# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Fri Mar 11 07:27:11 2022
#   Inital geometry file: a 129 line input string
#   Ligand name: 2-{[(2S)-2-hydroxy-3-{[1-(1H-indol-3-yl)-2-methylpropan-2-yl]amino}propyl]oxy}benzonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: CC(C)(Cc1c[nH]c2ccccc12)NC[C@H](O)COc3ccccc3C#N
#
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
 G90  G90  2-{[(2S)-2-hydroxy-3-{[1-(1H-indol-3-yl)-2-methylpropan-2-yl]amino}propyl]oxy}benzonitrile  ligand  52  27  .  2022-03-18  2022-03-18
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as PERFECT
;

data_comp_G90
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
 G90  N1    N  NS    0  -0.256  -6.0615  -2.0597   2.2966
 G90  C12   C  CSP   0   0.066  -6.2217  -1.1934   1.5530
 G90  C7    C  CR6   0  -0.114  -6.4451  -0.1286   0.6359
 G90  C6    C  CR6   0   0.432  -5.3574   0.3856  -0.0900
 G90  C11   C  CR16  0  -0.380  -5.5816   1.4282  -0.9850
 G90  C10   C  CR16  0  -0.222  -6.8629   1.9375  -1.1409
 G90  C9    C  CR16  0  -0.277  -7.9386   1.4305  -0.4227
 G90  C8    C  CR16  0  -0.228  -7.7262   0.3942   0.4679
 G90  O2    O  O2    0  -0.453  -4.1766  -0.1838   0.1483
 G90  C5    C  CH2   0  -0.194  -3.0214   0.3090  -0.5147
 G90  C4    C  CH1   0  -0.027  -1.8295  -0.4999  -0.0317
 G90  O1    O  OH1   0  -0.653  -1.9841  -1.8706  -0.2999
 G90  C3    C  CH2   0  -0.291  -0.5469   0.0854  -0.6164
 G90  N     N  NH1   0  -0.604   0.6087  -0.5961  -0.0762
 G90  CA    C  CT    0   0.108   1.9273  -0.1781  -0.5644
 G90  C1    C  CH3   0  -0.663   2.0193  -0.4272  -2.0669
 G90  C2    C  CH3   0  -0.658   2.2288   1.2937  -0.2680
 G90  CB    C  CH2   0  -0.527   2.9274  -1.0970   0.1760
 G90  CG    C  CR5   0   0.011   4.3763  -0.8791  -0.1167
 G90  CD2   C  CR56  0   0.021   5.2921  -0.0230   0.5822
 G90  CE3   C  CR16  0  -0.370   5.1743   0.8307   1.6858
 G90  CZ3   C  CR16  0  -0.270   6.2869   1.5218   2.1239
 G90  CH2   C  CR16  0  -0.287   7.5277   1.3810   1.4794
 G90  CZ2   C  CR16  0  -0.307   7.6785   0.5423   0.3922
 G90  CE2   C  CR56  0   0.349   6.5526  -0.1556  -0.0437
 G90  NE1   N  NR15  0  -0.687   6.4059  -1.0466  -1.0646
 G90  CD1   C  CR15  0  -0.080   5.1107  -1.4808  -1.1016
 G90  H8    H  HCR6  0   0.283  -8.5459  -0.0169   1.0415
 G90  H11   H  HCR6  0   0.297  -4.7724   1.8516  -1.5629
 G90  H10   H  HCR6  0   0.277  -7.0166   2.7495  -1.8393
 G90  H9    H  HCR6  0   0.270  -8.9301   1.8398  -0.5544
 G90  H51C  H  HCH2  0   0.235  -3.1364   0.2141  -1.6013
 G90  H52C  H  HCH2  0   0.239  -2.8741   1.3682  -0.2813
 G90  H4    H  HCH1  0   0.235  -1.7835  -0.4106   1.0602
 G90  H1    H  HOH1  0   0.443  -1.8378  -2.0169  -1.2408
 G90  H31C  H  HCH2  0   0.230  -0.5682  -0.0375  -1.7039
 G90  H32C  H  HCH2  0   0.206  -0.5495   1.1704  -0.4338
 G90  H     H  HNH1  0   0.334   0.5952  -0.4897   0.9332
 G90  H11C  H  HCH3  0   0.229   1.3601   0.2323  -2.6326
 G90  H12C  H  HCH3  0   0.235   3.0341  -0.2415  -2.4189
 G90  H13C  H  HCH3  0   0.224   1.7563  -1.4588  -2.3091
 G90  H21C  H  HCH3  0   0.217   2.1745   1.4954   0.8044
 G90  H22C  H  HCH3  0   0.232   3.2260   1.5715  -0.6101
 G90  H23C  H  HCH3  0   0.229   1.5175   1.9537  -0.7679
 G90  HB1C  H  HCH2  0   0.232   2.7609  -0.9837   1.2540
 G90  HB2C  H  HCH2  0   0.241   2.6567  -2.1287  -0.0646
 G90  HD1   H  HCR5  0   0.279   4.7994  -2.2057  -1.8379
 G90  HE3   H  HCR6  0   0.235   4.2243   0.9488   2.1926
 G90  HZ3   H  HCR6  0   0.244   6.2065   2.1836   2.9767
 G90  HH2   H  HCR6  0   0.247   8.3809   1.9400   1.8419
 G90  HZ2   H  HCR6  0   0.256   8.6360   0.4299  -0.1010
 G90  HE1   H  HNR5  0   0.407   7.1349  -1.3539  -1.6863

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
 G90  N1   C12   triple    1.153  0.020  1.153
 G90  C12  C7    single    1.423  0.020  1.423
 G90  C7   C6    aromatic  1.405  0.020  1.405
 G90  C7   C8    aromatic  1.394  0.020  1.394
 G90  C6   C11   aromatic  1.392  0.020  1.392
 G90  C6   O2    single    1.332  0.020  1.332
 G90  C11  C10   aromatic  1.388  0.020  1.388
 G90  C10  C9    aromatic  1.389  0.020  1.389
 G90  C9   C8    aromatic  1.383  0.020  1.383
 G90  O2   C5    single    1.420  0.020  1.420
 G90  C5   C4    single    1.519  0.020  1.519
 G90  C4   O1    single    1.405  0.020  1.405
 G90  C4   C3    single    1.526  0.020  1.526
 G90  C3   N     single    1.446  0.020  1.446
 G90  N    CA    single    1.467  0.020  1.467
 G90  CA   C1    single    1.526  0.020  1.526
 G90  CA   C2    single    1.531  0.020  1.531
 G90  CA   CB    single    1.547  0.020  1.547
 G90  CB   CG    single    1.494  0.020  1.494
 G90  CG   CD2   aromatic  1.435  0.020  1.435
 G90  CG   CD1   aromatic  1.368  0.020  1.368
 G90  CD2  CE3   aromatic  1.400  0.020  1.400
 G90  CD2  CE2   aromatic  1.414  0.020  1.414
 G90  CE3  CZ3   aromatic  1.381  0.020  1.381
 G90  CZ3  CH2   aromatic  1.405  0.020  1.405
 G90  CH2  CZ2   aromatic  1.381  0.020  1.381
 G90  CZ2  CE2   aromatic  1.395  0.020  1.395
 G90  CE2  NE1   aromatic  1.363  0.020  1.363
 G90  NE1  CD1   aromatic  1.367  0.020  1.367
 G90  C8   H8    single    0.930  0.020  1.080
 G90  C11  H11   single    0.930  0.020  1.080
 G90  C10  H10   single    0.930  0.020  1.080
 G90  C9   H9    single    0.930  0.020  1.080
 G90  C5   H51C  single    0.970  0.020  1.090
 G90  C5   H52C  single    0.970  0.020  1.090
 G90  C4   H4    single    0.970  0.020  1.090
 G90  O1   H1    single    0.850  0.020  0.980
 G90  C3   H31C  single    0.970  0.020  1.090
 G90  C3   H32C  single    0.970  0.020  1.090
 G90  N    H     single    0.860  0.020  1.020
 G90  C1   H11C  single    0.970  0.020  1.090
 G90  C1   H12C  single    0.970  0.020  1.090
 G90  C1   H13C  single    0.970  0.020  1.090
 G90  C2   H21C  single    0.970  0.020  1.090
 G90  C2   H22C  single    0.970  0.020  1.090
 G90  C2   H23C  single    0.970  0.020  1.090
 G90  CB   HB1C  single    0.970  0.020  1.090
 G90  CB   HB2C  single    0.970  0.020  1.090
 G90  CD1  HD1   single    0.930  0.020  1.080
 G90  CE3  HE3   single    0.930  0.020  1.080
 G90  CZ3  HZ3   single    0.930  0.020  1.080
 G90  CH2  HH2   single    0.930  0.020  1.080
 G90  CZ2  HZ2   single    0.930  0.020  1.080
 G90  NE1  HE1   single    0.860  0.020  1.020

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
 G90  C7    C12  N1    180.00  3.000
 G90  C8    C7   C6    120.79  3.000
 G90  C8    C7   C12   120.17  3.000
 G90  C6    C7   C12   119.03  3.000
 G90  O2    C6   C11   125.29  3.000
 G90  O2    C6   C7    115.93  3.000
 G90  C11   C6   C7    118.79  3.000
 G90  H11   C11  C10   119.17  3.000
 G90  H11   C11  C6    121.10  3.000
 G90  C10   C11  C6    119.72  3.000
 G90  H10   C10  C9    119.84  3.000
 G90  H10   C10  C11   118.63  3.000
 G90  C9    C10  C11   121.53  3.000
 G90  H9    C9   C8    120.22  3.000
 G90  H9    C9   C10   120.61  3.000
 G90  C8    C9   C10   119.17  3.000
 G90  H8    C8   C9    120.66  3.000
 G90  H8    C8   C7    119.34  3.000
 G90  C9    C8   C7    119.99  3.000
 G90  C5    O2   C6    119.28  3.000
 G90  H52C  C5   H51C  108.01  3.000
 G90  H52C  C5   C4    109.99  3.000
 G90  H51C  C5   C4    110.56  3.000
 G90  H52C  C5   O2    110.22  3.000
 G90  H51C  C5   O2    110.31  3.000
 G90  C4    C5   O2    107.75  3.000
 G90  H4    C4   C3    108.36  3.000
 G90  H4    C4   O1    105.91  3.000
 G90  C3    C4   O1    113.17  3.000
 G90  H4    C4   C5    107.83  3.000
 G90  C3    C4   C5    109.47  3.000
 G90  O1    C4   C5    111.86  3.000
 G90  H1    O1   C4    108.53  3.000
 G90  H32C  C3   H31C  106.00  3.000
 G90  H32C  C3   N     113.87  3.000
 G90  H31C  C3   N     109.49  3.000
 G90  H32C  C3   C4    108.22  3.000
 G90  H31C  C3   C4    108.73  3.000
 G90  N     C3   C4    110.34  3.000
 G90  H     N    CA    108.25  3.000
 G90  H     N    C3    108.14  3.000
 G90  CA    N    C3    117.36  3.000
 G90  CB    CA   C2    110.55  3.000
 G90  CB    CA   C1    109.59  3.000
 G90  C2    CA   C1    109.61  3.000
 G90  CB    CA   N     104.63  3.000
 G90  C2    CA   N     112.73  3.000
 G90  C1    CA   N     109.60  3.000
 G90  H13C  C1   H12C  108.28  3.000
 G90  H13C  C1   H11C  108.09  3.000
 G90  H12C  C1   H11C  106.99  3.000
 G90  H13C  C1   CA    110.99  3.000
 G90  H12C  C1   CA    110.27  3.000
 G90  H11C  C1   CA    112.06  3.000
 G90  H23C  C2   H22C  107.36  3.000
 G90  H23C  C2   H21C  107.79  3.000
 G90  H22C  C2   H21C  107.84  3.000
 G90  H23C  C2   CA    111.36  3.000
 G90  H22C  C2   CA    111.36  3.000
 G90  H21C  C2   CA    110.95  3.000
 G90  HB2C  CB   HB1C  106.03  3.000
 G90  HB2C  CB   CG    109.54  3.000
 G90  HB1C  CB   CG    108.95  3.000
 G90  HB2C  CB   CA    107.16  3.000
 G90  HB1C  CB   CA    108.12  3.000
 G90  CG    CB   CA    116.53  3.000
 G90  CD1   CG   CD2   105.69  3.000
 G90  CD1   CG   CB    126.69  3.000
 G90  CD2   CG   CB    127.61  3.000
 G90  CE2   CD2  CE3   118.76  3.000
 G90  CE2   CD2  CG    107.30  3.000
 G90  CE3   CD2  CG    133.93  3.000
 G90  HE3   CE3  CZ3   120.24  3.000
 G90  HE3   CE3  CD2   120.60  3.000
 G90  CZ3   CE3  CD2   119.17  3.000
 G90  HZ3   CZ3  CH2   119.22  3.000
 G90  HZ3   CZ3  CE3   119.74  3.000
 G90  CH2   CZ3  CE3   121.05  3.000
 G90  HH2   CH2  CZ2   119.41  3.000
 G90  HH2   CH2  CZ3   119.38  3.000
 G90  CZ2   CH2  CZ3   121.21  3.000
 G90  HZ2   CZ2  CE2   121.31  3.000
 G90  HZ2   CZ2  CH2   121.20  3.000
 G90  CE2   CZ2  CH2   117.50  3.000
 G90  NE1   CE2  CZ2   130.41  3.000
 G90  NE1   CE2  CD2   107.27  3.000
 G90  CZ2   CE2  CD2   122.32  3.000
 G90  HE1   NE1  CD1   124.95  3.000
 G90  HE1   NE1  CE2   125.77  3.000
 G90  CD1   NE1  CE2   109.27  3.000
 G90  HD1   CD1  NE1   120.35  3.000
 G90  HD1   CD1  CG    129.19  3.000
 G90  NE1   CD1  CG    110.46  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
 G90  CONST_01  C10   C11  C6   C7      0.00   0.0  0
 G90  CONST_02  C10   C9   C8   C7      0.00   0.0  0
 G90  CONST_03  C9    C8   C7   C6      0.00   0.0  0
 G90  CONST_04  C9    C10  C11  C6      0.00   0.0  0
 G90  CONST_05  C8    C7   C6   C11     0.00   0.0  0
 G90  CONST_06  C8    C9   C10  C11     0.00   0.0  0
 G90  CONST_07  CZ3   CE3  CD2  CG    180.00   0.0  0
 G90  CONST_08  CZ2   CE2  CD2  CG    180.00   0.0  0
 G90  CONST_09  NE1   CE2  CD2  CG      0.00   0.0  0
 G90  CONST_10  CE2   NE1  CD1  CG      0.00   0.0  0
 G90  CONST_11  NE1   CD1  CG   CD2     0.00   0.0  0
 G90  CONST_12  CH2   CZ3  CE3  CD2     0.00   0.0  0
 G90  CONST_13  CH2   CZ2  CE2  CD2     0.00   0.0  0
 G90  CONST_14  CD1   NE1  CE2  CD2     0.00   0.0  0
 G90  CONST_15  CD1   CG   CD2  CE3   180.00   0.0  0
 G90  CONST_16  CZ2   CE2  CD2  CE3     0.00   0.0  0
 G90  CONST_17  NE1   CE2  CD2  CE3   180.00   0.0  0
 G90  CONST_18  CZ2   CH2  CZ3  CE3     0.00   0.0  0
 G90  CONST_19  CE2   CD2  CE3  CZ3     0.00   0.0  0
 G90  CONST_20  CE2   CZ2  CH2  CZ3     0.00   0.0  0
 G90  CONST_21  NE1   CE2  CZ2  CH2   180.00   0.0  0
 G90  CONST_22  CD1   NE1  CE2  CZ2   180.00   0.0  0
 G90  CONST_23  CD1   CG   CD2  CE2     0.00   0.0  0
 G90  CONST_24  C11   C6   C7   C12   180.00   0.0  0
 G90  CONST_25  C9    C8   C7   C12   180.00   0.0  0
 G90  CONST_26  O2    C6   C11  C10   180.00   0.0  0
 G90  CONST_27  O2    C6   C7   C8    180.00   0.0  0
 G90  CONST_28  CE3   CD2  CG   CB      0.00   0.0  0
 G90  CONST_29  CE2   CD2  CG   CB    180.00   0.0  0
 G90  CONST_30  NE1   CD1  CG   CB    180.00   0.0  0
 G90  CONST_31  H11   C11  C6   C7    180.00   0.0  0
 G90  CONST_32  H9    C9   C8   C7    180.00   0.0  0
 G90  CONST_33  H8    C8   C7   C6    180.00   0.0  0
 G90  CONST_34  H10   C10  C11  C6    180.00   0.0  0
 G90  CONST_35  HE3   CE3  CD2  CG      0.00   0.0  0
 G90  CONST_36  HE1   NE1  CD1  CG    180.00   0.0  0
 G90  CONST_37  HD1   CD1  CG   CD2   180.00   0.0  0
 G90  CONST_38  HZ3   CZ3  CE3  CD2   180.00   0.0  0
 G90  CONST_39  HZ2   CZ2  CE2  CD2   180.00   0.0  0
 G90  CONST_40  HH2   CH2  CZ3  CE3   180.00   0.0  0
 G90  Var_01    CD2   CG   CB   CA     91.51  30.0  2
 G90  Var_02    C4    C5   O2   C6    178.74  30.0  3
 G90  Var_03    CG    CB   CA   N    -179.15  30.0  3
 G90  Var_04    CA    N    C3   C4    178.38  30.0  3
 G90  Var_05    C1    CA   N    C3    -61.68  30.0  3
 G90  Var_06    H11C  C1   CA   N      68.19  30.0  3
 G90  Var_07    H21C  C2   CA   N      57.96  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
 G90  chir_01  C4  C5  O1  C3  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
 G90  plan-1  N1   0.020
 G90  plan-1  C12  0.020
 G90  plan-1  C7   0.020
 G90  plan-1  C6   0.020
 G90  plan-1  C11  0.020
 G90  plan-1  C10  0.020
 G90  plan-1  C9   0.020
 G90  plan-1  C8   0.020
 G90  plan-1  O2   0.020
 G90  plan-1  H8   0.020
 G90  plan-1  H11  0.020
 G90  plan-1  H10  0.020
 G90  plan-1  H9   0.020
 G90  plan-2  CB   0.020
 G90  plan-2  CG   0.020
 G90  plan-2  CD2  0.020
 G90  plan-2  CE3  0.020
 G90  plan-2  CZ3  0.020
 G90  plan-2  CH2  0.020
 G90  plan-2  CZ2  0.020
 G90  plan-2  CE2  0.020
 G90  plan-2  NE1  0.020
 G90  plan-2  CD1  0.020
 G90  plan-2  HD1  0.020
 G90  plan-2  HE3  0.020
 G90  plan-2  HZ3  0.020
 G90  plan-2  HH2  0.020
 G90  plan-2  HZ2  0.020
 G90  plan-2  HE1  0.020

