Ethyl 8,13-dioxa-21-aza­penta­cyclo­[18.5.1.02,7.014,19.021,25]hexa­cosa-2(7),3,5,14,16,18-hexa­ene-26-carboxyl­ate

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

doi:10.1107/S1600536812049094

Volume 69
Part 1
Page o25
January 2013

Received 16 November 2012
Accepted 29 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.057
wR = 0.180
Data-to-parameter ratio = 19.9
Details

Ethyl 8,13-dioxa-21-azapentacyclo[18.5.1.0^2,7.0^14,19.0^21,25]hexacosa-2(7),3,5,14,16,18-hexaene-26-carboxylate

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, C₂₆H₃₁NO₄, the five-membered rings of the central pyrrolizine system adopt N-envelope conformations. The ethyl acetate group adopts an extended conformation. The dihedral angle between the benzene rings is 36.6 (1)°. In the crystal, C-HO hydrogen bonds form a zigzag chain running along the b-axis directions. The crystal structure is futher consolidated by C-H [pi] interactions.

Related literature

For the biological activity of pyrrolidine derivatives, see: Pinna et al. (2002); Araki et al. (2002). For a related structure, see: Nirmala et al. (2008).

Experimental

Crystal data

C₂₆H₃₁NO₄
M_r = 421.52
Monoclinic, P 2₁ /c
a = 10.4784 (5) Å
b = 10.2624 (4) Å
c = 21.0937 (10) Å
= 95.350 (3)°
V = 2258.40 (18) 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
20978 measured reflections
5598 independent reflections
3092 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.180
S = 1.02
5598 reflections
281 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C8-C13 and C18-C23 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C11-H11O4ⁱ	0.93	2.60	3.419 (3)	148
C17-H17BCg4ⁱⁱ	0.97	2.97	3.817 (3)	146
C22-H22Cg3ⁱⁱⁱ	0.93	2.94	3.770 (3)	150
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: PV2608 ).

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 Grants Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship under the SAP programme.

References

Araki, K., Suenaga, K., Sengoka, T. & Uemura, D. (2002). Tetrahedron, 58, 1983-1996.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Nirmala, S., Murugan, R., Kamala, E. T. S., Sudha, L. & Sriman Narayanan, S. (2008). Acta Cryst. E64, o1774-o1775.
Pinna, G. A., Pirisi, M. A., Chelucci, G., Mussinu, J. M., Murineddu, G., Loriga, G., DAquila, P. S. & Serra, G. (2002). Bioorg. Med. Chem. 10, 2485-2496.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.