Extremely short H···H distances and intermolecular hydrogen-bonding patterns of dialkyl α-aryl-α-(diphenylmethylamino)methanephosphonates

References

• Khukhar, V. P.; Hudson, H. R. eds. Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity; Wiley: Chichester, 2000.
   Google Scholar
• Hägele, G. Physical properties and NMR-spectroscopic characterization of aminophosphonates and aminophosphinates. In: V. P. Khukhar; H. R. Hudson (Eds.), Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity; Wiley: Chichester, 2000; pp. 217–284.
   Google Scholar
• Hudson H. R.; Lee, R. J. Phosphorus Sulfur Silicon Relat. Elem. 2014, 189, 1149–1155.
   Web of Science ®Google Scholar
• Hudson, H. R.; Lee, R. J.; Matthews, R. W. Phosphorus Sulfur Silicon. 2004, 179, 1691–1709.
   Web of Science ®Google Scholar
• Green, D. StC.; Gruss, U.; Hägele, G.; Hudson, H. R.; Lindblom, L.; Pianka, M. Phosphorus Sulfur Silicon Relat. Elem. 1996, 113, 179–207.
   Web of Science ®Google Scholar
• Issleib, K.; Döpfer, K. P.; Balszuweit, A. Z. Naturforsch. 1981, 36B, 1392–1394.
   Google Scholar
• Issleib, K.; Döpfer, K. P.; Balszuweit, A. Phosphorus Sulfur Silicon. 1983, 14, 171.
   Web of Science ®Google Scholar
• Keglevich, G.; Balint, E. Molecules. 2012, 17, 12821–12835.
   PubMed Web of Science ®Google Scholar
• (a)Allen, F. H. Acta Cryst. 2002, B58, 380–388.
   Google Scholar
  (b)Bruno, I. J.; Cole, J. C.; Kessler, M.; Luo, J.; Motherwell, W. D. S.; Purkis, L. H.; Smith, B. R.; Taylor, R.; Cooper, R. I.; Harris, S. E.; Orpen, A. G. J. Chem. Inf. Comput. Sci. 2004, 44, 2133–2144.
   PubMedGoogle Scholar
• Flack, H. D.; Bernardinelli, G. J. Appl. Cryst. 2000, 33, 1143–1148.
   Web of Science ®Google Scholar
• Hooft, R. W. W.; Straver, L. H.; Spek, A. L. J. Appl. Cryst. 2008, 41, 96–103.
   PubMed Web of Science ®Google Scholar
• Spek, A. L. Acta Cryst. 2009, D65, 148–155.
   Google Scholar
• Hooft, R. W. W.; Straver, L. H.; Spek, A. L. J. Appl. Cryst. 2010, 43, 665–668.
   Web of Science ®Google Scholar
• Schomaker, V.; Trueblood, K. N. Acta Cryst. 1968, B24, 63–76.
   Google Scholar
• The usage of “strict criteria” refers to search filters set in the CSD as rejecting hits that are disordered, have R values > 7.5%, are flagged as with error of some kind, stem from powder structures, or are of metal-organic nature. Conversely, “less stringent” only permits disordered structures to be included as hits; all other filters are kept.
   Google Scholar
• Kraicheva, I.; Vodenicharova, E.; Shivachev, B.; Nikolova, R.; Kril, A.; Topashka-Ancheva, M.; Iliev, I.; Georgieva, A.; Gerasimova, Ts.; Tosheva, T.; Tashev, E.; Tsacheva, I.; Troev, K. Phosphorus Sulfur Silicon Relat. Elem. 2013, 188, 1535–1547.
   Web of Science ®Google Scholar
• Swamy, K. C. K.; Kumaraswamy, S.; Kumar, K. S.; Muthiah, C. Tetrahedron Lett. 2005, 46, 3347–3351.
   Web of Science ®Google Scholar
• Hirayama, N.; Kasai, M.; Shirahata, K. Int. J. Pept. Protein Res. 1991, 38, 20–24.
   PubMedGoogle Scholar
• Additional hits permitting disordered structures are TOLHUZ, AWUZOI, AXANAP, and YIJHIK.16
   Google Scholar
• Ye, M.-Y.; Yao, G.-Y.; Pan, Y.-M.; Liao, Z.-X.; Zhang, Y.; Wang, H.-S., Eur. J. Med. Chem. 2014, 83, 116–128.
   PubMed Web of Science ®Google Scholar
• Kraicheva, I.; Tsacheva, I.; Vodenicharova, E.; Tashev, E.; Troev, K. Acta Crystallogr. Sect.E: Struct. Rep. Online. 2011, 67, o1980.
   Google Scholar
• Kraicheva, I.; Tsacheva, I.; Vodenicharova, E.; Tashev, E.; Troev, K. Acta Crystallogr. Sect.E: Struct. Rep. Online. 2011, 67, o2045.
   Google Scholar
• Hudson, H. R.; Czugler, M. manuscript in preparation.
   Google Scholar
• Crenshaw, M. D.; Schmolka, S. J.; Zimmer, H.; Whittle, R.; Elder, R. C. J. Org. Chem. 1982, 47, 101–104.
   Web of Science ®Google Scholar
• Kaboudin, B.; Saadati, F.; Yokomatsu, T. Synlett. 2010, 1837–1840.
   Google Scholar
• (a) Stewart, J. J. P. MOPAC2012, Stewart Computational Chemistry, Version 15.089L, http://OpenMOPAC.net (accessed July 2015);
   Google Scholar
  (b)Maia, J. D. C.; Carvalho, G. A. U.; Mangueira, C. P.; Santana, S. R.; Cabral, L. A. F.; Rocha, G. B. J. Chem. Theory Comput. 2012, 8, 3072–3081.
   PubMed Web of Science ®Google Scholar
• Stevens, R. C.; Bau, R.; Milstein, D.; Blum, O.; Koetzle, T. F. J. Chem. Soc. Dalton Trans. 1990, 1429–1432.
   Google Scholar
• Richardson, T. B.; de Gala, S.; Crabtree, R. H.; Siegbahn, P. E. M. J. Am. Chem. Soc. 1995, 117, 12875–12876.
   Web of Science ®Google Scholar
• Popelier, P. L. A.; J. Phys. Chem. A, 1998, 102, 1873–1878, and references therein.
   Web of Science ®Google Scholar
• Owczarek, M.; Majerz, I.; Jakubas, R. Cryst. Eng. Comm. 2014, 16, 7638–7648.
   Web of Science ®Google Scholar
• Klooster, W. T.; Koetzle, T. F.; Siegbahn, P. E. M.; Richardson, T. B.; Crabtree, R. H. J. Am. Chem. Soc. 1999, 121, 6337–6343.
   Web of Science ®Google Scholar
• Singh, P. C.; Patwari, G. N. Chem. Phys. Lett. 2006, 419, 265–268.
   Web of Science ®Google Scholar
• Lipkowski, P.; Grabowski, S. J.; Robinson, T. L.; Leszczynski, J. J. Phys. Chem. A. 2004, 108, 10865–10872.
   Web of Science ®Google Scholar
• Similar RS-dimeric structures have been reported for the α-(3,4-methylenedioxy)phenyl and α-(2-pyrrolyl) derivatives (Woodroffe, T. M.Ph.D. Thesis, University of North London, 1997.
   Google Scholar
• Hudson, H. R.; McPartlin, M.; Matthews, R. W.; Powell, H.; Yusuf, R. O.; Jászay, Z. M.; Keglevich, Gy.; Petneházy, I.; Tőke, L. Phosphorus Sulfur Silicon. 1993, 79, 239–243.
   Web of Science ®Google Scholar
• Bashall, A. P.; Crowder, J.; Dronia, H.; Hägele, G.; Hudson, H. R.; Lee, R. J.; McPartlin, M.; Matthews, R. W.; Ollig, J. Heteroatom Chem. 2010, 21, 314–325.
   Web of Science ®Google Scholar
• Choi, N.; McPartlin, M. X-ray crystallographic studies. In: V. P. Khukhar; H. R. Hudson (Eds.), Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity; Wiley: Chichester, 2000, pp. 327–361.
   Google Scholar
• Bogomilova, A.; Hägele, G.; Troev, K.; Wagner, E.; Guenther, M. Phosphorus Sulfur Silicon Relat. Elem. 2012, 187, 165–180.
   Web of Science ®Google Scholar
• Taylor, R.; Kennard, O. J. Amer. Chem. Soc. 1982, 104, 5063–5070.
   Web of Science ®Google Scholar
• Taylor, R.; Kennard, O. Acta Crystallogr. 1984, Sec. A, C115, Suppl. S.
   Google Scholar
• (a)Patterson, A. L.; Groshens, B. P. Nature, 1954, 173, 398.
   Web of Science ®Google Scholar
  (b) Czugler, M.; Kálmán, A.; Kovács, J.; Pintér, I. Acta Crystallogr. Sect. B. 1981, 37, 172–177.
   Web of Science ®Google Scholar
  (c)Bombicz, P.; Czugler, M.; Tellgren, R.; Kálmán, A. Angew. Chem. Int. Ed. 2003, 42, 1957–1960.
   PubMed Web of Science ®Google Scholar
• (a) Klein, R. A. Chem. Phys. Lett. 2006, 425, 128–133.
   Web of Science ®Google Scholar
  (b) Batsanov, S. S. Struct. Chem., 1999, 10, 395–400.
   Web of Science ®Google Scholar
  (c) Batsanov, S. S. Inorg. Mat. 2001, 37, 871–885.
   Web of Science ®Google Scholar
• (a) Sheldrick, G. M. SHELXTL PC, Version 4.2; Siemens Analytical X-Ray Instruments: Madison, WI, 1990.
   Google Scholar
  (b) Sheldrick, G. M. Acta Cryst. 2008, A64, 112–122.
   Google Scholar
  (c) Sheldrick, G. M. Acta Cryst. 2015, C71, 3–8.
   Google Scholar
• Stewart, J. J. P. J. Mol. Mod. 2007, 13, 1173–1213.
   PubMed Web of Science ®Google Scholar
• Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104.
   PubMed Web of Science ®Google Scholar