Abstract
In the title spiro compound, C34H30N2O3, the central pyrrolidine ring is fused with the tetra-hydro-iso-quinoline ring, both having distorted envelope conformations, with the flap atoms being C and N, respectively. The meth-oxy-phenyl group is attached to the pyrrolidine ring, and is disordered over two positions, with refined occupancies of 0.638 (6):0.362 (6) Å. The central pyrrolidine ring is inclined relative to the tetra-hydro-iso-quinoline group, such that the dihedral between the non-flap atoms of each ring system is 11.29 (7)°. The spiro-linkage creates a dihedral angle of 83.26 (5)° between the indolinone ring and the non-flap atoms of the pyrrolidine ring. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds. For the major disorder component, these form C(11) chains that propagate parallel to the a axis.
Highlights
Janet Priyavathani Selvaraj,a Stella Mary,a Jyoti Boruah Dhruba,b,c Birkumar Singh Huidrom,d,c Yuvaraj Panneerselvamd,c and Kannan Piskala Subburamane*
In the title spiro compound, C34H30N2O3, the central pyrrolidine ring is fused with the tetrahydroisoquinoline ring, both having distorted envelope conformations, with the flap atoms being C and N, respectively
Molecules are linked via C— HÁ Á ÁO hydrogen bonds
Summary
Spiro frameworks are often utilized in drug design as a result of their three-dimensionality and structural diversity, which provide a framework for the attachment of pharmaceutically relevant active sites (Kobayashi et al, 1991). The spiro-pyrrolidine-indolin-2-one framework in particular is found in a number of alkaloids of biological significance (Hilton et al, 2000). Some of these compounds have been used as antimicrobial and antitumour agents (Sundar et al, 2011), or have analgesic (Crooks & Sommerville, 1982) and antiinfluenza properties (Stylianakis et al, 2003). The methoxyphenyl group is disordered over two orientations, with refined occupancies of 0.638 (6):0.362 (6). The disordered methoxyphenyl ring major (C27–C33/O3) and minor (C27D–C33D/O3D) components are largely planar, with the maximum deviations from their respective mean planes being observed for the methyl carbons, C33 [0.303 (7) A ] and C33D [0.130 (12) A ]
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