A: Crystal structure of macrocycle 2. Its extended packing diagram (B) shows slipped columnar stacking of molecules of 2 (C), mediated by T-shaped interactions (D), as well as a combination of hydrogen bonding, fluoroarene-fluoroarene, and alkyne-alkyne [π···π] interactions (E).

Contexts in source publication

Context 1

... macrocycles arrange in a slipped stacking interaction in a way where two of the carbon atoms of the fluoroarene reside above the alkyne with a centroid-centroid distance of 3.29(3) Å, and two additional short arene-alkyne contacts of 3.37(3) Å; both are shorter than the sum of the van der Waals radii of two carbon atoms (3.40 Å). Macrocycle 2 (Figure 2A) crystalizes in the P 21/c space group with two molecules per unit cell. The dihedral angle between the planes of fluorinated and non-fluorinated rings is again very small (5.84 °) and the distance between the intraannular hydrogen atoms is 2.43(3) Å. ...

Context 2

... dihedral angle between the planes of fluorinated and non-fluorinated rings is again very small (5.84 °) and the distance between the intraannular hydrogen atoms is 2.43(3) Å. As seen in macrocycle 1, macrocycle 2 also forms a continuous columnar stack ( Figure 2B) with slipped stacking between the macrocycles ( Figure 2C) and T-shaped interactions ( Figure 2D). However, their closer inspection reveals an interaction different from that observed in 1: the molecules of 2 are not forming the stacking via the fluroarene-alkyne interaction but via fluroarenefluroarene and alkyne-alkyne interactions ( Figure 2E). ...

Context 3

... dihedral angle between the planes of fluorinated and non-fluorinated rings is again very small (5.84 °) and the distance between the intraannular hydrogen atoms is 2.43(3) Å. As seen in macrocycle 1, macrocycle 2 also forms a continuous columnar stack ( Figure 2B) with slipped stacking between the macrocycles ( Figure 2C) and T-shaped interactions ( Figure 2D). However, their closer inspection reveals an interaction different from that observed in 1: the molecules of 2 are not forming the stacking via the fluroarene-alkyne interaction but via fluroarenefluroarene and alkyne-alkyne interactions ( Figure 2E). ...

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... dihedral angle between the planes of fluorinated and non-fluorinated rings is again very small (5.84 °) and the distance between the intraannular hydrogen atoms is 2.43(3) Å. As seen in macrocycle 1, macrocycle 2 also forms a continuous columnar stack ( Figure 2B) with slipped stacking between the macrocycles ( Figure 2C) and T-shaped interactions ( Figure 2D). However, their closer inspection reveals an interaction different from that observed in 1: the molecules of 2 are not forming the stacking via the fluroarene-alkyne interaction but via fluroarenefluroarene and alkyne-alkyne interactions ( Figure 2E). ...

Context 5

... seen in macrocycle 1, macrocycle 2 also forms a continuous columnar stack ( Figure 2B) with slipped stacking between the macrocycles ( Figure 2C) and T-shaped interactions ( Figure 2D). However, their closer inspection reveals an interaction different from that observed in 1: the molecules of 2 are not forming the stacking via the fluroarene-alkyne interaction but via fluroarenefluroarene and alkyne-alkyne interactions ( Figure 2E). The two macrocycles are slipped in a way which results in the shortest contacts of 3.22(2) Å between the carbons of the fluoroarenes, and 3.32(2) Å between the carbons of alkynes. ...