Four- and five-component molecular solids: crystal engineering strategies based on structural inequivalence

Mir, Niyaz A.; Dubey, Ritesh; Desiraju, Gautam R.

doi:10.1107/s2052252515023945

Cited by 60 publications

(59 citation statements)

References 33 publications

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“…14 The strategy was later shown to be a general one, using different components selected based on the same principles. [15][16][17] A great body of work on the preparation of ternary [18][19][20][21][22] and even quaternary 23,24 co-crystals has been recently reported by Desiraju and co-workers. First, a shapebased approach was devised, where one component in a binary co-crystal can be partially replaced by a third component, 25 in such a way that the molecules participating in (stronger) hydrogen bonding are left in place, while the weakly interacting molecules of the same kind are substituted by similarly shapes ones.…”

Section: Introductionmentioning

confidence: 99%

Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

2016

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ABSTRACT:A carefully designed strategy is presented for construction of ternary co-crystals, based on the orthogonality of two supramolecular interaction modes: hydrogen bonding between crown ethers and thioureas and the halogen bonding between thioureas and perfluorohalocarbons. Tested on a set comprising two crown ethers, two thioureas and five halogen bond donors, the strategy resulted in a high, 75% success rate, with 15/20 component combinations yielding at least one co-crystal. Crystal structure analysis revealed the interplay between the hydrogen and halogen bonding motifs, also shedding light on the variables affecting their formation.

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Section: Introductionmentioning

confidence: 99%

Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

2016

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“…40 The designed co-crystallization of multiple component crystals is akin to synthetic complexity in which the final outcome is difficult to predict. 44 In general, crystallization is a purification method because the phenomenon tends to be more excluding than including. Design strategies for ternary co-crystals rely on exploiting differences and complementarities in size, shape and functionality of the selected molecules.…”

Section: Introductionmentioning

confidence: 99%

Solid-state inclusion of C₆₀and C₇₀in a co-polymer induced by metal–ligand coordination of a Zn–porphyrin cage with a bis-pyridyl perylene derivative

et al. 2017

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“…π-Stacking in conjunction with hydrogen bonding was used for synthesis of ternary co-crystals [229,230]. Combination of H-bonded synthons and stacking interactions between donor and acceptor planar molecules allowed Desiraju and co-workers to synthesize quaternary and even quintinary co-crystals [231,232]. Partial substitution of some co-formers in quaternary systems with their shape-size analogs even allowed for obtaining six component solids [233].…”

Section: Co-crystals Designmentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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Four- and five-component molecular solids: crystal engineering strategies based on structural inequivalence

Abstract: A logic driven synthetic approach is used in this first report of the isolation of stoichiometric four-component molecular solids. A possible extension to a five-component solid is also described.

Cited by 60 publications

References 33 publications

Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Solid-state inclusion of C₆₀and C₇₀in a co-polymer induced by metal–ligand coordination of a Zn–porphyrin cage with a bis-pyridyl perylene derivative

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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Four- and five-component molecular solids: crystal engineering strategies based on structural inequivalence

Abstract: A logic driven synthetic approach is used in this first report of the isolation of stoichiometric four-component molecular solids. A possible extension to a five-component solid is also described.

Cited by 60 publications

References 33 publications

Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Systematic Construction of Ternary Cocrystals by Orthogonal and Robust Hydrogen and Halogen Bonds

Solid-state inclusion of C60and C70in a co-polymer induced by metal–ligand coordination of a Zn–porphyrin cage with a bis-pyridyl perylene derivative

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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Product

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Solid-state inclusion of C₆₀and C₇₀in a co-polymer induced by metal–ligand coordination of a Zn–porphyrin cage with a bis-pyridyl perylene derivative