The first fully automated small-molecule robotic X-ray diffractometer is described. After demonstrating the utility of the instrument using multiple samples of ammonium bitartrate, we investigated the conformational chirality of diphenyl dichalcogenide (E(2)Ph(2), where E = S, Se, or Te). Structural and computational studies suggest that the two enantiomers are energetically indistinguishable. Therefore, it was unsurprising that we found (in 35 suitable data collections) the proportion 0.51:0.49 of M-S(2)Ph(2) to P-S(2)Ph(2) in the bulk sample. Interestingly, after 65 data collections of Te(2)Ph(2), (46 provided suitable data sets), we found the proportion 0.72 +/- 0.13 of M-Te(2)Ph(2), suggesting there could be a statistically significant preference for the M-enantiomer in the sample examined here. We found that Se(2)Ph(2) underwent homochiral crystallization, with all 24 crystals being M. Our experiments may represent a salutary lesson in statistical analysis.