Ladder and web polymorphic forms of cocrystals of tetramethylpyrazinedioxide (TMPDO) and tetracyanoethylene (TCNE) are obtained by rapid or slow crystallization, respectively. In the thermodynamically less stable, purple (TMPDO)2− TCNE crystals the donor and acceptor building blocks are linked through N+O−°C(alkene) interactions to form one-dimensional ladders (see picture below).
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Greer et al. (1997) studied this question.
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