(E)-2-(4-Chlorobenzylidene)indan-1-one

In the title compound, C16H11ClO, the dihedral angle between the almost planar dihydroindene ring system (r.m.s. deviation = 0.009 Å) and the chlorobenzene ring is 3.51 (14)°. In the crystal, molecules are connected by C—H⋯O and weak C—H⋯Cl interactions, forming infinite layers parallel to (101).

In the title compound, C 16 H 11 ClO, the dihedral angle between the almost planar dihydroindene ring system (r.m.s. deviation = 0.009 Å ) and the chlorobenzene ring is 3.51 (14) . In the crystal, molecules are connected by C-HÁ Á ÁO and weak C-HÁ Á ÁCl interactions, forming infinite layers parallel to (101).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009  and c-Kit inhibitors. Initial strategies involved single target therapies and resulted in the FDA approval of Avastin (a humanized monoclonal antibody targeting VEGF, the growth factor that stimulates VEGFRs) for the treatment of metastatic colorectal cancer (Muhsin et al. 2006). As part of our studies in this area, we now report the synthesis and structure of the title compound, (I).
All parameters in (I) within normal ranges. The dihydroindene ring is almost planar with the maximum deviation of -0.015 (4)Å for atom C7. It make a dihedral angle of 3.51 (14)° with the adjacent benzene ring (Fig. 1). In the crystal, the molecules are interconnected by C-H···O and C-H···Cl interactions (Table 1)

Experimental
A mixture of 2,3-dihydro-IH-indene-1-one (0.001 mmol) and 4-chlorbenzaldehyde (0.001 mmol) were dissolved in methanol (10 mL) and 30% sodium hydroxide solution (5ml) was added. The solution was stirred for 5 hour. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice then neutralized with Con HCl. The precipitated solid was filtered, washed with water and recrystallised from ethanol to reveal the title compound as light yellow plates of (I).

Refinement
All H-atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 and 0.99Å, and with U iso = 1.2U eq (C). Fig. 1

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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 > 2sigma(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.