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Tri­benzyl­phosphane, PBz3 (C21H21P), crystallizes in a notably different unit cell to its Group 15 analogues NBz3 and SbBz3. The packing is dominated by face-edge [pi]-inter­actions which result in infinite columns of mol­ecules parallel to the b axis; these columns are linked by further face-edge [pi]-inter­actions into sheets of columns parallel to the [101] direction. Its hydro­chloride salt, tri­benzyl­phospho­nium hydrogen di­chlo­ride-tri­benzyl­phosphane (1/1), lies on a threefold axis within a trigonal crystal system. It exists in the solid state as a hydrogen-bridged dimer with the composition [H(PBz3)2]+[HCl2]- (C42H43P2+·HCl2-). The cation is the first structurally authenticated example of a phosphane acting as a hydrogen-bond acceptor to a phospho­nium group and the cations are linked into a three-dimensional network through inter­molecular face-edge [pi]-inter­actions.
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