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Volume 69 
Part 7 
Page o1130  
July 2013  

Received 7 May 2013
Accepted 6 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.153
Data-to-parameter ratio = 12.7
Details
Open access

Ethyl 4-(2-ethoxy-2-oxoethyl)-3-oxo-4,13-diazapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1,5(10),6,8,11,14(19),15,17,20-nonaene-12-carboxylate

aSchool of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, Jiangsu 221116, People's Republic of China
Correspondence e-mail: liu__yun3@sina.com

In the title compound, C26H22N2O5, the system consisting of five fused rings, being essentially planar with an r.m.s. deviation from the least-squares plane of 0.049 (3) Å, makes a dihedral angle of 58.72 (12)° with the plane of the ethyl carboxylate group immediately attached to it, and a dihedral angle of 89.48 (14)° with the plane of the ethyl carboxylate group attached via the -CH2- bridge. Bond lengths indicate [pi]-delocalization over the whole pentacyclic system. The molecular conformation is stabilized by a weak intramolecular C-H...O hydrogen bond. In the crystal, molecules form stacks along the b-axis direction, neighboring molecules within each stack being related by inversion and the shortest distance between the centroids of the pyridine rings within the stack being 3.667 (2) Å.

Related literature

For pharmaceutical properties of indolizines and related compounds, see: Olden et al. (1991[Olden, K., Breton, P., Grzegorzevski, K., Yasuda, Y., Gause, B. L., Oredipe, O. A., Newton, S. A. & White, S. L. (1991). Pharmacol. Ther. 50, 285-290.]); Jaffrezou et al. (1992[Jaffrezou, J. P., Levade, T., Thurneyssen, O., Chiron, M., Bordier, C., Attal, M., Chatelain, P. & Laurent, G. (1992). Cancer Res. 52, 1352-1359.]). For the preparation of annulated indolizine, see: Liu et al. (2010[Liu, Y., Hu, H.-Y., Zhang, Y., Hu, H.-W. & Xu, J.-H. (2010). Org. Biomol. Chem. 8, 4921-4926.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22N2O5

  • Mr = 442.46

  • Triclinic, [P \overline 1]

  • a = 8.4000 (17) Å

  • b = 11.008 (2) Å

  • c = 12.304 (3) Å

  • [alpha] = 74.33 (3)°

  • [beta] = 75.38 (3)°

  • [gamma] = 86.18 (3)°

  • V = 1060.0 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.977, Tmax = 0.981

  • 4095 measured reflections

  • 3811 independent reflections

  • 2855 reflections with I > 2[sigma](I)

  • Rint = 0.021

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.153

  • S = 1.01

  • 3809 reflections

  • 301 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O4 0.93 2.34 3.168 (3) 148

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL 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: YK2094 ).


Acknowledgements

The authors acknowledge financial support by 2012JSSPITP3193. This work was also sponsored by the research funds of Xuzhou City (XZZD1213 and XF10C015).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Jaffrezou, J. P., Levade, T., Thurneyssen, O., Chiron, M., Bordier, C., Attal, M., Chatelain, P. & Laurent, G. (1992). Cancer Res. 52, 1352-1359.  [PubMed] [ChemPort] [Web of Science]
Liu, Y., Hu, H.-Y., Zhang, Y., Hu, H.-W. & Xu, J.-H. (2010). Org. Biomol. Chem. 8, 4921-4926.  [CrossRef] [ChemPort] [PubMed]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Olden, K., Breton, P., Grzegorzevski, K., Yasuda, Y., Gause, B. L., Oredipe, O. A., Newton, S. A. & White, S. L. (1991). Pharmacol. Ther. 50, 285-290.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1130  [ doi:10.1107/S1600536813015833 ]

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