[Journal logo]

Volume 69 
Part 1 
Pages o23-o24  
January 2013  

Received 10 November 2012
Accepted 29 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.045
wR = 0.125
Data-to-parameter ratio = 17.6
Details
Open access

Ethyl 27-oxo-15-oxa-2,20-diazahexacyclo[18.6.1.01,8.02,6.09,14.021,26]heptacosa-9,11,13,21,23,25-hexaene-7-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, C27H30N2O4, the pyrrolidine ring adopts a twisted conformation. The indoline ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 81.7 (8)°. In the crystal, molecules are linked into centrosymmetric dimers with graph-set motif R22(16) via pairs of C-H...O hydrogen bonds. The terminal ethyl group of the ester group is disordered over two sets of sites, with a site-occupancy ratio of 0.587 (11):0.413 (11).

Related literature

For the biological activity of spiro-pyrrolidine derivatives, see: Obniska et al. (2003[Obniska, J., Pawlowski, M., Kolaczkowski, M., Czopek, A., Duszynska, B., Klodzinska, A., Tatarczynska, E. & Chojnacka-Wojcik, E. (2003). Pol. J. Pharmacol. 55, 553-557.]); Peddi et al. (2004[Peddi, S., Roth, B. L., Glennon, R. A. & Westkaemper, R. B. (2004). Bioorg. Med. Chem. Lett. 14, 2279-2283.]); Christoph et al. (2011[Christoph, W. Z., Jonathan, D. B., Zhong, L., Russell, G. D., Thomas, N., Mercy, O., Antonia, N., Jennifer, M. G., Hao, L., Judy, L., Frank, B., Erik, V., Andrea, O., Mark, J. & Jeremy, I. L. (2011). Bioorg. Med. Chem. Lett. 21, 4602-4607.]); Stylianakis et al. (2003[Stylianakis, I., Kolocouris, A., Kolocouris, N., Fytas, G., Foscolos, G. B., Padalko, E., Neyts, J. & De Clercq, E. (2003). Bioorg. Med. Chem. Lett. 13, 1699-1703.]); Waldmann (1995[Waldmann, H. (1995). Synlett, pp. 133-141.]); Suzuki et al. (1994[Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119-6122.]); Huryn et al. (1991[Huryn, D. M., Trost, B. M. & Fleming, I. (1991). C. Org. Synth. 1, 64-74.]). For a related structure, see: Ganesh et al. (2012[Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) and for asymmetry parameters, see: Nardelli et al. (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C27H30N2O4

  • Mr = 446.53

  • Triclinic, [P \overline 1]

  • a = 8.9327 (5) Å

  • b = 10.0068 (5) Å

  • c = 14.6379 (11) Å

  • [alpha] = 103.988 (4)°

  • [beta] = 95.023 (4)°

  • [gamma] = 113.775 (3)°

  • V = 1136.41 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 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 = 0.974, Tmax = 0.978

  • 20472 measured reflections

  • 5603 independent reflections

  • 4378 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.125

  • S = 1.08

  • 5603 reflections

  • 319 parameters

  • 40 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O1i 0.93 2.49 3.3957 (19) 164
C12-H12...O2ii 0.93 2.59 3.446 (2) 153
C13-H13...O4ii 0.93 2.47 3.3986 (17) 175
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y, z.

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: BT6853 ).


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

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Christoph, W. Z., Jonathan, D. B., Zhong, L., Russell, G. D., Thomas, N., Mercy, O., Antonia, N., Jennifer, M. G., Hao, L., Judy, L., Frank, B., Erik, V., Andrea, O., Mark, J. & Jeremy, I. L. (2011). Bioorg. Med. Chem. Lett. 21, 4602-4607.  [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.  [CSD] [CrossRef] [ChemPort] [details]
Huryn, D. M., Trost, B. M. & Fleming, I. (1991). C. Org. Synth. 1, 64-74.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Obniska, J., Pawlowski, M., Kolaczkowski, M., Czopek, A., Duszynska, B., Klodzinska, A., Tatarczynska, E. & Chojnacka-Wojcik, E. (2003). Pol. J. Pharmacol. 55, 553-557.  [PubMed] [ChemPort]
Peddi, S., Roth, B. L., Glennon, R. A. & Westkaemper, R. B. (2004). Bioorg. Med. Chem. Lett. 14, 2279-2283.  [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]
Stylianakis, I., Kolocouris, A., Kolocouris, N., Fytas, G., Foscolos, G. B., Padalko, E., Neyts, J. & De Clercq, E. (2003). Bioorg. Med. Chem. Lett. 13, 1699-1703.  [CrossRef] [PubMed] [ChemPort]
Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119-6122.  [CrossRef] [ChemPort] [ISI]
Waldmann, H. (1995). Synlett, pp. 133-141.  [CrossRef]


Acta Cryst (2013). E69, o23-o24   [ doi:10.1107/S1600536812049082 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.