Unknown

Dataset Information

0

Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity.


ABSTRACT: The crystal structures of (3S,4aS,8aS)-2-[(2R,3S)-3-benzamido-2-benzo-yloxy-4-phenyl-but-yl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamide, C38H47N3O4, (I), and (3S,4aS,8aS)-2-[(2R,3S)-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, C38H43Cl4N3O4, (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.

SUBMITTER: Cunico W 

PROVIDER: S-EPMC5458323 | BioStudies | 2017-01-01T00:00:00Z

REPOSITORIES: biostudies

Similar Datasets

2017-01-01 | S-EPMC5676560 | BioStudies
2012-01-01 | S-EPMC3374372 | BioStudies
1000-01-01 | S-EPMC3414995 | BioStudies
2015-01-01 | S-EPMC4532559 | BioStudies
2010-01-01 | S-EPMC2979673 | BioStudies
1000-01-01 | S-EPMC3009098 | BioStudies
2011-01-01 | S-EPMC3100015 | BioStudies
2011-01-01 | S-EPMC6264379 | BioStudies
2012-01-01 | S-EPMC3515274 | BioStudies
2020-01-01 | S-EPMC7321179 | BioStudies