Synthesis and crystal structure of ebastinium hydrogen fumarate.

The structure of ebastinium hydrogen fumarate {systematic name: 1-[4-(4-tert-butyl-phen-yl)-4-oxobut-yl]-4-(di-phenyl-meth-oxy)piperidin-1-ium (E)-3-carb-oxy-1-hy-droxy-prop-2-en-1-olate}, C(32)H(40)NO(2) (+)·C(4)H(3)O(4) (-), a 1:1 salt formed in the reaction between ebastine and fumaric acid is presented. All examined crystals were found to be twinned by pseudo-merohedry. The structure is extensively disordered, with over half (20 out of 35) its non-hydrogen atoms modelled as lying over two sets of sites. In the crystal, cation-anion pairs are linked by a strong N-H⋯O hydrogen bond [N⋯O = 2.697†(11)†à ]. These units inter-act via weaker C-H⋯O and C-H⋯π contacts to form layers lying parallel to the bc plane. The hydrogen fumarate anions are linked by a very short O-H⋯O hydrogen bond [O⋯O = 2.5402†(17)†à ], augmented by weak C-H⋯O contacts into pairs of R (2) (2)(6) ring motifs to form chains that extend parallel to the b-axis direction. Comparisons to similar crystal structures are presented.