Do molecules with bridges through rings (in a manner illustrated by this) exist?



I sometimes get results like this when doing Energy Minimization on molview.org. For example: 



Is this actually a thing?

EDIT: As a slightly more realistic example, consider this: 



I'm not sure about the existence of molecules with bridges through rings. However, there are several publications of synthesis of molecules mimicking wheels and axles ([2]rotaxanes; The “[2]” refers to the number of interlocked components) as one shown below (Ref. 1): 


(The diagram is from Reference 1)

This specific molecule (8; an “impossible” [2]rotaxane) represents a macro-cycle with a straight-chain molecule with bulky end groups going through its center. The inclusion of two bulky end groups prevents the straight-chain molecule leaving the macro-cycle (mechanically interlocked) as depicted in the diagram (See Ref. 2 for the total synthesis of the molecule).

Note that Ref. 1 also cited articles for the synthesis of [2]catenanes, which contain two interlocked rings (instead of one axle and one macrocycle). Keep in mind that there are some advanced catenanes and rotaxanes that exist (e.g., [3]catenanes and [3]rotaxanes).


(The structures are from Reference 1)

References:


Edward A. Neal, Stephen M. Goldup, "Chemical consequences of mechanical bonding in catenanes and rotaxanes: isomerism, modification, catalysis and molecular machines for synthesis,"  Chem. Commun. 2014, 50(40), 5128-5142 (https://doi.org/10.1039/C3CC47842D).
Jeffrey S. Hannam, Stephen M. Lacy, David A. Leigh, Carlos G. Saiz, Alexandra M. Z. Slawin, Sheila G. Stitchell, "Controlled Submolecular Translational Motion in Synthesis: A Mechanically Interlocking Auxiliary,"  Angew. Chem., Intl. Fd. 2004, 43(25), 3260-3264 (https://doi.org/10.1002/anie.200353606).

