SMILES: caffeine with three CF3 groups, by claude-sonnet-5.5
claude-sonnet-5.5 · round 1 · seed 2$0.01SVGmolecule.smi
molecule.smi · 2 lines
FC(F)(F)n1cnc2c1c(=O)n(C(F)(F)F)c(=O)n2C(F)(F)F
gallery/Caffeine with three CF3 groups/Claude Sonnet 5.5, run 2

Caffeine with three CF3 groups: Claude Sonnet 5.5

modelanthropic/claude-sonnet-5.5tasksmiles-fluorocaffeine@v1, checks c1, harness h1date2026-10-02rounds1 of 8 allowed, 12 minutes on the clockcost$0.0130thinkingmediumtokens8,508 in, 382 out, of which 0 reasoningtime9 s
Parsesdecided by a number, from the filepass
C8HF9N4O2decided by a number, from the filepass
Three N-CF3, no N-methyldecided by a number, from the filepass
The right moleculedecided by a number, from the filepass

There is no post about this one, since only some results need one, so the picture, the source and the scoring are here instead.

its other runs
Caffeine with three CF3 groups, by Claude Sonnet 5.5, run 1run 1 · 1r · $0.0132Caffeine with three CF3 groups, by Claude Sonnet 5.5, run 3run 3 · 1r · $0.0132
same prompt, other modelsall 6 runs on Caffeine with three CF3 groups →
the prompt it was given
Give the SMILES for caffeine with all three N-methyl groups replaced by trifluoromethyl groups.
Frozen at v1. This model got this and nothing else.
ground truth

Caffeine's skeleton with a CF3 on N1, N3 and N7, which is C8HF9N4O2. The prompt pack this came from gives C8H3F9N4O2, which is wrong: swapping the methyls takes all nine hydrogens with them, and only the C8 hydrogen stays. Decided with RDKit by an exact canonical match, because fluorinated isocaffeine has the same formula with a CF3 on the wrong nitrogen. How it is scored, and this run's files on GitHub.