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Volume 69 
Part 11 
Page o1637  
November 2013  

Received 1 October 2013
Accepted 6 October 2013
Online 12 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.146
Data-to-parameter ratio = 17.7
Details
Open access

2,15-Dioxa-7,18,19,20,23-penta­aza­hepta­cyclo­[21.6.1.117,20.01,8.03,7.09,14.024,29]hentriaconta-9,11,13,17(31),18,24,26,28-octaen-30-one

aDepartment of Physics, Dr. M.G.R. Educational and Research Institute University, Periyar E.V.R. High Road, Adayalampattu, Chennai 600 095, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and dDepartment of Biotechnology, Dr. M.G.R. Educational and Research Institute University, Periyar E.V.R. High Road, Maduravoyal, Chennai 600 095, India
Correspondence e-mail: drdgayathri@gmail.com

In the title compound, C24H23N5O3, the oxindole ring system is nearly planar, with a dihedral angle between the two fused rings of 3.3 (1)°. In the fused pyrrolo-oxazole ring system, the oxazole and pyrrolidine rings adopt envelope conformations with the spiro C atom and one of the methyl­ene C atoms, respectively, as the flap atoms. In the crystal, mol­ecules are linked into a helical chain along the b axis via C-H...O inter­actions generating R21(7) and R22(8) ring motifs.

Related literature

For the biological activity of pyrrole, oxazole and indole derivatives, see: Fernandes et al. (2004[Fernandes, E., Costa, D., Toste, S. A., Lima, J. L. F. C. & Reis, S. (2004). Free Radical Biol. Med. 37, 1895-1905.]); Jiang et al. (2004[Jiang, S., Lu, H., Liu, S., Zhao, Q., He, Y. & Debnath, A. K. (2004). Antimicrob. Agents Chemother. 48, 4349-4359.]). For a related crystal structure, see: Narayanan et al. (2013[Narayanan, S., Srinivasan, T., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2013). Acta Cryst. E69, o23-o24.]).

[Scheme 1]

Experimental

Crystal data
  • C24H23N5O3

  • Mr = 429.47

  • Monoclinic, P 21 /c

  • a = 9.273 (5) Å

  • b = 10.983 (5) Å

  • c = 20.096 (5) Å

  • [beta] = 90.038 (5)°

  • V = 2046.7 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.653, Tmax = 0.746

  • 18864 measured reflections

  • 5113 independent reflections

  • 3845 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.146

  • S = 1.01

  • 5113 reflections

  • 289 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 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
C3-H3...O1i 0.93 2.45 3.311 (3) 154
C23-H23B...O2i 0.97 2.53 3.372 (3) 145
C24-H24B...O1i 0.97 2.31 3.209 (3) 153
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. 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 for Windows (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: IS5309 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India for the data collection. DV thanks the UGC (SAP-CAS) for the departmental facilities.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fernandes, E., Costa, D., Toste, S. A., Lima, J. L. F. C. & Reis, S. (2004). Free Radical Biol. Med. 37, 1895-1905.  [Web of Science] [CrossRef] [ChemPort]
Jiang, S., Lu, H., Liu, S., Zhao, Q., He, Y. & Debnath, A. K. (2004). Antimicrob. Agents Chemother. 48, 4349-4359.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Narayanan, S., Srinivasan, T., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2013). Acta Cryst. E69, o23-o24.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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, o1637  [ doi:10.1107/S1600536813027396 ]

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