4′-Methyl-14′,19′-dioxa-4′-aza­spiro­[acenaphthyl­ene-1,5′-tetra­cyclo­[18.4.0.02,6.08,13]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(1H)-dione

Narayanan, S.; Srinivasan, T.; Purushothaman, S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812046144

Volume 68
Part 12
Page o3345
December 2012

Received 26 October 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.128
Data-to-parameter ratio = 18.4
Details

4'-Methyl-14',19'-dioxa-4'-azaspiro[acenaphthylene-1,5'-tetracyclo[18.4.0.0^2,6.0^8,13]tetracosane]-1'(24'),8',10',12',20',22'-hexaene-2,7'(1H)-dione

Sibi Narayanan,^a Thothadri Srinivasan,^a Santhanagopalan Purushothaman,^b Raghavachary Raghunathan ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

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.

Related literature

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).

Experimental

Crystal data

C₃₃H₂₉NO₄
M_r = 503.57
Monoclinic, P 2₁ /c
a = 11.248 (2) Å
b = 16.609 (3) Å
c = 14.037 (3) Å
= 92.965 (6)°
V = 2618.8 (9) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.979, T_max = 0.984
24740 measured reflections
6363 independent reflections
4183 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.128
S = 1.01
6363 reflections
345 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9N1ⁱ	0.93	2.62	3.535 (3)	167
C15-H15O1ⁱ	0.93	2.50	3.414 (2)	168
C27-H27BO2ⁱⁱ	0.97	2.48	3.403 (2)	158
C29-H29O2ⁱⁱ	0.93	2.57	3.450 (2)	159
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Acknowledgements

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.

References

Augustine, T., Vithiya, S. M., Ignacimuthu, S. & Ramkumar, V. (2010). Acta Cryst. E66, o3002.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Narayanan, S., Srinivasan, T., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o3345.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Waldmann, H. (1995). Synlett, pp. 133-141.