# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr 28 01:33:55 2020
#   Inital geometry file: a 196 line input string
#   Ligand name: 2,2',2'',2'''-{(2S)-2-[4-({[(2-hydroxyethyl)sulfanyl]acetyl}amino)benzyl]-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl}tetraacetic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OCCSCC(=O)Nc1ccc(C[C@H]2CN(CCN(CCN(CCN2CC(O)=O)CC(O)=O)CC(O)=O)CC(O)=O)cc1
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 DOE  DOE  '2,2',2'',2'''-{(2S)-2-[4-({[(2-hydroxyethyl)sulfanyl]acetyl}amino)benzyl]-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl}tetraacetic acid'  ligand  80  43  .  2021-08-08  2021-08-08  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_DOE
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 DOE  C1    C  CH1    0   0.023   -1.3753   2.3183   5.1029
 DOE  C2    C  CH2    0  -0.361   -0.2354   2.9764   4.3050
 DOE  C3    C  CH2    0  -0.260   -0.3900   3.3959   1.9429
 DOE  C4    C  CH2    0  -0.361   -1.3077   2.2359   1.5217
 DOE  C5    C  CH2    0  -0.295    0.1945   0.3935   1.0585
 DOE  C6    C  CH2    0  -0.225   -0.4193  -0.9034   1.5701
 DOE  C7    C  CH2    0  -0.271   -0.4467  -0.5670   3.9657
 DOE  C8    C  CH2    0  -0.340   -1.3234  -0.1402   5.1721
 DOE  C10   C  C      0   0.380    0.3597   0.2155   7.7502
 DOE  C12   C  C      0   0.374   -1.0340   6.3394   2.6917
 DOE  C14   C  C      0   0.385   -0.2639   1.0890  -1.9397
 DOE  C16   C  C      0   0.387   -3.1448  -2.2902   1.9421
 DOE  C17   C  CH2    0  -0.521   -2.0088   3.3474   6.0541
 DOE  C18   C  CR6    0   0.041   -3.3372   2.9109   6.5973
 DOE  C19   C  CR16   0  -0.264   -4.5182   3.4782   6.1253
 DOE  C20   C  CR16   0  -0.330   -5.7549   3.0736   6.6011
 DOE  C21   C  CR6    0   0.325   -5.8435   2.0755   7.5681
 DOE  C22   C  CR16   0  -0.359   -4.6727   1.4861   8.0412
 DOE  C23   C  CR16   0  -0.203   -3.4408   1.9047   7.5572
 DOE  C24   C  C      0   0.557   -7.5149   1.1509   9.1479
 DOE  C25   C  CH2    0  -0.690   -9.0077   0.9317   9.2790
 DOE  C26   C  CH2    0  -0.572   -9.8594  -0.8933  11.3116
 DOE  C27   C  CH2    0  -0.211   -8.7048  -0.9049  12.2993
 DOE  N1    N  NT     0  -0.408   -1.0097   1.1107   5.8214
 DOE  N2    N  NT     0  -0.449   -0.7058   3.8921   3.2714
 DOE  N3    N  NT     0  -0.364   -0.7728   1.3325   0.5252
 DOE  N4    N  NT     0  -0.409   -1.2364  -0.8174   2.7693
 DOE  N5    N  NH1    0  -0.663   -7.1343   1.6948   7.9801
 DOE  O1    O  O      0  -0.450   -0.6798  -0.0611   8.3774
 DOE  O2    O  OC    -1  -0.673    1.5211  -0.1283   8.0549
 DOE  O3    O  O      0  -0.625   -2.0791   6.0305   2.0951
 DOE  O4    O  OC    -1  -0.710   -0.5231   7.4790   2.7590
 DOE  O5    O  O      0  -0.532   -0.6838  -0.0800  -1.8736
 DOE  O6    O  OC    -1  -0.717    0.2282   1.6475  -2.9449
 DOE  O7    O  O      0  -0.529   -3.6169  -1.3249   1.3213
 DOE  O8    O  OC    -1  -0.681   -3.5420  -3.4765   1.8951
 DOE  O9    O  O      0  -0.444   -6.7365   0.8452  10.0440
 DOE  O10   O  OH1    0  -0.680   -8.0319   0.3182  12.4122
 DOE  S1    S  S2     0  -0.034   -9.4036  -0.8196   9.5550
 DOE  HC1   H  HCH1   0   0.233   -2.1477   2.0422   4.3807
 DOE  HC21  H  HCH2   0   0.227    0.4362   3.4971   4.9978
 DOE  HC22  H  HCH2   0   0.196    0.3813   2.1943   3.8520
 DOE  HC31  H  HCH2   0   0.190    0.6669   3.0787   1.8833
 DOE  HC32  H  HCH2   0   0.240   -0.5008   4.2088   1.2254
 DOE  HC41  H  HCH2   0   0.236   -1.5817   1.6287   2.3842
 DOE  HC42  H  HCH2   0   0.200   -2.2461   2.6659   1.1512
 DOE  HC51  H  HCH2   0   0.153    0.8407   0.8581   1.8199
 DOE  HC52  H  HCH2   0   0.225    0.8729   0.0989   0.2572
 DOE  HC61  H  HCH2   0   0.256   -1.0419  -1.2747   0.7573
 DOE  HC62  H  HCH2   0   0.099    0.3985  -1.6372   1.7120
 DOE  HC71  H  HCH2   0   0.204    0.2796   0.2204   3.7602
 DOE  HC72  H  HCH2   0   0.223    0.1573  -1.4544   4.2307
 DOE  HC81  H  HCH2   0   0.214   -2.3593  -0.0726   4.8303
 DOE  HC82  H  HCH2   0   0.215   -1.3071  -0.9189   5.9379
 DOE  HC91  H  HCH2   0   0.238    0.4296   2.1490   6.8878
 DOE  HC92  H  HCH2   0   0.171    1.1125   0.9216   5.8560
 DOE  H111  H  HCH2   0   0.235    0.8093   5.3867   3.2823
 DOE  H112  H  HCH2   0   0.279   -0.4038   5.5014   4.5358
 DOE  H131  H  HCH2   0   0.197    0.6025   2.5267  -0.5969
 DOE  H132  H  HCH2   0   0.211   -1.0954   2.7698  -0.9157
 DOE  H151  H  HCH2   0   0.202   -2.4513  -2.0437   3.9287
 DOE  H152  H  HCH2   0   0.198   -1.3260  -2.9262   2.9283
 DOE  H171  H  HCH2   0   0.233   -2.1330   4.2868   5.5103
 DOE  H172  H  HCH2   0   0.203   -1.3100   3.5512   6.8718
 DOE  H19   H  HCR6   0   0.229   -4.4772   4.2550   5.3707
 DOE  H20   H  HCR6   0   0.241   -6.6562   3.5401   6.2205
 DOE  H22   H  HCR6   0   0.266   -4.7065   0.6950   8.7734
 DOE  H23   H  HCR6   0   0.246   -2.5426   1.4117   7.9093
 DOE  H251  H  HCH2   0   0.271   -9.3827   1.5190  10.1191
 DOE  H252  H  HCH2   0   0.342   -9.5482   1.2607   8.3918
 DOE  H261  H  HCH2   0   0.307  -10.5597  -0.0843  11.5289
 DOE  H262  H  HCH2   0   0.287  -10.4139  -1.8302  11.4013
 DOE  H271  H  HCH2   0   0.207   -8.0270  -1.7300  12.0446
 DOE  H272  H  HCH2   0   0.263   -9.1225  -1.1352  13.2838
 DOE  HN5   H  HNH1   0   0.416   -7.8743   1.9486   7.3433
 DOE  H10   H  HOH1   0   0.445   -7.5204   0.4687  11.5962
 DOE  C9    C  CH2    0  -0.454    0.2531   1.1334   6.5124
 DOE  C11   C  CH2    0  -0.353   -0.2699   5.2552   3.4765
 DOE  C13   C  CH2    0  -0.414   -0.3576   1.9896  -0.6894
 DOE  C15   C  CH2    0  -0.416   -1.9912  -2.0427   2.9341

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 DOE  C1   C2    single    1.539  0.020  1.539
 DOE  C1   C17   single    1.538  0.020  1.538
 DOE  C1   N1    single    1.452  0.020  1.452
 DOE  C1   HC1   single    0.970  0.020  1.090
 DOE  C2   N2    single    1.459  0.020  1.459
 DOE  C2   HC21  single    0.970  0.020  1.090
 DOE  C2   HC22  single    0.970  0.020  1.090
 DOE  C3   C4    single    1.538  0.020  1.538
 DOE  C3   N2    single    1.453  0.020  1.453
 DOE  C3   HC31  single    0.970  0.020  1.090
 DOE  C3   HC32  single    0.970  0.020  1.090
 DOE  C4   N3    single    1.448  0.020  1.448
 DOE  C4   HC41  single    0.970  0.020  1.090
 DOE  C4   HC42  single    0.970  0.020  1.090
 DOE  C5   C6    single    1.523  0.020  1.523
 DOE  C5   N3    single    1.450  0.020  1.450
 DOE  C5   HC51  single    0.970  0.020  1.090
 DOE  C5   HC52  single    0.970  0.020  1.090
 DOE  C6   N4    single    1.454  0.020  1.454
 DOE  C6   HC61  single    0.970  0.020  1.090
 DOE  C6   HC62  single    0.970  0.020  1.090
 DOE  C7   C8    single    1.551  0.020  1.551
 DOE  C7   N4    single    1.455  0.020  1.455
 DOE  C7   HC71  single    0.970  0.020  1.090
 DOE  C7   HC72  single    0.970  0.020  1.090
 DOE  C8   N1    single    1.444  0.020  1.444
 DOE  C8   HC81  single    0.970  0.020  1.090
 DOE  C8   HC82  single    0.970  0.020  1.090
 DOE  C9   C10   single    1.545  0.020  1.545
 DOE  C9   N1    single    1.440  0.020  1.440
 DOE  C9   HC91  single    0.970  0.020  1.090
 DOE  C9   HC92  single    0.970  0.020  1.090
 DOE  C10  O1    deloc     1.245  0.020  1.245
 DOE  C10  O2    deloc     1.249  0.020  1.249
 DOE  C11  C12   single    1.541  0.020  1.541
 DOE  C11  N2    single    1.446  0.020  1.446
 DOE  C11  H111  single    0.970  0.020  1.090
 DOE  C11  H112  single    0.970  0.020  1.090
 DOE  C12  O3    deloc     1.242  0.020  1.242
 DOE  C12  O4    deloc     1.251  0.020  1.251
 DOE  C13  C14   single    1.544  0.020  1.544
 DOE  C13  N3    single    1.442  0.020  1.442
 DOE  C13  H131  single    0.970  0.020  1.090
 DOE  C13  H132  single    0.970  0.020  1.090
 DOE  C14  O5    deloc     1.244  0.020  1.244
 DOE  C14  O6    deloc     1.251  0.020  1.251
 DOE  C15  C16   single    1.541  0.020  1.541
 DOE  C15  N4    single    1.449  0.020  1.449
 DOE  C15  H151  single    0.970  0.020  1.090
 DOE  C15  H152  single    0.970  0.020  1.090
 DOE  C16  O7    deloc     1.241  0.020  1.241
 DOE  C16  O8    deloc     1.252  0.020  1.252
 DOE  C17  C18   single    1.500  0.020  1.500
 DOE  C17  H171  single    0.970  0.020  1.090
 DOE  C17  H172  single    0.970  0.020  1.090
 DOE  C18  C19   aromatic  1.393  0.020  1.393
 DOE  C18  C23   aromatic  1.394  0.020  1.394
 DOE  C19  C20   aromatic  1.385  0.020  1.385
 DOE  C19  H19   single    0.930  0.020  1.080
 DOE  C20  C21   aromatic  1.393  0.020  1.393
 DOE  C20  H20   single    0.930  0.020  1.080
 DOE  C21  C22   aromatic  1.394  0.020  1.394
 DOE  C21  N5    single    1.407  0.020  1.407
 DOE  C22  C23   aromatic  1.388  0.020  1.388
 DOE  C22  H22   single    0.930  0.020  1.080
 DOE  C23  H23   single    0.930  0.020  1.080
 DOE  C24  C25   single    1.514  0.020  1.514
 DOE  C24  N5    single    1.343  0.020  1.343
 DOE  C24  O9    double    1.226  0.020  1.226
 DOE  C25  S1    single    1.817  0.020  1.817
 DOE  C25  H251  single    0.970  0.020  1.090
 DOE  C25  H252  single    0.970  0.020  1.090
 DOE  C26  C27   single    1.519  0.020  1.519
 DOE  C26  S1    single    1.816  0.020  1.816
 DOE  C26  H261  single    0.970  0.020  1.090
 DOE  C26  H262  single    0.970  0.020  1.090
 DOE  C27  O10   single    1.401  0.020  1.401
 DOE  C27  H271  single    0.970  0.020  1.090
 DOE  C27  H272  single    0.970  0.020  1.090
 DOE  N5   HN5   single    0.860  0.020  1.020
 DOE  O10  H10   single    0.850  0.020  0.980

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 DOE  HC1   C1   N1    107.14  3.000
 DOE  HC1   C1   C17   106.66  3.000
 DOE  N1    C1   C17   110.74  3.000
 DOE  HC1   C1   C2    106.79  3.000
 DOE  N1    C1   C2    115.19  3.000
 DOE  C17   C1   C2    109.86  3.000
 DOE  HC22  C2   HC21  104.82  3.000
 DOE  HC22  C2   N2    109.70  3.000
 DOE  HC21  C2   N2    110.31  3.000
 DOE  HC22  C2   C1    109.05  3.000
 DOE  HC21  C2   C1    109.21  3.000
 DOE  N2    C2   C1    113.38  3.000
 DOE  HC32  C3   HC31  106.01  3.000
 DOE  HC32  C3   N2    108.97  3.000
 DOE  HC31  C3   N2    110.81  3.000
 DOE  HC32  C3   C4    108.76  3.000
 DOE  HC31  C3   C4    109.84  3.000
 DOE  N2    C3   C4    112.23  3.000
 DOE  HC42  C4   HC41  105.71  3.000
 DOE  HC42  C4   N3    109.16  3.000
 DOE  HC41  C4   N3    106.85  3.000
 DOE  HC42  C4   C3    107.91  3.000
 DOE  HC41  C4   C3    110.70  3.000
 DOE  N3    C4   C3    116.02  3.000
 DOE  HC52  C5   HC51  104.89  3.000
 DOE  HC52  C5   N3    108.65  3.000
 DOE  HC51  C5   N3    111.87  3.000
 DOE  HC52  C5   C6    105.51  3.000
 DOE  HC51  C5   C6    111.30  3.000
 DOE  N3    C5   C6    113.96  3.000
 DOE  HC62  C6   HC61  106.96  3.000
 DOE  HC62  C6   N4    110.39  3.000
 DOE  HC61  C6   N4    108.33  3.000
 DOE  HC62  C6   C5    108.03  3.000
 DOE  HC61  C6   C5    105.66  3.000
 DOE  N4    C6   C5    116.95  3.000
 DOE  HC72  C7   HC71  105.11  3.000
 DOE  HC72  C7   N4    110.82  3.000
 DOE  HC71  C7   N4    109.31  3.000
 DOE  HC72  C7   C8    110.07  3.000
 DOE  HC71  C7   C8    108.92  3.000
 DOE  N4    C7   C8    112.34  3.000
 DOE  HC82  C8   HC81  106.11  3.000
 DOE  HC82  C8   N1    107.40  3.000
 DOE  HC81  C8   N1    107.04  3.000
 DOE  HC82  C8   C7    109.92  3.000
 DOE  HC81  C8   C7    108.03  3.000
 DOE  N1    C8   C7    117.73  3.000
 DOE  O2    C10  O1    126.32  3.000
 DOE  O2    C10  C9    115.04  3.000
 DOE  O1    C10  C9    118.56  3.000
 DOE  O4    C12  O3    126.59  3.000
 DOE  O4    C12  C11   114.27  3.000
 DOE  O3    C12  C11   119.12  3.000
 DOE  O6    C14  O5    126.52  3.000
 DOE  O6    C14  C13   114.47  3.000
 DOE  O5    C14  C13   119.00  3.000
 DOE  O8    C16  O7    126.70  3.000
 DOE  O8    C16  C15   114.44  3.000
 DOE  O7    C16  C15   118.80  3.000
 DOE  H172  C17  H171  106.51  3.000
 DOE  H172  C17  C18   110.43  3.000
 DOE  H171  C17  C18   109.25  3.000
 DOE  H172  C17  C1    108.88  3.000
 DOE  H171  C17  C1    108.32  3.000
 DOE  C18   C17  C1    113.21  3.000
 DOE  C23   C18  C19   117.66  3.000
 DOE  C23   C18  C17   121.67  3.000
 DOE  C19   C18  C17   120.65  3.000
 DOE  H19   C19  C20   118.83  3.000
 DOE  H19   C19  C18   119.72  3.000
 DOE  C20   C19  C18   121.44  3.000
 DOE  H20   C20  C21   119.96  3.000
 DOE  H20   C20  C19   119.73  3.000
 DOE  C21   C20  C19   120.31  3.000
 DOE  N5    C21  C22   123.83  3.000
 DOE  N5    C21  C20   117.10  3.000
 DOE  C22   C21  C20   119.04  3.000
 DOE  H22   C22  C23   119.06  3.000
 DOE  H22   C22  C21   120.96  3.000
 DOE  C23   C22  C21   119.98  3.000
 DOE  H23   C23  C22   119.02  3.000
 DOE  H23   C23  C18   119.37  3.000
 DOE  C22   C23  C18   121.57  3.000
 DOE  O9    C24  N5    123.83  3.000
 DOE  O9    C24  C25   121.77  3.000
 DOE  N5    C24  C25   114.40  3.000
 DOE  H252  C25  H251  107.08  3.000
 DOE  H252  C25  S1    107.86  3.000
 DOE  H251  C25  S1    109.08  3.000
 DOE  H252  C25  C24   112.00  3.000
 DOE  H251  C25  C24   109.11  3.000
 DOE  S1    C25  C24   111.57  3.000
 DOE  H262  C26  H261  107.07  3.000
 DOE  H262  C26  S1    103.98  3.000
 DOE  H261  C26  S1    108.87  3.000
 DOE  H262  C26  C27   109.01  3.000
 DOE  H261  C26  C27   111.32  3.000
 DOE  S1    C26  C27   116.00  3.000
 DOE  H272  C27  H271  106.64  3.000
 DOE  H272  C27  O10   107.14  3.000
 DOE  H271  C27  O10   112.23  3.000
 DOE  H272  C27  C26   107.25  3.000
 DOE  H271  C27  C26   108.91  3.000
 DOE  O10   C27  C26   114.26  3.000
 DOE  C9    N1   C8    114.84  3.000
 DOE  C9    N1   C1    116.44  3.000
 DOE  C8    N1   C1    116.31  3.000
 DOE  C11   N2   C3    112.71  3.000
 DOE  C11   N2   C2    113.21  3.000
 DOE  C3    N2   C2    111.31  3.000
 DOE  C13   N3   C5    114.39  3.000
 DOE  C13   N3   C4    113.69  3.000
 DOE  C5    N3   C4    113.43  3.000
 DOE  C15   N4   C7    109.56  3.000
 DOE  C15   N4   C6    109.68  3.000
 DOE  C7    N4   C6    112.54  3.000
 DOE  HN5   N5   C24   116.29  3.000
 DOE  HN5   N5   C21   114.84  3.000
 DOE  C24   N5   C21   128.59  3.000
 DOE  H10   O10  C27   108.63  3.000
 DOE  C26   S1   C25   103.93  3.000
 DOE  HC92  C9   HC91  104.85  3.000
 DOE  HC92  C9   N1    113.27  3.000
 DOE  HC91  C9   N1    108.66  3.000
 DOE  HC92  C9   C10   108.02  3.000
 DOE  HC91  C9   C10   105.35  3.000
 DOE  N1    C9   C10   115.84  3.000
 DOE  H112  C11  H111  105.23  3.000
 DOE  H112  C11  N2    108.19  3.000
 DOE  H111  C11  N2    112.45  3.000
 DOE  H112  C11  C12   105.88  3.000
 DOE  H111  C11  C12   108.13  3.000
 DOE  N2    C11  C12   116.21  3.000
 DOE  H132  C13  H131  104.84  3.000
 DOE  H132  C13  N3    107.70  3.000
 DOE  H131  C13  N3    113.67  3.000
 DOE  H132  C13  C14   106.77  3.000
 DOE  H131  C13  C14   107.39  3.000
 DOE  N3    C13  C14   115.71  3.000
 DOE  H152  C15  H151  104.87  3.000
 DOE  H152  C15  N4    111.21  3.000
 DOE  H151  C15  N4    108.83  3.000
 DOE  H152  C15  C16   108.57  3.000
 DOE  H151  C15  C16   105.65  3.000
 DOE  N4    C15  C16   116.91  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 DOE  CONST_01  C21   C20  C19  C18     0.00   0.0  0
 DOE  CONST_02  C21   C22  C23  C18     0.00   0.0  0
 DOE  CONST_03  C22   C23  C18  C19     0.00   0.0  0
 DOE  CONST_04  C22   C21  C20  C19     0.00   0.0  0
 DOE  CONST_05  C23   C18  C19  C20     0.00   0.0  0
 DOE  CONST_06  C23   C22  C21  C20     0.00   0.0  0
 DOE  CONST_07  C20   C19  C18  C17   180.00   0.0  0
 DOE  CONST_08  C22   C23  C18  C17   180.00   0.0  0
 DOE  CONST_09  N5    C21  C20  C19   180.00   0.0  0
 DOE  CONST_10  N5    C21  C22  C23   180.00   0.0  0
 DOE  CONST_11  H20   C20  C19  C18   180.00   0.0  0
 DOE  CONST_12  H22   C22  C23  C18   180.00   0.0  0
 DOE  CONST_13  H23   C23  C18  C19   180.00   0.0  0
 DOE  CONST_14  H19   C19  C20  C21   180.00   0.0  0
 DOE  CONST_18  C25   C24  N5   C21   180.00   0.0  0
 DOE  CONST_19  O9    C24  N5   C21     0.00   0.0  0
 DOE  Var_01    C3    N2   C2   C1   -113.78  30.0  1
 DOE  Var_02    C7    C8   N1   C1     73.90  30.0  1
 DOE  Var_03    C4    C3   N2   C2     74.91  30.0  1
 DOE  Var_04    C5    N3   C4   C3     77.05  30.0  1
 DOE  Var_05    C6    C5   N3   C4     89.30  30.0  1
 DOE  Var_06    C7    N4   C6   C5    -71.39  30.0  1
 DOE  Var_07    C8    C7   N4   C6    166.26  30.0  1
 DOE  Var_08    N4    C7   C8   N1   -124.17  30.0  1
 DOE  Var_09    N3    C4   C3   N2   -155.51  30.0  1
 DOE  Var_10    N4    C6   C5   N3    -68.84  30.0  1
 DOE  Var_11    C19   C18  C17  C1   -105.50  30.0  2
 DOE  Var_12    C10   C9   N1   C1    152.38  30.0  1
 DOE  Var_13    C12   C11  N2   C2   -162.92  30.0  2
 DOE  Var_14    C14   C13  N3   C4   -158.91  30.0  2
 DOE  Var_15    C16   C15  N4   C6    -71.09  30.0  1
 DOE  Var_16    O1    C10  C9   N1    -27.32  30.0  3
 DOE  Var_17    O3    C12  C11  N2     10.35  30.0  3
 DOE  Var_18    O5    C14  C13  N3      7.95  30.0  3
 DOE  Var_19    O7    C16  C15  N4    -19.93  30.0  3
 DOE  Var_20    C27   C26  S1   C25   -79.10  30.0  2
 DOE  Var_21    S1    C25  C24  N5    120.69  30.0  3
 DOE  Var_22    S1    C26  C27  O10    71.64  30.0  1
 DOE  Var_23    H251  C25  S1   C26   -14.64  30.0  1

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 DOE  chir_01  C1  C2  C17  N1  positiv

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 DOE  plan-1  C17  0.020
 DOE  plan-1  C18  0.020
 DOE  plan-1  C19  0.020
 DOE  plan-1  C20  0.020
 DOE  plan-1  C21  0.020
 DOE  plan-1  C22  0.020
 DOE  plan-1  C23  0.020
 DOE  plan-1  N5   0.020
 DOE  plan-1  H19  0.020
 DOE  plan-1  H20  0.020
 DOE  plan-1  H22  0.020
 DOE  plan-1  H23  0.020
 DOE  plan-2  C21  0.020
 DOE  plan-2  C24  0.020
 DOE  plan-2  C25  0.020
 DOE  plan-2  N5   0.020
 DOE  plan-2  O9   0.020
 DOE  plan-2  HN5  0.020
 DOE  plan-3  C10  0.020
 DOE  plan-3  O1   0.020
 DOE  plan-3  O2   0.020
 DOE  plan-3  C9   0.020
 DOE  plan-4  C12  0.020
 DOE  plan-4  O3   0.020
 DOE  plan-4  O4   0.020
 DOE  plan-4  C11  0.020
 DOE  plan-5  C14  0.020
 DOE  plan-5  O5   0.020
 DOE  plan-5  O6   0.020
 DOE  plan-5  C13  0.020
 DOE  plan-6  C16  0.020
 DOE  plan-6  O7   0.020
 DOE  plan-6  O8   0.020
 DOE  plan-6  C15  0.020

