Crystal engineering on industrial diaryl pigments using lattice energy minimizations and X-ray powder diffraction

Journal of Physical Chemistry B

Volumn 111, Issue 33, 2007, Pages 9722-9732

  Schmidt, Martin U ^a   Dinnebier, Robert E ^b   Kalkhof, Holger ^c  

^a GOETHE UNIVERSITY   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

^c Jerini AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CONSTRAINT THEORY; CRYSTAL ENGINEERING; HYDROGEN; OPTIMIZATION; QUANTUM THEORY; RIETVELD REFINEMENT; X RAY POWDER DIFFRACTION;

DIARYL AZO PIGMENTS; LATTICE ENERGY;

PIGMENTS;

EID: 34548564170     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp071731p     Document Type: Article

References (72)

1. Herbst, W.; Hunger, K. Industrial Organic Pigments, 3rd ed.; Wiley-VCH: Weinheim, Germany, 2004.
2. Mass spectrometrical analysis of a small piece of the cover of the printed edition of The Journal of Physical Chemistry B.
3. Colorants for Printing Inks; Technical information brochure, Clariant GmbH: Frankfurt am Main, 1999; update, 2000.
4. Le Bail, A. Structure Determination from Powder Diffraction -Database, http://sdpd.univ-lemans.fr/iniref.html (2007).
5. Rietveld, H. M. Acta Crystallogr. 1967, 22, 151.
6. Rietveld, H. M. J. Appl. Crystallogr. 1969, 2, 65.
7. Cascarano, G.; Favia, L.; Giacovazzo, C. J. Appl. Crystallogr. 1992, 25, 310.
8. Altomare, A.; Burla, M. C.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. C. G.; Polidori, G.; Rizzi, R. J. Appl. Crystallogr. 1999, 32, 339.
9. Chan, F. C.; Anwar, J.; Cernik, R.; Barnes, P.; Wilson, R. M. J. Appl. Crystallogr. 1999, 32, 436.
10. Wagner, K.; Hirschler, J.; Egert, E. Z Kristallogr. 2001, 216, 565.
11. Lasocha, W.; Czapkiewicz, J.; Milan, P.; Schenk, H. Z. Kristallogr. 2001, 216, 291.
12. Harris, K. D. M.; Tremayne, M. Chem. Mater. 1996, 8, 2554.
13. Harris, K. D. M.; Tremayne, M.; Kariuki, B. M. Angew. Chem. 2001, 113, 1674;
14. Angew. Chem., Int. Ed. 2001, 40, 1626.
15. Hammond, R. B.; Roberts, K. J.; Docherty, R.; Edmondson, M.; Gairns, R. J. Chem. Soc., Perkin Trans. 2 1996, 1527.
16. Tremayne, M.; Kariuki, B. M.; Harris, K. D. M. J. Appl. Crystallogr. 1996, 29, 211.
17. Andreev, Yu. G.; Lightfoot, P.; Bruce, P. G. J. Appl. Crystallogr. 1997, 30, 294.
18. Chernyshev, V. V.; Schenk, H. Z. Kristallogr. 1998, 213, 1.
19. David, W. I. F.; Shankland, K.; Shankland, N. Chem. Commun. 1998, 931.
20. Engel, G. E.; Wilke, S.; König, O.; Harris, K. D. M.; Leusen, F. J. J. J. Appl. Crystallgr. 1999, 32, 1169.
21. Kariuki, B. M.; Calcagno, P.; Harris, K. D. M.; Philp, D.; Johnston, R. L. Angew. Chem. 1999, 111, 860;
22. Angew. Chem., Int. Ed. 1999, 38, 831.
23. Dinnebier, R. E.; Sieger, P.; Nar, H.; Shankland, K.; David, W. I. F. J. Pharm. Sci. 2000, 89, 1465.
24. 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. Acta Crystallogr., Sect. B 2000, 56, 697.
25. 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. Acta Crystallogr., Sect. B 2002, 58, 647.
26. Day, G. M.; Motherwell, W. D. S.; Ammon, H. L.; Boerrigter, S. X. M.; Della Valle, R. G.; Venuti, E.; Dzyabchenko, A.; Dunitz, J. D.; Schweizer, B.; van Eijck, B. P.; Erk, P.; Facelli, J. C.; Bazterra, V. E.; Ferraro, M. B.; Hofmann, D. W. M.; Leusen, F. J. J.; Liang, C.; Pantelides, C. C.; Karamertzanis, P. G.; Price, S. L.; Lewis, T. C.; Nowell, H.; Torrisi, A.; Scheraga, H. A.; Arnautova, Y. A.; Schmidt, M. U.; Verwer, P. Acta Crystallogr., Sect. B 2005, 61, 511.
27. Schmidt, M. U.; Ermrich, M.; Dinnebier, R. E. Acta Crystallogr., Sect. B 2005, 61, 37.
28. Schmidt, M. U.; Dinnebier, R. E. J. Appl. Crystallogr. 1999, 32, 178.
29. Schmidt, M. U. In Crystal Engineering: From Molecules and Crystals to Materials; Braga, D., Grepioni, F., Orpen, A. G., Eds. Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999; pp 331-348.
30. Schmidt, M. U.; Ermrich, M.; Dinnebier, R. E. Acta Crystallogr. Sect. B 2005, 61, 37.
31. Schmidt, M. U.; Hofmann, D. W. M.; Buchsbaum, C.; Metz, H. J. Angew. Chem. 2006, 118, 1335;
32. Schmidt, M. U.; Hofmann, D. W. M.; Buchsbaum, C.; Metz, H. J. Angew. Chem., Int. Ed. 2006, 45, 1313.
33. Christie, R. M.; Monteith, J. E.; Barrow, M. J. Surf. Coat. Int., Part B 2003, 86, 247.
34. Paulus, E. F. Z Kristallogr. 1983, 165, 137.
35. Whitaker, A. Acta Crystallogr., Sect. C 1987, 43, 2141.
36. Paulus, E. F. Unpublished results.
37. Paulus, E. F.; Rieper, W. Acta Crystallogr., Sect. A 1984, 40, C277.
38. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 1987, 2, S1.
39. Cambridge Structural Database; Cambridge Crystallographic Data Centre: 12 Union Road, Cambridge, England.
40. Ahlrichs, R.; von Arnim, M. Methods and Techniques in Computational Chemistry METECC-95; STEF: Cagliari, 1995, pp 509-554.
41. Tsusuki, S.; Tanabe, K. J. Phys. Chem. 1991, 95, 139.
42. Kalkhof, H. Dissertation, Technical University, Darmstadt, Germany, 2002.
43. Pertsin, A. J.; Kitajgorodsky, A. I. The Atom-Atom Potential Method; Springer-Verlag: New York, 1987.
44. Schmidt, M. U. In Crystal Engineering: From Molecules and Crystals to Materials; Braga, D., Orpen, G.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1999, pp 331-348.
45. Howell, J.; Rossi, A.; Wallace, D.; Haraki, K.; Hoffmann, R. Quantum Chemical Programs Exchange 1977, 11, 344; QCPE No. 517.
46. Gasteiger, J.; Marsili, M. Tetrahedron 1980, 36, 3219.
47. Schmidt, M. U. Kristallstrukturberechnungen Metallorganischer Molekülverbindungen; Verlag Shaker: Aachen, Germany, 1995.
48. Schmidt, M. U.; Kalkhof, H. CRYSCA, Program for crystal structure calculations of flexible molecules; Frankfurt am Main, 1997.
49. Schmidt, M. U.; Englert, U. J. Chem. Soc., Dalton Trans. 1996, 2077.
50. Larson, C.; von Dreele R. B. Los Alamos National Laboratory Report; LAUR 86-748, GSAS 1994, version 2002 V, 2002.
51. Le Bail, A.; Duroy, H.; Fourquet, J. L. Mater. Res. Bull. 1988, 23, 447.
52. Thompson, P.; Cox, D. E.; Hastings, J. B. J. Appl. Crystallogr. 1987, 20, 79.
53. Finger, L. W.; Cox, D. E.; Jephcoat, A. P. J. Appl. Crystallogr. 1994, 27, 892.
54. Dinnebier, R. E.; Finger, L. Z. Kristallogr. Suppl. 1998, 15, 148.
55. Dinnebier, R. E. Powder Diffr. 1999, 14, 84.
56. Keller, E. SCHAKAL99. Kristallographisches Institut der Universität: Freiburg, 1999.
57. Werner, P.-E. Z. Kristallogr. 1964, 120, 375.
58. Kempster, C. J. E.; Lipson, H. Acta Crystallogr., Sect. B 1972, 28, 3764.
59. International Tables for Crystallography, Volume A: Space group symmetry, 5th ed.; Hahn, T., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2000.
60. Belsky, V. K.; Zorkaya, O. N.; Zorky, P. M. Acta Crystallogr., Sect. A 1995, 51, 473.
61. Schmidt, M. U. In Colour Science '98, Vol. 1: Dye and Pigment Chemistry; Griffiths, J. Ed.; University of Leeds: Leeds, U.K. 1999, pp 72-81; ISBN 0-85316-196-8.
62. Barrow, M. J.; Christie, R. M.; Lough, A. J.; Monteith, J. E.; Standring, P. N. Dyes Pigm. 2000, 45, 153.
63. Schmidt, M. U.; Dinnebier, R. E.; Kalkhof, H. Z. Kristallogr. Suppl. 1998, 15, 72.
64. Schmidt, M. U.; Dinnebier, R. E. Presentation at the IUCr-XVIII Conference, Glasgow, U.K., August 4-13, 1999.
65. Schmidt, M. U.; Dinnebier, R. E.; Kalkhof, H. Presentation at the 19th European Crystallographic Meeting, Nancy, France, August 26-31, 2000; p 129.
66. Barrow, M. J.; Christie, R. M.; Monteith, J. E. Dyes Pigm. 2002, 55, 79.
67. Barrow, M. J.; Christie, R. M.; Badcock, T. D. Dyes Pigm. 2003, 57, 99.
68. Christie, R. M.; Standring, P. N. Dyes Pigm. 1989, 11, 109.
69. Tuck, B.; Stirling, J. A.; Farnocchi, C. J.; McKay, R. B. (Ciba SC), European Patent EP 0790282 A2, 1997.
70. Kawamura, T. Japanese Patent JP 62153353, 1987.
71. Tanaka, K.; Takagi, K.; Haginoya, M.; Nakazima, E. Shikizai Kyokaishi 1963, 36, 392.
72. Ott, U. (Clariant), personal communication.