Isostructurality in three-component crystals achieved by the combination of persistent hydrogen bonding motifs and solvent inclusion

Galcera, Judit; Friščić, Tomislav; Molins, Elı́es; Jones, William

doi:10.1039/c2ce26791h

Cited by 24 publications

(24 citation statements)

References 49 publications

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“…A phenomenon that arises from crystallization of chemically similar molecules, and one that is also known to be common for organic compounds and salts, is isostructurality (Galcera et al, 2013;Wood et al, 2012;Dabros et al, 2007;James et al, 2012). Factors such as the balance between 'closepacking effects' and more directional and anisotropic intermolecular interactions during crystallization (Aakerö y et al, 2010) play an important role in the engineering of isostructural crystals.…”

Section: Introductionmentioning

confidence: 99%

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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In order to investigate possible isostructural solid solutions of disubstituted N-phenylformamides and thioamides, we have studied the re-crystallization of pairs of compounds selected from 2,6-difluoro-N-phenylformamide (I), 2,6-dichloro-N-phenylformamide (II), 2,6-dimethyl-N-phenylformamide (III), 2,6-dichloro-N-phenylthioamide (IV), 2,6-dimethyl-N-phenylthioamide (V), 2,6-diisopropyl-N-phenylformamide (VI) and 2,6-diisopropyl-N-phenylthioamide (VII). For single-component 2,6-disubstituted-N-phenylformamides only the trans form occurs in the pure crystal, while for thioamides the cis form occurs, with only one exception. By forming solid solutions of pairs of these molecules the resulting structures all adopt similar N-H...O/S chains in the crystals. Solid solutions (1), (2) and (3), resulting from the mixing of (I) and (II), (II) and (III), and (IV) and (V), respectively, are all isostructural with each other (space group Pbca). Only co-crystal (1) is isostructural to both starting materials, while (2) is isostructural to only one of the starting pair, (II). Solid solution (3), which adopts the same Pbca structure as (1) and (2), is different to the monoclinic structures of both the reactants. Solid solution (4) is monoclinic, with similar hydrogen-bonded chains, and isostructural to the two components, resulting from the composition from the mixing of (VI) and (VII). Isostructural indices were used to quantify crystal-packing similarities and differences. Occupancy factors of the reactants in each co-crystal differ widely.

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Section: Introductionmentioning

confidence: 99%

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Omondi¹,

Lemmerer²,

Fernandes³

et al. 2013

Acta Crystallogr Sect B

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“…The following are available online, Table S1: Selected geometrical parameters describing water clusters stabilized in the structures of macrocyclic host molecules 1a, 1b, and 2; Figure S1: 1 H NMR (600 MHz) and 13 C NMR (150 MHz) spectra of macrocyclic host 2 in DMSO-d 6 ; Figure S2: 2D HSQC spectrum of compound 2 in DMSO-d 6 .…”

Section: Supplementary Materialsmentioning

confidence: 99%

“…Isostructurality is more likely to occur for multicomponent crystals [ 11 ], where only one of the components is changed. It can be seen for two-component host–guest inclusion compounds [ 12 ], as well as for three-component crystals [ 13 ]. Isostructurality induced by the solvent is also observed [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Stabilization of Near Identical Hydrogen Bonded Octameric Water Clusters in Crystal Structures of Three Distinct Non-Charged Polyamide Macrocyclic Host Molecules

2021

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In this paper, we present a comparative analysis of the solid state structures of three well-resolved hydrates of macrocyclic host molecules 1a, 1b, and 2 containing an intrannular amide-aryl substituent (lariat arm) connected to a fixed 26-membered ring in a normal (-NHCOAr, hosts 1a and 1b) or reverse manner (-CONHAr, host 2). Despite different chemical structures, these hosts crystallize as isostructural tetrahydrates in the same P-1 space group. Moreover, their crystals exhibit identical hydrogen bond motifs resulting in a stabilization of an almost identical unusual octameric water cluster built from the cyclic tetramer core and four water molecules, attached sequentially in an “up-and-down” manner. Further analysis reveals that, among the series, the structure of host 2 provides the most suitable environment for the accommodation of this type of water cluster.

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“…The comparison of crystal structures of hydrates of furosemide: Nicotinamide co-crystal suggests the mechanism of dehydration [108]. Galcera, et al demonstrated by using this tool that the isostructurality in co-crystals of lamotrigin with flexible dicarboxilic acids appears at the presence of solvents able to mimic the difference in conformation and volume of co-formers [109]. The analysis of 42 tyrammonium salts demonstrated that isostructural cation packing can occur even with structurally different anions, with different hydration states and with different hydrogen bonding; realization of different packing was associated with various conformations of the ethylammonium group of the cation [110].…”

Section: Crystal Packing Similarity Toolmentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

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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Isostructurality in three-component crystals achieved by the combination of persistent hydrogen bonding motifs and solvent inclusion

Abstract: Isostructurality in three-component crystals achieved by the combination of persistent hydrogen bonding motifs and solvent inclusion3

Cited by 24 publications

References 49 publications

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Formation of isostructural solid solutions in 2,6-disubstitutedN-phenylformamides andN-phenylthioamides

Stabilization of Near Identical Hydrogen Bonded Octameric Water Clusters in Crystal Structures of Three Distinct Non-Charged Polyamide Macrocyclic Host Molecules

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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