Revealing non-covalent interactions in molecular crystals through their experimental electron densities

Chemistry - A European Journal

Volumn 18, Issue 48, 2012, Pages 15523-15536

  Saleh, Gabriele ^a,c   Gatti, Carlo ^b,c   Lo Presti, Leonardo ^a,b,c   Contreras García, Julia ^d  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

^c AARHUS UNIVERSITY   (Denmark)

^d SORBONNE UNIVERSITÉ   (France)

Author keywords

noncovalent interactions; quantum chemistry; reduced density gradient; solid state structures; X ray diffraction

Indexed keywords

AB INITIO; AB INITIO APPROACH; ANTI-ULCER DRUGS; BOND PATHS; COMPUTER CODES; DENSITY GRADIENTS; DESCRIPTORS; DOCKING PROCESS; ELECTRON-DENSITY GRADIENTS; EXPERIMENTAL ELECTRON DENSITY; FAMOTIDINE; FUNGAL METABOLITES; HYDROGEN BONDING NETWORK; INTERMOLECULAR INTERACTIONS; ISO SURFACE; NON-COVALENT INTERACTION; QUANTUM THEORY OF ATOMS IN MOLECULES; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE STRUCTURES; VAN DER WAALS; WEAK INTERACTIONS;

BENZENE; CARRIER CONCENTRATION; ELECTRON DENSITY MEASUREMENT; ELECTRONS; EMERGENCY ROOMS; HYDROGEN; HYDROGEN BONDS; MOLECULAR CRYSTALS; QUANTUM CHEMISTRY; QUANTUM THEORY; REGRESSION ANALYSIS; VAN DER WAALS FORCES; VISUALIZATION; X RAY DIFFRACTION;

DRUG INTERACTIONS;

ALDEHYDE; AUSTDIOL; BENZOPYRAN DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ELECTRON; HYDROGEN BOND; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; BENZOPYRANS; CRYSTALLOGRAPHY, X-RAY; ELECTRONS; HYDROGEN BONDING; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE;

EID: 84869473502     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201290     Document Type: Article

References (73)

1. J. Černý, P. Hobza, Phys. Chem. Chem. Phys. 2007, 9, 5291-5303.
2. A. L. Lehninger, D. L. Nelson, M. M. Cox, Principles of Biochemistry, 2 nd ed., Worth Publishers, New York, 1993.
3. N. Krishnamoorthy, M. A. H. A. Yacoub, S. N. Yaliraki, Biomaterials 2011, 32, 7275-7285.
4. A. Dutta, A. D. Jana, S. Gangopadhyay, K. Kumar Das, J. Marek, R. Marek, J. Brus, M. Ali, Phys. Chem. Chem. Phys. 2011, 13, 15845-15853.
5. A. Gavezzotti, Molecular Aggregation. Structure Analysis and Molecular Simulation of Crystals and Liquids, IUCr Monographs on Crystallography No. 19, Oxford University Press, Oxford, 2007.
6. H. Fenniri, M. Packiarajan, K. L. Vidale, D. M. Sherman, K. Hallenga, K. V. Wood, J. G. Stonwell, J. Am. Chem. Soc. 2001, 123, 3854-3855.
7. S. Keinan, M. A. Ratner, T. J. Marks, Chem. Phys. Lett. 2004, 392, 291-296.
8. G. R. Desiraju, Crystal Engineering, The Design of Organic Solids, Elsevier, Amsterdam, 1989.
9. G. M. Day, T. G. Cooper, A. J. Cruz-Cabeza, K. E. Hejczyk, H. L. Ammon, S. X. M. Boerrigter, J. S. Tan, R. G. Della Valle, E. Venuti, J. Jose, S. R. Gadre, G. R. Desiraju, T. S. Thakur, B. P. van Eijck, J. C. Facelli, V. E. Bazterra, M. B. Ferraro, D. W. M. Hoffmann, M A. Neumann, F. J. J. Leusen, J. Kendrick, S. L. Price, A. J. Misquitta, P. G. Karamertzanis, G. W. A. Welch, H. A. Scheraga, Y. A. Arnautova, M. U. Schmidt, J. van de Streek, A. K. Wolf, B. Schweizer, Acta Crystallogr. Sect. B 2009, 65, 107-125.
10. R. E. Rosenfield Jr, R. Parthasarathy, J. D. Dunitz, J. Am. Chem. Soc. 1977, 99, 4860-4862.
11. J. J. McKinnon, A. S. Mitchell, M. A. Spackman, Chem. Eur. J. 1998, 4, 2136-2141
12. L. Lo Presti, R. Soave, M. Longhi, E. Ortoleva, Acta Crystallogr. Sect. B 2010, 66, 527-543.
13. A. R. Oganov, Modern Methods of Crystal Structure Predictions, Wiley-VCH, Weinhem, 2011.
14. I. G. Kaplan, Intermolecular Interactions: Physical Picture, Cumputational Methods and Model Potentials, Wiley, New York, 2006.
15. C. Gatti, R. Bianchi, R. Destro, F. Merati, J. Mol. Struct.: THEOCHEM 1992, 255, 409-433.
16. A. Volkov, Y. Abramov, P. Coppens, C. Gatti, Acta Crystallogr. Sect. A 2000, 56, 332-339.
17. B. Engels, T. C. Schmidt, C. Gatti, T. Schirmeister, R. F. Fink, Structure & Bonding 2012, 147, 47-98.
18. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 1998, 285, 170-173.
19. E. Espinosa, M. Souhassou, K. Lachekar, C. Lecomte, Acta Crystallogr. Sect. B 1999, 55, 563-572.
20. C. Gatti, E. May, R. Destro, F. Cargnoni, J. Phys. Chem. A 2002, 106, 2707-2720.
21. Q. Zhao, D. Feng, Y. Sun, J. Hao, Z. Cai, Int. J. Quantum Chem. 2011, 111, 3881-3887.
22. M. Palusiak, T. M. Krygowski, Chem. Phys. Lett. 2009, 481, 34-38.
23. Y. V. Nelyubina, K. A. Lyssenko, R. G. Kostyanovsky, D. A. Bakulin, M. Yu. Antipin, Mendeleev Commun. 2008, 18, 29-31.
24. Y. V. Nelyubina, I. V. Glukhov, M. Yu. Antipin, K. A. Lyssenko, Chem. Commun. 2010, 46, 3469-3471.
25. L. Lo Presti, A. Ellern, R. Destro, B. Lunelli, J. Phys. Chem. A 2009, 113, 3186-3196.
26. R. F. W. Bader, Atoms In Molecules: A Quantum Theory, Clarendon Press, Oxford, 1990.
27. T. S. Koritsanszky, P. Coppens, Chem. Rev. 2001, 101, 1583-1627.
28. C. Gatti, Z. Kristallogr. 2005, 220, 399-457.
29. L. J. Farrugia, C. Evans, M. Tegel, J. Phys. Chem. A 2006, 110, 7952-7961.
30. A. M. Pendás, E. Francisco, M. A. Blanco, C. Gatti, Chem. Eur. J. 2007, 13, 9362-9371.
31. R. Ponec, C. Gatti, Inorg. Chem. 2009, 48, 11024-11031.
32. R. F. W. Bader, C. Gatti, Chem. Phys Lett. 1998, 287, 233-238.
33. C. Gatti, Structure & Bonding 2012, 147, 193-285.
34. X. Fradera, M. A. Austen, R. F. W. Bader, J. Phys. Chem. A 1999, 103, 304-314.
35. E. R. Johnson, S. Keinan, P. Mori-Sanchez, J. Contreras-Garcia, A. J. Cohen, W. Yang, J. Am. Chem. Soc. 2010, 132, 6498-6506.
36. J. Contreras-García, W. J. Yang, E. R. Johnson, J. Phys. Chem. A 2011, 115, 12983-12990.
37. H.-S. Bürgi, S. C. Capelli, A. E. Goeta, J. A. K. Howard, M. A. Spackman, D. S. Yufit, Chem. Eur. J. 2002, 8, 3512-3521.
38. L. Lo Presti, R. Soave, R. Destro, J. Phys. Chem. B 2006, 110, 6405-6514.
39. J. Overgaard, D. E. Hibbs, Acta Crystallogr. Sect. A 2004, 60, 480-487.
40. A. Zupan, J. P. Perdew, K. Burke, M. Causà , Int. J. Quantum Chem. 1997, 61, 835-845.
41. A. Zupan, K. Burke, M. Ernzerhof, J. P. Perdew, J. Chem. Phys. 1997, 106, 10184-10193.
42. A. D. Becke, in Modern Electronic Structure Theory (Ed.:, D. R. Yarkony,), World Scientific, River Edge, 1995, pp. 1022-1046.
43. G. Saleh, C. Gatti, L. Lo Presti, unpublished results.
44. N. K. Hansen, P. Coppens, Acta Crystallogr. Sect. A 1978, 34, 909-921.
45. A. Volkov, P. Macchi, L. J. Farrugia, C. Gatti, P. Mallinson, T. Richter, T. Koritsanszky, XD2006-A Computer Program Package for Multipole Refinement, Topological Analysis of Charge Densities and Evaluation of Intermolecular Energies from Experimental and Theoretical Structure Factors, 2006. See also http://xd.chem.buffalo.edu/.
46. G. Saleh, C. Gatti, L. Lo Presti, Comput. Theor. Chem. 2012, in press, DOI:.
47. L. Lo Presti, R. Soave, R. Destro, Acta Crystallogr. Sect. C 2003, 59, o 199 -o 201.
48. C. Pratt Brock, Acta Crystallogr. Sect. B 2002, 58, 1025-1031.
49. U. Koch, P. L. A. Popelier, J. Phys. Chem. 1995, 99, 9747-9754.
50. J. F. Dobson, K. McLennan, A. Rubio, J. Wang, T. Gould, H. M. Lee, B. P. Dinte, Aust. J. Chem. 2001, 54, 513-527.
51. B. Civalleri, C. M. Zicovich-Wilson, L. Valenzano, P. Ugliengo, CrystEngComm 2008, 10, 405-410.
52. D. S. Sholl, J. A. Steckel, Density Functional Theory: A Practical Introduction, Wiley, New York, 2009, p. 29.
53. See ref. [5], Chapter 12, and references therein.
54. M. J. Allen, D. Tozer, J. Chem. Phys. 2002, 117, 11113-11120.
55. R. F. W. Bader, J. Phys. Chem. A 2009, 113, 10391-10396.
56. R. F. W. Bader, J. Phys. Chem. A 2010, 114, 7431-7444.
57. G. R. Desiraju, A. Gavezzotti, Acta Crystallogr. Sect. B 1989, 45, 473-482.
58. M. Nishio, Phys. Chem. Chem. Phys. 2011, 13, 13873-13900.
59. B. Hegedüs, P. Bod, K. Harsanyi, I. Peter, A. Kalman, L. Parkanyi, J. Pharm. Biomed. Anal. 1989, 7, 563-569.
60. G. Gilli, P. Gilli, J. Mol. Struct. 2000, 552, 1-12.
61. A. Savin, B. Silvi, F. Colonna, Can. J. Chem. 1996, 74, 1088-1096
62. M. Calatayud, J. Andrés, A. Beltrán, B. Silvi, Theor. Chem. Acc. 2001, 105, 299-308.
63. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1987, S 1 -S 19.
64. R. Destro, R. Soave, M. Barzaghi, L. Lo Presti, Chem. Eur. J. 2005, 11, 4621-4634.
65. T. A. Keith, R. F. W. Bader, Y. Aray, Int. J. Quantum Chem. 1996, 57, 183-198.
66. F. H. Allen, I. J. Bruno, Acta Crystallogr. Sect. B 2010, 66, 380-386.
67. A. Ostergaard Madsen, J. Appl. Crystallogr. 2006, 39, 757-758
68. R. Dovesi, V. R. Saunders, C. Roetti, R. Orlando, C. M. Zicovich-Wilson, F. Pascale, B. Civalleri, K. Doll, N. M. Harrison, I. J. Bush, P. D'Arco, M. Llunell, CRYSTAL06 User's Manual, University of Torino, Torino, Italy, 2006.
69. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
70. R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650-654.
71. C. Gatti, TOPOND98, An Electron Density Topological Program For System Periodic In N (N=0-3)dimensions, User's Manual, CNR-ISTM, Milano, Italy, 1999.
72. C. Gatti, V. R. Saunders, C. Roetti, J. Chem. Phys. 1994, 101, 10686-10696.
73. C. B. Hübschle, P. Luger, J. Appl. Crystallogr. 2006, 39, 901-904.