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Many sources including previous answers on Stack Exchange claim that it is antiaromatic.

But in a different yet similar question, I have also seen people saying that a monocyclic ring with 7 or more members can go out of plane to avoid antiaromaticity and become non-aromatic.

Shouldn't the same rule apply here as well?

Links mentioned: https://chemistry.stackexchange.com/a/102606/74312

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  • $\begingroup$ That is the general meaning of antiaromaticity. It is never enough stressed out that it is a hypothetical structure generally stabilised by the system arranging differently! $\endgroup$
    – Alchimista
    Commented Oct 21, 2019 at 10:09
  • $\begingroup$ Food for thought and not a full answer: the big difference between oxepin and the cycloheptatrienyl anion is that the latter is charged so the molecule needs to strike a balance between structural changes to avoid conjugation and delocalisation of the negative charge. $\endgroup$
    – Jan
    Commented Oct 21, 2019 at 13:01

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