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Volume 69 
Part 6 
Page o993  
June 2013  

Received 18 May 2013
Accepted 21 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.127
Data-to-parameter ratio = 18.4
Details
Open access

6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octahydrospiro[chromeno[3,4-a]indolizine-12,3'-indolin]-2'-one

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, C28H25N3O4, the central pyrrolidine ring adopts adopts an envelope conformation with the N atom as the flap and the piperidine ring adopts a chair conformation. The pendant pyrrolidine ring is almost planar (r.m.s. deviation = 0.008 Å). An intramolecular C-H...O interaction closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H...O hydrogen bonds generate R22(8) loops.

Related literature

For biological background to 4H-chromene derivatives, see: Cai (2008[Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.]); Valenti et al. (1993[Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.]). For applications of indoline-2-one and its derivatives as precursors in the synthesis of pharmaceuticals, see: Colgan et al. (1996[Colgan, S. T., Haggan, G. R. & Reed, R. H. (1996). J. Pharm. Biomed. Anal. 14, 825-833.]).

[Scheme 1]

Experimental

Crystal data
  • C28H25N3O4

  • Mr = 467.51

  • Monoclinic, C 2/c

  • a = 23.2940 (13) Å

  • b = 11.2517 (7) Å

  • c = 19.7702 (10) Å

  • [beta] = 112.659 (3)°

  • V = 4781.8 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.983

  • 20735 measured reflections

  • 5804 independent reflections

  • 3892 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.127

  • S = 1.00

  • 5804 reflections

  • 316 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 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
C16-H16...O4 0.98 2.50 3.1394 (18) 123
N3-H3A...O4i 0.86 1.97 2.8218 (17) 168
Symmetry code: (i) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1].

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 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: HB7084 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SK,TS and DV acknowledge the UGC (SAP-CAS) for the departmental facilties. SK thanks DST PURSE for a Junior Research fellowship and TS thanks DST Inspire for a fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.  [PubMed]
Colgan, S. T., Haggan, G. R. & Reed, R. H. (1996). J. Pharm. Biomed. Anal. 14, 825-833.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.  [ChemPort] [PubMed]


Acta Cryst (2013). E69, o993  [ doi:10.1107/S1600536813014062 ]

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