@johnmay, is there anything that you think that can be done on the choice of bonds to use the wedge for on the bridgehead carbons for these two SMILES:

Cl[C@@]12C(=C([C@@]([C@@H]3COS(OC[C@@H]31)=O)(C2(Cl)Cl)Cl)Cl)Cl
Cl[C@]12C(=C([C@]([C@@H]3COS(OC[C@@H]31)=O)(C2(Cl)Cl)Cl)Cl)Cl

According to Brecher (below, right), this wedges on the two bonds to the two chlorines should be on the bonds towards the middle bridging CCl2 group, I think (whereas those on the bonds to the hydrogens in the above seem fine, per below left):