# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Jul 30 10:22:07 2022
#   Inital geometry file: a 118 line input string
#   Ligand name: (2E)-3-{7-[(1S)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1-methylnaphthalen-2-yl}prop-2-enoic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[C@H](Oc1ccc2ccc(\C=C\C(O)=O)c(C)c2c1)c3c(Cl)ccc(F)c3Cl
#
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
 95X  95X  "(2E)-3-{7-[(1S)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1-methylnaphthalen-2-yl}prop-2-enoic acid"  ligand  44  28  .  2022-09-16  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_95X
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
 95X  C12   C   CH1    0  -0.045  -26.8962  4.2633  -38.2986
 95X  C11   C   CR16   0  -0.294  -26.8422  3.2955  -33.6124
 95X  C10   C   CR16   0  -0.354  -27.2438  3.0337  -34.8893
 95X  C02   C   CR6    0  -0.001  -24.5453  6.2155  -34.1219
 95X  C03   C   CR6    0   0.098  -24.1480  6.4625  -32.8155
 95X  C04   C   CR16   0  -0.320  -24.6599  5.6512  -31.7658
 95X  C05   C   CR16   0  -0.310  -25.5258  4.6293  -32.0070
 95X  C06   C   CR66   0   0.065  -25.9409  4.3460  -33.3263
 95X  C07   C   CR66   0   0.146  -25.4466  5.1396  -34.3893
 95X  C08   C   CR16   0  -0.455  -25.8650  4.8400  -35.7099
 95X  C09   C   CR6    0   0.426  -26.7444  3.8149  -35.9563
 95X  C13   C   CH3    0  -0.661  -27.3704  3.5315  -39.5421
 95X  C14   C   CR6    0   0.255  -27.5189  5.6469  -38.1965
 95X  C15   C   CR6    0  -0.146  -28.8294  5.8666  -37.7680
 95X  C16   C   CR16   0  -0.170  -29.3697  7.1406  -37.6765
 95X  C17   C   CR16   0  -0.441  -28.6160  8.2460  -38.0251
 95X  C18   C   CR6    0   0.646  -27.3288  8.0495  -38.4705
 95X  C19   C   CR6    0  -0.327  -26.7864  6.7782  -38.5635
 95X  C21   C   C1     0  -0.424  -22.4297  7.5993  -31.3998
 95X  C22   C   C      0   0.401  -21.5021  8.7629  -31.1122
 95X  F01   F   F      0  -0.288  -26.5808  9.0950  -38.8179
 95X  O01   O   O2     0  -0.477  -27.1961  3.4577  -37.1773
 95X  O02   O   O      0  -0.595  -21.4719  9.6955  -31.9394
 95X  O03   O   OC    -1  -0.608  -20.8465  8.6703  -30.0541
 95X  CL01  CL  CL     0  -0.066  -25.1636  6.6689  -39.1416
 95X  CL02  CL  CL     0  -0.099  -29.8733  4.5537  -37.3358
 95X  H01   H   HCH1   0   0.259  -25.8112  4.3750  -38.3728
 95X  H09   H   HCR6   0   0.257  -27.2200  2.6942  -32.7943
 95X  H08   H   HCR6   0   0.265  -27.9390  2.2309  -35.1001
 95X  H02   H   HCH3   0   0.246  -24.8813  7.4689  -35.8414
 95X  H04   H   HCH3   0   0.260  -23.3864  7.8307  -35.0023
 95X  H03   H   HCH3   0   0.249  -23.5015  6.3972  -35.9965
 95X  H05   H   HCR6   0   0.245  -24.3710  5.8685  -30.7461
 95X  H06   H   HCR6   0   0.251  -25.9124  4.0322  -31.1897
 95X  H07   H   HCR6   0   0.264  -25.4662  5.4282  -36.5211
 95X  H12   H   HCH3   0   0.254  -26.8882  2.5568  -39.6123
 95X  H11   H   HCH3   0   0.240  -28.4498  3.3891  -39.5486
 95X  H10   H   HCH3   0   0.247  -27.0957  4.1062  -40.4257
 95X  H13   H   HCR6   0   0.297  -30.3869  7.2725  -37.3351
 95X  H14   H   HCR6   0   0.302  -29.0268  9.2443  -37.9565
 95X  H15   H   H      0   0.237  -23.1490  8.3817  -33.1635
 95X  H16   H   H      0   0.220  -22.4195  6.7855  -30.6801
 95X  C01   C   CH3    0  -0.771  -24.0510  7.0227  -35.2899
 95X  C20   C   C1     0  -0.278  -23.2151  7.5443  -32.4791

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
 95X  C13   C12   single    1.519  0.020  1.519
 95X  F01   C18   single    1.332  0.020  1.332
 95X  CL01  C19   single    1.726  0.020  1.726
 95X  C18   C19   aromatic  1.385  0.020  1.385
 95X  C18   C17   aromatic  1.376  0.020  1.376
 95X  C19   C14   aromatic  1.397  0.020  1.397
 95X  C17   C16   aromatic  1.383  0.020  1.383
 95X  C14   C12   single    1.521  0.020  1.521
 95X  C14   C15   aromatic  1.396  0.020  1.396
 95X  C16   C15   aromatic  1.387  0.020  1.387
 95X  C12   O01   single    1.413  0.020  1.413
 95X  C15   CL02  single    1.732  0.020  1.732
 95X  O01   C09   single    1.350  0.020  1.350
 95X  C09   C08   aromatic  1.373  0.020  1.373
 95X  C09   C10   aromatic  1.414  0.020  1.414
 95X  C08   C07   aromatic  1.417  0.020  1.417
 95X  C01   C02   single    1.503  0.020  1.503
 95X  C10   C11   aromatic  1.364  0.020  1.364
 95X  C07   C02   aromatic  1.429  0.020  1.429
 95X  C07   C06   aromatic  1.416  0.020  1.416
 95X  C02   C03   aromatic  1.388  0.020  1.388
 95X  C11   C06   aromatic  1.413  0.020  1.413
 95X  C06   C05   aromatic  1.412  0.020  1.412
 95X  C03   C20   single    1.468  0.020  1.468
 95X  C03   C04   aromatic  1.422  0.020  1.422
 95X  C20   C21   double    1.336  0.020  1.336
 95X  O02   C22   deloc     1.247  0.020  1.247
 95X  C05   C04   aromatic  1.361  0.020  1.361
 95X  C21   C22   single    1.516  0.020  1.516
 95X  C22   O03   deloc     1.248  0.020  1.248
 95X  C12   H01   single    0.970  0.020  1.090
 95X  C11   H09   single    0.930  0.020  1.080
 95X  C10   H08   single    0.930  0.020  1.080
 95X  C01   H02   single    0.970  0.020  1.090
 95X  C01   H04   single    0.970  0.020  1.090
 95X  C01   H03   single    0.970  0.020  1.090
 95X  C04   H05   single    0.930  0.020  1.080
 95X  C05   H06   single    0.930  0.020  1.080
 95X  C08   H07   single    0.930  0.020  1.080
 95X  C13   H12   single    0.970  0.020  1.090
 95X  C13   H11   single    0.970  0.020  1.090
 95X  C13   H10   single    0.970  0.020  1.090
 95X  C16   H13   single    0.930  0.020  1.080
 95X  C17   H14   single    0.930  0.020  1.080
 95X  C20   H15   single    0.930  0.020  1.080
 95X  C21   H16   single    0.930  0.020  1.080

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
 95X  H01   C12  O01  108.83  3.000
 95X  H01   C12  C14  108.54  3.000
 95X  O01   C12  C14  112.25  3.000
 95X  H01   C12  C13  107.67  3.000
 95X  O01   C12  C13  107.99  3.000
 95X  C14   C12  C13  111.44  3.000
 95X  H09   C11  C06  118.82  3.000
 95X  H09   C11  C10  119.85  3.000
 95X  C06   C11  C10  121.33  3.000
 95X  H08   C10  C09  119.32  3.000
 95X  H08   C10  C11  120.91  3.000
 95X  C09   C10  C11  119.77  3.000
 95X  C07   C02  C03  119.39  3.000
 95X  C03   C02  C01  122.80  3.000
 95X  C07   C02  C01  117.80  3.000
 95X  C20   C03  C04  118.70  3.000
 95X  C04   C03  C02  119.36  3.000
 95X  C20   C03  C02  121.94  3.000
 95X  H05   C04  C05  119.19  3.000
 95X  H05   C04  C03  119.01  3.000
 95X  C05   C04  C03  121.78  3.000
 95X  H06   C05  C06  119.31  3.000
 95X  H06   C05  C04  120.47  3.000
 95X  C06   C05  C04  120.22  3.000
 95X  C07   C06  C05  119.11  3.000
 95X  C05   C06  C11  121.72  3.000
 95X  C07   C06  C11  119.17  3.000
 95X  C08   C07  C06  118.56  3.000
 95X  C06   C07  C02  120.13  3.000
 95X  C08   C07  C02  121.31  3.000
 95X  H07   C08  C09  120.60  3.000
 95X  H07   C08  C07  118.46  3.000
 95X  C09   C08  C07  120.94  3.000
 95X  O01   C09  C08  125.05  3.000
 95X  C08   C09  C10  120.23  3.000
 95X  O01   C09  C10  114.72  3.000
 95X  H10   C13  H11  108.31  3.000
 95X  H10   C13  H12  107.94  3.000
 95X  H11   C13  H12  108.75  3.000
 95X  H10   C13  C12  109.34  3.000
 95X  H11   C13  C12  112.17  3.000
 95X  H12   C13  C12  110.21  3.000
 95X  C19   C14  C15  116.45  3.000
 95X  C15   C14  C12  123.24  3.000
 95X  C19   C14  C12  120.30  3.000
 95X  CL02  C15  C16  116.42  3.000
 95X  CL02  C15  C14  121.53  3.000
 95X  C16   C15  C14  122.04  3.000
 95X  H13   C16  C17  119.68  3.000
 95X  H13   C16  C15  119.96  3.000
 95X  C17   C16  C15  120.36  3.000
 95X  H14   C17  C18  120.50  3.000
 95X  H14   C17  C16  120.98  3.000
 95X  C18   C17  C16  118.51  3.000
 95X  F01   C18  C19  118.88  3.000
 95X  C19   C18  C17  121.27  3.000
 95X  F01   C18  C17  119.85  3.000
 95X  CL01  C19  C18  116.66  3.000
 95X  C18   C19  C14  121.35  3.000
 95X  CL01  C19  C14  121.98  3.000
 95X  H16   C21  C22  116.33  3.000
 95X  H16   C21  C20  120.65  3.000
 95X  C22   C21  C20  123.01  3.000
 95X  O03   C22  O02  127.24  3.000
 95X  O03   C22  C21  115.18  3.000
 95X  O02   C22  C21  117.59  3.000
 95X  C09   O01  C12  119.73  3.000
 95X  H03   C01  H04  106.85  3.000
 95X  H03   C01  H02  106.85  3.000
 95X  H04   C01  H02  107.17  3.000
 95X  H03   C01  C02  111.14  3.000
 95X  H04   C01  C02  113.28  3.000
 95X  H02   C01  C02  111.21  3.000
 95X  H15   C20  C21  116.27  3.000
 95X  H15   C20  C03  117.63  3.000
 95X  C21   C20  C03  126.10  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
 95X  CONST_01  C08   C09  C10  C11     0.00   0.0  0
 95X  CONST_02  C08   C07  C06  C11     0.00   0.0  0
 95X  CONST_03  C02   C07  C06  C11   180.00   0.0  0
 95X  CONST_04  C04   C05  C06  C11   180.00   0.0  0
 95X  CONST_05  C07   C08  C09  C10     0.00   0.0  0
 95X  CONST_06  C07   C06  C11  C10     0.00   0.0  0
 95X  CONST_07  C05   C06  C11  C10   180.00   0.0  0
 95X  CONST_08  C09   C08  C07  C02   180.00   0.0  0
 95X  CONST_09  C05   C06  C07  C02     0.00   0.0  0
 95X  CONST_10  C05   C04  C03  C02     0.00   0.0  0
 95X  CONST_11  C08   C07  C02  C03   180.00   0.0  0
 95X  CONST_12  C06   C07  C02  C03     0.00   0.0  0
 95X  CONST_13  C06   C05  C04  C03     0.00   0.0  0
 95X  CONST_14  C07   C02  C03  C04     0.00   0.0  0
 95X  CONST_15  C07   C06  C05  C04     0.00   0.0  0
 95X  CONST_16  C08   C07  C06  C05   180.00   0.0  0
 95X  CONST_17  C09   C08  C07  C06     0.00   0.0  0
 95X  CONST_18  C09   C10  C11  C06     0.00   0.0  0
 95X  CONST_19  C17   C18  C19  C14     0.00   0.0  0
 95X  CONST_20  C17   C16  C15  C14     0.00   0.0  0
 95X  CONST_21  C18   C19  C14  C15     0.00   0.0  0
 95X  CONST_22  C18   C17  C16  C15     0.00   0.0  0
 95X  CONST_23  C19   C18  C17  C16     0.00   0.0  0
 95X  CONST_24  C19   C14  C15  C16     0.00   0.0  0
 95X  CONST_25  C18   C19  C14  C12   180.00   0.0  0
 95X  CONST_26  C16   C15  C14  C12   180.00   0.0  0
 95X  CONST_27  O01   C09  C10  C11   180.00   0.0  0
 95X  CONST_28  C08   C07  C02  C01     0.00   0.0  0
 95X  CONST_29  C06   C07  C02  C01   180.00   0.0  0
 95X  CONST_30  C04   C03  C02  C01   180.00   0.0  0
 95X  CONST_31  C20   C03  C04  C05   180.00   0.0  0
 95X  CONST_32  O01   C09  C08  C07   180.00   0.0  0
 95X  CONST_33  C20   C03  C02  C07   180.00   0.0  0
 95X  CONST_34  F01   C18  C19  C14   180.00   0.0  0
 95X  CONST_35  CL01  C19  C14  C15   180.00   0.0  0
 95X  CONST_36  F01   C18  C17  C16   180.00   0.0  0
 95X  CONST_37  CL01  C19  C18  C17   180.00   0.0  0
 95X  CONST_38  CL02  C15  C16  C17   180.00   0.0  0
 95X  CONST_39  CL02  C15  C14  C19   180.00   0.0  0
 95X  CONST_40  H06   C05  C06  C11     0.00   0.0  0
 95X  CONST_41  H07   C08  C09  C10   180.00   0.0  0
 95X  CONST_42  H07   C08  C07  C02     0.00   0.0  0
 95X  CONST_43  H05   C04  C03  C02   180.00   0.0  0
 95X  CONST_44  H06   C05  C04  C03   180.00   0.0  0
 95X  CONST_45  H09   C11  C06  C05     0.00   0.0  0
 95X  CONST_46  H07   C08  C07  C06   180.00   0.0  0
 95X  CONST_47  H08   C10  C11  C06   180.00   0.0  0
 95X  CONST_48  H05   C04  C05  C06   180.00   0.0  0
 95X  CONST_49  H09   C11  C06  C07   180.00   0.0  0
 95X  CONST_50  H06   C05  C06  C07   180.00   0.0  0
 95X  CONST_51  H08   C10  C09  C08   180.00   0.0  0
 95X  CONST_52  H09   C11  C10  C09   180.00   0.0  0
 95X  CONST_53  H13   C16  C15  C14   180.00   0.0  0
 95X  CONST_54  H14   C17  C16  C15   180.00   0.0  0
 95X  CONST_55  H13   C16  C17  C18   180.00   0.0  0
 95X  CONST_56  H14   C17  C18  C19   180.00   0.0  0
 95X  Var_01    C08   C09  O01  C12    -8.01  30.0  2
 95X  Var_02    C10   C09  O01  C12   172.34  30.0  2
 95X  Var_03    C21   C20  C03  C02  -155.63  30.0  2
 95X  Var_04    C21   C20  C03  C04    24.64  30.0  2
 95X  Var_05    H15   C20  C03  C02    24.36  30.0  2
 95X  Var_06    H02   C01  C02  C03  -122.79  30.0  2
 95X  Var_07    H04   C01  C02  C03    -2.01  30.0  2
 95X  Var_08    H03   C01  C02  C03   118.30  30.0  2
 95X  Var_09    H15   C20  C03  C04  -155.38  30.0  2
 95X  Var_10    H02   C01  C02  C07    58.16  30.0  2
 95X  Var_11    H04   C01  C02  C07   178.94  30.0  2
 95X  Var_12    H03   C01  C02  C07   -60.75  30.0  2
 95X  Var_13    C22   C21  C20  C03  -179.21   0.0  2
 95X  Var_14    H16   C21  C20  C03     1.61   0.0  2
 95X  Var_15    O02   C22  C21  C20    -0.86  30.0  2
 95X  Var_16    O03   C22  C21  C20   179.16  30.0  2
 95X  Var_17    H15   C20  C21  C22     0.81   0.0  2
 95X  Var_18    H16   C21  C22  O02   178.35  30.0  2
 95X  Var_19    H16   C21  C22  O03    -1.62  30.0  2
 95X  Var_20    H16   C21  C20  H15  -178.37   0.0  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
 95X  chir_01  C12  C13  C14  O01  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
 95X  plan-1  C12   0.020
 95X  plan-1  C14   0.020
 95X  plan-1  C15   0.020
 95X  plan-1  C16   0.020
 95X  plan-1  C17   0.020
 95X  plan-1  C18   0.020
 95X  plan-1  C19   0.020
 95X  plan-1  F01   0.020
 95X  plan-1  CL01  0.020
 95X  plan-1  CL02  0.020
 95X  plan-1  H13   0.020
 95X  plan-1  H14   0.020
 95X  plan-2  C11   0.020
 95X  plan-2  C10   0.020
 95X  plan-2  C02   0.020
 95X  plan-2  C03   0.020
 95X  plan-2  C04   0.020
 95X  plan-2  C05   0.020
 95X  plan-2  C06   0.020
 95X  plan-2  C07   0.020
 95X  plan-2  C08   0.020
 95X  plan-2  C09   0.020
 95X  plan-2  O01   0.020
 95X  plan-2  H09   0.020
 95X  plan-2  H08   0.020
 95X  plan-2  H05   0.020
 95X  plan-2  H06   0.020
 95X  plan-2  H07   0.020
 95X  plan-2  C01   0.020
 95X  plan-2  C20   0.020
 95X  plan-3  C21   0.020
 95X  plan-3  C22   0.020
 95X  plan-3  O02   0.020
 95X  plan-3  O03   0.020
 95X  plan-4  C03   0.020
 95X  plan-4  C21   0.020
 95X  plan-4  C22   0.020
 95X  plan-4  H15   0.020
 95X  plan-4  H16   0.020
 95X  plan-4  C20   0.020

