# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Mar  8 14:10:51 2022
#   Inital geometry file: a 123 line input string
#   Ligand name: (5beta)-11-hydroxyabieta-7,9(11),13-triene-6,12-dione
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)C1=CC2=CC(=O)[C@H]3C(C)(C)CCC[C@]3(C)C2=C(O)C1=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
 1WO  1WO  (5beta)-11-hydroxyabieta-7,9(11),13-triene-6,12-dione  ligand  49  23  .  2022-03-10  2022-03-10
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_1WO
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
 1WO  OAA  O  O     0  -0.421  -3.5308   1.7857  -0.1367
 1WO  CAB  C  CR6   0   0.313  -2.7205   0.8699  -0.0923
 1WO  CAC  C  CR6   0   0.228  -1.2844   1.2379  -0.2549
 1WO  OAD  O  OH1   0  -0.610  -1.1203   2.5356  -0.5061
 1WO  CAE  C  CR6   0   0.032  -0.2752   0.3391  -0.1704
 1WO  CAF  C  CT    0  -0.155   1.2076   0.6487  -0.4125
 1WO  CAG  C  CH3   0  -0.649   1.3933   0.6057  -1.9394
 1WO  CAH  C  CH2   0  -0.411   1.5992   2.0323   0.1397
 1WO  CAI  C  CH2   0  -0.447   3.0989   2.2879   0.1486
 1WO  CAJ  C  CH2   0  -0.404   3.8319   1.2379   0.9583
 1WO  CAK  C  CT    0  -0.066   3.6077  -0.1857   0.4336
 1WO  CAL  C  CH3   0  -0.665   4.3925  -0.3722  -0.8707
 1WO  CAM  C  CH3   0  -0.656   4.1951  -1.1452   1.4808
 1WO  CAN  C  CH1   0  -0.340   2.0754  -0.4208   0.3370
 1WO  CAO  C  C     0   0.425   1.6626  -1.8075  -0.0932
 1WO  OAP  O  O     0  -0.398   2.4147  -2.7085  -0.4095
 1WO  CAQ  C  C1    0  -0.437   0.2203  -2.0533  -0.0405
 1WO  CAR  C  CR6   0   0.200  -0.6808  -1.0480  -0.0239
 1WO  CAS  C  CR16  0  -0.366  -2.0802  -1.4179   0.0920
 1WO  CAT  C  CR6   0   0.046  -3.0874  -0.5322   0.0817
 1WO  CAU  C  CH1   0  -0.315  -4.5265  -0.9555   0.2184
 1WO  CAW  C  CH3   0  -0.650  -5.1843  -0.3879   1.4770
 1WO  CAV  C  CH3   0  -0.652  -5.3442  -0.6500  -1.0377
 1WO  H1   H  HOH1  0   0.472  -2.0059   2.9406  -0.4949
 1WO  H2   H  HCH3  0   0.244   0.7269   1.3287  -2.4113
 1WO  H3   H  HCH3  0   0.242   2.4068   0.8524  -2.2475
 1WO  H4   H  HCH3  0   0.234   1.1568  -0.3770  -2.3517
 1WO  H5   H  HCH2  0   0.252   1.1168   2.8156  -0.4388
 1WO  H6   H  HCH2  0   0.221   1.2259   2.1221   1.1658
 1WO  H7   H  HCH2  0   0.218   3.4868   2.3328  -0.8726
 1WO  H8   H  HCH2  0   0.237   3.2793   3.2780   0.5742
 1WO  H9   H  HCH2  0   0.226   4.9070   1.4412   0.9788
 1WO  H10  H  HCH2  0   0.217   3.4907   1.2944   1.9991
 1WO  H11  H  HCH3  0   0.239   4.1685  -1.3194  -1.3549
 1WO  H12  H  HCH3  0   0.224   4.2229   0.4239  -1.5926
 1WO  H13  H  HCH3  0   0.225   5.4615  -0.3625  -0.6444
 1WO  H14  H  HCH3  0   0.221   3.6033  -1.1443   2.3995
 1WO  H15  H  HCH3  0   0.239   4.2621  -2.1697   1.1215
 1WO  H16  H  HCH3  0   0.223   5.2054  -0.8220   1.7422
 1WO  H17  H  HCH1  0   0.274   1.7244  -0.3581   1.3796
 1WO  H18  H  H     0   0.283  -0.1084  -3.0863  -0.0240
 1WO  H19  H  HCR6  0   0.272  -2.2921  -2.4754   0.2032
 1WO  H20  H  HCH1  0   0.249  -4.5057  -2.0440   0.3303
 1WO  H21  H  HCH3  0   0.232  -6.1747  -0.8265   1.6069
 1WO  H22  H  HCH3  0   0.230  -4.6003  -0.6220   2.3679
 1WO  H23  H  HCH3  0   0.230  -5.3062   0.6926   1.4227
 1WO  H24  H  HCH3  0   0.231  -4.8825  -1.0844  -1.9251
 1WO  H25  H  HCH3  0   0.232  -6.3433  -1.0776  -0.9409
 1WO  H26  H  HCH3  0   0.230  -5.4555   0.4207  -1.2012

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
 1WO  CAV  CAU  single  1.530  0.020  1.530
 1WO  CAW  CAU  single  1.529  0.020  1.529
 1WO  CAU  CAT  single  1.506  0.020  1.506
 1WO  CAS  CAT  double  1.341  0.020  1.341
 1WO  CAS  CAR  single  1.452  0.020  1.452
 1WO  CAT  CAB  single  1.460  0.020  1.460
 1WO  CAQ  CAR  double  1.350  0.020  1.350
 1WO  CAQ  CAO  single  1.464  0.020  1.464
 1WO  CAR  CAE  single  1.453  0.020  1.453
 1WO  OAP  CAO  double  1.215  0.020  1.215
 1WO  CAB  OAA  double  1.224  0.020  1.224
 1WO  CAB  CAC  single  1.491  0.020  1.491
 1WO  CAO  CAN  single  1.509  0.020  1.509
 1WO  CAE  CAC  double  1.354  0.020  1.354
 1WO  CAE  CAF  single  1.534  0.020  1.534
 1WO  CAC  OAD  single  1.332  0.020  1.332
 1WO  CAN  CAF  single  1.568  0.020  1.568
 1WO  CAN  CAK  single  1.553  0.020  1.553
 1WO  CAF  CAG  single  1.539  0.020  1.539
 1WO  CAF  CAH  single  1.540  0.020  1.540
 1WO  CAL  CAK  single  1.534  0.020  1.534
 1WO  CAK  CAM  single  1.537  0.020  1.537
 1WO  CAK  CAJ  single  1.534  0.020  1.534
 1WO  CAH  CAI  single  1.521  0.020  1.521
 1WO  CAJ  CAI  single  1.515  0.020  1.515
 1WO  OAD  H1   single  0.850  0.020  0.980
 1WO  CAG  H2   single  0.970  0.020  1.090
 1WO  CAG  H3   single  0.970  0.020  1.090
 1WO  CAG  H4   single  0.970  0.020  1.090
 1WO  CAH  H5   single  0.970  0.020  1.090
 1WO  CAH  H6   single  0.970  0.020  1.090
 1WO  CAI  H7   single  0.970  0.020  1.090
 1WO  CAI  H8   single  0.970  0.020  1.090
 1WO  CAJ  H9   single  0.970  0.020  1.090
 1WO  CAJ  H10  single  0.970  0.020  1.090
 1WO  CAL  H11  single  0.970  0.020  1.090
 1WO  CAL  H12  single  0.970  0.020  1.090
 1WO  CAL  H13  single  0.970  0.020  1.090
 1WO  CAM  H14  single  0.970  0.020  1.090
 1WO  CAM  H15  single  0.970  0.020  1.090
 1WO  CAM  H16  single  0.970  0.020  1.090
 1WO  CAN  H17  single  0.970  0.020  1.090
 1WO  CAQ  H18  single  0.930  0.020  1.080
 1WO  CAS  H19  single  0.930  0.020  1.080
 1WO  CAU  H20  single  0.970  0.020  1.090
 1WO  CAW  H21  single  0.970  0.020  1.090
 1WO  CAW  H22  single  0.970  0.020  1.090
 1WO  CAW  H23  single  0.970  0.020  1.090
 1WO  CAV  H24  single  0.970  0.020  1.090
 1WO  CAV  H25  single  0.970  0.020  1.090
 1WO  CAV  H26  single  0.970  0.020  1.090

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
 1WO  CAT  CAB  CAC  119.48  3.000
 1WO  CAC  CAB  OAA  116.68  3.000
 1WO  CAT  CAB  OAA  123.83  3.000
 1WO  CAE  CAC  OAD  124.52  3.000
 1WO  OAD  CAC  CAB  112.31  3.000
 1WO  CAE  CAC  CAB  123.16  3.000
 1WO  H1   OAD  CAC  106.91  3.000
 1WO  CAR  CAE  CAF  118.59  3.000
 1WO  CAF  CAE  CAC  125.21  3.000
 1WO  CAR  CAE  CAC  115.60  3.000
 1WO  CAN  CAF  CAH  107.49  3.000
 1WO  CAH  CAF  CAG  110.50  3.000
 1WO  CAN  CAF  CAG  112.86  3.000
 1WO  CAH  CAF  CAE  111.74  3.000
 1WO  CAG  CAF  CAE  105.53  3.000
 1WO  CAN  CAF  CAE  108.77  3.000
 1WO  H4   CAG  H3   107.41  3.000
 1WO  H4   CAG  H2   107.52  3.000
 1WO  H3   CAG  H2   107.24  3.000
 1WO  H4   CAG  CAF  111.95  3.000
 1WO  H3   CAG  CAF  112.78  3.000
 1WO  H2   CAG  CAF  109.69  3.000
 1WO  H6   CAH  H5   106.75  3.000
 1WO  H6   CAH  CAI  108.46  3.000
 1WO  H5   CAH  CAI  108.64  3.000
 1WO  H6   CAH  CAF  108.83  3.000
 1WO  H5   CAH  CAF  110.10  3.000
 1WO  CAI  CAH  CAF  113.80  3.000
 1WO  H8   CAI  H7   105.54  3.000
 1WO  H8   CAI  CAJ  109.88  3.000
 1WO  H7   CAI  CAJ  110.86  3.000
 1WO  H8   CAI  CAH  108.50  3.000
 1WO  H7   CAI  CAH  110.56  3.000
 1WO  CAJ  CAI  CAH  111.32  3.000
 1WO  H10  CAJ  H9   106.15  3.000
 1WO  H10  CAJ  CAK  109.09  3.000
 1WO  H9   CAJ  CAK  108.81  3.000
 1WO  H10  CAJ  CAI  108.72  3.000
 1WO  H9   CAJ  CAI  110.88  3.000
 1WO  CAK  CAJ  CAI  112.94  3.000
 1WO  CAN  CAK  CAM  108.96  3.000
 1WO  CAM  CAK  CAL  107.94  3.000
 1WO  CAN  CAK  CAL  115.69  3.000
 1WO  CAM  CAK  CAJ  106.89  3.000
 1WO  CAL  CAK  CAJ  109.21  3.000
 1WO  CAN  CAK  CAJ  107.82  3.000
 1WO  H13  CAL  H12  106.46  3.000
 1WO  H13  CAL  H11  107.55  3.000
 1WO  H12  CAL  H11  108.06  3.000
 1WO  H13  CAL  CAK  108.87  3.000
 1WO  H12  CAL  CAK  113.30  3.000
 1WO  H11  CAL  CAK  112.30  3.000
 1WO  H16  CAM  H15  107.50  3.000
 1WO  H16  CAM  H14  107.42  3.000
 1WO  H15  CAM  H14  108.16  3.000
 1WO  H16  CAM  CAK  109.38  3.000
 1WO  H15  CAM  CAK  112.74  3.000
 1WO  H14  CAM  CAK  111.43  3.000
 1WO  H17  CAN  CAO  103.58  3.000
 1WO  H17  CAN  CAK  104.29  3.000
 1WO  CAO  CAN  CAK  115.25  3.000
 1WO  H17  CAN  CAF  103.72  3.000
 1WO  CAK  CAN  CAF  118.19  3.000
 1WO  CAO  CAN  CAF  109.81  3.000
 1WO  CAQ  CAO  OAP  119.63  3.000
 1WO  OAP  CAO  CAN  125.87  3.000
 1WO  CAQ  CAO  CAN  114.42  3.000
 1WO  H18  CAQ  CAR  120.46  3.000
 1WO  H18  CAQ  CAO  117.33  3.000
 1WO  CAR  CAQ  CAO  122.20  3.000
 1WO  CAS  CAR  CAQ  117.03  3.000
 1WO  CAQ  CAR  CAE  121.56  3.000
 1WO  CAS  CAR  CAE  121.36  3.000
 1WO  H19  CAS  CAT  119.87  3.000
 1WO  H19  CAS  CAR  116.42  3.000
 1WO  CAT  CAS  CAR  123.70  3.000
 1WO  CAU  CAT  CAS  122.08  3.000
 1WO  CAS  CAT  CAB  116.51  3.000
 1WO  CAU  CAT  CAB  121.39  3.000
 1WO  H20  CAU  CAV  107.02  3.000
 1WO  H20  CAU  CAW  107.05  3.000
 1WO  CAV  CAU  CAW  111.82  3.000
 1WO  H20  CAU  CAT  105.70  3.000
 1WO  CAW  CAU  CAT  112.42  3.000
 1WO  CAV  CAU  CAT  112.34  3.000
 1WO  H23  CAW  H22  108.28  3.000
 1WO  H23  CAW  H21  107.66  3.000
 1WO  H22  CAW  H21  107.61  3.000
 1WO  H23  CAW  CAU  112.05  3.000
 1WO  H22  CAW  CAU  111.24  3.000
 1WO  H21  CAW  CAU  109.83  3.000
 1WO  H26  CAV  H25  107.77  3.000
 1WO  H26  CAV  H24  108.23  3.000
 1WO  H25  CAV  H24  107.68  3.000
 1WO  H26  CAV  CAU  111.99  3.000
 1WO  H25  CAV  CAU  109.78  3.000
 1WO  H24  CAV  CAU  111.24  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
 1WO  Var_01  CAR  CAE  CAC  CAB     5.16   0.0  0
 1WO  Var_02  CAF  CAE  CAC  CAB   176.12   0.0  0
 1WO  Var_03  CAO  CAQ  CAR  CAE     5.24   0.0  0
 1WO  Var_04  CAJ  CAI  CAH  CAF   -57.76  30.0  1
 1WO  Var_05  CAK  CAJ  CAI  CAH    58.85  30.0  1
 1WO  Var_06  CAN  CAK  CAJ  CAI   -53.23  30.0  1
 1WO  Var_07  CAR  CAQ  CAO  CAN    19.71  30.0  1
 1WO  Var_08  CAV  CAU  CAT  CAB    63.41  30.0  3
 1WO  Var_09  H11  CAL  CAK  CAJ  -172.59  30.0  3
 1WO  Var_10  H14  CAM  CAK  CAJ    69.27  30.0  3
 1WO  Var_11  H24  CAV  CAU  CAT    54.22  30.0  3
 1WO  Var_12  H21  CAW  CAU  CAT  -172.30  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
 1WO  chir_01  CAF  CAN  CAE  CAH  negativ
 1WO  chir_02  CAN  CAK  CAF  CAO  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
 1WO  plan-1  CAN  0.020
 1WO  plan-1  CAO  0.020
 1WO  plan-1  OAP  0.020
 1WO  plan-1  CAQ  0.020
 1WO  plan-2  OAA  0.020
 1WO  plan-2  CAB  0.020
 1WO  plan-2  CAC  0.020
 1WO  plan-2  OAD  0.020
 1WO  plan-2  CAE  0.020
 1WO  plan-2  CAF  0.020
 1WO  plan-2  CAO  0.020
 1WO  plan-2  CAQ  0.020
 1WO  plan-2  CAR  0.020
 1WO  plan-2  CAS  0.020
 1WO  plan-2  CAT  0.020
 1WO  plan-2  CAU  0.020
 1WO  plan-2  H18  0.020
 1WO  plan-2  H19  0.020

