# Diverse molecule benchmark set for sci-form
# Covers: simple organics, all functional groups, halogens, heteroatoms,
# aromatic systems, rings, stereo, metals, and complex drug-like molecules
#
# Format: SMILES\tName\tCategory
#
# === SIMPLE MOLECULES ===
C	methane	simple
CC	ethane	simple
C=C	ethylene	simple
C#C	acetylene	simple
CCC	propane	simple
CCCC	butane	simple
CCCCC	pentane	simple
CCCCCC	hexane	simple
CC(C)C	isobutane	simple
CC(C)(C)C	neopentane	simple
C1CCCCC1	cyclohexane	simple
C1CCC1	cyclobutane	simple
C1CC1	cyclopropane	simple
C1CCCCCCC1	cyclooctane	simple
#
# === ALCOHOLS & ETHERS ===
CO	methanol	alcohol
CCO	ethanol	alcohol
CC(C)O	isopropanol	alcohol
OCC(O)CO	glycerol	alcohol
COC	dimethylether	ether
CCOCC	diethylether	ether
C1CCOC1	tetrahydrofuran	ether
C1CCOCC1	tetrahydropyran	ether
#
# === AMINES ===
CN	methylamine	amine
CCN	ethylamine	amine
CN(C)C	trimethylamine	amine
C1CCNCC1	piperidine	amine
C1CNCCN1	piperazine	amine
C1CCNC1	pyrrolidine	amine
NCC(N)C(=O)O	alanine	aminoacid
#
# === CARBONYLS ===
CC=O	acetaldehyde	carbonyl
CCC=O	propanal	carbonyl
CC(C)=O	acetone	carbonyl
CCCC(=O)CC	3-hexanone	carbonyl
O=CC=O	glyoxal	carbonyl
#
# === CARBOXYLIC ACIDS & ESTERS ===
CC(=O)O	acetic_acid	acid
CCC(=O)O	propionic_acid	acid
OC(=O)CC(=O)O	malonic_acid	acid
CC(=O)OC	methyl_acetate	ester
CC(=O)OCC	ethyl_acetate	ester
CCOC(=O)C(CC)CC	ethyl_2ethylbutyrate	ester
#
# === AMIDES & UREAS ===
CC(=O)N	acetamide	amide
CC(=O)NC	n-methylacetamide	amide
NC(=O)NC	urea_dimethyl	urea
O=C1CCCN1	2-pyrrolidinone	amide
#
# === AROMATICS ===
c1ccccc1	benzene	aromatic
Cc1ccccc1	toluene	aromatic
c1ccc(O)cc1	phenol	aromatic
c1ccc(N)cc1	aniline	aromatic
c1ccncc1	pyridine	aromatic
c1ccoc1	furan	aromatic
c1cc[nH]c1	pyrrole	aromatic
c1ccsc1	thiophene	aromatic
c1cnc2ccccc2n1	quinazoline	aromatic
c1ccc2[nH]ccc2c1	indole	aromatic
c1ccc2ccccc2c1	naphthalene	aromatic
c1cccc2ccccc12	azulene_like	aromatic
c1ccc2c(c1)ccc1ccccc12	phenanthrene	aromatic
c1ccc(-c2ccccc2)cc1	biphenyl	aromatic
c1ccc2c(c1)c1ccccc1c1ccccc21	triphenylene	aromatic
#
# === HALOGENS ===
CCl	chloromethane	halogen
CBr	bromomethane	halogen
CI	iodomethane	halogen
CF	fluoromethane	halogen
FC(F)(F)C	1_1_1-trifluoroethane	halogen
ClC(Cl)Cl	chloroform	halogen
FC(F)(F)c1ccccc1	trifluoromethylbenzene	halogen
Clc1ccc(Cl)cc1	1_4-dichlorobenzene	halogen
Brc1ccccc1	bromobenzene	halogen
Ic1ccccc1	iodobenzene	halogen
FC(F)(F)C(F)(F)F	hexafluoroethane	halogen
#
# === SULFUR COMPOUNDS ===
CS	methanethiol	sulfur
CSSC	dimethyldisulfide	sulfur
CS(=O)C	dimethylsulfoxide	sulfur
CS(=O)(=O)C	dimethylsulfone	sulfur
c1ccsc1	thiophene	sulfur
CC(=O)SCC	s-ethyl_thioacetate	sulfur
OS(=O)(=O)O	sulfuric_acid	sulfur
#
# === PHOSPHORUS COMPOUNDS ===
CP(C)C	trimethylphosphine	phosphorus
COP(=O)(OC)OC	trimethylphosphate	phosphorus
NP(=O)(N)N	phosphoramide	phosphorus
#
# === NITROGEN HETEROCYCLES ===
c1cnc[nH]1	imidazole	n-heterocycle
c1ccn[nH]1	pyrazole	n-heterocycle
c1nn[nH]n1	tetrazole	n-heterocycle
c1ncc2nc[nH]c2n1	purine	n-heterocycle
C1=CC=CN1	1H-pyrroline	n-heterocycle
c1cnc2[nH]ccc2c1	7-azaindole	n-heterocycle
c1ncc(-c2ccncc2)o1	4-(furan-2-yl)pyridine	n-heterocycle
#
# === OXYGEN HETEROCYCLES ===
C1=COC=C1	furan_2h	o-heterocycle
C1CCOC(=O)C1	delta-valerolactone	o-heterocycle
O=c1[nH]c(=O)c(=O)[nH]c1=O	barbituric_acid	o-heterocycle
C1OC1	oxirane	o-heterocycle
c1cc2ccoc2cc1	benzofuran	o-heterocycle
#
# === STEREO / CHIRALITY ===
C[C@@H](O)CC	r-2-butanol	stereo
C/C=C/C	trans-2-butene	stereo
C/C=C\C	cis-2-butene	stereo
O[C@@H]1CCCC[C@H]1O	trans-1_2-cyclohexanediol	stereo
#
# === BRIDGED & FUSED RINGS ===
C1CC2CCC1CC2	norbornane	bridged
C12CC3CC(CC(C3)C1)C2	adamantane	bridged
C1CCC2(CC1)CCCCC2	spiro[4.5]decane	bridged
C1CCC2CCCCC2C1	decalin	fused
C1CC2CCCC(C1)C2	bicyclo[3.3.0]octane	fused
#
# === COMPLEX DRUG-LIKE ===
CC(=O)Oc1ccccc1C(=O)O	aspirin	drug
CC12CCC3c4ccc(O)cc4CCC3C1CCC2O	estradiol	drug
CC(C)Cc1ccc(CC(C)C(=O)O)cc1	ibuprofen	drug
Cn1c(=O)c2c(ncn2C)n(C)c1=O	caffeine	drug
CC(=O)Nc1ccc(O)cc1	acetaminophen	drug
c1ccc2c(c1)cc1ccc3cccc4ccc2c1c34	pyrene	drug
OC(=O)c1ccccc1O	salicylic_acid	drug
OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O	glucose	drug
CC(C)NCC(O)c1ccc(O)c(O)c1	isoproterenol	drug
c1ccc(-c2cc(-c3ccccc3)cc(-c3ccccc3)c2)cc1	1_3_5-triphenylbenzene	drug
#
# === MACROCYCLES ===
C1CCCCCCCCCCCC1	cyclotridecane	macrocycle
C1CCCCCCCCCC1	cycloundecane	macrocycle
#
# === STRAINED SYSTEMS ===
C12C3C4C1C5C3C2C45	cubane	strained
C1=CC=CC1	cyclopentadiene	strained
#
# === SILICON ===
[Si](C)(C)C	trimethylsilane	silicon
C[Si](C)(C)O[Si](C)(C)C	hexamethyldisiloxane	silicon
#
# === BORON ===
OB(O)c1ccccc1	phenylboronic_acid	boron
B1OC(C)(C)C(C)(C)O1	pinacolborane_scaffold	boron
#
# === SELENIUM ===
C[Se]C	dimethylselenide	selenium
#
# === COMPLEX POLYCYCLICS ===
C1CCC2C(C1)CCC1CCCCC12	trans-decalin_sub	polycyclic
c1cc2ccc3cccc4ccc(c1)c2c34	fluoranthene	polycyclic
C1CC2(CCCC3(CCCCC3)C2)CC1	spiro_bicyclic	polycyclic
#
# === MULTI-FUNCTIONAL ===
OC(=O)c1cc(O)c(O)c(O)c1	gallic_acid	multifunc
Nc1ccc(S(=O)(=O)Nc2ccccn2)cc1	sulfapyridine	multifunc
OC(=O)CCC(=O)C(=O)O	alpha-ketoglutaric_acid	multifunc
NC(=O)c1cnccn1	pyrazinecarboxamide	multifunc
CC(=O)N(c1ccccc1)c1ccc(O)cc1	4-acetamidophenol_N-phenyl	multifunc
O=C1C=CC(=O)C=C1	benzoquinone	multifunc
NC(CS)C(=O)O	cysteine	multifunc
CC(N)Cc1ccc(O)c(O)c1	norepinephrine_analog	multifunc
