# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat Mar 21 20:54:00 2020
#   Inital geometry file: a 86 line input string
#   Ligand name: 3-(3-fluoro-4-hydroxyphenyl)-7-hydroxynaphthalene-1-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1ccc2cc(cc(C#N)c2c1)c3ccc(O)c(F)c3
#
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
 196  196  3-(3-fluoro-4-hydroxyphenyl)-7-hydroxynaphthalene-1-carbonitrile  ligand  31  21  .  2021-08-03  2021-08-03  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_196
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
 196  C1   C  CR6   0   0.218  -4.6593  -0.3706  -0.2144
 196  C2   C  CR6   0   0.463  -3.9768   0.6978   0.3604
 196  C3   C  CR16  0  -0.473  -2.6045   0.7529   0.4256
 196  C4   C  CR6   0   0.091  -1.8408  -0.2889  -0.1027
 196  C5   C  CR16  0  -0.311  -2.5122  -1.3652  -0.6822
 196  C6   C  CR16  0  -0.329  -3.8954  -1.4074  -0.7379
 196  O10  O  OH1   0  -0.623  -5.9983  -0.4403  -0.2808
 196  F11  F  F     0  -0.321  -4.7061   1.7035   0.8814
 196  C12  C  CR6   0   0.100  -0.3686  -0.2430  -0.0489
 196  C13  C  CR16  0  -0.373   0.3233   0.9437  -0.1585
 196  C14  C  CR66  0   0.110   1.7277   0.9989  -0.1006
 196  C15  C  CR66  0   0.176   2.4811  -0.1892   0.0686
 196  C16  C  CR6   0   0.002   1.7495  -1.4052   0.1750
 196  C17  C  CR16  0  -0.321   0.3747  -1.4277   0.1199
 196  C20  C  CR16  0  -0.295   2.4225   2.2277  -0.2168
 196  C21  C  CR16  0  -0.330   3.7826   2.2759  -0.1602
 196  C22  C  CR6   0   0.400   4.5276   1.0843   0.0145
 196  C23  C  CR16  0  -0.484   3.8865  -0.1268   0.1249
 196  C27  C  CSP   0   0.013   2.4472  -2.6344   0.3558
 196  N28  N  NS    0  -0.249   3.0170  -3.6263   0.5001
 196  O29  O  OH1   0  -0.622   5.8601   1.2192   0.0610
 196  H3   H  HCR6  0   0.282  -2.1384   1.6020   0.9095
 196  H5   H  HCR6  0   0.263  -1.9540  -2.1822  -1.1202
 196  H6   H  HCR6  0   0.280  -4.3957  -2.2491  -1.1993
 196  H10  H  HOH1  0   0.479  -6.4111   0.3433   0.1007
 196  H13  H  HCR6  0   0.269  -0.2157   1.8712  -0.3138
 196  H17  H  HCR6  0   0.284  -0.1392  -2.3741   0.2283
 196  H20  H  HCR6  0   0.270   1.8543   3.1394  -0.3526
 196  H21  H  HCR6  0   0.278   4.3066   3.2191  -0.2480
 196  H23  H  HCR6  0   0.271   4.4662  -1.0341   0.2555
 196  H29  H  HOH1  0   0.481   6.2866   0.3658   0.2026

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
 196  C1   C2   aromatic  1.392  0.020  1.392
 196  C1   C6   aromatic  1.390  0.020  1.390
 196  C1   O10  single    1.342  0.020  1.342
 196  C2   C3   aromatic  1.375  0.020  1.375
 196  C2   F11  single    1.347  0.020  1.347
 196  C3   C4   aromatic  1.396  0.020  1.396
 196  C3   H3   single    0.930  0.020  1.080
 196  C4   C5   aromatic  1.395  0.020  1.395
 196  C4   C12  single    1.474  0.020  1.474
 196  C5   C6   aromatic  1.385  0.020  1.385
 196  C5   H5   single    0.930  0.020  1.080
 196  C6   H6   single    0.930  0.020  1.080
 196  O10  H10  single    0.850  0.020  0.980
 196  C12  C13  aromatic  1.378  0.020  1.378
 196  C12  C17  aromatic  1.409  0.020  1.409
 196  C13  C14  aromatic  1.407  0.020  1.407
 196  C13  H13  single    0.930  0.020  1.080
 196  C14  C15  aromatic  1.417  0.020  1.417
 196  C14  C20  aromatic  1.416  0.020  1.416
 196  C15  C16  aromatic  1.423  0.020  1.423
 196  C15  C23  aromatic  1.408  0.020  1.408
 196  C16  C17  aromatic  1.376  0.020  1.376
 196  C16  C27  single    1.425  0.020  1.425
 196  C17  H17  single    0.930  0.020  1.080
 196  C20  C21  aromatic  1.362  0.020  1.362
 196  C20  H20  single    0.930  0.020  1.080
 196  C21  C22  aromatic  1.416  0.020  1.416
 196  C21  H21  single    0.930  0.020  1.080
 196  C22  C23  aromatic  1.375  0.020  1.375
 196  C22  O29  single    1.340  0.020  1.340
 196  C23  H23  single    0.930  0.020  1.080
 196  C27  N28  triple    1.153  0.020  1.153
 196  O29  H29  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
 196  O10  C1   C6   119.39  3.000
 196  O10  C1   C2   123.32  3.000
 196  C6   C1   C2   117.29  3.000
 196  F11  C2   C3   119.48  3.000
 196  F11  C2   C1   117.85  3.000
 196  C3   C2   C1   122.66  3.000
 196  H3   C3   C4   121.27  3.000
 196  H3   C3   C2   118.83  3.000
 196  C4   C3   C2   119.89  3.000
 196  C12  C4   C5   121.34  3.000
 196  C12  C4   C3   120.63  3.000
 196  C5   C4   C3   118.03  3.000
 196  H5   C5   C6   118.42  3.000
 196  H5   C5   C4   120.17  3.000
 196  C6   C5   C4   121.40  3.000
 196  H6   C6   C5   120.16  3.000
 196  H6   C6   C1   119.11  3.000
 196  C5   C6   C1   120.73  3.000
 196  H10  O10  C1   111.42  3.000
 196  C17  C12  C13  117.96  3.000
 196  C17  C12  C4   120.34  3.000
 196  C13  C12  C4   121.69  3.000
 196  H13  C13  C14  117.95  3.000
 196  H13  C13  C12  119.91  3.000
 196  C14  C13  C12  122.12  3.000
 196  C20  C14  C15  118.45  3.000
 196  C20  C14  C13  121.36  3.000
 196  C15  C14  C13  120.19  3.000
 196  C23  C15  C16  123.23  3.000
 196  C23  C15  C14  119.90  3.000
 196  C16  C15  C14  116.87  3.000
 196  C27  C16  C17  118.70  3.000
 196  C27  C16  C15  119.66  3.000
 196  C17  C16  C15  121.64  3.000
 196  H17  C17  C16  118.99  3.000
 196  H17  C17  C12  119.79  3.000
 196  C16  C17  C12  121.21  3.000
 196  H20  C20  C21  119.95  3.000
 196  H20  C20  C14  118.91  3.000
 196  C21  C20  C14  121.14  3.000
 196  H21  C21  C22  119.24  3.000
 196  H21  C21  C20  120.72  3.000
 196  C22  C21  C20  120.04  3.000
 196  O29  C22  C23  123.34  3.000
 196  O29  C22  C21  116.27  3.000
 196  C23  C22  C21  120.39  3.000
 196  H23  C23  C22  119.82  3.000
 196  H23  C23  C15  120.09  3.000
 196  C22  C23  C15  120.09  3.000
 196  N28  C27  C16  180.00  3.000
 196  H29  O29  C22  110.83  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
 196  CONST_01  C4   C3   C2   C1     0.00  0.0  0
 196  CONST_02  C4   C5   C6   C1     0.00  0.0  0
 196  CONST_03  C5   C6   C1   C2     0.00  0.0  0
 196  CONST_04  C5   C4   C3   C2     0.00  0.0  0
 196  CONST_05  C12  C4   C3   C2   180.00  0.0  0
 196  CONST_06  C6   C1   C2   C3     0.00  0.0  0
 196  CONST_07  C6   C5   C4   C3     0.00  0.0  0
 196  CONST_10  C14  C13  C12  C4   180.00  0.0  0
 196  CONST_11  C16  C17  C12  C4   180.00  0.0  0
 196  CONST_14  C12  C4   C5   C6   180.00  0.0  0
 196  CONST_15  C15  C14  C13  C12    0.00  0.0  0
 196  CONST_16  C20  C14  C13  C12  180.00  0.0  0
 196  CONST_17  C15  C16  C17  C12    0.00  0.0  0
 196  CONST_18  C16  C17  C12  C13    0.00  0.0  0
 196  CONST_19  C16  C15  C14  C13    0.00  0.0  0
 196  CONST_20  C23  C15  C14  C13  180.00  0.0  0
 196  CONST_21  C21  C20  C14  C13  180.00  0.0  0
 196  CONST_22  C17  C12  C13  C14    0.00  0.0  0
 196  CONST_23  C17  C16  C15  C14    0.00  0.0  0
 196  CONST_24  C22  C23  C15  C14    0.00  0.0  0
 196  CONST_25  C22  C21  C20  C14    0.00  0.0  0
 196  CONST_26  C21  C20  C14  C15    0.00  0.0  0
 196  CONST_27  C21  C22  C23  C15    0.00  0.0  0
 196  CONST_28  C20  C14  C15  C16  180.00  0.0  0
 196  CONST_29  C22  C23  C15  C16  180.00  0.0  0
 196  CONST_30  C23  C15  C16  C17  180.00  0.0  0
 196  CONST_31  C23  C15  C14  C20    0.00  0.0  0
 196  CONST_32  C23  C22  C21  C20    0.00  0.0  0
 196  CONST_33  O10  C1   C2   C3   180.00  0.0  0
 196  CONST_34  F11  C2   C3   C4   180.00  0.0  0
 196  CONST_35  O10  C1   C6   C5   180.00  0.0  0
 196  CONST_36  F11  C2   C1   C6   180.00  0.0  0
 196  CONST_37  C27  C16  C17  C12  180.00  0.0  0
 196  CONST_38  C27  C16  C15  C14  180.00  0.0  0
 196  CONST_39  O29  C22  C23  C15  180.00  0.0  0
 196  CONST_40  O29  C22  C21  C20  180.00  0.0  0
 196  CONST_41  C27  C16  C15  C23    0.00  0.0  0
 196  CONST_42  H3   C3   C2   C1   180.00  0.0  0
 196  CONST_43  H5   C5   C6   C1   180.00  0.0  0
 196  CONST_44  H6   C6   C1   C2   180.00  0.0  0
 196  CONST_45  H13  C13  C12  C4     0.00  0.0  0
 196  CONST_46  H17  C17  C12  C4     0.00  0.0  0
 196  CONST_47  H20  C20  C14  C13    0.00  0.0  0
 196  CONST_48  H23  C23  C15  C14  180.00  0.0  0
 196  CONST_49  H21  C21  C20  C14  180.00  0.0  0

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
 196  plan-1  C1   0.020
 196  plan-1  C2   0.020
 196  plan-1  C3   0.020
 196  plan-1  C4   0.020
 196  plan-1  C5   0.020
 196  plan-1  C6   0.020
 196  plan-1  O10  0.020
 196  plan-1  F11  0.020
 196  plan-1  C12  0.020
 196  plan-1  H3   0.020
 196  plan-1  H5   0.020
 196  plan-1  H6   0.020
 196  plan-2  C4   0.020
 196  plan-2  C12  0.020
 196  plan-2  C13  0.020
 196  plan-2  C14  0.020
 196  plan-2  C15  0.020
 196  plan-2  C16  0.020
 196  plan-2  C17  0.020
 196  plan-2  C20  0.020
 196  plan-2  C21  0.020
 196  plan-2  C22  0.020
 196  plan-2  C23  0.020
 196  plan-2  C27  0.020
 196  plan-2  N28  0.020
 196  plan-2  O29  0.020
 196  plan-2  H13  0.020
 196  plan-2  H17  0.020
 196  plan-2  H20  0.020
 196  plan-2  H21  0.020
 196  plan-2  H23  0.020

