Assigning R/S configuration
I have separated C1 and C3 into unique structures. For C1, it is clear that the oxygen of the hydroxyl group has the top priority while the methylene group has the lowest priority. A digraph is constructed such that we delineate two paths around each of the unsaturated rings. Thus, non-duplicate atoms C3 and C5 terminate with their respective duplicate atoms C(3) and C(5). The cyclopentene ring has locants in sphere 3 of {(7),7,H} which is a tie with {(4),4,H} in sphere 3 of the cyclopropene ring. But the locants {8,H,H} of the cyclopentene lose to {(3),3,H} of the cyclopropene ring. The priorities are O&gt;cyclopropene&gt;cyclopentene&gt;methylene. C1 has the (R)-configuration. continued...

A different digraph for C3 is constructed by dissecting the three rings into a total of six pathways, two for each ring. The rings are designated with red, blue and black dots. The red and blue rings take precedent over the black ring because each one has locants {O,O,H} at the branchs while the black ring has {O,C,H}. To distinguish between blue and red, we move to the next atoms on the chain. Blue has two oxygens while red has two carbons. The priorities are blue&gt;red&gt;black&gt;methylene. C3 has the (S)-configuration. 

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How to check for geometrical isomerism in cyclic compounds?
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