Crystal architecture of the low melting nitrogen heterocycles tetrafluoropyrimidine and trifluorotriazine

References

[1] K. Merz, V. Vasylyeva, Development and boundaries in the field of supramolecular synthons. CrystEngComm2010, 12, 3989.10.1039/c0ce00237bSuche in Google Scholar

[2] G. R. Desiraju, Crystal engineering: A holistic view. Angew. Chem. Int. Ed. 2007, 46, 8342.Suche in Google Scholar

[3] P. Metrangolo, G. Resnati, Halogen bonding: Where we are and where we are going. Cryst. Growth Des. 2013, 12, 5835.Suche in Google Scholar

[4] S. L. Sunil, S. K. Nayak, V. R. Hathwar, D. Chopra, T. N. Guru Row, Pharmaceutical salts and co-crystals. Chapter: Role of fluorine in weak interactions in co-crystals. RSC Publishing, 2012, 29.10.1039/9781849733502-00029Suche in Google Scholar

[5] M. Karanam, A. R. Choudhury, Study of halogen-mediated weak interactions in a series of halogen-substituted Azobenzenes. Cryst. Growth Des. 2013, 13, 4803.Suche in Google Scholar

[6] S. K. Nayak, M. K. Reddy, T. N. Guru Row, D. Chopra, Role of Hetero-Halogen (F···X, X = Cl, Br, and I) or Homo-Halogen (X···X, X = F, Cl, Br, and I) interactions in substituted Benzanilides. Cryst. Growth Des. 2011, 11, 1578.Suche in Google Scholar

[7] J. D. Dunitz, R. Taylor, Organic fluorine hardly ever accepts hydrogen bonds. Chem. Eur. J.1997, 3, 89.Suche in Google Scholar

[8] J. A. K. Howard, V. J. Hoy, D. O’Hagan, D. T. Smith, How good is fluorine as a hydrogen bond acceptor? Tetrahedron1996, 52, 12613.10.1016/0040-4020(96)00749-1Suche in Google Scholar

[9] J. D. Dunitz, Organic fluorine: Odd man out. ChemBioChem2004, 5, 614.10.1002/cbic.200300801Suche in Google Scholar PubMed

[10] D. Chopra, Is organic fluorine really “not” polarizable?. Cryst. Growth Des. 2012, 12, 541.Suche in Google Scholar

[11] R. E. Banks, B. E. Smart, J. C. Tatlow, Organofluorine Chemistry. Principles and Commercial Application, Plenum Press, New York, 1994.10.1007/978-1-4899-1202-2Suche in Google Scholar

[12] V. Vasylyeva, K. Merz, Aggregation of fluorine-substituted pyridines. J. Fluor. Chem. 2010, 131, 446.Suche in Google Scholar

[13] V. R. Thalladi, H.-C. Weiss, D. Bläser, R. Boese, A. Nagnia, G. R. Desiraju, C-H^...F Interactions in the crystal structures of some fluorobenzenes. J. Am. Chem. Soc.1998, 120, 8702.Suche in Google Scholar

[14] K. Reichenbächer, H. I. Süss, J. Hulliger, Fluorine in crystal engineering –“the little atom that could”. Chem. Soc. Rev.2005, 34, 22.Suche in Google Scholar

[15] R. Berger, G. Resnati, P. Metrangolo, E. Weber, J. Hulliger, Organic fluorine compounds: a great opportunity for enhanced materials properties. Chem. Soc. Rev.2011, 40, 3496.Suche in Google Scholar

[16] G. Kaur, P. Panini, D. Chopra, A. R. Choudhury, Structural investigation of weak intermolecular interactions in fluorine substituted isomeric N-Benzylideneanilines. Cryst. Growth Des.2012, 12, 5096.Suche in Google Scholar

[17] A. G. Dikundwar, T. N. Guru Row, Evidence for the “Amphoteric” nature of fluorine in halogen bonds: an instance of Cl···F contact. Cryst. Growth Des. 2012, 12, 1713.Suche in Google Scholar

[18] S. Tothadi, S. Joseph, G. R. Desiraju, Synthon modularity in cocrystals of 4-Bromobenzamide with n-Alkanedicarboxylic acids: Type I and Type II Halogen···Halogen interactions. Cryst. Growth Des. 2013, 13, 3242.Suche in Google Scholar

[19] V. Vasylyeva, O. V. Shishkin, V. A. Maleev, K. Merz, Crystal structures of fluorinated pyridines from geometrical and energetic perspectives. Cryst. Growth Des. 2012, 12, 1032.Suche in Google Scholar

[20] D. Chopra, T. N. Guru Row, Role of organic fluorine in crystal engineering. CrystEngComm2011, 13, 2175.10.1039/c0ce00538jSuche in Google Scholar

[21] G. R. Desiraju, Chemistry beyond the molecule. Nature2001, 412, 397.10.1038/35086640Suche in Google Scholar PubMed

[22] K. E. Maly, Acenes vs N-Heteroacenes: The effect of N-substitution on the structural features of crystals of polycyclic aromatic hydrocarbons. Cryst. Growth Des.2011, 11, 5628.Suche in Google Scholar

[23] X. Mei, C. Wolf, Formation of new polymorphs of acridine using dicarboxylic acids as crystallisation templates in solution. Cryst. Growth Des.2004, 4, 1099.Suche in Google Scholar

[24] A. Kupka, V. Vasylyeva, D. W. M. Hofmann, K. V. Yusenko, K. Merz, Solvent and isotopic effects on acridine and deuterated acridine polymorphism. Cryst. Growth Des.2012, 12, 5966.Suche in Google Scholar

[25] N. Boden, P. P. Davis, C. H. Stam, G. A. Wesselink, Solid hexafluorobenzene. I. Crystal structure at 120.deg.K. Mol. Phys. 1973, 25, 81.Suche in Google Scholar

[26] H. Shorafa, D. Mollenhauer, B. Paulus, K. Seppelt, The two structures of the hexafluorobenzene radical cation C6F6. Angew. Chem., Int. Ed. 2009, 48, 5845.Suche in Google Scholar

[27] A. Olejniczak, A. Katrusiak, A. Vij, Interpenetrated structure and compressibility studies in pressure frozen pentafluoropyridine crystals at 0.3 and 1.1 GPa. J. Fluor. Chem.2008, 129, 173.Suche in Google Scholar

[28] M. T. Kirchner, D. Bläser, R. Boese, T. S. Thakur, G. R. Desiraju, Weak C—H^...O hydrogen bonds in anisaldehyde, salicylaldehyde and cinnamaldehyde. Acta Crystallogr. 2011, C67, o387.Suche in Google Scholar

[29] S. K. Nayak, G. Terraneo, A. Forni, P. Metrangolo, G. Resnati, C–Br···O supramolecular synthon: in situ cryocrystallography of low melting halogen-bonded complexes. CrystEngComm2012, 14, 4259.10.1039/c2ce25403dSuche in Google Scholar

[30] V. Vasylyeva, K. Merz, Fluorobenzonitriles: influence of the substitution pattern on melting and crystallization properties. Cryst. Growth Des.2010, 10, 4250.Suche in Google Scholar

[31] D. Chopra, T. N. Guru Row, In situ cryo crystallography: pathways to study intermolecular interactions. J. Ind. Inst. Sci. 2007, 87, 167.Suche in Google Scholar

[32] A. R. Choudhury, N. Winterton, A. Steiner, A. I. Cooper, K. A. Johnson, In situ crystallization of low-melting ionic liquids. J. Am. Chem. Soc. 2005, 127, 16792.Suche in Google Scholar

[33] D. S. Yufit, J. A. K. Howard, Low-melting molecular complexes of chloroform. CrystEngComm2010, 12, 737.10.1039/B914851ESuche in Google Scholar

[34] R. Boese, M. Nussbaumer, Correlation, Transformations and Interactions in Organic Crystal Chemistry, International Union of Crystallography Oxford University Press, Oxford, 1974.Suche in Google Scholar

[35] G. R. Desiraju, On the presence of multiple molecules in the crystal asymmetric unit (Z′>1). CrystEngComm2007, 9, 91.10.1039/B614933BSuche in Google Scholar

[36] D. Mootz, H. G. Wussow, Crystal structures of pyridine and pyridine trihydrate. J. Chem. Phys.1981, 75, 1517.Suche in Google Scholar