# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri May  8 03:42:31 2020
#   Inital geometry file: a 127 line input string
#   Ligand name: (1'R,2'R)-5'-methyl-6-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro[1,1'-biphenyl]-2,4-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCCCCc1cc(O)cc(O)c1[C@@H]2C=C(C)CC[C@H]2C(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
 HVD  HVD  (1'R,2'R)-5'-methyl-6-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro[1,1'-biphenyl]-2,4-diol  ligand  53  23  .  2021-08-11  2021-08-11  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_HVD
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
 HVD  C01  C  C     0   0.087  -1.2286  -2.7250  -1.6655
 HVD  C02  C  CH2   0  -0.488  -1.9836  -3.3962  -0.5534
 HVD  C03  C  CH2   0  -0.438  -1.5101  -2.9414   0.8184
 HVD  C04  C  CH1   0  -0.311  -1.4561  -1.4169   0.9100
 HVD  C05  C  CH1   0  -0.367  -0.4621  -0.8564  -0.1383
 HVD  C06  C  C1    0  -0.309  -0.5457  -1.5959  -1.4536
 HVD  C07  C  CH3   0  -0.713  -1.2803  -3.3868  -3.0066
 HVD  C08  C  CR6   0  -0.001  -0.6358   0.6382  -0.3334
 HVD  C09  C  C     0   0.205  -1.1030  -0.9302   2.2944
 HVD  C10  C  CH3   0  -0.744   0.0191  -1.6246   3.0106
 HVD  C11  C  C2    0  -0.580  -1.7571   0.0879   2.8484
 HVD  C12  C  CR6   0   0.117   0.2726   1.5749   0.1761
 HVD  C13  C  CR16  0  -0.482   0.0395   2.9400   0.0312
 HVD  C14  C  CR6   0   0.372  -1.0979   3.4019  -0.6184
 HVD  C15  C  CR16  0  -0.442  -2.0016   2.4940  -1.1477
 HVD  C16  C  CR6   0   0.327  -1.7659   1.1318  -1.0060
 HVD  O01  O  OH1   0  -0.641  -2.7051   0.3193  -1.5439
 HVD  O02  O  OH1   0  -0.639  -1.3637   4.7165  -0.7712
 HVD  C17  C  CH2   0  -0.554   1.5596   1.1680   0.8459
 HVD  C18  C  CH2   0  -0.414   2.6277   0.7245  -0.1560
 HVD  C19  C  CH2   0  -0.409   3.9519   0.3770   0.5105
 HVD  C20  C  CH2   0  -0.420   5.0079  -0.1024  -0.4780
 HVD  C21  C  CH3   0  -0.662   6.3413  -0.4174   0.1854
 HVD  H01  H  HCH2  0   0.245  -3.0561  -3.2023  -0.6749
 HVD  H02  H  HCH2  0   0.248  -1.8719  -4.4802  -0.6477
 HVD  H04  H  HCH2  0   0.242  -2.1734  -3.3368   1.5914
 HVD  H03  H  HCH2  0   0.230  -0.5186  -3.3610   1.0121
 HVD  H10  H  HCH1  0   0.237  -2.4543  -1.0340   0.6716
 HVD  H09  H  HCH1  0   0.264   0.5484  -1.0353   0.2400
 HVD  H08  H  H     0   0.249   0.0139  -1.1555  -2.2756
 HVD  H05  H  HCH3  0   0.240  -2.3134  -3.4951  -3.3464
 HVD  H06  H  HCH3  0   0.241  -0.7293  -2.8283  -3.7624
 HVD  H07  H  HCH3  0   0.240  -0.8637  -4.3954  -2.9538
 HVD  H11  H  HCH3  0   0.246   0.3064  -1.0881   3.9139
 HVD  H13  H  HCH3  0   0.249  -0.2623  -2.6391   3.3015
 HVD  H12  H  HCH3  0   0.230   0.9085  -1.7215   2.3833
 HVD  H15  H  H     0   0.225  -1.4984   0.4659   3.8304
 HVD  H14  H  H     0   0.226  -2.5708   0.5858   2.3352
 HVD  H16  H  HCR6  0   0.253   0.7557   3.6469   0.4370
 HVD  H17  H  HCR6  0   0.260  -2.8863   2.8363  -1.6710
 HVD  H29  H  HOH1  0   0.470  -2.3467  -0.5740  -1.6623
 HVD  H30  H  HOH1  0   0.472  -0.6600   5.2436  -0.3772
 HVD  H19  H  HCH2  0   0.247   1.9453   2.0185   1.4128
 HVD  H18  H  HCH2  0   0.248   1.3909   0.3769   1.5807
 HVD  H21  H  HCH2  0   0.219   2.2682  -0.1409  -0.7214
 HVD  H20  H  HCH2  0   0.224   2.7821   1.5209  -0.8902
 HVD  H23  H  HCH2  0   0.211   4.3284   1.2544   1.0474
 HVD  H22  H  HCH2  0   0.210   3.7876  -0.3963   1.2695
 HVD  H24  H  HCH2  0   0.211   4.6389  -0.9930  -0.9958
 HVD  H25  H  HCH2  0   0.212   5.1519   0.6589  -1.2510
 HVD  H26  H  HCH3  0   0.216   6.2266  -1.1856   0.9522
 HVD  H27  H  HCH3  0   0.226   7.0725  -0.7792  -0.5385
 HVD  H28  H  HCH3  0   0.216   6.7627   0.4669   0.6668

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
 HVD  O02  C14  single    1.350  0.020  1.350
 HVD  C14  C13  aromatic  1.389  0.020  1.389
 HVD  C14  C15  aromatic  1.386  0.020  1.386
 HVD  C13  C12  aromatic  1.392  0.020  1.392
 HVD  C15  C16  aromatic  1.390  0.020  1.390
 HVD  C12  C17  single    1.507  0.020  1.507
 HVD  C12  C08  aromatic  1.401  0.020  1.401
 HVD  C19  C20  single    1.524  0.020  1.524
 HVD  C19  C18  single    1.523  0.020  1.523
 HVD  C17  C18  single    1.530  0.020  1.530
 HVD  C16  C08  aromatic  1.405  0.020  1.405
 HVD  C16  O01  single    1.353  0.020  1.353
 HVD  C10  C09  single    1.501  0.020  1.501
 HVD  C08  C05  single    1.517  0.020  1.517
 HVD  C20  C21  single    1.522  0.020  1.522
 HVD  C09  C11  double    1.331  0.020  1.331
 HVD  C09  C04  single    1.509  0.020  1.509
 HVD  C05  C04  single    1.550  0.020  1.550
 HVD  C05  C06  single    1.511  0.020  1.511
 HVD  C04  C03  single    1.528  0.020  1.528
 HVD  C06  C01  double    1.337  0.020  1.337
 HVD  C03  C02  single    1.521  0.020  1.521
 HVD  C01  C02  single    1.502  0.020  1.502
 HVD  C01  C07  single    1.496  0.020  1.496
 HVD  C02  H01  single    0.970  0.020  1.090
 HVD  C02  H02  single    0.970  0.020  1.090
 HVD  C03  H04  single    0.970  0.020  1.090
 HVD  C03  H03  single    0.970  0.020  1.090
 HVD  C04  H10  single    0.970  0.020  1.090
 HVD  C05  H09  single    0.970  0.020  1.090
 HVD  C06  H08  single    0.930  0.020  1.080
 HVD  C07  H05  single    0.970  0.020  1.090
 HVD  C07  H06  single    0.970  0.020  1.090
 HVD  C07  H07  single    0.970  0.020  1.090
 HVD  C10  H11  single    0.970  0.020  1.090
 HVD  C10  H13  single    0.970  0.020  1.090
 HVD  C10  H12  single    0.970  0.020  1.090
 HVD  C11  H15  single    0.930  0.020  1.080
 HVD  C11  H14  single    0.930  0.020  1.080
 HVD  C13  H16  single    0.930  0.020  1.080
 HVD  C15  H17  single    0.930  0.020  1.080
 HVD  O01  H29  single    0.850  0.020  0.980
 HVD  O02  H30  single    0.850  0.020  0.980
 HVD  C17  H19  single    0.970  0.020  1.090
 HVD  C17  H18  single    0.970  0.020  1.090
 HVD  C18  H21  single    0.970  0.020  1.090
 HVD  C18  H20  single    0.970  0.020  1.090
 HVD  C19  H23  single    0.970  0.020  1.090
 HVD  C19  H22  single    0.970  0.020  1.090
 HVD  C20  H24  single    0.970  0.020  1.090
 HVD  C20  H25  single    0.970  0.020  1.090
 HVD  C21  H26  single    0.970  0.020  1.090
 HVD  C21  H27  single    0.970  0.020  1.090
 HVD  C21  H28  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
 HVD  C07  C01  C06  122.23  3.000
 HVD  C07  C01  C02  116.65  3.000
 HVD  C06  C01  C02  121.12  3.000
 HVD  H02  C02  H01  105.40  3.000
 HVD  H02  C02  C03  110.02  3.000
 HVD  H01  C02  C03  110.58  3.000
 HVD  H02  C02  C01  109.12  3.000
 HVD  H01  C02  C01  109.30  3.000
 HVD  C03  C02  C01  112.19  3.000
 HVD  H03  C03  H04  106.63  3.000
 HVD  H03  C03  C04  109.88  3.000
 HVD  H04  C03  C04  109.88  3.000
 HVD  H03  C03  C02  109.10  3.000
 HVD  H04  C03  C02  109.94  3.000
 HVD  C04  C03  C02  111.31  3.000
 HVD  H10  C04  C09  107.46  3.000
 HVD  H10  C04  C05  108.11  3.000
 HVD  C09  C04  C05  110.72  3.000
 HVD  H10  C04  C03  107.67  3.000
 HVD  C05  C04  C03  110.06  3.000
 HVD  C09  C04  C03  112.64  3.000
 HVD  H09  C05  C08  108.14  3.000
 HVD  H09  C05  C06  105.79  3.000
 HVD  C08  C05  C06  111.33  3.000
 HVD  H09  C05  C04  107.43  3.000
 HVD  C06  C05  C04  112.11  3.000
 HVD  C08  C05  C04  111.71  3.000
 HVD  H08  C06  C05  115.55  3.000
 HVD  H08  C06  C01  119.02  3.000
 HVD  C05  C06  C01  125.43  3.000
 HVD  H07  C07  H06  108.30  3.000
 HVD  H07  C07  H05  106.50  3.000
 HVD  H06  C07  H05  108.25  3.000
 HVD  H07  C07  C01  110.60  3.000
 HVD  H06  C07  C01  112.18  3.000
 HVD  H05  C07  C01  110.80  3.000
 HVD  C16  C08  C12  117.45  3.000
 HVD  C16  C08  C05  119.99  3.000
 HVD  C12  C08  C05  122.53  3.000
 HVD  C11  C09  C10  121.50  3.000
 HVD  C11  C09  C04  120.89  3.000
 HVD  C10  C09  C04  117.60  3.000
 HVD  H12  C10  H13  106.28  3.000
 HVD  H12  C10  H11  107.77  3.000
 HVD  H13  C10  H11  107.74  3.000
 HVD  H12  C10  C09  112.05  3.000
 HVD  H13  C10  C09  111.34  3.000
 HVD  H11  C10  C09  111.40  3.000
 HVD  H14  C11  H15  116.64  3.000
 HVD  H14  C11  C09  121.58  3.000
 HVD  H15  C11  C09  121.78  3.000
 HVD  C17  C12  C13  117.00  3.000
 HVD  C17  C12  C08  122.34  3.000
 HVD  C13  C12  C08  120.61  3.000
 HVD  H16  C13  C14  119.92  3.000
 HVD  H16  C13  C12  119.29  3.000
 HVD  C14  C13  C12  120.79  3.000
 HVD  O02  C14  C15  117.80  3.000
 HVD  C15  C14  C13  119.65  3.000
 HVD  O02  C14  C13  122.55  3.000
 HVD  H17  C15  C16  119.83  3.000
 HVD  H17  C15  C14  120.66  3.000
 HVD  C16  C15  C14  119.51  3.000
 HVD  O01  C16  C15  115.49  3.000
 HVD  O01  C16  C08  122.53  3.000
 HVD  C15  C16  C08  121.98  3.000
 HVD  H29  O01  C16  110.19  3.000
 HVD  H30  O02  C14  110.05  3.000
 HVD  H18  C17  H19  105.61  3.000
 HVD  H18  C17  C18  109.77  3.000
 HVD  H19  C17  C18  108.60  3.000
 HVD  H18  C17  C12  111.26  3.000
 HVD  H19  C17  C12  108.78  3.000
 HVD  C18  C17  C12  112.55  3.000
 HVD  H20  C18  H21  105.97  3.000
 HVD  H20  C18  C19  109.70  3.000
 HVD  H21  C18  C19  109.35  3.000
 HVD  H20  C18  C17  109.08  3.000
 HVD  H21  C18  C17  109.76  3.000
 HVD  C19  C18  C17  112.75  3.000
 HVD  H22  C19  H23  106.10  3.000
 HVD  H22  C19  C20  109.34  3.000
 HVD  H23  C19  C20  109.38  3.000
 HVD  H22  C19  C18  109.50  3.000
 HVD  H23  C19  C18  109.31  3.000
 HVD  C20  C19  C18  112.99  3.000
 HVD  H25  C20  H24  106.04  3.000
 HVD  H25  C20  C21  109.66  3.000
 HVD  H24  C20  C21  109.46  3.000
 HVD  H25  C20  C19  109.30  3.000
 HVD  H24  C20  C19  109.23  3.000
 HVD  C21  C20  C19  112.92  3.000
 HVD  H28  C21  H27  107.62  3.000
 HVD  H28  C21  H26  107.51  3.000
 HVD  H27  C21  H26  107.66  3.000
 HVD  H28  C21  C20  111.27  3.000
 HVD  H27  C21  C20  111.51  3.000
 HVD  H26  C21  C20  111.08  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
 HVD  CONST_01  C14  C13  C12  C08     0.00   0.0  0
 HVD  CONST_02  C14  C15  C16  C08     0.00   0.0  0
 HVD  CONST_03  C15  C14  C13  C12     0.00   0.0  0
 HVD  CONST_04  C15  C16  C08  C12     0.00   0.0  0
 HVD  CONST_05  C16  C15  C14  C13     0.00   0.0  0
 HVD  CONST_06  C16  C08  C12  C13     0.00   0.0  0
 HVD  CONST_07  C13  C12  C08  C05   180.00   0.0  0
 HVD  CONST_08  C15  C16  C08  C05   180.00   0.0  0
 HVD  CONST_09  C17  C12  C08  C05     0.00   0.0  0
 HVD  CONST_10  O01  C16  C08  C05     0.00   0.0  0
 HVD  CONST_11  O02  C14  C13  C12   180.00   0.0  0
 HVD  CONST_12  O01  C16  C08  C12   180.00   0.0  0
 HVD  CONST_13  C17  C12  C13  C14   180.00   0.0  0
 HVD  CONST_14  O01  C16  C15  C14   180.00   0.0  0
 HVD  CONST_15  O02  C14  C15  C16   180.00   0.0  0
 HVD  CONST_16  C17  C12  C08  C16   180.00   0.0  0
 HVD  CONST_17  H16  C13  C12  C08   180.00   0.0  0
 HVD  CONST_18  H17  C15  C16  C08   180.00   0.0  0
 HVD  Var_01    C04  C03  C02  C01    49.85  30.0  1
 HVD  Var_02    C05  C06  C01  C02    -1.20  30.0  1
 HVD  Var_03    C06  C01  C02  C03   -18.91  30.0  1
 HVD  Var_04    C18  C17  C12  C08    76.33  30.0  2
 HVD  Var_05    H05  C07  C01  C02    57.55  30.0  3
 HVD  Var_06    C19  C18  C17  C12   177.20  30.0  3
 HVD  Var_07    H15  C11  C09  C04  -178.36   0.0  2
 HVD  Var_08    H11  C10  C09  C04   169.84  30.0  3
 HVD  Var_09    C20  C19  C18  C17   178.40  30.0  2
 HVD  Var_10    C21  C20  C19  C18   178.62  30.0  3
 HVD  Var_11    H26  C21  C20  C19    58.64  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
 HVD  chir_01  C04  C09  C05  C03  negativ
 HVD  chir_02  C05  C06  C04  C08  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
 HVD  plan-1  C05  0.020
 HVD  plan-1  C08  0.020
 HVD  plan-1  C12  0.020
 HVD  plan-1  C13  0.020
 HVD  plan-1  C14  0.020
 HVD  plan-1  C15  0.020
 HVD  plan-1  C16  0.020
 HVD  plan-1  O01  0.020
 HVD  plan-1  O02  0.020
 HVD  plan-1  C17  0.020
 HVD  plan-1  H16  0.020
 HVD  plan-1  H17  0.020
 HVD  plan-2  C04  0.020
 HVD  plan-2  C09  0.020
 HVD  plan-2  C10  0.020
 HVD  plan-2  C11  0.020
 HVD  plan-2  H15  0.020
 HVD  plan-2  H14  0.020

