Modeling the interplay of inter- and intramolecular hydrogen bonding in conformational polymorphs

Journal of Chemical Physics

Volumn 128, Issue 24, 2008, Pages

  Karamertzanis, Panagiotis G ^a,e   Day, Graeme M ^b   Welch, Gareth W A ^a   Kendrick, John ^c   Leusen, Frank J J ^c   Neumann, Marcus A ^d   Price, Sarah L ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c UNIVERSITY OF BRADFORD   (United Kingdom)

^d Avant garde Materials Simulation   (France)

^e IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE DENSITY; CONFORMATIONS; CORRELATION METHODS; DENSITY FUNCTIONAL THEORY; DISPERSION (WAVES); ELECTRONIC STRUCTURE; ENERGY EFFICIENCY; EXCHANGE INTERACTIONS; FORECASTING; HYDROGEN; MOLECULAR ORBITALS; MOLECULES; POLARIZATION; POLYMORPHISM; POWDERS; SYSTEM STABILITY; TELEMETERING SYSTEMS;

AB INITIO; AMERICAN INSTITUTE OF PHYSICS (AIP); CONDENSED PHASES; DENSITY-FUNCTIONAL METHODS; DISPERSION INTERACTIONS; ELECTRON DENSITIES; ELECTRONIC STRUCTURE METHODS; EXCHANGE-CORRELATION (XC) FUNCTIONALS; FLEXIBLE MOLECULES; HYDROGEN BONDINGS; INTERMOLECULAR HYDROGEN BONDINGS; INTRAMOLECULAR HYDROGEN BONDING (IHB); LATTICE (CO); PERIODIC DENSITY; PLANE WAVE BASIS; QUALITATIVE DIFFERENCES; RELATIVE ENERGIES; SIMULATION STUDIES; SPATIAL ARRANGEMENTS; STRUCTURAL DEVIATIONS;

HYDROGEN BONDS;

DRUG; ORGANIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; CRYSTALLIZATION; HYDROGEN BOND;

COMPUTER SIMULATION; CRYSTALLIZATION; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANIC CHEMICALS; PHARMACEUTICAL PREPARATIONS;

EID: 46149086591     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.2937446     Document Type: Article

References (98)

1. G. M. Day, T. G. Cooper, A. J. Cruz Cabeza, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 (in preparation).
2. M. A. Neumann and M. A. Perrin, J. Phys. Chem. B JPCBFK 1089-5647 10.1021/jp050121r 109, 15531 (2005).
3. M. A. Neumann, F. J. J. Leusen, and J. Kendrick, Angew. Chem., Int. Ed. ACIEF5 1433-7851 10.1002/anie.200704247 47, 2427 (2008).
4. F. H. Allen, S. E. Harris, and R. Taylor, J. Comput.-Aided Mol. Des. JCADEQ 0920-654X 10.1007/BF00355046 10, 247 (1996).
5. H. Nowell and S. L. Price, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/S0108768105018549 61, 558 (2005).
6. G. M. Day, W. D. S. Motherwell, and W. Jones, Phys. Chem. Chem. Phys. PPCPFQ 1463-9076 10.1039/b612190j 9, 1693 (2007).
7. B. P. van Eijck, W. T. M. Mooij, J. Kroon, J. Phys. Chem. B JPCBFK 1089-5647 10.1021/jp012366j 105, 10573 (2001).
8. D. Buttar, M. H. Charlton, R. Docherty, J. Starbuck, J. Chem. Soc., Perkin Trans. 2 JCPKBH 0300-9580 1998, 763.
9. G. M. Day, " Lattice dynamical studies of molecular crystals with application to polymorphism and structure prediction.," Ph.D. thesis, University College London, 2003.
10. C. K. Leech, S. A. Barnett, K. Shankland, N. Gutmann, and C. C. Wilson, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/ S0108768106025821 62, 926 (2006).
11. A. R. Oganov and C. W. Glass, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.2210932 124, 244704 (2006).
12. B. Civalleri, K. Doll, and C. M. Zicovich-Wilson, J. Phys. Chem. B JPCBFK 1089-5647 10.1021/jp065757c 111, 26 (2007).
13. M. A. Spackman and A. S. Mitchell, Phys. Chem. Chem. Phys. PPCPFQ 1463-9076 10.1039/b009159f 3, 1518 (2001).
14. J. A. Chisholm, S. Motherwell, P. R. Tulip, S. Parsons, and S. J. Clark, Cryst. Growth Des. CGDEFU 1528-7483 10.1021/cg0496235 5, 1437 (2005).
15. B. Civalleri, C. M. Zicovich-Wilson, L. Valenzano, and P. Ugliengo, CrystEngComm 10, 405 (2008).
16. S. Y. Ahn, F. Guo, B. M. Kariuki, and K. D. M. Harris, J. Am. Chem. Soc. JACSAT 0002-7863 10.1021/ja0573155 128, 8441 (2006).
17. R. Dovesi, B. Civalleri, R. Orlando, C. Roetti, and V. R. Saunders, Rev. Comput. Chem. RCCHEY 1069-3599 10.1002/0471720895.ch1 21, 1 (2005).
18. M. C. Payne, M. P. Teter, D. C. Allan, T. A. Arias, and J. D. Joannopoulos, Rev. Mod. Phys. RMPHAT 0034-6861 10.1103/RevModPhys.64.1045 64, 1045 (1992).
19. A. Burger and R. Ramberger, Mikrochim. Acta MIACAQ 0026-3672 10.1007/BF01197379 2, 259 (1979).
20. A. Burger and R. Ramberger, Mikrochim. Acta MIACAQ 0026-3672 10.1007/BF01197380 2, 273 (1979).
21. S. A. Barnett, D. A. Tocher, and M. Vickers, CrystEngComm 8, 313 (2006).
22. L. A. Errede, M. C. Etter, R. C. Williams, and S. M. Darnauer, J. Chem. Soc., Perkin Trans. 2 JCPKBH 0300-9580 1981, 233.
23. See EPAPS Document No. E-JCPSA6-128-022823 for figure showing the iterative convergence of induction energy estimates; figure showing the convergence of BSSE for periodic, atom-centered, Gaussian basis set DFT calculations; figure showing the intramolecular energy basis set dependence for oxalyl dihydrazide polymorph a; a discussion on the applicability of the heat of transition rule for ortho-acetamidobenzamide; figures showing the basis for the choice of basis set cutoff and k -point spacing for CASTEP calculations; tables showing the reproduction of the flexible torsion angles identified in Scheme during monomer+model and quantum mechanical relaxed-cell crystal energy minimizations; and table showing the variation of intermolecular, conformational, and BSSE contributions to crystal energy with Hamiltonian and basis set for fixed-cell quantum mechanical optimizations. For more information on EPAPS, see http://www.aip.org/pubservs/epaps.html.
24. J. B. Clark, J. W. Hastie, L. H. E. Kihlborg, R. Metselaar, and M. M. Thackeray, Pure Appl. Chem. PACHAS 0033-4545 10.1351/pac199466030577 66, 577 (1994).
25. J. Bernstein, Polymorphism in Molecular Crystals (Clarendon, Oxford, 2002).
26. P. G. Karamertzanis and S. L. Price, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct600111s 2, 1184 (2006).
27. M. J. Frisch, G. W. Trucks, H. B. Schlegel, GAUSSIAN 03, Gaussian, Inc., Wallingford, CT, 2003
28. D. J. Willock, S. L. Price, M. Leslie, and C. R. A. Catlow, J. Comput. Chem. JCCHDD 0192-8651 10.1002/jcc.540160511 16, 628 (1995).
29. A. J. Stone, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct050190+ 1, 1128 (2005).
30. S. R. Cox, L. Y. Hsu, and D. E. Williams, Acta Crystallogr., Sect. A: Cryst. Phys., Diffr., Theor. Gen. Crystallogr. ACACBN 0567-7394 10.1107/S0567739481000703 37, 293 (1981).
31. D. E. Williams and S. R. Cox, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/S010876818400238X 40, 404 (1984).
32. D. S. Coombes, S. L. Price, D. J. Willock, and M. Leslie, J. Phys. Chem. JPCHAX 0022-3654 10.1021/jp960333b 100, 7352 (1996).
33. P. Hobza and J. Sponer, J. Am. Chem. Soc. JACSAT 0002-7863 10.1021/ja026759n 124, 11802 (2002).
34. P. Jurecka and P. Hobza, J. Am. Chem. Soc. JACSAT 0002-7863 10.1021/ja036611j 125, 15608 (2003).
35. G. W. A. Welch, P. G. Karamertzanis, A. J. Misquitta, A. J. Stone, and S. L. Price, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct700270d 4, 522 (2008).
36. C. M. Breneman and K. B. Wiberg, J. Comput. Chem. JCCHDD 0192-8651 10.1002/jcc.540110311 11, 361 (1990).
37. A. J. Stone, The Theory of Intermolecular Forces, 1st ed. (Clarendon, Oxford, 1996).
38. R. Dovesi, V. R. Saunders, C. Rosetti, R. Orlando, C. M. Zicovich-Wilson, F. Pascale, B. Civalleri, K. Doll, N. M. Harrison, I. J. Bush, Ph. D'Arco, and M. Llunell, CRYSTAL06 User's Manual, University of Turin, Turin, January 31, 2008.
39. J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett. PRLTAO 0031-9007 10.1103/PhysRevLett.77.3865 77, 3865 (1996).
40. A. D. Becke, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.464913 98, 5648 (1993).
41. C. T. Lee, W. T. Yang, and R. G. Parr, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.37.785 37, 785 (1988).
42. C. Adamo and V. Barone, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.478522 110, 6158 (1999).
43. A. Schafer, H. Horn, and R. Ahlrichs, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.463096 97, 2571 (1992).
44. S. F. Boys and F. Bernardi, Mol. Phys. MOPHAM 0026-8976 10.1080/00268977000101561 19, 553 (1970).
45. A. K. Rappe and W. A. Goddard, J. Phys. Chem. JPCHAX 0022-3654 10.1021/j100161a070 95, 3358 (1991).
46. T. van Mourik, P. G. Karamertzanis, and S. L. Price, J. Phys. Chem. A JPCAFH 1089-5639 10.1021/jp0563181 110, 8 (2006).
47. Y. Wang and J. P. Perdew, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.44.13298 44, 13298 (1991).
48. S. J. Clark, M. D. Segall, C. J. Pickard, P. J. Hasnip, M. J. Probert, K. Refson, and M. C. Payne, Z. Kristallogr. ZEKRDZ 0044-2968 10.1524/zkri.220.5. 567.65075 220, 567 (2005).
49. S. Tosoni, C. Tuma, J. Sauer, B. Civalleri, and P. Ugliengo, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.2790019 127, 154102 (2007).
50. D. Vanderbilt, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.41.7892 41, 7892 (1990).
51. M. A. Neumann, GRACE, Version 1.0, Avant-garde Materials Simulation, 2007.
52. G. Kresse and J. Hafner, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.47.558 47, 558 (1993).
53. G. Kresse and J. Furthmuller, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.54.11169 54, 11169 (1996).
54. G. Kresse and D. Joubert, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.59.1758 59, 1758 (1999).
55. S. H. Vosko, L. Wilk, and M. Nusair, Can. J. Phys. CJPHAD 0008-4204 58, 1200 (1980).
56. J. A. Chisholm and S. Motherwell, J. Appl. Crystallogr. JACGAR 0021-8898 10.1107/S0021889804027074 38, 228 (2005).
57. R. Taylor, O. Kennard, and W. Versichel, J. Am. Chem. Soc. JACSAT 0002-7863 10.1021/ja00356a010 105, 5761 (1983).
58. R. Taylor and O. Kennard, Acc. Chem. Res. ACHRE4 0001-4842 10.1021/ar00105a004 17, 320 (1984).
59. R. Taylor, O. Kennard, and W. Versichel, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/S010876818400210X 40, 280 (1984).
60. Y. Zhao and D. G. Truhlar, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct049851d 1, 415 (2005).
61. J. M. Tao and J. P. Perdew, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.1862242 122, 114102 (2005).
62. B. Montanari, P. Ballone, and R. O. Jones, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.476110 108, 6947 (1998).
63. C. Ouvrard and J. B. O. Mitchell, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/S0108768103019025 56, 676 (2003).
64. S. M. Cybulski and C. E. Seversen, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.1829044 122, 014117 (2005).
65. S. L. Price, C. H. Faerman, and C. W. Murray, J. Comput. Chem. JCCHDD 0192-8651 10.1002/jcc.540121005 12, 1187 (1991).
66. U. Koch, P. L. A. Popelier, A. J. Stone, Chem. Phys. Lett. CHPLBC 0009-2614 10.1016/0009-2614(95)00389-L 238, 253 (1995).
67. A. J. Misquitta, A. J. Stone, and S. L. Price, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct700105f 4, 19 (2008).
68. A. J. Stone and A. J. Misquitta, Int. Rev. Phys. Chem. IRPCDL 0144-235X 10.1080/01442350601081931 26, 193 (2007).
69. A. J. Misquitta, G. W. A. Welch, A. J. Stone, and S. L. Price, Chem. Phys. Lett. CHPLBC 0009-2614 10.1016/j.cplett.2008.02.113 456, 105 (2008).
70. J. F. Dobson, K. McLennan, A. Rubio, J. Wang, T. Gould, H. M. Le, and B. P. Dinte, Aust. J. Chem. AJCHAS 0004-9425 10.1071/CH01052 54, 513 (2001).
71. T. van Mourik and R. J. Gdanitz, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.1476010 116, 9620 (2002).
72. Q. Wu and W. T. Yang, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.1424928 116, 515 (2002).
73. S. X. Feng and T. L. Li, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct050189a 2, 149 (2006).
74. U. Zimmerli, M. Parrinello, and P. Koumoutsakos, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.1637034 120, 2693 (2004).
75. P. Jurecka, J. Cerny, P. Hobza, and D. R. Salahub, J. Comput. Chem. JCCHDD 0192-8651 10.1002/jcc.20570 28, 555 (2007).
76. S. Grimme, J. Comput. Chem. JCCHDD 0192-8651 10.1002/jcc.20078 25, 1463 (2004).
77. P. G. Karamertzanis, P. Raiteri, M. Parrinello, M. Leslie, and S. L. Price, J. Phys. Chem. B JPCBFK 1089-5647 10.1021/jp709764e 112, 4298 (2008).
78. A. E. Gray, G. M. Day, M. Leslie, and S. L. Price, Mol. Phys. MOPHAM 0026-8976 10.1080/00268970412331284208 102, 1067 (2004).
79. B. P. van Eijck, J. Comput. Chem. JCCHDD 0192-8651 10.1002/jcc.1047 22, 816 (2001).
80. G. M. Day, S. L. Price, and M. Leslie, J. Phys. Chem. B JPCBFK 1089-5647 10.1021/jp035125f 107, 10919 (2003).
81. S. L. Price, Adv. Drug Delivery Rev. ADDREP 0169-409X 10.1016/j.addr.2003.10.006 56, 301 (2004).
82. J. P. M. Lommerse, W. D. S. Motherwell, H. L. Ammon, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/S0108768100004584 56, 697 (2000).
83. W. D. S. Motherwell, H. L. Ammon, J. D. Dunitz, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/S0108768102005669 58, 647 (2002).
84. G. M. Day, W. D. S. Motherwell, H. L. Ammon, Acta Crystallogr., Sect. B: Struct. Sci. ASBSDK 0108-7681 10.1107/S0108768105016563 61, 511 (2005).
85. C. Ouvrard and S. L. Price, Cryst. Growth Des. CGDEFU 1528-7483 10.1021/cg049922u 4, 1119 (2004).
86. P. G. Karamertzanis and C. C. Pantelides, Mol. Phys. MOPHAM 0026-8976 10.1080/00268970601143317 105, 273 (2007).
87. F. J. J. Leusen, Cryst. Growth Des. CGDEFU 1528-7483 10.1021/cg020034d 3, 189 (2003).
88. M. D. Gourlay, J. Kendrick, and F. J. J. Leusen, Cryst. Growth Des. CGDEFU 1528-7483 10.1021/cg060364o 7, 56 (2007).
89. T. G. Cooper, W. Jones, W. D. S. Motherwell, and G. M. Day, CrystEngComm 9, 595 (2007).
90. P. G. Karamertzanis and C. C. Pantelides, J. Comput. Chem. JCCHDD 0192-8651 10.1002/jcc.20165 26, 304 (2005).
91. C. Pisani, M. Busso, G. Capecchi, S. Casassa, R. Dovesi, L. Maschio, C. Zicovich-Wilson, and M. Schutz, J. Chem. Phys. JCPSA6 0021-9606 10.1063/1.1857479 122, 094113 (2005).
92. L. Maschio, D. Usvyat, F. R. Manby, S. Casassa, C. Pisani, and M. Schutz, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.76.075101 76, 075101 (2007).
93. D. Usvyat, L. Maschio, F. R. Manby, S. Casassa, M. Schutz, and C. Pisani, Phys. Rev. B PRBMDO 0163-1829 10.1103/PhysRevB.76.075102 76, 075102 (2007).
94. E. Tapavicza, I. C. Lin, O. A. von Lilienfeld, I. Tavernelli, M. D. Coutinho-Neto, and U. Rothlisberger, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct700049s 3, 1673 (2007).
95. Y. Zhao and D. G. Truhlar, J. Chem. Theory Comput. JCTCCE 1549-9618 10.1021/ct060044j 2, 1009 (2006).
96. S. L. Price, Phys. Chem. Chem. Phys. PPCPFQ 1463-9076 10.1039/b719351c 10, 1996 (2008).
97. A. Bondi, J. Phys. Chem. JPCHAX 0022-3654 10.1021/j100785a001 68, 441 (1964).
98. A. J. Stone, A. Dullweber, O. Engkvist, E. Fraschini, M. P. Hodges, A. W. Meredith, D. R. Nutt, P. L. A. Popelier, and D. J. Wales, ORIENT, a program for studying interactions between molecules, Version 4.6, University of Cambridge, 2006.