SYNTHESIS AND X-RAY STRUCTURE OF 2-AMINO-4-(4-FLUOROPHENYL)-7,7-DIMETHYL-5-OXO-5,6,7,8-TETRAHYDRO-4H-CHROMENE-3-CARBONITRILE

The title compound, 2-amino-4-(4-fluorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (C21 H24 F N3 O3), crystallizes in the monoclinic space group C 2/c with unit cell parameters: a =31.342(3), b = 9.3481(9), c = 15.9051(11) Ǻ, β = 118.687(9)º, Z = 8. The crystal structure was solved by direct methods and refined by full-matrix least-squares procedures to a final R-value of 0.0588 for 2776 observed reflections. The fused cyclohexene and pyran rings adopt sofa and boat conformations, respectively. The four essentially planar atoms (C1/ C2/C5/C6) of pyran ring (maximum deviation = 0.0878Å for C2) form a dihedral angle of 87.85 (7)° with the benzene ring and is almost coplanar with the mean plane of the cyclohexene ring [dihedral angle = 7.23 (7)º]. In the crystal, molecules are connected into inversion dimers via pairs of N-H…N hydrogen bonds and these dimers are further linked by N-H…O hydrogen bonds into a two-dimensional network.
European Chemical Bulletin, Vol 3, No 3 (2014): European Chemical Bulletin