Received 4 May 2013
The title compound, C16H15ClN2O4, contains a chiral centre and crystallizes as a racemate. The methylene group -positioned to the carbonyl group is partially (21%) disordered. It flips to the opposite sides of the corresponding six-membered carbocycle by -0.304 (3) and 0.197 (11) Å, producing alternative envelope conformations. The planes of the pyran and chlorophenyl rings form a dihedral angle of 86.25 (9)°. The molecular structure is characterized by an intramolecular N-HO interaction, which generates an S(6) ring motif. The corresponding amino N atom deviates from the plane of the pyran ring by 0.1634 (19) Å. In the crystal, molecules are linked via C-HO hydrogen bonds, forming C(8) chains running parallel to the b-axis direction. The crystal structure also features C-H interactions.
For the uses and biological importance of chromene, see: Ercole et al. (2009); Geen et al. (1996) Khan et al. (2010); Raj et al. (2010). For related structures, see: Sun et al., (2012). For graph-set notation, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (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: LD2104 ).
PN and KS thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the X-ray intensity data collection.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Ercole, F., Davis, T. P. & Evans, R. A. (2009). Macromolecules, 42, 1500-1511.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Geen, G. R., Evans, J. M. & Vong, A. K. (1996). Comprehensive Heterocyclic Chemistry, 1st ed., edited by A. R. Katrizky, Vol. 3, pp. 469-500. New York: Pergamon.
Khan, K. M., Ambreen, N., Mughal, U. R., Jalil, S., Perveen, S. & Choudhary, M. I. (2010). Eur. J. Med. Chem. 45, 4058-4064.
Raj, T., Bhatia, R. K., Kapur, A., Sharma, M., Saxena, A. K. & Ishar, M. P. S. (2010). Eur. J. Med. Chem. 45, 790-794.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sun, R., Wang, K., Wu, D.-D., Huang, W. & Ou, Y.-B. (2012). Acta Cryst. E68, o824.