def test_1_3_aromatic_heteroatom_canonicalization3():
    """1,3 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('Oc1ncc[nH]1'), 'O=c1[nH]cc[nH]1')

def test_cyano_iso_cyanic_acid_canonicalization2():
    """cyano/iso-cyanic acid tautomer"""
    eq_(canonicalize_tautomer_smiles('C(=N)=O'), 'N=C=O')

def test_isocyanide_canonicalization2():
    """isocyanide tautomer"""
    eq_(canonicalize_tautomer_smiles('[C-]#[NH+]'), 'C#N')

def test_keten_ynol_canonicalization2():
    """keten/ynol tautomer"""
    eq_(canonicalize_tautomer_smiles('CC#CO'), 'CC=C=O')

def test_oxim_nitroso_canonicalization2():
    """oxim nitroso tautomer"""
    eq_(canonicalize_tautomer_smiles('CC(C)N=O'), 'CC(C)=NO')

def test_heterocyclic_canonicalization4():
    """heterocyclic tautomer"""
    eq_(canonicalize_tautomer_smiles('n1ccc2c[nH]ccc12'), 'c1cc2[nH]ccc2cn1')

def test_furanone_canonicalization():
    """furanone tautomer"""
    eq_(canonicalize_tautomer_smiles('C1=CC=C(O1)O'), 'Oc1ccco1')

def test_1_5_aromatic_heteroatom_canonicalization6():
    """1,5 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('Oc1c(cccc3)c3nc2ccncc12'), 'O=c1c2ccccc2[nH]c2ccncc12')

def test_1_3_1_5_aromatic_heteroatom_canonicalization():
    """1,3 and 1,5 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('Oc1ncncc1'), 'O=c1cc[nH]cn1')

def test_1_3_heteroatom_canonicalization6():
    """1,3 heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('CN=c1[nH]cncc1'), 'CN=c1cc[nH]cn1')

def test_1_5_aromatic_heteroatom_canonicalization4():
    """1,5 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('Cc1nnc2nc[nH]n12'), 'Cc1n[nH]c2ncnn12')

def test_1_3_heteroatom_canonicalization5():
    """1,3 heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('N=c1[nH]ccn(C)1'), 'Cn1cc[nH]c1=N')

def test_1_3_heteroatom_canonicalization4():
    """1,3 heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('SC(N)=N'), 'NC(N)=S')

def test_1_3_heteroatom_canonicalization2():
    """1,3 heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('CNC(C)=O'), 'CNC(C)=O')

def test_1_11_aromatic_heteroatom_canonicalization2():
    """1,11 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('N=C1C=CC(=Cc2ccc(O)cc2)C=C1'), 'Nc1ccc(C=C2C=CC(=O)C=C2)cc1')

def test_1_5_aromatic_heteroatom_canonicalization8():
    """1,5 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('C2(C1=C([NH]C=N1)[NH]C(=N2)N)=O'), 'N=c1[nH]c(=O)c2[nH]cnc2[nH]1')

def test_heterocyclic_canonicalization2():
    """heterocyclic tautomer"""
    eq_(canonicalize_tautomer_smiles('c1cc(=O)[nH]c2nccn12'), 'O=c1ccn2cc[nH]c2n1')

def test_1_5_aromatic_heteroatom_canonicalization9():
    """1,5 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('Oc1n(C)ncc1'), 'Cn1[nH]ccc1=O')

def test_heterocyclic_canonicalization5():
    """heterocyclic tautomer"""
    eq_(canonicalize_tautomer_smiles('c1cnc2ccc[nH]c12'), 'c1cnc2cc[nH]c2c1')

def test_1_5_aromatic_heteroatom_canonicalization10():
    """1,5 aromatic heteroatom H shift"""
    eq_(canonicalize_tautomer_smiles('O=c1nc2[nH]ccn2cc1'), 'O=c1ccn2cc[nH]c2n1')