Benzene-1,3,5-tricarbonyl trichloride

In the title molecule, C9H3Cl3O3, there are three short interactions involving the benzene H atoms and the chloroformyl Cl atoms. In the crystal, molecules stack along the a axis with no significant non-bonded interactions.

In the title molecule, C 9 H 3 Cl 3 O 3 , there are three short interactions involving the benzene H atoms and the chloroformyl Cl atoms. In the crystal, molecules stack along the a axis with no significant non-bonded interactions.
The molecular structure of the title compound is shown in Figure 1. Bond lengths and angles in (I) show normal values.
The geometric parameters of the title molecule agree well with those reported for similar structures (Leser & Rabinovich, 1978a,b). The non-hydrogen atoms of the molecule lie in a nearly plane with an r.m.s deviation of 0.1118 Å. Three intramolecular hydrogen bonds are observed between the C-H of phenyl group and the Cl atom of the chloroformyl group (Jeffrey et al., 1985) (Figure 1 and Table 1). The shortest contacts in the crystal packing are O1···C2 i [3.094 (6) Å],

Experimental
Compound (I) was synthesized according to the literature procedure of Hamel et al. (1968). Single crystals suitable for Xray diffraction were grown by slow evaporation from 4:1 (V/V) mixed solution of petroleum ether and chloroform at room temperature.

Refinement
All H atoms were included in the riding-model approximation, with C-H distances of 0.93 Å, and the isotropic displacement parameters were set equal to 1.2U eq of the carrier atom.

Computing details
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).  The molecular structure of (I), showing 30% probability displacement ellipsoids. Dashed lines indicate hydrogen bonds. 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.