(2E)-3-(2-Chloro-6-methyl-3-quinolyl)-1-(1-naphthyl)prop-2-en-1-one

In the title molecule, C23H16ClNO, the quinoline and naphthalene ring systems are individually planar, with maximum deviations of 0.020 (2) and 0.033 (2) Å, respectively, and are inclined at a dihedral angle of 30.01 (4)°. Intramolecular C—H⋯O and C—H⋯Cl interactions occur. The crystal structure is devoid of any classical hydrogen bonds, but symmetry-related molecules are linked via weak C—H⋯Cl interactions, forming chains propagating in [001].


Related literature
The title molecule is presented in Fig. 1. The bond distances are as expected (Allen, 2002). The mean planes of the quinoline and naphthalene rings, defined by atoms N1/C1-C9 and C14-C23, respectively, are individually planar with maximum deviations of 0.020 (2) and 0.033 (2) Å, respectively. These planes are inclined at 30.01 (4)° with respect to each other.
The crystal structure is devoid of any classical hydrogen bonds, however in the molecule itself short intramolecular interactions involving atoms Cl1 and O1 are present (Table 1). In the crystal structure a weak C-H···Cl interaction links the molecules to form chains propagating in [001]; see Table 1 and Fig. 2 for details.

Refinement
Although all of the H atoms could be located in the difference Fourier maps they were included at geometrically idealized positions and refined in the riding-model approximation: C-H = 0.95 and 0.98 Å for aromatic and methyl H-atoms, respectively, with U iso (H) = 1.2U eq (C). Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title molecule, with displacement ellipsoids drawn at the 50% probability level.  Table 1 for details; H-atoms not involved in hydrogen bonds have been omitted for clarity].

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Rfactors(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.