Abstract
Two coordination complexes [Ni(Hpydco)2(bpy)] (1) and [Ni(pydco)(phen)(H2O)2]·4.5H2O 0.5CH3OH (2) have been synthesized using a mixed-ligand system including pyridine-2,5-dicarboxylic acid N-oxide (H2pydco) as an O-donor ligand and 2,2'-bipyridine (bpy) or 1,10-phenanthroline (phen) as a chelating N-donor ligand and NiCl2.6H2O as a source for Ni ions. The crystal structures of 1 and 2 form discrete complexes in which extensive π−π stacking interactions between aromatic rings of the N-donor ligands resulted in the formation of one dimensional (1D) chain-like structures. The chains are connected by hydrogen bonds to expand the structures into 2D-supramolecular networks. Hirshfeld surface analysis and Density Functional Theory (DFT) calculations were included to rationalize the relative strength of the π-stacking assemblies observed in both complexes.
References
G.R. Desiraju, Crystal engineering from molecules. to materials. J mol. Struct. 656(1–3), 5–15 (2003)
T.S. Thakur, R. Dubey, G.R. Desiraju, Crystal Structure and Prediction. Annu. Rev. Phys. Chem. 66, 21–42 (2015). https://doi.org/10.1146/annurev-physchem-040214-121452
D. Braga, F. Grepioni, L. Maini, S. D’Agostino, From solid-state structure and dynamics to crystal engineering. Eur. J. Inorg. Chem. 2018, 3597–3605 (2018). https://doi.org/10.1002/ejic.201800234
H. Schneider, Noncovalent interactions: a brief account of a long history. J. Phys. Org. Chem. 35, e4340 (2022). https://doi.org/10.1002/poc.4340
M.C. Storer, C.A. Hunter, The surface site interaction point approach to non-covalent interactions. Chem. Soc. Rev. 51, 10064–10082 (2022). https://doi.org/10.1039/D2CS00701K
Y. Wang, J. Lv, P. Gao, Y. Ma, Crystal structure prediction via efficient sampling of the potential energy surface. Acc. Chem. Res. 55, 2068–2076 (2022). https://doi.org/10.1021/acs.accounts.2c00243
Q. Zhu, S. Hattori, Organic crystal structure prediction and its application to materials design. J. Mater. Res. 38, 19–36 (2023). https://doi.org/10.1557/s43578-022-00698-9
X. Yin, C.E. Gounaris, Search methods for inorganic materials crystal structure prediction. Curr. Opin. Chem. Eng. 35, 100726 (2022). https://doi.org/10.1016/j.coche.2021.100726
I. Alkorta, J. Elguero, A. Frontera, Not only hydrogen bonds: other noncovalent interactions. Crystals 10, 180 (2020). https://doi.org/10.3390/cryst10030180
S. Roca, L. Hok, R. Vianello, M. Borovina, M. Đaković, L. Karanović, D. Vikić-Topić, Z. Popović, The role of non-covalent intermolecular interactions on the diversity of crystal packing in supramolecular dihalopyridine–silver(I) nitrate complexes. CrystEngComm 22, 7962–7974 (2020). https://doi.org/10.1039/D0CE01257B
K.T. Mahmudov, A.V. Gurbanov, F.I. Guseinov, M.F.C. Guedes da Silva, Noncovalent interactions in metal complex catalysis. Coord. Chem. Rev. 387, 32–46 (2019). https://doi.org/10.1016/j.ccr.2019.02.011
M. Bazargan, M. Mirzaei, A. Franconetti, A. Frontera, On the preferences of five-membered chelate rings in coordination chemistry: insights from the cambridge structural database and theoretical calculations. Dalton Trans. 48, 5476–5490 (2019). https://doi.org/10.1039/C9DT00542K
A. Bencini, V. Lippolis, 1,10-Phenanthroline: a versatile building block for the construction of ligands for various purposes. Coord. Chem. Rev. 254, 2096–2180 (2010). https://doi.org/10.1016/j.ccr.2010.04.008
C. Kaes, A. Katz, M.W. Hosseini, Bipyridine: the most widely used ligand. a review of molecules comprising at least two 2, 2’-bipyridine units. Chem. Rev. 100, 3553–3590 (2000). https://doi.org/10.1021/cr990376z
H. Constable, The early years of 2,2’-Bipyridine—a ligand in its own lifetime. Molecules 24, 3951 (2019). https://doi.org/10.3390/molecules24213951
P.G. Sammes, G. Yahioglu, 1,10-Phenanthroline: a versatile ligand. Chem. Soc. Rev. 23, 327 (1994). https://doi.org/10.1039/cs9942300327
H.S. Moradi, E. Momenzadeh, M. Asar, S. Iranpour, A.R. Bahrami, M. Bazargan, H. Hassanzadeh, M.M. Matin, M. Mirzaei, Bioactivity studies of two copper complexes based on pyridinedicarboxylic acid N-oxide and 2,2′-bipyridine. J. Mol. Struct. 1249, 131584 (2022). https://doi.org/10.1016/j.molstruc.2021.131584
H. Alizadeh, M. Mirzaei, A.S. Saljooghi, V. Jodaian, M. Bazargan, J.T. Mague, R.M. Gomila, A. Frontera, Coordination complexes of zinc and manganese based on pyridine-2,5-dicarboxylic acid N -oxide: DFT studies and antiproliferative activities consideration. RSC Adv. 11, 37403–37412 (2021). https://doi.org/10.1039/D1RA08258B
C.R. Groom, I.J. Bruno, M.P. Lightfoot, S.C. Ward, The cambridge structural database. Acta Cryst. B 72, 171–179 (2016). https://doi.org/10.1107/S2052520616003954
M. Bazargan, M. Mirzaei, A.S. Hamid, Z.H. Kafshdar, H. Ziaekhodadadian, E. Momenzadeh, J.T. Mague, D.M. Gil, R.M. Gomila, A. Frontera, On the importance of π-stacking interactions in the complexes of copper and zinc bearing pyridine-2,6-dicarboxylic acid N-oxide and N-donor auxiliary ligands. CrystEngComm 24, 6677–6687 (2022). https://doi.org/10.1039/D2CE00656A
M. Bazargan, M. Mirzaei, M. Aghamohamadi, M. Tahmasebi, A. Frontera, Supramolecular assembly of a 2D coordination polymer bearing pyridine-N-oxide-2,5-dicarboxylic acid and copper ion: X-ray crystallography and DFT calculations. J. Mol. Struct. 1202, 127243 (2020). https://doi.org/10.1016/j.molstruc.2019.127243
D Frisch, MJ. Trucks, GW. Schlegel, HB Scuseria, GE Robb, MA Cheeseman, JR Scalmani, G Barone, V Petersson, GA Nakatsuji, HLiX. Caricato, M Marenich, AV Bloino, J Janesko, BG Gomperts, R Mennucci, B Hratchian, HP Gaussian 16, Revision A.01; Gaussian, Inc.: Wallingford, CT, USA, 2016, (n.d.)
S. Grimme, J. Antony, S. Ehrlich, H. Krieg, A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J. Chem. Phys. 132, 154104 (2010). https://doi.org/10.1063/1.3382344
F. Weigend, Accurate coulomb-fitting basis sets for H to Rn. Phys. Chem. Chem. Phys. 8, 1057 (2006). https://doi.org/10.1039/b515623h
C. Adamo, V. Barone, Toward reliable density functional methods without adjustable parameters: the PBE0 model. J. Chem. Phys. 110, 6158–6170 (1999). https://doi.org/10.1063/1.478522
S.F. Boys, F. Bernardi, The calculation of small molecular interactions by the differences of separate total energies. some procedures with reduced errors. Mol. Phys. 19, 553–566 (1970). https://doi.org/10.1080/00268977000101561
R.F.W. Bader, A quantum theory of molecular structure and its applications. Chem. Rev. 91, 893–928 (1991). https://doi.org/10.1021/cr00005a013
T.A. Keith, TK Gristmill Software, AIMAll (overland park, USA, 2013)
J. Contreras-García, E.R. Johnson, S. Keinan, R. Chaudret, J.-P. Piquemal, D.N. Beratan, W. Yang, NCIPLOT: a program for plotting noncovalent interaction regions. J. Chem. Theory Comput. 7, 625–632 (2011). https://doi.org/10.1021/ct100641a
D. Sadhukhan, M. Maiti, G. Pilet, A. Bauzá, A. Frontera, S. Mitra, Hydrogen bond, π–π, and CH–π interactions governing the supramolecular assembly of some hydrazone ligands and their MN II complexes – structural and theoretical interpretation. Eur. J. Inorg. Chem. 2015, 1958–1972 (2015). https://doi.org/10.1002/ejic.201500030
G. Mahmoudi, A. Bauzá, M. Amini, E. Molins, J.T. Mague, A. Frontera, On the importance of tetrel bonding interactions in lead(II) complexes with (iso)nicotinohydrazide based ligands and several anions. Dalton Trans. 45, 10708–10716 (2016). https://doi.org/10.1039/C6DT01947A
W. APEX3, SADABS and SAINT, Bruker-AXS, Madison, (2016)
G. G. M. Sheldrick, TWINABS. University of Göttingen, Göttingen
G.M. Sheldrick, SHELXT—Integrated space-group and crystal-structure determination. Acta Cryst. A 71, 3–8 (2015). https://doi.org/10.1107/S2053273314026370
G.M. Sheldrick, Crystal structure refinement with SHELXL. Acta Cryst. C 71, 3–8 (2015). https://doi.org/10.1107/S2053229614024218
M.A. Spackman, D. Jayatilaka, Hirshfeld surface analysis. CrystEngComm 11, 19–32 (2009). https://doi.org/10.1039/B818330A
J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces. Chem. Commun 37, 3814 (2007). https://doi.org/10.1039/b704980c
J.J. McKinnon, M.A. Spackman, A.S. Mitchell, Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Cryst. B 60, 627–668 (2004). https://doi.org/10.1107/S0108768104020300
P.R. Spackman, M.J. Turner, J.J. McKinnon, S.K. Wolff, D.J. Grimwood, D. Jayatilaka, M.A. Spackman, CrystalExplorer : a program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. J. Appl. Crystallogr. 54, 1006–1011 (2021). https://doi.org/10.1107/S1600576721002910
M. Mirzaei, F. Sadeghi, K. Molčanov, J.K. Zarȩba, R.M. Gomila, A. Frontera, Recurrent supramolecular motifs in a series of acid-base adducts based on pyridine-2,5-dicarboxylic Acid N -oxide and organic bases: inter- and intramolecular hydrogen bonding. Cryst. Growth Des. 20, 1738–1751 (2020). https://doi.org/10.1021/acs.cgd.9b01475
Z. Hosseini-Hashemi, M. Mirzaei, A. Jafari, P. Hosseinpour, M. Yousefi, A. Frontera, M. Lari Dashtbayaz, M. Shamsipur, M. Ardalani, Effects of N -oxidation on the molecular and crystal structures and properties of isocinchomeronic acid, its metal complexes and their supramolecular architectures: experimental CSD survey, solution and theoretical approaches. RSC Adv. 9, 25382–25404 (2019). https://doi.org/10.1039/C9RA05143K
M. Bazargan, M. Mirzaei, H. Eshtiagh-Hosseini, J.T. Mague, A. Bauzá, A. Frontera, Synthesis, X-ray characterization and DFT study of a novel Fe(III)–pyridine-2,6-dicarboxylic acid N-oxide complex with unusual coordination mode. Inorg. Chim. Acta 449, 44–51 (2016). https://doi.org/10.1016/j.ica.2016.04.044
M. Mirzaei, H. Eshtiagh-Hosseini, M. Bazargan, F. Mehrzad, M. Shahbazi, J.T. Mague, A. Bauzá, A. Frontera, Two new copper and nickel complexes of pyridine-2,6-dicarboxylic acid N-oxide and their proton transferred salts: solid state and DFT insights. Inorg. Chim. Acta 438, 135–145 (2015). https://doi.org/10.1016/j.ica.2015.08.030
M. Shahbazi, F. Mehrzad, M. Mirzaei, H. Eshtiagh-Hosseini, J.T. Mague, M. Ardalani, M. Shamsipur, Synthesis, single crystal X-ray characterization, and solution studies of Zn(II)-, Cu(II)-, Ag(I)- and Ni(II)-pyridine-2,6-dipicolinate N-oxide complexes with different topologies and coordination modes. Inorg. Chim. Acta 458, 84–96 (2017). https://doi.org/10.1016/j.ica.2016.12.030
M. Mirzaei, H. Eshtiagh-Hosseini, M. Bazargan, Syntheses and X-ray crystal structure studies of four new coordination complexes and salts based on proton-transferred pyridine-2,6-dicarboxylic acid N-oxide. Res. Chem. Intermed. 41, 9785–9803 (2015). https://doi.org/10.1007/s11164-015-1965-x
M Ataei, V Jodaeian, M Mirzaei, ASh Saljooghi, A Gholizadeh, (2019) Syntheses characterization and antiproliferative study of some complexes containing pyridine-2,6-dicarboxylic acid N-oxide. Nashrieh Shimi va Mohandesi Shimi Iran.
K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, in Handbook of Vibrational Spectroscopy. ed. by P.R. Griffiths (Wiley, Chichester, 2006), pp.1872–1892. https://doi.org/10.1002/0470027320.s4104
M. Naeem Ahmed, K.A. Yasin, S. Aziz, S.U. Khan, M.N. Tahir, D.M. Gil, A. Frontera, Relevant π-hole tetrel bonding interactions in ethyl 2-triazolyl-2-oxoacetate derivatives: hirshfeld surface analysis and DFT calculations. CrystEngComm 22, 3567–3578 (2020). https://doi.org/10.1039/D0CE00335B
E. Espinosa, E. Molins, C. Lecomte, Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities. Chem. Phys. Lett. 285, 170–173 (1998). https://doi.org/10.1016/S0009-2614(98)00036-0
Acknowledgements
M.M. gratefully acknowledges financial support from the Ferdowsi University of Mashhad (Grant No. 3/50211), the Iran Science Elites Federation (ISEF), Zeolite and Porous Materials Committee of Iranian Chemical Society and the Iran National Science Foundation (INSF). This work is supported by Iran Science Elites Federation Grant No. M/98208, M/99397, and M/400230. J.T.M thanks Tulane University for support of the Tulane Crystallography Laboratory.
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Hamid, A.S., Mirzaei, M., Bazargan, M. et al. Synthesis and structural characterization of nickel(II) coordination complexes with mixed-ligand systems: exploring π−π stacking and hydrogen bonding in supramolecular assemblies. J IRAN CHEM SOC (2024). https://doi.org/10.1007/s13738-024-03034-6
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DOI: https://doi.org/10.1007/s13738-024-03034-6