Crystal structure of haloxon, C14H14Cl3O6P

The crystal structure of haloxon has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional theory techniques. Haloxon crystallizes in space group P2(1)/n (#14) with a = 19.60382(6), b = 10.05473(3), c = 8.73591(2) angstrom, beta = 92.6617(2)degrees, V = 1720.088(11) angstrom(3), and Z = 4. The structure consists of discrete molecules. The mean planes of the fused ring systems are approximately 0-11 and 011. The rings form staggered stacks perpendicular to these planes. There are no traditional hydrogen bonds in the structure, but several C-HMIDLINE HORIZONTAL ELLIPSISO and C-HMIDLINE HORIZONTAL ELLIPSISCl hydrogen bonds contribute to the crystal energy. The powder pattern has been submitted to ICDD for inclusion in the Powder Diffraction File (TM) (PDF (R)).