16-[(E)-Benzylidene]-13-hydroxy-4-methyl-2-phenyl-4,14-diazapentacyclo-[12.3.1.01,5.05,13.07,12]octadeca-7(12),8,10-triene-6,17-dione

In the title compound, C30H26N2O3, the two pyrrolidine rings adopt twisted and envelope conformations, whereas the cyclopentane ring adopts an envelope conformation. The least-squares planes through the pyrrolidine rings form a dihedral angle of 41.72 (10)°. The molecular structure is stabilized by an intramolecular O—H⋯N hydrogen bond, which generates an S(5) ring motif. Centrosymmetrically related molecules are linked via two pairs of intermolecular C—H⋯O interactions, forming R 2 2(16) ring motifs. In the crystal packing, the molecules are linked into two-dimensional networks parallel to the ab plane via C—H⋯O interactions.

[1]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[2]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[3]  R. Clark,et al.  The stereoselective synthesis of novel macrolide antibacterial agents via an intramolecular 1,3-dipolar cycloaddition of azomethine ylide , 2004 .

[4]  C. Pak,et al.  Facile transformation of 3,4-disubstituted 2-azetidinones to chiral 5,6-dihydro-2-pyridones , 2001 .

[5]  E. De Clercq,et al.  A conformational and structure-activity relationship study of cytotoxic 3,5-bis(arylidene)-4-piperidones and related N-acryloyl analogues. , 2001, Journal of medicinal chemistry.

[6]  F. Badria,et al.  Synthesis and biological evaluation of certain α, β-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents , 2000 .

[7]  K. Gothelf,et al.  Asymmetric 1,3-Dipolar Cycloaddition Reactions. , 1998, Chemical reviews.

[8]  Raymond E. Davis,et al.  Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals , 1995 .

[9]  G S Jacob,et al.  Aminosugar derivatives as potential anti-human immunodeficiency virus agents. , 1988, Proceedings of the National Academy of Sciences of the United States of America.

[10]  Olga Kennard,et al.  Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds , 1987 .

[11]  K. Matsui,et al.  Synthesis and alpha-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents. , 1986, Journal of medicinal chemistry.

[12]  A. M. Glazer,et al.  A nitrogen‐gas‐stream cryostat for general X‐ray diffraction studies , 1986 .

[13]  D. Cremer,et al.  General definition of ring puckering coordinates , 1975 .