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Volume 66 
Part 4 
Pages o810-o811  
April 2010  

Received 11 February 2010
Accepted 1 March 2010
Online 13 March 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.063
wR = 0.201
Data-to-parameter ratio = 18.9
Details
Open access

Methyl 4-(4-chlorophenyl)-1,2,3,3a,4,4a,5,12c-octahydrobenzo[f]chromeno[3,4-b]pyrrolizine-4a-carboxylate

aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: crystallography2010@gmail.com

There are two molecules in the asymmetric unit of the title compound, C26H24ClNO3. The dihedral angles between the naphthalene ring system and the chlorophenyl substituent are 58.76 (9) and 51.59 (8)° in the two molecules. In the pyrrolizine ring system, both the pyrrolidine rings adopt envelope conformations and the dihydropyran rings adopt half-chair conformations. In the pyrrolizine ring system of one of the molecules, one of the C atoms is disordered over two positions with site occupancies of 0.69 (2) and 0.31 (2). The crystal packing is stabilized by weak intramolecular C-H...O interactions and the crystal packing is stabilized by weak C-H...[pi] interactions.

Related literature

For the biological activity of chromenopyrroles, see: Caine (1993[Caine, B. (1993). Science, 260, 1814-1816.]); Tidey (1992[Tidey, J. W. (1992). Behav. Pharm. 3, 553-566.]); Carlson (1993[Carlson, J. (1993). Neur. Transm. 94, 11-19.]); Sokoloff et al. (1990[Sokoloff, P., Giros, B., Martres, M. P., Bouthenet, M. L. & Schwartz, J. C. (1990). Nature (London), 347, 147-151.]); Wilner (1985[Wilner, P. (1985). Clinical Neuropharm. 18, Suppl. 1, 549-556.]). For a related structure, see: Nirmala et al. (2009[Nirmala, S., Kamala, E. T. S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, o1938.]). For general background to the bridging of N-C bonds in pyrrolizine rings, see: Ramesh et al. (2007[Ramesh, P., Murugavel, S., SubbiahPandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4106-o4107.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24ClNO3

  • Mr = 433.91

  • Monoclinic, P 21 /c

  • a = 22.3214 (9) Å

  • b = 10.8122 (5) Å

  • c = 18.5008 (8) Å

  • [beta] = 102.756 (3)°

  • V = 4354.8 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 295 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.960, Tmax = 0.960

  • 40734 measured reflections

  • 10819 independent reflections

  • 5771 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.201

  • S = 1.04

  • 10819 reflections

  • 571 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg5, Cg11 and Cg12 are the centroids of the C27-C31/C36, C1-C5/C10 and C5-C10 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C14-H14A...Cg12i 0.97 3.00 3.951 (2) 168
C16-H16A...Cg11i 0.97 2.83 3.706 (2) 151
C21-H21...Cg11ii 0.93 2.85 3.649 (2) 144
C26-H26B...Cg5iii 0.96 2.83 3.555 (1) 133
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+1, -z; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2258 ).


Acknowledgements

BG thanks AMET University management, India, for their kind support.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Caine, B. (1993). Science, 260, 1814-1816.  [CrossRef] [ChemPort] [PubMed] [ISI]
Carlson, J. (1993). Neur. Transm. 94, 11-19.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Nirmala, S., Kamala, E. T. S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, o1938.  [CSD] [CrossRef] [details]
Ramesh, P., Murugavel, S., SubbiahPandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4106-o4107.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sokoloff, P., Giros, B., Martres, M. P., Bouthenet, M. L. & Schwartz, J. C. (1990). Nature (London), 347, 147-151.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tidey, J. W. (1992). Behav. Pharm. 3, 553-566.  [ChemPort]
Wilner, P. (1985). Clinical Neuropharm. 18, Suppl. 1, 549-556.


Acta Cryst (2010). E66, o810-o811   [ doi:10.1107/S1600536810007804 ]

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