10.1021/acs.cgd.5b00168.s002 Christina A. Capacci-Daniel Christina A. Capacci-Daniel Cameron Mohammadi Cameron Mohammadi Jessica H. Urbelis Jessica H. Urbelis Katrina Heyrana Katrina Heyrana Natasha M. Khatri Natasha M. Khatri Marina A. Solomos Marina A. Solomos Jennifer A. Swift Jennifer A. Swift Structural Diversity in 1,3-Bis(<i>m</i>‑cyanophenyl)urea American Chemical Society 2015 growth solvents cocrystal phases urea crystal structures polymorph Structural Diversity latter morphology grain boundary migration title compound dimethyl sulfoxide bi supramolecular structures triphenylphosphine oxide mCyPU phosphine oxide functionalities 2015-05-06 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Structural_Diversity_in_1_3_Bis_i_m_i_cyanophenyl_urea/2169178 Hydrogen bonding between 1,3-bis ureas is a commonly used motif in the assembly of supramolecular structures such as gels, capsules and crystals. The title compound, 1,3-bis­(<i>m</i>-cyanophenyl)­urea (<b>mCyPU</b>), has previously been shown to crystallize in both an anhydrous and monohydrate phase (α and H–I). An expanded search for polymorphs and cocrystals of <b>mCyPU</b> revealed a much greater diversity of solid forms including three additional polymorphs (β, δ, ε), a second hydrate (H–II) and two cocrystal phases with dimethyl sulfoxide and triphenylphosphine oxide. Analysis of the single crystal structures obtained in this study shows that the typical 1-dimensional H-bonding between 1,3-bis urea groups is disrupted by the presence of other H-bond acceptors including cyano, water, sulfoxide and phosphine oxide functionalities. Re-examination of <b>α-mCyPU</b> additionally showed both blade and plate-like morphologies could be obtained from different growth solvents, with crystals of the latter morphology exhibiting a grain boundary migration prior to melting.