Received 27 February 2013
aDepartment of Physics, Sree Krishna College of Engineering, Anicut, Vellore 632 001, India,bIndustrial Chemistry Labratory, Central Leather Research Institute, Adyar, Chennai 600 020, India,cDepartment of Physics, Mahendra Engineering College, Namakkal 637 503, India, and dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
Correspondence e-mail: firstname.lastname@example.org
In the title compound, C40H29N3O3S, the pyran ring adopts a sofa conformation, the thiazolidine ring adopts a twisted conformation and the pyrrolidine ring adopts an envelope conformation with the N atom as the flap. The pyrazole ring is essentially planar [maximum deviation = 0.002 (2) Å] and forms dihedral angles of 4.8 (1) and 39.0 (1)°, respectively, with the benzene rings attached to the N and C atoms. The acenapthylene ring system is approximately planar [maximum deviation = 0.058 (2) Å] and forms dihedral angles of 85.9 (1) and 48.5 (1)°, respectively, with the pyrollothiazole and chromene ring systems. The molecular conformation is stabilized by three weak intramolecular C-HO hydrogen bonds, which generate one S(8) and two S(6) ring motifs. In the crystal, pairs of C-HO hydrogen bonds link centrosymmetrically related molecules into dimers, generating R22(14) ring motifs. The crystal packing also features pairs of C-H interactions, which link the dimers into a supramolecular chain along the b axis.
For the biological properties of spiroheterocycles, see: Kilonda et al. (1995); Ferguson et al. (2005). For ring puckering parameters, see: Cremer & Pople (1975), and for asymmetry parameters, see: Duax et al. (1976). For related structures, see: Wei et al. (2012); Jagadeesan et al. (2013). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5201 ).
The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. L. Allinger, pp. 271-383. New York: John Wiley.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Ferguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature, 437, 209-214.
Jagadeesan, G., Sethusankar, K., Kathirvelan, D., Haribabu, J. & Reddy, B. S. R. (2013). Acta Cryst. E69, o317.
Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820-5824.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1265-o1266.