# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 13:25:23 2020
#   Inital geometry file: a 121 line input string
#   Ligand name: (8beta)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(C2=C1)c34
#
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
 H8D  H8D  (8beta)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-9,10-didehydroergoline-8-carboxamide  ligand  50  25  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_H8D
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
 H8D  C4   C  CR16  0  -0.327   3.7902   2.9540  -0.4815
 H8D  C14  C  CH1   0  -0.442  -1.2981  -1.3212   0.2546
 H8D  C5   C  CR16  0  -0.263   2.4390   3.1971  -0.6879
 H8D  C6   C  CR66  0   0.135   1.8081   0.9066  -0.2100
 H8D  C11  C  CR16  0  -0.092   1.6005  -1.6226  -0.2260
 H8D  C7   C  CR56  0  -0.013   3.7678  -0.5511   0.3796
 H8D  C8   C  CR15  0  -0.099   5.1060  -0.2900   0.4572
 H8D  C9   C  CR6   0   0.041   0.9287  -0.2627  -0.0561
 H8D  C10  C  C1    0  -0.295  -0.3727  -0.1418   0.2063
 H8D  C13  C  CH2   0  -0.267  -0.6407  -2.4987  -0.4373
 H8D  N1   N  NR15  0  -0.697   5.3343   1.0351   0.1527
 H8D  N2   N  NT    0  -0.446   0.6892  -2.7090   0.1069
 H8D  C3   C  C     0  -0.029   3.1617   0.6687   0.0025
 H8D  N3   N  NH1   0  -0.625  -3.3808  -0.1310   0.3820
 H8D  C1   C  CR56  0   0.367   4.1493   1.6523  -0.1297
 H8D  C15  C  C     0  -0.534   2.8946  -1.7362   0.6193
 H8D  C16  C  C     0   0.571  -2.6206  -0.9247  -0.3900
 H8D  C19  C  CH1   0  -0.108  -4.5266   0.6158  -0.1038
 H8D  C2   C  CR16  0  -0.388   1.4544   2.2007  -0.5644
 H8D  C20  C  CH2   0  -0.445  -5.4717   0.9240   1.0543
 H8D  C21  C  CH3   0  -0.661  -6.0446  -0.3255   1.7077
 H8D  C22  C  CH2   0  -0.152  -4.0748   1.8646  -0.8512
 H8D  O1   O  O     0  -0.489  -2.9420  -1.2736  -1.5166
 H8D  O2   O  OH1   0  -0.670  -3.3008   2.6620   0.0149
 H8D  H1   H  HCR6  0   0.258   4.5213   3.7438  -0.5949
 H8D  H2   H  HCH1  0   0.285  -1.4979  -1.5845   1.3017
 H8D  H3   H  HCR6  0   0.249   2.1290   4.1951  -0.9699
 H8D  H4   H  HCR6  0   0.217   1.9058  -1.6885  -1.2892
 H8D  H5   H  HCR5  0   0.279   5.9329  -0.9363   0.7074
 H8D  H7   H  H     0   0.248  -0.7998   0.8439   0.3678
 H8D  H9   H  HCH3  0   0.242   2.1295  -4.2481   0.1901
 H8D  H10  H  HCH3  0   0.239   0.4794  -4.7752  -0.0595
 H8D  H11  H  HCH3  0   0.197   1.3813  -4.0557  -1.4013
 H8D  H12  H  HCH2  0   0.246  -1.2299  -3.4017  -0.2671
 H8D  H13  H  HCH2  0   0.208  -0.6178  -2.3308  -1.5248
 H8D  H14  H  HNR5  0   0.407   6.2426   1.4673   0.1399
 H8D  H16  H  HNH1  0   0.397  -3.0017   0.1533   1.2726
 H8D  H17  H  H     0   0.242   2.6048  -1.8016   1.6733
 H8D  H18  H  H     0   0.254   3.4167  -2.6614   0.3775
 H8D  H19  H  HCH1  0   0.251  -5.0591  -0.0135  -0.8213
 H8D  H20  H  HCR6  0   0.232   0.4230   2.4580  -0.7731
 H8D  H21  H  HCH2  0   0.229  -4.9606   1.5383   1.8009
 H8D  H22  H  HCH2  0   0.234  -6.2872   1.5379   0.6639
 H8D  H23  H  HCH3  0   0.220  -6.5610  -0.9496   0.9761
 H8D  H24  H  HCH3  0   0.223  -5.2681  -0.9342   2.1713
 H8D  H25  H  HCH3  0   0.232  -6.7623  -0.0630   2.4850
 H8D  H26  H  HCH2  0   0.211  -3.5020   1.5610  -1.7353
 H8D  H27  H  HCH2  0   0.201  -4.9655   2.3951  -1.2144
 H8D  H28  H  HOH1  0   0.457  -2.9031   3.3688  -0.5002
 H8D  C12  C  CH3   0  -0.534   1.1994  -3.9982  -0.3170

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
 H8D  C8   N1   aromatic  1.379  0.020  1.379
 H8D  C8   C7   aromatic  1.366  0.020  1.366
 H8D  N1   C1   aromatic  1.366  0.020  1.366
 H8D  C15  C7   single    1.491  0.020  1.491
 H8D  C15  C11  single    1.550  0.020  1.550
 H8D  C7   C3   aromatic  1.413  0.020  1.413
 H8D  C12  N2   single    1.450  0.020  1.450
 H8D  C1   C3   aromatic  1.400  0.020  1.400
 H8D  C1   C4   aromatic  1.395  0.020  1.395
 H8D  C3   C6   aromatic  1.391  0.020  1.391
 H8D  C11  N2   single    1.457  0.020  1.457
 H8D  C11  C9   single    1.526  0.020  1.526
 H8D  N2   C13  single    1.452  0.020  1.452
 H8D  C4   C5   aromatic  1.388  0.020  1.388
 H8D  C6   C9   single    1.471  0.020  1.471
 H8D  C6   C2   aromatic  1.388  0.020  1.388
 H8D  C9   C10  double    1.333  0.020  1.333
 H8D  C13  C14  single    1.516  0.020  1.516
 H8D  C5   C2   aromatic  1.406  0.020  1.406
 H8D  C10  C14  single    1.500  0.020  1.500
 H8D  C14  C16  single    1.524  0.020  1.524
 H8D  C16  N3   single    1.343  0.020  1.343
 H8D  C16  O1   double    1.222  0.020  1.222
 H8D  N3   C19  single    1.451  0.020  1.451
 H8D  C21  C20  single    1.522  0.020  1.522
 H8D  C20  C19  single    1.526  0.020  1.526
 H8D  C19  C22  single    1.524  0.020  1.524
 H8D  C22  O2   single    1.409  0.020  1.409
 H8D  C4   H1   single    0.930  0.020  1.080
 H8D  C14  H2   single    0.970  0.020  1.090
 H8D  C5   H3   single    0.930  0.020  1.080
 H8D  C11  H4   single    0.970  0.020  1.090
 H8D  C8   H5   single    0.930  0.020  1.080
 H8D  C10  H7   single    0.930  0.020  1.080
 H8D  C12  H9   single    0.970  0.020  1.090
 H8D  C12  H10  single    0.970  0.020  1.090
 H8D  C12  H11  single    0.970  0.020  1.090
 H8D  C13  H12  single    0.970  0.020  1.090
 H8D  C13  H13  single    0.970  0.020  1.090
 H8D  N1   H14  single    0.860  0.020  1.020
 H8D  N3   H16  single    0.860  0.020  1.020
 H8D  C15  H17  single    0.970  0.020  1.090
 H8D  C15  H18  single    0.970  0.020  1.090
 H8D  C19  H19  single    0.970  0.020  1.090
 H8D  C2   H20  single    0.930  0.020  1.080
 H8D  C20  H21  single    0.970  0.020  1.090
 H8D  C20  H22  single    0.970  0.020  1.090
 H8D  C21  H23  single    0.970  0.020  1.090
 H8D  C21  H24  single    0.970  0.020  1.090
 H8D  C21  H25  single    0.970  0.020  1.090
 H8D  C22  H26  single    0.970  0.020  1.090
 H8D  C22  H27  single    0.970  0.020  1.090
 H8D  O2   H28  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
 H8D  H1   C4   C1   122.23  3.000
 H8D  H1   C4   C5   120.94  3.000
 H8D  C1   C4   C5   116.83  3.000
 H8D  H2   C14  C16  107.93  3.000
 H8D  H2   C14  C13  109.15  3.000
 H8D  C16  C14  C13  112.67  3.000
 H8D  H2   C14  C10  109.36  3.000
 H8D  C16  C14  C10  108.49  3.000
 H8D  C13  C14  C10  109.19  3.000
 H8D  H3   C5   C2   118.40  3.000
 H8D  H3   C5   C4   118.62  3.000
 H8D  C2   C5   C4   122.98  3.000
 H8D  C2   C6   C3   116.53  3.000
 H8D  C2   C6   C9   128.00  3.000
 H8D  C3   C6   C9   115.46  3.000
 H8D  H4   C11  C15  106.79  3.000
 H8D  H4   C11  N2   110.33  3.000
 H8D  C15  C11  N2   110.07  3.000
 H8D  H4   C11  C9   106.32  3.000
 H8D  N2   C11  C9   111.33  3.000
 H8D  C15  C11  C9   111.84  3.000
 H8D  C15  C7   C3   118.53  3.000
 H8D  C3   C7   C8   105.69  3.000
 H8D  C15  C7   C8   135.76  3.000
 H8D  H5   C8   N1   120.01  3.000
 H8D  H5   C8   C7   130.52  3.000
 H8D  N1   C8   C7   109.48  3.000
 H8D  C10  C9   C11  122.17  3.000
 H8D  C10  C9   C6   122.14  3.000
 H8D  C11  C9   C6   115.69  3.000
 H8D  H7   C10  C9   119.69  3.000
 H8D  H7   C10  C14  117.79  3.000
 H8D  C9   C10  C14  122.50  3.000
 H8D  H13  C13  H12  106.95  3.000
 H8D  H13  C13  N2   111.92  3.000
 H8D  H12  C13  N2   108.43  3.000
 H8D  H13  C13  C14  109.97  3.000
 H8D  H12  C13  C14  109.72  3.000
 H8D  N2   C13  C14  109.79  3.000
 H8D  H14  N1   C1   125.92  3.000
 H8D  H14  N1   C8   124.42  3.000
 H8D  C1   N1   C8   109.66  3.000
 H8D  C13  N2   C12  109.97  3.000
 H8D  C13  N2   C11  112.29  3.000
 H8D  C12  N2   C11  112.10  3.000
 H8D  C1   C3   C7   109.21  3.000
 H8D  C1   C3   C6   123.50  3.000
 H8D  C7   C3   C6   127.28  3.000
 H8D  H16  N3   C19  116.56  3.000
 H8D  H16  N3   C16  117.47  3.000
 H8D  C19  N3   C16  123.95  3.000
 H8D  C3   C1   N1   105.96  3.000
 H8D  C3   C1   C4   119.84  3.000
 H8D  N1   C1   C4   134.19  3.000
 H8D  H18  C15  H17  106.84  3.000
 H8D  H18  C15  C7   111.01  3.000
 H8D  H17  C15  C7   110.92  3.000
 H8D  H18  C15  C11  109.96  3.000
 H8D  H17  C15  C11  107.96  3.000
 H8D  C7   C15  C11  110.06  3.000
 H8D  O1   C16  N3   123.34  3.000
 H8D  O1   C16  C14  122.95  3.000
 H8D  N3   C16  C14  113.70  3.000
 H8D  H19  C19  C22  107.12  3.000
 H8D  H19  C19  C20  108.22  3.000
 H8D  C22  C19  C20  112.97  3.000
 H8D  H19  C19  N3   107.95  3.000
 H8D  C22  C19  N3   110.60  3.000
 H8D  C20  C19  N3   109.80  3.000
 H8D  H20  C2   C6   120.89  3.000
 H8D  H20  C2   C5   118.78  3.000
 H8D  C6   C2   C5   120.32  3.000
 H8D  H22  C20  H21  106.09  3.000
 H8D  H22  C20  C21  109.49  3.000
 H8D  H21  C20  C21  110.12  3.000
 H8D  H22  C20  C19  107.72  3.000
 H8D  H21  C20  C19  110.01  3.000
 H8D  C21  C20  C19  113.15  3.000
 H8D  H25  C21  H24  107.46  3.000
 H8D  H25  C21  H23  107.71  3.000
 H8D  H24  C21  H23  107.62  3.000
 H8D  H25  C21  C20  110.88  3.000
 H8D  H24  C21  C20  111.89  3.000
 H8D  H23  C21  C20  111.09  3.000
 H8D  H27  C22  H26  106.90  3.000
 H8D  H27  C22  O2   112.05  3.000
 H8D  H26  C22  O2   111.43  3.000
 H8D  H27  C22  C19  108.52  3.000
 H8D  H26  C22  C19  108.87  3.000
 H8D  O2   C22  C19  108.98  3.000
 H8D  H28  O2   C22  108.32  3.000
 H8D  H11  C12  H10  107.73  3.000
 H8D  H11  C12  H9   107.80  3.000
 H8D  H10  C12  H9   106.90  3.000
 H8D  H11  C12  N2   113.11  3.000
 H8D  H10  C12  N2   109.41  3.000
 H8D  H9   C12  N2   111.63  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
 H8D  CONST_01  C8   N1   C1   C4    180.00   0.0  0
 H8D  CONST_02  C7   C3   C1   C4    180.00   0.0  0
 H8D  CONST_03  C6   C3   C1   C4      0.00   0.0  0
 H8D  CONST_04  C6   C2   C5   C4      0.00   0.0  0
 H8D  CONST_05  N1   C1   C4   C5    180.00   0.0  0
 H8D  CONST_06  C3   C1   C4   C5      0.00   0.0  0
 H8D  CONST_07  C3   C6   C2   C5      0.00   0.0  0
 H8D  CONST_08  C8   C7   C3   C6    180.00   0.0  0
 H8D  CONST_09  N1   C1   C3   C6    180.00   0.0  0
 H8D  CONST_10  C1   N1   C8   C7      0.00   0.0  0
 H8D  CONST_11  N1   C1   C3   C7      0.00   0.0  0
 H8D  CONST_12  C2   C6   C3   C7    180.00   0.0  0
 H8D  CONST_13  C3   C1   N1   C8      0.00   0.0  0
 H8D  CONST_14  C1   C3   C7   C8      0.00   0.0  0
 H8D  CONST_15  C3   C7   C8   N1      0.00   0.0  0
 H8D  CONST_16  C2   C6   C3   C1      0.00   0.0  0
 H8D  CONST_17  C2   C5   C4   C1      0.00   0.0  0
 H8D  CONST_18  H14  N1   C1   C4      0.00   0.0  0
 H8D  CONST_19  H20  C2   C5   C4    180.00   0.0  0
 H8D  CONST_20  H3   C5   C2   C6    180.00   0.0  0
 H8D  CONST_21  H1   C4   C1   N1      0.00   0.0  0
 H8D  CONST_22  H5   C8   C7   C3    180.00   0.0  0
 H8D  CONST_23  C19  N3   C16  C14   180.00   0.0  0
 H8D  CONST_24  H16  N3   C16  C14     0.00   0.0  0
 H8D  CONST_25  O1   C16  N3   C19     0.00   0.0  0
 H8D  Var_01    C11  N2   C13  C14   -67.57  30.0  1
 H8D  Var_02    C11  C9   C10  C14    -4.65  30.0  1
 H8D  Var_03    C8   C7   C15  C11  -154.09  30.0  1
 H8D  Var_04    C3   C6   C9   C11   -22.80  30.0  1
 H8D  Var_05    H9   C12  N2   C11    62.66  30.0  3
 H8D  Var_06    H23  C21  C20  C19   -56.58  30.0  3

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
 H8D  chir_01  C14  C13  C10  C16  negativ
 H8D  chir_02  C11  N2   C9   C15  negativ
 H8D  chir_03  C19  N3   C20  C22  negativ

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
 H8D  plan-1  C14  0.020
 H8D  plan-1  N3   0.020
 H8D  plan-1  C16  0.020
 H8D  plan-1  C19  0.020
 H8D  plan-1  O1   0.020
 H8D  plan-1  H16  0.020
 H8D  plan-2  C4   0.020
 H8D  plan-2  C5   0.020
 H8D  plan-2  C6   0.020
 H8D  plan-2  C7   0.020
 H8D  plan-2  C8   0.020
 H8D  plan-2  C9   0.020
 H8D  plan-2  N1   0.020
 H8D  plan-2  C3   0.020
 H8D  plan-2  C1   0.020
 H8D  plan-2  C15  0.020
 H8D  plan-2  C2   0.020
 H8D  plan-2  H1   0.020
 H8D  plan-2  H3   0.020
 H8D  plan-2  H5   0.020
 H8D  plan-2  H14  0.020
 H8D  plan-2  H20  0.020

