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

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172 M.R. Caira b c a Fig. 3. a Molecular structure of probucol; b stereoview of the crystal structure of Form I; c stereoview of the crystal structure of Form II. (Adapted from [59] with permission) a b Fig. 4 a, b. Hydrogen bonded layers in nitrofurantoin polymorphs: a a-form; b b-form (Adapted from [60] with permission)
Crystalline Polymorphism of Organic Compounds 173 (~ 3.2 Å) of the respective layers shown in Fig. 4. This example conveys an idea of the variations in polymorphic structural arrangements that are possible with molecules containing hydrogen bonding functionalities. During the last few years, the development of graph set analysis [16] has greatly facilitated the visualisation and comparison of polymorphic structures. Here, hydrogen bonding networks are classified as belonging to one of four distinct patterns, each specified by a designator (G in general): intramolecular (S), chains (C), rings (R), or other finite patterns (D). Further specification of the number of donor (d) and acceptor (a) atoms as well as the total number of atoms (n) comprising the pattern yields a concise and informative description of the hydrogen bonding arrangement, G a d(n).A simple illustration of the use of graph set descriptors is given in Fig. 5 for a polymorph of thalidomide (space group C2/c, Z=8) [62]. Alternating hydrogen bonded ring motifs exist in this polymorphic structure as a result of bifurcated hydrogen bonding involving the N-H group. In contrast, the other known racemic modification of thalidomide (space group P2 1/n, Z=4) [63] contains only centrosymmetric dimers of the type R 2 2(8). Application of graph set analysis to three polymorphs of iminodiacetic acid [64] has led not only to facile comparison of the crystal structures, but has also provided a basis for concise description of the polymorphic transformations occurring in that system. Thus, e.g. transformation of one polymorph of the acid into another is simply described as a conversion of R 2 2(4) into R 2 4(8). It has been pointed out that graph set analysis of hydrogen bonded systems also provides a means for seeking systematic correlations between the resultant patterns that demonstrate “hydrogen bond pattern functionality”[16].This concept may be useful in the prediction of crystal structures as well as for the design of materials with desired supramolecular features. Extension of the graph set approach to encompass intermolecular atom-atom interactions other than hydrogen bonding for the classification of polymorphic crystal structures is envisaged as a natural and desirable development and more widespread use of this classification can be expected in future. Elucidation of detailed polymorphic structural features and structural changes accompanying polymorphic transformations relies heavily on the single crystal X-ray diffraction technique. The inability to produce single crystals in Fig. 5. Graph set notation for hydrogen bonded ring motifs in a polymorph of thalidomide
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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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38 J.P. Glusker Fig. 30. Complexati
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40 J.P. Glusker 7.1 Descriptions of
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42 J.P. Glusker Fig. 34. Glycine cr
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44 J.P. Glusker bonding capabilitie
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46 J.P. Glusker 2. Non-intercalativ
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48 J.P. Glusker d Fig. 37 d. The ch
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50 J.P. Glusker Fig. 39. Hydrogen-b
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52 J.P. Glusker 72, 104], but other
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54 J.P. Glusker 23. Cody V, Murray-
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56 J.P. Glusker: Directional Aspect
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58 A. Nangia · G.R. Desiraju 7 Sup
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60 A. Nangia · G.R. Desiraju elect
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62 A. Nangia · G.R. Desiraju 14 15
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64 A. Nangia · G.R. Desiraju [23]
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66 A. Nangia · G.R. Desiraju struc
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68 A. Nangia · G.R. Desiraju Fig.
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70 A. Nangia · G.R. Desiraju -NH 2
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72 A. Nangia · G.R. Desiraju ingfu
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74 A. Nangia · G.R. Desiraju and r
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76 A. Nangia · G.R. Desiraju bonds
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78 A. Nangia · G.R. Desiraju 2.86-
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82 A. Nangia · G.R. Desiraju ted a
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84 A. Nangia · G.R. Desiraju envir
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86 A. Nangia · G.R. Desiraju PYRAZ
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88 A. Nangia · G.R. Desiraju napht
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90 A. Nangia · G.R. Desiraju b c F
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92 A. Nangia · G.R. Desiraju all a
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94 A. Nangia · G.R. Desiraju 42. J
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Hydrogen-Bonded Ribbons, Tapes and
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Page 165 and 166: 158 Y. Aoyama 5 Concluding Remarks
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Page 177: Crystalline Polymorphism of Organic
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198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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