Versatile Inclusion Behaviour of a Dinitrocalix[4]arene Having Two Ester Pendants – Preparation and X-ray Crystal Structures of Complexes

Gruber, Tobias; Weber, Edwin; Seichter, Wilhelm; Bombicz, Petra; Csöregh, Ingeborg

doi:10.1080/10610270600847040

Cited by 13 publications

(15 citation statements)

References 16 publications

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“…There is an example (Fig. 9a) (Gruber et al, 2006) of a series of ester-substituted dinitro calixarene inclusion compounds where the host placements in the corresponding crystals are related by a virtual, non-crystallographic twofold rotation, retaining the space group P2 1 /n. Another example is a series of upper-rim-substituted lipophilic calix[4]arenes (Fig.…”

Section: From Isostructurality To Polymorphismmentioning

confidence: 99%

“…A series of laterally non-, mono-and disubstituted calixarenes (Fischer et al, 2007(Fischer et al, , 2011(Fischer et al, , 2012(Fischer et al, , 2013Gruner et al, 2010) presents an example. Different host-guest stoichiometry is realised depending on the guest recognition modes in the upper-rim dinitro-substituted and lower-rim ethyl-estersubstituted calix[4]arene molecules, crystallized from polar aprotic or protic solvents (Gruber et al, 2006). The intermolecular interactions affect the pinched-cone conformation of the host calixarene, which determines the accommodation of the guest molecules, optimizing electrostatic interactions (Fig.…”

Section: From Isostructurality To Polymorphismmentioning

confidence: 99%

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Supramolecular interactions in the solid state

Resnati

Boldyreva

Bombicz

et al. 2015

IUCrJ

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120

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In the last few decades, supramolecular chemistry has been at the forefront of chemical research, with the aim of understanding chemistry beyond the covalent bond. Since the long-range periodicity in crystals is a product of the directionally specific short-range intermolecular interactions that are responsible for molecular assembly, analysis of crystalline solids provides a primary means to investigate intermolecular interactions and recognition phenomena. This article discusses some areas of contemporary research involving supramolecular interactions in the solid state. The topics covered are: (1) an overview and historical review of halogen bonding; (2) exploring non-ambient conditions to investigate intermolecular interactions in crystals; (3) the role of intermolecular interactions in morphotropy, being the link between isostructurality and polymorphism; (4) strategic realisation of kinetic coordination polymers by exploiting multi-interactive linker molecules. The discussion touches upon many of the prerequisites for controlled preparation and characterization of crystalline materials.

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Section: From Isostructurality To Polymorphismmentioning

confidence: 99%

Section: From Isostructurality To Polymorphismmentioning

confidence: 99%

Supramolecular interactions in the solid state

Resnati

Boldyreva

Bombicz

et al. 2015

IUCrJ

Self Cite

120

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“…In the event of great similarity of the two unit cells, the value of p is close to zero [16]. For the calculation of the isostructurality index [I(s)], the distance differences between the crystal coordinates of identical non-H atoms within the same section of the related structures were used [14], taking into account both the differences in the geometry of the molecules and the positional differences caused by rotation and translation.…”

Section: Isostructural and Isometricity Calculationsmentioning

confidence: 99%

Comparative X-ray structural study of laterally mono-ethyl substituted 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-methoxycalix[4]arene and its non-substituted parent compound including guest free and solvated forms. Chemical straightening of guest channels

et al. 2011

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Comparative X-ray structural study of laterally mono-ethyl substituted 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetramethoxycalix[4]arene and its non-substituted parent compound including guest free and solvated forms.Abstract Three solvate crystal structures of the laterally ethyl substituted tetra-tert-butyltetramethoxycalix[4]arene 1 [(1ÁTHF (1a), 1ÁCHCl 3 (1b) and 1ÁCH 2 Cl 2 (1c)] are compared to the corresponding solvent-free structure (1) using single crystal X-ray structure determination, isostructurality and molecular isometricity calculations. To study the effect of the lateral substitution, the laterally nonsubstituted host with the guest THF (2a) is also included to the comparison. The calixarene molecules in the different structures all adopt the partial cone conformation with different affection of the respective guest molecules, always being positioned interstitially. Depending on the lateral substitution and the size of the included guests, the molecular conformation of the calix[4]arene shows small differences relating to the alignment of the arene units. The channels disposable of the solvent guest molecules in the crystal structures straighten as the effect of lateral substitution of the host calix[4]arene. The orthorhombic crystal structures of 1a-c are isostructural irrespective of the included solvent molecules, while 1 and 2a crystallise in the same monoclinic space group.

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“…Upper rim dinitro substituted and lower rim ethyl ester annexed calix[4αrene molecule was synthetised and crystallized from selected polar protic and aprotic solvents. Four inclusion crystals, containing acetone (1), DMF 2, DMSO (3) and n-BuOH (4) as guest, respectively, were investigated using X-ray diffraction on single crystals [1]. The co-crystals exhibit pronounced similarities, but also distinct differences.…”

Section: Isostructurality Of Co-crystals Of An Ester Substituted Dinimentioning

confidence: 99%

“…The organic salts have the following excellent advantages; i) robust supramolecular synthons are formed with charge-assisted hydrogen bonds, ii) a wide variety of cations or anions are able to be arranged on the clays by just changing combinations of the salts. In previous work, we showed the control of interlayer distance of organic clay mimic structures composed of 1-naphthylmethylammonium carboxylates [1] by just varying the carbon numbers of the n-alkanoate. The clays are formed with robust two-dimensional hydrogen bond network, and the anions between layers are arranged at invariable intervals.…”

mentioning

confidence: 99%

Tunable organic clay mimic structures with di(primary ammonium) dicarboxylates

Yuge

Miyata²,

Tohnai³

2006

Acta Cryst Sect A

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Keywords: small organic salts, crystal design, hydrogen bonds in organic crystalsDesign of supramolecular architectures as intended is one of the ultimate goals of supramolecular chemistry. To achieve the worthwhile goal, design of crystal structures are a promising approach because X-ray single crystallographic analysis is the only way for precise elucidation of molecular arrangements and intermolecular interactions at a molecular level. One of the approaches to design supramolecular architectures, organic salts is useful tool. The organic salts have the following excellent advantages; i) robust supramolecular synthons are formed with charge-assisted hydrogen bonds, ii) a wide variety of cations or anions are able to be arranged on the clays by just changing combinations of the salts. In previous work, we showed the control of interlayer distance of organic clay mimic structures composed of 1-naphthylmethylammonium carboxylates [1] by just varying the carbon numbers of the n-alkanoate. The clays are formed with robust two-dimensional hydrogen bond network, and the anions between layers are arranged at invariable intervals. Consequently, the clays have difficulties to control and vary intervals of molecules. Here we show the tunable organic clay mimic structures, which are designed and constructed with tert-amylammonium dicarboxylates [2]. The tunability takes important roles in association with various points: configurations of inclusion spaces, possibilities of topochemical reactions, solid-state physical properties, etc. The resulting structures give us a powerful and useful key to solve the conventional difficulties. To design the 2D motif with a tunable axle, a robust one-dimensional hydrogen bond network and tectons as a link are necessary. For this purpose, we adopted a robust supramolecular synthon composed of primary ammonium carboxylates. Many kinds of crystal structures composed of primary ammonium carboxylates have been analyzed and 287 salts are found in Cambridge Structural Database (CSD) (queried on components that contain at least two molecules, one primary amine and one carboxylic acid, except any other extra acids, bases and metals). And 173 (60.3%) of them form the specified one-dimensional hydrogen bond network with directionality. The same network formed when several types of dicarboxylic acids, such as terephthalic acid, biphenyl-4,4'-dicarboxylic acid and isophthalic acid, were employed as a tecton. X-ray analysis revealed that most of the organic salts formed the layer structures with interdigitated arrangements of primary ammonium cations. By varying the tecton, intervals of the cations on the layer and polarity of the layer are tunable. This design mentioned above is widely applicable to construct the predictable organic crystals.

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Versatile Inclusion Behaviour of a Dinitrocalix[4]arene Having Two Ester Pendants – Preparation and X-ray Crystal Structures of Complexes

Cited by 13 publications

References 16 publications

Supramolecular interactions in the solid state

Supramolecular interactions in the solid state

Comparative X-ray structural study of laterally mono-ethyl substituted 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-methoxycalix[4]arene and its non-substituted parent compound including guest free and solvated forms. Chemical straightening of guest channels

Tunable organic clay mimic structures with di(primary ammonium) dicarboxylates

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