Five New Pseudopolymorphs of sym-Trinitrobenzene

Crystal Growth and Design

Volumn 3, Issue 6, 2003, Pages 1033-1040

  Jetti, Ram K R ^a   Boese, Roland ^a   Thallapally, Praveen K ^b   Desiraju, Gautam R ^b  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 TRIMETHYLBENZENE; BENZYL THIOCYANATE; META XYLENE; NITROBENZENE DERIVATIVE; TOLUENE;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; MOLECULAR INTERACTION;

EID: 0345014863     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg034141z     Document Type: Article

References (40)

1. Kumar, V. S. S.; Kuduva, S. S.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2, 1999, 1069-1074.
2. Byrn, S. R. Solid-State Chemistry of Drugs; Academic: New York, 1982.
3. Bernstein, J. Polymorphism in Molecular Crystals; Clarendon: Oxford, 2002.
4. (a) Threlfall, T. L. Analyst 1995, 120, 2435-2460.
5. (b) Bingham, A. L.; Hughes, D. S.; Hursthouse, M. B.; Lancaster, R. W.; Tavener, S.; Threlfall, T. L. Chem. Commun. 2001, 603-604.
6. (c) Sarma, J. A. R. P.; Desiraju, G. R. Polymorphism and Pseudopolymorphism in Organic Crystals: A Cambridge Structural Database Study; In Crystal Engineering; Seddon, K. R., Zaworotko, M., Eds.; Kluwer: Norwell, MA, 1999; pp 325-356.
7. (d0 Desiraju, G. R. Science 1996, 278, 404-405. Very recent papers include
8. (e) Davey, R. J. Chem. Commun. 2003, 1463-1467.
9. (f) Jetti, R. K. R.; Boese, R.; Sarma, J. A. R. P.; Reddy, L. S. R.; Vishweshwar, P.; Desiraju, G. R. Angew. Chem., Int. Ed. 2003, 42, 1963-1967.
10. (g) Yu, L. J. Am. Chem. Soc. 2003, 125, 6380-6381.
11. (h) Kálmán, A.; Fábián, L.; Argay, G.; Bernáth, G.; Gyarmati, Z. J. Am. Chem. Soc. 2003, 125, 34-35.
12. Nangia, A.; Desiraju, G. R. Chem. Commun. 1999, 605-606.
13. Anthony, A.; Desiraju, G. R. Supramol. Chem. 2001, 73, 11-23.
14. (a) Foster, R. Organic Charge-Transfer Complexes; Academic: New York. 1969.
15. (b) Pfeiffer, P. Organische Molekülverbindungen, 2nd ed.; Ferdinand Enke: Stuttgart, 1927.
16. (c) Becker, C. Chem. Ber. 1883, 16, 1597.
17. 1/c) that is more stable than the two orthorhombic forms above and also structurally quite unrelated to them.
18. SHELXTL, Versions 6.10 and 6.12, 2000 Bruker AXS Inc., Madison, Wisconsin, USA.
19. Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565-573.
20. Thallapally, P. K.; Katz, A. K.; Carrell, H. L.; Desiraju, G. R. Cryst. Eng. Comm. 2003, 5, 87-92 and references therein.
21. Zyss, J.; Ledoux, I.; Weiss, H.-C.; Boese, R.; Thallapally, P. K.; Thalladi, V. R.; Desiraju, G. R. Chem. Mater. 2003, 15, 3063-3073.
22. Thallapally, P. K.; Chakraborty, K.; Carrell, H. L.; Kotha, S.; Desiraju, G. R. Tetrahedron 2000, 56, 6721-6728.
23. (a) Aryl⋯aryl perpendicular distances and aryl⋯aryl centroid distances for solvates 1-5 were calculated using the PLATON Program: Platon-version 1.05, 2002: Spek, A. L. Acta Crystallogr. 1990, A46, C34.
24. (b) Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 21, 3885-3896. The π⋯π interactions seen here are similar to those found in molecular complexes of picric acid, picryl chloride, and TCNQ. We looked for related structures in the CSD. Interestingly, the benzene solvate of picric acid has a crystal packing similar to that of solvate 1, whereas the o-xylene solvate of picric acid is isostructural to solvate 4. See
25. (c) Takayanagi, H.; Toubai, Y.; Goto, M.; Yamaguchi, S.; Ogura, H. Chem. Pharm. Bull. 1991, 39, 2491-93.
26. (d) Goto, M.; Osa, Y.; Takeda, K.; Yamaguchi, S.; Takayanagi, H. Chem. Pharm. Bull. 1998, 46, 1621-1625.
27. (a) Barbour, L. J. J. Supramol. Chem. 2001, 1, 189-191.
28. (b) Atwood, J. L.; Barbour, L. J. Cryst. Growth Des. 2003, 3, 3-8.
29. (a) Kálmán, A.; Párkányi, L. Adv. Mol. Struct. Res. 1997, 3, 189.
30. (b) Muthuraman, M.; Fur, Y. L.; Beucher, M. B.; Masse, R.; Nicoud, J.-F. ; George, S.; Nangia, A.; Desiraju, G. R. J. Solid State Chem. 2000, 152, 221-228.
31. Desiraju, G. R.; Sarma, J. A. R. P. Proc. Ind. Acad. Sci., (Chem. Sci.) 1986, 96, 599-605.
32. (a) Moorthy, J. N.; Natarajan, R.; Mal, P.; Venugopalan, P. J. Am. Chem. Soc. 2002, 124, 6530-6531.
33. (b) Thalladi, V. R.; Boese, R.; Brasselet, S.; Ledoux, I.; Zyss, J.; Jetti, R. K. R.; Desiraju, G. R. Chem. Commun. 1999, 1639-1640.
34. (c) Das, D.; Jetti, R. K. R.; Boese, R.; Desiraju, G. R. Cryst. Growth Des. 2003, 3, 675-681.
35. (a) Brammer, L.; Bruton, E. A.; Sherwood, P. Cryst. Growth Des. 2001, 1, 277-290.
36. (b) Thallapally, P. K.; Nangia, A. CrystEngComm 2001, 27.
37. (c) Aakeröy, C. B.; Evans, T. A.; Seddon, K. R.; Pálinkó, I. New. J. Chem. 1999, 145-152.
38. Allen, F. H.; Kennard, O. Chem. Des. Autom. News 1993, 8, 1-57.
39. Herbstein, F. H.; Kapon, M.; Reisner, G. M. Acta Crystallogr. 1986, B42, 181-187.
40. Desiraju, G. R., manuscript in preparation.