Systematic analysis of the probabilities of formation of bimolecular hydrogen-bonded ring motifs in organic crystal structures

Allen, Frank H.; Motherwell, W. D. S.; Raithby, Paul R.; Shields, Gregory P.; Taylor, Robin

doi:10.1039/a807212d

Cited by 337 publications

(117 citation statements)

References 28 publications

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“…However, formation of I is unlikely in competitive situations. Allen et al 61 determined the probability of formation of 75 bimolecular hydrogen bonded ring synthons in organic crystal structures. The probability of formation of I was found to be only 33%.…”

Section: How Are Co-crystals Designed?mentioning

confidence: 99%

Pharmaceutical Co-Crystals

Vishweshwar

McMahon

Bis

et al. 2006

Journal of Pharmaceutical Sciences

874

622

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Section: How Are Co-crystals Designed?mentioning

confidence: 99%

Pharmaceutical Co-Crystals

Vishweshwar

McMahon

Bis

et al. 2006

Journal of Pharmaceutical Sciences

874

622

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“…Allen et al found [21] that for structures containing any number of molecules, each possessing only one COOH group, probability of cyclic dimers formation is extremely high (ca. 95%), though a chain catemer motif is also possible.…”

Section: Resultsmentioning

confidence: 99%

Crystal structures of monohalogenated benzoic acids

2007

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Crystal structures resulting from a combination of different types of specific intermolecular interactions have been analysed using examples of 12 monohalogenated benzoic acids (HBA). These have been compared with structures known for corresponding monofunctional compounds, namely benzoic acid, fluorobenzene, chlorobenzene and iodobenzene. It is found that common for carboxylic acids centrosymmetric hydrogen-bonded dimers exist in all HBA, and at the same time a degree of halogen atoms aggregation is rather high in the most part of HBA, similarly to chlorobenzene and iodobenzene crystals. Previously reported tendency to increasing degree of Halaggregation in the sequence F < Cl £ Br £ I is confirmed. It is remarkable that a stacking motif of benzene rings is realised in all HBA crystals though it is absent in all considered monofunctional substances.

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“…molecules are connected by (O-H) 4 cycles of hydrogen bonds [7,8]. The geometrical parameters associated with the hydrogen bonds are given in The trans-cyclopentane-1,2-diol 5-trans was found to crystallize in the space group P-1 with two independent molecules in the unit cell (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In this regard, the directionality and strength associated with hydrogen bonds have been reliably exploited to control the molecular organization of molecules [2]. Indeed, a variety of association motifs/synthons [3] that occur reliably in the crystal packing have been identified for a variety of functional groups, [3,4] and search for new and novel motifs that decisively control the crystal packing continues to be of significant contemporary interest.…”

Section: Introductionmentioning

confidence: 99%

Self-assembly of cis- and trans-cyclic-1,2-diols. Supramolecular synthon equivalence between cis-1,2-diols and primary amides

Begum

Girija

Mallya

et al. 2005

Journal of Molecular Structure

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Inspite of the fact that the self-assembly of compounds containing hydroxyl group has been enormously documented in the literature, our studies with aliphatic cyclic diols have offered the unique opportunity to examine the self-assembly of gauche and anti forms of ethylene glycol. Whereas the cis-diols are found to form dimers that infinitely assemble further to yield tapes, the anti-diols are found to form linear chains that link up further to yield molecular tapes. Notably, both the isomers lead to molecular tapes, which have attracted immense attention since the inception of self-assembly for controlling molecular organization. Quite remarkably, the self-assembly observed with cisdiols establish a formal equivalence between supramolecular synthons associated with cis-1,2-diols and primary amides. Although the assembly of diols is akin to the tape structure adopted by primary amides, we prefer to view the association of diols as a ladder. The structures of 5-cis and 8-cis are both step-ladder assemblies. That formed by 5-trans is a new variant termed as rope-ladder assembly. The ring motifs observed in the crystal packing suggest for further scope in exploiting the polyhydroxyl compounds for self-assembly in a predictive manner. q

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Systematic analysis of the probabilities of formation of bimolecular hydrogen-bonded ring motifs in organic crystal structures

Cited by 337 publications

References 28 publications

Pharmaceutical Co-Crystals

Pharmaceutical Co-Crystals

Crystal structures of monohalogenated benzoic acids

Self-assembly of cis- and trans-cyclic-1,2-diols. Supramolecular synthon equivalence between cis-1,2-diols and primary amides

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