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Halogen Bonding pp 105–136Cite as

Halogen Bonding in Crystal Engineering

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Part of the book series: Structure and Bonding ((STRUCTURE,volume 126))

Abstract

The term halogen bonding encompasses any non-covalent interaction involving halogens as electrophilic species. High strength and directionality are the remarkable features of halogen bonding that fully justify its use as a primary intermolecular interaction to dictate molecular self-assembly processes. This chapter will outline the use of halogen bonding in crystal engineering and will highlight the obtainment of heteromeric crystal structures with complex topologies. Even though the use of halogen bonding is still in its infancy, the growing interest in the field shown by the crystal engineering community promises major advances in the future.

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References

  1. Lehn JM (1988) Angew Chem Int Ed 27:89

    Google Scholar 

  2. Braga D (2003) Chem Commun 22:2751

    Google Scholar 

  3. Metrangolo P, Resnati G (2001) Chem Eur J 7:2511

    CAS  Google Scholar 

  4. Metrangolo P, Pilati T, Resnati G, Stevenazzi A (2003) Curr Opin Colloid Interface Sci 8:215

    CAS  Google Scholar 

  5. Metrangolo P, Resnati G, Pilati T, Liantonio R, Meyer F (2007) J Polym Sci Part A Polym Chem 45:1

    CAS  Google Scholar 

  6. Fox BD, Liantonio R, Metrangolo P, Pilati T, Resnati G (2004) J Fluor Chem 125:271

    CAS  Google Scholar 

  7. Messina MT, Metrangolo P, Resnati G (2000) Resolution of racemic perfluorocarbons through self-assembly driven by donor–acceptor intermolecular recognition. In: Ramachandran PV (ed) Asymmetric fluoro-organic chemistry: synthesis, applications, and future directions. ACS symposium series 746. American Chemical Society, Washington DC, p 239

    Google Scholar 

  8. Metrangolo P, Pilati T, Resnati G (2004) Self-assembly of hybrid fluorous materials. In: Gladysz JA, Curran DP, Horwath IT (eds) Handbook of fluorous chemistry. Wiley, Weinheim, p 507

    Google Scholar 

  9. Metrangolo P, Neukirch H, Pilati T, Resnati G (2005) Acc Chem Res 38:386

    CAS  Google Scholar 

  10. Metrangolo P, Resnati G (2004) Halogen bonding. In: Atwood JL, Steed JW (eds) Encyclopedia of supramolecular chemistry. Dekker, New York, pp 628–635

    Google Scholar 

  11. Alkorta I, Rozas I, Elguero J (1998) J Phys Chem A 102:9278

    CAS  Google Scholar 

  12. Karpfen A (2003) Theor Chem Acc 110:1

    CAS  Google Scholar 

  13. Syssa-Magalé JL, Boubekeur K, Palvadeau P, Meerschaut A, Schöllhorn B (2005) Cryst Eng Comm 7:302

    Google Scholar 

  14. Prout CK, Kamenar B (1973) Crystal structures of electron-donor-acceptor complexes. In: Foster R (ed) Molecular complexes. Elek, London, pp 151–207

    Google Scholar 

  15. Foster R (1969) Crystal structures. In: Blomquist AT (ed) Organic charge-transfer complexes. Academic, London, pp 216–251

    Google Scholar 

  16. Bent HA (1968) Chem Rev 68:587

    CAS  Google Scholar 

  17. Hassel O (1970) Science 170:497

    CAS  Google Scholar 

  18. Legon AC (1999) Angew Chem Int Ed 38:2686

    Google Scholar 

  19. Brisdon AK (2006) Annu Rep Prog Chem Sect A Inorg Chem 102:160

    CAS  Google Scholar 

  20. Blake JA, Devillanova FA, Gould RO, Li WS, Lippolis V, Parson S, Radek C, Schroder M (1998) Chem Soc Rev 27:195

    CAS  Google Scholar 

  21. Ouvrard C, Le Questel JY, Berthelot M, Laurence C (2003) Acta Crystallogr Sect B: Struct Sci 59:512

    Google Scholar 

  22. du Mont WW, Ruthe F (1999) Coord Chem Rev 189:101

    CAS  Google Scholar 

  23. Amati M, Lelj F, Liantonio R, Metrangolo P, Luzzati S, Pilati T, Resnati G (2004) J Fluor Chem 125:629

    CAS  Google Scholar 

  24. Lenoir D, Chiappe C (2003) Chem Eur J 9:1037

    Google Scholar 

  25. Legon AC (1998) Chem Eur J 4:1890

    CAS  Google Scholar 

  26. Adams CJ, Bowen LE (2005) Dalton Trans, p 2239

    Google Scholar 

  27. Swierczynski D, Luboradzki R, Dolgonos G, Lipkowski J, Schneider HJ (2005) Eur J Org Chem, p 1172

    Google Scholar 

  28. Sanrame CN, Suhrada CP, Dang H, Garcia-Garibay MA (2003) J Phys Chem A 107:3287

    CAS  Google Scholar 

  29. Guthrie F (1863) J Chem Soc 16:239

    Google Scholar 

  30. Seamon WH, Mallet JW (1881) Chem N 44:188

    Google Scholar 

  31. Roussopoulos O (1883) Ber 16:202

    Google Scholar 

  32. Bjorvatten T, Hassel O (1962) Acta Chem Scand 16:249

    CAS  Google Scholar 

  33. Remsen I, Norris JF (1896) Am Chem J 18:90

    CAS  Google Scholar 

  34. Dumas JM, Gomel M, Guerin M (1983) Molecular interactions involving organic halides. In: Patai S, Rappoport Z (eds) The chemistry of functional groups, supplement D. Wiley, New York, pp 985–1020

    Google Scholar 

  35. Xu K, Ho DM, Pascal RA Jr (1994) J Am Chem Soc 116:105

    CAS  Google Scholar 

  36. Corradi E, Meille SV, Messina MT, Metrangolo P, Resnati G (2000) Angew Chem Int Ed 39:1782

    CAS  Google Scholar 

  37. Bernard-Houplain MC, Sandorfy C (1973) Can J Chem 51:3640

    CAS  Google Scholar 

  38. Di Paolo T, Sandorfy C (1974) Chem Phys Lett 26:466

    Google Scholar 

  39. Di Paolo T, Sandorfy C (1974) Can J Chem 52:3612

    Google Scholar 

  40. Trudeau G, Cole KC, Massuda R, Sandorfy C (1978) Can J Chem 56:1681

    CAS  Google Scholar 

  41. Di Paolo T, Sandorfy C (1974) Nature 252:471

    Google Scholar 

  42. Massuda R, Sandorfy C (1977) Can J Chem 55:3211

    CAS  Google Scholar 

  43. Bernard-Houplain MC, Sandorfy C (1973) Can J Chem 51:1075

    CAS  Google Scholar 

  44. Awwadi FF, Willet RD, Peterson KA, Twamley B (2006) Chem Eur J 12:8952

    CAS  Google Scholar 

  45. Politzer P, Lane P, Concha MC, Ma Y, Murray JS (2007) J Mol Model 13:305

    CAS  Google Scholar 

  46. Auffinger P, Hays FA, Westhof E, Ho PS (2004) Proc Natl Acad Sci USA 101:16789

    CAS  Google Scholar 

  47. Fourmigué M, Betail P (2004) Chem Rev 104:5379

    Google Scholar 

  48. Lommerse JPM, Stone AJ, Taylor R, Allen FH (1996) J Am Chem Soc 118:3108

    CAS  Google Scholar 

  49. De Santis A, Forni A, Liantonio R, Metrangolo P, Pilati T, Resnati G (2003) Chem Eur J 9:3974

    Google Scholar 

  50. Walsh RB, Padgett CW, Metrangolo P, Resnati G, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:165

    CAS  Google Scholar 

  51. Clark T, Hennemann M, Murray JS, Politzer P (2007) J Mol Model 13:291

    CAS  Google Scholar 

  52. Valerio G, Raos G, Meille SV, Metrangolo P, Resnati G (2000) J Phys Chem A 104:1617

    CAS  Google Scholar 

  53. Weiss R, Schwab O, Hampel F (1999) Chem Eur J 5:968

    CAS  Google Scholar 

  54. Brammer L, Bruton EA, Sherwood P (2001) Cryst Growth Des 1:277

    CAS  Google Scholar 

  55. Dey A, Jetti RKR, Boese R, Desiraju GR (2003) Cryst Eng Comm 5:248

    CAS  Google Scholar 

  56. Lu YX, Zou JW, Wang YH, Zhang HX, Y QS, Jiang YJ (2006) THEOCHEM 766:119

    CAS  Google Scholar 

  57. Metrangolo P, Pilati T, Resnati G (2006) Cryst Eng Comm 8:946

    CAS  Google Scholar 

  58. Ananthavel SP, Manoharan M (2001) Chem Phys 269:49

    CAS  Google Scholar 

  59. Dunstan S, Henbest HB (1957) J Chem Soc 4905

    Google Scholar 

  60. Mulliken RS (1952) J Phys Chem 56:801

    CAS  Google Scholar 

  61. McAlpine RK (1952) J Am Chem Soc 74:725

    CAS  Google Scholar 

  62. Chen QY, Li ZT, Zhou CM (1993) J Chem Soc Perkin Trans 1:2457

    Google Scholar 

  63. Liantonio R, Luzzati S, Metrangolo P, Pilati T, Resnati G (2002) Tetrahedron 58:4023

    CAS  Google Scholar 

  64. Neukirch H, Guido E, Liantonio R, Metrangolo P, Pilati T, Resnati G (2005) Chem Commun, p 1534

    Google Scholar 

  65. Walsh PL, Ma S, Obst U, Rebek J Jr (1999) J Am Chem Soc 121:7973

    Google Scholar 

  66. Messina T, Metrangolo P, Panzeri W, Ragg E, Resnati G (1998) Tetrahedron Lett 39:9069

    CAS  Google Scholar 

  67. Metrangolo P, Panzeri W, Recupero F, Resnati G (2002) J Fluor Chem 114:27

    CAS  Google Scholar 

  68. Bjovatten T (1968) Acta Chem Scand 22:410

    Google Scholar 

  69. Borgen B, Hassel O, Romming C (1962) Acta Chem Scand 16:2469

    CAS  Google Scholar 

  70. Desiraju GR, Harlow RL (1989) J Am Chem Soc 111:6757

    CAS  Google Scholar 

  71. Bond AD, Griffiths J, Rawson JM, Hulliger J (2001) Chem Commun, p 2488

    Google Scholar 

  72. Britton D, Gleason WB (1977) Acta Crystallogr Sect B: Struct Sci 33:3926

    Google Scholar 

  73. Burdeniuc J, Sanford M, Crabtree RH (1998) J Fluor Chem 91:49

    CAS  Google Scholar 

  74. Burdeniuc J, Crabtree RH, Rheingold AL, Yap GPA (1997) Bull Soc Chim Fr 134:955

    CAS  Google Scholar 

  75. Beck CM, Burdeniuc J, Crabtree RH, Rheingold AL, Yap GPA (1998) Inorg Chim Acta 270:559

    CAS  Google Scholar 

  76. Burdeniuc J, Crabtree RH (1998) Organometallics 17:1582

    CAS  Google Scholar 

  77. Zou J-W, Jiang Y-J, Guo M, Hu G-X, Zhang B, Liu H-C, Yu Q-S (2005) Chem Eur J 11:740

    CAS  Google Scholar 

  78. Gao K, Goroff NS (2000) J Am Chem Soc 122:9320

    CAS  Google Scholar 

  79. Sun A, Lauher JW, Goroff NS (2006) Science 312:1030

    CAS  Google Scholar 

  80. Goroff NS, Curtis SM, Webb JA, Fowler FW, Lauher J (2005) Org Lett 7:1891

    CAS  Google Scholar 

  81. Ghassemzadeh M, Harms K, Dehnicke H (1996) Chem Ber 129:115

    CAS  Google Scholar 

  82. Yamamoto HM, Maeda R, Yamaura J-I, Kato R (2001) J Mater Chem 11:1034

    CAS  Google Scholar 

  83. Gagnaux P, Susz BP (1960) Helv Chim Acta 43:948

    CAS  Google Scholar 

  84. Bock H, Holl S (2001) Z Naturforsch B: Chem Sci 56:111

    CAS  Google Scholar 

  85. Hassel O (1965) Acta Chem Scand 19:2259

    CAS  Google Scholar 

  86. Dahl T, Hassel O (1965) Acta Chem Scand 19:2000

    CAS  Google Scholar 

  87. Holmesland O, Rømming C (1966) Acta Chem Scand 20:2601

    CAS  Google Scholar 

  88. Kuhn N, Abu-Rayyan A, Eichele K, Schwarz S, Steimann M (2004) Inorg Chim Acta 357:1799

    CAS  Google Scholar 

  89. Logothetis TA, Meyer F, Metrangolo P, Pilati T, Resnati G (2004) New J Chem 28:760

    CAS  Google Scholar 

  90. Jones PG, Lozano V (2003) Acta Crystallogr Sect E: Struct Rep Online E59:o632

    CAS  Google Scholar 

  91. Kuhn N, Abu-Rayyan A, Steimann M (2003) Z Anorg Allg Chem 629:2066

    CAS  Google Scholar 

  92. Freytag M, Jones PG (2001) Z Naturforsch B: Chem Sci 56b:889

    Google Scholar 

  93. Freytag M, Jones PG, Ahrens B, Fischer AK (1999) New J Chem 23:1137

    CAS  Google Scholar 

  94. Imakubo T, Tajima N, Shirahata T, Miyake A, Sawa H, Nakamura T, Ohnuki H, Tamura M, Kato R, Izumi M, Nishio Y, Kajiata K (2003) Synth Met 135–136:601

    Google Scholar 

  95. Imakubo T, Tajima N, Kato R, Nishio Y, Kajita K (2003) Synth Met 133–134:181

    Google Scholar 

  96. Devic T, Domercq B, Auban-Senzier P, Molinié P, Fourmigué M (2002) Eur J Inorg Chem 2844

    Google Scholar 

  97. Yamamoto HM, Maeda R, Yamaura J-I, Kato R (2001) Synth Met 120:781

    CAS  Google Scholar 

  98. Imakubo T, Sawa H, Kato R (1995) Chem Commun, p 1667

    Google Scholar 

  99. Domercq B, Devic T, Fourmigué M, Auban-Senzier P, Canadell E (2001) J Mater Chem 11:1570

    CAS  Google Scholar 

  100. Devic T, Bertran JN, Domercq B, Canadell E, Avarvari N, Auban-Senzier P, Fourmigué M (2001) New J Chem 11:1418

    Google Scholar 

  101. Kato R, Imakubo T, Yamamoto H, Maeda R, Fujwara M, Yamaura JI, Sawa H (2002) Mol Cryst Liq Cryst 380:61

    CAS  Google Scholar 

  102. Imakubo T, Sawa H, Kato R (1997) Synth Met 86:1847

    CAS  Google Scholar 

  103. Fourmigué M, Dautel OJ, Devic T, Domercq B (2003) Synth Met 133–134:317

    Google Scholar 

  104. Shirahata T, Kibune M, Maesato M, Kawashima T, Saito G, Imakubo T (2006) J Mater Chem 16:3381

    CAS  Google Scholar 

  105. Imakubo T, Shirahata T, Hervé K, Ouahab L (2006) J Mater Chem 16:162

    CAS  Google Scholar 

  106. Weiss R, Rechinger M, Hampel F (1994) Angew Chem Int Ed 33:893

    Google Scholar 

  107. Leser J, Rabinovich D (1978) Acta Crystallogr Sect B: Struct Sci 34:2250

    Google Scholar 

  108. Scherfise KD, Weller F, Dehnicke K (1985) Z Naturforsch B: Chem Sci 40:906

    Google Scholar 

  109. Vogt H, Lauritsen K, Riesel L, von Lowis M, Reck G (1993) Z Naturforsch B: Chem Sci 48:1760

    CAS  Google Scholar 

  110. Bozopoulos A, Kavounis CA (2004) Z Kristallogr – New Cryst Struct 219:501

    CAS  Google Scholar 

  111. Gustafsson B, Håkansson M, Jagner S (2005) Inorg Chim Acta 358:1309

    CAS  Google Scholar 

  112. Saha MK, Bernal I, Fronczek FR (2004) Chem Commun, p 84

    Google Scholar 

  113. Haberecht M, Lerner HW, Bolte M (2006) Acta Crystallogr Sect E: Struct Rep Online E62:o2836

    CAS  Google Scholar 

  114. Zhdankin VV, Callies JA, Hanson KJ, Bruno J (1999) Tetrahedron Lett 40:1839

    CAS  Google Scholar 

  115. Foucaud A (1983) Positive halogen compounds. In: Pattai S, Rappoport Z (eds) The chemistry of functional groups, supplement D. Wiley, New York, pp 441–480

    Google Scholar 

  116. Creighton JA, Thomas KM (1972) J Chem Soc Dalton Trans 1972:403

    Google Scholar 

  117. Metrangolo P, Meyer F, Resnati G, Ursini M (2005) In: Soloshonok VA (ed) Fluorine-containing synthons. ACS symposium series 911. Oxford University Press/American Chemical Society, Washington, DC, p 514

    Google Scholar 

  118. Zhu S, Jiang H, Zhao J, Li Z (2005) Cryst Growth Des 5:1675

    CAS  Google Scholar 

  119. Vogt H, Frauendorf C, Fischer A, Jones PG (1995) Z Naturforsch B: Chem Sci 50:223

    CAS  Google Scholar 

  120. Lindner HJ, Kitschke-von Gross B (1976) Chem Ber 109:314

    CAS  Google Scholar 

  121. Messina MT, Metrangolo P, Panzeri W, Pilati T, Resnati G (2001) Tetrahedron 57:8543

    CAS  Google Scholar 

  122. Britton D, Gleason WB (2002) Acta Crystallogr Sect E: Struct Rep Online E58:o1375

    CAS  Google Scholar 

  123. Chu Q, Wang Z, Huang Q, Yan C, Zhu S (2003) New J Chem 27:1522

    CAS  Google Scholar 

  124. Zhu S, He P (2005) Tetrahedron 61:5679

    CAS  Google Scholar 

  125. Zhu S, Xu B, Qin C, Xu G (1997) Inorg Chem 36:4909

    CAS  Google Scholar 

  126. Zongzhen L, Chaozhou N, Yilin M (1984) Huagong Xuebao (Chin Ed) 42:120

    Google Scholar 

  127. Liantonio R, Metrangolo P, Pilati T, Resnati G (2003) Cryst Growth Des 3:355

    CAS  Google Scholar 

  128. Bailey RD, Hook LL, Watson RP, Hanks TW, Pennington WT (2000) Cryst Eng 3:155

    CAS  Google Scholar 

  129. Tebbe KF, Grafe-Kavoosian A (1996) Z Naturforsch B: Chem Sci 51:1007

    CAS  Google Scholar 

  130. Tebbe KF, Frohlich R (1983) Z Anorg Allg Chem 505:7

    CAS  Google Scholar 

  131. Tebbe KF, Frohlich R (1983) Z Anorg Allg Chem 505:19

    CAS  Google Scholar 

  132. Bock H, Holl S (2002) Z Naturforsch B: Chem Sci 57:843

    CAS  Google Scholar 

  133. Rosokha SV, Neretin IS, Rosokha TY, Hecht J, Kochi JK (2006) Heteroat Chem 17:449

    CAS  Google Scholar 

  134. Batsanov AS, Howard JAK (2000) Acta Crystallogr Sect C: Cryst Struct Commun C56:252

    CAS  Google Scholar 

  135. Romaniello P, Lelj F (2002) J Phys Chem A 106:9114

    CAS  Google Scholar 

  136. Bondi A (1964) J Phys Chem 68:441

    CAS  Google Scholar 

  137. Pedireddi VR, Shekhar Reddy D, Satish Goud B, Craig DC, Rae AD, Desiraju GR (1994) J Chem Soc Perkin Trans II 11:2353

    Google Scholar 

  138. Chu Q, Zhemin W, Huang Q, Yan C, Zhu S (2001) J Am Chem Soc 123:11069

    CAS  Google Scholar 

  139. Bjorvatten T, Hassel O (1961) Acta Chem Scand 15:1429

    CAS  Google Scholar 

  140. Gagnaux P, Susz BP (1960) Helv Chim Acta 43:948

    CAS  Google Scholar 

  141. Navarrini W, Metrangolo P, Pilati T, Resnati G (2000) New J Chem 24:777

    CAS  Google Scholar 

  142. Forni A, Metrangolo P, Pilati T, Resnati G (2004) Cryst Growth Des 4:291

    CAS  Google Scholar 

  143. Padgett CW, Walsh RD, Drake GW, Hanks TW, Pennington WT (2005) Cryst Growth Des 5:745

    Google Scholar 

  144. Imakubo T, Maruyma T, Sawa H, Kobayashi K (1998) Chem Commun 1998:2021

    Google Scholar 

  145. Imakubo T, Kibune M, Yoshino H, Shirahata T, Yoza K (2006) J Mater Chem 16:4110

    CAS  Google Scholar 

  146. Crihfield A, Hartwell J, Phelps D, Walsh RB, Harris JL, Payne JF, Pennington WT, Hanks TW (2003) Cryst Growth Des 3:313

    CAS  Google Scholar 

  147. Leroy J, Schöllhorn B, Syssa-Magalé J-L, Boubekeur K, Palvadeau P (2004) J Fluor Chem 125:1379

    CAS  Google Scholar 

  148. Pigge FC, Vangala VR, Swenson DC (2006) Chem Commun, p 2123

    Google Scholar 

  149. Syssa-Magalé J-L, Boubekeurb K, Schöllhorn B (2005) J Mol Struct 737:103

    Google Scholar 

  150. Britton D (2003) Acta Crystallogr, Sect E: Struct Rep Online E59:o1332

    CAS  Google Scholar 

  151. Naso F, Cardellicchio C, Capozzi MAM, Capitelli F, Bertolasi V (2006) New J Chem 30:1782

    CAS  Google Scholar 

  152. Syssa-Magalé J-L, Boubekeur K, Palvadeau P, Meerschaut A, Schollhorn B (2004) J Mol Struct 691:79

    Google Scholar 

  153. Thaimattam R, Xue F, Sarma JARP, Mak TCW, Desiraju GR (2001) J Am Chem Soc 123:4432

    CAS  Google Scholar 

  154. Grebe J, Geiseler G, Harms K, Dehnicke K (1999) Z Naturforsch B: Chem Sci 54:77

    CAS  Google Scholar 

  155. Farnham WB, Dixon DA, Calabrese JC (1988) J Am Chem Soc 110:8453

    CAS  Google Scholar 

  156. Ahrens B, Jones PG (1999) Acta Crystallogr Sect C: Cryst Struct Commun 55:1308

    Google Scholar 

  157. Allen FH, Goud BS, Hoy VJ, Howard JAK, Desiraju GR (1994) Chem Commun, p 2729

    Google Scholar 

  158. Sarma JARP, Allen FH, Hoy VJ, Howard JAK, Thaimattam R, Biradha K, Desiraju GR (1997) Chem Commun, p 101

    Google Scholar 

  159. Hulliger J, Langley PJ (1998) Chem Commun, p 2557

    Google Scholar 

  160. Masciocchi N, Bergamo M, Sironi A (1998) Chem Commun, p 1347

    Google Scholar 

  161. Ranganathan A, Pedireddi VR (1998) Tetrahedron Lett 39:1803

    CAS  Google Scholar 

  162. Lucassen ACB, Vartanian M, Leitus G, van der Boom ME (2005) Cryst Growth Des 5:1671

    CAS  Google Scholar 

  163. Burton DD, Fontana F, Metrangolo P, Pilati T, Resnati G (2003) Tetrahedron Lett 44:645

    CAS  Google Scholar 

  164. Corradi E, Mille SV, Messina MT, Metrangolo P, Resnati G (1999) Tetrahedron Lett 40:7519

    CAS  Google Scholar 

  165. Cardillo P, Corradi E, Lunghi A, Mille SV, Messina MT, Metrangolo P, Resnati G (2000) Tetrahedron 56:5535

    CAS  Google Scholar 

  166. Dahl T, Hassel O (1968) Acta Chem Scand 22:2851

    CAS  Google Scholar 

  167. Metrangolo P, Pilati T, Resnati G, Stevenazzi A (2004) Chem Commun, p 1492

    Google Scholar 

  168. Liantonio R, Metrangolo P, Pilati T, Resnati G (2002) Acta Crystallogr: Struct Rep Online E58:575

    Google Scholar 

  169. Jay JI, Padgett CW, Walsh RDB, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:501

    CAS  Google Scholar 

  170. Blackstock SC, Kochi JK (1987) J Am Chem Soc 109:2484

    CAS  Google Scholar 

  171. Blackstock SC, Lorand JP, Kochi JK (1987) J Org Chem 52:1451

    CAS  Google Scholar 

  172. Dahl T, Hassel O (1971) Acta Chem Scand 25:2168

    CAS  Google Scholar 

  173. Guardigli C, Liantonio R, Mele ML, Metrangolo P, Resnati G (2003) Supramol Chem 15:177

    CAS  Google Scholar 

  174. Messina MT, Metrangolo P, Quici S, Manfredi A, Pilati T, Resnati G (2000) Supramol Chem 12:405

    Google Scholar 

  175. Marras G, Metrangolo P, Meyer F, Pilati T, Resnati G (2006) New J Chem 30:1397

    CAS  Google Scholar 

  176. George S, Nangia A, Lam C-K, Mak TCW, Nicoud J-F (2004) Chem Commun, p 1202

    Google Scholar 

  177. Yamamoto HM, Yamaura J-I, Kato R (1998) J Mater Chem 8:15

    CAS  Google Scholar 

  178. Casnati A, Liantonio R, Metrangolo P, Resnati G, Ungaro R, Ugozzoli F (2006) Angew Chem Int Ed 45:1915

    CAS  Google Scholar 

  179. Thalladi VR, Sathish Goud B, Hoy VJ, Allen FH, Howard JAK, Desiraju GR (1996) Chem Commun, p 401

    Google Scholar 

  180. Weiss R, Rechinger M, Hampel F, Wolski A (1995) Angew Chem Int Ed 34:441

    CAS  Google Scholar 

  181. Gattuso G, Liantonio R, Metrangolo P, Meyer F, Resnati G, Pappalardo A, Parisi MF, Pilati T, Pisagatti I (2006) Supramol Chem 18:235

    CAS  Google Scholar 

  182. Bock H, Holl S (2001) Z Naturforsch B: Chem Sci 56:152

    CAS  Google Scholar 

  183. Yamamoto HM, Yamaura J-I, Kato R (1999) Synth Met 102:1448

    CAS  Google Scholar 

  184. Yamamoto HM, Yamaura J-I, Kato R (1999) Synth Met 102:1515

    CAS  Google Scholar 

  185. Caronna T, Liantonio R, Logothetis TA, Metrangolo P, Pilati T, Resnati G (2004) J Am Chem Soc 126:4500

    CAS  Google Scholar 

  186. Guido E, Metrangolo P, Panzeri W, Pilati T, Resnati G, Ursini M, Logothtis TA (2006) J Fluor Chem 126:197

    Google Scholar 

  187. Bertani R, Chaux F, Gleria M, Metrangolo P, Milani R, Pilati T, Resnati G, Sansotera M, Venzo A (2007) Inorg Chim Acta 360:1191

    CAS  Google Scholar 

  188. Liantonio R, Metrangolo P, Meyer F, Pilati T, Navarrini W, Resnati G (2006) Chem Commun, p 1819

    Google Scholar 

  189. Dahl T, Hassel O (1970) Acta Chem Scand 24:377

    CAS  Google Scholar 

  190. du Mont W-W, Stenzel V, Jeske J, Jones PG, Sebald A, Pohl S, Saak W, Batcher M (1994) Inorg Chem 33:1502

    CAS  Google Scholar 

  191. Lindeman SV, Hecht J, Kochi JK (2003) J Am Chem Soc 125:11597

    CAS  Google Scholar 

  192. Weiss R, Rechinger M, Hampel F, Wolski A (1995) Angew Chem Int Ed 34:441

    CAS  Google Scholar 

  193. Ghassemzadeh M, Harms K, Dehnicke K (1996) Chem Ber 129:259

    CAS  Google Scholar 

  194. Metrangolo P, Meyer F, Pilati T, Proserpio DM, Resnati G (2007) Chem Eur J 13:5765

    CAS  Google Scholar 

  195. Thaimattam R, Sharma CVK, Clearfield A, Desiraju GR (2001) Cryst Growth Des 1:103

    CAS  Google Scholar 

  196. Shekhar Reddy D, Craig DC, Desiraju GR (1994) J Chem Soc, Chem Commun, p 1457

    Google Scholar 

  197. Blatov VA, Carlucci L, Ciani G, Proserpio DM (2004) Cryst Eng Comm 6:378

    Google Scholar 

  198. Baburin IA, Blatov VA, Carlucci L, Ciani G, Proserpio DM (2005) J Solid State Chem 178:2452

    CAS  Google Scholar 

  199. Carlucci L, Ciani G, Proserpio DM (2006) In: Braga D, Grepioni F (eds) Making crystals by design: methods, techniques and applications. Wiley, Weinheim, pp 58–86

    Google Scholar 

  200. Batten S (2007) Interpenetration http://www.chem.monash.edu.au/staff/sbatten/interpen/index.html , last visited: 30 July 2007

  201. Batten SR, Robson R (1998) Angew Chem Int Ed 37:1460

    Google Scholar 

  202. Corey EJ (1967) Pure Appl Chem 14:19

    CAS  Google Scholar 

  203. Desiraju GR (1995) Angew Chem Int Ed 34:2311

    CAS  Google Scholar 

  204. Simard M, Su D, Wuest JD (1991) J Am Chem Soc 113:4696

    CAS  Google Scholar 

  205. Metrangolo P, Resnati G (2004) Halogen bonding. In: Atwood JL, Steed JW (eds) Encyclopedia of supramolecular chemistry. Dekker, New York, p 1484

    Google Scholar 

  206. Mele A, Metrangolo P, Neukirch H, Pilati T, Resnati G (2005) J Am Chem Soc 127:14972

    CAS  Google Scholar 

  207. Takeuchi T, Minato Y, Takase M, Shinmori H (2005) Tetrahedron Lett 46:9025

    CAS  Google Scholar 

  208. Messina MT, Metrangolo P, Navarrini W, Radice S, Resnati G, Zerbi G (2000) J Mol Struct 524:87

    CAS  Google Scholar 

  209. Mishra A, Pullin ADE (1971) Aust J Chem 24:2493

    Article  CAS  Google Scholar 

  210. Cheetham NF, McNaught IJ, Pullin ADE (1974) Aust J Chem 27:973

    Article  CAS  Google Scholar 

  211. Cheetham NF, McNaught IJ, Pullin ADE (1974) Aust J Chem 27:987

    Article  CAS  Google Scholar 

  212. McNaught IJ, Pullin ADE (1974) Aust J Chem 27:1009

    Article  CAS  Google Scholar 

  213. Van Dyke Tiers G (2000) J Fluor Chem 102:175

    Google Scholar 

  214. Larsen DW, Allred AL (1965) J Phys Chem 69:2400

    CAS  Google Scholar 

  215. Bruno TJ, Martire DE, Harbison MWP, Nikolic A, Hammer CF (1983) J Phys Chem 87:2430

    CAS  Google Scholar 

  216. Martire DE, Sheridan JP, King JW, O'Donnell SE (1976) J Am Chem Soc 98:3101

    CAS  Google Scholar 

  217. Green RD, Martin JS (1968) J Am Chem Soc 90:3659

    CAS  Google Scholar 

  218. Bertrán JF, Rodríguez M (1979) Org Magn Res 12:92

    Google Scholar 

  219. Bertrán JF, Rodríguez M (1980) Org Magn Res 14:244

    Google Scholar 

  220. Glaser R, Chen N, Wu H, Knotts N, Kaupp M (2004) J Am Chem Soc 126:4412

    CAS  Google Scholar 

  221. Rege PD, Malkina OL, Goroff NS (2002) J Am Chem Soc 124:370

    CAS  Google Scholar 

  222. Semin GK, Babushkina TA, Khrlakyan SP, Pervova EY, Shokina VV, Knunyants IL (1968) Teor Exsp Khim 4:275

    CAS  Google Scholar 

  223. Semin GK, Babushkina TA, Khrlakyan SP, Pervova EY, Shokina VV, Knunyants IL (1968) Chem Abstr 69:72685z

    Google Scholar 

  224. Mugnaini V, Punta C, Liantonio R, Metrangolo P, Recupero F, Resnati G, Pedulli GF, Lucarini M (2006) Tetrahedron Lett 47:3265

    CAS  Google Scholar 

  225. Xu J, Liu X, Ng JK-P, Lin T, He C (2006) J Mater Chem 16:3540

    CAS  Google Scholar 

  226. Stevenson DP, Coppinger GM (1962) J Am Chem Soc 84:149

    CAS  Google Scholar 

  227. Haszeldine RN (1953) J Chem Soc 2622

    Google Scholar 

  228. Geron C, Gomel M (1979) J Chim Phys 76:411

    CAS  Google Scholar 

  229. Dumas JM, Gomel M (1975) J Chim Phys 72:953

    CAS  Google Scholar 

  230. Dumas JM, Geron C, Kribii AR, Lakraimi M (1984) Can J Chem 62:2634

    CAS  Google Scholar 

  231. Monteau J, Huser H, Guérin M, Gomel M (1978) J Chem Res (S) 256

    Google Scholar 

  232. Monteau J, Huser H, Guérin M, Gomel M (1978) J Chem Res (M) 3217

    Google Scholar 

  233. Dumas JM, Geron C, Peurichard H, Gomel M (1976) Bull Soc Chim Fr, p 720

    Google Scholar 

  234. Davidson AW, VanderWerf CA, Boatright LG (1947) J Am Chem Soc 69:3045

    CAS  Google Scholar 

  235. Sheridan JP, Martire DE, Tewari YB (1972) J Am Chem Soc 94:3294

    CAS  Google Scholar 

  236. Sheridan JP, Martire DE, Banda FP (1973) J Am Chem Soc 95:4788

    CAS  Google Scholar 

  237. Cheetham NF, Pullin ADE (1970) Aust J Chem 24:479

    Article  Google Scholar 

  238. McDaniel DH, Deiters SRM (1966) J Am Chem Soc 88:2607

    CAS  Google Scholar 

  239. Brown RN (1961) Acta Crystallogr 14:711

    CAS  Google Scholar 

  240. Jabay O, Pritzkow H, Jander J (1977) Z Naturforsch B: Chem Sci 32:1416

    Google Scholar 

  241. Padmanabhan K, Paul IC, Curtin DY (1990) Acta Crystallogr C: Cryst Struct Commun 46:88

    Google Scholar 

  242. Ghassemzadeh M, Harms K, Dehnicke K, Magull J (1994) Z Naturforsch B: Chem Sci 49:506

    Google Scholar 

  243. Ghassemzadeh M, Harms K, Dehnicke K, Fenske D (1994) Z Naturforsch B: Chem Sci 49:593

    CAS  Google Scholar 

  244. Svensson C, Albertsson J, Eberson L (1988) Acta Chem Scand B 42:596

    Google Scholar 

  245. Svensson C, Albertsson J, Eberson L (1986) Acta Crystallogr C: Cryst Struct Commun 42:1500

    Google Scholar 

  246. Ghassemzadeh M, Dehnicke K, Goesmann H, Fenske D (1994) Z Naturforsch B: Chem Sci 49:602

    CAS  Google Scholar 

  247. Elding M, Albertsson J, Svensson G, Eberson L (1990) Acta Chem Scand 44:135

    Article  CAS  Google Scholar 

  248. Crowston EH, Lobo AM, Prabhakar S, Rzepa HS, Williams DJ (1984) Chem Commun, p 276

    Google Scholar 

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Authors and Affiliations

  1. Laboratory of Nanostructured Fluorinated Materials (NFMLab), Department of Chemistry, Materials and Chemical Engineering “Giulio Natta”, Politecnico di Milano, 7, via Mancinelli, 20131, Milano, Italy

    Pierangelo Metrangolo, Giuseppe Resnati & Serena Biella

  2. Como Campus, Politecnico di Milano, 7, via Castelnuovo, 22100, Como, Italy

    Pierangelo Metrangolo, Giuseppe Resnati & Serena Biella

  3. C.N.R.-Institute of Molecular Sciences and Technologies, Università di Milano, 19, via Golgi, 20133, Milano, Italy

    Tullio Pilati

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  1. Pierangelo Metrangolo
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  2. Giuseppe Resnati
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  3. Tullio Pilati
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  4. Serena Biella
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Correspondence to Pierangelo Metrangolo or Giuseppe Resnati .

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Metrangolo, P., Resnati, G., Pilati, T., Biella, S. (2007). Halogen Bonding in Crystal Engineering. In: Metrangolo, P., Resnati, G. (eds) Halogen Bonding. Structure and Bonding, vol 126. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_2007_060

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