Halogen bonding in 2,5-dichloro-1,4-benzoquinone: Insights from experimental and theoretical charge density analysis

Crystal Growth and Design

Volumn 11, Issue 5, 2011, Pages 1855-1862

  Hathwar, Venkatesha R ^a   Gonnade, Rajesh G ^b   Munshi, Parthapratim ^c   Bhadbhade, Mohan M ^b,d   Row, Tayur N Guru ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

^c Nancy University CNRS   (France)

^d UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BOND CRITICAL POINTS; CHARGE-DENSITY ANALYSIS; CRYSTALLINE LATTICE; DENSITY FEATURES; ELECTROSTATIC POTENTIALS; EXPERIMENTAL CHARGE DENSITY; HALOGEN BONDING; HALOGEN BONDS; HIGH RESOLUTION X RAY DIFFRACTION; ISO SURFACE; QUANTUM CALCULATION; STATIC DEFORMATIONS;

CHARGE DENSITY; MOLECULAR CRYSTALS; SURFACE ANALYSIS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

CHLORINE;

EID: 79957956369     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg2000415     Document Type: Article

References (112)

1. (a) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; Wiley-VCH: Weinheim, Germany, 1995.
2. (b) Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311-2327.
3. (c) Steiner, T. Angew. Chem. Int. Ed. 2002, 41, 48-76.
4. (d) Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342-8356.
5. (e) Nangia, A. J. Chem. Sci. 2010, 122, 295-310.
6. (a) Hamilton, W. C.; Ibers, J. A Hydrogen Bonding in Solids; Benjamin: New York, 1968.
7. (b) Desiraju, G. R Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
8. (c) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer: Berlin, 1991.
9. (d) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, U. K., 1997.
10. (e) Scheiner, S. Hydrogen Bonding. A Theoretical Perspective; Oxford University Press: Oxford, U. K., 1997.
11. (f) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, U. K, 1999.
12. (g) Desiraju, G. R Angew. Chem. Int. Ed. 2010, 49, 2-10.
13. (a) Legon, A. C. Angew. Chem., Int. Ed. 1999, 38, 2686-2714.
14. (b) Halogen Bonding: Fundamentals and Applications; Metrangolo, P., Resnati, G, Eds.; Springer: Berlin, 2008.
15. (c) Legon, A. C. Phys. Chem. Chem. Phys. 2010, 12, 7736-7747.
16. Legon, A. C. In Halogen Bonding: Fundamentals and Applications; Metrangolo, P., Resnati, G, Eds.; Springer: Berlin, 2008; pp 17-64.
17. Bosch, E.; Barnes, C. L. Cryst. Growth Des. 2002, 2, 299-302.
18. (a) Rosenfield, RE.; Parthasarathy, R.; Dunitz, J. D. J. Am. Chem. Soc. 1977, 99, 4860-4862.
19. (b) Row, T. N. G.; Parthasarathy, R. J. Am. Chem. Soc. 1981, 103, 477-479.
20. (c) Ramasubbu, N.; Parthasarathy, R.; Murray-Rust, P. J. Am. Chem. Soc. 1986, 108, 4308-4314.
21. (a) Hassel, O.; Rømming, C. Quart. Rev. (London) 1962, 16, 1-18.
22. (b) Hassel, O Science 1970, 170, 497-502.
23. (a) Sarma, J. A. R. P.; Allen, F. H.; Hoy, V. J.; Howard, J. A. K.; Thaimattam, R.; Biradha, K.; Desiraju, G. R Chem. Commun. 1997, 101-102.
24. (b) Bond, A. D.; Griffiths, J.; Rawson, J. M.; Hulliger, J. Chem. Commun. 2001, 2488-2489.
25. (c) Thallapally, P. K.; Desiraju, G. R.; Bagieu-Beucher, M.; Masse, R.; Bourgogne, C.; Nicoud, J. F. Chem. Commun. 2002, 1052-1053.
26. (d) George, S.; Nangia, A.; Lam, C.-K; Mak, T. C. W.; Nicoud, J.-F. Chem. Commun. 2004, 1202-1203.
27. (e) Metrangolo, P.; Resnati, G.; Meyer, F.; Pilati, T.; Liantonio, R.; Meyer, F. J. Polym. Sci, Part A: Polym. Chem. 2007, 45, 1-15 and references therein..
28. Metrangolo, P.; Resnati, G. Chem.-Eur. J. 2001, 7, 2511-2519.
29. (b) Gonnade, R. G.; Shashidhar, M. S.; Bhadbhade, M. M. J. Indian Inst. Sci. 2007, 87, 149-165.
30. (c) Metrangolo, P.; Meyer, F.; Pilati, T.; Resnati, G.; Terraneo, G. Angew. Chem. Int. Ed. 2008, 47, 6114-6127.
31. (d) Cavallo, G.; Metrangolo, P.; Pilati, T.; Resnati, G.; Sansotera, M.; Terraneo, G Chem. Soc. Rev. 2010, 39, 3772-3783.
32. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Natl. Acad Sci. USA. 2004, 101, 16789-16794 and references therein.
33. (b) Voth, A. R.; Hays, F. A.; Ho, P. S. Proc. Natl. Acad Sci. U. SA. 2007, 104, 1688-6193.
34. (c) Tawarada, R.; Seio, K.; Sekine, M. J. Org. Chem. 2008, 73, 383-390.
35. Sureshan, K. M.; Gonnade, R. G.; Puranik, V. G.; Bhadbhade, M. M.; Shashidhar, M. S. Chem. Commun. 2001, 881-882.
36. (b) Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G J. Am. Chem. Soc 2004, 126, 4500-4501.
37. (c) Gonnade, R. G.; Bhadbhade, M. M.; Shashidhar, M. S.; Sanki, A. K. Chem. Commun. 2005, 5870-5872.
38. (d) Saha, B. K.; Nangia, A.; Jaskolski, M. CrystEngComm. 2005, 7, 355-358.
39. (e) Aakeroy, C. B.; Fasulo, M.; Schultheiss, N.; Desper, J.; Moore, C. J. Am. Chem. Soc. 2007, 129, 13772-13773.
40. (f) Gonnade, R. G.; Bhadbhade, M. M.; Shashidhar, M. S. CrystEngComm. 2008, 10, 288-296.
41. (a) Farina, A.; Meille, S. V.; Messina, M. T.; Metrangolo, P.; Resnati, G.; Vecchio, G Angew. Chem. Int. Ed. 1999, 38, 2433-2436.
42. (b) Takeuchi, T.; Minato, Y.; Masayoshi, M.; Shinmori, H. Tetrahedron Lett. 2005, 46, 9025-9027.
43. Jiang, Y.; Alcaraz, A. A.; Chen, J. M.; Kobayashi, H.; Lu, Y. J.; Snyder, J. P. J. Med. Chem. 2006, 49, 1891-1899.
44. (a) Bertani, R.; Metrangolo, P.; Moiana, A.; Perez, E.; Pilati, T.; Resnati, G.; Rico-Lattes, I.; Sassi, A Adv. Mater. 2002, 14, 1197-1201.
45. (b) Xu, J.; Liu, X.; Lin, T.; Huang, J.; He, C. Macromolecules 2005, 38, 3554-3557.
46. (c) Metrangolo, P.; Prasang, C.; Resnati, G.; Liantonio, R.; Whitwood, A. C.; Bruce, D. W. Chem. Commun. 2006, 3290-3292.
47. (a) Metrangolo, P.; Meyer, F.; Pilati, T.; Proserpio, D. M.; Resnati, G Cryst. Growth Des. 2008, 8, 654-659.
48. (b) Raatikainen, K.; Rissanen, K CrystEngComm. 2009, 11, 750-752.
49. (a) Imakubo, T.; Sawa, H.; Kato, R. Synth. Met. 1995, 73, 117-122.
50. (b) Fourmigue, M.; Batail, P. Chem. Rev. 2004, 104, 5379-5418.
51. (c) Yamamoto, H. M.; Kosaka, Y.; Maeda, R.; Tamura, J.; Nakao, A.; Nakamura, T.; Kato, R ACS Nano 2008, 2, 143-155.
52. (a) Coppens, P. X-ray Charge Densities and Chemical Bonding; Oxford University Press: Oxford, U. K., 1997.
53. (b) Koritsanszky, T. S.; Coppens, P. Chem. Rev. 2001, 101, 1583-1621.
54. (a) Bader, R. F. W. Atoms in Molecules-A Quantum Theory; Clarendon: Oxford, U. K., 1990.
55. (b) Bader, R. F. W. J. Phys. Chem. A 1998, 102, 7314-7323.
56. (a) Duarte, D. J. R.; De Las Vallejos, M. M.; Peruchena, N. M. J. Mol. Model. 2010, 16, 737-748.
57. (b) Amezaga, N. J. M.; Pamies, S. C.; Peruchena, N. M.; Sosa, G. L. J. Phys. Chem. A 2010, 114, 552-562.
58. (a) Cody, V.; Murray-Rust, P. J. Mol. Struct. 1984, 112, 189-199.
59. (b) Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108-3116.
60. (c) Brammer, L.; Bruton, E. A.; Sherwood, P. Cryst. Growth Des. 2001, 1, 277-290.
61. (d) Ouvrard, C.; Le Questel, J. Y.; Berthelot, M.; Laurence, C. Acta Crystallogr., Sect. B 2003, 59, 512-526.
62. (e) Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G Acc. Chem. Res. 2005, 38, 386-395.
63. (f) Rssanen, K. CrystEngComm. 2008, 10, 1107-1113.
64. (a) Hathwar, V. R.; Row, T. N. G J. Phys. Chem. A 2010, 114, 13434-13441.
65. (b) Hathwar, V. R.; Row, T. N. G Cryst. Growth Des. 2011, DOI: 10.1021/cg1015862.
66. Bui, T. T. T.; Dahaoui, S.; Lecomte, C.; Desiraju, G. R.; Espinosa, E. Angew. Chem. Int. Ed. 2009, 48, 3838-3841.
67. (a) Bianchi, R.; Forni, A.; Pilati, T. Chem.-Eur. J. 2003, 9, 1631-1638.
68. (b) Bianchi, R.; Forni, A.; Pilati, T. Acta Crystallogr., Sect. B 2004, 60, 559-568.
69. Forni, A. J. Phys. Chem. A 2009, 113, 3403-3412.
70. Eskandari, K.; Zariny, H. Chem. Phys. Lett. 2010, 492, 9-13.
71. Bruker APEX2 (Version 1.0.22), BIS (Version 1.2.08), COSMO (Version 1.48), and SAINT (Version 7.06A); Bruker AXS Inc.:Madison, WI, 2006.
72. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426.
73. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122.
74. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
75. Volkov, A.; Macchi, P.; Farrugia, L. J.; Gatti, C.; Mallinson, P. R.; Richter, T.; Koritsanszky, T. S. XD2006, Rev. 5.34; University at Buffalo, State University of New York: Buffalo, NY, 2006.
76. Hansen, N. K.; Coppens, P. Acta Crystallogr., Sect. A 1978, 34, 909-921.
77. Allen, F. H. Acta Crystallogr., Sect. B 1986, 42, 515-522.
78. (a) Sorensen, H. O.; Stewart, R. F.; McIntyre, G. J.; Larsen, S. Acta Crystallogr., Sect. A 2003, 59, 540-550.
79. (b) Munshi, P.; Cameron, E.; Row, T. N. G.; Ferrara, J. D.; Cameron, T. S. J. Phys. Chem. A 2007, 111, 7888-7897.
80. (a) Madsen, A. Ø. J. Appl. Crystallogr. 2006, 39, 757-758.
81. (b) Munshi, P.; Madsen, A. Ø.; Spackman, M. A.; Larsen, S.; Destro, R. Acta Crystallogr., Sect. A 2008, 64, 465-475.
82. Dovesi, R.; Saunders, V. R.; Roetti, C.; Orlando, R.; Zicovich-Wilson, C. M.; Pascale, F.; Civalleri, B.; Doll, K.; Harrison, N. M.; Bush, I. J.; D'Arco, Ph.; Llunell, M. CRYSTAL06 User's Manual; University of Torino: Torino, Italy, 2006.
83. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
84. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
85. Rees, P. B. Acta Crystallogr., Sect. B 1970, 26, 1304-1311.
86. (a) McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr., Sect. B 2004, 60, 627-668.
87. (b) Spackman, M. A.; McKinnon, J. J. CrystEngComm 2002, 4, 378-392.
88. Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer 2.0; University of Western Australia: Perth, Australia, 2007 (http://hirshfeldsurface.net/CrystalExplorer).
89. (a) McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Chem. Commun. 2007, 3814-3816.
90. (b) Munshi, P.; Skelton, W.; McKinnon, J. J.; Spackman, M. A. CrystEngComm 2008, 10, 197-206.
91. (c) Munshi, P.; Jelsch, C.; Hathwar, V. R.; Row, T. N. G. Cryst. Growth Des. 2010, 10, 1516-1526.
92. Hirshfeld, F. L. Acta Crystallogr., Sect. A 1976, 32, 239-244.
93. (a) Abramov, Y. A. Acta Crystallogr., Sect. A 1997, 53, 264-272.
94. (b) Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173.
95. (c) Espinosa, E.; Alkorta, I.; Elguero, J.; Molins, E. J. Chem. Phys. 2002, 117, 5529-5542.
96. (a) Abramov, Y.; Volkov, A.; Wu, G.; Coppens, P. Acta Crystallogr., Sect. A 2000, 56, 585-591.
97. (b) Abramov, Y.; Volkov, A.; Wu, G.; Coppens, P. J. Phys. Chem. B 2000, 104, 2183-2188.
98. (a) Cox, S. R.; Hsu, L. Y.; Williams, D. E. Acta Crystallogr., Sect. A 1981, 37, 293-301.
99. (b) Williams, D. E.; Cox, S. R. Acta Crystallogr., Sect. B 1984, 40, 404-417.
100. (a) Presti, L. L.; Destro, R. J. Chem. Phys. 2008, 128, 044710-044718.
101. (b) de Vries, R. Y.; Feil, D.; Tsirelson, V. G. Acta Crystallogr., Sect. B 2000, 56, 118-123.
102. (c) Bytheway, I.; Chandler, G. S.; Figgis, B. N. Acta Crystallogr., Sect. A 2002, 58, 451-459.
103. (d) Volkov, A.; Abramov, Y.; Coppens, P.; Gatti, C. Acta Crystallogr., Sect. A 2000, 56, 332-339.
104. (e) Coppens, P.; Volkov, A. Acta Crystallogr., Sect. A 2004, 60, 357-364.
105. Hubschle, C. B.; Luger, P. J. Appl. Crystallogr. 2006, 39, 901-904.
106. (a) Politzer, P.; Lane, P.; Concha, M. C.; Ma, Y.; Murray, J. S. J. Mol. Model. 2007, 13, 305-311.
107. (b) Murray, J. S.; Lane, P.; Clark, T.; Politzer, P. J. Mol. Model. 2007, 13, 1033-1038.
108. (c) Clark, T.; Hennemann, M.; Murray, J, S.; Politzer, P. J. Mol. Model. 2007, 13, 291-296.
109. (d) Murray, J. S.; Lane, P.; Politzer, P. Int. J. Quantum Chem. 2007, 107, 2286-2292.
110. (e) Murray, J. S.; Concha, M. C.; Lane, P.; Hobza, P.; Politzer, P. J. Mol. Model. 2008, 14, 699-704.
111. (f) Politzer, P.; Murray, J. S.; Concha, M. C. J. Mol. Model. 2008, 14, 659-665.
112. Riley, K. E.; Hobza, P. J. Chem. Theory Comput. 2008, 4, 232-242.