Chlordiazepoxide dichloro­methane monosolvate

In the title compound (systematic name: 7-chloro-2-methyl­amino-5-phenyl-3H-1,4-benzodiazepine 4-oxide dichloro­meth­ane monosolvate), C₁₆H₁₄ClN₃O·CH₂Cl₂, the seven-membered ring adopts a boat conformation with the CH₂ group as the prow and the two aromatic C atoms as the stern. The dihedral angle between the benzene rings is 75.25 (6)°. The crystal structure features centrosymmetric pairs of chlordiazepoxide mol­ecules linked by pairs of N—H...O hydrogen bonds, which generate R₂²(12) loops.

A hydrogen sulfate salt of chlordiazepoxide

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), C₁₆H₁₅ClN₃O⁺·HSO₄⁻, were obtained from a solution of chlordiazepoxide and sulfuric acid in methanol. The structure features chlordiazepoxide mol­ecules that are protonated at the imine N atom. The seven-membered ring adopts a boat conformation with the CH₂ 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 HSO₄⁻ 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 R₂²(10) loop. Each HSO₄⁻ anion connects two chlordiazepoxide moieties of the same chirality.