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The crystal structures of (3 S ,4a S ,8a S )-2-[(2 R ,3 S )-3-benzamido-2-benzo-yloxy-4-phenyl-but-yl]- N - tert -butyldeca-hydro-iso-quinoline-3-carboxamide, C 38 H 47 N 3 O 4 , (I), and (3 S ,4a S ,8a S )-2-[(2 R ,3 S )-3-(2,5-di-chloro-benzamido)-2-(2,5-di-chloro-benzo-yloxy)-4-phenyl-but-yl]- N - tert -butyldeca-hydro-iso-quinoline-3-carboxamide, C 38 H 43 Cl 4 N 3 O 4 , (II), are described. Despite their chemical similarity, they adopt different conformations in the solid state: (I) features a bifurcated intra-molecular N-H⋯(N,O) hydrogen bond from the tert -butylamide NH group to the piperidine N atom and the benzoate O atom, whereas (II) has an intra-molecular N-H⋯O link from the benzamide NH group to the tert -butyl-amide O atom. In the crystal of (I), mol-ecules are linked by C (4) amide N-H⋯O hydrogen bonds into chains propagating in the [010] direction, with both donor and acceptor parts of the benzamide group. In the extended structure of (II), C (11) N-H⋯O chains propagating in the [010] direction arise, with the donor being the tert -butylamide NH group and the acceptor being the O atom of the benzamide group.

acta crystallographica. section e, crystallographic communications

Different intra- and intermolecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzoyloxy)-4-phenylbutyl]-N-tert-butyldecahydroisoquinoline-3-carboxamides (X= H or Cl): compounds with moderate aspartyl protease inhibition activity