# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  8 07:01:14 2020
#   Inital geometry file: a 133 line input string
#   Ligand name: 6-chloranyl-~{N}-methylsulfonyl-3-(3-naphthalen-1-yloxypropyl)-1~{H}-indole-2-carboxamide
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: C[S](=O)(=O)NC(=O)c1[nH]c2cc(Cl)ccc2c1CCCOc3cccc4ccccc34
#
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
 5WL  5WL  6-chloranyl-~{N}-methylsulfonyl-3-(3-naphthalen-1-yloxypropyl)-1~{H}-indole-2-carboxamide  ligand  52  31  .  2021-08-04  2021-08-04  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_5WL
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
 5WL  CAA  C   CH3   0  -0.791   2.4042  -5.1445  -1.1079
 5WL  SBE  S   S     0   1.359   2.9752  -4.4634   0.4233
 5WL  OAC  O   OS    0  -0.640   1.9485  -4.6188   1.4328
 5WL  OAD  O   OS    0  -0.651   4.3222  -4.9326   0.6887
 5WL  NAS  N   NC1   0  -0.843   3.1661  -2.8208   0.1156
 5WL  CAV  C   C     0   0.541   2.1097  -1.9562  -0.0830
 5WL  OAB  O   O     0  -0.424   0.9737  -2.3558  -0.2295
 5WL  CAZ  C   CR5   0   0.179   2.4631  -0.5373  -0.1056
 5WL  NAT  N   NR15  0  -0.757   3.6276  -0.0477   0.4472
 5WL  CBB  C   CR56  0   0.361   3.6672   1.2955   0.2742
 5WL  CAO  C   CR16  0  -0.268   4.6278   2.2201   0.6883
 5WL  CAW  C   CR6   0  -0.059   4.3908   3.5332   0.3544
 5WL  CL   CL  CL    0  -0.126   5.5416   4.7397   0.8329
 5WL  CAJ  C   CR16  0  -0.223   3.2536   3.9478  -0.3622
 5WL  CAN  C   CR16  0  -0.364   2.3150   3.0229  -0.7573
 5WL  CBD  C   CR56  0   0.051   2.5080   1.6730  -0.4352
 5WL  CAY  C   CR5   0   0.076   1.7453   0.4917  -0.6717
 5WL  CAR  C   CH2   0  -0.546   0.4401   0.4315  -1.3912
 5WL  CAP  C   CH2   0  -0.454  -0.7536   0.5497  -0.4412
 5WL  CAQ  C   CH2   0  -0.177  -2.0563   0.4628  -1.2080
 5WL  OAU  O   O2    0  -0.467  -3.1211   0.5687  -0.2776
 5WL  CAX  C   CR6   0   0.367  -4.3877   0.5408  -0.7216
 5WL  CBC  C   CR66  0  -0.020  -5.3878   0.6714   0.2902
 5WL  CAM  C   CR16  0  -0.287  -5.0585   0.8144   1.6582
 5WL  CAG  C   CR16  0  -0.257  -6.0428   0.9371   2.6029
 5WL  CAF  C   CR16  0  -0.252  -7.3995   0.9228   2.2250
 5WL  CAK  C   CR16  0  -0.317  -7.7438   0.7858   0.9076
 5WL  CBA  C   CR66  0   0.126  -6.7533   0.6555  -0.0937
 5WL  CAL  C   CR16  0  -0.346  -7.0973   0.5111  -1.4601
 5WL  CAH  C   CR16  0  -0.244  -6.1144   0.3877  -2.3989
 5WL  CAI  C   CR16  0  -0.409  -4.7503   0.4009  -2.0392
 5WL  H1   H   HCH3  0   0.303   3.1480  -4.9549  -1.8776
 5WL  H2   H   HCH3  0   0.314   2.2854  -6.2165  -0.9559
 5WL  H3   H   HCH3  0   0.301   1.4498  -4.6962  -1.3687
 5WL  H4   H   HNC1  0   0.446   4.1217  -2.5208  -0.0373
 5WL  H5   H   HNR5  0   0.420   4.2689  -0.5663   1.0266
 5WL  H6   H   HCR6  0   0.289   5.5104   1.9198   1.2365
 5WL  H7   H   HCR6  0   0.277   3.1220   4.9945  -0.5984
 5WL  H8   H   HCR6  0   0.259   1.4384   3.3469  -1.3036
 5WL  H9   H   HCH2  0   0.249   0.4009   1.2405  -2.1257
 5WL  H10  H   HCH2  0   0.254   0.3641  -0.4993  -1.9557
 5WL  H11  H   HCH2  0   0.247  -0.7071  -0.2526   0.2978
 5WL  H12  H   HCH2  0   0.241  -0.7055   1.4985   0.0997
 5WL  H13  H   HCH2  0   0.225  -2.1199   1.2662  -1.9514
 5WL  H14  H   HCH2  0   0.224  -2.1149  -0.4906  -1.7463
 5WL  H15  H   HCR6  0   0.253  -4.0216   0.8296   1.9649
 5WL  H16  H   HCR6  0   0.257  -5.7783   1.0458   3.6465
 5WL  H17  H   HCR6  0   0.258  -8.1684   1.0208   2.9801
 5WL  H18  H   HCR6  0   0.254  -8.7865   0.7734   0.6139
 5WL  H19  H   HCR6  0   0.250  -8.1417   0.4987  -1.7460
 5WL  H20  H   HCR6  0   0.259  -6.3713   0.2769  -3.4445
 5WL  H21  H   HCR6  0   0.281  -4.0093   0.3010  -2.8198

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
 5WL  CAA  SBE  single    1.770  0.020  1.770
 5WL  OAD  SBE  double    1.451  0.020  1.451
 5WL  OAC  SBE  double    1.448  0.020  1.448
 5WL  SBE  NAS  single    1.682  0.020  1.682
 5WL  NAS  CAV  single    1.379  0.020  1.379
 5WL  OAB  CAV  double    1.213  0.020  1.213
 5WL  CAV  CAZ  single    1.462  0.020  1.462
 5WL  CAZ  NAT  aromatic  1.379  0.020  1.379
 5WL  CAZ  CAY  aromatic  1.376  0.020  1.376
 5WL  NAT  CBB  aromatic  1.355  0.020  1.355
 5WL  CAR  CAY  single    1.492  0.020  1.492
 5WL  CAR  CAP  single    1.530  0.020  1.530
 5WL  CAY  CBD  aromatic  1.426  0.020  1.426
 5WL  CAP  CAQ  single    1.514  0.020  1.514
 5WL  CBB  CBD  aromatic  1.411  0.020  1.411
 5WL  CBB  CAO  aromatic  1.396  0.020  1.396
 5WL  CBD  CAN  aromatic  1.401  0.020  1.401
 5WL  CAQ  OAU  single    1.418  0.020  1.418
 5WL  CAO  CAW  aromatic  1.375  0.020  1.375
 5WL  OAU  CAX  single    1.342  0.020  1.342
 5WL  CAN  CAJ  aromatic  1.376  0.020  1.376
 5WL  CAW  CAJ  aromatic  1.407  0.020  1.407
 5WL  CAW  CL   single    1.735  0.020  1.735
 5WL  CAM  CAG  aromatic  1.370  0.020  1.370
 5WL  CAM  CBC  aromatic  1.414  0.020  1.414
 5WL  CAX  CBC  aromatic  1.429  0.020  1.429
 5WL  CAX  CAI  aromatic  1.374  0.020  1.374
 5WL  CAG  CAF  aromatic  1.408  0.020  1.408
 5WL  CBC  CBA  aromatic  1.419  0.020  1.419
 5WL  CAI  CAH  aromatic  1.411  0.020  1.411
 5WL  CAF  CAK  aromatic  1.368  0.020  1.368
 5WL  CBA  CAK  aromatic  1.414  0.020  1.414
 5WL  CBA  CAL  aromatic  1.416  0.020  1.416
 5WL  CAH  CAL  aromatic  1.365  0.020  1.365
 5WL  CAA  H1   single    0.970  0.020  1.090
 5WL  CAA  H2   single    0.970  0.020  1.090
 5WL  CAA  H3   single    0.970  0.020  1.090
 5WL  NAS  H4   single    0.860  0.020  1.020
 5WL  NAT  H5   single    0.860  0.020  1.020
 5WL  CAO  H6   single    0.930  0.020  1.080
 5WL  CAJ  H7   single    0.930  0.020  1.080
 5WL  CAN  H8   single    0.930  0.020  1.080
 5WL  CAR  H9   single    0.970  0.020  1.090
 5WL  CAR  H10  single    0.970  0.020  1.090
 5WL  CAP  H11  single    0.970  0.020  1.090
 5WL  CAP  H12  single    0.970  0.020  1.090
 5WL  CAQ  H13  single    0.970  0.020  1.090
 5WL  CAQ  H14  single    0.970  0.020  1.090
 5WL  CAM  H15  single    0.930  0.020  1.080
 5WL  CAG  H16  single    0.930  0.020  1.080
 5WL  CAF  H17  single    0.930  0.020  1.080
 5WL  CAK  H18  single    0.930  0.020  1.080
 5WL  CAL  H19  single    0.930  0.020  1.080
 5WL  CAH  H20  single    0.930  0.020  1.080
 5WL  CAI  H21  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
 5WL  H3   CAA  H2   110.12  3.000
 5WL  H3   CAA  H1   111.05  3.000
 5WL  H2   CAA  H1   110.18  3.000
 5WL  H3   CAA  SBE  109.41  3.000
 5WL  H2   CAA  SBE  107.04  3.000
 5WL  H1   CAA  SBE  108.94  3.000
 5WL  NAS  SBE  OAD  104.12  3.000
 5WL  NAS  SBE  OAC  108.22  3.000
 5WL  OAD  SBE  OAC  119.73  3.000
 5WL  NAS  SBE  CAA  104.72  3.000
 5WL  OAC  SBE  CAA  109.45  3.000
 5WL  OAD  SBE  CAA  109.47  3.000
 5WL  H4   NAS  CAV  120.99  3.000
 5WL  H4   NAS  SBE  115.08  3.000
 5WL  CAV  NAS  SBE  123.47  3.000
 5WL  CAZ  CAV  OAB  122.96  3.000
 5WL  CAZ  CAV  NAS  115.17  3.000
 5WL  OAB  CAV  NAS  121.87  3.000
 5WL  CAY  CAZ  NAT  109.87  3.000
 5WL  CAY  CAZ  CAV  127.28  3.000
 5WL  NAT  CAZ  CAV  122.84  3.000
 5WL  H5   NAT  CBB  124.39  3.000
 5WL  H5   NAT  CAZ  125.81  3.000
 5WL  CBB  NAT  CAZ  109.00  3.000
 5WL  CBD  CBB  CAO  122.50  3.000
 5WL  CAO  CBB  NAT  129.71  3.000
 5WL  CBD  CBB  NAT  107.79  3.000
 5WL  H6   CAO  CAW  121.92  3.000
 5WL  H6   CAO  CBB  121.86  3.000
 5WL  CAW  CAO  CBB  116.22  3.000
 5WL  CAJ  CAW  CL   118.15  3.000
 5WL  CL   CAW  CAO  118.87  3.000
 5WL  CAJ  CAW  CAO  122.98  3.000
 5WL  H7   CAJ  CAN  120.34  3.000
 5WL  H7   CAJ  CAW  119.68  3.000
 5WL  CAN  CAJ  CAW  119.98  3.000
 5WL  H8   CAN  CBD  121.06  3.000
 5WL  H8   CAN  CAJ  119.75  3.000
 5WL  CBD  CAN  CAJ  119.19  3.000
 5WL  CAY  CBD  CAN  133.34  3.000
 5WL  CAN  CBD  CBB  119.12  3.000
 5WL  CAY  CBD  CBB  107.54  3.000
 5WL  CAR  CAY  CBD  125.56  3.000
 5WL  CBD  CAY  CAZ  105.80  3.000
 5WL  CAR  CAY  CAZ  128.65  3.000
 5WL  H10  CAR  H9   106.33  3.000
 5WL  H10  CAR  CAP  109.44  3.000
 5WL  H9   CAR  CAP  109.39  3.000
 5WL  H10  CAR  CAY  110.17  3.000
 5WL  H9   CAR  CAY  108.99  3.000
 5WL  CAP  CAR  CAY  112.34  3.000
 5WL  H12  CAP  H11  107.52  3.000
 5WL  H12  CAP  CAQ  109.76  3.000
 5WL  H11  CAP  CAQ  109.71  3.000
 5WL  H12  CAP  CAR  109.87  3.000
 5WL  H11  CAP  CAR  109.29  3.000
 5WL  CAQ  CAP  CAR  110.63  3.000
 5WL  H14  CAQ  H13  107.53  3.000
 5WL  H14  CAQ  OAU  110.30  3.000
 5WL  H13  CAQ  OAU  110.28  3.000
 5WL  H14  CAQ  CAP  110.15  3.000
 5WL  H13  CAQ  CAP  110.57  3.000
 5WL  OAU  CAQ  CAP  108.03  3.000
 5WL  CAX  OAU  CAQ  119.33  3.000
 5WL  CAI  CAX  CBC  120.26  3.000
 5WL  CAI  CAX  OAU  124.64  3.000
 5WL  CBC  CAX  OAU  115.10  3.000
 5WL  CBA  CBC  CAM  119.14  3.000
 5WL  CBA  CBC  CAX  118.76  3.000
 5WL  CAM  CBC  CAX  122.09  3.000
 5WL  H15  CAM  CAG  119.48  3.000
 5WL  H15  CAM  CBC  119.94  3.000
 5WL  CAG  CAM  CBC  120.58  3.000
 5WL  H16  CAG  CAF  119.68  3.000
 5WL  H16  CAG  CAM  119.90  3.000
 5WL  CAF  CAG  CAM  120.41  3.000
 5WL  H17  CAF  CAK  120.13  3.000
 5WL  H17  CAF  CAG  119.76  3.000
 5WL  CAK  CAF  CAG  120.11  3.000
 5WL  H18  CAK  CBA  118.75  3.000
 5WL  H18  CAK  CAF  120.29  3.000
 5WL  CBA  CAK  CAF  120.96  3.000
 5WL  CAL  CBA  CAK  121.48  3.000
 5WL  CAL  CBA  CBC  119.73  3.000
 5WL  CAK  CBA  CBC  118.78  3.000
 5WL  H19  CAL  CAH  120.80  3.000
 5WL  H19  CAL  CBA  119.34  3.000
 5WL  CAH  CAL  CBA  119.86  3.000
 5WL  H20  CAH  CAI  118.48  3.000
 5WL  H20  CAH  CAL  120.19  3.000
 5WL  CAI  CAH  CAL  121.34  3.000
 5WL  H21  CAI  CAH  118.54  3.000
 5WL  H21  CAI  CAX  121.41  3.000
 5WL  CAH  CAI  CAX  120.05  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
 5WL  CONST_01  CBD  CBB  NAT  CAZ     0.00   0.0  0
 5WL  CONST_02  CAO  CBB  NAT  CAZ   180.00   0.0  0
 5WL  CONST_03  CBB  CBD  CAY  CAZ     0.00   0.0  0
 5WL  CONST_04  CAN  CBD  CAY  CAZ   180.00   0.0  0
 5WL  CONST_05  CBD  CAY  CAZ  NAT     0.00   0.0  0
 5WL  CONST_06  CAY  CBD  CBB  NAT     0.00   0.0  0
 5WL  CONST_07  CAN  CBD  CBB  NAT   180.00   0.0  0
 5WL  CONST_08  CAW  CAO  CBB  NAT   180.00   0.0  0
 5WL  CONST_09  CAY  CAZ  NAT  CBB     0.00   0.0  0
 5WL  CONST_10  CAJ  CAN  CBD  CBB     0.00   0.0  0
 5WL  CONST_11  CAJ  CAW  CAO  CBB     0.00   0.0  0
 5WL  CONST_12  CAY  CBD  CBB  CAO   180.00   0.0  0
 5WL  CONST_13  CAN  CBD  CBB  CAO     0.00   0.0  0
 5WL  CONST_14  CAN  CAJ  CAW  CAO     0.00   0.0  0
 5WL  CONST_15  CBD  CBB  CAO  CAW     0.00   0.0  0
 5WL  CONST_16  CBD  CAN  CAJ  CAW     0.00   0.0  0
 5WL  CONST_17  CAY  CBD  CAN  CAJ   180.00   0.0  0
 5WL  CONST_18  CAG  CAM  CBC  CAX   180.00   0.0  0
 5WL  CONST_19  CAK  CBA  CBC  CAX   180.00   0.0  0
 5WL  CONST_20  CAL  CBA  CBC  CAX     0.00   0.0  0
 5WL  CONST_21  CAL  CAH  CAI  CAX     0.00   0.0  0
 5WL  CONST_22  CAF  CAG  CAM  CBC     0.00   0.0  0
 5WL  CONST_23  CAH  CAI  CAX  CBC     0.00   0.0  0
 5WL  CONST_24  CAF  CAK  CBA  CBC     0.00   0.0  0
 5WL  CONST_25  CAH  CAL  CBA  CBC     0.00   0.0  0
 5WL  CONST_26  CAK  CAF  CAG  CAM     0.00   0.0  0
 5WL  CONST_27  CAI  CAX  CBC  CAM   180.00   0.0  0
 5WL  CONST_28  CAK  CBA  CBC  CAM     0.00   0.0  0
 5WL  CONST_29  CAL  CBA  CBC  CAM   180.00   0.0  0
 5WL  CONST_30  CBA  CBC  CAM  CAG     0.00   0.0  0
 5WL  CONST_31  CBA  CAK  CAF  CAG     0.00   0.0  0
 5WL  CONST_32  CAL  CBA  CAK  CAF   180.00   0.0  0
 5WL  CONST_33  CAH  CAL  CBA  CAK   180.00   0.0  0
 5WL  CONST_34  CAI  CAX  CBC  CBA     0.00   0.0  0
 5WL  CONST_35  CAI  CAH  CAL  CBA     0.00   0.0  0
 5WL  CONST_36  CBB  NAT  CAZ  CAV   180.00   0.0  0
 5WL  CONST_37  CBD  CAY  CAZ  CAV   180.00   0.0  0
 5WL  CONST_38  CAR  CAY  CAZ  NAT   180.00   0.0  0
 5WL  CONST_39  CAR  CAY  CBD  CBB   180.00   0.0  0
 5WL  CONST_40  CL   CAW  CAO  CBB   180.00   0.0  0
 5WL  CONST_41  CAN  CAJ  CAW  CL    180.00   0.0  0
 5WL  CONST_42  CAR  CAY  CBD  CAN     0.00   0.0  0
 5WL  CONST_43  CAM  CBC  CAX  OAU     0.00   0.0  0
 5WL  CONST_44  CBA  CBC  CAX  OAU   180.00   0.0  0
 5WL  CONST_45  CAH  CAI  CAX  OAU   180.00   0.0  0
 5WL  CONST_46  H6   CAO  CBB  NAT     0.00   0.0  0
 5WL  CONST_47  H8   CAN  CBD  CBB   180.00   0.0  0
 5WL  CONST_48  H5   NAT  CBB  CAO     0.00   0.0  0
 5WL  CONST_49  H7   CAJ  CAW  CAO   180.00   0.0  0
 5WL  CONST_50  H15  CAM  CBC  CAX     0.00   0.0  0
 5WL  CONST_51  H20  CAH  CAI  CAX   180.00   0.0  0
 5WL  CONST_52  H16  CAG  CAM  CBC   180.00   0.0  0
 5WL  CONST_53  H21  CAI  CAX  CBC   180.00   0.0  0
 5WL  CONST_54  H18  CAK  CBA  CBC   180.00   0.0  0
 5WL  CONST_55  H19  CAL  CBA  CBC   180.00   0.0  0
 5WL  CONST_56  H17  CAF  CAG  CAM   180.00   0.0  0
 5WL  CONST_57  CAZ  CAV  NAS  SBE   180.00   0.0  0
 5WL  CONST_59  OAB  CAV  NAS  SBE     0.00   0.0  0
 5WL  Var_01    NAT  CAZ  CAV  NAS   -20.43  30.0  2
 5WL  Var_02    CAP  CAR  CAY  CAZ    87.77  30.0  2
 5WL  Var_03    CBC  CAX  OAU  CAQ  -179.23  30.0  2
 5WL  Var_04    CAQ  CAP  CAR  CAY  -179.14  30.0  3
 5WL  Var_05    H13  CAQ  OAU  CAX    57.98  30.0  1
 5WL  Var_06    CAV  NAS  SBE  CAA    70.41  30.0  3
 5WL  Var_07    OAU  CAQ  CAP  CAR   179.60  30.0  3
 5WL  Var_08    H1   CAA  SBE  OAC   175.64  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
 5WL  plan-1  CAV  0.020
 5WL  plan-1  CAZ  0.020
 5WL  plan-1  NAT  0.020
 5WL  plan-1  CBB  0.020
 5WL  plan-1  CAO  0.020
 5WL  plan-1  CAW  0.020
 5WL  plan-1  CL   0.020
 5WL  plan-1  CAJ  0.020
 5WL  plan-1  CAN  0.020
 5WL  plan-1  CBD  0.020
 5WL  plan-1  CAY  0.020
 5WL  plan-1  CAR  0.020
 5WL  plan-1  H5   0.020
 5WL  plan-1  H6   0.020
 5WL  plan-1  H7   0.020
 5WL  plan-1  H8   0.020
 5WL  plan-2  OAU  0.020
 5WL  plan-2  CAX  0.020
 5WL  plan-2  CBC  0.020
 5WL  plan-2  CAM  0.020
 5WL  plan-2  CAG  0.020
 5WL  plan-2  CAF  0.020
 5WL  plan-2  CAK  0.020
 5WL  plan-2  CBA  0.020
 5WL  plan-2  CAL  0.020
 5WL  plan-2  CAH  0.020
 5WL  plan-2  CAI  0.020
 5WL  plan-2  H15  0.020
 5WL  plan-2  H16  0.020
 5WL  plan-2  H17  0.020
 5WL  plan-2  H18  0.020
 5WL  plan-2  H19  0.020
 5WL  plan-2  H20  0.020
 5WL  plan-2  H21  0.020
 5WL  plan-3  SBE  0.020
 5WL  plan-3  NAS  0.020
 5WL  plan-3  CAV  0.020
 5WL  plan-3  OAB  0.020
 5WL  plan-3  CAZ  0.020
 5WL  plan-3  H4   0.020

