Abstract
The molecular structures of chloride salts of 2- and 5-substituted derivatives of 8-hydroxyquinoline, Me–H2Q+·Cl– ([C10H10NO]Cl) and Cl–H2Q+·Cl– ([C9H7ClNO]+·Cl–), were determined by single crystal X-ray diffraction methods; the latter is a new polymorph. In the crystal structures of these salts, several intra- and inter-molecular interactions result in a step-shaped centrosymmetric
Acknowledgments
The authors thank the Vice-President’s Office for Research Affairs of Isfahan University of Technology (IUT) and Shahid Beheshti University for supporting this work.
References
[1] T. Banerjee, A. K. Basak, S. K. Mazumdar, S. Chaudhuri, Structure of 8-hydroxy-5-quinolinesulphonic acid dihydrate, C9H7NO4S.2H2O. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 1984, 40, 507.Search in Google Scholar
[2] J. M. S. Skakle, J. L. Wardell, S. M. S. V. Wardell, Formation of ladders from
[3] L. Infantes, J. Chisholm, S. Motherwell, Extended motifs from water and chemical functional groups in organic molecular crystals. CrystEngComm 2003, 5, 480.10.1039/b312846fSearch in Google Scholar
[4] G. Smith, U. D. Wermuth, J. M. White, Molecular recognition involving Kemp’s triacid: selectivity towards the 8-substituted quinoline system as seen in the cocrystalline adducts with 8-aminoquinoline and 8-hydroxyquinoline. Chem. Commun. 2000, 2349.10.1039/b004945jSearch in Google Scholar
[5] G. Smith, U. D. Wermuth, J. M. White, Hydrogen bonding in proton-transfer compounds of 5-sulfosalicylic acid with bicyclic heteroaromatic Lewis bases. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 2004, 60, o575.Search in Google Scholar
[6] M. Pudipeddi, A. T. M. Serajuddin, Trends in solubility of polymorphs. J. Pharm. Sci. 2005, 94, 929.Search in Google Scholar
[7] Z. Ma, B. Moulton, A novel polymorph of 5-chloro-8-hydroxyquinoline with improved water solubility and faster dissolution rate. J. Chem. Crystallogr. 2009, 39, 913.Search in Google Scholar
[8] D. Singhal, W. Curatolo, Drug polymorphism and dosage form design: a practical perspective. Adv. Drug Deliv. Rev. 2004, 56, 335.Search in Google Scholar
[9] T. Wang, G. Zeng, X. Li, H. Zeng, In vitro studies on the antioxidant and protective effect of 2-substituted -8-hydroxyquinoline derivatives against H2O2-induced oxidative stress in BMSCs. Chem. Biol. Drug Des. 2010, 75, 214.Search in Google Scholar
[10] S. Zhai, L. Yang, Q. C. Cui, Y. Sun, Q. P. Dou, B. Yan, Tumor cellular proteasome inhibition and growth suppression by 8-hydroxyquinoline and clioquinol requires their capabilities to bind copper and transport copper into cells. J. Biol. Inorg. Chem. 2010, 15, 259.Search in Google Scholar
[11] M. M. Amini, G. Mohammadnezhad, H. R. Khavasi, Synthesis, crystal structure, and spectroscopic behavior of 8-hydroxyquinolato oxoalkoxo vanadium (V) complexes. J. Coord. Chem. 2012, 65, 2945.Search in Google Scholar
[12] G. Mohammadnezhad, A. R. Ghanbarpour, M. M. Amini, S. W. Ng, Bis(2-methylquinolin-8-olato-κ2N,O)lead(II). Acta Crystallogr. Sect. E, Struct Rep. 2010, 66, m529.Search in Google Scholar
[13] E. Sattarzadeh, G. Mohammadnezhad, M. M. Amini, S. W. Ng, 8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ2N,O)zincate(II) methanol solvate. Acta Crystallogr. Sect. E, Struct Rep. 2009, 65, m553.Search in Google Scholar
[14] E. Sattarzadeh, G. Mohammadnezhad, M. M. Amini, S. W. Ng, Bis(μ-2-methylquinolin-8-olato)-κ3N,O:O;κ3O:N,O-bis[(acetato-κO)(methanol-κO)zinc(II)]. Acta Crystallogr. Sect. E, Struct Rep. 2009, 65, m554.Search in Google Scholar
[15] R. Musiol, J. Jampilek, V. Buchta, L. Silva, H. Niedbala, B. Podeszwa, A. Palka, K. Majerz-Maniecka, B. Oleksyn, J. Polanski, Antifungal properties of new series of quinoline derivatives. Bioorg. Med. Chem. 2006, 14, 3592.Search in Google Scholar
[16] J. Novakova, E. Vlkova, B. Bonusova, V. Rada, L. Kokoska, In vitro selective inhibitory effect of 8-hydroxyquinoline against bifidobacteria and clostridia. Anaerobe 2013, 22, 134.10.1016/j.anaerobe.2013.05.008Search in Google Scholar PubMed
[17] K. H. Lam, R. Gambari, K. K. H. Lee, Y. X. Chen, S. H. L Kok, R. S. M. Wong, F. Y. Lau, C. H. Cheng, W. Y. Wong, Z. X. Bian, A. S. C. Chan, J. C. O. Tang, C. H. Chui, Preparation of 8-hydroxyquinoline derivatives as potential antibiotics against Staphylococcus aureus. Bioorg. Med. Chem. Lett. 2014, 24, 367.Search in Google Scholar
[18] K. Kaur, M. Jain, R. P. Reddy, R. Jain, Quinolinesandstructurallyrelatedheterocyclesasantimalarials. Eur. J. Med. Chem., 2010, 45, 3245.Search in Google Scholar
[19] M. Orhan Puskullu, B. Tekiner, S. Suzen, Recent studies of antioxidant quinoline derivatives. Mini Rev. Med. Chem. 2013, 13, 365.Search in Google Scholar
[20] A. Shi, T. A. Nguyen, S. K. Battina, S. Rana, D. J. Takemoto, P. K. Chiang, D. H. Hua, Synthesis and anti-breast cancer activities of substituted quinolines. Bioorg. Med. Chem. Lett. 2008, 18, 3364.Search in Google Scholar
[21] D. Wang, J. Huang, X. Wang, Y. Yu, H. Zhang, Y. Chen, J. Liu, Z. Sun, H. Zou, D. Sun, G. Zhou, G. Zhang, Y. Lu, Y. Zhong, The eradication of breast cancer cells and stem cells by 8-hydroxyquinoline-loaded hyaluronan modified mesoporous silica nanoparticle-supported lipid bilayers containing docetaxel. Biomaterials, 2013, 34, 7662.Search in Google Scholar
[22] L. R. Naik, N. N. Math, Photo physical properties of 8-hydroxy quinoline. Indian J. Pure Appl. Phys. 2005, 43, 743.Search in Google Scholar
[23] R. J. Curry, W. P Gillin, 1.5 μm electroluminescence from erbium (III) tris(8-hydroxyquinoline) (ErQ) based organic light emitting diodes. Appl. Phys. Lett. 1999, 75, 1380.Search in Google Scholar
[24] V. Krishnakumar, R. Nagalakshmi, P. Janaki, Growth and spectroscopic characterization of a new organic nonlinear optical crystal – 8-hydroxyquinoline, Spectrochim. Acta Part A: Mol.Biomol.Spectrosc. 2005, 61, 1097.Search in Google Scholar
[25] B. T. Jahromi, A. N. Kharat, S. Foroutannejad, synthesis, characterization and cytotoxic activity of 8-hydroxyquinoline derivatives. Res. J. Pharm., Biol. Chem. Sci. 2011, 2, 61.Search in Google Scholar
[26] SMART (Version 5.63) and SAINT (Version 6.45): Area Detector Control and Integration Software, Bruker AXS Inc., Madison, WI, USA, 2003.Search in Google Scholar
[27] G. M. Sheldrick, A short history of SHELX. Acta Crystallogr. Sect. A, 2008, 64, 112.10.1107/S0108767307043930Search in Google Scholar PubMed
[28] International Tables For X-ray Crystallography, Vol C, Kluwer Academic Publisher, Doordrecht, The Netherlands 1995.Search in Google Scholar
[29] DIAMOND: Brandenburg K., Crystal and Molecular Structure Visualization (Version 3.2f), Crystal Impact GbR, Bonn, Germany 2010.Search in Google Scholar
[30] J.-D. Chai, M. Head-Gordon, Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys. Chem. Chem. Phys. 2008, 10, 6615.Search in Google Scholar
[31] A. E. Reed, R. B. Weinstock, F. Weinhold, Natural population analysis. J. Chem. Phys. 1985, 83, 735.Search in Google Scholar
[32] A. E. Reed, L. A. Curtiss, F. Weinhold, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88, 899.Search in Google Scholar
[33] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, revision B.01. Gaussian, Inc., Wallingford CT, 2009.Search in Google Scholar
[34] G. B. Deacon, T. Dierkes, M. Hübner, P. C. Junk, Y. Lorenz, A. Urbatsch, Alkali metal/lanthanoid heterobimetallic complexes of 8-hydroxyquinolines accessed by pseudo-solid-state reactions. Eur. J. Inorg. Chem. 2011, 28, 4338.Search in Google Scholar
[35] P. Vranec, I. Potocnak, P. Repovsky, Low-dimensional compounds containing bioactive ligands. IV. Unusual ionic forms of 5-chloro-quinolin-8-ol. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 2012, 68, m370.Search in Google Scholar
[36] B. Moulton, M. J. Zaworotko, From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. Chem. Rev. 2001, 101, 1629.Search in Google Scholar
[37] D. Firley, B. Fraisse, F. Zouhiri, A. S. Bire, D. Desmaele, J. d’Angeloc, N. E. Ghermani, 7-Carboxylato-8-hydroxy-2-methylquinolinium monohydrate and 7-carboxy-8-hydroxy-2-methylquinolinium chloride monohydrate at 100 K. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 2005, 61, o154.Search in Google Scholar
[38] A. J. Middleton, W. J. Marshall, N. S. Radu, Elucidation of the structure of a highly efficient blue electroluminescent material. J. Am. Chem. Soc. 2003, 125, 880.Search in Google Scholar
[39] C. Yue, F. Jiang, Y. Xu, D. Yuan, L. Chen, C. Yan, M. Hong, The aggregations and strong emissions of d8 and d10 metal– 8-hydroxyquinaldine complexes. Cryst. Growth Des. 2008, 8, 2721.Search in Google Scholar
[40] G. Mohammadnezhad, M. M. Amini, V. Langer, Two polymorphs of a lead(II) complex with 8-hydroxy-2-methylquinoline and thiocyanate. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 2010, 66, m44.Search in Google Scholar
[41] M. Vafaee, G. Mohammadnezhad, M. M. Amini, S. W. Ng, 8-Hydroxy-2-methylquinolinium tetrachlorido(quinolin-8-olato-κ2N,O)stannate(IV) acetonitrile monosolvate. Acta Crystallogr. Sect. E, Struct Rep. 2010, 66, m381.Search in Google Scholar
[42] T. Banerjee, N. N. Saha, Hydrogen-bonding patterns in 8-hydroxyquinoline derivatives: (I) structure of 5-chloro-8-hydroxyquinoline and (II) refinement of the structure of 8-hydroxyquinoline. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 1986, 42, 1408.Search in Google Scholar
[43] G. Malecki, J. E. Nycz, E. Ryrych, L. Ponikiewski, M. Nowak, J. Kusz, J. Pikies, Synthesis, spectroscopy and computational studies of some biologically important hydroxyhaloquinolines and their novel derivatives. J. Mol. Struct. 2010, 969, 130.Search in Google Scholar
[44] X. Wang, D. Shi, S. Tu, C. Yao, Synthesis and crystal structures of 2-amino-3-cyano-4-(2-chlorophenyl)-1,4-dihydro-2H-pyrano[3, 2-h]quinoline and 2-amino-3-cyano-4-(2-chlorophenyl)-8-(2-chlorobenzylidene)-1,4,5,6,7,8-hexahydrobenzo[b]pyran. J. Chem. Cryst. 2004, 34, 159.Search in Google Scholar
[45] T. Tan, Supramolecular helical architecture from the self-assemblies of 2-chloro-5-nitro-benzoic acid and organic bases. J. Mol. Struct. 2007, 840, 6.Search in Google Scholar
[46] N. Barooah, R. J. Sarma, A. S. Batsanov, J. B. Baruah, Structural aspects of adducts of N-phthaloylglycine and its derivatives. J. Mol. Struct. 2006, 791, 122.Search in Google Scholar
[47] J. E. Nycz, G. Malecki, L. Ponikiewski, M. Leboschka, M. Nowak, J. Kusz, Synthesis, spectroscopy and computational studies of some novel phosphorylated derivatives of quinoline-5,8-diones. J. Mol. Struct. 2011, 986, 39.Search in Google Scholar
[48] G. Mohammadnezhad Sh., M. M. Amini, S. W. Ng, Bis(μ-5-chloro-quinolin-8-olato)-κ3 N,O:O;κ3 O:N,O-bis-[(acetato-κ2 O,O′)lead(II)]. Acta Crystallogr. Sect. E, Struct Rep. 2009, 65, m261.Search in Google Scholar
[49] M. Amati, S. Belviso, P. L. Cristinziano, C. Minichino, F. Lelj, 8-Hydroxyquinoline monomer, water adducts, and dimer. Environmental influences on structure, spectroscopic properties, and relative stability of cis and trans conformers. J. Phys. Chem. A 2007, 111, 13403.10.1021/jp074510sSearch in Google Scholar PubMed
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