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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Rage Against Conformity: Ruthenium(ii) Bisterpyridine Complexes Respond to Crystal Engineering Instructions with Whelming Results*

Hasti Iranmanesh A , Kasun S. A. Arachchige A B , William A. Donald A , Niamh Kyriacou A , Chao Shen A , Jason R. Price C and Jonathon E. Beves A D E
+ Author Affiliations
- Author Affiliations

A School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.

B School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

C The Australian Synchrotron, 800 Blackburn Road, Clayton, Vic. 3168, Australia.

D Key State Laboratory for Coordination Chemistry, Nanjing University, Nanjing 210093, China.

E Corresponding author. Email: j.beves@unsw.edu.au

Australian Journal of Chemistry 70(5) 529-537 https://doi.org/10.1071/CH16620
Submitted: 2 November 2016  Accepted: 1 December 2016   Published: 19 January 2017

Abstract

Four heteroleptic ruthenium(ii) complexes of 4′-functionalised 2,2′:6′,2′′-terpyridine are reported, along with their solid-state single-crystal X-ray structures. The complexes feature complementary hydrogen-bond donor (phenol) and acceptor (pyridyl) groups designed to assemble into one-dimensional polymers. In one example, the system obeys the programmed instructions to form a one-dimensional, self-complementary hydrogen-bonded polymer. In one other example, a water-bridged hydrogen-bonded polymer is formed. In the remaining two structures, aryl–aryl interactions dominate the intermolecular interactions, and outweigh the contribution of intermolecular hydrogen bonding.


References

[1]  (a) C. A. Kent, B. P. Mehl, L. Ma, J. M. Papanikolas, T. J. Meyer, W. Lin, J. Am. Chem. Soc. 2010, 132, 12767.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtVOnsr3O&md5=23aa1eed3dc01043ff5037aeee3349dbCAS |
      (b) C. Wang, Z. Xie, K. E. deKrafft, W. Lin, J. Am. Chem. Soc. 2011, 133, 13445.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Zhang, L. Han, L. Li, J. Cheng, D. Yuan, J. Luo, Cryst. Growth Des. 2013, 13, 5466.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) W. A. Maza, S. R. Ahrenholtz, C. C. Epley, C. S. Day, A. J. Morris, J. Phys. Chem. C 2014, 118, 14200.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. Kobayashi, T. Ohba, E. Saitoh, Y. Suzuki, S.-i. Noro, H.-C. Chang, M. Kato, Inorg. Chem. 2014, 53, 2910.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) C. Wang, D. Liu, Z. Xie, W. Lin, Inorg. Chem. 2014, 53, 1331.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) S. Zhang, L. Li, S. Zhao, Z. Sun, J. Luo, Inorg. Chem. 2015, 54, 8375.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) S. Zhang, L. Li, S. Zhao, Z. Sun, M. Hong, J. Luo, J. Mater. Chem. A 2015, 3, 15764.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) A. Watanabe, A. Kobayashi, E. Saitoh, Y. Nagao, M. Yoshida, M. Kato, Inorg. Chem. 2015, 54, 11058.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) A. Kobayashi, Y. Suzuki, T. Ohba, T. Ogawa, T. Matsumoto, S.-i. Noro, H.-C. Chang, M. Kato, Inorg. Chem. 2015, 54, 2522.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) W. A. Maza, R. Padilla, A. J. Morris, J. Am. Chem. Soc. 2015, 137, 8161.
         | Crossref | GoogleScholarGoogle Scholar |
      (l) X. Yu, S. M. Cohen, Chem. Commun. 2015, 9880.
         | Crossref | GoogleScholarGoogle Scholar |
      (m) D. Sun, Y. Gao, J. Fu, X. Zeng, Z. Chen, Z. Li, Chem. Commun. 2015, 2645.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) S. M. Contakes, M. L. Kuhlman, M. Ramesh, S. R. Wilson, T. B. Rauchfuss, Proc. Natl. Acad. Sci. USA 2002, 99, 4889.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XjtFKmsbo%3D&md5=103364fed076146f8bafc7f950798618CAS |
      (b) B. Therrien, G. Süss-Fink, P. Govindaswamy, A. K. Renfrew, P. J. Dyson, Angew. Chem. Int. Ed. 2008, 47, 3773.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) B. Kilbas, S. Mirtschin, R. Scopelliti, K. Severin, Chem. Sci. 2012, 3, 701.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) K. Li, L.-Y. Zhang, C. Yan, S.-C. Wei, M. Pan, L. Zhang, C.-Y. Su, J. Am. Chem. Soc. 2014, 136, 4456.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) A. J. Metherell, M. D. Ward, Chem. Commun. 2014, 6330.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) A. J. Metherell, M. D. Ward, Chem. Commun. 2014, 10979.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) J. Yang, M. Bhadbhade, W. A. Donald, H. Iranmanesh, E. G. Moore, H. Yan, J. E. Beves, Chem. Commun. 2015, 4465.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) K. Wu, K. Li, Y.-J. Hou, M. Pan, L.-Y. Zhang, L. Chen, C.-Y. Su, Nat. Commun. 2016, 7, 10487.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) C. Shen, A. D. W. Kennedy, W. A. Donald, A. M. Torres, W. S. Price, J. E. Beves, Inorg. Chim. Acta 2017, 458, 122.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) J. Yang, J. K. Clegg, Q. Jiang, X. Lui, H. Yan, W. Zhong, J. E. Beves, Dalton Trans. 2013, 15625.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1CmtLjM&md5=c70286208e8871df027559aadc0527d9CAS |
      (b) H. Iranmanesh, M. Bhadbhade, N. De Haas, E. T. Luis, H. Yan, J. Yang, J. E. Beves, Supramol. Chem. 2015, 27, 854.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) J. McMurtrie, I. Dance, CrystEngComm 2005, 7, 216.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltlOqs70%3D&md5=44d2653bee6f44bed4281f17453159f2CAS |
      (b) J. McMurtrie, I. Dance, CrystEngComm 2009, 11, 1141.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. McMurtrie, I. Dance, CrystEngComm 2010, 12, 2700.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. McMurtrie, I. Dance, CrystEngComm 2010, 12, 3207.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) J. E. Beves, E. C. Constable, C. E. Housecroft, C. J. Kepert, M. Neuburger, D. J. Price, S. Schaffner, CrystEngComm 2007, 9, 1073.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtleqtb3E&md5=05bc057c900cb4655ce8d98421057a7cCAS |
      (b) J. E. Beves, E. C. Constable, C. E. Housecroft, C. J. Kepert, D. J. Price, CrystEngComm 2007, 9, 456.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. E. Beves, D. J. Bray, J. K. Clegg, E. C. Constable, C. E. Housecroft, K. A. Jolliffe, C. J. Kepert, L. F. Lindoy, M. Neuburger, D. J. Price, S. Schaffner, F. Schaper, Inorg. Chim. Acta 2008, 361, 2582.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. E. Beves, E. C. Constable, S. Decurtins, E. L. Dunphy, C. E. Housecroft, T. D. Keene, M. Neuburger, S. Schaffner, CrystEngComm 2008, 10, 986.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) J. E. Beves, E. C. Constable, C. E. Housecroft, C. J. Kepert, M. Neuburger, D. J. Price, S. Schaffner, J. A. Zampese, Dalton Trans. 2008, 6742.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) J. E. Beves, E. C. Constable, C. E. Housecroft, M. Neuburger, S. Schaffner, CrystEngComm 2008, 10, 344.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) J. E. Beves, E. C. Constable, C. E. Housecroft, M. Neuburger, S. Schaffner, Polyhedron 2008, 27, 2395.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) J. E. Beves, E. L. Dunphy, E. C. Constable, C. E. Housecroft, C. J. Kepert, M. Neuburger, D. J. Price, S. Schaffner, Dalton Trans. 2008, 386.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) J. E. Beves, E. C. Constable, S. Decurtins, E. L. Dunphy, C. E. Housecroft, T. D. Keene, M. Neuberger, S. Schaffner, J. A. Zampese, CrystEngComm 2009, 11, 2406.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Crystallogr. Sect. B 2016, 72, 171.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28Xls1Kntro%3D&md5=22be3793a59949e4bceffba57de98356CAS |

[7]  M. Khan, V. Enkelmann, G. Brunklaus, Cryst. Growth Des. 2009, 9, 2354.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsFKls7k%3D&md5=cb4495732a568726c731691e4bf0152eCAS |

[8]  (a) L. R. MacGillivray, J. L. Reid, J. A. Ripmeester, J. Am. Chem. Soc. 2000, 122, 7817.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXltF2is78%3D&md5=f0275c4cf4a2093e487a3a1086940380CAS |
      (b) C. Prasang, H. L. Nguyen, P. N. Horton, A. C. Whitwood, D. W. Bruce, Chem. Commun. 2008, 6164.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. Mukherjee, G. R. Desiraju, Chem. Commun. 2011, 4090.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. S. Patil, A. V. Mossine, H. Kumari, C. L. Barnes, J. L. Atwood, Cryst. Growth Des. 2014, 14, 5212.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) N. A. Mir, R. Dubey, S. Tothadi, G. R. Desiraju, CrystEngComm 2015, 17, 7866.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) T. P. Rupasinghe, K. M. Hutchins, B. S. Bandaranayake, S. Ghorai, C. Karunatilake, D.-K. Bucar, D. C. Swenson, M. A. Arnold, L. R. MacGillivray, A. V. Tivanski, J. Am. Chem. Soc. 2015, 137, 12768.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) R. S. Patil, A. M. Drachnik, H. Kumari, C. L. Barnes, C. A. Deakyne, J. L. Atwood, Cryst. Growth Des. 2015, 15, 2781.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) T. P. Rupasinghe, K. M. Hutchins, B. S. Bandaranayake, S. Ghorai, C. Karunatilake, D.-K. Bučar, D. C. Swenson, M. A. Arnold, L. R. MacGillivray, A. V. Tivanski, J. Am. Chem. Soc. 2015, 137, 12768.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) K. M. Hutchins, R. H. Groeneman, E. W. Reinheimer, D. C. Swenson, L. R. MacGillivray, Chem. Sci. 2015, 6, 4717.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) D. P. Ericson, Z. P. Zurfluh-Cunningham, R. H. Groeneman, E. Elacqua, E. W. Reinheimer, B. C. Noll, L. R. MacGillivray, Cryst. Growth Des. 2015, 15, 5744.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) C. R. Pfeiffer, S. G. Atwood, L. Samadello, J. L. Atwood, Cryst. Growth Des. 2015, 15, 2958.
         | Crossref | GoogleScholarGoogle Scholar |
      (l) R. S. Patil, H. Kumari, C. L. Barnes, J. L. Atwood, Chem. Commun. 2015, 2304.
         | Crossref | GoogleScholarGoogle Scholar |
      (m) D. A. Adsmond, A. S. Sinha, U. B. R. Khandavilli, A. R. Maguire, S. E. Lawrence, Cryst. Growth Des. 2016, 16, 59.
         | Crossref | GoogleScholarGoogle Scholar |
      (n) D. A. Adsmond, A. S. Sinha, U. B. R. Khandavilli, A. R. Maguire, S. E. Lawrence, Cryst. Growth Des. 2016, 16, 59.
         | Crossref | GoogleScholarGoogle Scholar |
      (o) C. R. Pfeiffer, K. A. Feaster, S. J. Dalgarno, J. L. Atwood, CrystEngComm 2016, 18, 222.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  J. Wang, G. S. Hanan, Synlett 2005, 1251.

[10]  C. Shen, P. Wang, J. E. Beves, Polyhedron 2016, 103, 241.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXht1elsLvM&md5=0b9d39dfa48750d6bf3112636b891572CAS |

[11]  S. K. Wolff, D. J. Grimwood, J. J. McKinnon, M. J. Turner, D. Jayatilaka, M. A. Spackman, CrystalExplorer 3.1 2013 (University of Western Australia: Crawley, WA). Available at: http://crystalexplorer.scb.uwa.edu.au/

[12]  (a) M. A. Spackman, J. J. McKinnon, CrystEngComm 2002, 4, 378.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmvFKrtrY%3D&md5=04185a2b850995c36beeaecfc91f050aCAS |
      (b) M. A. Spackman, J. J. McKinnon, D. Jayatilaka, CrystEngComm 2008, 10, 377.

[13]  J. J. McKinnon, D. Jayatilaka, M. A. Spackman, Chem. Commun. 2007, 3814.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVCrtLbF&md5=76f39fc53836f220685fd50af7cd04d6CAS |

[14]  J. J. McKinnon, M. A. Spackman, A. S. Mitchell, Acta Crystallogr. Sect. B 2004, 60, 627.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  M. A. Spackman, D. Jayatilaka, CrystEngComm 2009, 11, 19.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVCksg%3D%3D&md5=83196510543882089cd064d14952b1a7CAS |

[16]  E. C. Constable, A. M. W. C. Thompson, J. Chem. Soc., Dalton Trans. 1994, 1409.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXlt1ertbg%3D&md5=2a7d12dd7d0542e22eb6d053db8f3143CAS |

[17]  N. P. Cowieson, D. Aragao, M. Clift, D. J. Ericsson, C. Gee, S. J. Harrop, N. Mudie, S. Panjikar, J. R. Price, A. Riboldi-Tunnicliffe, R. Williamson, T. Caradoc-Davies, J. Synchrotron Radiat. 2015, 22, 187.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitFeitLrO&md5=1fa8616ba4d7c15fb07b883d272d433eCAS |

[18]  T. M. McPhillips, S. E. McPhillips, H.-J. Chiu, A. E. Cohen, A. M. Deacon, P. J. Ellis, E. Garman, A. Gonzalez, N. K. Sauter, R. P. Phizackerley, S. M. Soltis, P. Kuhn, J. Synchrotron Radiat. 2002, 9, 401.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xotleluro%3D&md5=4b06744951e5db9160e97e445120839fCAS |

[19]  W. Kabsch, Acta Crystallogr. Sect. D 2010, 66, 125.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhs1SisLc%3D&md5=7bae66ce10b6a77cc2684bc15139b7eeCAS |

[20]  G. Sheldrick, Acta Crystallogr. Sect. A 2015, 71, 3.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  G. Sheldrick, Acta Crystallogr. Sect. C 2015, 71, 3.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst. 2009, 42, 339.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjsFSnsbg%3D&md5=152b232aadeaa73225d2029119611dc4CAS |