# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 25 20:26:00 2022
#   Inital geometry file: a 85 line input string
#   Ligand name: 5-[(6-bromo-1H-indol-1-yl)methyl]-2-methylfuran-3-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1oc(Cn2ccc3ccc(Br)cc23)cc1C(O)=O
#
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
 YXA  YXA  '5-[(6-bromo-1H-indol-1-yl)methyl]-2-methylfuran-3-carboxylic acid'  ligand  31  20  .  2022-03-29  2022-03-29
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_YXA
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
 YXA  C10  C   CH2    0  -0.455  32.1935  50.2246  -29.2131
 YXA  C11  C   CR5    0   0.376  30.9699  50.2782  -30.0526
 YXA  C12  C   CR15   0  -0.400  29.8587  49.5130  -30.0988
 YXA  C13  C   CR5    0  -0.195  29.0207  50.0580  -31.1244
 YXA  C14  C   CR5    0   0.341  29.6955  51.1352  -31.6174
 YXA  C16  C   CH3    0  -0.742  29.4037  52.1356  -32.6744
 YXA  C17  C   C      0   0.349  27.6795  49.5258  -31.5458
 YXA  C2   C   CR15   0  -0.016  31.7912  51.6711  -27.2131
 YXA  C3   C   CR15   0  -0.417  32.1115  52.9220  -26.7767
 YXA  C4   C   CR16   0  -0.342  33.6114  54.7230  -27.9100
 YXA  C5   C   CR16   0  -0.248  34.3817  54.9628  -29.0302
 YXA  C6   C   CR6    0  -0.135  34.4995  53.9753  -30.0193
 YXA  C7   C   CR16   0  -0.279  33.8684  52.7519  -29.9333
 YXA  C8   C   CR56   0   0.381  33.1007  52.5264  -28.7918
 YXA  C9   C   CR56   0   0.067  32.9566  53.4958  -27.7737
 YXA  N1   N   NR5    0  -0.519  32.3909  51.4204  -28.4189
 YXA  O15  O   O      0  -0.436  30.8793  51.2667  -30.9739
 YXA  O18  O   O      0  -0.594  27.1097  50.1122  -32.4892
 YXA  O19  O   OC    -1  -0.595  27.2618  48.5371  -30.9106
 YXA  H1   H   HCH2   0   0.300  32.1128  49.3688  -28.5432
 YXA  H2   H   HCH2   0   0.287  33.0901  50.0637  -29.8160
 YXA  H3   H   HCR5   0   0.248  29.6524  48.6571  -29.4764
 YXA  H4   H   HCH3   0   0.241  30.0349  53.0162  -32.5611
 YXA  H5   H   HCH3   0   0.247  29.5770  51.7289  -33.6726
 YXA  H6   H   HCH3   0   0.253  28.3627  52.4449  -32.6320
 YXA  H7   H   HCR5   0   0.287  31.1757  50.9153  -26.7497
 YXA  H8   H   HCR5   0   0.250  31.7917  53.3754  -25.8523
 YXA  H9   H   HCR6   0   0.256  33.5206  55.4850  -27.1461
 YXA  H10  H   HCR6   0   0.269  34.8916  55.9103  -29.1405
 YXA  H11  H   HCR6   0   0.283  33.9687  52.0076  -30.7123
 YXA  BR   BR  BR     0  -0.064  35.5693  54.3398  -31.5391

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
 YXA  C16  C14  single    1.484  0.020  1.484
 YXA  C14  O15  aromatic  1.354  0.020  1.354
 YXA  C14  C13  aromatic  1.363  0.020  1.363
 YXA  O15  C11  aromatic  1.354  0.020  1.354
 YXA  O18  C17  deloc     1.248  0.020  1.248
 YXA  C17  C13  single    1.503  0.020  1.503
 YXA  C17  O19  deloc     1.247  0.020  1.247
 YXA  C13  C12  aromatic  1.432  0.020  1.432
 YXA  BR   C6   single    1.894  0.020  1.894
 YXA  C11  C12  aromatic  1.350  0.020  1.350
 YXA  C11  C10  single    1.485  0.020  1.485
 YXA  C7   C6   aromatic  1.379  0.020  1.379
 YXA  C7   C8   aromatic  1.394  0.020  1.394
 YXA  C10  N1   single    1.449  0.020  1.449
 YXA  C6   C5   aromatic  1.403  0.020  1.403
 YXA  C8   N1   aromatic  1.366  0.020  1.366
 YXA  C8   C9   aromatic  1.413  0.020  1.413
 YXA  N1   C2   aromatic  1.370  0.020  1.370
 YXA  C5   C4   aromatic  1.380  0.020  1.380
 YXA  C9   C4   aromatic  1.398  0.020  1.398
 YXA  C9   C3   aromatic  1.427  0.020  1.427
 YXA  C2   C3   aromatic  1.363  0.020  1.363
 YXA  C10  H1   single    0.970  0.020  1.090
 YXA  C10  H2   single    0.970  0.020  1.090
 YXA  C12  H3   single    0.930  0.020  1.080
 YXA  C16  H4   single    0.970  0.020  1.090
 YXA  C16  H5   single    0.970  0.020  1.090
 YXA  C16  H6   single    0.970  0.020  1.090
 YXA  C2   H7   single    0.930  0.020  1.080
 YXA  C3   H8   single    0.930  0.020  1.080
 YXA  C4   H9   single    0.930  0.020  1.080
 YXA  C5   H10  single    0.930  0.020  1.080
 YXA  C7   H11  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
 YXA  H2   C10  H1   106.52  3.000
 YXA  H2   C10  N1   108.19  3.000
 YXA  H1   C10  N1   108.74  3.000
 YXA  H2   C10  C11  111.69  3.000
 YXA  H1   C10  C11  108.35  3.000
 YXA  N1   C10  C11  113.10  3.000
 YXA  O15  C11  C12  109.59  3.000
 YXA  C12  C11  C10  132.63  3.000
 YXA  O15  C11  C10  117.78  3.000
 YXA  H3   C12  C13  127.12  3.000
 YXA  H3   C12  C11  125.99  3.000
 YXA  C13  C12  C11  106.89  3.000
 YXA  C17  C13  C14  128.31  3.000
 YXA  C17  C13  C12  126.02  3.000
 YXA  C14  C13  C12  105.66  3.000
 YXA  O15  C14  C16  116.42  3.000
 YXA  O15  C14  C13  109.73  3.000
 YXA  C16  C14  C13  133.84  3.000
 YXA  H6   C16  H5   107.08  3.000
 YXA  H6   C16  H4   108.72  3.000
 YXA  H5   C16  H4   107.71  3.000
 YXA  H6   C16  C14  110.63  3.000
 YXA  H5   C16  C14  111.64  3.000
 YXA  H4   C16  C14  110.90  3.000
 YXA  O19  C17  O18  127.19  3.000
 YXA  O19  C17  C13  115.89  3.000
 YXA  O18  C17  C13  116.92  3.000
 YXA  H7   C2   N1   119.96  3.000
 YXA  H7   C2   C3   129.74  3.000
 YXA  N1   C2   C3   110.30  3.000
 YXA  H8   C3   C9   127.26  3.000
 YXA  H8   C3   C2   126.22  3.000
 YXA  C9   C3   C2   106.52  3.000
 YXA  H9   C4   C9   120.65  3.000
 YXA  H9   C4   C5   119.81  3.000
 YXA  C9   C4   C5   119.54  3.000
 YXA  H10  C5   C6   120.35  3.000
 YXA  H10  C5   C4   119.86  3.000
 YXA  C6   C5   C4   119.79  3.000
 YXA  BR   C6   C7   118.63  3.000
 YXA  C7   C6   C5   122.82  3.000
 YXA  BR   C6   C5   118.54  3.000
 YXA  H11  C7   C8   121.96  3.000
 YXA  H11  C7   C6   121.52  3.000
 YXA  C8   C7   C6   116.52  3.000
 YXA  N1   C8   C9   107.80  3.000
 YXA  C9   C8   C7   122.35  3.000
 YXA  N1   C8   C7   129.84  3.000
 YXA  C8   C9   C4   118.96  3.000
 YXA  C4   C9   C3   134.31  3.000
 YXA  C8   C9   C3   106.73  3.000
 YXA  C8   N1   C2   108.64  3.000
 YXA  C2   N1   C10  125.02  3.000
 YXA  C8   N1   C10  126.11  3.000
 YXA  C14  O15  C11  108.12  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
 YXA  CONST_01  C13  C14  O15  C11     0.00   0.0  0
 YXA  CONST_02  C14  C13  C12  C11     0.00   0.0  0
 YXA  CONST_03  O15  C14  C13  C12     0.00   0.0  0
 YXA  CONST_04  C14  O15  C11  C12     0.00   0.0  0
 YXA  CONST_05  O15  C11  C12  C13     0.00   0.0  0
 YXA  CONST_06  C7   C8   N1   C2    180.00   0.0  0
 YXA  CONST_07  C9   C8   N1   C2      0.00   0.0  0
 YXA  CONST_08  C8   C9   C3   C2      0.00   0.0  0
 YXA  CONST_09  C4   C9   C3   C2    180.00   0.0  0
 YXA  CONST_10  C7   C8   C9   C3    180.00   0.0  0
 YXA  CONST_11  N1   C8   C9   C3      0.00   0.0  0
 YXA  CONST_12  C5   C4   C9   C3    180.00   0.0  0
 YXA  CONST_13  C8   N1   C2   C3      0.00   0.0  0
 YXA  CONST_14  C7   C6   C5   C4      0.00   0.0  0
 YXA  CONST_15  C7   C8   C9   C4      0.00   0.0  0
 YXA  CONST_16  N1   C8   C9   C4    180.00   0.0  0
 YXA  CONST_17  C8   C7   C6   C5      0.00   0.0  0
 YXA  CONST_18  C8   C9   C4   C5      0.00   0.0  0
 YXA  CONST_19  N1   C8   C7   C6    180.00   0.0  0
 YXA  CONST_20  C9   C8   C7   C6      0.00   0.0  0
 YXA  CONST_21  C9   C4   C5   C6      0.00   0.0  0
 YXA  CONST_22  N1   C2   C3   C9      0.00   0.0  0
 YXA  CONST_23  C14  O15  C11  C10   180.00   0.0  0
 YXA  CONST_24  C13  C12  C11  C10   180.00   0.0  0
 YXA  CONST_25  C7   C8   N1   C10     0.00   0.0  0
 YXA  CONST_26  C9   C8   N1   C10   180.00   0.0  0
 YXA  CONST_27  C3   C2   N1   C10   180.00   0.0  0
 YXA  CONST_28  C16  C14  O15  C11   180.00   0.0  0
 YXA  CONST_29  C17  C13  C12  C11   180.00   0.0  0
 YXA  CONST_30  C16  C14  C13  C12   180.00   0.0  0
 YXA  CONST_31  O15  C14  C13  C17   180.00   0.0  0
 YXA  CONST_32  BR   C6   C5   C4    180.00   0.0  0
 YXA  CONST_33  BR   C6   C7   C8    180.00   0.0  0
 YXA  CONST_34  H3   C12  C13  C14   180.00   0.0  0
 YXA  CONST_35  H9   C4   C9   C3      0.00   0.0  0
 YXA  CONST_36  H8   C3   C9   C4      0.00   0.0  0
 YXA  CONST_37  H11  C7   C6   C5    180.00   0.0  0
 YXA  CONST_38  H10  C5   C6   C7    180.00   0.0  0
 YXA  CONST_39  H7   C2   N1   C8    180.00   0.0  0
 YXA  Var_01    C8   N1   C10  C11   -91.03  30.0  2
 YXA  Var_02    N1   C10  C11  C12  -119.47  30.0  2
 YXA  Var_03    O18  C17  C13  C12  -177.97  30.0  3
 YXA  Var_04    H4   C16  C14  C13   161.98  30.0  2

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
 YXA  plan-1  C10  0.020
 YXA  plan-1  C11  0.020
 YXA  plan-1  C12  0.020
 YXA  plan-1  C13  0.020
 YXA  plan-1  C14  0.020
 YXA  plan-1  C16  0.020
 YXA  plan-1  C17  0.020
 YXA  plan-1  O15  0.020
 YXA  plan-1  H3   0.020
 YXA  plan-2  C10  0.020
 YXA  plan-2  C2   0.020
 YXA  plan-2  C3   0.020
 YXA  plan-2  C4   0.020
 YXA  plan-2  C5   0.020
 YXA  plan-2  C6   0.020
 YXA  plan-2  C7   0.020
 YXA  plan-2  C8   0.020
 YXA  plan-2  C9   0.020
 YXA  plan-2  N1   0.020
 YXA  plan-2  H7   0.020
 YXA  plan-2  H8   0.020
 YXA  plan-2  H9   0.020
 YXA  plan-2  H10  0.020
 YXA  plan-2  H11  0.020
 YXA  plan-2  BR   0.020
 YXA  plan-3  C13  0.020
 YXA  plan-3  C17  0.020
 YXA  plan-3  O18  0.020
 YXA  plan-3  O19  0.020

