Received 11 February 2010
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: email@example.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-HO interactions and the crystal packing is stabilized by weak C-H interactions.
For the biological activity of chromenopyrroles, see: Caine (1993); Tidey (1992); Carlson (1993); Sokoloff et al. (1990); Wilner (1985). For a related structure, see: Nirmala et al. (2009). For general background to the bridging of N-C bonds in pyrrolizine rings, see: Ramesh et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2258 ).
BG thanks AMET University management, India, for their kind support.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Caine, B. (1993). Science, 260, 1814-1816.
Carlson, J. (1993). Neur. Transm. 94, 11-19.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Nirmala, S., Kamala, E. T. S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, o1938.
Ramesh, P., Murugavel, S., SubbiahPandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4106-o4107.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Tidey, J. W. (1992). Behav. Pharm. 3, 553-566.
Wilner, P. (1985). Clinical Neuropharm. 18, Suppl. 1, 549-556.