# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Tue May  5 11:14:33 2020
#   Inital geometry file: a 148 line input string
#   Ligand name: 2-{(R)-[3-(acryloylamino)phenyl][2-(piperidin-1-yl)ethoxy]methyl}thieno[3,2-b]pyridine-7-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1ccnc2cc(sc12)[C@H](OCCN3CCCCC3)c4cccc(NC(=O)C=C)c4
#
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
 H74  H74  '2-{(R)-[3-(acryloylamino)phenyl][2-(piperidin-1-yl)ethoxy]methyl}thieno[3,2-b]pyridine-7-carboxylic acid'  ligand  59  33  .  2021-08-11  2022-09-22
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK
;

data_comp_H74
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
 H74  C17  C  C1     0  -0.340   7.3885  -1.4226   0.1857
 H74  C10  C  CR6    0   0.107   1.9816   1.2375   0.2528
 H74  C11  C  CR16   0  -0.331   1.8595   1.8495  -0.9902
 H74  C12  C  CR16   0  -0.226   2.9047   1.7502  -1.8957
 H74  C13  C  CR16   0  -0.328   4.0679   1.0537  -1.5985
 H74  C14  C  CR6    0   0.402   4.1904   0.4367  -0.3524
 H74  C16  C  C      0   0.540   6.4402  -0.6039  -0.6128
 H74  C04  C  CR6    0   0.001  -2.4128  -2.5974  -0.2816
 H74  C05  C  CR56   0  -0.240  -1.5060  -1.7251   0.3117
 H74  C06  C  CR56   0   0.270  -0.8738  -2.0771   1.5214
 H74  C07  C  CR15   0  -0.250   0.0133  -1.0478   1.9800
 H74  C08  C  CR5    0  -0.169   0.0336   0.0123   1.1416
 H74  C09  C  CH1    0  -0.044   0.8597   1.2629   1.2669
 H74  C20  C  CR16   0  -0.399   3.1394   0.5418   0.5608
 H74  C25  C  CH2    0  -0.276  -3.6937   2.1501   0.9910
 H74  C26  C  CH2    0  -0.450  -4.4794   1.5049  -0.1399
 H74  C27  C  CH2    0  -0.438  -5.1633   2.5637  -0.9949
 H74  C28  C  CH2    0  -0.433  -4.1370   3.5917  -1.4537
 H74  C29  C  CH2    0  -0.272  -3.3759   4.1627  -0.2671
 H74  C32  C  CR16   0  -0.093  -1.9603  -4.0617   1.5787
 H74  C33  C  CR16   0  -0.391  -2.6326  -3.7911   0.3852
 H74  N15  N  NH1    0  -0.763   5.3074  -0.2893   0.0673
 H74  N24  N  NT     0  -0.392  -2.7272   3.1118   0.4937
 H74  N31  N  N      0  -0.438  -1.0987  -3.2352   2.1462
 H74  O01  O  OC    -1  -0.576  -3.9394  -3.0556  -2.0217
 H74  O03  O  O      0  -0.571  -2.7177  -1.1853  -2.1171
 H74  O19  O  O      0  -0.468   6.6695  -0.2597  -1.7602
 H74  O21  O  O2     0  -0.478   0.0838   2.4045   1.0466
 H74  S30  S  S2     0   0.266  -1.0207  -0.1597  -0.2339
 H74  H1   H  H      0   0.275   7.1126  -1.6876   1.2002
 H74  H4   H  HCR6   0   0.256   0.9657   2.3977  -1.2540
 H74  H5   H  HCR6   0   0.258   2.8188   2.2277  -2.8635
 H74  H6   H  HCR6   0   0.281   4.8579   1.0000  -2.3278
 H74  H7   H  HCR5   0   0.262   0.5951  -1.1153   2.8892
 H74  H8   H  HCH1   0   0.251   1.3028   1.2647   2.2749
 H74  H9   H  HCR6   0   0.264   3.2297   0.0661   1.5322
 H74  H10  H  HCH2   0   0.218  -0.3584   3.1099   2.9375
 H74  H11  H  HCH2   0   0.215  -1.3390   1.7490   2.4076
 H74  H12  H  HCH2   0   0.192  -2.4811   3.9994   2.4124
 H74  H13  H  HCH2   0   0.231  -1.3706   4.5301   1.1609
 H74  H16  H  HCH2   0   0.243  -3.7982   0.9104  -0.7537
 H74  H17  H  HCH2   0   0.215  -5.2113   0.8146   0.2869
 H74  H18  H  HCH2   0   0.225  -5.6612   2.1070  -1.8536
 H74  H19  H  HCH2   0   0.204  -5.9433   3.0630  -0.4092
 H74  H20  H  HCH2   0   0.213  -3.4249   3.1161  -2.1348
 H74  H21  H  HCH2   0   0.223  -4.6159   4.4051  -2.0037
 H74  H22  H  HCH2   0   0.226  -2.6111   4.8596  -0.6200
 H74  H23  H  HCH2   0   0.173  -4.0737   4.7503   0.3595
 H74  H24  H  HCR6   0   0.255  -2.1365  -5.0019   2.0903
 H74  H25  H  HCR6   0   0.259  -3.3218  -4.5189  -0.0202
 H74  H26  H  HNH1   0   0.420   5.2442  -0.6458   1.0092
 H74  C1   C  C2     0  -0.467   8.5474  -1.8297  -0.3194
 H74  H2   H  H      0   0.262   8.8496  -1.5838  -1.3291
 H74  H3   H  H      0   0.265   9.2316  -2.4277   0.2661
 H74  C22  C  CH2    0  -0.164  -0.8587   2.6719   2.0640
 H74  C23  C  CH2    0  -0.298  -1.8923   3.6493   1.5462
 H74  H14  H  HCH2   0   0.175  -4.3970   2.6302   1.6991
 H74  C02  C  C      0   0.424  -3.0936  -2.2536  -1.5961
 H74  H15  H  HCH2   0   0.227  -3.1712   1.3710   1.5484

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
 H74  C27  C28  single    1.523  0.020  1.523
 H74  C27  C26  single    1.523  0.020  1.523
 H74  C28  C29  single    1.521  0.020  1.521
 H74  C26  C25  single    1.521  0.020  1.521
 H74  C29  N24  single    1.451  0.020  1.451
 H74  C25  N24  single    1.451  0.020  1.451
 H74  N24  C23  single    1.447  0.020  1.447
 H74  C23  C22  single    1.514  0.020  1.514
 H74  C22  O21  single    1.413  0.020  1.413
 H74  C07  C08  aromatic  1.352  0.020  1.352
 H74  C07  C06  aromatic  1.434  0.020  1.434
 H74  O21  C09  single    1.398  0.020  1.398
 H74  C09  C08  single    1.504  0.020  1.504
 H74  C09  C10  single    1.513  0.020  1.513
 H74  N31  C06  aromatic  1.335  0.020  1.335
 H74  N31  C32  aromatic  1.322  0.020  1.322
 H74  C08  S30  aromatic  1.742  0.020  1.742
 H74  C06  C05  aromatic  1.410  0.020  1.410
 H74  C20  C10  aromatic  1.385  0.020  1.385
 H74  C20  C14  aromatic  1.396  0.020  1.396
 H74  C32  C33  aromatic  1.396  0.020  1.396
 H74  C17  C16  single    1.486  0.020  1.486
 H74  C10  C11  aromatic  1.391  0.020  1.391
 H74  N15  C16  single    1.358  0.020  1.358
 H74  N15  C14  single    1.397  0.020  1.397
 H74  C16  O19  double    1.220  0.020  1.220
 H74  C14  C13  aromatic  1.396  0.020  1.396
 H74  C05  S30  aromatic  1.727  0.020  1.727
 H74  C05  C04  aromatic  1.391  0.020  1.391
 H74  C11  C12  aromatic  1.386  0.020  1.386
 H74  C33  C04  aromatic  1.385  0.020  1.385
 H74  C13  C12  aromatic  1.388  0.020  1.388
 H74  C04  C02  single    1.520  0.020  1.520
 H74  C02  O03  deloc     1.247  0.020  1.247
 H74  C02  O01  deloc     1.241  0.020  1.241
 H74  C17  H1   single    0.930  0.020  1.080
 H74  C11  H4   single    0.930  0.020  1.080
 H74  C12  H5   single    0.930  0.020  1.080
 H74  C13  H6   single    0.930  0.020  1.080
 H74  C07  H7   single    0.930  0.020  1.080
 H74  C09  H8   single    0.970  0.020  1.090
 H74  C20  H9   single    0.930  0.020  1.080
 H74  C22  H10  single    0.970  0.020  1.090
 H74  C22  H11  single    0.970  0.020  1.090
 H74  C23  H12  single    0.970  0.020  1.090
 H74  C23  H13  single    0.970  0.020  1.090
 H74  C25  H14  single    0.970  0.020  1.090
 H74  C25  H15  single    0.970  0.020  1.090
 H74  C26  H16  single    0.970  0.020  1.090
 H74  C26  H17  single    0.970  0.020  1.090
 H74  C27  H18  single    0.970  0.020  1.090
 H74  C27  H19  single    0.970  0.020  1.090
 H74  C28  H20  single    0.970  0.020  1.090
 H74  C28  H21  single    0.970  0.020  1.090
 H74  C29  H22  single    0.970  0.020  1.090
 H74  C29  H23  single    0.970  0.020  1.090
 H74  C32  H24  single    0.930  0.020  1.080
 H74  C33  H25  single    0.930  0.020  1.080
 H74  N15  H26  single    0.860  0.020  1.020
 H74  C17  C1   double    1.328  0.020  1.328
 H74  C1   H2   single    0.930  0.020  1.080
 H74  C1   H3   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
 H74  C1   C17  H1   120.19  3.000
 H74  C1   C17  C16  121.43  3.000
 H74  H1   C17  C16  118.37  3.000
 H74  C20  C10  C09  118.64  3.000
 H74  C20  C10  C11  119.54  3.000
 H74  C09  C10  C11  121.78  3.000
 H74  H4   C11  C12  120.01  3.000
 H74  H4   C11  C10  120.91  3.000
 H74  C12  C11  C10  119.08  3.000
 H74  H5   C12  C13  118.64  3.000
 H74  H5   C12  C11  119.50  3.000
 H74  C13  C12  C11  121.86  3.000
 H74  H6   C13  C14  121.22  3.000
 H74  H6   C13  C12  119.67  3.000
 H74  C14  C13  C12  119.11  3.000
 H74  N15  C14  C20  116.40  3.000
 H74  N15  C14  C13  124.62  3.000
 H74  C20  C14  C13  118.98  3.000
 H74  O19  C16  N15  124.23  3.000
 H74  O19  C16  C17  122.76  3.000
 H74  N15  C16  C17  113.01  3.000
 H74  C33  C04  C05  116.01  3.000
 H74  C33  C04  C02  122.71  3.000
 H74  C05  C04  C02  121.27  3.000
 H74  S30  C05  C06  111.80  3.000
 H74  S30  C05  C04  128.07  3.000
 H74  C06  C05  C04  120.12  3.000
 H74  N31  C06  C07  125.26  3.000
 H74  N31  C06  C05  122.87  3.000
 H74  C07  C06  C05  111.88  3.000
 H74  H7   C07  C08  124.22  3.000
 H74  H7   C07  C06  123.83  3.000
 H74  C08  C07  C06  111.96  3.000
 H74  S30  C08  C09  118.71  3.000
 H74  S30  C08  C07  113.78  3.000
 H74  C09  C08  C07  127.50  3.000
 H74  H8   C09  O21  111.49  3.000
 H74  H8   C09  C08  107.37  3.000
 H74  O21  C09  C08  111.17  3.000
 H74  H8   C09  C10  108.38  3.000
 H74  C08  C09  C10  109.73  3.000
 H74  O21  C09  C10  108.65  3.000
 H74  H9   C20  C14  119.32  3.000
 H74  H9   C20  C10  119.25  3.000
 H74  C14  C20  C10  121.43  3.000
 H74  H15  C25  H14  106.68  3.000
 H74  H15  C25  N24  109.23  3.000
 H74  H14  C25  N24  110.78  3.000
 H74  H15  C25  C26  108.93  3.000
 H74  H14  C25  C26  109.35  3.000
 H74  N24  C25  C26  111.74  3.000
 H74  H17  C26  H16  107.05  3.000
 H74  H17  C26  C27  110.95  3.000
 H74  H16  C26  C27  110.05  3.000
 H74  H17  C26  C25  108.88  3.000
 H74  H16  C26  C25  109.06  3.000
 H74  C27  C26  C25  110.76  3.000
 H74  H19  C27  H18  106.63  3.000
 H74  H19  C27  C28  109.46  3.000
 H74  H18  C27  C28  110.63  3.000
 H74  H19  C27  C26  109.66  3.000
 H74  H18  C27  C26  110.80  3.000
 H74  C28  C27  C26  109.61  3.000
 H74  H21  C28  H20  107.19  3.000
 H74  H21  C28  C29  109.43  3.000
 H74  H20  C28  C29  108.85  3.000
 H74  H21  C28  C27  111.02  3.000
 H74  H20  C28  C27  109.43  3.000
 H74  C29  C28  C27  110.82  3.000
 H74  H23  C29  H22  106.58  3.000
 H74  H23  C29  N24  111.70  3.000
 H74  H22  C29  N24  108.56  3.000
 H74  H23  C29  C28  109.00  3.000
 H74  H22  C29  C28  109.73  3.000
 H74  N24  C29  C28  111.16  3.000
 H74  H24  C32  N31  116.44  3.000
 H74  H24  C32  C33  119.53  3.000
 H74  N31  C32  C33  124.03  3.000
 H74  H25  C33  C32  119.80  3.000
 H74  H25  C33  C04  120.05  3.000
 H74  C32  C33  C04  120.15  3.000
 H74  H26  N15  C16  115.96  3.000
 H74  H26  N15  C14  114.46  3.000
 H74  C16  N15  C14  129.56  3.000
 H74  C29  N24  C25  111.22  3.000
 H74  C25  N24  C23  112.40  3.000
 H74  C29  N24  C23  111.74  3.000
 H74  C32  N31  C06  116.83  3.000
 H74  C22  O21  C09  114.30  3.000
 H74  C08  S30  C05   90.58  3.000
 H74  H3   C1   H2   117.02  3.000
 H74  H3   C1   C17  121.06  3.000
 H74  H2   C1   C17  121.92  3.000
 H74  H11  C22  H10  106.64  3.000
 H74  H11  C22  O21  111.03  3.000
 H74  H10  C22  O21  110.15  3.000
 H74  H11  C22  C23  110.60  3.000
 H74  H10  C22  C23  109.01  3.000
 H74  O21  C22  C23  109.35  3.000
 H74  H13  C23  H12  105.98  3.000
 H74  H13  C23  N24  108.55  3.000
 H74  H12  C23  N24  112.38  3.000
 H74  H13  C23  C22  108.34  3.000
 H74  H12  C23  C22  107.48  3.000
 H74  N24  C23  C22  113.76  3.000
 H74  O03  C02  O01  128.03  3.000
 H74  O01  C02  C04  117.12  3.000
 H74  O03  C02  C04  114.85  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
 H74  CONST_01  C13  C14  C20  C10     0.00   0.0  0
 H74  CONST_02  C13  C12  C11  C10     0.00   0.0  0
 H74  CONST_03  C14  C20  C10  C11     0.00   0.0  0
 H74  CONST_04  C14  C13  C12  C11     0.00   0.0  0
 H74  CONST_05  C20  C10  C11  C12     0.00   0.0  0
 H74  CONST_06  C20  C14  C13  C12     0.00   0.0  0
 H74  CONST_07  C07  C06  C05  C04   180.00   0.0  0
 H74  CONST_08  N31  C06  C05  C04     0.00   0.0  0
 H74  CONST_09  C08  S30  C05  C04   180.00   0.0  0
 H74  CONST_10  N31  C32  C33  C04     0.00   0.0  0
 H74  CONST_11  C08  C07  C06  C05     0.00   0.0  0
 H74  CONST_12  C32  N31  C06  C05     0.00   0.0  0
 H74  CONST_13  C07  C08  S30  C05     0.00   0.0  0
 H74  CONST_14  C32  C33  C04  C05     0.00   0.0  0
 H74  CONST_15  S30  C08  C07  C06     0.00   0.0  0
 H74  CONST_16  C33  C32  N31  C06     0.00   0.0  0
 H74  CONST_17  C08  S30  C05  C06     0.00   0.0  0
 H74  CONST_18  C33  C04  C05  C06     0.00   0.0  0
 H74  CONST_19  C32  N31  C06  C07   180.00   0.0  0
 H74  CONST_20  S30  C05  C06  C07     0.00   0.0  0
 H74  CONST_21  N31  C06  C07  C08   180.00   0.0  0
 H74  CONST_22  S30  C05  C04  C33   180.00   0.0  0
 H74  CONST_23  S30  C05  C06  N31   180.00   0.0  0
 H74  CONST_24  N15  C14  C20  C10   180.00   0.0  0
 H74  CONST_25  C09  C10  C11  C12   180.00   0.0  0
 H74  CONST_26  N15  C14  C13  C12   180.00   0.0  0
 H74  CONST_27  C09  C10  C20  C14   180.00   0.0  0
 H74  CONST_28  C06  C05  C04  C02   180.00   0.0  0
 H74  CONST_29  S30  C05  C04  C02     0.00   0.0  0
 H74  CONST_30  C32  C33  C04  C02   180.00   0.0  0
 H74  CONST_31  C09  C08  S30  C05   180.00   0.0  0
 H74  CONST_32  C09  C08  C07  C06   180.00   0.0  0
 H74  CONST_33  H5   C12  C11  C10   180.00   0.0  0
 H74  CONST_34  H9   C20  C10  C11   180.00   0.0  0
 H74  CONST_35  H6   C13  C12  C11   180.00   0.0  0
 H74  CONST_36  H4   C11  C12  C13   180.00   0.0  0
 H74  CONST_37  H24  C32  C33  C04   180.00   0.0  0
 H74  CONST_38  H7   C07  C06  C05   180.00   0.0  0
 H74  CONST_39  H25  C33  C04  C05   180.00   0.0  0
 H74  CONST_40  C16  N15  C14  C13     0.00   0.0  0
 H74  CONST_41  C20  C14  N15  C16   180.00   0.0  0
 H74  CONST_42  H26  N15  C14  C13   180.00   0.0  0
 H74  CONST_43  C14  N15  C16  C17   180.00   0.0  0
 H74  CONST_44  O19  C16  N15  C14     0.00   0.0  0
 H74  Var_01    C28  C27  C26  C25    53.06  30.0  1
 H74  Var_02    C28  C29  N24  C25   -59.19  30.0  1
 H74  Var_03    C29  C28  C27  C26   -53.72  30.0  1
 H74  Var_04    C29  N24  C25  C26    58.86  30.0  1
 H74  Var_05    N24  C29  C28  C27    57.07  30.0  1
 H74  Var_06    N24  C25  C26  C27   -56.03  30.0  1
 H74  Var_07    O03  C02  C04  C05     3.87  30.0  2
 H74  Var_08    O21  C22  C23  N24    66.61  30.0  3
 H74  Var_09    C23  C22  O21  C09  -163.34  30.0  1
 H74  Var_10    C1   C17  C16  N15   179.67  30.0  2
 H74  Var_11    H2   C1   C17  C16     0.00   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
 H74  chir_01  C09  O21  C08  C10  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
 H74  plan-1  C10  0.020
 H74  plan-1  C11  0.020
 H74  plan-1  C12  0.020
 H74  plan-1  C13  0.020
 H74  plan-1  C14  0.020
 H74  plan-1  C09  0.020
 H74  plan-1  C20  0.020
 H74  plan-1  N15  0.020
 H74  plan-1  H4   0.020
 H74  plan-1  H5   0.020
 H74  plan-1  H6   0.020
 H74  plan-1  H9   0.020
 H74  plan-2  C04  0.020
 H74  plan-2  C05  0.020
 H74  plan-2  C06  0.020
 H74  plan-2  C07  0.020
 H74  plan-2  C08  0.020
 H74  plan-2  C09  0.020
 H74  plan-2  C32  0.020
 H74  plan-2  C33  0.020
 H74  plan-2  N31  0.020
 H74  plan-2  S30  0.020
 H74  plan-2  H7   0.020
 H74  plan-2  H24  0.020
 H74  plan-2  H25  0.020
 H74  plan-2  C02  0.020
 H74  plan-3  C17  0.020
 H74  plan-3  C14  0.020
 H74  plan-3  C16  0.020
 H74  plan-3  N15  0.020
 H74  plan-3  O19  0.020
 H74  plan-3  H26  0.020
 H74  plan-4  C04  0.020
 H74  plan-4  O01  0.020
 H74  plan-4  O03  0.020
 H74  plan-4  C02  0.020
 H74  plan-5  C17  0.020
 H74  plan-5  C16  0.020
 H74  plan-5  H1   0.020
 H74  plan-5  C1   0.020
 H74  plan-5  H2   0.020
 H74  plan-5  H3   0.020

