Received 4 May 2013
In the title compound, C16H15BrN2O4, the six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation with the disordered methylene C atom as the flap. The pyran ring is almost orthogonal to the chlorophenyl ring, making a dihedral angle of 87.11 (12)°. The amine-group N atom deviates significantly from the pyran ring [0.238 (3) Å]. 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, which generate C(8) chains running parallel to the b axis. The chains are linked by C-H interactions. The methylene-group C atom of the chromene system that is disordered, along with its attached H atoms and the H atoms on the two adjacent C atoms, has an occupancy ratio of 0.791 (7):0.209 (7).
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 a related structure, see: Sun et al. (2012). For graph-set notation, see: Bernstein et al. (1995).
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); 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: SU2597 ).
PN and KS thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the X-ray intensity data collection.
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