Making crystals from crystals: a green route to crystal engineering and polymorphism.

Supramolecular reactions between crystalline materials as well as reactions between a crystalline material and a vapour can be used to generate new crystalline substances. These solvent-free processes can be exploited to prepare both hydrogen-bonded co-crystals and coordination networks. Solid-vapour reactions do not differ from solid-vapour uptake/release processes, and can also be used to prepare polymorphs and solvates. It is argued that solvent-less reactions involving molecular crystals represent a green route to supramolecular solid-state chemistry and crystal engineering.

[1]  T. Steiner.  The hydrogen bond in the solid state. , 2002, Angewandte Chemie.

[2]  P. Bassi,et al.  MECHANISM OF THE REACTION BETWEEN HYDROCARBONS AND PICRIC ACID IN THE SOLID STATE , 1963 .

[3]  D. Braga,et al.  Mechanochemical preparation of hydrogen-bonded adducts between the diamine 1,4-diazabicyclo[2.2.2]octane and dicarboxylic acids of variable chain length: an X-ray diffraction and solid-state NMR study. , 2003, Chemistry.

[4]  S. Batten,et al.  Structure and magnetism of coordination polymers containing dicyanamide and tricyanomethanide , 2003 .

[5]  G. Koten,et al.  Self-assembled Organoplatinum(II) Supermolecules as Crystalline, SO2 Gas-triggered Switches , 2000 .

[6]  G. Kaupp.  AFM on Chemically Reacting Crystals , 1994 .

[7]  J. Steed,et al.  Engineering of porous π-stacked solids using mechanochemistry , 2001 .

[8]  A. Blake,et al.  Supramolecular design of one-dimensional coordination polymers based on silver(I) complexes of aromatic nitrogen-donor ligands , 2001 .

[9]  M. Ward,et al.  Nanoporous Molecular Sandwiches: Pillared Two-Dimensional Hydrogen-Bonded Networks with Adjustable Porosity , 1997, Science.

[10]  T. Threlfall.  Analysis of organic polymorphs. A review , 1995 .

[11]  M. O'keeffe,et al.  Advances in the chemistry of metal–organic frameworks , 2002 .

[12]  D. Braga,et al.  A remarkable water-soluble (molecular) alloy with two tuneable solid-to-solid phase transitions , 2001 .

[13]  Christoph Janiak,et al.  A critical account on π–π stacking in metal complexes with aromatic nitrogen-containing ligands , 2000 .

[14]  D. Braga,et al.  Mechanistic studies of heterophase protonation and deprotonation reactions of solid [CoIII(η5–C5H4COOH)(η5–C5H4COO)] using supermicroscopy , 2003 .

[15]  Gordon J. T. Tiddy,et al.  Crystal engineering – nucleation, the key step , 2002 .

[16]  Jack D. Dunitz,et al.  Crystal and co-crystal: A second opinion , 2003 .

[17]  I. Paul,et al.  Solid-state formation of quinhydrones from their components: use of solid-solid reactions to prepare compounds not accessible from solution , 1984 .

[18]  G. Bruni,et al.  A Novel Method to Obtain a β-Cyclodextrin Inclusion Compound by Solid State Reaction: the Ketoprofen Case Revisited , 1999 .

[19]  D. Braga,et al.  Crystal Engineering and Organometallic Architecture. , 1998, Chemical reviews.

[20]  J. Ripmeester,et al.  Transforming the Dense Polymorph into a Versatile New Microporous Framework , 1999 .

[21]  I. Paul,et al.  Reaction of ammonia gas with crystalline benzoic and related acids , 1971 .

[22]  S. G. Harris,et al.  Characterisation of TiN and TiAlN thin films deposited on ground surfaces using focused ion beam milling , 2004 .

[23]  Lee Brammer,et al.  New trends in crystal engineering , 2005 .

[24]  D. Braga,et al.  Assembly of hybrid organic-organometallic materials through mechanochemical acid-base reactions. , 2003, Chemistry.

[25]  D. Braga,et al.  Crystal Forms of Hexafluorophosphate Organometallic Salts and the Importance of Charge-Assisted C−H---F Hydrogen Bonds , 1998 .

[26]  S. Watano,et al.  Development of a novel vertical high shear kneader and its performance in wet kneading of pharmaceutical powders. , 2002, Chemical & pharmaceutical bulletin.

[27]  Xiao‐Ming Chen,et al.  Anionic and neutral metal-4,4'-bipyridine networks. Synthesis, structures and thermal properties of one- and three-dimensional coordination polymers constructed by metal salts and 4,4'-bipyridine , 2000 .

[28]  R. Robson,et al.  A net-based approach to coordination polymers , 2000 .

[29]  Margaret C. Etter,et al.  Hydrogen bonds as design elements in organic chemistry , 1991 .

[30]  Roger J. Davey,et al.  Pizzas, polymorphs and pills , 2003 .

[31]  D. Braga,et al.  Making and converting organometallic pseudo-polymorphs via non-solution methods , 2000 .

[32]  William Jones,et al.  Selective polymorph transformation via solvent-drop grinding. , 2005, Chemical communications.

[33]  M. C. Etter,et al.  Polymorphism in anthranilic acid: a reexamination of the phase transitions , 1992 .

[34]  F. Albert Cotton,et al.  The first dirhodium-based supramolecular assemblies with interlocking lattices and double helices , 2001 .

[35]  D. Braga,et al.  Hydrogen Bonds within an Ionic Environment: The Remarkable Behavior of the Zwitterion [CoIII(η5-C5H4COOH)(η5-C5H4COO)] , 1999 .

[36]  D. Mootz,et al.  Molecular Beside Ionic: Crystal Structures of a 1/1 and a 1/4 Adduct of Pyridine and Formic Acid. , 1999, Angewandte Chemie.

[37]  K. Matsuda,et al.  Absolute asymmetric photocyclization of a photochromic diarylethene derivative in single crystals. , 2003, Angewandte Chemie.

[38]  I. Paul,et al.  Reaction of ammonia gas with crystalline substituted benzoic anhydrides , 1972 .

[39]  Dario Braga,et al.  Crystal Engineering: From Molecules and Crystals to Materials , 1999 .

[40]  D. Braga,et al.  Intermolecular interactions in nonorganic crystal engineering. , 2000, Accounts of chemical research.

[41]  C. C. Chiang,et al.  The crystal and molecular structures of S-(+)-2,2-diphenylcyclopropanecarboxylic acid and of R-(+)-2,2-diphenyl-1-methylcyclopropanecarboxylic acid. A study of the environments of gas-solid reactions that exhibit anisotropic behavior , 1977 .

[42]  Fumio Toda,et al.  Efficient solid-state reactions of alcohols: dehydration, rearrangement, and substitution , 1990 .

[43]  S Natarajan,et al.  Aufbau principle of complex open-framework structures of metal phosphates with different dimensionalities. , 2001, Accounts of chemical research.

[44]  F. W. Fowler,et al.  A Supramolecular Solution to a Long‐Standing Problem: The 1,6‐Polymerization of a Triacetylene , 2000 .

[45]  J. Bernstein,et al.  Disappearing and reappearing polymorphs. The benzocaine:picric acid system. , 2001, Journal of the American Chemical Society.

[46]  I. Dance.  Inorganic intermolecular motifs, and their energies , 2003 .

[47]  I. Paul,et al.  Reactions of molecular crystals with gases. II. X-ray structure of crystalline 4-chlorobenzoic acid and the anisotropy of its reaction with ammonia gas , 1974 .

[48]  Kenneth D M Harris,et al.  How to determine structures when single crystals cannot be grown: opportunities for structure determination of molecular materials using powder diffraction data. , 2004, Chemical Society reviews.

[49]  M. Ward,et al.  Metric engineering of soft molecular host frameworks. , 2001, Accounts of chemical research.

[50]  W. Jones,et al.  Crystal Engineering of Organic Cocrystals by the Solid-State Grinding Approach , 2005 .

[51]  V. Boldyrev,et al.  Mechanochemistry of Solids: Past, Present, and Prospects , 2000 .

[52]  Masashi Miyauchi,et al.  Polymorphs of a Cocrystal with Achiral and Chiral Structures Prepared by Pseudoseeding: Tryptamine/Hydrocinnamic Acid , 2001 .

[53]  A. Burrows.  Crystal engineering using multiple hydrogen bonds , 2004 .

[54]  Davide M. Proserpio,et al.  Borromean links and other non-conventional links in ‘polycatenated’ coordination polymers: re-examination of some puzzling networks , 2003 .

[55]  L. MacGillivray,et al.  Exploiting modularity in template-controlled synthesis: a new linear template to direct reactivity within discrete hydrogen-bonded molecular assemblies in the solid state. , 2001, Chemical communications.

[56]  D. Braga,et al.  Intermolecular interactions and supramolecular organization in organometallic solids , 1996 .

[57]  C. Wilson.  Migration of the proton in the strong O-H.O hydrogen bond in urea-phosphoric acid (1/1). , 2001, Acta crystallographica. Section B, Structural science.

[58]  M. Zaworotko,et al.  From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. , 2001, Chemical reviews.

[59]  Orn Almarsson,et al.  Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? , 2003, Chemical communications.

[60]  D. Breimer.  Topics in Pharmaceutical Sciences , 1982 .

[61]  Gerhard M. J. Schmidt,et al.  Photodimerization in the solid state , 1971 .

[62]  D. Braga,et al.  Design of Organometallic Molecular and Ionic Materials , 2001 .

[63]  J. Rouland,et al.  Bifonazole-β-cyclodextrin Inclusion Complexes. Thermal analysis and X-ray powder diffraction study , 2000 .

[64]  Mitsuru Kondo,et al.  A New, Methane Adsorbent, Porous Coordination Polymer [{CuSiF6(4,4′-bipyridine)2}n] , 2000 .

[65]  J. R. Greene,et al.  A system for studying gas-solid reaction kinetics in controlled atmospheres , 1992 .

[66]  G. Desiraju.  Counterpoint: what's in a name? , 2004 .

[67]  Dario Braga,et al.  Crystal engineering, where from? Where to? , 2003, Chemical communications.

[68]  M. W. Hosseini,et al.  Crystal engineering: molecular networks based on inclusion phenomena , 1998 .

[69]  D. Braga,et al.  Mechanochemical assembly of hydrogen bonded organic-organometallic solid compounds. , 2002, Chemical communications.

[70]  J. Hulliger.  Markov-type evolution of materials into a polar state. , 2002, Chemistry.

[71]  S. Kobatake,et al.  Reversible surface morphology changes of a photochromic diarylethene single crystal by photoirradiation. , 2001, Science.

[72]  R. Docherty,et al.  Polymorphism in Molecular Crystals: Stabilization of a Metastable Form by Conformational Mimicry , 1997 .

[73]  L. Brammer.  Metals and hydrogen bonds , 2003 .

[74]  G. Wegner,et al.  Crystallographic Study of a Single Crystal to Single Crystal Photodimerization and Its Thermal Reverse Reaction , 1993 .

[75]  C. Janiak.  Engineering coordination polymers towards applications , 2003 .

[76]  M. W. Hosseini.  Reflexion on molecular tectonics , 2004 .

[77]  S Bracco,et al.  Methane and carbon dioxide storage in a porous van der Waals crystal. , 2005, Angewandte Chemie.

[78]  William Jones,et al.  Solvent-drop grinding: green polymorph control of cocrystallisation. , 2004, Chemical communications.

[79]  L Yu,et al.  Amorphous pharmaceutical solids: preparation, characterization and stabilization. , 2001, Advanced drug delivery reviews.

[80]  J. Dunitz,et al.  Low-temperature crystallization of orthorhombic ferrocene: structure analysis at 98 K , 1982 .

[81]  K. Okuda,et al.  A novel preparative method for unsymmetrical ethers by the reaction of cocrystals of two similarly substituted secondary alcohols with toluene-p-sulphonic acid in the solid state , 1991 .

[82]  G. Koten,et al.  Organoplatinum crystals for gas-triggered switches , 2000, Nature.

[83]  Z. Urbańczyk-Lipkowska,et al.  Solid-state structural characterization of 1,3-cyclohexanedione and of a 6:1 cyclohexanedione-benzene cyclamer complex, a novel host-guest species. , 1986, Journal of the American Chemical Society.

[84]  M. Oh,et al.  Manganese tricarbonyl transfer (MTT) reagents in the construction of novel organometallic systems , 2004 .

[85]  T. Friščić,et al.  'Template-switching': a supramolecular strategy for the quantitative, gram-scale construction of a molecular target in the solid state. , 2003, Chemical communications.

[86]  A. Gavezzotti,et al.  Molecular recognition in organic crystals: directed intermolecular bonds or nonlocalized bonding? , 2005, Angewandte Chemie.

[87]  G. Wegner,et al.  SINGLE-CRYSTAL-TO-SINGLE-CRYSTAL PHOTODIMERIZATION OF CINNAMIC ACID , 1993 .

[88]  D. Braga,et al.  Organometallic polymorphism and phasetransitions , 2000 .

[89]  M. Nishio.  CH/π hydrogen bonds in crystals , 2004 .

[90]  L. MacGillivray,et al.  An inverted metal-organic framework with compartmentalized cavities constructed by using an organic bridging unit derived from the solid state. , 2002, Angewandte Chemie.

[91]  D. Braga,et al.  Innovation in crystal engineering , 2002 .

[92]  D. Braga,et al.  Supramolecular gas–solid reaction between formic acid vapours and solid [CoIII(η5-C5H4COOH)(η5-C5H4COO)] , 2002 .

[93]  J. Steed,et al.  Channel-containing 1D coordination polymers based on a linear dimetallic spacer. , 2002, Chemical communications.

[94]  M. J. Calhorda,et al.  Weak hydrogen bonds: theoretical studies , 2000 .

[95]  Grinding of an organometallic crystalline material leads to quantitative formation of a hydrated polymorph , 1999 .

[96]  S. Teat,et al.  Supramolecular motifs in s-block metal-bound sulfonated monoazo dyes, part 1: structural class controlled by cation type and modulated by sulfonate aryl ring position. , 2004, Chemistry.

[97]  Peter Erk,et al.  The innovative momentum of crystal engineering , 2004 .

[98]  D. Braga,et al.  Intra-Solid and Inter-Solid Reactions of Molecular Crystals: a Green Route to Crystal Engineering , 2005 .

[99]  A. J. Blake,et al.  Topological isomerism in coordination polymers , 2001 .

[100]  D. Braga,et al.  Unexpected solid-solid reaction upon preparation of KBr pellets and its exploitation in supramolecular cation complexation. , 2002, Chemical communications.

[101]  G. Kaupp.  Solid-state molecular syntheses: complete reactions without auxiliaries based on the new solid-state mechanism , 2003 .

[102]  T. Friščić,et al.  Supramolecular construction of molecular ladders in the solid state. , 2004, Angewandte Chemie.

[103]  Gautam R. Desiraju,et al.  Crystal and co-crystal , 2003 .

[104]  K. Wieczorek-Ciurowa,et al.  Chemical reactions during high-energy ball milling of the Cu2(OH)2CO3–Al0 system , 2003 .

[105]  Wenbin Lin,et al.  Crystal engineering of NLO materials based on metal--organic coordination networks. , 2002, Accounts of chemical research.

[106]  Takashi Yanagisawa,et al.  Effect of ball milling on morphology of cup-stacked carbon nanotubes , 2002 .

[107]  Gautam R Desiraju,et al.  Hydrogen bridges in crystal engineering: interactions without borders. , 2002, Accounts of chemical research.

[108]  D. Braga,et al.  Reversible trapping of acid and base vapours into an amphoteric crystalline material. , 2001, Chemical communications.

[109]  M. Fujita,et al.  Self-Assembly of [2]Catenanes Containing Metals in Their Backbones , 1999 .

[110]  T. Güneri,et al.  Improvement in the Physicochemical Properties of Ketoconazole through Complexation with Cyclodextrin Derivatives , 2002 .

[111]  D. Fox.  Physics and Chemistry of the Organic Solid State , 1963 .

[112]  D. Braga,et al.  Supramolecular complexation of alkali cations through mechanochemical reactions between crystalline solids. , 2004, Chemistry.

[113]  K. Seddon.  Pseudopolymorph: A Polemic , 2004 .

[114]  M. W. Hosseini.  Molecular tectonics: from molecular recognition of anions to molecular networks , 2003 .

[115]  D. Braga,et al.  cation-anion hydrogen bonded pseudo-polymorph upon hydration , 2004 .

[116]  D. Braga,et al.  Solid-state versus solution preparation of two crystal forms of [HN(CH2CH2)3NH][OOC(CH2)COOH]2. Polymorphs or hydrogen bond isomers? , 2004, Chemical communications.

[117]  Gautam R. Desiraju,et al.  The crystal as a supramolecular entity , 1996 .

[118]  Alexander J. Blake,et al.  Inorganic crystal engineering using self-assembly of tailored building-blocks , 1999 .

[119]  M. Zaworotko.  Crystal engineering of diamondoid networks , 1994 .

[120]  G. Rothenberg,et al.  Understanding solid/solid organic reactions. , 2001, Journal of the American Chemical Society.

[121]  Koichi Tanaka,et al.  Chiral inclusion crystallization of tetra(p-bromophenyl)ethylene by exposure to the vapor of achiral guest molecules: a novel racemic-to-chiral transformation through gas–solid reaction , 2000 .

[122]  Stuart R Batten,et al.  Interpenetrating Nets: Ordered, Periodic Entanglement. , 1998, Angewandte Chemie.

[123]  M. Caira,et al.  Zwitterionic nature of tenoxicam: crystal structures and thermal analyses of a polymorph of tenoxicam and a 1:1 tenoxicam:acetonitrile solvate. , 1995, Journal of pharmaceutical sciences.

[124]  Giannis S. Papaefstathiou and,et al.  An Inverted Metal-Organic Framework with Compartmentalized Cavities Constructed by Using an Organic Bridging Unit Derived from the Solid State , 2002 .

[125]  P. Anastas,et al.  Green Chemistry , 2018, Environmental Science.

[126]  M. Caira,et al.  Selective formation of hydrogen bonded cocrystals between a sulfonamide and aromatic carboxylic acids in the solid state , 1995 .

[127]  Gareth W. V. Cave,et al.  Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. , 2001, Chemical communications.

[128]  D. Braga,et al.  From Order to Disorder and Return: Remarkable Molecular and Crystal Dynamics in Solid [(C5H5)2Co][PF6] , 1996 .

[129]  Mark D. Hollingsworth.  Crystal Engineering: from Structure to Function , 2002, Science.

[130]  J. Fernández-bertran.  Mechanochemistry: an overview , 1999 .

[131]  Michael O'Keeffe,et al.  Hydrogen Storage in Microporous Metal-Organic Frameworks , 2003, Science.

[132]  R. Rastogi,et al.  Solid-State Reactions between Picric Acid and Naphthols , 1966 .

[133]  M. Caira,et al.  Crystalline Polymorphism of Organic Compounds , 1998 .

[134]  R. Rastogi,et al.  Solid-state reactivity of picric acid and substituted hydrocarbons , 1968 .

[135]  Yasuhiko Shirota,et al.  Photo- and electroactive amorphous molecular materials—molecular design, syntheses, reactions, properties, and applications , 2005 .

[136]  Margaret C. Etter,et al.  Hydrogen-bond formation in nitroanilines: the first step in designing acentric materials , 1987 .

[137]  I. Dance,et al.  Supramolecular Motifs: Concerted Multiple Phenyl Embraces between Ph4 P+ Cations Are Attractive and Ubiquitous. , 1996, Chemistry.

[138]  Gossage,et al.  Diagnostic organometallic and metallodendritic materials for SO2 gas detection: reversible binding of sulfur dioxide to arylplatinum(II) complexes , 2000, Chemistry.

[139]  M. Zaworotko,et al.  A 3D metal-organic network, [Cu2(glutarate)2(4,4'-bipyridine)], that exhibits single-crystal to single-crystal dehydration and rehydration. , 2003, Chemical communications.

[140]  P. Pongsawasdi,et al.  Formation of Inclusion Complexes between Cyclodextrins and Carbaryl and Characterization of the Complexes , 2002 .

[141]  Kumar Biradha,et al.  A springlike 3D-coordination network that shrinks or swells in a crystal-to-crystal manner upon guest removal or readsorption. , 2002, Angewandte Chemie.

[142]  D. Braga,et al.  Complementary hydrogen bonds and ionic interactions give access to the engineering of organometallic crystals , 1999 .

[143]  D. Braga,et al.  Reversible gas–solid reactions between the organometallic zwitterion [CoIII(η5-C5H4COOH)(η5-C5H4COO)] and vapours of difluoro- and chloro-acetic acids , 2003 .

[144]  Jean-Marie Lehn,et al.  Perspectives in Supramolecular Chemistry—From Molecular Recognition towards Molecular Information Processing and Self‐Organization , 1990 .

[145]  Masahiro Irie,et al.  Polymorphism of 1,2-Bis(2-methyl-5-p-methoxyphenyl-3-thienyl)perfluorocyclopentene and Photochromic Reactivity of the Single Crystals. , 2003, Chemistry.

[146]  M. Oh,et al.  Supramolecular metal-organometallic coordination networks based on quinonoid pi-complexes. , 2004, Accounts of chemical research.

[147]  Hoskins,et al.  Interdigitation, interpenetration and intercalation in layered cuprous tricyanomethanide derivatives , 2000, Chemistry.

[148]  D. Braga,et al.  Reactions between or within molecular crystals. , 2004, Angewandte Chemie.

[149]  Alexander J. Blake,et al.  ANION CONTROL IN BIPYRIDYLSILVER(I) NETWORKS : A HELICAL POLYMERIC ARRAY , 1997 .

[150]  A. P. Lötter,et al.  The interconversion of the polymorphic forms of chloramphenicol palmitate (CAP) as a function of environmental temperature , 1991 .

[151]  L. Nassimbeni.  Physicochemical aspects of host-guest compounds. , 2003, Accounts of chemical research.

[152]  S. Byrn.  Solid state chemistry of drugs , 1982 .

[153]  S. Barnett,et al.  Structural diversity of building-blocks in coordination framework synthesis: combining M(NO3)2 junctions and bipyridyl ligands , 2003 .

[154]  D. Braga,et al.  Reversible gas-solid reactions between the organometallic zwitterion [(η5-C5H4COOH)(η5-C5H4COO)CoIII] and vapors of trifluoroacetic and tetrafluoroboric acids , 2002 .

[155]  Davide M. Proserpio,et al.  POLYCATENATION, POLYTHREADING AND POLYKNOTTING IN COORDINATION NETWORK CHEMISTRY , 2003 .

[156]  Michael J. Zaworotko,et al.  Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? , 2004 .

[157]  I. Paul,et al.  Anisotropic reaction with ammonia gas of a crystal of a carboxylic acid with linear hydrogen-bonded chains. Example of unitropic attack , 1974 .

[158]  I. Paul,et al.  Reactions of Organ Crystals with Gases , 1975, Science.

[159]  S. Reutzel,et al.  Self-organization of adenine and thymine in the solid state , 1993 .

[160]  K. Miyanami,et al.  Quantitative evaluation of kneading and extrusion processes by pressure transmission characteristics of wet kneaded masses , 2001 .

[161]  D. Sandman,et al.  Diiminoisoindoline: tautomerism, conformations, and polymorphism. , 2004, Chemical communications.

[162]  Giannis S. Papaefstathiou,et al.  Inverted metal-organic frameworks: solid-state hosts with modular functionality , 2003 .

[163]  C. Janiak.  Functional Organic Analogues of Zeolites Based on Metal–Organic Coordination Frameworks , 1997 .

[164]  B. Abrahams,et al.  Assembly of porphyrin building blocks into network structures with large channels , 1994, Nature.

[165]  Guangming Li,et al.  Selective binding and removal of guests in a microporous metal–organic framework , 1995, Nature.

[166]  I. Paul,et al.  Reactions of molecular crystals with gases. I. Reactions of solid aromatic carboxylic acids and related compounds with ammonia and amines , 1974 .

[167]  Lee Brammer,et al.  Developments in inorganic crystal engineering. , 2004, Chemical Society reviews.

[168]  I. Dance,et al.  Contrasting crystal supramolecularity for [Fe(phen)3]I8 and [Mn(phen)3]I8: complementary orthogonality and complementary helicity , 2001 .

[169]  W. Jones,et al.  Mechanochemistry and co-crystal formation: effect of solvent on reaction kinetics. , 2002, Chemical communications.

[170]  M. Fujita,et al.  Metal-directed self-assembly of two- and three-dimensional synthetic receptors , 1998 .

[171]  D. Braga,et al.  Mechanochemical and solution preparation of the coordination polymers Ag[N(CH2CH2)3N]2[CH3COO]·5H2O and Zn[N(CH2CH2)3N]Cl2 , 2004 .

[172]  G. Kaupp,et al.  AFM IN ORGANIC SOLID STATE REACTIONS , 1996 .

[173]  F. Toda.  Crystal engineering for molecular dynamics , 2002 .