Beyond stereochemistry associated with a central atom or bond, there are some types of stereochemistry that are dependent on the relationships between larger portions of a structure. These are fairly uncommon, and tend to be explained clearly in associated text when they are used, simply because they are so unusual.
Compounds with planar chirality have some portion of their structure that is planar or nearly so, where that portion is not symmetric with respect to rotation within its plane, and some other portion of the compound with fixed orientation relative to that plane. Most commonly that is accomplished by some sort of bridging configuration over the planar system in a way that prevents further rotation.
Compounds with planar chirality should be depicted in accordance with the earlier recommendations for the depiction of perspective structures. In planar chirality, the most important information is to distinguish the portions of the structure that are in the plane from those that are out of it. Typically, the planar portions are depicted as perpendicular to the plane of the paper, in which case they would include solid wedged bonds to indicate perspective. Alternatively, the planar portions may be depicted within the plane of the paper, in which case the portions connected directly to the planar parts would be indicated with solid wedged bonds.
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Helicenes are extended fused systems that are forced out of planarity when the fused system "loops back" on itself, forming a helical or screw-shaped figure in three dimensions. The non-planarity should be indicated by a pair of solid wedged bonds on one end of the helix separated, in even-membered rings, by another that is preferably depicted as bold and unwedged. It is additionally acceptable to display a corresponding pair of hashed wedged bonds on the other end of the helix. In no cases should solid wedged or hashed wedged bonds be present anywhere but at the termini of the helix.
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Molecular propellers consist of three or more rigid planar or mostly-planar systems connected to a central atom. In terms of depiction, they should be considered as extended analogs of hindered biaryls. The same recommendations made for biaryls would apply to propellers. Propellers should always be drawn with solid wedged and hashed wedged bonds within the rings and directly connected to the bonds about which they rotate. When one such bond in a ring is drawn as a solid wedged bond, it is preferable for the opposite bond also to be drawn as a solid wedged bond, and for any bonds between them to be drawn as bold unwedged bonds, but it is acceptable to leave those bonds as plain. The configuration of the propeller system should not solely be represented by solid wedged and hashed wedged bonds to other ring substituents that are distant from the rotatable bond.
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