Received 26 October 2012
In the title compound, C33H29NO4, the acenaphthylene ring system is essentially planar (r.m.s. deviation = 0.0290 Å). The pyrrolidine ring adopts a C-envelope conformation with a C atom displaced by 0.671 (2) Å from the mean-plane formed by the remaining ring atoms. The pyrrolidine ring is fused to acenaphthylene ring system making a dihedral angle of 88.0 (7)°. In the crystal, molecules are linked into R22(9) dimers via C-HN and C-HO hydrogen bonds. Two C atoms act as donors to the same O atom acceptor, resulting in the formation of R21(7) ring motifs. These two motifs combine to form hydrogen-bonded sheets running along the a- and b-axis directions.
For background to natural and synthetic pharmacologically active pyrrolidines, see: Waldmann (1995). For related structures, see: Augustine et al. (2010); Narayanan et al. (2012). For graph-set motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2602 ).
The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SN thanks the University Grant Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship under the SAP programme.
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