# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Sat May  9 02:01:17 2020
#   Inital geometry file: a 144 line input string
#   Ligand name: tert-butyl 6-{[2-chloro-4-(dimethylcarbamoyl)phenyl]amino}-2-(1,3-oxazol-5-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CN(C)C(=O)c1ccc(Nc2cc3n(C(=O)OC(C)(C)C)c(cc3cn2)c4ocnc4)c(Cl)c1
#
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
 X20  X20  'tert-butyl 6-{[2-chloro-4-(dimethylcarbamoyl)phenyl]amino}-2-(1,3-oxazol-5-yl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylate'  ligand  58  34  .  2021-08-24  2021-08-24  
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_X20
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
 X20  C     C   C     0   0.785  -3.5187   1.1211   0.1709
 X20  N     N   NR5   0  -0.706  -2.9760  -0.1687   0.1657
 X20  O     O   O     0  -0.454  -2.8812   2.0724  -0.1959
 X20  CL    CL  CL    0  -0.117   3.5312   3.0007  -0.0694
 X20  C1    C   CR56  0   0.490  -1.6155  -0.4231   0.2070
 X20  N1    N   NH1   0  -0.791   1.8469   0.5938   0.1182
 X20  O1    O   O     0  -0.494   8.0419   0.3179  -1.1124
 X20  C2    C   CR16  0  -0.497  -0.5143   0.4054   0.1096
 X20  N2    N   NT    0  -0.444   8.0796  -1.2467   0.5155
 X20  O2    O   O     0  -0.392  -5.7369  -1.0693  -0.8944
 X20  C3    C   CR6   0   0.575   0.7354  -0.2187   0.2124
 X20  N3    N   N     0  -0.477   0.8991  -1.5282   0.3954
 X20  O3    O   O2    0  -0.477  -4.7374   1.1037   0.6398
 X20  C4    C   CR6   0   0.448   3.1888   0.2990   0.0705
 X20  N4    N   N     0  -0.409  -7.2258  -2.1489   0.3127
 X20  C5    C   CR16  0  -0.319   3.7314  -0.9930   0.0983
 X20  C6    C   CR16  0  -0.241   5.0977  -1.1971   0.0411
 X20  C7    C   CR6   0  -0.091   5.9896  -0.1354  -0.0577
 X20  C8    C   C     0   0.514   7.4568  -0.3273  -0.2488
 X20  C9    C   CH3   0  -0.525   9.4515  -1.6055   0.2201
 X20  C10   C   CH3   0  -0.535   7.5822  -1.7462   1.7825
 X20  C11   C   CR16  0  -0.226   5.4701   1.1529  -0.1136
 X20  C12   C   CR6   0  -0.156   4.1098   1.3611  -0.0298
 X20  C13   C   CR16  0  -0.094  -0.1652  -2.3059   0.4911
 X20  C14   C   CR56  0  -0.047  -1.4545  -1.8075   0.4082
 X20  C15   C   CR15  0  -0.417  -2.7562  -2.3935   0.4546
 X20  C16   C   CR5   0   0.307  -3.6579  -1.3949   0.3061
 X20  C17   C   CR5   0   0.292  -5.0890  -1.5587   0.1937
 X20  C18   C   CR15  0  -0.218  -6.0003  -2.2257   0.9362
 X20  C19   C   CR15  0   0.156  -7.0072  -1.4579  -0.7489
 X20  C20   C   CT    0   0.174  -5.6088   2.2849   0.6485
 X20  C21   C   CH3   0  -0.674  -5.8581   2.7596  -0.7752
 X20  C22   C   CH3   0  -0.660  -6.8963   1.7508   1.2587
 X20  C23   C   CH3   0  -0.670  -5.0242   3.3770   1.5324
 X20  HN1   H   HNH1  0   0.408   1.6248   1.5734   0.0253
 X20  H2    H   HCR6  0   0.296  -0.5885   1.4698  -0.0497
 X20  H5    H   HCR6  0   0.302   3.0692  -1.8390   0.1634
 X20  H6    H   HCR6  0   0.271   5.4611  -2.2170   0.0550
 X20  H9    H   HCH3  0   0.239  10.1598  -1.0031   0.7943
 X20  H9A   H   HCH3  0   0.246   9.6051  -2.6520   0.4816
 X20  H9B   H   HCH3  0   0.254   9.6657  -1.4819  -0.8373
 X20  H10   H   HCH3  0   0.245   7.3390  -2.8088   1.7285
 X20  H10A  H   HCH3  0   0.255   8.3518  -1.6130   2.5447
 X20  H10B  H   HCH3  0   0.263   6.7019  -1.2018   2.1082
 X20  H11   H   HCR6  0   0.280   6.1303   2.0045  -0.2102
 X20  H13   H   HCR6  0   0.271   0.0153  -3.3647   0.6402
 X20  H15   H   HCR5  0   0.277  -2.9942  -3.4424   0.5314
 X20  H18   H   HCR5  0   0.280  -5.8532  -2.7398   1.8722
 X20  H19   H   HCR5  0   0.301  -7.7095  -1.1649  -1.5143
 X20  H21   H   HCH3  0   0.240  -6.2454   1.9487  -1.3937
 X20  H21A  H   HCH3  0   0.246  -6.6094   3.5492  -0.7573
 X20  H21B  H   HCH3  0   0.251  -4.9659   3.1664  -1.2464
 X20  H22   H   HCH3  0   0.244  -6.7329   1.3659   2.2658
 X20  H22A  H   HCH3  0   0.240  -7.6310   2.5529   1.3202
 X20  H22B  H   HCH3  0   0.242  -7.3257   0.9558   0.6488
 X20  H23   H   HCH3  0   0.251  -4.1284   3.8267   1.1107
 X20  H23A  H   HCH3  0   0.242  -5.7679   4.1663   1.6465
 X20  H23B  H   HCH3  0   0.243  -4.7932   2.9953   2.5277

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
 X20  C    N     single    1.399  0.020  1.399
 X20  C    O     double    1.202  0.020  1.202
 X20  C    O3    single    1.306  0.020  1.306
 X20  N    C1    aromatic  1.385  0.020  1.385
 X20  N    C16   aromatic  1.410  0.020  1.410
 X20  CL   C12   single    1.739  0.020  1.739
 X20  C1   C2    aromatic  1.381  0.020  1.381
 X20  C1   C14   aromatic  1.408  0.020  1.408
 X20  N1   C3    single    1.380  0.020  1.380
 X20  N1   C4    single    1.375  0.020  1.375
 X20  O1   C8    double    1.226  0.020  1.226
 X20  C2   C3    aromatic  1.401  0.020  1.401
 X20  N2   C8    single    1.348  0.020  1.348
 X20  N2   C9    single    1.448  0.020  1.448
 X20  N2   C10   single    1.450  0.020  1.450
 X20  O2   C17   aromatic  1.358  0.020  1.358
 X20  O2   C19   aromatic  1.336  0.020  1.336
 X20  C3   N3    aromatic  1.332  0.020  1.332
 X20  N3   C13   aromatic  1.322  0.020  1.322
 X20  O3   C20   single    1.468  0.020  1.468
 X20  C4   C5    aromatic  1.402  0.020  1.402
 X20  C4   C12   aromatic  1.409  0.020  1.409
 X20  N4   C18   aromatic  1.377  0.020  1.377
 X20  N4   C19   aromatic  1.285  0.020  1.285
 X20  C5   C6    aromatic  1.383  0.020  1.383
 X20  C6   C7    aromatic  1.390  0.020  1.390
 X20  C7   C8    single    1.492  0.020  1.492
 X20  C7   C11   aromatic  1.390  0.020  1.390
 X20  C11  C12   aromatic  1.379  0.020  1.379
 X20  C13  C14   aromatic  1.385  0.020  1.385
 X20  C14  C15   aromatic  1.428  0.020  1.428
 X20  C15  C16   aromatic  1.354  0.020  1.354
 X20  C16  C17   single    1.445  0.020  1.445
 X20  C17  C18   aromatic  1.352  0.020  1.352
 X20  C20  C21   single    1.521  0.020  1.521
 X20  C20  C22   single    1.522  0.020  1.522
 X20  C20  C23   single    1.522  0.020  1.522
 X20  N1   HN1   single    0.860  0.020  1.020
 X20  C2   H2    single    0.930  0.020  1.080
 X20  C5   H5    single    0.930  0.020  1.080
 X20  C6   H6    single    0.930  0.020  1.080
 X20  C9   H9    single    0.970  0.020  1.090
 X20  C9   H9A   single    0.970  0.020  1.090
 X20  C9   H9B   single    0.970  0.020  1.090
 X20  C10  H10   single    0.970  0.020  1.090
 X20  C10  H10A  single    0.970  0.020  1.090
 X20  C10  H10B  single    0.970  0.020  1.090
 X20  C11  H11   single    0.930  0.020  1.080
 X20  C13  H13   single    0.930  0.020  1.080
 X20  C15  H15   single    0.930  0.020  1.080
 X20  C18  H18   single    0.930  0.020  1.080
 X20  C19  H19   single    0.930  0.020  1.080
 X20  C21  H21   single    0.970  0.020  1.090
 X20  C21  H21A  single    0.970  0.020  1.090
 X20  C21  H21B  single    0.970  0.020  1.090
 X20  C22  H22   single    0.970  0.020  1.090
 X20  C22  H22A  single    0.970  0.020  1.090
 X20  C22  H22B  single    0.970  0.020  1.090
 X20  C23  H23   single    0.970  0.020  1.090
 X20  C23  H23A  single    0.970  0.020  1.090
 X20  C23  H23B  single    0.970  0.020  1.090

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
 X20  O3    C    O     127.94  3.000
 X20  O3    C    N     110.55  3.000
 X20  O     C    N     121.50  3.000
 X20  C16   N    C1    108.21  3.000
 X20  C16   N    C     127.85  3.000
 X20  C1    N    C     123.39  3.000
 X20  C14   C1   C2    120.57  3.000
 X20  C14   C1   N     107.29  3.000
 X20  C2    C1   N     132.13  3.000
 X20  HN1   N1   C4    114.83  3.000
 X20  HN1   N1   C3    113.63  3.000
 X20  C4    N1   C3    131.47  3.000
 X20  H2    C2   C3    120.79  3.000
 X20  H2    C2   C1    123.18  3.000
 X20  C3    C2   C1    116.03  3.000
 X20  C10   N2   C9    114.70  3.000
 X20  C10   N2   C8    124.88  3.000
 X20  C9    N2   C8    119.40  3.000
 X20  C19   O2   C17   105.16  3.000
 X20  N3    C3   C2    123.89  3.000
 X20  N3    C3   N1    119.28  3.000
 X20  C2    C3   N1    116.82  3.000
 X20  C13   N3   C3    119.30  3.000
 X20  C20   O3   C     123.05  3.000
 X20  C12   C4   C5    116.30  3.000
 X20  C12   C4   N1    118.60  3.000
 X20  C5    C4   N1    125.09  3.000
 X20  C19   N4   C18   104.63  3.000
 X20  H5    C5   C6    119.63  3.000
 X20  H5    C5   C4    119.18  3.000
 X20  C6    C5   C4    121.19  3.000
 X20  H6    C6   C7    120.33  3.000
 X20  H6    C6   C5    118.05  3.000
 X20  C7    C6   C5    121.61  3.000
 X20  C11   C7   C8    118.78  3.000
 X20  C11   C7   C6    118.09  3.000
 X20  C8    C7   C6    122.81  3.000
 X20  C7    C8   N2    117.99  3.000
 X20  C7    C8   O1    119.45  3.000
 X20  N2    C8   O1    122.52  3.000
 X20  H9B   C9   H9A   108.38  3.000
 X20  H9B   C9   H9    108.72  3.000
 X20  H9A   C9   H9    108.18  3.000
 X20  H9B   C9   N2    110.93  3.000
 X20  H9A   C9   N2    108.82  3.000
 X20  H9    C9   N2    111.72  3.000
 X20  H10B  C10  H10A  107.53  3.000
 X20  H10B  C10  H10   108.81  3.000
 X20  H10A  C10  H10   108.09  3.000
 X20  H10B  C10  N2    111.58  3.000
 X20  H10A  C10  N2    109.05  3.000
 X20  H10   C10  N2    111.64  3.000
 X20  H11   C11  C12   119.25  3.000
 X20  H11   C11  C7    120.33  3.000
 X20  C12   C11  C7    120.41  3.000
 X20  C11   C12  C4    122.36  3.000
 X20  C11   C12  CL    117.98  3.000
 X20  C4    C12  CL    119.65  3.000
 X20  H13   C13  C14   120.97  3.000
 X20  H13   C13  N3    116.77  3.000
 X20  C14   C13  N3    122.25  3.000
 X20  C15   C14  C13   134.34  3.000
 X20  C15   C14  C1    107.69  3.000
 X20  C13   C14  C1    117.96  3.000
 X20  H15   C15  C16   125.34  3.000
 X20  H15   C15  C14   127.05  3.000
 X20  C16   C15  C14   107.51  3.000
 X20  C17   C16  C15   125.78  3.000
 X20  C17   C16  N     124.74  3.000
 X20  C15   C16  N     109.28  3.000
 X20  C18   C17  C16   132.93  3.000
 X20  C18   C17  O2    107.24  3.000
 X20  C16   C17  O2    119.62  3.000
 X20  H18   C18  C17   128.35  3.000
 X20  H18   C18  N4    122.76  3.000
 X20  C17   C18  N4    108.89  3.000
 X20  H19   C19  N4    128.38  3.000
 X20  H19   C19  O2    117.54  3.000
 X20  N4    C19  O2    114.07  3.000
 X20  C23   C20  C22   110.13  3.000
 X20  C23   C20  C21   112.50  3.000
 X20  C22   C20  C21   110.25  3.000
 X20  C23   C20  O3    110.66  3.000
 X20  C22   C20  O3    102.84  3.000
 X20  C21   C20  O3    110.05  3.000
 X20  H21B  C21  H21A  107.55  3.000
 X20  H21B  C21  H21   108.88  3.000
 X20  H21A  C21  H21   107.64  3.000
 X20  H21B  C21  C20   112.81  3.000
 X20  H21A  C21  C20   108.88  3.000
 X20  H21   C21  C20   110.90  3.000
 X20  H22B  C22  H22A  107.63  3.000
 X20  H22B  C22  H22   108.56  3.000
 X20  H22A  C22  H22   107.98  3.000
 X20  H22B  C22  C20   111.41  3.000
 X20  H22A  C22  C20   109.56  3.000
 X20  H22   C22  C20   111.56  3.000
 X20  H23B  C23  H23A  107.59  3.000
 X20  H23B  C23  H23   108.92  3.000
 X20  H23A  C23  H23   107.64  3.000
 X20  H23B  C23  C20   111.11  3.000
 X20  H23A  C23  C20   108.56  3.000
 X20  H23   C23  C20   112.83  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
 X20  CONST_01  C3   C2   C1   N     180.00   0.0  0
 X20  CONST_02  C13  C14  C1   N     180.00   0.0  0
 X20  CONST_03  C15  C14  C1   N       0.00   0.0  0
 X20  CONST_04  C14  C15  C16  N       0.00   0.0  0
 X20  CONST_07  C15  C16  N    C1      0.00   0.0  0
 X20  CONST_08  C17  C16  N    C1    180.00   0.0  0
 X20  CONST_09  N3   C3   C2   C1      0.00   0.0  0
 X20  CONST_10  N3   C13  C14  C1      0.00   0.0  0
 X20  CONST_11  C16  C15  C14  C1      0.00   0.0  0
 X20  CONST_12  C16  N    C1   C2    180.00   0.0  0
 X20  CONST_13  C13  C14  C1   C2      0.00   0.0  0
 X20  CONST_14  C15  C14  C1   C2    180.00   0.0  0
 X20  CONST_15  C13  N3   C3   C2      0.00   0.0  0
 X20  CONST_17  N4   C18  C17  O2      0.00   0.0  0
 X20  CONST_18  C18  N4   C19  O2      0.00   0.0  0
 X20  CONST_19  C14  C1   C2   C3      0.00   0.0  0
 X20  CONST_20  C14  C13  N3   C3      0.00   0.0  0
 X20  CONST_21  C15  C14  C13  N3    180.00   0.0  0
 X20  CONST_22  C7   C6   C5   C4      0.00   0.0  0
 X20  CONST_23  C7   C11  C12  C4      0.00   0.0  0
 X20  CONST_24  C16  C17  C18  N4    180.00   0.0  0
 X20  CONST_25  C17  O2   C19  N4      0.00   0.0  0
 X20  CONST_26  C11  C12  C4   C5      0.00   0.0  0
 X20  CONST_27  C11  C7   C6   C5      0.00   0.0  0
 X20  CONST_28  C12  C4   C5   C6      0.00   0.0  0
 X20  CONST_29  C12  C11  C7   C6      0.00   0.0  0
 X20  CONST_30  C16  C15  C14  C13   180.00   0.0  0
 X20  CONST_31  C16  N    C1   C14     0.00   0.0  0
 X20  CONST_32  C17  C16  C15  C14   180.00   0.0  0
 X20  CONST_34  C19  O2   C17  C16   180.00   0.0  0
 X20  CONST_35  C19  N4   C18  C17     0.00   0.0  0
 X20  CONST_36  C19  O2   C17  C18     0.00   0.0  0
 X20  CONST_37  C2   C1   N    C       0.00   0.0  0
 X20  CONST_38  C14  C1   N    C     180.00   0.0  0
 X20  CONST_39  C15  C16  N    C     180.00   0.0  0
 X20  CONST_40  C17  C16  N    C       0.00   0.0  0
 X20  CONST_41  C5   C4   C12  CL    180.00   0.0  0
 X20  CONST_42  C7   C11  C12  CL    180.00   0.0  0
 X20  CONST_43  N1   C3   C2   C1    180.00   0.0  0
 X20  CONST_44  C13  N3   C3   N1    180.00   0.0  0
 X20  CONST_45  C6   C5   C4   N1    180.00   0.0  0
 X20  CONST_46  C11  C12  C4   N1    180.00   0.0  0
 X20  CONST_47  C8   C7   C6   C5    180.00   0.0  0
 X20  CONST_48  C12  C11  C7   C8    180.00   0.0  0
 X20  CONST_49  H2   C2   C1   N       0.00   0.0  0
 X20  CONST_50  H15  C15  C16  N     180.00   0.0  0
 X20  CONST_51  H13  C13  C14  C1    180.00   0.0  0
 X20  CONST_52  H18  C18  C17  O2    180.00   0.0  0
 X20  CONST_53  H6   C6   C5   C4    180.00   0.0  0
 X20  CONST_54  H11  C11  C12  C4    180.00   0.0  0
 X20  CONST_55  H5   C5   C6   C7    180.00   0.0  0
 X20  CONST_56  H19  C19  O2   C17   180.00   0.0  0
 X20  CONST_57  C9   N2   C8   C7    180.00   0.0  0
 X20  CONST_59  C9   N2   C8   O1      0.00   0.0  0
 X20  Var_01    C4   N1   C3   C2   -174.09  30.0  1
 X20  Var_02    C5   C4   N1   C3      0.68  30.0  2
 X20  Var_03    C1   N    C    O      23.28  30.0  2
 X20  Var_04    C6   C7   C8   O1    132.18  30.0  3
 X20  Var_05    C21  C20  O3   C      61.62  30.0  3
 X20  Var_06    H21  C21  C20  O3     54.22  30.0  3
 X20  Var_07    H22  C22  C20  O3     60.31  30.0  3
 X20  Var_08    H23  C23  C20  O3     69.97  30.0  3
 X20  Var_09    H9   C9   N2   C8     92.81  30.0  3
 X20  Var_10    H10  C10  N2   C8    114.99  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
 X20  plan-1  O2   0.020
 X20  plan-1  N4   0.020
 X20  plan-1  C16  0.020
 X20  plan-1  C17  0.020
 X20  plan-1  C18  0.020
 X20  plan-1  C19  0.020
 X20  plan-1  H18  0.020
 X20  plan-1  H19  0.020
 X20  plan-2  CL   0.020
 X20  plan-2  N1   0.020
 X20  plan-2  C4   0.020
 X20  plan-2  C5   0.020
 X20  plan-2  C6   0.020
 X20  plan-2  C7   0.020
 X20  plan-2  C8   0.020
 X20  plan-2  C11  0.020
 X20  plan-2  C12  0.020
 X20  plan-2  H5   0.020
 X20  plan-2  H6   0.020
 X20  plan-2  H11  0.020
 X20  plan-3  C    0.020
 X20  plan-3  N    0.020
 X20  plan-3  C1   0.020
 X20  plan-3  N1   0.020
 X20  plan-3  C2   0.020
 X20  plan-3  C3   0.020
 X20  plan-3  N3   0.020
 X20  plan-3  C13  0.020
 X20  plan-3  C14  0.020
 X20  plan-3  C15  0.020
 X20  plan-3  C16  0.020
 X20  plan-3  C17  0.020
 X20  plan-3  H2   0.020
 X20  plan-3  H13  0.020
 X20  plan-3  H15  0.020
 X20  plan-4  O1   0.020
 X20  plan-4  N2   0.020
 X20  plan-4  C7   0.020
 X20  plan-4  C8   0.020
 X20  plan-4  C9   0.020
 X20  plan-4  C10  0.020
 X20  plan-5  C    0.020
 X20  plan-5  N    0.020
 X20  plan-5  O    0.020
 X20  plan-5  O3   0.020

