An x-ray diffraction structural investigation of organic complexone ligands. XVI. Crystal and molecular structure of the dihydro-chloride salts of ethylene-diamine-N,N?-Di-3-propionic and ethylenediamine-N,N,N?,N?-tetra-3-propionic acids and the monohydrobromide salt of ethylenediamine-N,N,N?,N?-tetraacetic acid monohydrate

Shkol'nikova, L. M.; Suyarov, K. D.; Gasparyan, A. V.; Poznyak, A. L.; Zavodnik, V. E.; Dyatlova, N. M.

doi:10.1007/bf00752795

Cited by 3 publications

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“…The P1 mimics VEYXAY (Shkol'nikova et al, 1989) and VIHTUD (Gerber & Betz, 2013;Fig. 9) are very interesting 1:1:1 hydrated salts of a small counterion.…”

Section: Approximate Symmetry Is Common In Z = 1 Structures Of Molecu...mentioning

confidence: 99%

Pervasive approximate periodic symmetry in organic P1 structures

Brock

2022

Acta Crystallogr Sect B

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The goal of this project was to identify the prevalence of approximate symmetry in organic P1 structures. In the November 2019 version of the Cambridge Structural Database (CSD), there are 2592 organic, P1, R ≤ 0.050 structures; complete, unique entries are available for 1407 Z = Z′ > 1 and 1049 Z = Z′ = 1 structures. All the Z > 1 structures can have approximate symmetry; the Z = 1 structures were scanned to find those composed of molecules or ions that might lie on a special position and those that have two or more large molecules or ions that are very similar. The number of Z = 1 structures so identified was 285, of which 49 were grouped with the Z > 1 structures because Z effective > 1. The packing in each of the 1407 + 285 = 1692 structures was investigated. The 144 that should almost certainly have been described in a smaller or higher-symmetry unit cell were removed from the list; 120 of the 144 are composed of achiral or racemic material. (About half of the Z = 1 and 89% of the Z > 1 structures are composed of enantiopure material.) Approximate periodic symmetry was found in 86% of the 1337 remaining Z > 1 structures and in 72% of the 211 remaining Z = 1 structures. About a third of the enantiomerically pure structures mimic inversion symmetry; 38% have approximate rotational symmetry. For the structures of achiral and racemic material, distorted glide or mirror symmetry is more common than is distorted inversion symmetry. Approximate rotational and glide symmetry was found to be periodic in two dimensions considerably more often than in three. In 4% of the structures, different layer types alternate or layers are related by approximate local rotations, as well as by small translations. In 5% of the structures, different parts of the molecule are segregated into two-dimensional regions that have different approximate symmetries. More than a third of the structures that are a distorted version of a higher-symmetry structure were determined at T ≥ 288 K.

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“…The P1 mimics VEYXAY (Shkol'nikova et al, 1989) and VIHTUD (Gerber & Betz, 2013;Fig. 9) are very interesting 1:1:1 hydrated salts of a small counterion.…”

Section: Approximate Symmetry Is Common In Z = 1 Structures Of Molecu...mentioning

confidence: 99%

Pervasive approximate periodic symmetry in organic P1 structures

Brock

2022

Acta Crystallogr Sect B

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Crystal and molecular structure of the “asymmetric” ethylenediamine-N,N-di-3-propionic acid monohydrate

2013

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Analysis of Specialties of Crystal Structure for Non-chelate Conformations of Ethylene-Diaminetetraacetic Acid and Its Salts With Alkali and Alkaline Earth Metals

Noguchi

2022

Ukr. Chem. Journ.

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In the present study, the crystal structures of non-chelating EDTA molecules and their non-chelation salts in a zwitterionic state, along with the EDTA-chelates of alkali and alkaline earth metals, were searched and overviewed. 25 non-chelating molecules of EDTA, and zwitterions of ethylenediammonium-diacetate diacetic acid HOOC-CH2-(-OOC-CH2-)NH+-CH2-CH2-NH+(-CH2-COO-)-CH2-COOH and their salts (ethylenediammonium-tetraacetic acid (HOOC-CH2-)2NH+-CH2-CH2-NH+(-CH2-COOH)2, ethylenediammonium-acetate triacetic acid (HOOC-CH2-)2NH+-CH2-CH2-NH+(-CH2-COO-)-CH2-COOH, and ethylenediammonium-tetraacetate (-OOC-CH2-)2NH+-CH2-CH2-NH+(-CH2-COO-)2 with counterions), as well as 17 types of EDTA-chelates of alkali metal ions (Li+, Na+, K+, Rb+) and alkaline earth metal ions (Mg2+, Ca2+, Sr2+, Ba2+) were analyzed using data from the Cambridge Crystallographic Data Center (CCDC). Each intramolecular contact distance between nitrogen and oxygen atoms (NH+···O) has been examined and found to be around 2.7 Å. Investigation on the distribution of the intramolecular NH+··· NH+-distances of EDTA and non-chelated salts thereof also revealed that bulky counterion and certain crystal solvent molecules correspond to change in crystal packing, and that they influenced the conformers of EDTA molecules among gauche form to anti form. In the existing crystalline EDTA-chelates of alkali metals as well as alkaline earth metals, various coordination numbers (CN) and the denticity (к) of EDTA anions are displayed; CN 5 to 9, and tri- and hexadentate fashions. Intramolecular contact N···O and N···N distances correspond to the metal ion radii except for the case of Sr-EDTA chelate, probably due to differences of crystal packings in addition to the number of counterions and crystal solvent molecules. The existing data on crystalline EDTA and its salts have been gathered herein, which contributes to a further understanding and exploring applications hereafter.

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Cited by 3 publications

References 8 publications

Pervasive approximate periodic symmetry in organic P1 structures

Pervasive approximate periodic symmetry in organic P1 structures

Crystal and molecular structure of the “asymmetric” ethylenediamine-N,N-di-3-propionic acid monohydrate

Analysis of Specialties of Crystal Structure for Non-chelate Conformations of Ethylene-Diaminetetraacetic Acid and Its Salts With Alkali and Alkaline Earth Metals

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Cited by 3 publications

References 8 publications

Pervasive approximate periodic symmetry in organic P1 structures

Pervasive approximate periodic symmetry in organic P1 structures

Crystal and molecular structure of the “asymmetric” ethylenediamine-N,N-di-3-propionic acid monohydrate

Analysis of Specialties of Crystal Structure for Non-­chelate Conformations of Ethylene-Diaminetetraacetic Acid and Its Salts With Alkali and Alkaline Earth Metals

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Analysis of Specialties of Crystal Structure for Non-chelate Conformations of Ethylene-Diaminetetraacetic Acid and Its Salts With Alkali and Alkaline Earth Metals