Strychnine-8-ammonio-2-naphthalenesulfonate-water (1/1/3.5): The first structure of a strychnine or brucine compound with a zwitterionic species

Journal of Chemical Crystallography

Volumn 36, Issue 12, 2006, Pages 805-811

  Smith, Graham ^a   Wermuth, Urs D ^a   Healy, Peter C ^b   Young, David J ^b  

^a QUEENSLAND UNIVERSITY OF TECHNOLOGY   (Australia)

^b GRIFFITH UNIVERSITY   (Australia)

Author keywords

1,7 Cleve's acid; Hydrogen bonding; Molecular adduct; Naphthylaminesulfonic acids; Strychnine

Indexed keywords

STRYCHNOS TOXIFERA;

EID: 33845288650     PISSN: 10741542     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10870-006-9085-5     Document Type: Article

References (72)

1. Fischer, E. Ber. 1899, 32, 2451.
2. Holmes, H.L. In The Alkaloids, vol. II, Manske R.H.F.; Holmes, H.L., Eds.; Academic: New York, 1952; p. 514.
3. Briggs, L.H.; Openshaw, H.T.; Robinson, R.J. Chem. Soc. 1946, 903;
4. Woodward, R.B.; Brehm, W.J.; Nelson, A.L. J. Am. Chem. Soc. 1947, 69, 2250.
5. Robertson, J.H.; Beevers, C.A. Acta Crystallogr. 1951, 4, 270.
6. Bokhoven, C.; Schoone, J.C.; Bijvoet, J.M. Acta Crystallogr. 1951, 4, 475 (sulfate);
7. Mostad, A. Acta Chem. Scand., Sect. B. 1985, 39, 705 (nitrate);
8. R. Ghosh; Roychowdhury, P.; Chattopadhyay, D.; Iitaka, Y. Acta Crystallogr. 1989, C45, 1794 (chloride);
9. Yuan, H.S.H.; Stevens, R.C.; Bau, R.; Mosher, H.S.; Koetzle, T.F. Proc. Nat. Acad. Sci. U.S.A. 1994, 91, 12872 (iodide);
10. Bottcher, P.; Buchkremer-Hermans, H. Z. Naturforsch. B, Chem. Sci. 1987, 42, 431 (hexasulflde);
11. Bialońska, A.; Ciunik, Z. Acta Crystallogr. 2005, C61, o161 (perchlorate, hydrogen sulfate, dihydrogenphosphate);
12. Bialońska, A.; Ciunik, Z. Acta Crystallogr. 2005, E61, o4222 (brucinium sulfate heptahydrate).
13. 2O (1/4) and (1/5.25)],
14. 2O (1/1/2)];
15. Mostad, A. Acta Chem. Scand. B, 1985, 39, 705 (strychnine);
16. 2CO (1/1)];
17. Sake Gowda, D.S.; Cartz, L.; Natarajan, S. Acta Crystallogr., 1973, B29, 2760 (strychnine sulfonate);
18. Mostad, A. Acta Chem. Scand. B 1986, 306, 64 (20,21-dihydrostrychnine);
19. Mostad, A. Acta Chem. Scand. A 1988, 42, 391 (pseudostrychnine);
20. Beddoes, R.L.; Gorman, A.A.; Prescott, A.L. Acta Crystallogr. 1994, C50, 447 (neostrychnine);
21. Maurin, J.K.; Lis, T.; Zawadzka, A.; Czamocki, Z. Acta Crystallogr. 2006, E62, o694 (strychnidine hydrogen succinate).
22. Gould, R.O.; Kelly, R; Walkinshaw, M.D. J. Chem. Soc., Perkin Trans. 2 1984, 847;
23. Gould, R. O; Walkinshaw, M.D. J. Am. Chem. Soc. 1984, 106, 7840 (N-benzoyl-D- and L-alanines);
24. Bialońska, A.; Ciunik, Z. CrystEngComm 2004, 6, 276 (N-phthaloyl-D- and -L-alanines);
25. Gould, R.O.; Taylor, P.; Walkinshaw, M.D. Acta Crystallogr. 1987, C43, 2405 (N-acetyl-L-tryptophane);
26. Kuwata, S.; Tanaka, J.; Onda, N.; Yamada, T.; Miyazawa, T.; Sugiura, M.; In, Y.; Doi, M.; Inoue, M.; Ishida, T. Bull. Chem. Soc. Jap. 1993, 66, 1501 (N-phthaloyl-α-hydroxy-D- and L-leucines),
27. Biolonska, A.; Ciunik, Z. CrystEngComm. 2006, 8, 640 [N-(5-nitrobenzoyl- and N-(3, 5-dinitrobenzoyl)-D-and L-ananines].
28. Gould, R.O.; Taylor, P.; Walkinshaw, M.D.; Bruins Slot, H.J. Acta Crystallogr. 1987, C43, 2405 (D- and L-tartaric acids with strychnine);
29. Smith, G.; Wermuth, U.D.; White, J.M. Acta Crystallogr. 2006, C62, o353. (L-malic and L-tartaric acids with brucine);
30. Dijksma, F.J.J.; Gould, R.O.; Parsons, S.; Taylor, P.; Walkinshaw, M.D. Chem. Commun. 1998, 745 (α,β-D-glucuronic and α,β-D- galacturonic acids);
31. Gould, R.O.; Walkinshaw, M.D.; Wimmer, N.; Kosma, P. Acta Crystallogr. 2002, A58, C-126 (a disaccharide acid);
32. Quinkert, G.; Schmalz, H. -G; Dzierzynski, E.M.; Durner, G.; Batz, J.W. Angew. Chem. Int. Ed. Engl. 1986, 25, 992([(-)-jasmonate methyl ester];
33. Wright, J.L.; Caprathe, B.W.; Downing, D.M.; Glase, S.A.; Heffner, T.G.; Jaen, J.C.; Johnson, S.J.; Kesten, S.R.; MacKenzie, R.G.; Meltzer, L.T.; Pugsley, T.A.; Smith, S.J.; Wise, L.D.; Wustrow, D.J. J. Med. Chem. 1994, 151, 3523 (3-oxocyclohexanecarboxylic acid);
34. Krajewski, K.; Ciunik, Z. Pol. J. Chem. 1999, 73, 1687 [(+)-cyclohexene-1-carboxylic acid];
35. Andersson, M.; Sundell, S.; Allenmark, S. Enantiomer 1999, 4, 411 [(+)-Z-ethylsulfinyl-but-2-enoic acid];
36. Allenmark, S.; Skogsberg, U. Enantiomer 2000, .5, 451 (Z-acenaphthalen-1,2-dicarboxylic acid);
37. Boiadjiev, S.E.; Person, R.V.; Puzicha, G.; Knobler, C.; Maverick, E.; Trueblood, K.N.; Lightner, D.A. J. Am. Chem. Soc. 1992, 114, 10123 [( + )-(S)-3-{2,4-dimethyl-5-(ethoxycarbonyl)-1H-pyrrol-3-yl}butanoic acid];
38. Costente, J.; Ehlinger, E.; Perrin, M; Collett, A. Enantiomer 1996, 1, 377 [( + )-bromochlorofluoroacetic acid];
39. Yuan, H.S.H.; Stevens, R.; Bau, R.C.; Mosher, H.S.; Koetzle, T. F. Proc. Nat. Acad. Sci. U.S.A. 1994, 91, 12872 (a phthalolyl-substituted neopentylcarboxylic acid);
40. Laursen, J.B.; Jorgensen, C.G.; Nielsen, J. Biorg. Med. Chem. 2003, 11, 723 [(-)-(R)saphenic acid];
41. Bialońska, A.; Ciunik, Z.; Popek, T.; Lis, T. Acta Crystallogr. 2005, C61, 088 (L-glyceric acid);
42. Berkman, C.F.; Fernandez, E.J.; Thompson, CM.; Pavkovic, S.F. Acta Crystallogr. 1993, C49, 554 (a phosphodithiol, with 19-methylstrychnine).
43. Toda, F.; Tanaka, K.; Ueda, H. Tetrahedron Lett. 1981, 22, 4669 [1-(2-bromophenyl)-1-phenyl-2-prqpyn-1-ol];
44. Toda, F.; Tanaka, K.; Ueda, H.; Oshima, T. Israel J. Chem. 1985, 25, 338 (3-methyl-1-penten-3-ol);
45. Tanaka, K.; Kato, M.; Toda, F. Heterocycles 2001, 54, 405 (2-azabicyclo[2.2.1]hept-5-en-3-one);
46. Chandramohan, K.; Ravikumar, K. J. Chem. Cryst. 1999, 29, 121 (pantolactone);
47. Yamagishi, M.; Yamada, Y.; Ozaki, K.; Da-te, T.; Okamura, K.; Suzuki, M.; Matsumoto, K. J. Org. Chem. 1992, 57, 1568 [(+)-3-methylspiro[imidazolidine-4, 4′-(1′H)-quinazoline-2,2′,5-(3′H)-trione];
48. Pinkerton, A.A.; Carrapt, P. -A; Claret, F.; Vogel, P. Acta Crystallogr. 1993, C49, 1632 (2-hydroxybicyclo[2.2.1]hept-5-ene-2-carbonitrile and 2-hydroxy-7-oxabicyclo[2.2. 1]hept-5-ene-2-carbonitrile);
49. Lineberry, A.M.; Wheeler, K.A. Acta Crystallogr. 2006, E02, o3870 [(s)-2 = (2-bromophenoxy)propionic acid (with strychnine)].
50. Oshikawa, T.; Pochamroen, S.; Takai, N.; Ide, N.; Takemoto, T.; Yamashita, M. Heterocyclic Commun. 2002, 8, 271 (3-nitrobenzoic acid).
51. Sada, K.; Yoshikawa, K.; Miyata, M. Chem. Commun. 1998, 1763 (4-hydroxybenzoic acid);
52. Guo, W. -S.; Guo, F.; Deng, M.; Ge, C. -H.; Liu, Q. -T.; Hua, X. -Q.; Bai, J. -L.; Tian, Z. -Y.: Wang, S. -C.; Zheng, Q. -T. Huaxue Xuebao 2001, 59, 284 (4-nitrophenol);
53. Dijksma, F.J. J.; Gould, R.O.; Parsons, S.; Walkinshaw, M.D. Acta Crystallogr. 1998, C54, 1948 (fumaric and maleic acids);
54. Bao, J.; Wulff, W.D.; Dominy, J.B.; Fumo, M.J.; Grant, E.B.; Rob, A.C.; Whitcomb, M.C.; Yeung, S. -M.; Ostrander, R.L.; Rheingold, A.L. J. Am. Chem. Soc. 1996, 118, 3392 [2,2′-bis(3-phenyl-1-naphthol)phosphoric acid];
55. Cheung, E.; Netherton, M.R.; Scheffer, J.R.; Trotter, J. Tetrahedron Lett. 1999, 40, 8733 (2,2-dimethyl-1-oxonaphthalene-4-carboxylic acid).
56. Smith, G.; Wermuth, U.D.; Healy, P.C.; White, J.M. Acta Crystallogr. 2006, C62, o537.
57. Smith, G.; Wermuth, U.D.; Young, D.J.; Healy, P.C. Acta Crystallogr. 2005, E61, o2008.
58. Smith, G.; Wermuth,U.D.; Healy,P.C.; Young, D.J.; White, J.M. Acta Crystallogr. 2005, E61, o2646.
59. Smith, G.; Wermuth, U.D.; White, J.M. Acta Crystallogr. 2005, C61, o464.
60. Smith, G.; Wermuth, U.D.; Young, D.J.; White, J.M. Acta Crystallogr. 2004, E60, o2010.
61. Huffman, C.W.; Skelly, W.G. Chem. Rev. 1960, 63, 625;
62. Radke, F.H.; Fearing, R.B.; Fox, S.W. J. Am. Chem. Sor. 1954, 86, 2801.
63. Ravishankar, R.; Chandra, N.R.; Vijayan, M. J. Biomet. Struct. Dynamics 1998, 18, 1093 (L- and DL-arginine with maleic acid);
64. Alagar, M.; Krishnakumar, R.V.; Rajagopal, K.; Nandhini, M.; Natarajan, K. Acta Crystallogr. 2003, E59, o952 (L-phenylalanine with fumaric acid);
65. Alagar, M.; Krishnakumar, R.V.; Subha Nandhini, M.; Natarajan, K. Acta Crystallogr. 2003, E59, o857 (DL-valine with fumaric acid).
66. Altomare, A.; Cascarno, G.; Giocovasso, C.; Guagliardi, A.; Burla, M.C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
67. Sheldrick, G.M. SHELXL 97: Program for Crystal Structure Refinement, University of Göttingen, Germany.
68. TeXsan for Windows: Structure Analysis Software. Version 1.06, 1999. Molecular Structure Corporation, New Trails Drive, The Woodlands, TX77381, USA.
69. Peerdeman, A.F. Acta Crystallogr. 1956, 9, 824.
70. Eliel, E.L. Stereochemistry of Carbon Compounds, McGraw-Hill: New York, 1962, pp. 92-94.
71. Spek, A.L. PLATON: A Multipurpose Ciystallographic Tool. J. Appl. Crystallogr. 2003, 36, 7.
72. Flack, H.D. Acta. Crystallogr. 1983, A39, 876.