Determination of the structure of the violet pigment C22H 12Cl2N6O4 from a non-indexed X-ray powder diagram

Acta Crystallographica Section B: Structural Science

Volumn 61, Issue 1, 2005, Pages 37-45

  Schmidt, Martin U ^a   Ermrich, Martin ^b   Dinnebier, Robert E ^c  

^a GOETHE UNIVERSITY   (Germany)

^b X ray Laboratory Dr Ermrich   (Germany)

^c MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL LATTICES; CRYSTALLIZATION; CRYSTALLOGRAPHY; HYDROGEN; ORGANIC COMPOUNDS; PIGMENTS; X RAY POWDER DIFFRACTION;

LATTICE ENERGY; METHYLBENZIMIDAZOLONODIOXAZINE; SPACE GROUPS; X-RAY POWDER DIAGRAMS;

CRYSTAL STRUCTURE;

6,14 DICHLORO 3,11 DIMETHYL 1,3,9,11 TETRAHYDRO 5,13 DIOXA 7,15 DIAZADIIMIDAZO (4,5 B:4',5' M)PENTACENE 2,10 DIONE; 6,14-DICHLORO-3,11-DIMETHYL-1,3,9,11-TETRAHYDRO-5,13-DIOXA-7,15-DIAZADIIMIDAZO-(4,5-B:4',5'-M)PENTACENE-2,10-DIONE; FUSED HETEROCYCLIC RINGS; PIGMENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; X RAY DIFFRACTION;

HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIGMENTS, BIOLOGICAL; X-RAY DIFFRACTION;

EID: 22844441788     PISSN: 01087681     EISSN: None     Source Type: Journal    
DOI: 10.1107/S010876810402693X     Document Type: Article

References (65)

1. Allen, F. H., Motherwell, W. D. S., Raithby, P. R., Shields, G. P. & Taylor, R. (1999). New J. Chem., pp. 25-34.
2. Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. C. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339-340.
3. Bayer, T., Lewis, T. & Price, S. L. (2001). CrystEngComm. 44, 1-27.
4. Belsky, V. K., Zorkaya, O. N. & Zorky, P M. (1995). Acta Cryst. A51, 473-81.
5. Boeglin, P., Kaul, B. L. & Kempter, P. (1998). European Patent EP 0911 337 A1.
6. Bond, A. D. & Jones, W. (2002). Acta Cryst. B58, 233-243.
7. Cambridge Structural Database (1999). Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, England.
8. Cascarano, G., Favia, L. & Giacovazzo, C. (1992). J. Appl. Cryst. 25, 310-317.
9. Chan, F. C., Anwar, J., Cernik, R., Barnes, P. & Wilson, R. M. (1999). J. Appl. Cryst. 32, 436-441.
10. Chernikova, N. Yu., Belsky, V. K. & Zorky, P. M. (1990). Zh. Strukt. Khim. 31, 148-153.
11. Chernyshev, V. V. & Schenk, H. (1998). Z. Kristallogr. 213, 1-3.
12. Cheung, E. Y., McCabe, E. E., Harris, K. D. M., Johnston, R. L., Tedesco, E., Raja, K. M. P. & Balaram, P. P. (2002). Angew. Chem. 114, 512-514.
13. David, W. I. F., Shankland, K. & Shankland, N. (1998). Chem. Commun. pp. 931-932.
14. Dietz, E. & Paulus, E. F. (1991). Presentation on the Farbensymposium, Montreux.
15. Dinnebier, R. E., Sieger, P., Nar, H., Shankland, K. & David, W. I. F. (2000). J. Pharm. Sci 89, 1465-1479.
16. Dorset, D. L. (1996). Acta Cryst. B52, 753-769.
17. Eijck, B. P. van (2002). J. Comput. Chem. 23, 456-462.
18. Engel, G. E., Wilke, S., König, O., Harris, K. D. M. & Leusen, F. J. J. (1999). J. Appl. Cryst. 32, 1169-1179.
19. Erk, P. (2002). High Performance Pigments, edited by H. M. Smith, pp. 103-123. Weinheim: Wiley-VCh.
20. Fagan, P. G., Hammond, R. B., Roberts, K. J., Docherty, R., Chorlton, A. P., Jones, W. & Potts, G. D. (1995). Chem. Mater. 7, 2322-2326.
21. Gavezzotti, A. & Filippini, G. (1996). J. Am. Chem. Soc. 118, 7153-7157.
22. Hammond, R. B., Roberts, K. J., Docherty, R., Edmondson, M. & Gairns, R. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 1527-1528.
23. Harris, K. D. M. & Tremayne, M. (1996). Chem. Mater. 8, 2554-2570.
24. Harris, K. D. M., Tremayne, M. & Kariuki, B. M. (2001). Angew. Chem. 113, 1674-1700.
25. Herbst, W. & Hunger, K. (2004). Industrial Organic Pigments, 3rd ed. Weinheim: Wiley-VCH.
26. Howell, J., Rossi, A., Wallace, D., Haraki, K. & Hoffmann, R. (1977). ICON, FORTICON Version 8, QCPE program No. 517. Quantum Chemical Programs Exchange 11, p. 344.
27. Hunger, K., Paulus, E. F. & Weber, D. (1982). Farbe Lack, 88, 453-458.
28. Kaul, B. L. & Kempter, P. (1993). German Patent DE 44 42 291 A1.
29. Keller, E. (1999). SCHAKAL99. Kristallographisches Institut der Universität Freiburg, Freiburg, Germany.
30. Kempster, C. J. E. & Lipson, H. (1972). Acta Cryst. B28, 3674.
31. Kempter, P. & Wilker, G. (2001). Farbe Lack, 107, 29-31.
32. Kempter, P., Schmidt, M. U. & Born, R. (2002). European Patent EP 1199309 A1.
33. Kitajgorodskij, A. I. (1970). Adv. Struct. Res. Diffr. Methods 3, 179-247.
34. Kolb, U. (2001). Unpublished results.
35. Kolb, U. & Matveeva, G. N. (2003). Z. Kristallogr. 218, 1-10.
36. Lasocha, W., Czapkiewicz, J., Milart, P. & Schenk, H. (2001). Z. Kristallogr. 216, 291-294.
37. Lommerse, J. P. M., Motherwell, W. D. S., Ammon, H. L., Dunitz, J. D., Gavezzotti, A., Hofmann, D. W. M., Leusen, F. J. J., Mooij, W. T. M., Price, S. L., Schweizer, B., Schmidt, M. U., van Eijck, B. P., Verwer, P. & Williams, D. E. (2000). Acta Cryst. B56, 697-714.
38. Louer, D., Louër, M., Dzyabchenko, V. A., Agafonov, V. & Ceolin, R. (1995). Acta Cryst. B51, 182-187.
39. MacLean, E. J., Tremayne, M., Kariuki, B. M., Harris, K. D. M., Iqbal, A. F. M. & Hao, Z. (2000). J. Chem. Soc. Perkin Trans. 2, pp. 1513-1519.
40. Masciocchi, N., Sironi, A., Chardon-Noblat, S. & Deronzier, A. (2002). Organometallics, 21, 4009-4012.
41. McArdle, P., Gilligan, K., Cunningham, D., Dark, R. & Mahon, M. (2004). CrystEngComm 6, 303-309.
42. Motherwell, W. D. S., Ammon, H. L., Dunitz, J. D., Dzyabchenko, A., Erk, P., Gavezzotti, A., Hofmann, D. W. M., Leusen, F. J. J., Lommerse, J. P. M., Mooij, W. T. M., Price, S. L., Scheraga, H., Schweizer, B., Schmidt, M. U., van Eijck, B. P., Verwer, P. & Williams, D. E. (2002). Acta Cryst. B58, 647-661.
43. Motherwell, W. D. S., Day, G., Ammon, H. L., Boerrigter, S., Della Valle, R., Dunitz, J. D., Dzyabchenko, A., van Eijck, B. P., Erk, P., Facelli, J., Gavezzotti, A., Hofmann, D. W. M., Leusen, F. J. J., Liang, C., Price, S. L., Scheraga, H., Schweizer, B., Schmidt, M. U., Verwer, P. et al. (2005). In preparation.
44. Paulus, E. F. (1997). Personal communication.
45. Pidcock, E., Motherwell, W. D. & Cole, J. C. (2003). Acta Cryst. B59, 634-640.
46. Putz, H., Schön, J. C. & Jansen, M. (1999). J. Appl. Cryst. 32, 864-870.
47. Reck, G., Kretschmer, R. G., Kutschabsky, L. & Pritzkow, W. (1988). Acta Cryst. A44, 417-421.
48. Rietveld, H. M. (1967). Acta Cryst. 22, 151-152.
49. Rietveld, H. M. (1969). J. Appl. Cryst. 2, 65-71.
50. Rodriguez-Carjaval, J. (1990). VX Congress of the IUCr, Satellite Meeting on Powder Diffraction, Toulouse. Abstracts, p. 127.
51. Schmidt, M. U. (1995). Kristallstrukturberechnungen metallorganischer Molekülverbindungen. Verlag Shaker: Technical University of Aachen, Germany. ISBN 3-8265-0588-3.
52. Schmidt, M. U. (1999). Crystal Engineering: From Molecules and Crystals to Materials, edited by D. Braga, F. Grepioni & A. G. Orpen, pp. 331-348. Dordrecht: Kluwer Academic Publishers.
53. Schmidt, M. U. & Dinnebier, R. E. (1999). J. Appl Cryst. 32, 178-186.
54. Schmidt, M. U. & Dinnebier, R. E. (2005). In preparation.
55. Schmidt, M. U. & Englert, U. (1996). J. Chem. Soc. Dalton Trans. pp. 2077-2082.
56. Schmidt, M. U. & Kalkhof, H. (1999). CRYSCA. Clariant GmbH, Pigments Research, Frankfurt am Main, Germany.
57. Schmidt, M. U., Kempter, P., Plug, C. & Born R. (2002). European Patent EP 1201718 A1.
58. Shirley, R. (1980). Accuracy in Powder Diffraction, edited by S. Block & C. R. Hubbard, NBS Special Publication 567, pp. 361-382. Darmstadt: STOE. See also http://www.ccp14.ac.uk/.
59. Spieß, H. & Brown, S. P. (1999). Unpublished results.
60. STOE (2000). WinXPOW, Version 1.07. STOE, Darmstadt, Germany.
61. Streek, J. van de (2005). In preparation.
62. Verwer, P. & Leusen, F. J. J. (1998). Rev. Comput. Chem. 12, 327-365.
63. Visser, J. W. (1969). J. Appl. Cryst. 2, 89-95.
64. Voigt-Martin, I. G., Li, G., Kolb, U., Kothe, H., Yakimanski, A. V., Tenkovtsev, A. V. & Gilmore, C. (1999). Phys. Rev. B, 59, 6722-6735.
65. Wagner, K., Hirschler, J. & Egert, E. (2001). Z. Kristallogr. 216, 565-572.