Interplay of O–H⋯O, C–H⋯O and carbonyl–carbonyl interactions in crystal structures of o-benzoyl-l-tartaric acid and its anhydride

Madura, Izabela D.; Zachara, Janusz; Bernaś, Urszula; Hajmowicz, Halina; Kliś, Tomasz; Serwatowski, Janusz; Synoradzki, Ludwik

doi:10.1016/j.molstruc.2010.09.009

Cited by 11 publications

(3 citation statements)

References 42 publications

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“…Their oxygen atoms have relatively short contacts to the carboxylato carbon atoms. The O···C distance is, at 2.952(7) Å, shorter than the sum of the van der Waals radii (about 3.20 Å) and is in the characteristic range of supramolecular orthogonal dipole–dipole interactions. , Four further THF molecules were found in the cell, which have only van der Waals contacts to atoms of the macrocycle.…”

Section: Resultsmentioning

confidence: 94%

Gallium–Gallium Bonds As Effective Templates for the Generation of Macrocycles and Supramolecular Entities

et al. 2012

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Treatment of the tetraalkyldigallium(4) compound R 2 Ga−GaR 2 [1; R = CH(SiMe 3 ) 2 ] with the highly functionalized acids 3-and 4-carboxyphenylthiourea, 7azaindole-3-carboxylic acid, and 6-aminonicotinic acid afforded macrocyclic compounds in which two or four Ga−Ga bonds are bridged by the respective number of organic spacer ligands. In each reaction two equivalents of CH 2 (SiMe 3 ) 2 per formula unit of 1 were released. The Ga−Ga bonds of the products 2 to 5 are bridged by a carboxylato group and a chelating ligand containing two nitrogen donor atoms or the sulfur and nitrogen atoms of a thiourea group. The thiourea derivatives afforded different species with four or eight gallium atoms in the heterocycles (2 and 3) depending on their substitution patterns (1,3-versus 1,4-positions at the benzene rings). Supramolecular aggregates resulted that had up to 12 THF molecules encapsulated in the heterocycles or bonded to the surface of the molecules via hydrogen bonding or orthogonal dipolar interactions.

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Section: Resultsmentioning

confidence: 94%

Gallium–Gallium Bonds As Effective Templates for the Generation of Macrocycles and Supramolecular Entities

et al. 2012

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“…For crystal structures of R,R-tartaric mono amides, see: Rychlewska et al (1999); Rychlewska & Warżajtis (2000, 2001. For examples of the crystal structures of monoacyl derivatives, see: Madura et al (2010); Knyazev et al (1988); Chekhlov et al (1986); Ishihara et al (1993). For the synthesis, see: Bell (1987); Bernaś et al (2010).…”

Section: Related Literaturementioning

confidence: 99%

(2R,3R)-3-O-Benzoyl-N-benzyltartramide

Madura¹,

Zachara²,

Bernaś³

et al. 2012

Acta Cryst E

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The title compound, C18H17NO6 [systematic name: (2R,3R)-4-benzylamino-2-benzoyloxy-3-hydroxy-4-oxobutanoic acid], is the first structurally characterized unsymmetrical monoamide–monoacyl tartaric acid derivative. The molecule shows a staggered conformation around the tartramide Csp3—Csp3 bond with trans-oriented carboxyl and amide groups. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, molecules are linked by O—H⋯O hydrogen bonds between the carboxyl and amide carbonyl groups, forming translational chains along [001]. Further O—H⋯O and N—H⋯O hydrogen bonds as well as weaker C—H⋯O and C—H⋯π intermolecular interactions extend the supramolecular assembly into a double-layer structure parallel to (100). There are no directional interactions between the double layers.

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“…Hirshfeld surface [49][50][51][52][53][54] based tools represent a novel approach to this problem. The central element in this method is the derivation of the Hirshfeld surface-an immediately interpretable visualization of a molecule within its environment and the decomposition of this surface to provide a 'molecular fingerprint' -a directly accessible 2D map [49,[55][56][57][58] that provides the full distribution of interactions. The former, in addition to being an invaluable visualization tool, provides a basis for quantitative analysis of molecular properties for comparison with bulk measurement.…”

Section: Introductionmentioning

confidence: 99%

A dinuclear oxo-bridged Fe(III) complex with tris(2-pyridylmethyl) amine: Structure and Hirshfeld surface analysis

Seth

Mandal

Kar

et al. 2011

Journal of Molecular Structure

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Interplay of O–H⋯O, C–H⋯O and carbonyl–carbonyl interactions in crystal structures of o-benzoyl-l-tartaric acid and its anhydride

Cited by 11 publications

References 42 publications

Gallium–Gallium Bonds As Effective Templates for the Generation of Macrocycles and Supramolecular Entities

Gallium–Gallium Bonds As Effective Templates for the Generation of Macrocycles and Supramolecular Entities

(2R,3R)-3-O-Benzoyl-N-benzyltartramide

A dinuclear oxo-bridged Fe(III) complex with tris(2-pyridylmethyl) amine: Structure and Hirshfeld surface analysis

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