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Two tetrahydocarbazolone derivatives were found to show multiple unsolvated crystal forms. A persistent dimer motif was detected in solution by FTIR spectroscopy that is maintained in the kinetic crystal forms. Rationally introduced steric bulk induces the formation of a more stable catemeric form.

Graphical abstract: Conserved hydrogen bonding in tetrahydrocarbazolone derivatives: influence of solution-state assembly on crystal form nucleation

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