2-Amino-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile propan-2-one monosolvate

In the crystal structure of the title compound, C19H20N2O3·C3H6O, molecules are linked into inversion dimers with an R 2 2(12) motif by pairs of N—H⋯N hydrogen bonds. These dimers are further connected into chains running along the a axis by N—H⋯O hydrogen bonds. C—H⋯N and C—H⋯π interactions also feature in the packing. The cyclohexene ring adopts nearly an envelope conformation [puckering parameters are Q T = 0.456 (2) Å, θ = 54.6 (3)° and ϕ = 225.2 (3)°].

In the crystal structure of the title compound, C 19 H 20 N 2 O 3 Á-C 3 H 6 O, molecules are linked into inversion dimers with an R 2 2 (12) motif by pairs of N-HÁ Á ÁN hydrogen bonds. These dimers are further connected into chains running along the a axis by N-HÁ Á ÁO hydrogen bonds. C-HÁ Á ÁN and C-HÁ Á Á interactions also feature in the packing. The cyclohexene ring adopts nearly an envelope conformation [puckering parameters are Q T = 0.456 (2) Å , = 54.6 (3) and ' = 225.2 (3) ].

Allahverdiyev Comment
Compounds such as 4H-chromenes and fused 4H-chromenes are a great class of organic drugs due to their wide applications in chemo therapy. They exhibited anticancer activities (Kemnitzer et al., 2007(Kemnitzer et al., , 2008Abd-El-Aziz et al., 2004, 2007Gourdeau et al., 2004;Sabry et al., 2011;Mahdavi et al., 2011) and have used in treatment of Alzheimer's disease and Schizophrenia disorder (Brühlmann et al., 2001). In this context and further to our on-going study in synthesis and biological investigation of 4H-chromene compounds (Mohamed et al. 2012), we report in this study the structure and synthesis of the title compound (I).
In the crystal structure, adjacent molecules are connected by the pairs of N-H···N hydrogen bonds, forming dimers, with an R 2 2 (12) motif (Bernstein et al., 1995; Table 1, Fig. 2). These dimers are further connected to chains running along the a axis by N-H···O hydrogen bonds. Furthermore, C-H···π interactions contribute to the stabilization of the crystal packing (Table 1, Fig. 2).

Experimental
To a solution of 184 mg (1 mmol) (4-methoxybenzylidene)propanedinitrile in 50 ml ethanol, 140 mg (1 mmol) 5,5-dimethylcyclohexane-1,3-dione was added in presence of 123 mg (1 mmol) (4-aminophenyl)methanol as catalyst. The reaction mixture was refluxed at 350 K for 5 h, then cooled at ambient temperature. The resin product that formed was solidified by washing with acetone then filtered off under vacuum and recrystallized from ethanol. Single crystals suitable for X-ray diffraction were produced by slow evaporation of ethanol/acetone solution (1:1) of (I) over two days at room temperature. Yield is 86%, M.p. 443 K.

Figure 1
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.   where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.59 e Å −3 Δρ min = −0.50 e Å −3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.