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Published on: September 14, 2016
A hydrogen sulfate salt of chlordiazepoxide
Veronica Diesen1, Cláudio Lousada, Andreas Fischer
1Division of Applied Physical Chemistry, School of Chemical Science and Engineering, Royal Institute of Technology (KTH), 100 44 Stockholm, Sweden.
Abstract:
CRYSTALS OF THE HYDROGEN SULFATE SALT OF CHLORDIAZEPOXIDE (SYSTEMATIC NAME: 7-chloro-N-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-iminium 4-oxide hydrogen sulfate), C(16)H(15)ClN(3)O(+)·HSO(4) (-), were obtained from a solution of chlordiazepoxide and sulfuric acid in methanol. The structure features chlordiazepoxide mol-ecules that are protonated at the imine N atom. The seven-membered ring adopts a boat conformation with the CH(2) group as the prow and the two aryl C atoms as the stern. The dihedral angle between the benzene rings is 72.41 (6)°. In the crystal, the HSO(4) (-) anion acts as a bridging group between two chlordiazepoxide cations. The H atom of the protonated imino N forms an N-H⋯O hydrogen bond with a hydrogen sulfate ion. The anion in turn forms two hydrogen bonds, O-H⋯O with the anion as donor and N-H⋯O with the anion as acceptor, to generate an R(2) (2)(10) loop. Each HSO(4) (-) anion connects two chlordiazepoxide moieties of the same chirality.
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