(2E,2′E)-1,1′-Bis(6-chloro-2-methyl-4-phenylquinolin-3-yl)-3,3′-(1,4-phenylene)diprop-2-en-1-one ethyl acetate disolvate

In the title solvate, C44H30Cl2N2O2·2C4H8O2, the complete polycyclic molecule is generated by inversion symmetry. The dihedral angle between the quinolyl ring system (Q; r.m.s. deviation = 0.020 Å) and the pendant phenyl ring is 78.80 (6)°; the dihedral angle between Q and the central benzene ring is 85.92 (7)°. In the crystal, the components are linked by C—H⋯O and C—H⋯π interactions, generating (110) layers. Weak aromatic π–π stacking [centroid–centroid distances = 3.7025 (11) and 3.8124 (10) Å] is also observed.


Related literature
Cg1 is the centroid of the C12-C17 ring.  The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of (I)consists of one-half of the molecule, with the other half generated by a crystallographic inversion centre. In the title molecule the centrosymmetric phenyl ring is attached to two prop-2-en-1-one linked to two 6-chloro-2-methyl-4-phenylquinolin-3-yl and two molecules of ethyl acetate are co-crystalized with it. The two rings of quinolyl group are fused in axial fashion and form adihedral angle of 1.72 (5)° and this quasi plane system forms a dihedral angle of 78.80 (6)° with the phenyl ring (C12-C17) attached to quinolyl moiety. The crystal packing can be described as layers in zigzag parallel to the (110) plane. (Fig. 2). It features C-H···O and C-H···π interactions (Table. 1) and strong π-π stacking interactions between quinolyl rings with a centroid-centroid distance of 3.7025 (11) and 3.8124 (10)å. These interactions link the molecules within the layers and also link the layers together, reinforcing the cohesion of the structure.

Experimental
A mixture of 2-aminobenzophénone (1.0 mmol), acetylacetone (1.2 mmol), water (1 ml) and 1.0 eq. of 1 N HCl, gave the corresponding 1-(2-methyl-4-phenylquinolin-3-yl) ethanone as a white solid in 86% yield, according to the procedure reported by Wang et al. (2006). Next, the title compound was prepared in 75% of yield, by an aldol condensation reaction of the Friedländer product with 0.5 eq. of terephthalaldehyde in an ethanolic solution of NaOH at room temperature.

Refinement
Approximate positions for all the H atoms were first obtained from the difference electron density map. However, the H atoms were situated into idealized positions and the H-atoms have been refined within the riding atom approximation.
The applied constraints were as follow: C aryl -H aryl = 0.95 Å; C methylene -H methylene = 0.99 Å and C methyl -H methyl = 0.98 Å and; The idealized methyl group was allowed to rotate about the C-C bond during the refinement by application of the command AFIX 137 in SHELXL97 (Sheldrick, 2008). U iso (H methyl ) = 1.5U eq (C methyl ) or U iso (H aryl or H methylene ) = 1.2 U eq (C aryl or C methylene ).

Figure 1
The molecular geometry of (I) with displacement ellipsoids drawn at the 50% probability level. Only the contents of the asymmetric unit are numbered. The two ethyl acetate co-crystalized molecules were omitted for clarity.

Figure 2
A diagram of the layered crystal packing of (I) viewed down the c axis.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) 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.