# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue Apr  7 18:18:53 2020
#   Inital geometry file: a 102 line input string
#   Ligand name: 6-(4-fluorophenyl)-5-[4-(1H-tetrazol-5-yl)phenyl]pyridine-2,3-diol
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Oc1cc(c2ccc(cc2)c3[nH]nnn3)c(nc1O)c4ccc(F)cc4
#
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
 21A  21A  6-(4-fluorophenyl)-5-[4-(1H-tetrazol-5-yl)phenyl]pyridine-2,3-diol  ligand  38  26  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_21A
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
 21A  O01  O  OH1   0  -0.625  -5.5463  -1.1747  -0.1333
 21A  C02  C  CR6   0   0.360  -4.2104  -1.1335  -0.0696
 21A  C03  C  CR6   0   0.234  -3.5324  -2.3655  -0.0751
 21A  O04  O  OH1   0  -0.621  -4.1660  -3.5494  -0.1251
 21A  C05  C  CR16  0  -0.266  -2.1579  -2.3139  -0.0460
 21A  C06  C  CR6   0   0.027  -1.4883  -1.0855   0.0010
 21A  C07  C  CR6   0  -0.002  -0.0126  -1.0776  -0.0549
 21A  C08  C  CR16  0  -0.275   0.7316  -1.8576   0.8276
 21A  C09  C  CR16  0  -0.267   2.1150  -1.8699   0.7715
 21A  C10  C  CR6   0   0.042   2.7851  -1.1040  -0.1790
 21A  C11  C  CR5   0   0.502   4.2380  -1.0915  -0.2621
 21A  N12  N  NR15  0  -0.507   5.0923  -1.7044   0.5632
 21A  N13  N  N     0  -0.072   6.3293  -1.4617   0.1672
 21A  N14  N  N     0  -0.139   6.2365  -0.7239  -0.8674
 21A  N15  N  N     0  -0.344   4.9655  -0.4718  -1.1662
 21A  C16  C  CR16  0  -0.255   2.0448  -0.3344  -1.0773
 21A  C17  C  CR16  0  -0.264   0.6654  -0.3228  -1.0131
 21A  C18  C  CR6   0   0.202  -2.2605   0.0730   0.0536
 21A  N19  N  N     0  -0.461  -3.5957   0.0157   0.0006
 21A  C20  C  CR6   0   0.019  -1.6886   1.4302   0.1878
 21A  C21  C  CR16  0  -0.269  -2.1974   2.4781  -0.5780
 21A  C22  C  CR16  0  -0.400  -1.6881   3.7624  -0.4631
 21A  C23  C  CR6   0   0.517  -0.6706   3.9910   0.4431
 21A  F24  F  F     0  -0.314  -0.1715   5.2316   0.5603
 21A  C25  C  CR16  0  -0.395  -0.1546   2.9835   1.2350
 21A  C26  C  CR16  0  -0.265  -0.6703   1.7044   1.0998
 21A  H2   H  HOH1  0   0.479  -5.1223  -3.4288  -0.1566
 21A  H3   H  HCR6  0   0.281  -1.5911  -3.2365  -0.0899
 21A  H4   H  HCR6  0   0.267   0.2276  -2.4501   1.5806
 21A  H5   H  HCR6  0   0.257   2.6558  -2.4814   1.4828
 21A  H6   H  HNR5  0   0.451   4.9236  -2.2708   1.3824
 21A  H7   H  HCR6  0   0.267   2.5507   0.2536  -1.8313
 21A  H8   H  HCR6  0   0.263   0.1074   0.2727  -1.7239
 21A  H9   H  HCR6  0   0.262  -2.9960   2.2906  -1.2837
 21A  H10  H  HCR6  0   0.281  -2.0758   4.5695  -1.0709
 21A  H11  H  HCR6  0   0.281   0.6316   3.1898   1.9491
 21A  H12  H  HCR6  0   0.266  -0.2760   0.9176   1.7288
 21A  H13  H  HOH1  0   0.482  -5.8966  -0.2739  -0.1235

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
 21A  F24  C23  single    1.342  0.020  1.342
 21A  N13  N12  aromatic  1.321  0.020  1.321
 21A  N13  N14  aromatic  1.274  0.020  1.274
 21A  N12  C11  aromatic  1.337  0.020  1.337
 21A  N14  N15  aromatic  1.330  0.020  1.330
 21A  C23  C22  aromatic  1.382  0.020  1.382
 21A  C23  C25  aromatic  1.381  0.020  1.381
 21A  C22  C21  aromatic  1.386  0.020  1.386
 21A  C11  N15  aromatic  1.316  0.020  1.316
 21A  C11  C10  single    1.455  0.020  1.455
 21A  C25  C26  aromatic  1.386  0.020  1.386
 21A  C21  C20  aromatic  1.394  0.020  1.394
 21A  C10  C16  aromatic  1.395  0.020  1.395
 21A  C10  C09  aromatic  1.393  0.020  1.393
 21A  C16  C17  aromatic  1.381  0.020  1.381
 21A  C09  C08  aromatic  1.385  0.020  1.385
 21A  C26  C20  aromatic  1.394  0.020  1.394
 21A  C20  C18  single    1.479  0.020  1.479
 21A  C17  C07  aromatic  1.396  0.020  1.396
 21A  C08  C07  aromatic  1.393  0.020  1.393
 21A  C07  C06  single    1.477  0.020  1.477
 21A  C18  C06  aromatic  1.393  0.020  1.393
 21A  C18  N19  aromatic  1.338  0.020  1.338
 21A  C06  C05  aromatic  1.400  0.020  1.400
 21A  N19  C02  aromatic  1.305  0.020  1.305
 21A  C05  C03  aromatic  1.376  0.020  1.376
 21A  C02  C03  aromatic  1.406  0.020  1.406
 21A  C02  O01  single    1.338  0.020  1.338
 21A  C03  O04  single    1.344  0.020  1.344
 21A  O04  H2   single    0.850  0.020  0.980
 21A  C05  H3   single    0.930  0.020  1.080
 21A  C08  H4   single    0.930  0.020  1.080
 21A  C09  H5   single    0.930  0.020  1.080
 21A  N12  H6   single    0.860  0.020  1.020
 21A  C16  H7   single    0.930  0.020  1.080
 21A  C17  H8   single    0.930  0.020  1.080
 21A  C21  H9   single    0.930  0.020  1.080
 21A  C22  H10  single    0.930  0.020  1.080
 21A  C25  H11  single    0.930  0.020  1.080
 21A  C26  H12  single    0.930  0.020  1.080
 21A  O01  H13  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
 21A  H13  O01  C02  109.44  3.000
 21A  N19  C02  C03  122.99  3.000
 21A  C03  C02  O01  117.02  3.000
 21A  N19  C02  O01  119.99  3.000
 21A  C05  C03  O04  120.32  3.000
 21A  O04  C03  C02  123.00  3.000
 21A  C05  C03  C02  116.67  3.000
 21A  H2   O04  C03  111.02  3.000
 21A  H3   C05  C06  119.89  3.000
 21A  H3   C05  C03  119.33  3.000
 21A  C06  C05  C03  120.76  3.000
 21A  C18  C06  C07  123.42  3.000
 21A  C18  C06  C05  117.77  3.000
 21A  C07  C06  C05  118.78  3.000
 21A  C17  C07  C08  118.57  3.000
 21A  C08  C07  C06  120.45  3.000
 21A  C17  C07  C06  120.96  3.000
 21A  H4   C08  C09  119.24  3.000
 21A  H4   C08  C07  119.89  3.000
 21A  C09  C08  C07  120.87  3.000
 21A  H5   C09  C10  121.24  3.000
 21A  H5   C09  C08  118.52  3.000
 21A  C10  C09  C08  120.23  3.000
 21A  C16  C10  C11  119.22  3.000
 21A  C16  C10  C09  119.17  3.000
 21A  C11  C10  C09  121.61  3.000
 21A  N15  C11  N12  106.67  3.000
 21A  N15  C11  C10  126.54  3.000
 21A  N12  C11  C10  126.79  3.000
 21A  H6   N12  N13  120.16  3.000
 21A  H6   N12  C11  130.63  3.000
 21A  N13  N12  C11  109.21  3.000
 21A  N14  N13  N12  106.35  3.000
 21A  N15  N14  N13  111.22  3.000
 21A  N14  N15  C11  106.55  3.000
 21A  H7   C16  C17  119.66  3.000
 21A  H7   C16  C10  120.03  3.000
 21A  C17  C16  C10  120.31  3.000
 21A  H8   C17  C16  119.29  3.000
 21A  H8   C17  C07  119.87  3.000
 21A  C16  C17  C07  120.84  3.000
 21A  C20  C18  N19  115.41  3.000
 21A  N19  C18  C06  121.07  3.000
 21A  C20  C18  C06  123.52  3.000
 21A  C18  N19  C02  120.66  3.000
 21A  C26  C20  C21  118.56  3.000
 21A  C26  C20  C18  121.48  3.000
 21A  C21  C20  C18  119.93  3.000
 21A  H9   C21  C22  119.06  3.000
 21A  H9   C21  C20  119.82  3.000
 21A  C22  C21  C20  121.12  3.000
 21A  H10  C22  C23  120.59  3.000
 21A  H10  C22  C21  120.85  3.000
 21A  C23  C22  C21  118.57  3.000
 21A  C25  C23  F24  119.02  3.000
 21A  C25  C23  C22  122.03  3.000
 21A  F24  C23  C22  118.95  3.000
 21A  H11  C25  C26  120.72  3.000
 21A  H11  C25  C23  120.71  3.000
 21A  C26  C25  C23  118.57  3.000
 21A  H12  C26  C25  118.62  3.000
 21A  H12  C26  C20  120.24  3.000
 21A  C25  C26  C20  121.14  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
 21A  CONST_01  C20  C18  N19  C02  180.00  0.0  0
 21A  CONST_02  C06  C18  N19  C02    0.00  0.0  0
 21A  CONST_03  C06  C05  C03  C02    0.00  0.0  0
 21A  CONST_04  C07  C06  C05  C03  180.00  0.0  0
 21A  CONST_05  C18  C06  C05  C03    0.00  0.0  0
 21A  CONST_06  C18  N19  C02  C03    0.00  0.0  0
 21A  CONST_09  C20  C18  C06  C05  180.00  0.0  0
 21A  CONST_10  N19  C18  C06  C05    0.00  0.0  0
 21A  CONST_11  N19  C02  C03  C05    0.00  0.0  0
 21A  CONST_12  C16  C17  C07  C06  180.00  0.0  0
 21A  CONST_13  C09  C08  C07  C06  180.00  0.0  0
 21A  CONST_16  C10  C16  C17  C07    0.00  0.0  0
 21A  CONST_17  C10  C09  C08  C07    0.00  0.0  0
 21A  CONST_18  C20  C18  C06  C07    0.00  0.0  0
 21A  CONST_19  N19  C18  C06  C07  180.00  0.0  0
 21A  CONST_20  C11  C10  C09  C08  180.00  0.0  0
 21A  CONST_21  C16  C10  C09  C08    0.00  0.0  0
 21A  CONST_22  C16  C17  C07  C08    0.00  0.0  0
 21A  CONST_24  N12  C11  C10  C09    0.00  0.0  0
 21A  CONST_25  N15  C11  C10  C09  180.00  0.0  0
 21A  CONST_26  C17  C16  C10  C09    0.00  0.0  0
 21A  CONST_27  C17  C07  C08  C09    0.00  0.0  0
 21A  CONST_28  N13  N12  C11  C10  180.00  0.0  0
 21A  CONST_29  N14  N15  C11  C10  180.00  0.0  0
 21A  CONST_30  N14  N13  N12  C11    0.00  0.0  0
 21A  CONST_31  N13  N14  N15  C11    0.00  0.0  0
 21A  CONST_32  C17  C16  C10  C11  180.00  0.0  0
 21A  CONST_33  N15  N14  N13  N12    0.00  0.0  0
 21A  CONST_34  N14  N15  C11  N12    0.00  0.0  0
 21A  CONST_35  C16  C10  C11  N12  180.00  0.0  0
 21A  CONST_36  N15  C11  N12  N13    0.00  0.0  0
 21A  CONST_37  C16  C10  C11  N15    0.00  0.0  0
 21A  CONST_39  C22  C21  C20  C18  180.00  0.0  0
 21A  CONST_40  C25  C26  C20  C18  180.00  0.0  0
 21A  CONST_43  C23  C22  C21  C20    0.00  0.0  0
 21A  CONST_44  C23  C25  C26  C20    0.00  0.0  0
 21A  CONST_45  C25  C23  C22  C21    0.00  0.0  0
 21A  CONST_46  C25  C26  C20  C21    0.00  0.0  0
 21A  CONST_47  C26  C25  C23  C22    0.00  0.0  0
 21A  CONST_48  C26  C20  C21  C22    0.00  0.0  0
 21A  CONST_49  C18  N19  C02  O01  180.00  0.0  0
 21A  CONST_50  C05  C03  C02  O01  180.00  0.0  0
 21A  CONST_51  C06  C05  C03  O04  180.00  0.0  0
 21A  CONST_52  N19  C02  C03  O04  180.00  0.0  0
 21A  CONST_53  F24  C23  C22  C21  180.00  0.0  0
 21A  CONST_54  C26  C25  C23  F24  180.00  0.0  0
 21A  CONST_55  H3   C05  C03  C02  180.00  0.0  0
 21A  CONST_56  H8   C17  C07  C06    0.00  0.0  0
 21A  CONST_57  H4   C08  C07  C06    0.00  0.0  0
 21A  CONST_58  H7   C16  C17  C07  180.00  0.0  0
 21A  CONST_59  H5   C09  C08  C07  180.00  0.0  0
 21A  CONST_60  H6   N12  C11  C10    0.00  0.0  0
 21A  CONST_61  H9   C21  C20  C18    0.00  0.0  0
 21A  CONST_62  H12  C26  C20  C18    0.00  0.0  0
 21A  CONST_63  H10  C22  C21  C20  180.00  0.0  0
 21A  CONST_64  H11  C25  C26  C20  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
 21A  plan-1  C10  0.020
 21A  plan-1  C11  0.020
 21A  plan-1  N12  0.020
 21A  plan-1  N13  0.020
 21A  plan-1  N14  0.020
 21A  plan-1  N15  0.020
 21A  plan-1  H6   0.020
 21A  plan-2  C06  0.020
 21A  plan-2  C07  0.020
 21A  plan-2  C08  0.020
 21A  plan-2  C09  0.020
 21A  plan-2  C10  0.020
 21A  plan-2  C11  0.020
 21A  plan-2  C16  0.020
 21A  plan-2  C17  0.020
 21A  plan-2  H4   0.020
 21A  plan-2  H5   0.020
 21A  plan-2  H7   0.020
 21A  plan-2  H8   0.020
 21A  plan-3  O01  0.020
 21A  plan-3  C02  0.020
 21A  plan-3  C03  0.020
 21A  plan-3  O04  0.020
 21A  plan-3  C05  0.020
 21A  plan-3  C06  0.020
 21A  plan-3  C07  0.020
 21A  plan-3  C18  0.020
 21A  plan-3  N19  0.020
 21A  plan-3  C20  0.020
 21A  plan-3  H3   0.020
 21A  plan-4  C18  0.020
 21A  plan-4  C20  0.020
 21A  plan-4  C21  0.020
 21A  plan-4  C22  0.020
 21A  plan-4  C23  0.020
 21A  plan-4  F24  0.020
 21A  plan-4  C25  0.020
 21A  plan-4  C26  0.020
 21A  plan-4  H9   0.020
 21A  plan-4  H10  0.020
 21A  plan-4  H11  0.020
 21A  plan-4  H12  0.020

