Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 3 (March 2013)

organic compounds

Acta Cryst. (2013). E69, o435-o436    [ doi:10.1107/S160053681300490X ]

Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate

A. M. El-Agrody, A. M. Fouda, M. A. Al-Omar, A. E.-G. E. Amr, S. W. Ng and E. R. T. Tiekink

Abstract: In the title compound, C23H20BrNO4, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromo­benzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C-C-C-O = 3.4 (5)°]; the meth­oxy substituent is also coplanar [C-O-C-C = 174.5 (3)°]. In addition to an intra­molecular N-H...O(ester carbon­yl) hydrogen bond, the ester carbonyl O atom also forms an inter­molecular N-H...O hydrogen bond with the second amine H atom, generating a zigzag supra­molecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N-H...Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C-H...[pi] inter­actions.

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