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M. Miyata and S. Tsuzuki
called benzo(c)phenanthrene (Fig. 7.18e) [39], which displays the same hierarchical
structure.
Thirdly, substituted aromatic compounds (orthorhombic, P2 1 2 1 2 1 ) are employed.
Phenanthridine [39] involves nitrogen at 6-position. The nitrogen functions for a
connection of 1D translation column through hydrogen bonds to form a preferential
2D layer, which is stacked with two-fold helix operation (Fig. 7.19e). In addition,
1,5-diiodonaphthalene [39] has iodine for halogen bonds (Fig. 7.19f). The translation
columns are combined by halogen bonds.
7.8 Conclusions and Perspectives
It has been found that supramolecular chirality of molecular assemblies in organic
crystals is attributable for position-dependent chirality. We designed a rectangular
triangle model attached with a molecule, enabling us to evaluate a position of organic
molecules through three kinds of rotations toward an axis. The combination of the
rotations leads us to four kinds of isomers with position-dependent chirality. The
isomers are combined through symmetry operations, including translation, twofold rotation, two-fold helix, and so on, to construct the corresponding molecular
assemblies with supramolecular chirality.
Z -matrix, which is used for the Gaussian program, enables us to describe such
a triangle model, leading to the evaluation of intermolecular interaction energies
between neighbored molecules in organic crystals. The resulting interaction energies
explain the hierarchical structures involving 1D columns, 2D layers, and 3D layerstacked crystals, prompting us to understand space group of crystals as well as chiral
crystallization of achiral molecules.
Dispersion energies contribute to such hierarchical structures. Basically, short
distances between neighbored molecules play a key role in determining the columns
and the layers. Hopefully, this research prompts us to elucidate the relation between
molecular structures and space group of crystals, to dissolve various hidden chirality
[37, 38], and to overcome diversity of organic compounds.
References
1. Hahn, T. (ed.): International Tables for Crystallography. Space-Group Symmetry, vol. A.
Kluwer Academic Publishers, London (1983, 1st edn.), (2002 5th edn.)
2. Dunitz, J.K., Gavezzotti, A.: How molecules stick together in organic crystals: weak
intermolecular interactions. Chem. Soc. Rev. 38, 2622 (2009)
3. Stone, A.J.: The Theory of Intermolecular Forces, 2nd edn. Oxford University Press, Oxford
(2013)
4. Beran, G.J.O., Nanda, K.: Predicting organic crystal lattice energies with chemical accuracy.
J. Phys. Chem. Lett. 1, 3480 (2010)
M. Miyata and S. Tsuzuki
called benzo(c)phenanthrene (Fig. 7.18e) [39], which displays the same hierarchical
structure.
Thirdly, substituted aromatic compounds (orthorhombic, P2 1 2 1 2 1 ) are employed.
Phenanthridine [39] involves nitrogen at 6-position. The nitrogen functions for a
connection of 1D translation column through hydrogen bonds to form a preferential
2D layer, which is stacked with two-fold helix operation (Fig. 7.19e). In addition,
1,5-diiodonaphthalene [39] has iodine for halogen bonds (Fig. 7.19f). The translation
columns are combined by halogen bonds.
7.8 Conclusions and Perspectives
It has been found that supramolecular chirality of molecular assemblies in organic
crystals is attributable for position-dependent chirality. We designed a rectangular
triangle model attached with a molecule, enabling us to evaluate a position of organic
molecules through three kinds of rotations toward an axis. The combination of the
rotations leads us to four kinds of isomers with position-dependent chirality. The
isomers are combined through symmetry operations, including translation, twofold rotation, two-fold helix, and so on, to construct the corresponding molecular
assemblies with supramolecular chirality.
Z -matrix, which is used for the Gaussian program, enables us to describe such
a triangle model, leading to the evaluation of intermolecular interaction energies
between neighbored molecules in organic crystals. The resulting interaction energies
explain the hierarchical structures involving 1D columns, 2D layers, and 3D layerstacked crystals, prompting us to understand space group of crystals as well as chiral
crystallization of achiral molecules.
Dispersion energies contribute to such hierarchical structures. Basically, short
distances between neighbored molecules play a key role in determining the columns
and the layers. Hopefully, this research prompts us to elucidate the relation between
molecular structures and space group of crystals, to dissolve various hidden chirality
[37, 38], and to overcome diversity of organic compounds.
References
1. Hahn, T. (ed.): International Tables for Crystallography. Space-Group Symmetry, vol. A.
Kluwer Academic Publishers, London (1983, 1st edn.), (2002 5th edn.)
2. Dunitz, J.K., Gavezzotti, A.: How molecules stick together in organic crystals: weak
intermolecular interactions. Chem. Soc. Rev. 38, 2622 (2009)
3. Stone, A.J.: The Theory of Intermolecular Forces, 2nd edn. Oxford University Press, Oxford
(2013)
4. Beran, G.J.O., Nanda, K.: Predicting organic crystal lattice energies with chemical accuracy.
J. Phys. Chem. Lett. 1, 3480 (2010)