# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Mar 20 09:45:31 2022
#   Inital geometry file: a 149 line input string
#   Ligand name: 3-[(3-chlorophenyl)ethynyl]-2-{4-[2-(cyclopropylamino)-2-oxoethoxy]phenyl}-6-hydroxy-1-benzofuran-5-carboxylic acid
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: OC(=O)c1cc2c(oc(c3ccc(OCC(=O)NC4CC4)cc3)c2C#Cc5cccc(Cl)c5)cc1O
#
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
 N75  N75  '3-[(3-chlorophenyl)ethynyl]-2-{4-[2-(cyclopropylamino)-2-oxoethoxy]phenyl}-6-hydroxy-1-benzofuran-5-carboxylic acid'  ligand  55  36  .  2022-08-10  2023-02-15
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_N75
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
 N75  C1   C   CR16   0  -0.461  31.5311   -6.3203  35.4622
 N75  C2   C   CR6    0   0.365  31.2822   -4.9628  35.6805
 N75  C3   C   CR6    0  -0.281  32.2471   -4.1402  36.3298
 N75  C4   C   CR16   0  -0.433  33.4500   -4.6798  36.7589
 N75  C5   C   CR56   0   0.047  33.7034   -6.0274  36.5492
 N75  C6   C   CR56   0   0.376  32.7424   -6.8036  35.9088
 N75  C7   C   CR5    0  -0.101  34.7930   -6.9272  36.8450
 N75  C8   C   CR5    0   0.373  34.4137   -8.1565  36.3709
 N75  O1   O   O      0  -0.477  33.1777   -8.0787  35.8068
 N75  C9   C   CR6    0  -0.048  35.0472   -9.4582  36.3406
 N75  C10  C   CR16   0  -0.316  36.2388   -9.7108  37.0335
 N75  C11  C   CR16   0  -0.332  36.8410  -10.9496  36.9870
 N75  C12  C   CR6    0   0.391  36.2687  -11.9897  36.2522
 N75  C13  C   CR16   0  -0.357  35.0794  -11.7595  35.5657
 N75  C14  C   CR16   0  -0.277  34.4840  -10.5094  35.6133
 N75  O2   O   O2     0  -0.457  36.9398  -13.1566  36.2567
 N75  C15  C   CH2    0  -0.335  36.4209  -14.2416  35.5369
 N75  C16  C   C      0   0.497  35.2124  -14.8557  36.2403
 N75  N1   N   NH1    0  -0.640  34.4544  -15.6332  35.4503
 N75  O3   O   O      0  -0.462  34.9990  -14.6696  37.4236
 N75  C17  C   CH1    0  -0.079  33.3292  -16.3601  35.9413
 N75  C18  C   CH2    0  -0.510  33.0726  -17.7112  35.3583
 N75  C19  C   CH2    0  -0.482  33.5566  -17.5855  36.7695
 N75  C20  C   CSP    0   0.129  35.9844   -6.5529  37.4894
 N75  C21  C   CSP    0   0.077  36.9699   -6.1678  38.0738
 N75  C22  C   C      0  -0.138  38.1456   -5.7313  38.7404
 N75  C23  C   C1     0  -0.303  39.1007   -6.6561  39.1737
 N75  C24  C   C1     0  -0.248  40.2376   -6.2181  39.8307
 N75  C25  C   C1     0  -0.215  40.4450   -4.8659  40.0680
 N75  C26  C   C      0  -0.029  39.4922   -3.9571  39.6316
 N75  CL   CL  CL     0  -0.121  39.7371   -2.2664  39.9163
 N75  C27  C   C1     0  -0.265  38.3472   -4.3673  38.9729
 N75  C28  C   C      0   0.497  31.9521   -2.6762  36.5508
 N75  O4   O   O      0  -0.539  32.7930   -1.9702  37.1093
 N75  O5   O   OC    -1  -0.627  30.8194   -2.2773  36.1272
 N75  O6   O   OH1    0  -0.654  30.1316   -4.4422  35.2754
 N75  H1   H   HCR6   0   0.265  30.8017   -6.9493  34.9680
 N75  H2   H   HCR6   0   0.247  34.1784   -4.0476  37.2508
 N75  H3   H   HCR6   0   0.269  36.7068   -8.9344  37.6220
 N75  H4   H   HCR6   0   0.268  37.7617  -11.1233  37.5294
 N75  H5   H   HCR6   0   0.282  34.5960  -12.5310  34.9817
 N75  H6   H   HCR6   0   0.264  33.5648  -10.3673  35.0622
 N75  H7   H   HCH2   0   0.261  36.1928  -13.9759  34.4988
 N75  H8   H   HCH2   0   0.306  37.2153  -14.9905  35.5040
 N75  H9   H   HNH1   0   0.406  34.6456  -15.6670  34.4606
 N75  H10  H   HCH1   0   0.269  32.4620  -15.7539  36.1833
 N75  H11  H   HCH2   0   0.260  32.0431  -17.9939  35.1836
 N75  H12  H   HCH2   0   0.259  33.7700  -18.0787  34.6157
 N75  H13  H   HCH2   0   0.256  32.8621  -17.7819  37.5757
 N75  H14  H   HCH2   0   0.256  34.5813  -17.8642  36.9781
 N75  H15  H   H      0   0.269  38.9457   -7.7117  38.9945
 N75  H16  H   H      0   0.274  40.9749   -6.9351  40.1656
 N75  H17  H   H      0   0.284  41.3339   -4.5275  40.5826
 N75  H18  H   H      0   0.283  37.6129   -3.6457  38.6413
 N75  H20  H   HOH1   0   0.459  30.2091   -3.4465  35.5560

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
 N75  C13  C14  aromatic  1.385  0.020  1.385
 N75  C13  C12  aromatic  1.392  0.020  1.392
 N75  C14  C9   aromatic  1.397  0.020  1.397
 N75  C15  O2   single    1.402  0.020  1.402
 N75  C15  C16  single    1.527  0.020  1.527
 N75  O6   C2   single    1.326  0.020  1.326
 N75  C1   C2   aromatic  1.397  0.020  1.397
 N75  C1   C6   aromatic  1.378  0.020  1.378
 N75  O1   C6   aromatic  1.351  0.020  1.351
 N75  O1   C8   aromatic  1.361  0.020  1.361
 N75  C2   C3   aromatic  1.425  0.020  1.425
 N75  C6   C5   aromatic  1.391  0.020  1.391
 N75  C12  O2   single    1.346  0.020  1.346
 N75  C12  C11  aromatic  1.396  0.020  1.396
 N75  C16  O3   double    1.217  0.020  1.217
 N75  C16  N1   single    1.343  0.020  1.343
 N75  C9   C8   single    1.448  0.020  1.448
 N75  C9   C10  aromatic  1.401  0.020  1.401
 N75  C8   C7   aromatic  1.371  0.020  1.371
 N75  N1   C17  single    1.427  0.020  1.427
 N75  C3   C28  single    1.510  0.020  1.510
 N75  C3   C4   aromatic  1.386  0.020  1.386
 N75  C5   C7   aromatic  1.444  0.020  1.444
 N75  C5   C4   aromatic  1.387  0.020  1.387
 N75  O4   C28  deloc     1.232  0.020  1.232
 N75  C7   C20  single    1.405  0.020  1.405
 N75  C11  C10  aromatic  1.378  0.020  1.378
 N75  C28  O5   deloc     1.273  0.020  1.273
 N75  C18  C17  single    1.494  0.020  1.494
 N75  C18  C19  single    1.497  0.020  1.497
 N75  C17  C19  single    1.496  0.020  1.496
 N75  C20  C21  triple    1.209  0.020  1.209
 N75  C23  C24  aromatic  1.384  0.020  1.384
 N75  C23  C22  aromatic  1.398  0.020  1.398
 N75  C21  C22  single    1.420  0.020  1.420
 N75  C24  C25  aromatic  1.388  0.020  1.388
 N75  C22  C27  aromatic  1.398  0.020  1.398
 N75  C25  C26  aromatic  1.387  0.020  1.387
 N75  C27  C26  aromatic  1.383  0.020  1.383
 N75  C26  CL   single    1.732  0.020  1.732
 N75  C1   H1   single    0.930  0.020  1.080
 N75  C4   H2   single    0.930  0.020  1.080
 N75  C10  H3   single    0.930  0.020  1.080
 N75  C11  H4   single    0.930  0.020  1.080
 N75  C13  H5   single    0.930  0.020  1.080
 N75  C14  H6   single    0.930  0.020  1.080
 N75  C15  H7   single    0.970  0.020  1.090
 N75  C15  H8   single    0.970  0.020  1.090
 N75  N1   H9   single    0.860  0.020  1.020
 N75  C17  H10  single    0.970  0.020  1.090
 N75  C18  H11  single    0.970  0.020  1.090
 N75  C18  H12  single    0.970  0.020  1.090
 N75  C19  H13  single    0.970  0.020  1.090
 N75  C19  H14  single    0.970  0.020  1.090
 N75  C23  H15  single    0.930  0.020  1.080
 N75  C24  H16  single    0.930  0.020  1.080
 N75  C25  H17  single    0.930  0.020  1.080
 N75  C27  H18  single    0.930  0.020  1.080
 N75  O6   H20  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
 N75  H1   C1   C6   122.43  3.000
 N75  H1   C1   C2   121.05  3.000
 N75  C6   C1   C2   116.52  3.000
 N75  O6   C2   C3   120.01  3.000
 N75  C3   C2   C1   120.77  3.000
 N75  O6   C2   C1   119.22  3.000
 N75  C28  C3   C4   120.11  3.000
 N75  C4   C3   C2   120.26  3.000
 N75  C28  C3   C2   119.62  3.000
 N75  H2   C4   C5   120.87  3.000
 N75  H2   C4   C3   119.80  3.000
 N75  C5   C4   C3   119.33  3.000
 N75  C7   C5   C6   105.54  3.000
 N75  C7   C5   C4   135.43  3.000
 N75  C6   C5   C4   119.03  3.000
 N75  O1   C6   C5   109.80  3.000
 N75  C5   C6   C1   124.08  3.000
 N75  O1   C6   C1   126.12  3.000
 N75  C20  C7   C8   129.19  3.000
 N75  C20  C7   C5   124.59  3.000
 N75  C8   C7   C5   106.21  3.000
 N75  C9   C8   O1   116.10  3.000
 N75  C9   C8   C7   133.81  3.000
 N75  O1   C8   C7   110.08  3.000
 N75  C8   O1   C6   108.37  3.000
 N75  C14  C9   C10  117.68  3.000
 N75  C10  C9   C8   121.58  3.000
 N75  C14  C9   C8   120.74  3.000
 N75  H3   C10  C11  118.35  3.000
 N75  H3   C10  C9   120.52  3.000
 N75  C11  C10  C9   121.13  3.000
 N75  H4   C11  C12  119.53  3.000
 N75  H4   C11  C10  119.93  3.000
 N75  C12  C11  C10  120.54  3.000
 N75  O2   C12  C13  124.80  3.000
 N75  O2   C12  C11  116.08  3.000
 N75  C13  C12  C11  119.11  3.000
 N75  H5   C13  C14  118.04  3.000
 N75  H5   C13  C12  122.01  3.000
 N75  C14  C13  C12  119.95  3.000
 N75  H6   C14  C13  117.81  3.000
 N75  H6   C14  C9   120.61  3.000
 N75  C13  C14  C9   121.58  3.000
 N75  C15  O2   C12  119.00  3.000
 N75  H8   C15  H7   106.81  3.000
 N75  H8   C15  C16  108.28  3.000
 N75  H7   C15  C16  111.67  3.000
 N75  H8   C15  O2   106.08  3.000
 N75  H7   C15  O2   112.08  3.000
 N75  C16  C15  O2   111.57  3.000
 N75  O3   C16  N1   124.17  3.000
 N75  N1   C16  C15  114.11  3.000
 N75  O3   C16  C15  121.69  3.000
 N75  H9   N1   C17  118.04  3.000
 N75  H9   N1   C16  119.33  3.000
 N75  C17  N1   C16  122.53  3.000
 N75  H10  C17  C19  117.09  3.000
 N75  H10  C17  C18  117.06  3.000
 N75  C19  C17  C18   60.09  3.000
 N75  H10  C17  N1   114.98  3.000
 N75  C19  C17  N1   119.20  3.000
 N75  C18  C17  N1   117.52  3.000
 N75  H12  C18  H11  114.42  3.000
 N75  H12  C18  C19  117.82  3.000
 N75  H11  C18  C19  118.81  3.000
 N75  H12  C18  C17  117.64  3.000
 N75  H11  C18  C17  117.57  3.000
 N75  C19  C18  C17   60.05  3.000
 N75  H14  C19  H13  114.66  3.000
 N75  H14  C19  C18  117.79  3.000
 N75  H13  C19  C18  118.66  3.000
 N75  H14  C19  C17  117.48  3.000
 N75  H13  C19  C17  117.61  3.000
 N75  C18  C19  C17   59.86  3.000
 N75  C21  C20  C7   180.00  3.000
 N75  C22  C21  C20  180.00  3.000
 N75  C27  C22  C23  119.68  3.000
 N75  C27  C22  C21  119.82  3.000
 N75  C23  C22  C21  120.50  3.000
 N75  H15  C23  C24  120.34  3.000
 N75  H15  C23  C22  119.74  3.000
 N75  C24  C23  C22  119.92  3.000
 N75  H16  C24  C25  119.40  3.000
 N75  H16  C24  C23  119.80  3.000
 N75  C25  C24  C23  120.80  3.000
 N75  H17  C25  C26  120.62  3.000
 N75  H17  C25  C24  120.59  3.000
 N75  C26  C25  C24  118.80  3.000
 N75  C27  C26  CL   119.00  3.000
 N75  CL   C26  C25  119.39  3.000
 N75  C27  C26  C25  121.61  3.000
 N75  H18  C27  C26  120.68  3.000
 N75  H18  C27  C22  120.12  3.000
 N75  C26  C27  C22  119.20  3.000
 N75  O5   C28  O4   125.34  3.000
 N75  O5   C28  C3   115.40  3.000
 N75  O4   C28  C3   119.26  3.000
 N75  H20  O6   C2   103.26  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
 N75  CONST_01  C4   C3   C2   C1      0.00   0.0  0
 N75  CONST_02  C8   O1   C6   C1    180.00   0.0  0
 N75  CONST_03  C7   C5   C6   C1    180.00   0.0  0
 N75  CONST_04  C4   C5   C6   C1      0.00   0.0  0
 N75  CONST_05  O1   C6   C1   C2    180.00   0.0  0
 N75  CONST_06  C5   C6   C1   C2      0.00   0.0  0
 N75  CONST_07  C5   C4   C3   C2      0.00   0.0  0
 N75  CONST_08  C6   C1   C2   C3      0.00   0.0  0
 N75  CONST_09  C6   C5   C4   C3      0.00   0.0  0
 N75  CONST_10  C7   C5   C4   C3    180.00   0.0  0
 N75  CONST_11  O1   C6   C5   C4    180.00   0.0  0
 N75  CONST_12  C8   C7   C5   C4    180.00   0.0  0
 N75  CONST_13  C8   O1   C6   C5      0.00   0.0  0
 N75  CONST_14  O1   C8   C7   C5      0.00   0.0  0
 N75  CONST_15  C9   C8   C7   C5    180.00   0.0  0
 N75  CONST_16  C9   C8   O1   C6    180.00   0.0  0
 N75  CONST_17  C7   C8   O1   C6      0.00   0.0  0
 N75  CONST_18  C8   C7   C5   C6      0.00   0.0  0
 N75  CONST_19  C14  C9   C8   C7    180.00   0.0  0
 N75  CONST_20  C10  C9   C8   C7      0.00   0.0  0
 N75  CONST_21  O1   C6   C5   C7      0.00   0.0  0
 N75  CONST_22  C13  C14  C9   C8    180.00   0.0  0
 N75  CONST_23  C11  C10  C9   C8    180.00   0.0  0
 N75  CONST_24  C14  C9   C8   O1      0.00   0.0  0
 N75  CONST_25  C10  C9   C8   O1    180.00   0.0  0
 N75  CONST_26  C12  C13  C14  C9      0.00   0.0  0
 N75  CONST_27  C12  C11  C10  C9      0.00   0.0  0
 N75  CONST_28  C13  C14  C9   C10     0.00   0.0  0
 N75  CONST_29  C13  C12  C11  C10     0.00   0.0  0
 N75  CONST_30  C14  C13  C12  C11     0.00   0.0  0
 N75  CONST_31  C14  C9   C10  C11     0.00   0.0  0
 N75  CONST_32  C25  C24  C23  C22     0.00   0.0  0
 N75  CONST_33  C25  C26  C27  C22     0.00   0.0  0
 N75  CONST_34  C26  C25  C24  C23     0.00   0.0  0
 N75  CONST_35  C26  C27  C22  C23     0.00   0.0  0
 N75  CONST_36  C27  C22  C23  C24     0.00   0.0  0
 N75  CONST_37  C27  C26  C25  C24     0.00   0.0  0
 N75  CONST_38  C28  C3   C2   C1    180.00   0.0  0
 N75  CONST_39  O6   C2   C3   C4    180.00   0.0  0
 N75  CONST_40  C20  C7   C5   C4      0.00   0.0  0
 N75  CONST_41  C28  C3   C4   C5    180.00   0.0  0
 N75  CONST_42  O6   C2   C1   C6    180.00   0.0  0
 N75  CONST_43  C20  C7   C5   C6    180.00   0.0  0
 N75  CONST_44  C20  C7   C8   O1    180.00   0.0  0
 N75  CONST_45  C20  C7   C8   C9      0.00   0.0  0
 N75  CONST_46  O2   C12  C11  C10   180.00   0.0  0
 N75  CONST_47  O2   C12  C13  C14   180.00   0.0  0
 N75  CONST_48  C24  C23  C22  C21   180.00   0.0  0
 N75  CONST_49  C26  C27  C22  C21   180.00   0.0  0
 N75  CONST_50  CL   C26  C27  C22   180.00   0.0  0
 N75  CONST_51  CL   C26  C25  C24   180.00   0.0  0
 N75  CONST_52  H2   C4   C3   C2    180.00   0.0  0
 N75  CONST_53  H1   C1   C2   C3    180.00   0.0  0
 N75  CONST_54  H6   C14  C9   C8      0.00   0.0  0
 N75  CONST_55  H3   C10  C9   C8      0.00   0.0  0
 N75  CONST_56  H5   C13  C14  C9    180.00   0.0  0
 N75  CONST_57  H4   C11  C10  C9    180.00   0.0  0
 N75  CONST_58  H16  C24  C23  C22   180.00   0.0  0
 N75  CONST_59  H17  C25  C24  C23   180.00   0.0  0
 N75  CONST_60  H18  C27  C22  C23   180.00   0.0  0
 N75  CONST_61  H15  C23  C24  C25   180.00   0.0  0
 N75  CONST_62  C17  N1   C16  C15   180.00   0.0  0
 N75  CONST_63  C17  N1   C16  O3      0.00   0.0  0
 N75  CONST_64  H9   N1   C16  C15     0.00   0.0  0
 N75  Var_01    C19  C18  C17  N1    109.56  30.0  1
 N75  Var_02    H13  C19  C18  C17   107.07  30.0  1
 N75  Var_03    O4   C28  C3   C2   -179.78  30.0  2
 N75  Var_04    C18  C17  N1   C16  -143.60  30.0  3
 N75  Var_05    C16  C15  O2   C12   -74.12  30.0  1
 N75  Var_06    O3   C16  C15  O2    -19.48  30.0  3

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
 N75  chir_01  C17  N1  C18  C19  both

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
 N75  plan-1  C8   0.020
 N75  plan-1  C9   0.020
 N75  plan-1  C10  0.020
 N75  plan-1  C11  0.020
 N75  plan-1  C12  0.020
 N75  plan-1  C13  0.020
 N75  plan-1  C14  0.020
 N75  plan-1  O2   0.020
 N75  plan-1  H3   0.020
 N75  plan-1  H4   0.020
 N75  plan-1  H5   0.020
 N75  plan-1  H6   0.020
 N75  plan-2  C20  0.020
 N75  plan-2  C21  0.020
 N75  plan-2  C22  0.020
 N75  plan-2  C23  0.020
 N75  plan-2  C24  0.020
 N75  plan-2  C25  0.020
 N75  plan-2  C26  0.020
 N75  plan-2  CL   0.020
 N75  plan-2  C27  0.020
 N75  plan-2  H15  0.020
 N75  plan-2  H16  0.020
 N75  plan-2  H17  0.020
 N75  plan-2  H18  0.020
 N75  plan-3  C1   0.020
 N75  plan-3  C2   0.020
 N75  plan-3  C3   0.020
 N75  plan-3  C4   0.020
 N75  plan-3  C5   0.020
 N75  plan-3  C6   0.020
 N75  plan-3  C7   0.020
 N75  plan-3  C8   0.020
 N75  plan-3  O1   0.020
 N75  plan-3  C9   0.020
 N75  plan-3  C20  0.020
 N75  plan-3  C21  0.020
 N75  plan-3  C28  0.020
 N75  plan-3  O6   0.020
 N75  plan-3  H1   0.020
 N75  plan-3  H2   0.020
 N75  plan-4  C15  0.020
 N75  plan-4  C16  0.020
 N75  plan-4  N1   0.020
 N75  plan-4  O3   0.020
 N75  plan-4  C17  0.020
 N75  plan-4  H9   0.020
 N75  plan-5  C3   0.020
 N75  plan-5  C28  0.020
 N75  plan-5  O4   0.020
 N75  plan-5  O5   0.020

