(2E)-3-(2-Chlorobenzo[h]quinolin-3-yl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one

In the title compound, C32H21ClN2O, an almost planar (r.m.s. deviation = 0.033 Å) prop-2-en-1-one bridge links quinolinyl and benzoquinolinyl residues; the latter are twisted out of the plane of the bridge [dihedral angles = 75.94 (5) and 20.20 (5)°, respectively]. In the crystal, a three-dimensional architecture arises as a result of C—H⋯O, C—H⋯π and π–π [centroid–centroid distances involving pyridine rings = 3.5806 (7)–3.7537 (7) Å] interactions.


Related literature
Cg1 is the centroid of the N1-pyridyl ring.

Comment
In connection with the biological potential of quinolinyl derivatives (Jörg et al. 2007;Prasath et al. 2013a), the title compound (I) was prepared and subjected to a crystallographic study.

Experimental
A mixture of 3-acetyl-2-methyl-4-phenylquinoline (260 mg, 0.001 M) and 2-chlorobenzoquinoline-3-carbaldehyde (240 mg, 0.001 M) in methanol (20 ml) containing potassium hydroxide (0.2 g) was stirred at room temperature for 12 h. After this, the reaction mixture was neutralized with dilute acetic acid and the resultant solid was filtered, dried and purified by column chromatography using an ethyl acetate -hexane (4:1) mixture to afford the title compound, (I). Re-crystallization was by slow evaporation of an acetone solution of (I), which yielded colourless blocks in 80% yield; M.pt: 460-462 K.

Figure 1
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.  View in projection down the a axis of the unit-cell contents of (I). The C-H···O, C-H···π and π-π interactions are shown as orange, purple and blue dashed lines, respectively.

(2E)-3-(2-Chlorobenzo[h]quinolin-3-yl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one
Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq