# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Apr 25 07:39:23 2020
#   Inital geometry file: a 150 line input string
#   Ligand name: 3-[(6aS,7S,9S,10aS)-9-cyano-7-methyl-8-oxo-2-(phenylamino)-6,6a,7,8,9,10-hexahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H]1[C@@H]2CCc3cnc(Nc4ccccc4)nc3[C@]2(C[C@@H](C#N)C1=O)c5cccc(c5)C(O)=O
#
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
 DWS  DWS  '3-[(6aS,7S,9S,10aS)-9-cyano-7-methyl-8-oxo-2-(phenylamino)-6,6a,7,8,9,10-hexahydrobenzo[h]quinazolin-10a(5H)-yl]benzoic acid'  ligand  57  34  .  2022-07-24  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_DWS
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
 DWS  C4   C  C1     0  -0.322   2.2232   3.7587   0.8666
 DWS  C5   C  C1     0  -0.219   3.1918   2.7877   1.0580
 DWS  C6   C  C1     0  -0.332   2.9469   1.4658   0.7146
 DWS  C7   C  C      0   0.231   1.7212   1.0668   0.1715
 DWS  C8   C  CT     0  -0.233   1.4208  -0.3924  -0.2226
 DWS  C10  C  CH2    0  -0.444   2.2111  -0.0101  -2.5719
 DWS  C13  C  CR16   0  -0.027  -1.6050  -0.3063  -2.4702
 DWS  C15  C  CR6    0   0.586  -2.2296  -0.6661  -0.3407
 DWS  C17  C  CR6    0   0.265  -0.0029  -0.4514  -0.7666
 DWS  C20  C  C1     0  -0.355  -5.2009  -1.2853   1.7728
 DWS  C21  C  C1     0  -0.245  -6.5770  -1.4114   1.8265
 DWS  C22  C  C1     0  -0.280  -7.3453  -1.2533   0.6790
 DWS  C24  C  C1     0  -0.317  -5.3236  -0.8359  -0.5884
 DWS  C26  C  CH2    0  -0.399   1.4872  -1.3494   0.9840
 DWS  C34  C  CSP    0   0.161   2.8849  -2.7285   2.4555
 DWS  C23  C  C1     0  -0.244  -6.7050  -0.9667  -0.5169
 DWS  C36  C  C1     0  -0.348   0.7650   2.0694  -0.0044
 DWS  C3   C  C      0  -0.079   0.9938   3.4011   0.3292
 DWS  C12  C  CR6    0  -0.021  -0.2627  -0.2762  -2.1267
 DWS  C19  C  C      0   0.364  -4.5513  -0.9957   0.5654
 DWS  C29  C  C      0   0.467   3.7489  -2.1974   0.2308
 DWS  C2   C  C      0   0.403  -0.0954   4.4438   0.0976
 DWS  C11  C  CH2    0  -0.499   0.8078  -0.0998  -3.1638
 DWS  C27  C  CH1    0  -0.510   2.9196  -1.7134   1.4122
 DWS  C30  C  CH1    0  -0.382   3.7802  -1.2635  -0.9565
 DWS  C9   C  CH1    0  -0.222   2.3269  -0.9367  -1.3670
 DWS  C32  C  CH3    0  -0.664   4.5902  -1.8701  -2.0954
 DWS  N35  N  NS     0  -0.253   2.8312  -3.5197   3.2877
 DWS  N14  N  N      0  -0.460  -2.5909  -0.4917  -1.6063
 DWS  N16  N  N      0  -0.460  -0.9749  -0.6435   0.1075
 DWS  N18  N  NH1    0  -0.773  -3.1672  -0.8874   0.6239
 DWS  O37  O  OC    -1  -0.594   0.1900   5.6188   0.3974
 DWS  O33  O  O      0  -0.365   4.3115  -3.2620   0.2643
 DWS  O1   O  O      0  -0.586  -1.1729   4.0314  -0.3717
 DWS  H1   H  H      0   0.245   2.4217   4.7887   1.1304
 DWS  H2   H  H      0   0.253   4.1550   3.0538   1.4744
 DWS  H3   H  H      0   0.232   3.7552   0.7708   0.8741
 DWS  H4   H  HCH2   0   0.258   2.9263  -0.2737  -3.3495
 DWS  H5   H  HCH2   0   0.245   2.4457   1.0134  -2.2714
 DWS  H6   H  HCR6   0   0.268  -1.9006  -0.1687  -3.5065
 DWS  H9   H  H      0   0.251  -8.4219  -1.3502   0.7189
 DWS  H10  H  H      0   0.282  -4.8535  -0.6101  -1.5310
 DWS  H11  H  HCH2   0   0.288   0.9540  -0.9334   1.8367
 DWS  H12  H  HCH2   0   0.271   0.9795  -2.2775   0.7126
 DWS  H13  H  H      0   0.254  -7.2856  -0.8378  -1.4218
 DWS  H14  H  H      0   0.246  -0.2072   1.8463  -0.4170
 DWS  H15  H  HCH2   0   0.261   0.5992   0.7809  -3.7755
 DWS  H16  H  HCH2   0   0.255   0.7667  -0.9554  -3.8445
 DWS  H17  H  HCH1   0   0.354   3.4177  -0.8411   1.8456
 DWS  H18  H  HCH1   0   0.285   4.2820  -0.3446  -0.6340
 DWS  H19  H  HCH1   0   0.256   1.8875  -1.9040  -1.6533
 DWS  H20  H  HCH3   0   0.231   4.0970  -2.7500  -2.5102
 DWS  H21  H  HCH3   0   0.245   4.7278  -1.1517  -2.9001
 DWS  H22  H  HCH3   0   0.248   5.5816  -2.1649  -1.7560
 DWS  H23  H  HNH1   0   0.407  -2.7647  -1.0115   1.5407
 DWS  H7   H  H      0   0.266  -4.6152  -1.4148   2.6759
 DWS  H8   H  H      0   0.256  -7.0499  -1.6371   2.7736

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
 DWS  N35  C34  triple    1.150  0.020  1.150
 DWS  C34  C27  single    1.456  0.020  1.456
 DWS  C21  C20  aromatic  1.383  0.020  1.383
 DWS  C21  C22  aromatic  1.390  0.020  1.390
 DWS  C20  C19  aromatic  1.401  0.020  1.401
 DWS  C27  C26  single    1.539  0.020  1.539
 DWS  C27  C29  single    1.522  0.020  1.522
 DWS  C22  C23  aromatic  1.386  0.020  1.386
 DWS  C26  C8   single    1.541  0.020  1.541
 DWS  C19  N18  single    1.389  0.020  1.389
 DWS  C19  C24  aromatic  1.398  0.020  1.398
 DWS  N18  C15  single    1.363  0.020  1.363
 DWS  O33  C29  double    1.205  0.020  1.205
 DWS  C29  C30  single    1.511  0.020  1.511
 DWS  N16  C15  aromatic  1.333  0.020  1.333
 DWS  N16  C17  aromatic  1.321  0.020  1.321
 DWS  C15  N14  aromatic  1.328  0.020  1.328
 DWS  C23  C24  aromatic  1.389  0.020  1.389
 DWS  C6   C5   aromatic  1.388  0.020  1.388
 DWS  C6   C7   aromatic  1.399  0.020  1.399
 DWS  C8   C17  single    1.525  0.020  1.525
 DWS  C8   C7   single    1.541  0.020  1.541
 DWS  C8   C9   single    1.558  0.020  1.558
 DWS  C17  C12  aromatic  1.396  0.020  1.396
 DWS  N14  C13  aromatic  1.324  0.020  1.324
 DWS  C5   C4   aromatic  1.385  0.020  1.385
 DWS  C7   C36  aromatic  1.397  0.020  1.397
 DWS  C30  C9   single    1.545  0.020  1.545
 DWS  C30  C32  single    1.523  0.020  1.523
 DWS  C9   C10  single    1.524  0.020  1.524
 DWS  C12  C13  aromatic  1.386  0.020  1.386
 DWS  C12  C11  single    1.501  0.020  1.501
 DWS  C4   C3   aromatic  1.389  0.020  1.389
 DWS  C36  C3   aromatic  1.392  0.020  1.392
 DWS  C11  C10  single    1.526  0.020  1.526
 DWS  C3   C2   single    1.526  0.020  1.526
 DWS  C2   O1   deloc     1.245  0.020  1.245
 DWS  C2   O37  deloc     1.246  0.020  1.246
 DWS  C4   H1   single    0.930  0.020  1.080
 DWS  C5   H2   single    0.930  0.020  1.080
 DWS  C6   H3   single    0.930  0.020  1.080
 DWS  C10  H4   single    0.970  0.020  1.090
 DWS  C10  H5   single    0.970  0.020  1.090
 DWS  C13  H6   single    0.930  0.020  1.080
 DWS  C20  H7   single    0.930  0.020  1.080
 DWS  C21  H8   single    0.930  0.020  1.080
 DWS  C22  H9   single    0.930  0.020  1.080
 DWS  C24  H10  single    0.930  0.020  1.080
 DWS  C26  H11  single    0.970  0.020  1.090
 DWS  C26  H12  single    0.970  0.020  1.090
 DWS  C23  H13  single    0.930  0.020  1.080
 DWS  C36  H14  single    0.930  0.020  1.080
 DWS  C11  H15  single    0.970  0.020  1.090
 DWS  C11  H16  single    0.970  0.020  1.090
 DWS  C27  H17  single    0.970  0.020  1.090
 DWS  C30  H18  single    0.970  0.020  1.090
 DWS  C9   H19  single    0.970  0.020  1.090
 DWS  C32  H20  single    0.970  0.020  1.090
 DWS  C32  H21  single    0.970  0.020  1.090
 DWS  C32  H22  single    0.970  0.020  1.090
 DWS  N18  H23  single    0.860  0.020  1.020

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
 DWS  H1   C4   C3   120.14  3.000
 DWS  H1   C4   C5   120.38  3.000
 DWS  C3   C4   C5   119.48  3.000
 DWS  H2   C5   C6   119.10  3.000
 DWS  H2   C5   C4   120.21  3.000
 DWS  C6   C5   C4   120.69  3.000
 DWS  H3   C6   C7   122.05  3.000
 DWS  H3   C6   C5   116.44  3.000
 DWS  C7   C6   C5   121.50  3.000
 DWS  C36  C7   C8   120.94  3.000
 DWS  C36  C7   C6   116.36  3.000
 DWS  C8   C7   C6   122.70  3.000
 DWS  C9   C8   C26  109.45  3.000
 DWS  C9   C8   C17  105.51  3.000
 DWS  C26  C8   C17  107.18  3.000
 DWS  C9   C8   C7   113.91  3.000
 DWS  C17  C8   C7   108.04  3.000
 DWS  C26  C8   C7   112.29  3.000
 DWS  H5   C10  H4   106.40  3.000
 DWS  H5   C10  C9   109.63  3.000
 DWS  H4   C10  C9   111.56  3.000
 DWS  H5   C10  C11  111.06  3.000
 DWS  H4   C10  C11  108.23  3.000
 DWS  C9   C10  C11  109.92  3.000
 DWS  H6   C13  N14  115.95  3.000
 DWS  H6   C13  C12  119.81  3.000
 DWS  N14  C13  C12  124.23  3.000
 DWS  N18  C15  N16  114.35  3.000
 DWS  N16  C15  N14  125.07  3.000
 DWS  N18  C15  N14  120.57  3.000
 DWS  N16  C17  C12  121.73  3.000
 DWS  C12  C17  C8   121.10  3.000
 DWS  N16  C17  C8   117.15  3.000
 DWS  H7   C20  C19  119.47  3.000
 DWS  H7   C20  C21  119.63  3.000
 DWS  C19  C20  C21  120.91  3.000
 DWS  H8   C21  C22  120.31  3.000
 DWS  H8   C21  C20  119.19  3.000
 DWS  C22  C21  C20  120.50  3.000
 DWS  H9   C22  C23  120.66  3.000
 DWS  H9   C22  C21  120.63  3.000
 DWS  C23  C22  C21  118.71  3.000
 DWS  H10  C24  C19  120.34  3.000
 DWS  H10  C24  C23  119.91  3.000
 DWS  C19  C24  C23  119.75  3.000
 DWS  H12  C26  H11  106.96  3.000
 DWS  H12  C26  C27  107.51  3.000
 DWS  H11  C26  C27  109.17  3.000
 DWS  H12  C26  C8   108.25  3.000
 DWS  H11  C26  C8   110.79  3.000
 DWS  C27  C26  C8   113.88  3.000
 DWS  N35  C34  C27  180.00  3.000
 DWS  H13  C23  C24  118.61  3.000
 DWS  H13  C23  C22  119.86  3.000
 DWS  C24  C23  C22  121.53  3.000
 DWS  H14  C36  C3   115.94  3.000
 DWS  H14  C36  C7   121.09  3.000
 DWS  C3   C36  C7   122.97  3.000
 DWS  C2   C3   C36  120.01  3.000
 DWS  C2   C3   C4   120.99  3.000
 DWS  C36  C3   C4   119.00  3.000
 DWS  C11  C12  C17  123.73  3.000
 DWS  C11  C12  C13  121.47  3.000
 DWS  C17  C12  C13  114.78  3.000
 DWS  N18  C19  C24  125.19  3.000
 DWS  C24  C19  C20  118.60  3.000
 DWS  N18  C19  C20  116.21  3.000
 DWS  O33  C29  C30  123.95  3.000
 DWS  C30  C29  C27  115.13  3.000
 DWS  O33  C29  C27  120.92  3.000
 DWS  O1   C2   O37  126.95  3.000
 DWS  O37  C2   C3   116.40  3.000
 DWS  O1   C2   C3   116.65  3.000
 DWS  H16  C11  H15  105.95  3.000
 DWS  H16  C11  C12  108.14  3.000
 DWS  H15  C11  C12  110.21  3.000
 DWS  H16  C11  C10  108.78  3.000
 DWS  H15  C11  C10  110.21  3.000
 DWS  C12  C11  C10  113.26  3.000
 DWS  H17  C27  C29  108.23  3.000
 DWS  H17  C27  C34  106.43  3.000
 DWS  C29  C27  C34  110.33  3.000
 DWS  H17  C27  C26  110.21  3.000
 DWS  C29  C27  C26  111.49  3.000
 DWS  C34  C27  C26  110.01  3.000
 DWS  H18  C30  C32  108.09  3.000
 DWS  H18  C30  C9   109.37  3.000
 DWS  C32  C30  C9   112.69  3.000
 DWS  H18  C30  C29  107.25  3.000
 DWS  C32  C30  C29  110.63  3.000
 DWS  C9   C30  C29  108.66  3.000
 DWS  H19  C9   C30  105.00  3.000
 DWS  H19  C9   C10  107.36  3.000
 DWS  C30  C9   C10  114.20  3.000
 DWS  H19  C9   C8   105.43  3.000
 DWS  C10  C9   C8   108.91  3.000
 DWS  C30  C9   C8   115.20  3.000
 DWS  H22  C32  H21  107.12  3.000
 DWS  H22  C32  H20  108.17  3.000
 DWS  H21  C32  H20  107.99  3.000
 DWS  H22  C32  C30  111.04  3.000
 DWS  H21  C32  C30  110.94  3.000
 DWS  H20  C32  C30  111.42  3.000
 DWS  C15  N14  C13  115.97  3.000
 DWS  C17  N16  C15  118.20  3.000
 DWS  H23  N18  C19  115.22  3.000
 DWS  H23  N18  C15  112.86  3.000
 DWS  C19  N18  C15  131.91  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
 DWS  CONST_01  C7   C6   C5   C4      0.00   0.0  0
 DWS  CONST_02  C7   C36  C3   C4      0.00   0.0  0
 DWS  CONST_03  C36  C7   C6   C5      0.00   0.0  0
 DWS  CONST_04  C36  C3   C4   C5      0.00   0.0  0
 DWS  CONST_05  C3   C4   C5   C6      0.00   0.0  0
 DWS  CONST_06  C3   C36  C7   C6      0.00   0.0  0
 DWS  CONST_07  N16  C15  N14  C13     0.00   0.0  0
 DWS  CONST_08  N16  C17  C12  C13     0.00   0.0  0
 DWS  CONST_09  C12  C17  N16  C15     0.00   0.0  0
 DWS  CONST_10  C12  C13  N14  C15     0.00   0.0  0
 DWS  CONST_11  N14  C15  N16  C17     0.00   0.0  0
 DWS  CONST_12  N14  C13  C12  C17     0.00   0.0  0
 DWS  CONST_13  C23  C22  C21  C20     0.00   0.0  0
 DWS  CONST_14  C23  C24  C19  C20     0.00   0.0  0
 DWS  CONST_15  C24  C19  C20  C21     0.00   0.0  0
 DWS  CONST_16  C24  C23  C22  C21     0.00   0.0  0
 DWS  CONST_17  C19  C20  C21  C22     0.00   0.0  0
 DWS  CONST_18  C19  C24  C23  C22     0.00   0.0  0
 DWS  CONST_19  C8   C7   C6   C5    180.00   0.0  0
 DWS  CONST_20  C3   C36  C7   C8    180.00   0.0  0
 DWS  CONST_21  C2   C3   C4   C5    180.00   0.0  0
 DWS  CONST_22  C2   C3   C36  C7    180.00   0.0  0
 DWS  CONST_23  N18  C15  N14  C13   180.00   0.0  0
 DWS  CONST_24  N18  C15  N16  C17   180.00   0.0  0
 DWS  CONST_25  N18  C19  C20  C21   180.00   0.0  0
 DWS  CONST_26  N18  C19  C24  C23   180.00   0.0  0
 DWS  CONST_27  H3   C6   C5   C4    180.00   0.0  0
 DWS  CONST_28  H14  C36  C3   C4    180.00   0.0  0
 DWS  CONST_29  H1   C4   C5   C6    180.00   0.0  0
 DWS  CONST_30  H2   C5   C6   C7    180.00   0.0  0
 DWS  CONST_31  H6   C13  N14  C15   180.00   0.0  0
 DWS  CONST_32  H9   C22  C21  C20   180.00   0.0  0
 DWS  CONST_33  H10  C24  C19  C20   180.00   0.0  0
 DWS  CONST_34  H13  C23  C22  C21   180.00   0.0  0
 DWS  CONST_35  H7   C20  C21  C22   180.00   0.0  0
 DWS  CONST_36  H8   C21  C22  C23   180.00   0.0  0
 DWS  Var_01    C17  C12  C11  C10    -4.97  30.0  1
 DWS  Var_02    C9   C10  C11  C12    36.09  30.0  1
 DWS  Var_03    C20  C19  N18  C15   177.44  30.0  2
 DWS  Var_04    N16  C15  N18  C19  -179.20  30.0  2
 DWS  Var_05    O1   C2   C3   C4   -179.07  30.0  2

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
 DWS  chir_01  C8   C17  C7   C9   positiv
 DWS  chir_02  C27  C34  C26  C29  positiv
 DWS  chir_03  C30  C29  C9   C32  positiv
 DWS  chir_04  C9   C10  C30  C8   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
 DWS  plan-1  C4   0.020
 DWS  plan-1  C5   0.020
 DWS  plan-1  C6   0.020
 DWS  plan-1  C7   0.020
 DWS  plan-1  C8   0.020
 DWS  plan-1  C36  0.020
 DWS  plan-1  C3   0.020
 DWS  plan-1  C2   0.020
 DWS  plan-1  H1   0.020
 DWS  plan-1  H2   0.020
 DWS  plan-1  H3   0.020
 DWS  plan-1  H14  0.020
 DWS  plan-2  C20  0.020
 DWS  plan-2  C21  0.020
 DWS  plan-2  C22  0.020
 DWS  plan-2  C24  0.020
 DWS  plan-2  C23  0.020
 DWS  plan-2  C19  0.020
 DWS  plan-2  N18  0.020
 DWS  plan-2  H9   0.020
 DWS  plan-2  H10  0.020
 DWS  plan-2  H13  0.020
 DWS  plan-2  H7   0.020
 DWS  plan-2  H8   0.020
 DWS  plan-3  C8   0.020
 DWS  plan-3  C13  0.020
 DWS  plan-3  C15  0.020
 DWS  plan-3  C17  0.020
 DWS  plan-3  C12  0.020
 DWS  plan-3  C11  0.020
 DWS  plan-3  N14  0.020
 DWS  plan-3  N16  0.020
 DWS  plan-3  N18  0.020
 DWS  plan-3  H6   0.020
 DWS  plan-4  C29  0.020
 DWS  plan-4  C27  0.020
 DWS  plan-4  C30  0.020
 DWS  plan-4  O33  0.020
 DWS  plan-5  C3   0.020
 DWS  plan-5  C2   0.020
 DWS  plan-5  O37  0.020
 DWS  plan-5  O1   0.020

