# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Thu Jul 22 18:58:54 2021
#   Inital geometry file: a 90 line input string
#   Ligand name: 4-(4-ethyl-5-fluoranyl-2-oxidanyl-phenoxy)-3-fluoranyl-benzamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CCc1cc(O)c(Oc2ccc(cc2F)C(N)=O)cc1F
#
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
 RQN  RQN  4-(4-ethyl-5-fluoranyl-2-oxidanyl-phenoxy)-3-fluoranyl-benzamide  ligand  34  21  .  2022-03-23  2022-03-23
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_RQN
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
 RQN  C10   C  CR16  0  -0.321   8.6453  -0.2545  20.8438
 RQN  C13   C  C     0   0.493   5.8998   0.4331  18.3551
 RQN  C17   C  CR6   0   0.495   6.6800   0.3545  22.0550
 RQN  C20   C  CR6   0   0.497  12.1841  -0.5801  23.7301
 RQN  C01   C  CH3   0  -0.656  14.0146  -2.8292  25.2963
 RQN  C03   C  CR6   0  -0.065  12.3388  -1.9530  23.6343
 RQN  C04   C  CR16  0  -0.421  11.1912  -2.7047  23.3965
 RQN  C05   C  CR6   0   0.329   9.9394  -2.1183  23.2595
 RQN  C07   C  CR6   0   0.236   9.8408  -0.7304  23.3555
 RQN  C09   C  CR6   0   0.231   8.0176  -0.0321  22.0607
 RQN  C11   C  CR16  0  -0.275   7.9416  -0.0950  19.6601
 RQN  C12   C  CR6   0  -0.038   6.6012   0.2714  19.6646
 RQN  C16   C  CR16  0  -0.443   5.9721   0.5076  20.8875
 RQN  C19   C  CR16  0  -0.461  10.9613   0.0454  23.5870
 RQN  F18   F  F     0  -0.304   6.0823   0.5892  23.2297
 RQN  N14   N  NH2   0  -0.814   4.5604   0.3598  18.3829
 RQN  O06   O  OH1   0  -0.618   8.8084  -2.8078  23.0306
 RQN  O08   O  O2    0  -0.491   8.6097  -0.1314  23.2722
 RQN  O15   O  O     0  -0.481   6.5314   0.6268  17.3253
 RQN  H101  H  HCR6  0   0.294   9.6872  -0.5444  20.8085
 RQN  H013  H  HCH3  0   0.235  14.9789  -3.3276  25.3980
 RQN  H012  H  HCH3  0   0.228  14.0715  -1.8821  25.8331
 RQN  H011  H  HCH3  0   0.229  13.2640  -3.4493  25.7872
 RQN  H022  H  HCH2  0   0.249  13.6536  -3.5855  23.3154
 RQN  H021  H  HCH2  0   0.248  14.4600  -2.0367  23.3408
 RQN  H041  H  HCR6  0   0.281  11.2814  -3.7832  23.3189
 RQN  H111  H  HCR6  0   0.272   8.4506  -0.2685  18.7222
 RQN  H161  H  HCR6  0   0.285   4.9411   0.8317  20.9530
 RQN  H191  H  HCR6  0   0.294  10.8755   1.1221  23.6612
 RQN  H141  H  HNH2  0   0.406   4.0430   0.4458  17.5232
 RQN  H142  H  HNH2  0   0.415   4.0487   0.0421  19.1876
 RQN  H061  H  HOH1  0   0.482   8.9917  -3.7537  22.9969
 RQN  F21   F  F     0  -0.316  13.2674   0.1838  23.9667
 RQN  C02   C  CH2   0  -0.497  13.6729  -2.6194  23.8221

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
 RQN  O15  C13   double    1.224  0.020  1.224
 RQN  C13  N14   single    1.342  0.020  1.342
 RQN  C13  C12   single    1.494  0.020  1.494
 RQN  C11  C12   aromatic  1.390  0.020  1.390
 RQN  C11  C10   aromatic  1.386  0.020  1.386
 RQN  C12  C16   aromatic  1.395  0.020  1.395
 RQN  C10  C09   aromatic  1.387  0.020  1.387
 RQN  C16  C17   aromatic  1.374  0.020  1.374
 RQN  C09  C17   aromatic  1.392  0.020  1.392
 RQN  C09  O08   single    1.352  0.020  1.352
 RQN  C17  F18   single    1.339  0.020  1.339
 RQN  F21  C20   single    1.347  0.020  1.347
 RQN  C19  C20   aromatic  1.381  0.020  1.381
 RQN  C19  C07   aromatic  1.382  0.020  1.382
 RQN  O08  C07   single    1.372  0.020  1.372
 RQN  C20  C03   aromatic  1.385  0.020  1.385
 RQN  C07  C05   aromatic  1.395  0.020  1.395
 RQN  C03  C02   single    1.503  0.020  1.503
 RQN  C03  C04   aromatic  1.392  0.020  1.392
 RQN  C05  C04   aromatic  1.389  0.020  1.389
 RQN  C05  O06   single    1.344  0.020  1.344
 RQN  C02  C01   single    1.528  0.020  1.528
 RQN  C10  H101  single    0.930  0.020  1.080
 RQN  C01  H013  single    0.970  0.020  1.090
 RQN  C01  H012  single    0.970  0.020  1.090
 RQN  C01  H011  single    0.970  0.020  1.090
 RQN  C02  H022  single    0.970  0.020  1.090
 RQN  C02  H021  single    0.970  0.020  1.090
 RQN  C04  H041  single    0.930  0.020  1.080
 RQN  C11  H111  single    0.930  0.020  1.080
 RQN  C16  H161  single    0.930  0.020  1.080
 RQN  C19  H191  single    0.930  0.020  1.080
 RQN  N14  H141  single    0.860  0.020  1.020
 RQN  N14  H142  single    0.860  0.020  1.020
 RQN  O06  H061  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
 RQN  H101  C10  C11   119.46  3.000
 RQN  H101  C10  C09   120.48  3.000
 RQN  C11   C10  C09   120.07  3.000
 RQN  O15   C13  N14   122.78  3.000
 RQN  N14   C13  C12   116.39  3.000
 RQN  O15   C13  C12   120.83  3.000
 RQN  F18   C17  C16   119.74  3.000
 RQN  F18   C17  C09   118.29  3.000
 RQN  C16   C17  C09   121.97  3.000
 RQN  F21   C20  C19   118.27  3.000
 RQN  C19   C20  C03   122.74  3.000
 RQN  F21   C20  C03   118.99  3.000
 RQN  H011  C01  H012  107.96  3.000
 RQN  H011  C01  H013  107.87  3.000
 RQN  H012  C01  H013  107.77  3.000
 RQN  H011  C01  C02   111.01  3.000
 RQN  H012  C01  C02   111.56  3.000
 RQN  H013  C01  C02   110.53  3.000
 RQN  C04   C03  C02   120.90  3.000
 RQN  C04   C03  C20   117.06  3.000
 RQN  C02   C03  C20   122.01  3.000
 RQN  H041  C04  C05   119.18  3.000
 RQN  H041  C04  C03   118.71  3.000
 RQN  C05   C04  C03   122.12  3.000
 RQN  O06   C05  C07   117.56  3.000
 RQN  O06   C05  C04   123.95  3.000
 RQN  C07   C05  C04   118.49  3.000
 RQN  O08   C07  C19   119.52  3.000
 RQN  O08   C07  C05   119.59  3.000
 RQN  C19   C07  C05   120.84  3.000
 RQN  O08   C09  C17   116.41  3.000
 RQN  O08   C09  C10   125.18  3.000
 RQN  C17   C09  C10   118.39  3.000
 RQN  H111  C11  C12   119.95  3.000
 RQN  H111  C11  C10   118.90  3.000
 RQN  C12   C11  C10   121.14  3.000
 RQN  C16   C12  C11   118.84  3.000
 RQN  C16   C12  C13   122.56  3.000
 RQN  C11   C12  C13   118.58  3.000
 RQN  H161  C16  C12   122.21  3.000
 RQN  H161  C16  C17   118.20  3.000
 RQN  C12   C16  C17   119.58  3.000
 RQN  H191  C19  C07   120.35  3.000
 RQN  H191  C19  C20   120.90  3.000
 RQN  C07   C19  C20   118.75  3.000
 RQN  H142  N14  H141  116.67  3.000
 RQN  H142  N14  C13   122.82  3.000
 RQN  H141  N14  C13   119.37  3.000
 RQN  H061  O06  C05   110.45  3.000
 RQN  C09   O08  C07   118.66  3.000
 RQN  H021  C02  H022  106.30  3.000
 RQN  H021  C02  C03   110.38  3.000
 RQN  H022  C02  C03   108.59  3.000
 RQN  H021  C02  C01   109.73  3.000
 RQN  H022  C02  C01   109.30  3.000
 RQN  C03   C02  C01   112.33  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
 RQN  CONST_01  C16   C12  C11  C10    0.00   0.0  0
 RQN  CONST_02  C16   C17  C09  C10    0.00   0.0  0
 RQN  CONST_03  C11   C12  C16  C17    0.00   0.0  0
 RQN  CONST_04  C11   C10  C09  C17    0.00   0.0  0
 RQN  CONST_05  C05   C07  C19  C20    0.00   0.0  0
 RQN  CONST_06  C05   C04  C03  C20    0.00   0.0  0
 RQN  CONST_07  C07   C19  C20  C03    0.00   0.0  0
 RQN  CONST_08  C07   C05  C04  C03    0.00   0.0  0
 RQN  CONST_09  C19   C20  C03  C04    0.00   0.0  0
 RQN  CONST_10  C19   C07  C05  C04    0.00   0.0  0
 RQN  CONST_11  C12   C11  C10  C09    0.00   0.0  0
 RQN  CONST_12  C12   C16  C17  C09    0.00   0.0  0
 RQN  CONST_13  C13   C12  C11  C10  180.00   0.0  0
 RQN  CONST_14  F18   C17  C09  C10  180.00   0.0  0
 RQN  CONST_15  C17   C16  C12  C13  180.00   0.0  0
 RQN  CONST_16  O08   C07  C19  C20  180.00   0.0  0
 RQN  CONST_17  C19   C20  C03  C02  180.00   0.0  0
 RQN  CONST_18  C05   C04  C03  C02  180.00   0.0  0
 RQN  CONST_19  O06   C05  C04  C03  180.00   0.0  0
 RQN  CONST_20  F21   C20  C03  C04  180.00   0.0  0
 RQN  CONST_21  O08   C07  C05  C04  180.00   0.0  0
 RQN  CONST_22  F21   C20  C19  C07  180.00   0.0  0
 RQN  CONST_23  O08   C09  C10  C11  180.00   0.0  0
 RQN  CONST_24  F18   C17  C16  C12  180.00   0.0  0
 RQN  CONST_25  O08   C09  C17  C16  180.00   0.0  0
 RQN  CONST_26  O06   C05  C07  C19  180.00   0.0  0
 RQN  CONST_27  H101  C10  C09  C17  180.00   0.0  0
 RQN  CONST_28  H041  C04  C03  C20  180.00   0.0  0
 RQN  CONST_29  H191  C19  C20  C03  180.00   0.0  0
 RQN  CONST_30  H111  C11  C10  C09  180.00   0.0  0
 RQN  CONST_31  H161  C16  C17  C09  180.00   0.0  0
 RQN  CONST_32  H141  N14  C13  C12  180.00   0.0  0
 RQN  CONST_33  H142  N14  C13  C12    0.00   0.0  0
 RQN  Var_01    C19   C07  O08  C09  107.33  30.0  2
 RQN  Var_02    C01   C02  C03  C20   82.16  30.0  2
 RQN  Var_03    O15   C13  C12  C11  -20.97  30.0  2
 RQN  Var_04    H013  C01  C02  C03  179.11  30.0  3

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
 RQN  plan-1  C10   0.020
 RQN  plan-1  C13   0.020
 RQN  plan-1  C17   0.020
 RQN  plan-1  C09   0.020
 RQN  plan-1  C11   0.020
 RQN  plan-1  C12   0.020
 RQN  plan-1  C16   0.020
 RQN  plan-1  F18   0.020
 RQN  plan-1  O08   0.020
 RQN  plan-1  H101  0.020
 RQN  plan-1  H111  0.020
 RQN  plan-1  H161  0.020
 RQN  plan-2  C20   0.020
 RQN  plan-2  C03   0.020
 RQN  plan-2  C04   0.020
 RQN  plan-2  C05   0.020
 RQN  plan-2  C07   0.020
 RQN  plan-2  C19   0.020
 RQN  plan-2  O06   0.020
 RQN  plan-2  O08   0.020
 RQN  plan-2  H041  0.020
 RQN  plan-2  H191  0.020
 RQN  plan-2  F21   0.020
 RQN  plan-2  C02   0.020
 RQN  plan-3  C13   0.020
 RQN  plan-3  C12   0.020
 RQN  plan-3  N14   0.020
 RQN  plan-3  O15   0.020
 RQN  plan-3  H141  0.020
 RQN  plan-3  H142  0.020

