Reassessment of large dipole moment enhancements in crystals: A detailed experimental and theoretical charge density analysis of 2-methyl-4-nitroaniline

Journal of Physical Chemistry A

Volumn 110, Issue 28, 2006, Pages 8763-8776

  Whitten, Andrew E ^a,c   Turner, Peter ^b   Klooster, Wim T ^c   Piltz, Ross O ^c   Spackman, Mark A ^d  

^a UNIVERSITY OF NEW ENGLAND   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

^c AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

^d UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANISOTROPY; ATOMS; CARRIER CONCENTRATION; DEFORMATION; ELECTRIC CHARGE; ELECTRIC FIELDS; NEUTRONS; SYSTEMATIC ERRORS;

AB INITIO CRYSTAL HARTREE-FOCK CALCULATIONS; HYDROGEN ATOMS; INTERMOLECULAR INTERACTIONS; MOLECULAR DIPOLE MOMENT;

SINGLE CRYSTALS;

EID: 33746904710     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp061830n     Document Type: Article

References (107)

1. Bosshard, C.; Sutter, K.; Prêtre, P.; Hulliger, J.; Flörsheimer, M.; Kaatz, P.; Günter, P. Organic Nonlinear Optical Materials; Gordon and Breach: Basel, 1995.
2. Prasad, P. N.; Williams, D. J. Introduction to nonlinear optical effects in molecules and polymers; Wiley: New York, 1991.
3. Sutherland, R. L. Handbook of Nonlinear Optics; Marcel Dekker: New York, 1996.
4. Zyss, J. Molecular nonlinear optics. Materials, physics and devices; Academic Press: New York, 1994.
5. Levine, B. F.; Bethea, C. G.; Thurmond, C. D.; Lynch, R. T.; Bernstein, J. L. J. Chem. Phys. 1979, 50, 2523.
6. Lipscomb, G. F.; Garito, A. F.; Nerang, R. S. J. Chem. Phys. 1981, 75, 1509.
7. Lipscomb, G. F.; Garito, A. F.; Nerang, R. S. Appl. Phys. Lett. 1981, 38, 663.
8. Ho, E. S. S.; Iizuka, K.; Freundorfer, A. P.; Wah, C. K. L. J. Appl. Phys. 1991, 69, 1173.
9. Tokura, Y.; Kurita, A.; Koda, T. Phys. Rev. B 1985, 31, 2588.
10. Monta, R.; Ogasawara, N.; Umegaki, S.; Ito, R. Jpn. J. Appl. Phys. 1987, 26, L1711.
11. Sugihara, O.; Toda, T.; Ogura, T.; Kinoshita, T.; Sasaki, K. Opt. Lett. 1991, 16, 702.
12. Paturle, A.; Graafsma, H.; Boviatsis, J.; Legrand, A.; Restori, R.; Coppens, P.; Kvick, A.; Wing, R. M. Acta Crystallogr. 1989, A45, FC25.
13. Paturle, A.; Graafsma, H.; Sheu, H.-S.; Coppens, P.; Becker, P. Phys. Rev. B 1991, 43, 14683.
14. Graafsma, H.; Paturle, A.; Wu, L.; Sheu, H. S.; Majewski, J.; Poorthuis, G.; Coppens, P. Acta Crystallogr., Sect. A 1992, 48, 113.
15. Howard, S. T.; Hursthouse, M. B.; Lehmann, C. W.; Mallinson, P. R.; Frampton, C. S. J. Chem. Phys. 1992, 97, 5616.
16. Cole, J. M. Philos. Trans. R. Soc. London, Ser. A 2003, 361, 2751.
17. Puig-Molina, A.; Alvarez-Larena, A.; Piniella, J. F.; Howard, S. T.; Baert, F. Struct. Chem. 1998, 9, 395.
18. Spackman, M. A.; Byrom, P. G. Acta Crystallogr., Sect. B 1997, 53, 553.
19. Coppens, P.; Volkov, A. Acta Crystallogr., Sect. A 2004, 60, 357.
20. Koritsanszky, T. S.; Coppens, P. Chem. Rev. 2001, 101, 1583.
21. Ritchie, J. P. Chem. Phys. Lett. 2004, 387, 243.
22. Volkov, A.; Gatti, C.; Abramov, Y.; Coppens, P. Acta Crystallogr., Sect. A 2000, 56, 252.
23. Gopalan, R. S.; Kulkarni, G. U.; Rao, C. N. R. ChemPhysChem 2000, 1, 127.
24. Kulkarni, G. U.; Kumaradhas, P.; Rao, C. N. R. Chem. Mater. 1998, 10, 3498.
25. Munshi, P.; Row: T. N. G. Acta Crystallogr., Sect. B 2002, 58, 1011.
26. Volkov, A.; Wu, G.; Coppens, P. J. Synchrotron Rad. 1999, 6, 1007.
27. Ferenczy, G. G.; Csonka, G. I.; Naray-Szabo, G.; Angyan, J. G. J. Comput. Chem. 1998, 19, 38.
28. Munn, R. W. J. Chem. Phys. 1995, 103, 850.
29. Munn, R. W.; Kelly, J. F.; Aicken, F. M. Chem. Phys. 1999, 245, 227.
30. Munn, R. W. J. Chem. Phys. 2000, 113, 8774.
31. Munn, R. W.; Malagoli, M.; Panhuis, M. I. H. Synth. Met. 2000, 109, 29.
32. Tsiaousis, D.; Munn, R. W.; Smith, P. J.; Popelier, P. L. A. Chem. Phys. 2004, 305, 317.
33. Spackman, M. A. Chem. Rev. 1992, 92, 1769.
34. Coppens, P. X-Ray Charge Densities and Chemical Bonding; Oxford University Press: New York, 1997.
35. Abramov, Y. A.; Volkov, A. V.; Coppens, P. Chem. Phys. Lett. 1999, 311, 81.
36. Gopalan, R. S.; Kulkarni, G. U.; Ravi, M.; Rao, C. N. R. New J. Chem. 2001, 25, 1108.
37. Hibbs, D. E.; Overgaard, J.; Piltz, R. O. Org. Biomol. Chem. 2003, 1, 1191.
38. Munshi, P.; Spackman, M. A. Manuscript in preparation, 2006.
39. Ferguson, G.; Glidewell, C.; Low, J. N.; Skakle, J. M. S.; Wardell, J. L. Acta Crystallogr., Sect. C 2001, 57, 315.
40. Bruker SMART, SAINT, ASTRO and XPREP- Data Collection and Processing Software for the SMART System; Bruker Analytical X-ray Instruments Inc.; Madison, WI, 1995.
41. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421.
42. Lenstra, A. T. H.; Van Loock, J. F. J.; Rousseau, B.; Maes, S. T. Acta Crystallogr., Sect. A 2001, 57, 629.
43. Rousseau, B.; Maes, S. T.; Lenstra, A. T. H. Acta Crystallogr., Sect. A 2000, 56, 300.
44. Whitten, A. E.; McKinnon, J. J.; Turner, P.; Pattison, P.; Weber, H. P.; Spackman, M. A., 2003. Data were collected at the Swiss-Norwegian beamline (BM1A) on a six-circle KUMA KM6-CH kappa diffractometer equipped with an Oxford Diffraction Onyx CCD detector. 3192 frames were collected with ω scans, with a detector-to-crystal distance of 36.0 cm. The wavelength was 0.71069 Å, and the temperature 100(2) K. The data proved unsatisfactory for charge density analysis, but served to provide a more reliable estimate of the structure factor for the (112) reflection.
45. Tachibana, M.; Sato, S.; Kojima, K. Acta Crystallogr. 1996, A52, C158.
46. Stewart, R. F.; Spackman, M. A.; Flensburg, C. VALRAY - User's Manual, 2.1 ed. Carnegie Mellon University & University of Copenhagen, 2000.
47. Cummins, P. G.; Dunmur, D. A.; Munn, R. W.; Newham, R. J. Acta Crystallogr. 1972, A32, 847.
48. Dovesi, R.; Saunders: V. R.; Roetti, C.; Causa, M.; Harrison, N.; Orlando, R.; Aprà, E. CRYSTAL98 - Users Manual, 1.0 ed.; Theoretical Chemistry Group of Torino, Italy, and CCLRC Daresbury Laboratory, England, 1998.
49. Thakkar, A. J.; Koga, T.; Saito, M.; Hoffmeyer, R. E. Int. J. Quantum Chem., Quantum Chem. Symp. 1993, 27, 343.
50. Spackman, M. A.; Byrom, P. G.; Alfredsson, M.; Hermansson, K. Acta Crystallogr., Sect. A 1999, 55, 30.
51. Spackman, M. A.; Mitchell, A. S. Phys. Chem. Chem. Phys. 2001, 3, 1518.
52. Gibbs, G. V.; Whitten, A. E.; Spackman, M. A.; Stimpfl, M.; Downs, R. T.; Carducci, M. D. J. Phys. Chem. B 2003, 107, 12996.
53. Volkov, A.; Abramov, Y. A.; Coppens, P. Acta Crystallogr., Sect. A 2001, 57, 272.
54. Whitten, A. E.; Dittrich, B.; Spackman, M. A.; Turner, P.; Brown, T. C. J. Chem. Soc., Dalton Trans. 2004, 23.
55. Spackman, M. A.; Jiang, B.; Groy, T. L.; He, H.; Whitten, A. E.; Spence, J. C. H. Phys. Rev. Lett. 2005, 95, 085502.
56. Ellena, J.; Goeta, A. E.; Howard, J. A. K.; Punte, G. J. Phys. Chem. A 2001, 105, 8696.
57. Stewart, R. F. Partitioning of Hartree-Fock Atomic Form Factors into "Core" and "Valence" Shells. In Electron and Magnetization Densities in Molecules and Solids; Becker, P., Ed.; Plenum: New York, 1980; p 427.
58. Clementi, E.; Roetti, C. At. Data Nucl. Data Tables 1974, 14, 177.
59. Stevens, E. D.; Coppens, P. Acta Crystallogr., Sect. A 1975, 31, 612.
60. Kampermann, S. P.; Ruble, J. R.; Craven, B. M. Acta Crystallogr. 1994, 650, 737.
61. Pinkerton, A. A., Personal communication.
62. Dittrich, B. Unpublished work, 2005.
63. Kocher, N.; Henn, J.; Gostevskii, B.; Kost, D.; Kalikhman, I.; Engels, B.; Stalke, D. J. Am. Chem. Soc. 2004, 126, 5563.
64. Leusser, D.; Henn, J.; Kocher, N.; Engels, B.; Stalke, D. J. Am. Chem. Soc. 2004, 126, 1781.
65. Sorensen, H. O.; Stewart, R. F.; McIntyre, G. J.; Larsen, S. Acta Crystallogr., Sect. A 2003, 59, 540.
66. Mallinson, P. R.; Koritsanszky, T.; Elkaim, E.; Li, N.; Coppens, P. Acta Crystallogr. 1988, A44, 336.
67. Becker, P. J.; Coppens, P. Acta Crystallogr., Sect. A 1974, 30, 129.
68. Spackman, M. A. J. Appl. Crystallogr. 1987, 20, 256.
69. Blessing, R. H. Acta Crystallogr., Sect. B 1995, 51, 816.
70. Whitten, A. E.; Spackman, M. A. Acta Crystallogr., Sect. B. In press.
71. Cole, J. C.; Cole, J. M.; Cross, G. H.; Farsari, M.; Howard, J. A. K.; Szablewski, M. Acta Crystallogr., Sect. B 1997, 53, 812.
72. Cole, J. M.; Copley, R. C. B.; McIntyre, G. J.; Howard, J. A. K.; Szablewski, M.; Cross, G. H. Phys. Rev. B 2002, 65.
73. International Tables for Crystallography, Volume C: Mathematical, Physical and Chemical Tables; Springer: New York, 2004.
74. Ellena, J.; Goeta, A. E.; Howard, J. A. K.; Wilson, C. C.; Autino, J. C.; Punte, G. Acta Crystallogr. 1999, B55, 209.
75. McKinnon, J. J.; Mitchell, A. S.; Spackman, M. A. Chem-Eur. J. 1998, 4, 2136.
76. Spackman, M. A.; Byrom, P. G. Chem. Phys. Lett. 1997, 267, 215.
77. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr., Sect. B 2004, 60, 627.
78. Spackman, M. A.; McKinnon, J. J. CrystEngComm 2002, 4, 378.
79. Spackman, M. A.; Byrom, P. G. Acta Crystallogr., Sect. B 1996, 52, 1023.
80. Volkov, A.; Abramov, Y. A.; Coppens, P. Acta Crystallogr. 2001, A57, 272.
81. Bader, R. F. W. Atoms in Molecules - A Quantum Theory; Oxford University Press: Oxford, 1990.
82. Bader, R. F. W.; Essen, H. J. Chem. Phys. 1984, 80, 1943.
83. Birkedal, H.; Madsen, D.; Mathiesen, R. H.; Knudsen, K.; Weber, H. P.; Pattison, P.; Schwarzenbach, D. Acta Crystallogr., Sect. A 2004, 60, 371.
84. Volkov, A.; Abramov, Y.; Coppens, P.; Gatti, C. Acta Crystallogr., Sect. A 2000, 56, 332.
85. Volkov, A.; Coppens, P. Acta Crystallogr., Sect. A 2001, 57, 395.
86. Volkov, A.; Li, X.; Koritsanszky, T.; Coppens, P. J. Phys. Chem. A 2004, 108, 4283.
87. Bach, A.; Lentz, D.; Luger, P. J. Phys. Chem. A 2001, 105, 7405.
88. Hibbs, D. E.; Overgaard, J.; Platts, J. A.; Waller, M. P.; Hursthouse, M. B. J. Phys. Chem. B 2004, 108, 3663.
89. Hibbs, D. E.; Hanrahan, J. R.; Hursthouse, M. B.; Knight, D. W.; Overgaard, J.; Turner, P.; Piltz, R. O.; Waller, M. P. Org. Biomol. Chem. 2003, 1, 1034.
90. Hibbs, D. E.; Austin-Woods, C. J.; Platts, J. A.; Overgaard, J.; Turner, P. Chem.-Eur. J. 2003, 9, 1075.
91. Spackman, M. A. Chem. Phys. Lett. 1999, 301, 425.
92. Matta, C. F.; Hernández-Trujillo, J.; Tang, T. H.; Bader, R. F. W. Chem.-Eur. J. 2003, 9, 1940.
93. Whitten, A. E.; Radford, C. J.; McKinnon, J. J.; Spackman, M. A. J. Chem. Phys. 2006, 124, 074106.
94. Bürgi, H. B.; Capelli, S. C.; Goeta, A. E.; Howard, J. A. K.; Spackman, M. A.; Yufit, D. S. Chem.-Eur. J. 2002, 8, 3512.
95. Palmer, M. H.; Sherwood, P. Z. Naturforsch. 1996, 51a, 460.
96. Stewart, R. F. J. Chem. Phys. 1972, 57, 1664.
97. Brown, A. S.; Spackman, M. A. Mol. Phys. 1994, 83, 551.
98. Aliev, A. E.; Harris, K. D. M. Probing Hydrogen Bonding in Solids Using Solid State NMR Spectroscopy. In Structure and Bonding; Springer-Verlag: Berlin, 2004; Vol. 108, p 1.
99. Barnes, R. G.; Bloom, J. W. J. Chem. Phys. 1972, 57, 3082.
100. Pyykkö, P.; Lähteenmäki, U. Ann. Univ. Turku., Ser. A 1966, 93, 2.
101. Rowell, J. C.; Phillips, W. D.; Melby, L. R.; Panar, M. J. Chem. Phys. 1965, 43, 3442.
102. Hunt, M. J.; Mackay, A. L. J. Magn. Reson. 1974, 15, 402.
103. Destro, R.; Roversi, P.; Barzaghi, M.; Marsh, R. E. J. Phys. Chem. A 2000, 104, 1047.
104. Roversi, P.; Destro, R. Chem. Phys. Lett. 2004, 386, 472.
105. Stewart, R. F.; Davidson, E. R.; Simpson, W. T. J. Chem. Phys. 1965, 42, 3175.
106. Koritsanszky, T.; Howard, S. T.; Macchi, P.; Gatti, C.; Farrugia, L. J.; Mallinson, P. R.; Volkov, A.; Su, Z.; Richter, T.; Hansen, N. K. XD - A computer program package for multipole refinement and analysis of charge densities from diffraction data, 4.10 ed.; Free University of Berlin, Germany, 2003.
107. Smith, J. W.; Walshaw, S. M. J. Chem. Soc. 1957, 4527.