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

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Supramolecular Synthons and Pattern Recognition 89 not rigorously quantifiable. In this respect, the usage of the synthon concept in crystal engineering and supramolecular chemistry follows very closely its usage in classical organic synthesis. In both these usages, simplification is combined with chemical focus. Given that crystal structures need to be simplified before they can be compared and analysed, the graph set notation doubtless offers an accurate topological description of hydrogen bonded patterns. However, the simplification is drastic and is achieved at the cost of obscuring the chemical nature of the recognition events that are the primary causes of crystallisation. On balance, synthons appear to offer a middle ground wherein simplification is obtained without compromising the chemical information contained in the supramolecular system [83–90]. A common deficiency of the graph set and synthon approaches to crystal structure description is that they represent interactions in a crystal without any indication as to whether they are strong or weak and as to their importance in controlling crystal packing. Such information is available in a new pictorial method called NIPMAT (Nonbonded Interaction Pattern MATrix) that is used to display intermolecular interactions in crystals [91]. A two-dimensional quantitative representation gives a single-view visualisation of the relative strengths of the hydrogen bonding and van der Waals forces operating in the crystal. For example, the crystal structures of 2-, 3- and 4-aminophenols detailed earlier in this article may now be compared through their NIPMAT plots [92]. Examination of Fig. 10 shows that hydrogen bonding between the amino and hydroxy groups is the common, dominant intermolecular interaction as evidenced from the dark grey squares for H6-O1 and H7-N1 in the upper right hand corner of the plot. The contribution from the N-H◊ ◊ ◊p interaction in 2- and 3-aminophenols is revealed by the grey squares for H5-C3/4/5 and H5-C4/5/6 respectively (Figs. 10a, b), whereas this interaction is absent in 4-aminophenol (Fig. 10c). a NIPMAT plot of 2-aminophenol 28 Fig. 10 a – c. Comparison of crystal structures with NIPMAT plots: a 2-aminophenol 28
90 A. Nangia · G.R. Desiraju b c Fig. 10 b, c. 3-aminophenol 29; c 4-aminophenol 27.The darker squares correspond to the shorter intermolecular contacts. The heavy black line on the bar grey scale corresponds to a contact at van der Waals separation 10 “Absence” of Patterns NIPMAT plot of 3-aminophenol 29 NIPMAT plot of 4-aminophenol 27 The theme of the article thus far has been the presence of repeating patterns in crystal structures and their identification. Even though a complete and general connection between molecular and crystal structure has proved to be elusive, it is seen that certain patterns may be associated with specific functional groups. Carboxyl groups tend to form dimers, phenols form catemeric chains, aromatic rings form herringbone patterns and so on. Known patterns can then associate in distinct ways, leading to the phenomenon of polymorphism. More intriguing are cases where the pattern identification itself is difficult. There are instances when, because of competing isoenergetic interactions in a
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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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34 J.P. Glusker structures of magne
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36 J.P. Glusker b a Fig. 28 a, b. A
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Page 65 and 66: 56 J.P. Glusker: Directional Aspect
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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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