Received 23 July 2013
The title compound, C16H15N3O6, is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The six-membered carbocyclic ring adopts an envelope conformation with the central CH2 C atom as the flap. The amine N atom deviates from the mean plane of the pyran ring by 0.1365 (15) Å. The nitrophenyl ring is almost orthogonal to the pyran ring and the mean plane of the six-membered carbocyclic ring, the dihedral angle between their mean planes being 88.30 (7) and 87.61 (8)°, respectively. The molecular structure is stabilized by an intramolecular N-HO hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked via C-HO hydrogen bonds, forming infinite bands lying parallel to (-110) and composed of alternate R22(24) and R24(12) graph-set ring motifs. The crystal structure is further stabilized by C-H interactions, forming a three-dimensional structure.
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: Narayanan et al. (2013a,b). For graph-set notation, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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) and Mercury (Macrae et al., 2008); 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: SU2627 ).
The authors thank Mr T. Srinivasan and Dr D. Velmurugan, Head of the CAS in Crystallography and Biophysics, University of Madras, Chennai, India, for the data collection.
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