(E)-1-(4-Chlorophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

The title compound, C17H16ClNO, was synthesized using a solvent-free method by reaction of 4-(dimethylamino)benzaldehyde with 4-chloroacetophenone and NaOH. The chlorophenyl ring makes a dihedral angle of 18.1 (3)° with the central propenone unit, while the (dimethylamino)phenyl group is disordered over two orientations of equal occupancies, which make dihedral angles with the central propenone unit of 32.9 (3) and 57.4 (3)°, respectively.

The title compound, C 17 H 16 ClNO, was synthesized using a solvent-free method by reaction of 4-(dimethylamino)benzaldehyde with 4-chloroacetophenone and NaOH. The chlorophenyl ring makes a dihedral angle of 18.1 (3) with the central propenone unit, while the (dimethylamino)phenyl group is disordered over two orientations of equal occupancies, which make dihedral angles with the central propenone unit of 32.9 (3) and 57.4 (3) , respectively.

Related literature
For a related structure, see: Li et al. (1992). Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. This paper discloses a user-friendly, solvent-free protocol for the synthesis of chalcones, starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH. The method can be considered to be a general route for chalcone synthesis, and the title compound was prepared in this way.

Experimental
The bond lengths and angles of the molecule ( Fig. 1) are normal and comparable to those observed in the related compound (Li et al., 1992). The (dimethylamino)phenyl group exhibits rotational disorder, with one orientation including atoms C10, C11, C12, C13, C14 and C15, and another orientation including C10, C11′, C12′, C13, C14′ and C15′. The refined site occupancy factors for the two orientations is 0.500 (5).

Figure 1
The molecular structure showing 30% probability displacement ellipsoids for non-H atoms.   where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.16 e Å −3 Δρ min = −0.12 e Å −3 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.

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