Frontiers in Crystal Engineering

339 Pages·2006·13.434 MB·English

by  Edward R. T. Tiekink, Jagadese Vittal

Frontiers in Crystal Engineering
FrontiersinCrystalEngineering. EditedbyEdwardR.T.TiekinkandJagadeseJ.Vittal
 2006 John Wiley & Sons, Ltd. ISBN: 0-470-02258-2
Frontiers in Crystal Engineering
Edited by
Edward R.T. Tiekink
Department of Chemistry, The University of Texas at San Antonio
Jagadese J. Vittal
Department of Chemistry, National University of Singapore
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ISBN-13:978-0-470-02258-0(HB)(acid-freepaper)
ISBN-10:0-470-02258-2(HB)(acid-freepaper)
1.Molecularcrystals–Research.I.Tiekink,EdwardR.T.II.Vittal,
JagadeseJ.
QD921.F762006
548–dc22
2005016323
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Contents
List of Contributors xi
Foreword xiii
1 Applications of Crystal Engineering Strategies in Solvent-free
Reactions: Toward a Supramolecular Green Chemistry 1
1 Introduction 1
1.1 Making Crystals by Smashing Crystals? 3
1.2 Milling, Grinding, Kneading and Seeding 4
2 Mechanochemical Preparation of Hydrogen-Bonded Adducts 6
3 Mechanically Induced Formation of Covalent Bonds 8
3.1 Mechanochemical Preparation of Coordination Networks 10
4 The Solvent-free Chemistry of the Zwitterion
[CoIII(η5-C H COOH)(η5-C H COO)] 13
5 4 5 4
5 Concluding Remarks 18
6 Acknowledgments 20
References 20
2 Crystal Engineering of Pharmaceutical Co-crystals 25
1 Introduction 25
1.1 What Are Co-crystals? 26
1.2 How Are Co-crystals Prepared? 26
1.3 Why Are Co-crystals of Relevance in the Context of APIs? 27
2 What Is the Origin of Polymorphism and Is It Prevalent in Co-crystals? 28
3 What Is a Pharmaceutical Co-crystal? 35
3.1 A Case Study: Pharmaceutical Co-crystals of Carbamazepine, 1
(CBZ, 1) 36
3.2 But Beware of “Fake” Pharmaceutical Co-crystals! 45
4 Conclusions 46
5 Acknowledgments 46
References 46
vi CONTENTS
3 Template-controlled Solid-state Synthesis: Toward a General Form
of Covalent Capture in Molecular Solids 51
1 Introduction 51
1.1 Target-oriented Organic Synthesis 51
1.2 Target-oriented Organic Synthesis and Covalent Capture 52
1.3 Overview 52
2 Controlling Reactivity Using Linear Templates 53
3 Template-controlled Solid-state Reactivity 54
3.1 Template-controlled Reactivity in the Solid state 54
3.2 Resorcinol as a Linear Template 54
3.3 Modularity and Generality 56
4 Target-oriented Organic Synthesis in the Solid State 56
4.1 [2.2]-Paracyclophane 56
4.2 Template Switching 58
4.3 Ladderanes 59
5 Other Linear Templates 61
5.1 1,8-Naphthalenedicarboxylic Acid 61
5.2 Bis-p-phenylene[34]-crown[10] 62
5.3 Carballylic and 1,2,4,5-Benzenetetracarboxylic Acids 62
5.4 Tetrakis(4-iodoperfluorophenyl)erythritol 63
6 Summary and Outlook 64
References 65
4 Interplay of Non-covalent Bonds: Effect of Crystal Structure
on Molecular Structure 67
1 Introduction 67
2 Second-Sphere Coordination 69
3 Soft Coordination Environments 77
3.1 Mercury and Tin 77
3.2 Comparison with Calculation 81
3.3 Influence of Disorder 84
4 Speciation 85
5 Molecular Conformation 87
6 Conclusions 88
References 88
5 Crystal Engineering of Halogenated Heteroaromatic Clathrate Systems 91
1 Introduction 91
1.1 Clathrates 91
1.2 New Clathrand Inclusion Hosts 92
1.3 Halogenated Heteroaromatic Hosts 92
2 Aromatic Edge–Edge C–H···N Dimers 93
3 Heteroatom-1,3-Peri Interactions 95
3.1 The Ether–1,3-Peri Aromatic Hydrogen Interaction 95
3.2 The Thioether–and Aza–1,3-Peri Aromatic Hydrogen Interactions 96
4 Molecular Pen Structures 97
CONTENTS vii
5 Halogenated Edge–Edge Interactions 99
6 Pi–Halogen Dimer (PHD) Interactions 101
6.1 A New Aromatic Building Block 101
6.2 Staircase Inclusion Compounds 101
6.3 Layer Inclusion Compounds 106
7 Molecular Bricks, Spheres and Grids 106
7.1 Bricks and Mortar Inclusion Systems 106
7.2 Molecular Spheres of Variable Composition 108
7.3 Interlocking Molecular Grids 110
8 Conclusions 112
9 Acknowledgments 115
References 115
6 Steric Control over Supramolecular Aggregation: A Design Element
in Crystal Engineering? 117
1 Introduction 117
2 Diorganotin Carboxylates 118
3 Triorganotin Carboxylates 120
4 Binary Zinc Xanthates 123
5 Bipyridine Adducts of Zinc Dithiophosphates 125
6 Binary Mercury Dithiocarbamates 128
7 Binary Bismuth Xanthates 130
8 Conclusions and Outlook 133
9 Acknowledgments 133
References 133
7 Incorporating Molecular Hosts into Network Structures 135
1 Introduction 135
2 Hydrogen-Bonded Structures with CTV 137
2.1 Carborane C–H Donors 137
2.2 N–H and O–H Donor Groups 139
3 Coordination Polymers 144
4 Extended-Arm CTV Derivatives and their Coordination Polymers 149
5 Conclusions 152
6 Acknowledgments 153
References 153
8 Interpenetrating Networks 157
1 Introduction 157
2 Notation 159
3 1-D Nets 162
4 2-D Nets 164
5 3-D Nets 172
6 Unusual Interpenetration 178
7 Consequences of Interpenetration 179
8 Self-Penetration 183
viii CONTENTS
9 Entangled but not Interpenetrating 185
10 Conclusions 187
References 188
9 Architecture and Functional Engineering Based on Paddlewheel
Dinuclear Tetracarboxylate Building Blocks 195
1 Introduction 195
1.1 Paddlewheel Dinuclear Building Block 195
1.2 High-dimensional Frameworks and Their Functions 197
1.3 Electronic Structures of Dinuclear Cores 197
2 Synthetic Strategy 198
2.1 In situ Building Blocks and Preorganized Building Blocks 198
2.2 Preparation of Preorganized Building Blocks (Rh and Ru ) 199
2 2
2.3 Coordination Mode of Axial Positions 200
3 Architecture Engineering Based on Preorganized Building Blocks 201
3.1 High-dimensional (2D and 3D) Architectures 201
3.2 Architectures with High Affinity at Axial Positions of
[Rh (O CCF ) ] 202
2 2 3 4
4 Conductive and Magnetic Properties Based on Preorganized
Building Blocks 206
4.1 Conductivity Based on Mixed-valence System of RhII and Rh II,III
2 2
Cores 206
4.2 Magnetism Based on Paramagnetic Ru II,III (S =3/2) Cores 208
2
4.3 Magnetism Based on Paramagnetic RuII(S =1) Cores 209
2
5 Porous Properties Based on Preorganized and InSitu Building Blocks 212
5.1 Porous Materials 212
5.2 Porous Properties Based on Preorganized Building Blocks 212
5.3 Porous Properties Based on In Situ Building Blocks 213
6 Conclusion and Outlook 216
References 217
10 Supramolecular Interactions in Directing and Sustaining Coordination
Molecular Architectures 219
1 Introduction 219
2 Molecular Architectures Assembled by Hydrogen-Bonding Interactions 220
2.1 Metal Complexes with Aquometal Centers 220
2.2 Metal Complexes with Carboxylic Acid Groups 222
2.3 Metal Complexes with Imidazole Groups 225
2.4 Metal Complexes with CH···X Bonding Sites 229
2.5 Metal Complexes of Biological Relevance 235
3 Molecular Architectures Assembled VIA π···π Interactions 237
3.1 0-D Metal Complexes 237
3.2 1-D Coordination Polymers 239
3.3 2-D Coordination Polymers 245
4 Metallophilic Interactions 248
4.1 Cuprophilic Interactions 248
CONTENTS ix
4.2 Argentophilic Interactions 249
4.3 Aurophilic Interactions 256
5 Concluding Remarks and Outlook 258
6 Acknowledgments 259
References 259
11 The Structure-directing Influence of Hydrogen Bonding in
Coordination Polymers 265
1 Introduction 265
2 A Novel Cadmium Cyanide Network 269
3 Dihydroxybenzoquinone and Chloranilic Acid Derivatives of
Lanthanides 271
4 A Stable Zinc Saccharate Network 275
5 Anionic Metal-Carbonate Networks 282
5.1 Body-centered Cubic Structures 289
5.2 Face-centered Cubic Structures 291
6 Conclusions 294
References 294
12 Hydrogen-bonded Coordination Polymeric Structures 297
1 Introduction 297
2 Solid-State Supramolecular Transformation of Hydrogen-Bonded 3-D
Network to 3-D Coordination Polymeric Network Structures by Thermal
Dehydration 298
3 Interconvertible Solid-state Supramolecular Transformation 301
4 Solid-state Transformation of A Helical Coordination Polymeric
Structure to A 3-D Coordination Network Structure by Thermal
Dehydration 303
5 Influence of Chiral Centers on the Helicity of the Coordination Polymers 306
6 Consequences of C=O···π Interactions 308
7 Supramolecular Isomerism 310
8 Starlike Channels and Hexagonal Diamondoid Topology 312
9 Hydrogen-bonded Helical Water Molecules Inside A Staircase 1-D
Coordination Polymer 313
10 Hydrogen-bonded Polyrotaxane-like Structure Containing Cyclic (H O)
2 4
in [Zn(OAc) (µ-bpe)]·2H O 316
2 2
11 Summary 316
12 Acknowledgments 317
References 317
Index 321
List of Contributors
BrendanF. Abrahams,SchoolofChemistry,UniversityofMelbourne,Victoria,Australia
Stuart R. Batten, School of Chemistry, Monash University, Clayton, Victoria, Australia
Roger Bishop, School of Chemistry, The University of New South Wales, Sydney, New
South Wales, Australia
Dario Braga, Dipartimento di Chimica G. Ciamician, University of Bologna, Bologna,
Italy
Xiao-MingChen,SchoolofChemistryandChemicalEngineering,SunYat-SenUniversity,
Guangzhou, China
Daniela D’Addario, Dipartimento di Chimica G. Ciamician, University of Bologna,
Bologna, Italy
Gautam R. Desiraju, School of Chemistry, University of Hyderabad, Hyderabad, India
Tomislav Frisˇcˇic´, Department of Chemistry, University of Iowa, Iowa City, Iowa, USA
Shuhei Furukawa, Department of Synthetic Chemistry and Biological Chemistry, Kyoto
University, Katsura, Japan
Stefano Giaffreda, Dipartimento di Chimica G. Ciamician, University of Bologna,
Bologna, Italy
Fabrizia Grepioni, Dipartimento di Chimica G. Ciamician, University of Bologna,
Bologna, Italy
Michaele J.Hardie, School of Chemistry, University of Leeds, Leeds, UK
Susumu Kitagawa, Department of Synthetic Chemistry and Biological Chemistry, Kyoto
University, Katsura, Japan