley, M. Paskevicius, L. Douce, J. M. Harrowfield, A. W. McDowall, Langmuir 2007, 23, 11986.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) J. M. Harrowfield, G. A. Koutsantonis, G. L. Nealon, B. W. Skelton, M. A. Spackman, CrystEngCommun 2009, 11, 249.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) B. Dittrich, J. M. Harrowfield, G. A. Koutsantonis, G. L. Nealon, B. W. Skelton, Dalton Trans. 2010, 3433.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  (a) A. M. Sargeson, Coord. Chem. Rev. 1996, 151, 89.
         | 1:CAS:528:DyaK28XjsVOntbs%3D&md5=921b86c892a5dcaab2ddacbad014e055CAS |
      (b) J. M. Harrowfield, G. A. Koutsantonis, N. A. Lengkeek, B. W. Skelton, A. H. White, Inorg. Chem. 2010, 49, 3152.and references therein
         | Crossref | GoogleScholarGoogle Scholar |

[12]  P. V. Bernhardt, A. M. T. Bygott, R. J. Geue, A. J. Hendry, B. R. Korybut-Daszkiewicz, P. A. Lay, J. R. Pladziewicz, A. M. Sargeson, A. C. Willis, Inorg. Chem. 1994, 33, 4553.and references therein
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXmsVCisb8%3D&md5=0673735a68b3145c187dd96cd345e799CAS |

[13]  (a) P. S. Donnelly, J. M. Harrowfield, B. W. Skelton, A. H. White, Inorg. Chem. 2000, 39, 5817.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXotFWisrw%3D&md5=d3d785a7797f5c51c54495f571c2e4caCAS |
      (b) P. S. Donnelly, J. M. Harrowfield, B. W. Skelton, A. H. White, Inorg. Chem. 2001, 40, 5645.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  J. M. Harrowfield, Supramol. Chem. 2006, 18, 125.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xlt1Sqtbg%3D&md5=83f8564506da7f3ebf904152ab5ddd6dCAS |

[15]  P. V. Bernhardt, J. H. Cho, J. M. Harrowfield, J. Y. Kim, Y. Kim, P. Sujandi, P Thuéry, D. C Yoon, Polyhedron 2006, 25, 1811.and references therein
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XktlynsbY%3D&md5=a6f3043de58fe3958e5b83595562696fCAS |

[16]  (a) P. V. Bernhardt, J. M. Harrowfield, Y. Kim, Y. H. Lee, Y. C. Park, P. Sujandi, Bull. Korean Chem. Soc. 2007, 28, 589.
         | 1:CAS:528:DC%2BD2sXls1Oqt7c%3D&md5=b4653fd01d62f9865865927a406b6cd3CAS |
      (b) P. V. Bernhardt, Y. Kim, P Sujandi, Aust. J. Chem. 2006, 59, 783.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) P. V. Bernhardt, J. Y. Kim, Y. Kim, Y. H. Lee, C. R. Sujandi, C. R. Chim. 2005, 8, 211.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. M. Harrowfield, Y. Kim, G. A. Koutsantonis, Y. H. Lee, P. Thuéry, Inorg. Chem. 2004, 43, 1689.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  J. K. Clegg, L. F. Lindoy, P. Thuéry, Y. H. Lee, D. K. A. Kusumohastuti, C. Mora, H. H. Kim, J. H. Kwo, Y. Kim, J. Incl. Phenom. Macrocycl. Chem. 2009, 65, 49.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtFCisbvL&md5=b903a43294adfe26cfb2f8e5b59a2feaCAS |

[18]  B. Bosnich, C. K. Poon, M. L. Tobe, Inorg. Chem. 1965, 4, 1102.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2MXktlOjtbo%3D&md5=71725a88ea6a805e4edcd3aa20640e66CAS |

[19]  (a) R. Taylor, O. Kennard, J. Am. Chem. Soc. 1982, 104, 5063.For broad ranging discussions, see, for example:
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38Xlt1Kqs7c%3D&md5=dc3ae61eb45b7d71b3d485051e62037dCAS |
      (b) G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. Henry, ChemPhysChem 2002, 3, 561.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) M. A. Spackman, J. A. McKinnon, CrystEngCommun 2002, 4, 378.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. A. Spackman, D. Jayatilaka, CrystEngCommun 2009, 11, 19.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  (a) A. D. Buckingham, J. E. Del Bene, S. A. C. McDowell, Chem. Phys. Lett. 2008, 463, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFWnurzO&md5=24cebcda95ca5319f8f674cae19c68d5CAS |
      (b) S. A. C. McDowell, A. D. Buckingham, J. Am. Chem. Soc. 2005, 127, 15515.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  D. R. Turner, M. Henry, C. Wilkinson, G. J. McIntyre, S. A. Mason, A. E. Goeta, J. W. Steed, J. Am. Chem. Soc. 2005, 127, 11063.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXmt1WktLc%3D&md5=c5ef2c5a7d25eae884f62783e6baf1daCAS |

[22]  Y. H. Lee, A. Woo, J. Y. Choi, J. C. Byun, J. M. Harrowfield, W. T. Lim, P. Thuéry, Y. Kim, J. Incl. Phenom. Macrocycl. Chem. 2011, 71, 395.and references therein
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVGqt7rL&md5=990c1abcb41623bc6f7eb124ea764d04CAS |

[23]  H. Ogino, Inorg. Chem. 1980, 19, 1619.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXksFGisr8%3D&md5=9a3e8d475ac094f8fbc58eb1d2017d70CAS |

[24]  C. Bazzicalupi, A. Bencini, A. Bianchi, A. Danesi, E. Faggi, C. Giorgi, S. Santarelli, B. Valtancoli, Coord. Chem. Rev. 2008, 252, 1052.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXkvVGkt70%3D&md5=ae8d68642467dae68c3a5d7a2a496406CAS |

[25]  P. V. Bernhardt, R. Bramley, L. M. Engelhardt, J. M. Harrowfield, D. C. R. Hockless, B. R. Korybut-Daszkiewicz, E. R. Krausz, T. Morgan, A. M. Sargeson, B. W. Skelton, A. H. White, Inorg. Chem. 1995, 34, 3589.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXmt12lt7o%3D&md5=2412092d8467eddf0cf88c9abf454676CAS |

[26]  A. R. Stefankiewicz, J.-M. Lehn, Chem. – Eur. J. 2009, 15, 2500.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsVOlurg%3D&md5=39d4521c3e4e9362b7efd2e4f475a184CAS |

[27]  R. L. Fanshawe, A. Mobinikhaledi, C. R. Clark, A. G. Blackman, Inorg. Chim. Acta 2000, 307, 27.
         | Crossref | GoogleScholarGoogle Scholar |

[28]  D. A. House, P. J. Steel, Inorg. Chim. Acta 1999, 288, 53.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXjtVegtrY%3D&md5=9bc75688614a0bdf6f94368bb2414714CAS |

[29]  N. J. Lundin, I. G. Hamilton, A. G. Blackman, Polyhedron 2004, 23, 97.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtVWjt73L&md5=a3ca7509fb4ca0296164004c64685b31CAS |

[30]  A. Zimmer, D. Kuppert, T. Weyhermüller, I. Müller, K. Hegetschweiler, Chem. – Eur. J. 2001, 7, 917.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhsFWjur4%3D&md5=37a83a8d57ecb840ad681621411a7158CAS |

[31]  H. W. Smith, W. J. Stratton, Inorg. Chem. 1977, 16, 1640.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2sXksVKrtrc%3D&md5=a38a30e0a493a25b3054b5ea21a10081CAS |

[32]  P. Vaqueiro, Acta Crystallogr. 2006, E62, o2632.
         | 1:CAS:528:DC%2BD28XmsF2ltrs%3D&md5=456fb9482a46c2102d84328e83405317CAS |

[33]  J. M. Harrowfield, G. A. Koutsantonis, G. L. Nealon, B. W. Skelton, A. H. White, Eur. J. Inorg. Chem. 2005, 2384.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlvFWjur4%3D&md5=6cbc44cec5f558ad37d2334004631b99CAS |

[34]  J. M. Harrowfield, G. A. Koutsantonis, G. L. Nealon, B. W. Skelton, M. A. Spackman, CrystEngCommun 2009, 11, 249.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhvVWlurk%3D&md5=4709f3dcee50b0d79dd112f2a7d0c945CAS |

[35]  L. M. Engelhardt, L. Grøndahl, J. M. Harrowfield, S. F. Ralph, A. M. Sargeson, B. W. Skelton, A. N. Sobolev, A. H. White, J. Incl. Phenom. Macrocycl. Chem. 2011, 71, 353.
         | 1:CAS:528:DC%2BC3MXhsVGqt7vE&md5=038c8ac2768741368a1dd788f76a08c8CAS |

[36]  J. Harrowfield, J. Y. Kim, Y. Kim, Y. H. Lee, P. Sujandi, P Thuéry, Polyhedron 2005, 24, 968.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXks1altLg%3D&md5=9bb538a8fd0ee3fa713d8fa8e463a436CAS |

[37]  P. V. Bernhardt, J. M. Harrowfield, Y. Kim, Y. H. Lee, Y. C. Park, P. Sujandi, Bull. Korean Chem. Soc. 2007, 28, 589.
         | 1:CAS:528:DC%2BD2sXls1Oqt7c%3D&md5=b4653fd01d62f9865865927a406b6cd3CAS |

[38]  J. M. Harrowfield, Y. Kim, G. A. Koutsantonis, Y. H. Lee, P. Thuéry, Inorg. Chem. 2004, 43, 1689.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVyqtLk%3D&md5=53d9ec9ce23401354a4886a3a2279dbeCAS |

[39]  P. V. Bernhardt, G. A. Lawrance, W. C. Patalinghug, B. W. Skelton, A. H. White, N. F. Curtis, A. Siriwardena, J. Chem. Soc., Dalton Trans. 1990, 2853.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXhtFeqsLc%3D&md5=f84040ed88b6454f0106254695c1ae0fCAS |

[40]  P. V. Bernhardt, G. A. Lawrance, Coord. Chem. Rev. 1990, 104, 297.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXmt1ehurw%3D&md5=52100438d38f89d6f90e19d5d77798e2CAS |

[41]  G. A. Lawrance, B. W. Skelton, A. H. White, P. Comba, Aust. J. Chem. 1986, 39, 1101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XmtFOrs7Y%3D&md5=95c4fd9a8d67e7fab4481e30fa210563CAS |

[42]  P. V. Bernhardt, L. A. Jones, P. C. Sharpe, J. Chem. Soc., Dalton Trans. 1997, 1169.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXivVCmtLg%3D&md5=4509e7482288f9fc8aab0806344855cdCAS |

[43]  P. Comba, I. I. Creaser, L. R. Gahan, J. M. Harrowfield, G. A. Lawrance, L. L. Martin, A. H. W. Mau, A. M. Sargeson, W. H. F. Sasse, M. R. Snow, Inorg. Chem. 1986, 25, 384.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XhtVWit70%3D&md5=2d1a74dd062bb0e36239feed6c3e5debCAS |

[44]  J. M. Harrowfield, Y. Kim, B. W. Skelton, A. H. White, Aust. J. Chem. 1995, 48, 807.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlt1Wlsrk%3D&md5=9edafbae5e41dfdf2092024b5923df67CAS |

[45]  J. M. Harrowfield, G. A. Koutsantonis, G. L. Nealon, B. W. Skelton, A. H. White, Eur. J. Inorg. Chem. 2005, 2384.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlvFWjur4%3D&md5=6cbc44cec5f558ad37d2334004631b99CAS |

[46]  (a) D. A. House, Helv. Chim. Acta 1985, 68, 1872.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28Xht1Wrur0%3D&md5=89ab15ac5b2968fdb626610c9491a67cCAS |
      (b) V. McKee, M. Harnett, D. A. House, Inorg. Chim. Acta 1985, 102, 83.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. A. Watson, M. R. Prinsep, D. A. House, Inorg. Chim. Acta 1986, 115, 95.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) D. A. House, Inorg. Chem. 1986, 25, 1671.
         | Crossref | GoogleScholarGoogle Scholar |

[47]  V. Amendola, L. Fabbrizzi, E. Mundum, P. Pallvicini, Dalton Trans. 2003, 773.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhsVaksL8%3D&md5=3509f6606f7e1bb91a6e6c49cbe2d192CAS |

[48]  J. M. Harrowfield, M. I. Ogden, B. W. Skelton, A. H. White, C. R. Chim. 2005, 8, 121.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtlOgtrc%3D&md5=15fb36109851d5be4496a2a3e7958745CAS |

[49]  P. M. Zorky, O. V. Grineva, J. Incl. Phenom. Macrocycl. Chem. 2004, 48, 81.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtlWru74%3D&md5=6d43c8a6b8355f50012cd305118da0feCAS |

[50]  H. F. Bauer, W. C. Drinkard, J. Am. Chem. Soc. 1960, 82, 5031.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3MXjs1ylsw%3D%3D&md5=d5be016303c35e09b57413a151192d5eCAS |

[51]  M. Shibata, Top. Curr. Chem. 1983, 110, 26.
         | Crossref | GoogleScholarGoogle Scholar |

[52]  G. A. Bottomley, I. J. Clark, I. I. Creaser, L. M. Engelhardt, R. J. Geue, K. S. Hagen, J. M. Harrowfield, G. A. Lawrance, P. A. Lay, A. M. Sargeson, A. H. See, B. W. Skelton, A. H. White, F. R. Wilner, Aust. J. Chem. 1994, 47, 143.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXjtFChtrc%3D&md5=2faadda001937a671d21d040ea18904cCAS |

[53]  Kappa-CCD Software 1998 (Nonius BV: Delft, The Netherlands).

[54]  Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXivFehsbw%3D&md5=8d3d2b169b325c8c890be4769cf7844fCAS |

[55]  G. M. Sheldrick, Acta Crystallogr. A 2008, 64, 112.
         | Crossref | GoogleScholarGoogle Scholar |

[56]  APEX v2.1, SAINT v.7 and XPREP v.6.14 2003 (Bruker AXS Inc.: Madison, WI).

[57]  L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXlsVSlurk%3D&md5=a99bb00e596a61480b8be4159291b3beCAS |

[58]  A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giocavazzo, A. Guagliardi, A. G. C. Moliterni, G. Polidori, S. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhsFOrsbo%3D&md5=c4e408e0a44f946ddf3ece761180471cCAS |

[59]  G. M. Sheldrick, SADABS: Empirical Absorption and Correction Software, University of Göttingen, Germany, 1999–2007.