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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 [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.180
Data-to-parameter ratio = 19.9
Details
Open access

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

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-H...O 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[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.]); Araki et al. (2002[Araki, K., Suenaga, K., Sengoka, T. & Uemura, D. (2002). Tetrahedron, 58, 1983-1996.]). For a related structure, see: Nirmala et al. (2008[Nirmala, S., Murugan, R., Kamala, E. T. S., Sudha, L. & Sriman Narayanan, S. (2008). Acta Cryst. E64, o1774-o1775.]).

[Scheme 1]

Experimental

Crystal data
  • C26H31NO4

  • Mr = 421.52

  • Monoclinic, P 21 /c

  • a = 10.4784 (5) Å

  • b = 10.2624 (4) Å

  • c = 21.0937 (10) Å

  • [beta] = 95.350 (3)°

  • V = 2258.40 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.984

  • 20978 measured reflections

  • 5598 independent reflections

  • 3092 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.180

  • S = 1.02

  • 5598 reflections

  • 281 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C11-H11...O4i 0.93 2.60 3.419 (3) 148
C17-H17B...Cg4ii 0.97 2.97 3.817 (3) 146
C22-H22...Cg3iii 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Nirmala, S., Murugan, R., Kamala, E. T. S., Sudha, L. & Sriman Narayanan, S. (2008). Acta Cryst. E64, o1774-o1775.  [CSD] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o25  [ doi:10.1107/S1600536812049094 ]

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