A comparison of X-ray crystal structures including methyl 3,5-bis(hydroxymethyl)benzoate, its phenylethynyl extended derivative in polymorphous forms and the corresponding carboxylic acids

Structural Chemistry

Volumn 23, Issue 1, 2012, Pages 245-255

  Katzsch, Felix ^a   Eißmann, Diana ^a   Weber, Edwin ^a  

^a TU BERGAKADEMIE FREIBERG   (Germany)

Author keywords

Crystal engineering; Dihydroxycarboxylic acids and esters; Hydrogen bonds; Polymorphism; Single crystal X ray analysis

Indexed keywords

EID: 84862698369     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11224-011-9858-0     Document Type: Article

References (45)

1. Steed JW, Atwood JL (2009) Supramolecular chemistry, 2nd edn. Wiley, Chichester
2. Vittal J, Zaworotko M, Tiekink ERT (eds) (2010) Organic crystal engineering. Wiley, New York
3. Aakeröy CB, Champness NR, Janiak C (2010) Cryst Eng Comm 12:22
4. Hobza P, Müller-Dethlefs K (2010) Non-covalent interactions. Royal Society of Chemistry, Cambridge
5. Jeffrey GA (1997) An introduction to hydrogen bonding. Oxford University Press, Oxford
6. Desiraju GR (2004) In: Atwood JL, Steed JW (eds) Encyclopedia of supramolecular chemistry. Marcel Dekker, New York, pp 658-665
7. Steiner T (2002) Angew Chem Int Ed 41:48
8. Braga D, Grepioni F (2004) In: Atwood JL, Steed JW (eds) Encyclopedia of supramolecular chemistry. Marcel Dekker, New York, pp 357-363
9. Desiraju GR (2002) Acc Chem Res 35:565
10. Burrows AD (2004) In: Mingos DMP (ed) Supramolecular assembly via hydrogen bonds I, structure and bonding, vol 108. Springer, Berlin, Heidelberg, pp 55-96
11. Desiraju GR, Steiner T (1999) The weak hydrogen bond. Oxford University Press, Oxford
12. Nishio M (2004) In: Atwood JL, Steed JW (eds) Encyclopedia of supramolecular chemistry. Marcel Dekker, New York, pp 1576-1583
13. Steiner T (1997) Chem Commun 727
14. Kuan FS, Ho SY, Tadbuppa PP, Tiekiuk ERT (2008) Cryst-EngComm 10:548
15. Felsmann M, Eißmann F, Schwarzer A, Weber E (2011) Cryst Growth Des 11:982
16. Schollmeyer D, Shishkin OV, Rühl T, Vysotsky MO (2008) Cryst Eng Comm 10:715
17. Kurjatschij S, Eißmann D, Seichter W, Weber E (2011) Z Kristallogr 226:291
18. Nishio M, Umezawa Y, Honda K, Tsuboyama S, Suezawa H (2009) Cryst Eng Comm 11:1757
19. Nishio M (2004) Cryst Eng Comm 6:130
20. Fischer C, Lin G, Bombicz P, Seichter W, Weber E (2011) Struct Chem 22:433
21. Prasanna MD, Guru Row TN (2000) Cryst Eng 3:135
22. Thallapally PK, Nangia A (2001) Cryst Eng Comm 3:114
23. Brammer L, Bruton EA, Sherwood P (2001) Cryst Growth Des 1:277
24. Schwarzer A, Seichter W, Weber E (2011) Struct Chem 22:95
25. Desiraju GR (1995) Angew Chem Int Ed 34:2311
26. Nangia A, Desiraju GR (1998) In: Weber E (ed) Design of organic solids, topics in current chemistry, vol 198. Springer, Berlin, Heidelberg, pp 57-95
27. Bernstein J, Novoa JJ, Boese R, Cirkel SA (2010) Chem Eur J 16:9047
28. Brock CP, Duncan LL (1994) Chem Mater 6:1307
29. Weber E, Czugler M (1988) In: Weber E (ed) Molecular inclusion and molecular recognition-clathrates II, topics in current chemistry, vol 149. Springer, Berlin, Heidelberg, pp 45-134
30. Kohmoto S, Kuroda Y, Someya Y, Kishikawa K, Masu H (2009) Cryst Growth Des 9:3457
31. Sonogashira K (2002) J Organomet Chem 653:46
32. Hung MC, Liao JL, Chen SA, Chen SH, Su AC (2005) J Am Chem Soc 127:14576
33. Melissaris AP, Litt MH (1992) J Org Chem 57:6998
34. Havens SJ, Hergenrother PM (1985) J Org Chem 50:1763
35. Mazik M, König A (2007) Eur J Org Chem 3271
36. Liu Y, Lahti PM (2004) Molecules 725
37. Dimick SM, Powell SC, McMahon SA, Moothoo DN (1999) J Am Chem Soc 121:10286
38. Seebach D, Herrmann GF, Lengweiler UD, Amrein W (1997) Helv Chim Acta 80:989
39. Sivakumar C, Nasar AS (2009) J Polym Sci A 47:3337
40. Bruker AXS Inc (2007) Madison, WI
41. Sheldrick GM (2008) Acta Crystallogr A64:112
42. Spek AL (2009) Acta Crystallogr D65:148
43. Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Angew Chem Int Ed 34:1555
44. Janiak C (2000) J Chem Soc Dalton Trans 3885
45. Bernstein J (2002) Polymorphism in molecular crystals, IUCr monographs on crystallography, vol 14. Oxford University Press, Oxford