Noncovalent interactions in crystalline picolinic acid N-oxide: Insights from experimental and theoretical charge density analysis

Crystal Growth and Design

Volumn 13, Issue 2, 2013, Pages 816-828

  Shishkina, Anastasia V ^a   Zhurov, Vladimir V ^b   Stash, Adam I ^a,c   Vener, Mikhail V ^a   Pinkerton, A Alan ^b   Tsirelson, Vladimir G ^a  

^a MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

^b UNIVERSITY OF TOLEDO   (United States)

^c KARPOV INSTITUTE OF PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CRITICAL POINTS; CHARGE DENSITY DISTRIBUTIONS; CHARGE-DENSITY ANALYSIS; DISPERSION CORRECTION; ELECTROSTATIC POTENTIALS; EMPIRICAL CORRELATIONS; EXPERIMENTAL CHARGE DENSITY; GRADIENT FIELDS; INTERMOLECULAR INTERACTION ENERGIES; LATTICE ENERGIES; NON-COVALENT INTERACTION; PICOLINIC ACID N-OXIDE; QUANTUM CALCULATION; REASONABLE VALUE; STACKING INTERACTION; THEORETICAL STUDY;

CHARGE DENSITY; DISPERSIONS; HYDROGEN BONDS; INFORMATION THEORY;

DENSITY FUNCTIONAL THEORY;

EID: 84873391952     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg3015223     Document Type: Article

References (141)

1. Buckingham, A. D. In Crystal Engineering: The Design and Application of Functional Solids; Seddon, K. R., Zaworotko, M., Eds. NATO Science Series C, Vol. 539; Kluwer Academic: Boston, 1999; pp 49-68.
2. Fogassy, E.; Nogradi, M.; Kozma, D.; Egri, G.; Palovics, E.; Kiss, V. Org. Biomol. Chem. 2006, 4, 3011-3030
3. Karamertzanis, P. G.; Anandamanoharan, P. R.; Fernandes, P.; Cains, P. W.; Vickers, M.; Tocher, D. A.; Florence, A. J.; Price, S. L. J. Phys. Chem. B 2007, 111, 5326-5336
4. Gourlay, M. D.; Kendrick, J.; Leusen, F. J. J. Cryst. Growth Des. 2007, 7, 56
5. Price, S. L. Adv. Drug Delivery Rev. 2004, 56, 301-309
6. Evans, O. R.; Lin, W. B. Acc. Chem. Res. 2002, 35, 511-522
7. Roesky, H. W.; Andruh, M. Coord. Chem. Rev. 2003, 236, 91-119
8. Kwon, O.-P.; Ruiz, B.; Choubye, A.; Mutter, L.; Schneider, A.; Jazbinesek, M.; Gramlich, V.; Gunter, P. Chem. Mater. 2006, 18, 4049-4054
9. Malaspina, L.; Gigli, R.; Bardi, G. J. Chem. Phys. 1973, 59, 387-394
10. Murata, S.; Sakiyama, M.; Seki, S. J. Chem. Thermodynamics 1982, 14, 707-721
11. Sabbah, R.; Antipine, I.; Coten, M.; Davy, L. Thermochim. Acta 1987, 115, 153-165
12. Holdiness, M. R. Thermochim. Acta 1983, 68, 375-377
13. Civalleri, B.; Zicovich-Wilson, C. M.; Valenzano, L.; Ugliengo, P. CrystEngComm 2008, 10, 405-410
14. Maschio, L.; Civalleri, B.; Ugliengo, P.; Gavezzotti, A. J. Phys. Chem. A 2011, 115, 11179-11186
15. Dominiak, P. M.; Espinosa, E.; Angyan, J. In Intermolecular Interactions Energies from Experimental Charge Density Studies from Charge Density Studies in Modern Charge Density Analysis; Gatti, C.; Macchi, P., Eds.; Springer: Heidelberg, London, NY, 2012; pp 387-433.
16. Civalleri, B.; Doll, K.; Zicovich-Wilson, C. M. J. Phys. Chem. B 2007, 111, 26-33
17. Ouvrard, C.; Mitchell, J. B. O. Acta Crystallogr. B 2003, 59, 676-685
18. Day, G. M. Crystallogr. Rev. 2011, 17, 3-52 and references therein
19. Pertsin, A. J.; Kitaigorodsky, A. I. The Atom-Atom Potential Method. Application to Organic Molecular Solids; Springer-Verlag: New York, 1987.
20. Price, S. L. Acc. Chem. Res. 2009, 42, 117-126
21. 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, 697-714
22. 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, 647-661
23. Dunitz, J. D.; Gavezzotti, A. Angew. Chem., Int. Ed. 2005, 44, 1766-1787
24. Sancho-García, J. C.; Olivier, Y. J. Chem. Phys. 2012, 137, 194311.
25. Dzyabchenko, A.; Scheraga, H. A. Acta Crystallogr., Sect. B 2004, 60, 228-237
26. Dunitz, J. D.; Gavezzotti, A. Chem. Soc. Rev. 2009, 38, 2622-2633
27. Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Oxford University Press: Oxford, 1990.
28. Tsirelson, V. G. In The Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design; Matta, C.; Boyd, R., Eds.; Wiley-VCH: New York, 2007; Chapter 10.
29. Nelyubina, Y. V.; Antipin, M. Yu.; Lyssenko, K. A. J. Phys. Chem. A 2007, 111, 1091-1095
30. Nelyubina, Y. V.; Antipin, M. Yu.; Cherepanov, I. A.; Lyssenko, K. A. CrystEngComm 2010, 12, 77-81
31. Vener, M. V.; Egorova, A. N.; Churakov, A. V; Tsirelson, V. G. J. Comput. Chem. 2012, 33, 2303-2309
32. Desiraju, G. R. Crystal Design: Structure and Function Perspectives in Supramolecular Chemistry; Desiraju, G. R., Ed.; Chichester: Wiley, 2003; Vol. 7.
33. Brock, C. P.; Dunitz, J. D. Chem. Mater. 1994, 6, 1118-1127
34. Sekhon, B. S. Ars Pharm. 2009, 50, 99-117
35. Price, S. L. Acc. Chem. Res. 2009, 42, 117-126
36. Berkovitch-Yellin, Z.; Leiserowitz, L. Acta Crystallogr., Sect. B 1984, 40, 159-165
37. Suponitsky, K. Y.; Tsirelson, V. G.; Feil, D. Acta Crystallogr., Sect. A 1999, 55, 821-827
38. Morrison, C. A.; Siddick, M. M. Chem.-Eur. J. 2003, 9, 628-634
39. Vishweshwar, P.; Babu, N. J.; Nangia, A.; Mason, S. A.; Puschmann, H.; Mondal, R.; Howard, J. A. K. J. Phys. Chem. A 2004, 108, 9406-9416
40. Schmidtmann, M.; Farrugia, L. J.; Middlemiss, D. S.; Gutmann, M. J.; McIntyre, G. J.; Wilson, C. C. J. Phys. Chem. A 2009, 113, 13985-13997
41. Dittrich, B.; Weber, M.; Kalinowski, R.; Grabowsky, S.; Hubschle, C. B.; Luger, P. Acta Crystallogr., Sect. B 2009, 65, 749-756
42. Hathwar, V. R.; Guru Row, T. N. Cryst. Growth Des. 2011, 11, 1338-1346
43. Hathwar, V. R.; Thakur, T. S.; Dubey, R.; Pavan, M. S.; Guru Row, T. N.; Desiraju, G. R. J. Phys. Chem. A 2011, 115, 12852-12863
44. Hathwar, V. R.; Gonnade, R. G.; Munshi, P.; Bhadbhade, M. M.; Guru Row, T. N. Cryst. Growth Des. 2011, 11, 1855-1862
45. Krawczuk, A.; Stadnicka, K. J. Phys. Chem. A 2012, 116, 9759-9768
46. Platts, J. A.; Howard, S. T. J. Chem. Phys. 1996, 105, 4668-4674
47. Vener, M. V.; Manaev, A. V.; Egorova, A. N.; Tsirelson, V. G. J. Phys. Chem. A 2007, 111, 1155-1162
48. Bertini, L.; Cargnoni, F.; Gatti, C. Theor. Chem. Acc. 2007, 117, 847-884
49. Gibbs, G. V.; Downs, R. T.; Cox, D. F.; Ross, N. L.; Boisen, M. B.; Rosso, K. M. J. Phys. Chem. A 2008, 112, 3693-3699
50. Presti, L. L.; Ellern, A.; Destro, R.; Lunelli, B. J. Phys. Chem. A 2009, 113, 3186-3196
51. Vener, M. V.; Egorova, A. N.; Tsirelson, V. G. Chem. Phys. Lett. 2010, 500, 272-276
52. Götz, K.; Meier, F.; Gatti, C.; Burow, A. M.; Sierka, M.; Sauer, J.; Kaupp, M. J. Comput. Chem. 2010, 31, 2568-2576
53. Churakov, A. V.; Prikhodchenko, P. V.; Lev, O.; Medvedev, A. G.; Tripol'skaya, T. A.; Vener, M. V. J. Chem. Phys. 2010, 133 (164506) 1-9
54. Shishkina, A. V.; Stash, A. I.; Civalleri, B.; Ellern, A.; Tsirelson, V. G. Mendeleev Commun. 2010, 20, 161-164
55. Vener, M. V.; Medvedev, A. G.; Churakov, A. V.; Prikhodchenko, P. V.; Tripol'skaya, T. A.; Lev, O. J. Phys. Chem. A 2011, 115, 13657-13663
56. Stare, J.; Mavri, J.; Ambrožić, G.; Hadži, D. J. Mol. Struct.(THEOCHEM) 2000, 500, 429-440
57. Stare, J.; Panek, J.; Eckert, J.; Grdadolnik, J.; Mavri, J.; Hadži, D. J. Phys. Chem. A 2008, 112, 1576-1586
58. Panek, J.; Stare, J.; Hadzi, D. J. Phys. Chem. A 2004, 108, 7417-7423
59. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
60. Von Lilienfeld, O. A.; Tkatchenko, A. J. Chem. Phys. 2010, 132 (234109) 1-11
61. Grimme, S.; Antony, J.; Schwabe, T.; Mück-Lichtenfeld, C. Org. Biomol. Chem. 2007, 5, 741-758
62. Karamertzanis, H. G.; Day, G. M.; Welch, G. W. A.; Kendrick, J.; Leusen, F. J. J.; Neumann, M. A.; Price, S. L. J. Chem. Phys. 2008, 128 (244708) 1-17
63. Matta, C. F.; Castillo, N.; Boyd, R. J. J. Phys. Chem. B 2006, 110, 563-578
64. Rutledge, L. R.; Wetmore, S. D. J. Chem. Theory Comput. 2008, 4, 1768-1780
65. Rutledge, L. R.; Campbell-Verduyn, L. S.; Hunter, K. C.; Wetmore, S. D. J. Phys. Chem. B 2006, 110, 19652-19663
66. Acosta-Silva, C.; Branchadell, V.; Bertran, J.; Oliva, A. J. Phys. Chem. B 2010, 114, 10217-10227
67. González Moa, M. J.; Mandado, M.; Mosquera, R. A. J. Phys. Chem. A 2007, 111, 1998-2001
68. Kamya, P. R. N.; Muchall, H. M. J. Phys. Chem. A 2011, 115, 12800-12808
69. Estévez, L.; Otero, N.; Mosquera, R. A. J. Phys. Chem. A 2009, 113, 11051-11058
70. Rutledge, L. R.; Navarro-Whyte, L.; Peterson, T. L.; Wetmore, S. D. J. Phys. Chem. A 2011, 115, 12646-12658
71. Shishkin, O. V.; Dyakonenko, V. V.; Maleev, A. V.; Schollmeyer, D.; Vysotsky, M. O. CrystEngComm 2011, 13, 800-805
72. Dyakonenko, V. V.; Maleev, A. V.; Zbruyev, A. I.; Chebanov, V. A.; Desenko, S. M.; Shishkin, O. V. CrystEngComm 2010, 12, 1816-1823
73. Sarma, R. J.; Tamuly, C.; Barooah, N.; Baruah, J. B. J. Mol. Struct. 2007, 829, 29-36
74. Reger, D. L.; Debreczeni, A.; Horger, J. J.; Smith, M. D. Cryst. Growth Des. 2011, 11, 4068-4079
75. Wilsona, C. R.; Munroa, O. Q. Acta Crystallogr., Sect. C 2010, 66, o513-o516
76. Konovalova, I. S.; Nelyubina, Y. V.; Lyssenko, K. A.; Paponov, B. V.; Shishkin, O. V. J. Phys. Chem. A 2011, 115, 8550-8562
77. Morokuma, K. J. Chem. Phys. 1971, 55, 1236
78. Kitaura, K.; Morokuma, K. Int. J. Quantum Chem. 1976, 10, 325
79. Chałasinski, G.; Szczesniak, M. Chem. Rev. 1994, 94, 1723
80. Sokalski, W. A.; Roszak, S.; Pecul, K. Chem. Phys. Lett. 1988, 153, 153
81. Cybulski, S. M.; Chałasinski, G.; Moszynski, R. J. Chem. Phys. 1990, 92, 4357
82. Szalewicz, K. WIREs Comput. Mol. Sci. 2012, 2, 254-272
83. Cybulski, H.; Sadlej, J. J. Chem. Theory Comput. 2008, 4, 892-897
84. Jeziorski, B.; Moszyn.ski, R.; Szalewicz, K. Chem. Rev. 1994, 94, 1887
85. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173
86. Espinosa, E.; Alkorta, I.; Rozas, I.; Elguero, J.; Molins, E. Chem. Phys. Lets. 2001, 336, 457-464
87. Mata, I.; Alkorta, I.; Espinosa, E.; Molins, E. Chem. Phys. Lett. 2011, 507, 185-189
88. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326
89. Zhurova, E. A.; Zhurov, V. V.; Tanaka, K. Acta Crystallogr., Sect. B 1999, 55, 917-922
90. Zhurov, V. V.; Zhurova, E. A.; Pinkerton, A. A. J. Appl. Crystallogr. 2008, 41, 340-349
91. Blessing, R. H. Acta Crystallogr., Sect. A 1995, 51, 33-38
92. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426
93. Sheldrick, G. M. SHELXS97; University of Gottingen: Germany, 1997.
94. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122
95. Hansen, N. K.; Coppens, P. Acta Crystallogr., Sect. A 1978, 34, 909-921
96. Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P.; Richter, T.; Koritsanszky, T. XD2006, Rev. 5.34; University at Buffalo, State University of New York: Buffalo, NY, 2006.
97. Kirzhnits, D. A. Sov. Phys. JETP 1957, 5, 64-72
98. Abramov, Yu. A. Acta Crystallogr., Sect. A 1997, 53, 264-272
99. Tsirelson, V. G. Acta Crystallogr., Sect. B 2002, 58, 632-639
100. Stash, A. I.; Tsirelson, V. G. J. Appl. Crystallogr. 2002, 35, 371-373
101. Stash, A. I.; Tsirelson, V. G. Crystallogr. Rep. 2005, 50, 177-184
102. Dovesi, R.; Saunders, V. R.; Roetti, R.; Orlando, R.; Zicovich-Wilson, C. M.; Pascale, F.; Civalleri, B.; Doll, K.; Harrison, N. M.; Bush, I. J.; D'Arco, P.; Llunell, M. CRYSTAL09 (CRYSTAL09 User's Manual); University of Torino: Torino, 2009.
103. Vener, M. V.; Sauer, J. Phys. Chem. Chem. Phys. 2005, 7, 258-263
104. Zicovich-Wilson, C. M.; San-Román, M. L.; Camblor, M. A.; Pascale, F.; Durand-Niconoff, J. S. J. Am. Chem. Soc. 2007, 129, 11512-11523
105. Jezierska, A.; Panek, J. J.; Koll, A.; Mavri, J. J. Chem. Phys. 2007, 126 (205101) 1-9
106. Vener, M. V.; Manaev, A. V.; Tsirelson, V. G. J. Phys. Chem. A 2008, 112, 13628-13632
107. Jezierska-Mazzarello, A.; Vuilleumier, R.; Panek, J. J.; Ciccotti, G. J. Phys. Chem. B 2010, 114, 242-253
108. Rozenberg, M.; Loewenschuss, A.; Marcus, Y. Phys. Chem. Chem. Phys. 2000, 2, 2699-2702
109. Rozenberg, M.; Shoham, G.; Reva, I.; Fausto, R. Phys. Chem. Chem. Phys. 2005, 7, 2376-2383
110. Musin, R. N.; Mariam, Y. H. J. Phys. Org. Chem. 2006, 19, 425-444
111. Iogansen, A. V. Spectrochim. Acta. A 1999, 55, 1585-1612
112. Filarowski, A.; Koll, A.; Sobczyk, L. Curr. Org. Chem 2009, 13, 172-193
113. Mohammadzadeh Jahani, P.; Nowroozi, A.; Hajiabadi, H.; Hassani, M. Struct. Chem. 2012, 23, 1941-1951
114. Lyssenko, K. A. Mendeleev Commun. 2012, 22, 1-7
115. Borissova, A. O.; Korlyukov, A. A.; Antipin, M. Y.; Lyssenko, K. A. J. Phys. Chem. A 2008, 112, 11519-11522
116. Nelyubina, Yu. V.; Antipin, M. Yu.; Lyssenko, K. A. Usp. Khim. 2010, 79, 195-217
117. Sarma, J. A. R. P.; Desiraju, G. R. Acc. Chem. Res. 1986, 19, 222-228
118. Steiner, T. M.; Schreurs, A. M.; Lutz, M.; Kroon, J. Acta Crystallogr., Sect. C 2000, 56, 577-579
119. Gatti, C.; May, E.; Destro, R.; Cargnoni, F. J. Phys. Chem. A 2002, 106, 2707-2720
120. Tsirelson, V. G.; Ozerov, R. P. Electron Density and Bonding in Crystals; Institute of Physics Publishing: Bristol, England/Philadelphia, 1996.
121. Khinchin, A. I. Mathematical Foundations of Information Theory; Dover: New York, 1957.
122. Ash, R. Information Theory; Interscience Publishers: New York, 1965.
123. Shannon, C. E. Bell System Techn. J. 1948, 27, 379-423
124. Nalewajski, R. F. Information Theory of Molecular Systems; Elsevier: Amsterdam, 2006.
125. Nalewajski, R. F. Information Origins of the Chemical Bond; Nova Science Publishers: New York, 2010.
126. Ihara, S. Information Theory for Continuous Systems; World Scientific Publishing: Singapore, 1993.
127. Tsirelson, V.; Nagy, A. J. Phys. Chem. A 2009, 113, 9022-9029
128. Nguyen, T. H.; Groundwater, P. W.; Platts, J. A.; Hibbs, D. E. J. Phys. Chem. A 2012, 116, 3420-3427
129. Hoser, A. A.; Jarzembska, K. N.; Dobrzycki, L.; Gutmann, M. J.; Wozniak, K. Cryst. Growth Des. 2012, 12, 3526-3539
130. Fedorov, I. A.; Zhuravlev, Y. N.; Berveno, V. P. Phys. Chem. Chem. Phys. 2011, 13, 5679-5686
131. King, M. D.; Blanton, T. N.; Korter, T. M. Phys. Chem. Chem. Phys. 2012, 14, 1113-1116
132. Bucko, T.; Hafner, J.; Lebegue, S.; Angyan, J. G. J. Phys. Chem. A 2010, 114, 11814-11824
133. Tsirelson, V.; Avilov, A.; Lepeshov, G.; Kulygin, A.; Stahn, J.; Pietsch, U.; Spence, J. C. H. J. Phys. Chem. B 2001, 105, 5068-5074
134. Tsirelson, V. G.; Shishkina, A. V.; Stash, A. I.; Parsons, S. Acta Crystallogr., Sect. B 2009, 65, 647-658
135. Mata, I.; Alkorta, I.; Molins, E.; Espinosa, E. ChemPhysChem 2012, 13, 1421-1424
136. Chickos, J. S.; Acree, W. E. J. Phys. Chem. Ref. Data 2002, 31, 537-698
137. Wendler, K.; Thar, J.; Zahn, S.; Kirchner, B. J. Phys. Chem. A 2010, 114, 9529-9536
138. Guin, M.; Patwari, G. N.; Karthikeyanb, S.; Kim, K. S. Phys. Chem. Chem. Phys. 2011, 13, 5514-5525
139. Pandey, R.; Mukhopadhyay, S.; Ramasesha, S.; Das, P. K J. Phys. Chem. B 2011, 115, 13842-13846
140. Hoepfner, V.; Deringer, V. L.; Dronskowski, R. J. Phys. Chem. A 2012, 116, 4551-4559
141. Dobado, J. A.; Molina, J.; Portal, D. J. Phys. Chem. A 1998, 102, 778-784