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Volume 69 
Part 7 
Page o1047  
July 2013  

Received 23 May 2013
Accepted 3 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 14.8
Details
Open access

6-(4-Methoxyphenyl)-6a-nitro-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, C29H27N3O5, the hydropyran ring adopts an envelope conformation with the methine C atom bearing the para-methoxybenzene ring as the flap. The central pyrrolidine ring has a twist conformation on the N-C bond involving the spiro C atom. The piperidine ring adopts a chair conformation. An intramolecular C-H...O contact closes an S(7) ring. In the crystal, inversion dimers linked by C-H...O interactions generate R22(18) loops and N-H...O hydrogen bonds connect the dimers into [100] chains.

Related literature

For a related structure and background to 4H-chromene derivatives, see: Devi et al. (2013[Devi, S. K., Srinivasan, T., Rao, J. N. S., Raghunathan, R. & Velmurugan, D. (2013). Acta Cryst. E69, o993.]).

[Scheme 1]

Experimental

Crystal data
  • C29H27N3O5

  • Mr = 497.54

  • Triclinic, [P \overline 1]

  • a = 9.3438 (3) Å

  • b = 11.3626 (4) Å

  • c = 13.5713 (4) Å

  • [alpha] = 68.687 (1)°

  • [beta] = 88.284 (1)°

  • [gamma] = 66.757 (1)°

  • V = 1222.49 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.982

  • 17765 measured reflections

  • 4964 independent reflections

  • 4116 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.119

  • S = 1.03

  • 4964 reflections

  • 335 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O3i 0.86 2.24 3.085 (2) 167
C14-H14...O5ii 0.93 2.54 3.358 (2) 147
C8-H8...O5 0.98 2.40 3.234 (2) 143
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+1, -z+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 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: HB7087 ).


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 thank the UGC (SAP-CAS) for the departmental facilties. SK also thanks DST PURSE for a Junior Research Fellowship and TS also thanks DST Inspire for a fellowship.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Devi, S. K., Srinivasan, T., Rao, J. N. S., Raghunathan, R. & Velmurugan, D. (2013). Acta Cryst. E69, o993.  [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [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, o1047  [ doi:10.1107/S1600536813015341 ]

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