198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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Supramolecular Synthons and Pattern Recognition 85 cetanalide, HXACAN, is also dimorphic with synthon 58 being present in both the forms. As in resorcinol, linear and nearly tetramer geometries are obtained in forms B and A respectively. Alternating molecules that are utilised in the generation of synthon 58 are related by translation in form B, while such a relation exists between successive molecules in form A (Fig. 7). In some cases, there are distinctive occurrences of the same functionality within a molecular skeleton and so the same synthons can be formed in different ways and locations, leading to polymorphism. Synthons 3 and 59 are typical for primary carboxamides and synthons 60 and 61 are common in aza-heterocycles and imines (Fig. 8). Pyrazine carboxamide, PYRZIN, an antituberculosis drug, is a rare example of a compound with four or so different polymorphic forms (A–D; it is possible that there also exists a fifth form, E, very similar to form A). In each of these forms, a combination of N-H◊◊◊O synthons 3 and 59 and N-H◊◊◊N and C-H◊◊◊N synthons 60 and 61 are optimised by the carboxamide and pyrazine functional groups. Form C has a planar sheet structure whereas the molecules are arranged to form linear ribbons in the other polymorphs. Forms A, B and C contain the common dimer synthon 3, but it should be noted that one or more of the other synthons 59–61 are also optimised and this is what leads to the differences between these polymorphs. Form D has an interesting non-centrosymmetric packing that is characterised by synthon 61 and the unusual synthon 62. Of course, there are some cases where the polymorphs have completely different crystal structures, that is totally different synthons are seen in the various forms. Kinetic factors become significant here. 3-Hydroxybenzoic acid, 2,5-dihydroxybenzoic acid and 2,6-dihydroxybenzoic acid (LEZJAB) are all HEXCAN 58 A B Fig. 7. Polymorphs A and B of 4-hydroxyacetanilide (HEXCAN)
86 A. Nangia · G.R. Desiraju PYRAZIN 3 59 62 60 61 A B C D E Fig. 8. Polymorphs A–D of pyrazine carboxamide (PYRAZIN). A possible fifth polymorph E is very similar to A dimorphic and polymorphism is easy because there are several types of competing hydrogen bond donor (phenolic and carboxylic H-atoms) and acceptor (phenol, carboxyl and carbonyl O-atoms) groups and also because the carboxyl groups can have dimer 1 and catemer 2 arrangements. Inspection of Fig. 9 shows that the two forms of LEZJAB are distinctive. The relationships between the polymorphs of the other hydroxybenzoic acids are similar and involve different combinations of intra- and intermolecular hydrogen bonding. Essentially, the
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198 Topics in Current Chemistry Edi
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Design of Organic Solids Volume Edi
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Volume Editors Prof. Dr. Edwin Webe
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VIII preface tion at an amazing lev
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Contents of Volume 196 Carbon Rich
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2 J.P. Glusker 5 Interactions of Pl
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4 J.P. Glusker Perturbations to the
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6 J.P. Glusker 2.1 Sources of Cryst
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8 J.P. Glusker other induced, will
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10 J.P. Glusker The forces here hav
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12 J.P. Glusker lographic structure
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14 J.P. Glusker a c Fig. 6 a - c. D
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16 J.P. Glusker hydrogen bond H◊
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18 J.P. Glusker Fig. 9. Citric acid
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20 J.P. Glusker peptide plane and a
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22 J.P. Glusker 4.5 F◊◊◊H Int
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24 J.P. Glusker rine-containing com
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26 J.P. Glusker Fig. 17. The packin
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28 J.P. Glusker bind to a metal ion
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30 J.P. Glusker As for carboxylate
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32 J.P. Glusker Fig. 24. The magnes
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138 Y. Aoyama 18 19 Fig. 5. 2D net
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140 Y. Aoyama 24 ded (O-H◊◊◊O
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142 Y. Aoyama 2.4 Interaction-Suppo
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144 Y. Aoyama In the presence of a
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146 Y. Aoyama clusion compounds (se
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148 Y. Aoyama are intriguing guests
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150 Y. Aoyama The tuning or enginee
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152 Y. Aoyama Fig. 16. Binding isot
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154 Y. Aoyama The desorption of the
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156 Y. Aoyama Fig. 17. Suggested me
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158 Y. Aoyama 5 Concluding Remarks
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160 Y. Aoyama 4. Hölderich W, Hess
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Crystalline Polymorphism of Organic
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Author Index Volumes 151-198 Author
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Author Index Volumes 151 - 198 2 1
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Author Index Volumes 151 - 198 213
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Author Index Volumes 151 - 198 2 ]
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Springer and the environment At Spr
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198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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