Racemic compound against racemic conglomerate formation: the crystal properties of allylbenzylmethylphenylphosphonium iodide as compared with the nitrogen analogue.

Although racemic allylbenzylmethylphenylammonium iodide 1b displays spontaneous resolution crystallizing in a homochiral mode as a conglomerate, its phosphonium analogue rac-2b crystallizes in a heterochiral lattice forming racemic compound in the solid state. The more pronounced conformation freedom for 2b molecules manifests itself by multiple molecules crystallization (Z' = 3) of (S)-2b with the three independent molecules having different conformation.