Quantitative crystal structure analysis of 1,3,4-thiadiazole derivatives

Panini, Piyush; Mohan, T. P.; Gangwar, Usma; Sankolli, Ravish; Chopra, Deepak

doi:10.1039/c3ce40278a

Cited by 50 publications

(21 citation statements)

References 51 publications

(11 reference statements)

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“…solvent molecules or counter anions in gas phase. Similar deviation in corresponding dihedral angle values in crystal and optimised gas phase structure has been reported earlier …”

Section: Computational Studiessupporting

confidence: 86%

Metal Ion Directed Tautomeric Polymorphism in a Hydrazonamide/Hydrozonate System

Mandal

Patel

2017

ChemistrySelect

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Ortho and para-aminophenyl substituted hydrazonamide ligands viz. 2-amino-benzoic acid (amino-pyridin-2-ylmethylene)-hydrazide and 4-amino-benzoic acid (amino-pyridin-2-yl-methylene)-hydrazide) can exist in two tautomeric forms. The hydrazonamide (keto) form of the former ligand is only observed in free ligand, while its enolate form exists in some of its metal complexes. Both hydrazonamide and hydrazonate tautomers possess a six membered intramolecular hydrogen bond between the o-amino group and amide oxygen or imino nitrogen respectively. As a result, hydrazonamide and hydrazonate tautomeric forms exist in different molecular conformation and thus 'tautomeric polymorphism' is observed in this system. The evidence of tautomerism and consequent conformational change in metal complexes of 2-amino-benzoic acid (amino-pyridin-2-yl-methylene)-hydrazide is well supported by both DFT and NBO studies.

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“…solvent molecules or counter anions in gas phase. Similar deviation in corresponding dihedral angle values in crystal and optimised gas phase structure has been reported earlier …”

Section: Computational Studiessupporting

confidence: 86%

Metal Ion Directed Tautomeric Polymorphism in a Hydrazonamide/Hydrozonate System

Mandal

Patel

2017

ChemistrySelect

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“…For example, tetraphenylborates of N-salicylideneanilines form isostructural series of photochromic solids due to the packing of cations within a cavity formed by phenyl groups of anions, while more dense packing in other salts gives non-photochromic solids [86]. The effect of substituents on isostructurality of compounds was widely analyzed for both rigid [87][88][89][90][91][92] and flexible molecules [93][94][95][96][97][98]. Not only long-accepted isostructurality of Cl-and Me-or -Cl, -Br, and -I substituted molecules were revealed, but also the equivalence of ethylene and azo-bridges [92], or that of azide and iodide substituents [85] were demonstrated.…”

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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“…53,54 Thus, they reflect the directions and strength of intermolecular interactions within the crystal, mapped with different properties: the distance from the Hirshfeld surface to the nearest nucleus outside the surface (d e ), the corresponding distance to the nearest nucleus inside the surface (d i ) and a normalized contact distance (d norm ), shape index and curvedness (Figs 5 and S9 †). The 2D plots of d i vs d e map the quantitative contribution and relative strength (color coded) of different intermolecular interactions, occurring within the crystal structures (Figs S10 † and S11 †).…”

Section: The Hirshfeld Surfacesmentioning

confidence: 99%

“…44% for 2) (Figs 6, S10 † and S11 †) − which is characteristic for molecular crystals. 54 For 1 the O16-H16···O1W hydrogen bond between the acridinium cation and water molecule is represented by a single long spike (d i between 0.6 and 1.2) in the O···H and H···O fingerprint plots (Figs S10 † and S11 †). For 2 and 3 such spikes do not occur; however smaller spikes (d i values in the range of 1.1−1.6), indicating the presence of C−H···O hydrogen bonds among water molecules and CMA moieties or among CMA moieties themselves, are observed.…”

Section: The Hirshfeld Surfacesmentioning

confidence: 99%

Structure, formation, thermodynamics and interactions in 9-carboxy-10-methylacridinium-based molecular systems

et al. 2016

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Quantitative crystal structure analysis of 1,3,4-thiadiazole derivatives

Cited by 50 publications

References 51 publications

Metal Ion Directed Tautomeric Polymorphism in a Hydrazonamide/Hydrozonate System

Metal Ion Directed Tautomeric Polymorphism in a Hydrazonamide/Hydrozonate System

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Structure, formation, thermodynamics and interactions in 9-carboxy-10-methylacridinium-based molecular systems

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