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The crystal structures and absolute stereochemistry of the (+/-)-racemic and (-)-enantiomeric hydrochlorides of 4-(4-bromophenyl)-2-methyl-1,2,3,4-tetrahydrolisoquinoline have been determined by single-crystal X-ray diffraction methods. Crystal data: I. (+/-)-(4RS)-4. monoclinic, P2(1)/n, a = 10.754(3), b = 11.271(2), c = 12.459(3) angstrom. Beta = 104.33(2)-degrees, Z = 4. R = 0.030 for 1921 reflections. II. (-)-(4R)-4, orthorhombic, P2(1)2(1)2(1), a = 10.988(2), b = 11.566(1), c = 11.892(2) angstrom. Z = 4, R = 0.035 for 1043 reflections. X-Ray intensity measurements of anomalously scattered reflections established the absolute configuration of the (-)-enantiomer to be 4R. Only small conformational differences between the two crystal forms examined were observed. The intramolecular bond lengths and angles have expected values, and the Br-phenyl planes, in both structures. are almost perpendicular to the isoquinoline ring. In the solid state there are no intermolecular hydrogen bonds except N-H...Cl salt bridge interactions, while the remaining intermolecular forces are of normal or weak van der Waals' character. In the crystal structure of the racemic form, the molecules are more closely packed than in the optically active 4R form. In both isomers the conformation of the piperidine ring is best described as a half-chair with the Br-phenyl group and N-methyl substituent equatorially positioned. The chiral hydrogen, H(4) and the N-methyl proton, H(2) are both axially oriented. Examination of the racemic and resolved isomers in the inhibition of stress-induced stomach ulcers reveals a high degree of enantiospecificity. The activity resides mainly in the S form.

acta chemica scandinavica/acta chemica scandinavica. b, organic chemistry and biochemistry/acta chemica scandinavica. a, physical and inorganic chemistry/acta chemica scandinavica. series b. organic chemistry and biochemistry/acta chemica scandinavica. series a, physical and inorganic chemistry

Resolution, Absolute Stereochemistry and Enantiospecificity of 4-(4-Bromophenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline. The Crystal and Molecular Structures of the Racemic and 4R-Enantiomeric Hydrochloride Salt Forms.