The Crystal Packing of Organic Molecules: Challenge and Fascination Below 1000 Da

Gavezzotti, Angelo

doi:10.1080/08893119808035402

Cited by 88 publications

(59 citation statements)

References 113 publications

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“…This could mean that the CϪH···N motif forms less often than CϪH···O, [9] or merely that insufficient appropriate structures have been reported so far. Whatever the explanation, there is no question that the application of the CϪH···N synthon in crystal engineering has been limited and that currently it is a poor cousin relative to CϪH···O.…”

Section: Introductionmentioning

confidence: 99%

Crystal Engineering Involving C−H···N Weak Hydrogen Bonds: A Diquinoxaline Lattice Inclusion Host with a Preference for Polychlorocarbon Guests

et al. 2001

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The di(1,8-naphthryridine) 7 and diquinoxaline 12 derivatives were synthesised as potential new lattice inclusion hosts where strong hydrogen bonding interactions would be absent. A number of potential supramolecular synthons (such as aryl face-face, aryl edge-face, halogen-halogen, C−H···N, nitrogen-halogen) were expected to be accessible, with competing combinations of these weak attractions providing the best (but probably different) type of host-guest structure in each case. While the former compound turned out to be unstable, the latter proved to be a versatile host which preferred to trap small polychloroalkane guests. The X-ray structures of 12·(chloroform) 2 , (12) 2 ·(tetrahydrofuran), and

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Section: Introductionmentioning

confidence: 99%

Crystal Engineering Involving C−H···N Weak Hydrogen Bonds: A Diquinoxaline Lattice Inclusion Host with a Preference for Polychlorocarbon Guests

et al. 2001

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“…The key to a successful structure prediction is therefore the input of reliable molecular structures. mol [16] and that the experimentally observed structurewhere known -is indeed close to the global minimum. This suggests that phase space is thoroughly covered by the different search engines, but even the most elaborate and presumably accurate potentials often fail to give the experimental crystal structure always with the lowest lattice energy as would be expected for thermodynamic product control.…”

Section: Introductionmentioning

confidence: 96%

Racemic Compound FormationversusConglomerate Formation with [M(bpy)3](PF6)2 (M = Ni, Zn, Ru); Lattice Energy Minimisations and Implications for Structure Prediction

Breu

Domel

Norrby

2000

Eur. J. Inorg. Chem.

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Polymorphism observed with [M(bpy)3](PF6)2 (M = Ru, Ni, Zn) offers a unique opportunity to study the impact of different intermolecular packing motifs on lattice energies. Additionally, it allows us to test the accuracy of empirical intermolecular potentials, because these compounds represent an example of a system where a small change in molecular geometry already induces a qualitatively different crystal packing. Lattice energy minimisations for these three compounds applying both, rigid body and flexible body approaches, are reported. The calculations quite reasonably reproduce the crystallisation behaviour observed in this heteropolymorphic series. We conclude that the state‐of‐the‐art approach and all four tested empirical intermolecular potentials are adequate for these organometallic compounds. However, it is crucial to input the most accurate molecular structures. Molecular structures determined by X‐ray analysis need to be corrected for the apparent bond shrinkage due to librational motion. When these molecular structures are to be obtained by Molecular Mechanics or Quantum Mechanics methods the highest possible accuracy is required. Our results suggest that routine polymorph prediction may be more severely hampered by inaccuracies in molecular structures than by inadequacies in the intermolecular potentials. The key to a successful structure prediction is therefore the input of reliable molecular structures.

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“…This effect was described previously for several other compounds. 60,61 For α-glycine, atomic-force microscopy (AFM) experiments on the growth and dissolution of single crystals have shown that a lower limit to the step size on the (010) glycine face is close to the thickness of the hydrogen-bonded bilayer, that is the dissolution of α-glycine seems to proceed with preservation of dimers in solution. Diffraction data used together with the results of the in situ AFM measurements of glycine dissolution and growth in a complementary manner allow one to conclude that glycine leaves or docks to the crystal surface as cyclic hydrogen-bonded dimmers.…”

Section: Crystallization and Thermodynamic Studiesmentioning

confidence: 99%

Variable-temperature and variable-pressure studies of small-molecule organic crystals

Болдырева

Drebushchak

Шахтшнейдер³

et al. 2005

Arkivoc

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Dedicated to Professor Alexander I. Konovalov on the occasion of his AbstractSeveral examples of the comparative variable-temperature and variable-pressure studies of the small-molecule organic crystals are discussed. Selected systems represent the crystals with nonspherical flexible molecules / molecular fragments and with different types of intermolecular interactions, ranging from van der Waals interactions to hydrogen bonds of various types (OH…O, NH…OH, NH…O=C). A special attention is payed to the studies of solid drugs (polymorphs of paracetamol), amino acids (polymorphs of glycine, L-serine, D,L-serine), and dipeptides (glycilglycine and glycilglycine hydrate) by structural, spectroscopic and calorimetric techniques. The anisotropy of structural distortion within the range of stability of the same phase, as well as the phase transitions induced by changes in temperature or pressure are discussed.

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The Crystal Packing of Organic Molecules: Challenge and Fascination Below 1000 Da

Cited by 88 publications

References 113 publications

Crystal Engineering Involving C−H···N Weak Hydrogen Bonds: A Diquinoxaline Lattice Inclusion Host with a Preference for Polychlorocarbon Guests

Crystal Engineering Involving C−H···N Weak Hydrogen Bonds: A Diquinoxaline Lattice Inclusion Host with a Preference for Polychlorocarbon Guests

Racemic Compound FormationversusConglomerate Formation with [M(bpy)3](PF6)2 (M = Ni, Zn, Ru); Lattice Energy Minimisations and Implications for Structure Prediction

Variable-temperature and variable-pressure studies of small-molecule organic crystals

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