# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Mon May  4 12:10:08 2020
#   Inital geometry file: a 113 line input string
#   Ligand name: (2S,6S,11S)-6,11-dimethyl-3-(3-methylbut-2-en-1-yl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@@H]1[C@@H]2Cc3ccc(O)cc3[C@@]1(C)CCN2CC=C(C)C
#
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
 GM4  GM4  (2S,6S,11S)-6,11-dimethyl-3-(3-methylbut-2-en-1-yl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol  ligand  48  21  .  2021-08-10  2021-08-10  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_GM4
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
 GM4  C02  C  CH1   0  -0.202   0.0450   1.7355   0.6909
 GM4  C04  C  CH2   0  -0.518   0.3512  -0.4733   1.8084
 GM4  C05  C  CR6   0   0.049   1.5919  -0.6323   0.9684
 GM4  C06  C  CR6   0   0.158   1.8893   0.2259  -0.0966
 GM4  C11  C  CR16  0  -0.294   2.4938  -1.6461   1.2795
 GM4  C12  C  CT    0  -0.166   0.9053   1.3085  -0.5119
 GM4  C13  C  CH3   0  -0.676   1.5953   2.5286  -1.1231
 GM4  C14  C  CH2   0  -0.396  -0.0554   0.7152  -1.5586
 GM4  C15  C  CH2   0  -0.275  -0.9054  -0.4161  -1.0083
 GM4  C01  C  CH3   0  -0.673   0.8264   2.4657   1.7786
 GM4  C03  C  CH1   0  -0.095  -0.6789   0.5064   1.2365
 GM4  C07  C  CR16  0  -0.408   3.0668   0.0335  -0.8168
 GM4  C08  C  CR6   0   0.353   3.9546  -0.9857  -0.4955
 GM4  C10  C  CR16  0  -0.392   3.6660  -1.8349   0.5675
 GM4  C18  C  C1    0  -0.296  -3.6413  -1.2918  -0.2027
 GM4  C19  C  C     0   0.110  -4.6347  -0.4258  -0.4128
 GM4  C20  C  CH3   0  -0.712  -4.7148   0.9202   0.2420
 GM4  C21  C  CH3   0  -0.709  -5.7630  -0.7427  -1.3492
 GM4  N16  N  NT    0  -0.391  -1.5700  -0.0258   0.2169
 GM4  O09  O  OH1   0  -0.640   5.0759  -1.1079  -1.2426
 GM4  H1   H  HCH1  0   0.225  -0.7243   2.4150   0.3066
 GM4  H2   H  HCH2  0   0.252  -0.1054  -1.4522   1.9795
 GM4  H3   H  HCH2  0   0.249   0.6432  -0.1187   2.8028
 GM4  H4   H  HCR6  0   0.244   2.2754  -2.3139   2.1056
 GM4  H5   H  HCH3  0   0.235   2.4205   2.8908  -0.5091
 GM4  H6   H  HCH3  0   0.232   1.9899   2.3202  -2.1187
 GM4  H7   H  HCH3  0   0.234   0.8753   3.3425  -1.2296
 GM4  H8   H  HCH2  0   0.222  -0.7080   1.5181  -1.9172
 GM4  H9   H  HCH2  0   0.228   0.5122   0.3566  -2.4221
 GM4  H10  H  HCH2  0   0.237  -1.6701  -0.6730  -1.7459
 GM4  H11  H  HCH2  0   0.188  -0.2890  -1.3226  -0.8822
 GM4  H12  H  HCH3  0   0.236   1.1406   3.4543   1.4441
 GM4  H13  H  HCH3  0   0.230   0.2092   2.6034   2.6683
 GM4  H14  H  HCH3  0   0.223   1.7241   1.9241   2.0806
 GM4  H15  H  HCH1  0   0.232  -1.3218   0.8306   2.0626
 GM4  H16  H  HCR6  0   0.245   3.3122   0.6810  -1.6498
 GM4  H17  H  HCR6  0   0.262   4.3465  -2.6346   0.8390
 GM4  H18  H  HCH2  0   0.232  -2.8206  -0.7421   1.6975
 GM4  H19  H  HCH2  0   0.204  -1.9525  -2.0176   0.8683
 GM4  H20  H  H     0   0.227  -3.6700  -2.2412  -0.7297
 GM4  H21  H  HCH3  0   0.235  -4.5901   1.7122  -0.5010
 GM4  H22  H  HCH3  0   0.226  -5.7001   1.0682   0.6909
 GM4  H23  H  HCH3  0   0.246  -3.9592   1.0703   1.0095
 GM4  H24  H  HCH3  0   0.232  -5.8377   0.0089  -2.1395
 GM4  H25  H  HCH3  0   0.236  -5.6448  -1.7182  -1.8208
 GM4  H26  H  HCH3  0   0.232  -6.7214  -0.7336  -0.8234
 GM4  H28  H  HOH1  0   0.471   5.6168  -1.8314  -0.9083
 GM4  C17  C  CH2   0  -0.340  -2.4663  -1.0557   0.7100

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
 GM4  C21  C19  single    1.500  0.020  1.500
 GM4  C19  C20  single    1.499  0.020  1.499
 GM4  C19  C18  double    1.335  0.020  1.335
 GM4  C18  C17  single    1.506  0.020  1.506
 GM4  C17  N16  single    1.452  0.020  1.452
 GM4  N16  C15  single    1.447  0.020  1.447
 GM4  N16  C03  single    1.455  0.020  1.455
 GM4  C15  C14  single    1.518  0.020  1.518
 GM4  C03  C04  single    1.532  0.020  1.532
 GM4  C03  C02  single    1.527  0.020  1.527
 GM4  C04  C05  single    1.507  0.020  1.507
 GM4  C02  C01  single    1.525  0.020  1.525
 GM4  C02  C12  single    1.539  0.020  1.539
 GM4  C14  C12  single    1.540  0.020  1.540
 GM4  C12  C06  single    1.521  0.020  1.521
 GM4  C12  C13  single    1.529  0.020  1.529
 GM4  C05  C06  aromatic  1.400  0.020  1.400
 GM4  C05  C11  aromatic  1.392  0.020  1.392
 GM4  C06  C07  aromatic  1.394  0.020  1.394
 GM4  C11  C10  aromatic  1.384  0.020  1.384
 GM4  C07  C08  aromatic  1.389  0.020  1.389
 GM4  C10  C08  aromatic  1.391  0.020  1.391
 GM4  C08  O09  single    1.353  0.020  1.353
 GM4  C02  H1   single    0.970  0.020  1.090
 GM4  C04  H2   single    0.970  0.020  1.090
 GM4  C04  H3   single    0.970  0.020  1.090
 GM4  C11  H4   single    0.930  0.020  1.080
 GM4  C13  H5   single    0.970  0.020  1.090
 GM4  C13  H6   single    0.970  0.020  1.090
 GM4  C13  H7   single    0.970  0.020  1.090
 GM4  C14  H8   single    0.970  0.020  1.090
 GM4  C14  H9   single    0.970  0.020  1.090
 GM4  C15  H10  single    0.970  0.020  1.090
 GM4  C15  H11  single    0.970  0.020  1.090
 GM4  C01  H12  single    0.970  0.020  1.090
 GM4  C01  H13  single    0.970  0.020  1.090
 GM4  C01  H14  single    0.970  0.020  1.090
 GM4  C03  H15  single    0.970  0.020  1.090
 GM4  C07  H16  single    0.930  0.020  1.080
 GM4  C10  H17  single    0.930  0.020  1.080
 GM4  C17  H18  single    0.970  0.020  1.090
 GM4  C17  H19  single    0.970  0.020  1.090
 GM4  C18  H20  single    0.930  0.020  1.080
 GM4  C20  H21  single    0.970  0.020  1.090
 GM4  C20  H22  single    0.970  0.020  1.090
 GM4  C20  H23  single    0.970  0.020  1.090
 GM4  C21  H24  single    0.970  0.020  1.090
 GM4  C21  H25  single    0.970  0.020  1.090
 GM4  C21  H26  single    0.970  0.020  1.090
 GM4  O09  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
 GM4  H1   C02  C03  106.95  3.000
 GM4  H1   C02  C01  108.23  3.000
 GM4  C03  C02  C01  111.92  3.000
 GM4  H1   C02  C12  106.88  3.000
 GM4  C01  C02  C12  113.81  3.000
 GM4  C03  C02  C12  108.71  3.000
 GM4  H3   C04  H2   105.01  3.000
 GM4  H3   C04  C03  108.11  3.000
 GM4  H2   C04  C03  110.49  3.000
 GM4  H3   C04  C05  108.71  3.000
 GM4  H2   C04  C05  109.67  3.000
 GM4  C03  C04  C05  114.39  3.000
 GM4  C11  C05  C06  118.62  3.000
 GM4  C11  C05  C04  119.06  3.000
 GM4  C06  C05  C04  122.30  3.000
 GM4  C07  C06  C12  120.25  3.000
 GM4  C07  C06  C05  119.21  3.000
 GM4  C12  C06  C05  120.45  3.000
 GM4  H4   C11  C10  118.58  3.000
 GM4  H4   C11  C05  119.22  3.000
 GM4  C10  C11  C05  122.20  3.000
 GM4  C14  C12  C13  108.50  3.000
 GM4  C13  C12  C06  112.65  3.000
 GM4  C14  C12  C06  108.36  3.000
 GM4  C13  C12  C02  110.07  3.000
 GM4  C06  C12  C02  110.23  3.000
 GM4  C14  C12  C02  106.82  3.000
 GM4  H7   C13  H6   106.97  3.000
 GM4  H7   C13  H5   107.84  3.000
 GM4  H6   C13  H5   107.68  3.000
 GM4  H7   C13  C12  109.64  3.000
 GM4  H6   C13  C12  112.06  3.000
 GM4  H5   C13  C12  112.42  3.000
 GM4  H9   C14  H8   106.93  3.000
 GM4  H9   C14  C15  109.42  3.000
 GM4  H8   C14  C15  109.35  3.000
 GM4  H9   C14  C12  109.83  3.000
 GM4  H8   C14  C12  108.17  3.000
 GM4  C15  C14  C12  112.96  3.000
 GM4  H11  C15  H10  105.95  3.000
 GM4  H11  C15  N16  112.41  3.000
 GM4  H10  C15  N16  108.26  3.000
 GM4  H11  C15  C14  109.92  3.000
 GM4  H10  C15  C14  108.80  3.000
 GM4  N16  C15  C14  111.28  3.000
 GM4  H14  C01  H13  107.59  3.000
 GM4  H14  C01  H12  107.34  3.000
 GM4  H13  C01  H12  107.38  3.000
 GM4  H14  C01  C02  112.41  3.000
 GM4  H13  C01  C02  110.60  3.000
 GM4  H12  C01  C02  111.29  3.000
 GM4  H15  C03  N16  106.10  3.000
 GM4  H15  C03  C04  107.59  3.000
 GM4  N16  C03  C04  116.06  3.000
 GM4  H15  C03  C02  108.02  3.000
 GM4  C04  C03  C02  109.22  3.000
 GM4  N16  C03  C02  109.53  3.000
 GM4  H16  C07  C08  118.14  3.000
 GM4  H16  C07  C06  120.42  3.000
 GM4  C08  C07  C06  121.45  3.000
 GM4  O09  C08  C10  122.60  3.000
 GM4  O09  C08  C07  117.92  3.000
 GM4  C10  C08  C07  119.48  3.000
 GM4  H17  C10  C08  120.75  3.000
 GM4  H17  C10  C11  120.20  3.000
 GM4  C08  C10  C11  119.05  3.000
 GM4  H20  C18  C19  118.10  3.000
 GM4  H20  C18  C17  116.85  3.000
 GM4  C19  C18  C17  125.05  3.000
 GM4  C21  C19  C20  114.97  3.000
 GM4  C20  C19  C18  123.62  3.000
 GM4  C21  C19  C18  121.41  3.000
 GM4  H23  C20  H22  108.53  3.000
 GM4  H23  C20  H21  107.48  3.000
 GM4  H22  C20  H21  106.49  3.000
 GM4  H23  C20  C19  113.27  3.000
 GM4  H22  C20  C19  110.44  3.000
 GM4  H21  C20  C19  110.34  3.000
 GM4  H26  C21  H25  108.10  3.000
 GM4  H26  C21  H24  106.38  3.000
 GM4  H25  C21  H24  108.06  3.000
 GM4  H26  C21  C19  110.94  3.000
 GM4  H25  C21  C19  112.18  3.000
 GM4  H24  C21  C19  110.95  3.000
 GM4  C17  N16  C03  113.55  3.000
 GM4  C03  N16  C15  114.25  3.000
 GM4  C17  N16  C15  112.32  3.000
 GM4  H28  O09  C08  109.98  3.000
 GM4  H19  C17  H18  105.74  3.000
 GM4  H19  C17  N16  112.35  3.000
 GM4  H18  C17  N16  107.63  3.000
 GM4  H19  C17  C18  108.29  3.000
 GM4  H18  C17  C18  109.81  3.000
 GM4  N16  C17  C18  112.77  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
 GM4  CONST_01  C08  C07  C06  C05     0.00   0.0  0
 GM4  CONST_02  C08  C10  C11  C05     0.00   0.0  0
 GM4  CONST_03  C10  C11  C05  C06     0.00   0.0  0
 GM4  CONST_04  C10  C08  C07  C06     0.00   0.0  0
 GM4  CONST_05  C07  C06  C05  C11     0.00   0.0  0
 GM4  CONST_06  C07  C08  C10  C11     0.00   0.0  0
 GM4  CONST_07  O09  C08  C07  C06   180.00   0.0  0
 GM4  CONST_08  O09  C08  C10  C11   180.00   0.0  0
 GM4  CONST_09  H4   C11  C05  C04     0.00   0.0  0
 GM4  CONST_10  H16  C07  C06  C05   180.00   0.0  0
 GM4  CONST_11  H17  C10  C11  C05   180.00   0.0  0
 GM4  Var_01    C03  C04  C05  C06    11.67  30.0  1
 GM4  Var_02    N16  C15  C14  C12    51.47  30.0  3
 GM4  Var_03    C03  N16  C15  C14   -53.07  30.0  3
 GM4  Var_04    C18  C17  N16  C15   -66.22  30.0  1
 GM4  Var_05    N16  C17  C18  C19   -68.51  30.0  3
 GM4  Var_06    C21  C19  C18  C17   179.57   0.0  2
 GM4  Var_07    H24  C21  C19  C18  -122.18  30.0  3
 GM4  Var_08    H21  C20  C19  C18   112.58  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
 GM4  chir_01  C02  C03  C01  C12  negativ
 GM4  chir_02  C12  C06  C14  C02  negativ
 GM4  chir_03  C03  N16  C02  C04  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
 GM4  plan-1  C18  0.020
 GM4  plan-1  C19  0.020
 GM4  plan-1  C20  0.020
 GM4  plan-1  C21  0.020
 GM4  plan-1  H20  0.020
 GM4  plan-1  C17  0.020
 GM4  plan-2  C04  0.020
 GM4  plan-2  C05  0.020
 GM4  plan-2  C06  0.020
 GM4  plan-2  C11  0.020
 GM4  plan-2  C12  0.020
 GM4  plan-2  C07  0.020
 GM4  plan-2  C08  0.020
 GM4  plan-2  C10  0.020
 GM4  plan-2  O09  0.020
 GM4  plan-2  H4   0.020
 GM4  plan-2  H16  0.020
 GM4  plan-2  H17  0.020

