# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sun Apr  5 14:05:21 2020
#   Inital geometry file: a 135 line input string
#   Ligand name: (5R)-3,5-bis(4-chlorobenzyl)-4-(6-chloro-1H-indol-3-yl)-5-hydroxyfuran-2(5H)-one
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: O[C@]1(Cc2ccc(Cl)cc2)OC(=O)C(=C1c3c[nH]c4cc(Cl)ccc34)Cc5ccc(Cl)cc5
#
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
 4NX  4NX  (5R)-3,5-bis(4-chlorobenzyl)-4-(6-chloro-1H-indol-3-yl)-5-hydroxyfuran-2(5H)-one  ligand  51  33  .  2022-07-23  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_4NX
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
 4NX  CL1  CL  CL    0  -0.133  -1.8679  -6.8200   0.5807
 4NX  C40  C   CR6   0  -0.057  -1.8790  -5.1842   0.0024
 4NX  C39  C   CR16  0  -0.196  -1.7497  -4.1408   0.9069
 4NX  C38  C   CR16  0  -0.288  -1.7603  -2.8377   0.4354
 4NX  C41  C   CR16  0  -0.196  -2.0192  -4.9406  -1.3537
 4NX  C42  C   CR16  0  -0.323  -2.0270  -3.6282  -1.8063
 4NX  C37  C   CR6   0   0.152  -1.9023  -2.5634  -0.9227
 4NX  C28  C   CH2   0  -0.622  -1.9107  -1.1340  -1.4078
 4NX  C15  C   CR5   0  -0.135  -0.5878  -0.4922  -1.1619
 4NX  C16  C   CR5   0   0.573   0.6224  -0.9566  -1.8548
 4NX  O20  O   O     0  -0.418   0.7264  -1.7984  -2.7053
 4NX  O18  O   O     0  -0.474   1.6793  -0.2727  -1.3916
 4NX  C13  C   CR5   0   0.419   1.2750   0.6396  -0.3608
 4NX  O21  O   OH1   0  -0.627   1.5617   1.9276  -0.7351
 4NX  C5   C   CH2   0  -0.581   1.9734   0.2015   0.9353
 4NX  C6   C   CR6   0   0.113   3.4660   0.3518   0.8584
 4NX  C11  C   CR16  0  -0.289   4.2648  -0.6559   0.3211
 4NX  C10  C   CR16  0  -0.195   5.6384  -0.5052   0.2246
 4NX  C7   C   CR16  0  -0.323   4.0805   1.5221   1.2969
 4NX  C8   C   CR16  0  -0.195   5.4550   1.6930   1.2022
 4NX  C9   C   CR6   0  -0.051   6.2224   0.6745   0.6629
 4NX  CL2  CL  CL    0  -0.127   7.9419   0.8668   0.5428
 4NX  C14  C   CR5   0   0.035  -0.2314   0.4735  -0.3070
 4NX  C44  C   CR5   0   0.020  -1.0929   1.3279   0.4847
 4NX  C48  C   CR15  0  -0.059  -0.9851   1.6566   1.8149
 4NX  N49  N   NR15  0  -0.683  -1.9976   2.4848   2.1703
 4NX  C46  C   CR56  0   0.364  -2.7878   2.7390   1.0884
 4NX  C45  C   CR56  0   0.025  -2.2527   2.0246  -0.0019
 4NX  C56  C   CR16  0  -0.261  -3.9146   3.5498   0.9787
 4NX  C57  C   CR6   0  -0.064  -4.4912   3.6287  -0.2703
 4NX  CL3  CL  CL    0  -0.134  -5.9029   4.6176  -0.4831
 4NX  C58  C   CR16  0  -0.220  -3.9794   2.9480  -1.3839
 4NX  C59  C   CR16  0  -0.382  -2.8605   2.1517  -1.2540
 4NX  H1   H   HCR6  0   0.279  -1.6440  -4.3377   1.9652
 4NX  H2   H   HCR6  0   0.257  -1.6615  -2.0241   1.1447
 4NX  H3   H   HCR6  0   0.279  -2.1175  -5.7593  -2.0534
 4NX  H4   H   HCR6  0   0.261  -2.1332  -3.4392  -2.8670
 4NX  H5   H   HCH2  0   0.283  -2.1503  -1.1050  -2.4730
 4NX  H6   H   HCH2  0   0.283  -2.6933  -0.5788  -0.8898
 4NX  H7   H   HOH1  0   0.471   2.5132   2.0909  -0.6771
 4NX  H8   H   HCH2  0   0.282   1.5925   0.8097   1.7560
 4NX  H9   H   HCH2  0   0.287   1.6976  -0.8330   1.1503
 4NX  H10  H   HCR6  0   0.264   3.8154  -1.5797  -0.0185
 4NX  H11  H   HCR6  0   0.282   6.2453  -1.2995  -0.1883
 4NX  H12  H   HCR6  0   0.273   3.4870   2.3127   1.7404
 4NX  H13  H   HCR6  0   0.283   5.9158   2.6066   1.5518
 4NX  H14  H   HCR5  0   0.300  -0.2739   1.3336   2.5571
 4NX  H15  H   HNR5  0   0.423  -2.1361   2.8505   3.0986
 4NX  H16  H   HCR6  0   0.289  -4.3089   4.0939   1.8264
 4NX  H17  H   HCR6  0   0.275  -4.4609   3.0533  -2.3463
 4NX  H18  H   HCR6  0   0.261  -2.4656   1.6420  -2.1233

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
 4NX  CL2  C9   single    1.734  0.020  1.734
 4NX  C10  C9   aromatic  1.387  0.020  1.387
 4NX  C10  C11  aromatic  1.385  0.020  1.385
 4NX  CL1  C40  single    1.735  0.020  1.735
 4NX  C9   C8   aromatic  1.385  0.020  1.385
 4NX  C39  C40  aromatic  1.387  0.020  1.387
 4NX  C39  C38  aromatic  1.386  0.020  1.386
 4NX  C11  C6   aromatic  1.394  0.020  1.394
 4NX  C40  C41  aromatic  1.385  0.020  1.385
 4NX  O20  C16  double    1.201  0.020  1.201
 4NX  C38  C37  aromatic  1.393  0.020  1.393
 4NX  C8   C7   aromatic  1.388  0.020  1.388
 4NX  C6   C7   aromatic  1.393  0.020  1.393
 4NX  C6   C5   single    1.502  0.020  1.502
 4NX  C41  C42  aromatic  1.388  0.020  1.388
 4NX  C16  O18  single    1.341  0.020  1.341
 4NX  C16  C15  single    1.470  0.020  1.470
 4NX  O18  C13  single    1.435  0.020  1.435
 4NX  C37  C42  aromatic  1.389  0.020  1.389
 4NX  C37  C28  single    1.510  0.020  1.510
 4NX  C5   C13  single    1.536  0.020  1.536
 4NX  C15  C28  single    1.491  0.020  1.491
 4NX  C15  C14  double    1.338  0.020  1.338
 4NX  C13  C14  single    1.516  0.020  1.516
 4NX  C13  O21  single    1.372  0.020  1.372
 4NX  C14  C44  single    1.449  0.020  1.449
 4NX  C44  C48  aromatic  1.374  0.020  1.374
 4NX  C44  C45  aromatic  1.438  0.020  1.438
 4NX  C48  N49  aromatic  1.355  0.020  1.355
 4NX  N49  C46  aromatic  1.364  0.020  1.364
 4NX  C45  C59  aromatic  1.398  0.020  1.398
 4NX  C45  C46  aromatic  1.409  0.020  1.409
 4NX  C59  C58  aromatic  1.379  0.020  1.379
 4NX  C46  C56  aromatic  1.393  0.020  1.393
 4NX  C58  C57  aromatic  1.402  0.020  1.402
 4NX  C56  C57  aromatic  1.378  0.020  1.378
 4NX  C57  CL3  single    1.737  0.020  1.737
 4NX  C39  H1   single    0.930  0.020  1.080
 4NX  C38  H2   single    0.930  0.020  1.080
 4NX  C41  H3   single    0.930  0.020  1.080
 4NX  C42  H4   single    0.930  0.020  1.080
 4NX  C28  H5   single    0.970  0.020  1.090
 4NX  C28  H6   single    0.970  0.020  1.090
 4NX  O21  H7   single    0.850  0.020  0.980
 4NX  C5   H8   single    0.970  0.020  1.090
 4NX  C5   H9   single    0.970  0.020  1.090
 4NX  C11  H10  single    0.930  0.020  1.080
 4NX  C10  H11  single    0.930  0.020  1.080
 4NX  C7   H12  single    0.930  0.020  1.080
 4NX  C8   H13  single    0.930  0.020  1.080
 4NX  C48  H14  single    0.930  0.020  1.080
 4NX  N49  H15  single    0.860  0.020  1.020
 4NX  C56  H16  single    0.930  0.020  1.080
 4NX  C58  H17  single    0.930  0.020  1.080
 4NX  C59  H18  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
 4NX  C41  C40  C39  121.04  3.000
 4NX  C41  C40  CL1  119.53  3.000
 4NX  C39  C40  CL1  119.43  3.000
 4NX  H1   C39  C38  120.32  3.000
 4NX  H1   C39  C40  120.68  3.000
 4NX  C38  C39  C40  119.00  3.000
 4NX  H2   C38  C37  119.97  3.000
 4NX  H2   C38  C39  118.85  3.000
 4NX  C37  C38  C39  121.18  3.000
 4NX  H3   C41  C42  120.28  3.000
 4NX  H3   C41  C40  120.64  3.000
 4NX  C42  C41  C40  119.08  3.000
 4NX  H4   C42  C37  119.88  3.000
 4NX  H4   C42  C41  119.01  3.000
 4NX  C37  C42  C41  121.11  3.000
 4NX  C28  C37  C42  121.39  3.000
 4NX  C28  C37  C38  120.03  3.000
 4NX  C42  C37  C38  118.58  3.000
 4NX  H6   C28  H5   107.00  3.000
 4NX  H6   C28  C15  109.84  3.000
 4NX  H5   C28  C15  110.13  3.000
 4NX  H6   C28  C37  109.47  3.000
 4NX  H5   C28  C37  109.86  3.000
 4NX  C15  C28  C37  110.47  3.000
 4NX  C14  C15  C16  108.05  3.000
 4NX  C14  C15  C28  130.73  3.000
 4NX  C16  C15  C28  121.12  3.000
 4NX  O18  C16  O20  122.25  3.000
 4NX  O18  C16  C15  108.96  3.000
 4NX  O20  C16  C15  128.79  3.000
 4NX  C13  O18  C16  110.50  3.000
 4NX  C14  C13  C5   112.98  3.000
 4NX  C14  C13  O21  108.67  3.000
 4NX  C5   C13  O21  113.77  3.000
 4NX  O21  C13  O18  110.01  3.000
 4NX  C14  C13  O18  103.64  3.000
 4NX  C5   C13  O18  107.26  3.000
 4NX  H7   O21  C13  110.35  3.000
 4NX  H9   C5   H8   106.98  3.000
 4NX  H9   C5   C6   110.85  3.000
 4NX  H8   C5   C6   109.26  3.000
 4NX  H9   C5   C13  108.75  3.000
 4NX  H8   C5   C13  108.49  3.000
 4NX  C6   C5   C13  112.34  3.000
 4NX  C7   C6   C11  118.43  3.000
 4NX  C7   C6   C5   120.43  3.000
 4NX  C11  C6   C5   121.13  3.000
 4NX  H10  C11  C10  118.87  3.000
 4NX  H10  C11  C6   120.02  3.000
 4NX  C10  C11  C6   121.10  3.000
 4NX  H11  C10  C9   120.59  3.000
 4NX  H11  C10  C11  120.21  3.000
 4NX  C9   C10  C11  119.20  3.000
 4NX  H12  C7   C8   118.71  3.000
 4NX  H12  C7   C6   120.03  3.000
 4NX  C8   C7   C6   121.26  3.000
 4NX  H13  C8   C9   120.75  3.000
 4NX  H13  C8   C7   120.25  3.000
 4NX  C9   C8   C7   119.00  3.000
 4NX  CL2  C9   C8   119.66  3.000
 4NX  C8   C9   C10  121.01  3.000
 4NX  CL2  C9   C10  119.32  3.000
 4NX  C44  C14  C13  123.06  3.000
 4NX  C44  C14  C15  128.05  3.000
 4NX  C13  C14  C15  108.72  3.000
 4NX  C45  C44  C48  105.96  3.000
 4NX  C45  C44  C14  125.48  3.000
 4NX  C48  C44  C14  128.55  3.000
 4NX  H14  C48  N49  119.71  3.000
 4NX  H14  C48  C44  130.29  3.000
 4NX  N49  C48  C44  109.96  3.000
 4NX  H15  N49  C46  125.72  3.000
 4NX  H15  N49  C48  124.49  3.000
 4NX  C46  N49  C48  109.80  3.000
 4NX  C56  C46  C45  122.79  3.000
 4NX  C56  C46  N49  129.79  3.000
 4NX  C45  C46  N49  107.42  3.000
 4NX  C59  C45  C46  118.81  3.000
 4NX  C46  C45  C44  106.86  3.000
 4NX  C59  C45  C44  134.27  3.000
 4NX  H16  C56  C57  121.94  3.000
 4NX  H16  C56  C46  121.74  3.000
 4NX  C57  C56  C46  116.32  3.000
 4NX  C58  C57  CL3  118.42  3.000
 4NX  CL3  C57  C56  118.93  3.000
 4NX  C58  C57  C56  122.65  3.000
 4NX  H17  C58  C59  120.09  3.000
 4NX  H17  C58  C57  119.81  3.000
 4NX  C59  C58  C57  120.11  3.000
 4NX  H18  C59  C58  119.48  3.000
 4NX  H18  C59  C45  121.20  3.000
 4NX  C58  C59  C45  119.32  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
 4NX  CONST_01  C37  C38  C39  C40    0.00   0.0  0
 4NX  CONST_02  C37  C42  C41  C40    0.00   0.0  0
 4NX  CONST_03  C42  C41  C40  C39    0.00   0.0  0
 4NX  CONST_04  C42  C37  C38  C39    0.00   0.0  0
 4NX  CONST_05  C41  C40  C39  C38    0.00   0.0  0
 4NX  CONST_06  C41  C42  C37  C38    0.00   0.0  0
 4NX  CONST_07  C9   C10  C11  C6     0.00   0.0  0
 4NX  CONST_08  C9   C8   C7   C6     0.00   0.0  0
 4NX  CONST_09  C8   C9   C10  C11    0.00   0.0  0
 4NX  CONST_10  C8   C7   C6   C11    0.00   0.0  0
 4NX  CONST_11  C7   C8   C9   C10    0.00   0.0  0
 4NX  CONST_12  C7   C6   C11  C10    0.00   0.0  0
 4NX  CONST_13  C46  N49  C48  C44    0.00   0.0  0
 4NX  CONST_14  C58  C59  C45  C44  180.00   0.0  0
 4NX  CONST_15  N49  C46  C45  C44    0.00   0.0  0
 4NX  CONST_16  C56  C46  C45  C44  180.00   0.0  0
 4NX  CONST_17  C59  C45  C44  C48  180.00   0.0  0
 4NX  CONST_18  C46  C45  C44  C48    0.00   0.0  0
 4NX  CONST_19  C45  C46  N49  C48    0.00   0.0  0
 4NX  CONST_20  C56  C46  N49  C48  180.00   0.0  0
 4NX  CONST_21  C45  C44  C48  N49    0.00   0.0  0
 4NX  CONST_22  C59  C45  C46  N49  180.00   0.0  0
 4NX  CONST_23  C57  C56  C46  N49  180.00   0.0  0
 4NX  CONST_24  C58  C59  C45  C46    0.00   0.0  0
 4NX  CONST_25  C58  C57  C56  C46    0.00   0.0  0
 4NX  CONST_26  C57  C58  C59  C45    0.00   0.0  0
 4NX  CONST_27  C57  C56  C46  C45    0.00   0.0  0
 4NX  CONST_28  C59  C45  C46  C56    0.00   0.0  0
 4NX  CONST_29  C59  C58  C57  C56    0.00   0.0  0
 4NX  CONST_30  N49  C48  C44  C14  180.00   0.0  0
 4NX  CONST_31  C59  C45  C44  C14    0.00   0.0  0
 4NX  CONST_32  C46  C45  C44  C14  180.00   0.0  0
 4NX  CONST_33  C38  C39  C40  CL1  180.00   0.0  0
 4NX  CONST_34  C42  C41  C40  CL1  180.00   0.0  0
 4NX  CONST_35  C28  C37  C38  C39  180.00   0.0  0
 4NX  CONST_36  C28  C37  C42  C41  180.00   0.0  0
 4NX  CONST_37  C10  C11  C6   C5   180.00   0.0  0
 4NX  CONST_38  C8   C7   C6   C5   180.00   0.0  0
 4NX  CONST_39  CL2  C9   C10  C11  180.00   0.0  0
 4NX  CONST_40  CL2  C9   C8   C7   180.00   0.0  0
 4NX  CONST_41  CL3  C57  C56  C46  180.00   0.0  0
 4NX  CONST_42  C59  C58  C57  CL3  180.00   0.0  0
 4NX  CONST_43  H2   C38  C39  C40  180.00   0.0  0
 4NX  CONST_44  H4   C42  C41  C40  180.00   0.0  0
 4NX  CONST_45  H3   C41  C40  C39  180.00   0.0  0
 4NX  CONST_46  H1   C39  C40  C41  180.00   0.0  0
 4NX  CONST_47  H11  C10  C11  C6   180.00   0.0  0
 4NX  CONST_48  H13  C8   C7   C6   180.00   0.0  0
 4NX  CONST_49  H12  C7   C6   C11  180.00   0.0  0
 4NX  CONST_50  H10  C11  C6   C7   180.00   0.0  0
 4NX  CONST_51  H14  C48  C44  C14    0.00   0.0  0
 4NX  CONST_52  H15  N49  C48  C44  180.00   0.0  0
 4NX  CONST_53  H18  C59  C45  C44    0.00   0.0  0
 4NX  CONST_54  H16  C56  C46  N49    0.00   0.0  0
 4NX  CONST_55  H17  C58  C59  C45  180.00   0.0  0
 4NX  Var_01    C48  C44  C14  C15  133.99  30.0  2
 4NX  Var_02    C13  C14  C15  C16   -2.67  30.0  1
 4NX  Var_03    C14  C15  C16  O18    0.70  30.0  1
 4NX  Var_04    C15  C28  C37  C38   65.10  30.0  2
 4NX  Var_05    C16  C15  C28  C37   65.47  30.0  2
 4NX  Var_06    C11  C6   C5   C13  -86.02  30.0  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
 4NX  chir_01  C13  O18  C14  O21  positiv

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
 4NX  plan-1  CL1  0.020
 4NX  plan-1  C40  0.020
 4NX  plan-1  C39  0.020
 4NX  plan-1  C38  0.020
 4NX  plan-1  C41  0.020
 4NX  plan-1  C42  0.020
 4NX  plan-1  C37  0.020
 4NX  plan-1  C28  0.020
 4NX  plan-1  H1   0.020
 4NX  plan-1  H2   0.020
 4NX  plan-1  H3   0.020
 4NX  plan-1  H4   0.020
 4NX  plan-2  C15  0.020
 4NX  plan-2  C16  0.020
 4NX  plan-2  O20  0.020
 4NX  plan-2  O18  0.020
 4NX  plan-3  C5   0.020
 4NX  plan-3  C6   0.020
 4NX  plan-3  C11  0.020
 4NX  plan-3  C10  0.020
 4NX  plan-3  C7   0.020
 4NX  plan-3  C8   0.020
 4NX  plan-3  C9   0.020
 4NX  plan-3  CL2  0.020
 4NX  plan-3  H10  0.020
 4NX  plan-3  H11  0.020
 4NX  plan-3  H12  0.020
 4NX  plan-3  H13  0.020
 4NX  plan-4  C14  0.020
 4NX  plan-4  C44  0.020
 4NX  plan-4  C48  0.020
 4NX  plan-4  N49  0.020
 4NX  plan-4  C46  0.020
 4NX  plan-4  C45  0.020
 4NX  plan-4  C56  0.020
 4NX  plan-4  C57  0.020
 4NX  plan-4  CL3  0.020
 4NX  plan-4  C58  0.020
 4NX  plan-4  C59  0.020
 4NX  plan-4  H14  0.020
 4NX  plan-4  H15  0.020
 4NX  plan-4  H16  0.020
 4NX  plan-4  H17  0.020
 4NX  plan-4  H18  0.020

